Rotamases, also referred to as peptidyl-prolyl cis-trans isomerases (PPIases) are a family of enzymes important in protein folding, assembly and transport. They act as catalysts to promote isomerization about the peptidyl-prolyl bond, which can have profound effects on protein function.

PPIases are divided into three classes, cyclophilins, FK-506 binding proteins (FKBPs) and the Pinl/parvulin class. While cyclophilins and FKBPs are distinguished by their ability to bind immunosuppressant molecules cyclosporin and FK-506, respectively, the Pinl/parvulin class binds neither of these immunosuppressants and is structurally unrelated to the other two classes. Known members of the Pinl/parvulin class include Pins 1-3 (Lu et al., Nature 380: 544-547,1996), Pin-L (Campbell et al. , Genomics 44: 157-162,1997), parvulin (Rahfeld et al., FEBS Letts 352: 180-184, 1994), dodo (Maleszka et al. , Proc Natl Acad Sci USA 93: 447-451,1996) and Essl/Pftl (Hanes et al., Yeast 5: 55-72,1989 ; and Hani et al., FEBS Letts 365: 198-202, 1995).

Recent research suggests that members of the Pinl/parvulin class are essential modulators of the cell cycle, and mitosis in particular. Lu et al. , Nature 380: 544-547,1996 reports that depletion of Pinl/Essl in yeast or human cells induces mitotic arrest followed by apoptosis, indicating that enzymes in this class serve an essential function in cell division and proliferation.

Accordingly, compounds inhibiting rotamases can serve as agents for the treatment of a variety of disorders which are characterized by an inappropriate cell proliferation including cancer and infectious diseases.

In the prior art a huge number of compounds are described which are active as inhibitors to rotamase. The respective compounds are, among others, peptide derivatives such as amino methylene-peptides which are described in European patent EP 0 610 743, or non-peptidic or non-peptidomimetic molecules.

Given the importance of rotamase there is an ongoing need in the art to provide further compounds which are suitable as inhibitors to rotamases and thus suitable to be used as a medicament for those diseases wherein a rotamase is involved in the pathological mechanism.

Accordingly, the problem underlying the present invention is to provide compounds which inhibit a rotamase. A further problem underlying the present invention is to provide new compounds for the treatment of diseases the pathophysiology of which involves an imbalanced or undesired activity of a rotamase.

In a first aspect the problem underlying the present invention is solved by a compound having the structure A- [Xlt-Y (0) wherein A is selected from the group comprising cycloalkyl, substituted cycloalkyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl; X is a spacer and is independently selected from the group comprising - M1-L1-K-L2-M2-, wherein K is selected from the group comprising C=T, O, S, S (O) and S (02), or is absent, with =T being selected from the group comprising =0, =S, =N-Re, =N-CH, =N-NO2 and =CH-NO2, LI and L2 are each and independently selected from the group comprising 0, S and primary amines, more particularly NR°, NRd ; or being individually and independent from each other absent MI and M2 are each and independently selected from the group comprising -(CRaRb) n-, - (CRfRg) zn-, cycloalkyl, substituted cycloakyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl heteroaryl, or being individually and independent from each other absent, wherein t is independently selected from n and/or m and is any integer from 0 to 10, whereby if t is 2 or more any of the spacer-M1-Ll-K-L2-M2-can be the same or different from any of the spacer (s) X repeated, wherein R, Rd and Re are independently from each other selected from the group H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl and substituted alkylheteroaryl; wherein Ra, Rb, Rf and Rg are independently from each other selected from the group H, OR17, SRIS, NRIsR20, halo, alkyl, substituted alkyl, alkylaryl, substituted alkylaryl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl and substituted alkylheteroaryl ; or may be independently from each other absent, and wherein Y is selected from the group comprising alkyl, substituted alkyl, straight alkyl, substituted straight alkyl, branched alkyl, substituted branched alkyl, straight alkenyl, substituted straight alkenyl, branched alkenyl, substituted branched alkenyl, straight alkynyl, substituted straight alkynyl, branched alkynyl, substituted branched alkynyl, cycloalkyl ; substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl, substituted heterocyclyl, mono-unsaturated heterocyclyl, poly-unsaturated heterocyclyl, mono-substituted poly-unsaturated heterocyclyl, poly-substituted poly-unsaturated heterocyclyl, mono- substituted mono-unsaturated heterocyclyl, mono-substituted poly-unsaturated heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, or wherein Y is absent.

In a preferred embodiment Y is different from a peptide.

In a further embodiment A is In a second aspect which is actually an embodiment of the first aspect of the invention, the problem is solved by a compound which has any of the structures according to formulae (I), (II), (III), (IV) or (V): wherein Rl, R2, R3 and R4 are each independently selected from the group comprising H, OR6, SR7, NR8R9, halo, alkyl, substituted alkyl, alkylaryl, substituted alkylaryl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl and substituted alkylheteroaryl; wherein R1 and R2, R2 and R3, R3 and R4, Rl and R3, Ri and R4, and R2 and R4 may be linked so as to form a ring comprising 4 to 12 members, preferably 5 to 10 members, more preferably 5 or 6 or 7 members, wherein Zl, Z2, Z3 and Z4 are each and independently selected from the group comprising- C (O)-, -C(S)-, -C(O)-NR10-, -C(S)-NR11-, -C(N-CN)-12-, -S(O)-, -S(O2)-, -S(O)- NR-13-,-S (02)-NRi4-,-0-, and-S-, or are each and individually absent; Rs is selected from the group comprising H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl, substituted alkylheteroaryl and-C (O)-Q ; wherein Q is selected from the group comprising H, NHRIs, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl, and substituted alkylheteroaryl ; and R6, R7, R8, R9, Rio, Rll, Rl2, Rl3, Rl4 and R15 are each and independently selected from the group comprising H, alkyl, substituted alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, alkylamino, substituted alkylamino, arylamino and substituted arylamino; X is a spacer and is independently selected from the group comprising -Ml-Ll-K-L2-M2-, wherein K is selected from the group comprising C=T, O, S, S (O) and S (02), or is absent, with =T being selected from the group comprising =0, =S, =N-R, =N-CN, =N-N02 and =CH-N02, LI and L2 are each and independently selected from the group comprising 0, S and primary amines, more particularly NR°, NRd ; or being individually and independent from each other absent M1 and M2 are each and independently selected from the group comprising -(CRaRb) n- -(CRfRg) m-, cycloalkyl, substituted cycloakyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl heteroaryl], or being individually and independent from each other absent, wherein D is Cl-C6 alkyl, preferably straight Cl-C6 alkyl, Cl-C6 alkenyl, preferably straight Cl-C6 alkenyl, Cl-C6 alkynyl, preferably straight Cl-C6 alkynyl, whereby preferably any of the alkyl, alkenyl and alkynyl may individually and independently comprise from 0 to 3 heteroatoms, and/or whereby preferably any of the alkyl, alkenyl and alkynyl can be individually and independently substituted, more preferably by 1 or 2 substituent (s) preferably each independently selected from H, halo, OR16, alkyl, and substituted alkyl, wherein n and m are each and independently selected from each other and are each any integer from 0 to 10, whereby if n is 2 or more, the group (s)-(CRaRb)-which is/are repeated, can be the same or different from any of the group (s)-(CRaRb)-, whereby any individual group can be linked to any other group or any moiety of the compound through a bond selected from the group comprising single bonds, double bonds and triple bonds, whereby if m is 2 or more, the group (s)-(CRÇRg)-which is/are repeated, can be the same or different from any of the group (s)-(CRfRg)-, whereby any individual group can be linked to any other group or any moiety of the compound through a bond selected from the group comprising single bonds, double bonds and triple bonds, wherein t is independently selected from n and/or m and is any integer from 0 to 10, whereby if t is 2 or more any of the spacer-M1-Ll-K-L2-M2-can be the same or different from any of the spacer (s) X repeated, wherein RC, Rd and Re are independently from each other selected from the group H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl and substituted alkylheteroaryl ; and Ra, Rb, Rf and Rg are independently from each other selected from the group H, Orin, SRis, NRl9R20, halo, alkyl, substituted alkyl, alkylaryl, substituted alkylaryl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl and substituted alkylheteroaryl; or may be independently from each other absent, and wherein E is Cl-C6 alkyl, preferably straight Cl-C6 alkyl, Cl-C6 alkenyl, preferably straight Cl-C6 alkenyl, Cl-C6 alkynyl, preferably straight Cl-C6 alkynyl, whereby preferably any of the alkyl, alkenyl and alkynyl may comprise individually and independently from 0 to 3 heteroatoms, and/or whereby preferably any of the alkyl, alkenyl and alkynyl can be individually and independently substituted by preferably 1 or 2 substituent (s) each preferably independently selected from the group comprising H, halo, OR21, alkyl, and substituted alkyl.

Ri6, Ri7, Rig, Rig, Rao and R2l are each and independently selected from the group comprising H, alkyl, substituted alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, alkylamino, substituted alkylamino, . arylamino and substituted arylamino ; wherein Y is selected from the group comprising alkyl, substituted alkyl, straight alkyl, substituted straight alkyl, branched alkyl, substituted branched alkyl, straight alkenyl, substituted straight alkenyl, branched alkenyl, substituted branched alkenyl, straight alkynyl, substituted straight alkynyl, branched alkynyl, substituted branched alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl, substituted heterocyclyl, mono-unsaturated heterocyclyl, poly-unsaturated heterocyclyl, mono-substituted poly-unsaturated heterocyclyl, poly-substituted poly-unsaturated heterocyclyl, mono- substituted mono-unsaturated heterocyclyl, poly-substituted mono-unsaturated heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, or wherein Y is absent.

In an embodiment Y is different from a peptide.

In an embodiment of the first and the second aspect of the present invention the moiety A and phenol moiety, respectively forms a cyclic structure with the spacer X and/or Y.

In an embodiment of the first and the second aspect of the present invention the compound is In a further embodiment of the first and the second aspect of the present invention the compound is selected from the group comprising In an embodiment of the first and the second aspect of the present invention K is C=T.

In a further embodiment of the first and the second aspect of the present invention T is selected from the group comprising O and S.

In a preferred embodiment of the first and the second aspect of the present invention T is 0.

In an alternative preferred embodiment of the first and the second aspect of the present invention T is S.

In a further alternative embodiment of the first and the second aspect of the present invention T is selected from the group comprising N-CN, N-NO2, CH-NO2 and N-Re. In an embodiment of the first and the second aspect of the present invention, more particularly the embodiment where T is either O or S, LI and L2 are each and independently a primary amine, preferably NRC and/or NRd.

In an embodiment of the first and the second aspect of the present invention n = 0 and m is any integer from 0 to 10.

In an embodiment of the first and the second aspect of the present invention Rl and/or R3 are selected from the group comprising halo, alkyl, substituted alkyl, heterocyclyl, substituted heterocyclyl, heteroaryl and substituted heteroaryl. In an even more preferred embodiment R is halo.

In an embodiment of the first and the second aspect of the present invention Rs is selected from the group comprising H and-C (O)-Q. In a preferred embodiment Q is selected from alkylheterocyclyl and substituted alkylheterocyclyl. In an even more preferred embodiment Q is selected from the group comprising N-acylated morpholino-, N-acylated piperazino-and N- acyl-derivatives.

In an embodiment of the first and the second aspect of the present invention R6 is alkyl or substituted alkyl.

In an embodiment of the first and the second aspect of the present invention R8 and Rg are individually and separately selected from the group comprising H, alkyl and substituted alkyl.

In an embodiment of the first and the second aspect of the present invention n and m are individually and independently any integer from 1 to 3.

In an alternative embodiment of the first and the second aspect of the present invention n is any integer from 0 to 3 and is preferably 0 or 1.

In a further alternative embodiment of the first and the second aspect of the present invention n and m are both 0.

In an embodiment of the first and the second aspect of the present invention t is 1 or 2.

In another embodiment of the first and the second aspect of the present invention Rc and/or Rd are each and independently from each other selected from the group comprising alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl and substituted alkylheteroaryl.

In still another embodiment of the first and the second aspect of the present invention Ra, Rb, Rf and Rg are each individually and independently from each other selected from the group comprising H, Oral7, SRlB, NR19R20, halo, alkyl and substituted alkyl.

In a preferred embodiment of the first and the second aspect of the present invention Y is selected from the group comprising alkyl, substituted alkyl, straight alkyl, substituted straight alkyl, branched alkyl, substituted branched alkyl, straight alkenyl, substituted straight alkenyl, branched alkenyl, substituted branched alkenyl, straight alkynyl, substituted straight alkynyl, branched alkylnyl and substituted branched alkynyl.

In an alternate preferred embodiment of the first and the second aspect of the present invention Y is selected from the group comprising cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl, substituted heterocyclyl, mono- unsaturated heterocyclyl, poly-unsaturated heterocyclyl, mono-substituted mono-unsaturated heterocyclyl, poly-substituted mono-unsaturated heterocyclyl, mono-substituted poly- unsaturated heterocyclyl, poly-substituted poly-unsaturated heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, wherein Y is different from a peptide or is absent.

In a particularly preferred embodiment of the first and the second aspect of the present invention which is also referred to as the NR-CZ-NR embodiment X is - (CRaRb) nNRCCZNRd_ (CRfRg) and Z is preferably selected from the group comprising 0, S, N-CN, N-NO2 and CH-NO2.

In an embodiment of the NR-CZ-NR embodiment m is any integer from 1 to 10.

In an embodiment of the NR-CZ-NR embodiment Rs is selected from the group comprising H and-C (O)-Q, preferably m is any integer from 1 to 10.

In an embodiment of the NR-CZ-NR embodiment wherein R5 is H.

In an embodiment of the NR-CZ-NR embodiment n is 0, preferably R5 being selected from the group comprising H and-C (O)-Q, more preferably m being any integer from 1 to 10. In an alternative embodiment n is any integer from 1 to 10.

In an embodiment of the NR-CZ-NR embodiment t is 1.

In an embodiment of the first and/or second aspect of the present invention and particularly in an embodiment of the NR-CZ-NR embodiment Y is selected from the group comprising alkyl, substituted alkyl, straight alkyl, substituted straight alkyl, branched alkyl, substituted branched alkyl, straight alkenyl, substituted straight alkenyl, branched alkenyl, substituted branched alkenyl, straight alkynyl, substituted straight alkynyl, branched alkynyl and substituted branched alkynyl.

In an embodiment of the first and/or second aspect of the present invention and particularly in an embodiment of the NR-CZ-NR embodiment Y is selected from the group comprising cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl, substituted heterocyclyl, mono-unsaturated heterocyclyl, poly-unsaturated heterocyclyl, mono-substituted poly-unsaturated heterocyclyl, mono-substituted mono-unsaturated heterocyclyl, poly-substituted mono-unsaturated heterocyclyl, poly-substituted poly- unsaturated heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, wherein . Y is different from a peptide. Alternatively, Y can be absent.

In an embodiment of the NR-CZ-NR embodiment Rc and/or Rd are independently from each other selected from the group alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl and substituted alkylheteroaryl.

In a particularly preferred embodiment of the first and the second aspect of the present invention which is also referred to as the NR embodiment is X is - (CRaRb) p NR°- (CRfRg) m In an embodiment Ra, Rb, R°, Rd, Re, Rf and Rg are independently from each other selected from the group H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocyclyl, substituted heterocyclyl, heteroaryl, substituted heteroaryl.

In an embodiment R5 is selected from the group comprising H and-C (O)-Q. Preferably Rs is H.

In a further embodiment m is any integer between 1 and 10. Preferably n is 0.

In a still further embodiment Rs is selected from the group comprising H and-C (O)-Q, whereby m is any integer between 1 and 10. Preferably n is 0. In an even more preferred embodiment Rs is H.

In a preferred embodiment of the NR embodiment X is - (CRaRb)n-NRc-(CRfRg)m-, and wherein t is 1. Preferably, Y is selected from the group comprising alkyl, substituted alkyl, straight alkyl, substituted straight alkyl, branched alkyl, substituted branched alkyl, straight alkenyl, substituted straight alkenyl, branched alkenyl, substituted branched alkenyl, straight alkynyl, substituted straight alkynyl, and substituted branched alkynyl. Preferably Rs is selected from the group comprising H and-C (O)-Q and even more preferably Rs is H. In a still further preferred embodiment n is 0.

In a preferred embodiment of the NR embodiment, wherein X is - (CR'R\-NR°- (CRR%-, and wherein t is lm is any integer between 1 and 10, preferably m is any integer between 2 and 10. Preferably, Rs is selected from the group comprising H and-C (O)-Q, and more preferably Rs is H. Also preferably Y is selected from the group comprising cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl, substituted heterocyclyl, mono-unsaturated heterocyclyl, poly-unsaturated heterocyclyl, mono-substituted poly-unsaturated heterocyclyl, mono-substituted mono-unsaturated heterocyclyl, poly- substituted mono-unsaturated heterocyclyl, poly-substituted poly-unsaturated heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, wherein Y is different from a peptide or is absent.

In a preferred embodiment Rs is selected from the group comprising H and-C (0)-Q, preferably Rs is H and even more preferably n is 0.

In a particularly preferred embodiment of the first and the second aspect of the present invention which is also referred to as the NR-Z embodiment X is -(CRaRb)n-NRc-Z-(CRfRg)m- and can be inserted in any orientation into any of the preceding formulae, and wherein Z is selected from the group comprising C (O), C (S), S (02), C (O)-O, and C (O)- S.

In an embodiment Rs is selected from the group comprising H and-C (0)-Q, preferably Rs is H.

. In an embodiment n is 0.

In a further embodiment of the NR-Z embodiment X is - (CRaRb) ri NR°-Z- (CRfRg) m and can be inserted in any orientation into any of the preceding formulae, and Z is selected from the group comprising C (O), C (S), S (02), C (O)-O, and C (O)-S, and wherein preferably t is 1. Preferably Y is selected from the group comprising alkyl, substituted alkyl, straight alkyl, substituted straight alkyl, branched alkyl, substituted branched alkyl, straight alkenyl, substituted straight alkenyl, branched alkenyl, substituted branched alkenyl, straight alkynyl, substituted straight alkynyl, and substituted branched alkynyl. More preferably Rs is selected from the group comprising H and-C (O)-Q and even more preferably R5 is H. In any of the latter embodiments n is 0.

In a further embodiment of the NR-Z embodiment wherein X is -(CRaRb) n-NRC-Z-(CRfRg) m-and can be inserted in any orientation into any of the preceding formulae, and Z is selected from the group comprising C (O), C (S), S (02), C (O)-O, and C (O)-S, and wherein preferably t is 1, m is any integer between 1 and 10. Preferably, R5 is selected from the group comprising H and-C (O)-Q, and more preferably Rs is H. In an embodiment of the latter embodiments Y is selected from the group comprising cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl, substituted heterocyclyl, mono-unsaturated heterocyclyl, poly-unsaturated heterocyclyl, mono-substituted poly- unsaturated heterocyclyl, mono-substituted mono-unsaturated heterocyclyl, poly-substituted mono-unsaturated heterocyclyl, poly-substituted poly-unsaturated heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, wherein Y is different from a peptide or wherein Y is absent. Preferably, Rs is selected from the group comprising H and-C (O}-Q, more preferably R5 is H. In a particularly preferred embodiment n is 0.

In the embodiment where Y is as defined in the preceding paragraph, m is preferably any integer between 2 and 10. Preferably, Rs is selected from the group comprising H and-C (O)- Q and more preferably Rs is H. Even more preferably, in any of these embodiments n is 0. In a third aspect which is actually an embodiment of the first aspect of the invention, the problem is solved by a compound which has any of the structures according to formulae (XIV), (XV), (XVI), (XVII) or (XVIII): wherein Rl, R2, R3 and R4 are each independently selected from the group comprising H, OR6, SR7, NR8R9, halo, alkyl, substituted alkyl, alkylaryl, substituted alkylaryl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl and substituted alkylheteroaryl; wherein R1 and R2, R2 and R3, R3 and R4, Rl and R3, Ri and R4, and Ra and R4 may be linked so as to form a ring comprising 4 to 12 members, preferably 5 to 10 members, more preferably 5 or 6 or 7 members, wherein Zl, Z2, Z3 and Z4 are each and independently selected from the group comprising C (O)-,-C (S) -,-C (O)-NRio-,-C (S)-NRil-,-C (N-CN)-NR12-,-S (O)-,-S (02)-,-S (O)- NRi3-,-S (02)-NRi4-,-O-, and-S-, or are each and individually absent; R5 is selected from the group comprising H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl, substituted alkylheteroaryl and-C (0)-Q ; wherein Q is selected from the group comprising H, NHRls, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl, and substituted alkylheteroaryl; and R6, R7, R8, Rg, Rio, Rn, Riz, Ri3, Rl4 and Pis arc each and independently selected from the group comprising H, alkyl, substituted alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, alkylamino, substituted alkylamino, arylamino and substituted arylamino; X is a spacer and is independently selected from the group comprising -Ml-Ll-K-L2-M2-, wherein K is selected from the group comprising C=T, 0, S, S (O) and S (02), or is absent, with =T being selected from the group comprising =0, =S, =N-R, =N-CN, =N-N02 and =CH-NO2, LI and L2 are each and independently selected from the group comprising O, S and primary amines, more particularly Nle, NRd ; or being individually and independent from each other absent M1 and M2 are each and independently selected from the group comprising - (CRaRb) n-, -(CRfRg) m-, cycloalkyl, substituted cycloakyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl heteroaryl], or being individually and independent from each other absent, wherein D is Cl-C6 alkyl, preferably straight Cl-C6 alkyl, Cl-C6 alkenyl, preferably straight Ci-C6 alkenyl, Cl-C6 alkynyl, preferably straight Ci-C6 alkynyl, whereby preferably any of the alkyl, alkenyl and alkynyl may individually and independently comprise from 0 to 3 heteroatoms, and/or whereby preferably any of the alkyl, alkenyl and alkynyl can be individually and independently substituted, more preferably by 1 or 2 substituent (s) preferably each independently selected from H, halo, OR16, alkyl, and substituted alkyl, wherein n and m are each and independently selected from each other and are each any integer from 0 to 10, whereby if n is 2 or more, the group (s)-(CRaRb)-which is/are repeated, can be the same or different from any of the group (s)-(CRaRb)-, whereby any individual group can be linked to any other group or any moiety of the compound through a bond selected from the group comprising single bonds, double bonds and triple bonds, whereby if m is 2 or more, the group (s)-(CRfRg)-which is/are repeated, can be the same or different from any of the group (s)- (CRfRg)-, whereby any individual group can be linked to any other group or any moiety of the compound through a bond selected from the group comprising single bonds, double bonds and triple bonds, wherein t is independently selected from n and/or m and is any integer from 0 to 10, whereby if t is 2 or more any of the spacer-Ml-Ll-K-L2-M2-can be the same or different from any of the spacer (s) X repeated, wherein RC, R and Re are independently from each other selected from the group H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl,. alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl ; alkylheteroaryl and substituted alkylheteroaryl; and Ra, Rb, Rf and Rg are independently from each other selected from the group H, Oral7, Sprig, NRlgR20 halo, alkyl, substituted alkyl, alkylaryl, substituted alkylaryl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl and substituted alkylheteroaryl ; or may be independently from each other absent, and wherein E is Cl-C6 alkyl, preferably straight Cl-C6 alkyl, Cl-C6 alkenyl, preferably straight Cl-C6 alkenyl, Cl-C6 alkynyl, preferably straight Cl-C6 alkynyl, whereby preferably any of the alkyl, alkenyl and alkynyl may comprise individually and independently from 0 to 3 heteroatoms, and/or whereby preferably any of the alkyl, alkenyl and alkynyl can be individually and independently substituted by preferably 1 or 2 substituent (s) each preferably independently selected from the group comprising H, halo, OR21, alkyl, and substituted alkyl.

Rz6, Ri7, Ri8< Rig, Rao and R2z are each and independently selected from the group comprising H, alkyl, substituted alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, alkylamino, substituted alkylamino, arylamino and substituted arylamino; wherein Y is selected from the group comprising alkyl, substituted alkyl, straight alkyl, substituted straight alkyl, branched alkyl, substituted branched alkyl, straight alkenyl, substituted straight alkenyl, branched alkenyl, substituted branched alkenyl, straight alkynyl, substituted straight alkynyl, branched alkynyl, substituted branched alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl, substituted heterocyclyl, mono-unsaturated heterocyclyl, poly-unsaturated heterocyclyl, mono-substituted poly-unsaturated heterocyclyl, poly-substituted poly-unsaturated heterocyclyl, mono- substituted mono-unsaturated heterocyclyl, poly-substituted mono-unsaturated heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, or wherein Y is absent.

In an embodiment Y is different from a peptide.

In an embodiment of the first and the third aspect of the present invention the moiety A and phenol moiety, respectively forms a cyclic structure with the spacer X and/or Y.

In an embodiment of the first and the third aspect of the present invention the compound is In a further embodiment of the first and the third aspect of the present invention the compound is selected from the group comprising In an embodiment of the first and the third aspect of the present invention K is C=T.

In a further embodiment of the first and the third aspect of the present invention T is selected from the group comprising O and S.

In a preferred embodiment of the first and the third aspect of the present invention T is 0.

In an alternative preferred embodiment of the first and the third aspect of the present invention T is S.

In a further alternative embodiment of the first and the third aspect of the present invention T is selected from the group comprising N-CN, N-NO2, CH-NO2 and N-Re.

In an embodiment of the first and the third aspect of the present invention, more particularly the embodiment where T is either O or S, Ll and L2 are each and independently a primary amine, preferably NRe and/or NRd.

In an embodiment of the first and the third aspect of the present invention n = 0 and m is any integer from 0 to 10.

In an embodiment of the first and the third aspect of the present invention Rl and/or R3 are selected from the group comprising halo, alkyl, substituted alkyl, heterocyclyl, substituted heterocyclyl, heteroaryl and substituted heteroaryl. In an even more preferred embodiment R is halo.

In an embodiment of the first and the third aspect of the present invention R5 is selected from the group comprising H and-C (0)-Q. In a preferred embodiment Q is selected from alkylheterocyclyl and substituted alkylheterocyclyl. In an even more preferred embodiment Q is selected from the group comprising N-acylated morpholino-, N-acylated piperazino-and N- acyl-derivatives.

In an embodiment of the first and the third aspect of the present invention R6 is alkyl or substituted alkyl.

In an embodiment of the first and the third aspect of the present invention R8 and R9 are individually and separately selected from the group comprising H, alkyl and substituted alkyl.

In an embodiment of the first and the third aspect of the present invention n and m are individually and independently any integer from 1 to 3.

In an alternative embodiment of the first and the third aspect of the present invention n is any integer from 0 to 3 and is preferably 0 or 1.

In a further alternative embodiment of the first and the third aspect of the present invention n and m are both 0.

In an embodiment of the first and the third aspect of the present invention t is 1 or 2.

In another embodiment of the first and the third aspect of the present invention R° and/or Rd are each and independently from each other selected from the group comprising alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl and substituted alkylheteroaryl.

In still another embodiment of the first and the third aspect of the present invention Ra, Rb, Rf and Rg are each individually and independently from each other selected from the group comprising H, OR17, SRl8, NRlaR20, halo, alkyl and substituted alkyl.

In a preferred embodiment of the first and the third aspect of the present invention Y is selected from the group comprising alkyl, substituted alkyl, straight alkyl, substituted straight alkyl, branched alkyl, substituted branched alkyl, straight alkenyl, substituted straight alkenyl, branched alkenyl, substituted branched alkenyl, straight alkynyl, substituted straight alkynyl, branched alkylnyl and substituted branched alkynyl.

In an alternate preferred embodiment of the first and the third aspect of the present invention Y is selected from the group comprising cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl, substituted heterocyclyl, mono-unsaturated heterocyclyl, poly-unsaturated heterocyclyl, mono-substituted mono-unsaturated heterocyclyl, poly-substituted mono-unsaturated heterocyclyl, mono-substituted poly-unsaturated heterocyclyl, poly-substituted poly-unsaturated heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, wherein Y is different from a peptide or is absent.

In a particularly preferred embodiment of the first and the third aspect of the present invention which is also referred to as the NR-CZ-NR embodiment X is - (CR'R\-NR'-CZ-NR'L (CR- and Z is preferably selected from the group comprising 0, S, N-CN, N-NO2 and CH NOa.

In an embodiment of the NR-CZ-NR embodiment m is any integer from 1 to 10.

In an embodiment of the NR-CZ-NR embodiment Rs is selected from the group comprising H and-C (O)-Q, preferably m is any integer from 1 to 10.

In an embodiment of the NR-CZ-NR embodiment wherein Rs is H.

In an embodiment of the NR-CZ-NR embodiment n is 0, preferably R5 being selected from the group comprising H and-C (O)-Q, more preferably m being any integer from 1 to 10. In an alternative embodiment n is any integer from 1 to 10.

In an embodiment of the NR-CZ-NR embodiment t is 1.

In an embodiment of the first and/or third aspect of the present invention and particularly in an embodiment of the NR-CZ-NR embodiment Y is selected from the group comprising alkyl, substituted alkyl, straight alkyl, substituted straight alkyl, branched alkyl, substituted branched alkyl, straight alkenyl, substituted straight alkenyl, branched alkenyl, substituted branched alkenyl, straight alkynyl, substituted straight alkynyl, branched alkynyl and substituted branched alkynyl.

In an embodiment of the first and/or third aspect of the present invention and particularly in an embodiment of the NR-CZ-NR embodiment Y is selected from the group comprising cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl, substituted heterocyclyl, mono-unsaturated heterocyclyl, poly-unsaturated heterocyclyl, mono-substituted poly-unsaturated heterocyclyl, mono-substituted mono-unsaturated heterocyclyl, poly-substituted mono-unsaturated heterocyclyl, poly-substituted poly- unsaturated heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, wherein Y is different from a peptide. Alternatively, Y can be absent.

In an embodiment of the NR-CZ-NR embodiment Rc andlor Rd are independently from each other selected from the group alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl and substituted alkylheteroaryl.

In a particularly preferred embodiment of the first and the third aspect of the present invention which is also referred to as the NR embodiment is X is - (CR) n-NR'- (CR- In an embodiment Ra, Rb, Rc, Rd, Re, Rf and Rg are independently from each other selected from the group H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocyclyl, substituted heterocyclyl, heteroaryl, substituted heteroaryl.

In an embodiment Rs is selected from the group comprising H and-C (O)-Q. Preferably Rs is H.

In a further embodiment m is any integer between 1 and 10. Preferably n is 0.

In a still further embodiment Rs is selected from the group comprising H and-C (0)-Q, whereby m is any integer between 1 and 10. Preferably n is 0. In an even more preferred embodiment Rs is H.

In a preferred embodiment of the NR embodiment X is - (CRaRb) n-NR°- (CRfR$) r,,-, and wherein t is 1. Preferably, Y is selected from the group comprising alkyl, substituted alkyl, straight alkyl, substituted straight alkyl, branched alkyl, substituted branched alkyl, straight alkenyl, substituted straight alkenyl, branched alkenyl, substituted branched alkenyl, straight alkynyl, substituted straight alkynyl, and substituted branched alkynyl. Preferably Rs is selected from the group comprising H and-C (O)-Q and even more preferably Rs is H. In a still further preferred embodiment n is 0.

In a preferred embodiment of the NR embodiment, wherein X is - (CRaRb)n-NRc-(CRfRg)m-, and wherein t is lm is any integer between 1 and 10, preferably m is any integer between 2 and 10. Preferably, Rs is selected from the group comprising H and-C (0)-Q, and more preferably Rs is H. Also preferably Y is selected from the group comprising cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl, substituted heterocyclyl, mono-unsaturated heterocyclyl, poly-unsaturated heterocyclyl, mono-substituted poly-unsaturated heterocyclyl, mono-substituted mono-unsaturated heterocyclyl, poly- substituted mono-unsaturated heterocyclyl, poly-substituted poly-unsaturated heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, wherein Y is different from a peptide or is absent.

In a preferred embodiment Rs is selected from the group comprising H and-C (O)-Q, preferably Rs is H and even more preferably n is 0.

In a particularly preferred embodiment of the first and the third aspect of the present invention which is also referred to as the NR-Z embodiment X is - n-NRC-Z-(CRfRg) m-and can be inserted in any orientation into any of the preceding formulae, and wherein Z is selected from the group comprising C (O), C (S), S (02), C (O>O, and C (O)- S.

In an embodiment Rs is selected from the group comprising H and-C (O)-Q, preferably Rs is H.

In an embodiment n is 0.

In a further embodiment of the NR-Z embodiment X is -(CRaRb) n-NRC-Z-(CRfRg) m-and can be inserted in any orientation into any of the preceding formulae, and Z is selected from the group comprising C (O), C (S), S (02), C (O)-O, and C (OkS, and wherein preferably t is 1. Preferably Y is selected from the group comprising alkyl, substituted alkyl, straight alkyl, substituted straight alkyl, branched alkyl, substituted branched alkyl, straight alkenyl, substituted straight alkenyl, branched alkenyl, substituted branched alkenyl, straight alkynyl, substituted straight alkynyl, and substituted branched alkynyl. More preferably Rs is selected from the group comprising H and-C (O)-Q and even more preferably Rs is H. In any of the latter embodiments n is 0.

In a further embodiment of the NR-Z embodiment wherein X is -(CRaRb) n-NRC-Z-(CRfRg) m-and can be inserted in any orientation into any of the preceding formulae, and Z is selected from the group comprising C (O), C (S), S (02), C (O)-O, and C (O)-S, and wherein preferably t is 1, m is any integer between 1 and 10. Preferably, Rs is selected from the group comprising H and-C (O)-Q, and more preferably Rs is H. In an embodiment of the latter embodiments Y is selected from the group comprising cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl, substituted heterocyclyl, mono-unsaturated heterocyclyl, poly-unsaturated heterocyclyl, mono-substituted poly- unsaturated heterocyclyl, mono-substituted mono-unsaturated heterocyclyl, poly-substituted mono-unsaturated heterocyclyl, poly-substituted poly-unsaturated heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, wherein Y is different from a peptide or wherein Y is absent. Preferably, Rs is selected from the group comprising H and-C (O)-Q, more preferably Rs is H. In a particularly preferred embodiment n is 0.

In the embodiment where Y is as defined in the preceding paragraph, m is preferably any integer between 2 and 10. Preferably, Rs is selected from the group comprising H and-C (Of Q and more preferably Rs is H. Even more preferably, in any of these embodiments n is 0.

As used herein, any integer between or any integer from e. g., 0 and 10 or 0 to 10 means 1,2, 3,4, 5,6, 7,8, 9 and 10.

In an embodiment of any aspect of the present invention Y is different from a peptide. As used herein peptide means a polymer of at least two amino acids which are linked by an amide bond. Any of the amino acids may be a natural or a non natural acid.

In a preferred embodiment of any aspect of the present invention m, n and t are independently selected from each other and are preferably any integer between 0 and 5; more preferably if n is 0, m is different from 0 and if m is 0, n is different from 0.

Also as used herein the term compound (s) according to the present invention means any compound (s) according to any aspect of the present invention. If not indicated to the contrary, any embodiment of the present invention is an embodiment of any aspect of the present invention.

Re is selected from the group comprising H, alkyl, aryl, alkoxy, aryloxy, alkylamino and arylamino.

In an even more preferred embodiment of the inventive compound Rl, R2, R3 R4 and/or Rs have independently from each other one or more groups of the formula Rf ; whereby Rf is selected from the group comprising alkyl, cycloalkyl, aryl, heterocyclyl, heteroaryl, alkoxy, aryloxy, arylalkoxy, alkoxycarbonyl, aryloxycarbonyl, alkanoyl, aroyl, alkanoyloxy, aroyloxy, carbamoyl, alkanoylamino, aroylamino, alkylthio, arylthio, ureido and amine.

In a further preferred embodiment the alkylthio group is derivatized, preferably the sulfur atom of the alkylthio group is oxidized to a sulfoxide or sulfone ; the arylthio group is derivatized, preferably the sulfur atom of the arylthio group is oxidized to a sulfoxide or sulfone, the ureido group is derivatized, preferably the nitrogen atom of the ureido group is independently mono-or di-substituted, more preferably the substitution is selected from the group comprising alkyl, aryl, heterocyclyl, heteroaryl, alkoxycarbonylamino, aryloxycarbonylamino, alkylcarbamoyloxy, arylcarbamoyloxy, alkylsulfonylamino, arylsulfonylamino, alkylaminosulfonyl, and arylaminosulfonyl ; and/or the amino group is derivatized, preferably the nitrogen atom is independently mono-or di- substituted by alkly, aryl, heterocyclyl, heteroalyl, halogen, hydroxy, oxo, carboxy, cyano, nitro, amidino and guanidino.

In a still more preferred embodiment Rf is further substituted by one ore more groups Rg, whereby Rg is selected from the group comprising alkyl, cycloalkyl, aryl, arylalkyl, alkoxy, aryloxy, arylalkoxy, alkanol, aroyl, amino, halogen, hydroxy, oxo, carboxy, cyano, nitro, amidino and guanidino.

Particularly preferred compounds according to the present invention are the compounds specified in the following table 1: Structure Chemical name Formula Synthesis MolWeight MS data methods OH H H 1 I NN\^/o 3_3- (5-Chloro-2-hydroxy-phenyl)- r o o ureido]-propionic acid ethyl ester Ci OH H H 2 v T 1-(5-Chloro-2-hydroxy-phenyl)-3-C12H17CIN202 A 256. 73 256. 9 cri OH 3 \ N N 1-Benzyl-3- (5-chloro-2-hydroxy- a ci OH 4 \ N N 1- (5-Chloro-2-h drox-henyl)-3- C15H15C1N202 A 290. 74 290. 9 9 (2-methyl-benzyl)-urea cl OU H H 5 1- (5-Chloro-2-hydroxy-phenyl)-3- C15Hl5CIN202 A 290. 75 291. 2 cl phenethyl-urea o OH '6r"T"0 'C15H15C A 290. 7.. . 2 0 OH N N I ^ I 1- (5-C (loro-2-hydroxy-phenyl)-3- Y (1, 1, 3, 3-tetramethyl-butyl)-urea cl OH 7 I NN 1-tert-Butyl-3- (5-chloro-2- C11H15C1N202 A 242. 70 243. 0 < hydroxy-phenyl)-urea Ci OU °"H H r y p C14H19C1N202 A 282. 77 283. 1 cl cyclohexylmethyl-urea cl OH CF, Oh I- (5-Chloro-2-hydroxy-phenyl)-3- ( (4-trifluoromethyl-benzyl)-urea o OH H H 10 1) t tcx 1-(S-Chloro-2-hydroxy-phenyl)-3-C13H9C13N202 A 33159 331. 9 a cl (3, 5-dichloro-phenyl)-urea ci OH H H X T aCI l-(5-Cioro-2 hydroxy-PhenYl)-3 Cl3HlOCl N202 A 297. 14 297. 7 ( 0 ci (4-chloro-phenyl)-urea cri 0 OH H H 12 | f tX 1-(5-Chloro-2-hydroxy-phenyl)-3-C14HlOClF3N202 A 330. 69 331. 0 « t ° CF3 (4-trifluoromethyl-phenyl)-urea cri OH H H 13 (N) N\o 1-(5-Chloro-2-hydroxy-phenyl)-3-C13H17ClN202 A 268. 74 269. 1 /o cyclohexyl-urea a OH H H 14 Ny N 1- (5-Chloro-2-hydroxy-phenyl)-3- C14HIOCIF3N203 A 346. 69 346. 9 YJ ° oOCF3 (4-ttifluoromethoxy-phenyl)-urea 3 Ct OH H H 15 S Y 4 1-(5-Chloro-2-hydroxy-phenyl)-3-C14HlOCIN302 A 287. 70 287. 9 Y CN (4-cyano-phenyl)-urea " ! OH H H 16 $N H I-Benzo [1, 31dioxol-5-yl-3-(5-\ C14HIIC1 9204 A 306. 70 306. 9 Y o o chloro-2-hydroxy-phenyl)-urea cl OH 17 r NxfNu 1-(5-Chloro-2-hydroxy-phenyl)-3-C14H13ClN202 A 276. 72 276. 9 rl 11 \ C14H13C1N202 A 276. 72 276. 9 ? o 9 o-tolyl-urea cl OH H H 18 N N OM 1-(5-Chloro-2-hydroxy-phenyl)-3-C14H13ClN203 A 292. 72 292. 9 Y (3-methoxy-phenyl)-urea cl OU H H N N 19 N y 1- (5-Chloro-2-hydroxy-phenyl)-3- C15Hl5CIN202 A 290. 75 290. 9 ( ° (2, 6-dimethyl-phenyl)-urea cl OH H H 20 \ N N OMe 1_ (5-Chloro-2-hydroxy-phenyl)-3- (3, 4, 5-trimethoxy-phenyl)-urea Cl OMe 0 OMe Oh 21 N NN 1- (5-Chloro-2-hydroxy-phenyl)-3- na hthalen-1-1-urea C17H13C1N202 A 312. 75 313. 1 Ci ci OH 22 H 1-Adamantan-1-yl-3- (5-chloro-2- N NH C17H21C1N202 A 320. 82 321. 4 hydroxy-phenyl)-urea zozo Ci OH H H 23 N y N 1- (S-Chloro-2-hydroxy-phenyl)-3- Y ° ow (4-phenoxy-phenyl)-urea o OH H H 24 Nr N 1-(5-Chloro-2-hydroxy-phenyl)-3-C13H1lCIN202 A 262. 70 263. 2 Y phenyl-urea ----' OH N N,,,,-yO, _,.- 3- [3- (3, 5-Dichloro-2-hydroxy- 25 t d o õ phenyl)-ureido]-propionicacid C12H14C12N204 A 321. 16 321. 9 "r"ethyl ester o ethyl ester ci OH H H CI N N 1- (3, 5-Dichloro-2-hydroxy- o phenyl)-3-pentyl-urea cl OH H H y I-Benzyl-3- (3, 5-dicWoro-2- o hydroxy-phenyl)-urea ci OH H H CI N'N \ 1- (3, 5-Dichloro-2-hydroxy- C15H14C12N202 A 325. 19 325. 9 o phenyl)-3- (2-methyl-benzyl)-urea ci OH H H CI N N 1- (3, 5-Dichloro-2-hydroxy- Y o v phenyl)-3-phenethyl-urea cl o OH N N 1- (3, 5-Dichloro-2-hydroxy- 30 0 phenyl)-3- (1, 1, 3, 3-tetramethyl- C15H22C12N202 A 333. 25 334. 0 butyl)-urea o OH CI N N \ o'hydroxy-phenyl)-urea o OH 31 drox-hen 1 urea C11H14C12N202 A 277. 15 277. 8 i Y YP Y) ci OH H H 32 I N'N 1- (3, 5-Dichloro-2-hydroxy- o phenyl)-3-cyclohexylmethyl-urea ci /caf3 OH OH H CFq 1- (3, 5-Dichloro-2-hydroxy- phenyl)-3- (4-trifluoromethyl- benzyl)-urea ci OH N N_qCl 1- (3, 5-Dichloro-2-hydroxy- 34 0 phenyl)-3- (3, 5-dichloro-phenyl)- C13H8Cl4N202A366. 03 366. 9 urea cri OH Cl Cl S 35 Cl>ßNN>¢DX 1-(3, 5-Dichloro-2-hydroxy-C 13H9CD13N202 A 331. 58 331. 9 Y ° ci phenyl)-3-(4-chloro-phenyl)-urea ci OH H H OH 1-(3, 5-Dichloro-2-hydroxy- 36 0 phenyl)-3- (4-trifluoromethyl- C14H9Cl2F3N202A365. 13 365. 9 caf3 phenyl)-urea a OH H H cri N'-o 1- (3, 5-Dichloro-2-hydroxy- C13Hl6Cl2N202A303. 18 304. 0 , ' o' phenyl)-3-cyclohexyl-uiea a OH N N 1- (3, 5-Dichloro-2-hydroxy- 38 0 phenyl)-3- (4-trifluoromethoxy- C14H9Cl2F3N203A381. 13 381. 8 ocF3 phenyl)-urea ci OU H H CI N N OH YJ ° oCN phenyl)-3-(4-cyano-phenyl)-urea OH Cl OH CI N N p 40 I-Benzc) [1, 3] dioxol-5-yl-3- (3, 5- C14HIOC12N204A341. 15 341. 7 Y o o dichloro-2-hydroxy-phenyl)-urea. ci OH H H 1- (3, 5-Dichloro-2-hydroxy- 41 CI I \ NN \ C14H12C12N202 A 311. 16 311. 8 41 9 phenyl)-3-o-tolyl-urea ci OH CI N N OMe 1- (3, 5-Dichloro-2-hydroxy- 42 11 J t J phenyl)-3- (3-methoxy-phenyl)- C14H12CI2N203 A 327. 16 327. 5 urea Ci OH CI N N 1- (3, 5-Dichloro-2-hydroxy- 43 t ! J"ii j phenyl)-3- (2, 6-dimethyl-phenyl)- C15H14C12N202 A 325. 19 325. 6 ° ea urea ci OH N NqOOMe 1- (3, 5-Dichloro-2-hydroxy- 44 phenyl)-3- (3, 4, 5-trimethoxy-C16H17C12N205 A 387. 21 387. 6 0 Me phenyl)-urea Cl Oh H H 45 N N 1- (3, 5-Dichloro-2-hydroxy- C17Hl2Cl2N202A 347. 20 347. 6 45 cl phenyl)-3-naphthalen-1-yl-urea cl OH OH CIN H l-Adamantan-l-yl-3- (3, 5-dichloro- ci7H20C ! 2N202 A 355. 26 355. 7 46 2-hydroxy-phenyl)-urea cl S ci OH CI/N N%' /1- (3, 5-Dichloro-2-hydroxy- 47 iJJ ° uoX phenyl)-3-(4-phenoxy-phenyl)-C19H14Cl2N203 A 389. 23 389. 6 ure ci OH H H N- (3, 5-Dichloro-2-hydroxy- 297. 14 297. 7 'o''phenyl)-3-phenyl-urea a OH CI N N,. O 3- [3- (3-Chloro-2-hydroxy-phenyl)- 49 I C12H15CLN204 A 286. 71 286. 9 49 ureidol-propionic acid ethyl ester OH 50 Cl w f 1-(3-Chloro-2-hydroxy-phenyl)-3-C12H17CIN202 A 256. 73 256. 9 l o pentyl-urea OH,,. oH i I 1-Benzyl-3- (3-chloro-2-hydroxy- 51 w C14H13C1N2o2 A 276. 72 276. 9 phenyl)-urea zozo OH Cl, i 1- (3-Chloro-2-hydroxy-phenyl)-3- C15Hl5CIN202A290. 74 290. 9 oh zozo OH 53 I 6N'y 1- (3-Chloro-2-hydroxy-phenyl)-3- phenethyl-urea oh OH 54 CI N N I n I/1- (3-Chloro-2-hydroxy-phenyl)-3- C 15H23C1N202 A 298. 81 299. 4 II T (l, 1, 3, 3-tetramethyl-butyl)-urea o I OH 55 NN 1-tert-Butyl-3- (3-chloro-2- CIIH15CIN202A242. 70 243. 0 C11H15CIN202 A 242. 70 243. 0 W ° hydroxy-phenyl)-urea OH 56 CI N N 1- (3-Chloro-2-hydroxy-phenyl)-3- C14H19CiN202 A 282. 77 283. 1 cyclohexylmethyl-urea zozo /caf3 OH H H 1- (3-Chloro-2-hydroxy-phenyl)-3- CI N NEZ C15H12C1F3N202 A 344. 72 345. 0 0 oh OH H H CI N N CI 1- (3-Chloro-2-hydroxy-phenyl)-3- c13H9C13N202 A 331. 59 331. 9 /o/ (3, 5-dichloro-phenyl)-urea a OH 59 'Y'YY lChloro-2-hydroxy-phenyl)-3-ci3H10CI2N202 A 297. 14 297. 7 OH ci OH H H 60 NN 1- (3-Chloro-2-hydroxy-phenyl)-3- C14HIOCIF3N202A330. 69 331. 0 W cr, (4-trifluoromethyl-phrnyl)-urea OH OH 61 NN_o 1- (3-Chloro-2-hydroxy-phenyl)-3- C13Hl7CIN202A268. 74 269. 1 ii I I cyclohexyl-urea OH OH H H 62 N N 1- (3-Chloro-2-hydroxy-phf,-nyl)-3- C14HIOCIF3N203A346. 69 346. 9 W ° uOCF3 (4-trifluoromethoxy-phenyl)-urea OCF3 OH 63 N N 1- (3-Chloro-2-hydroxy-phenyl)-3- 63 C14H10C1N302 A 287. 70 287. 9 W ° vCN (4-cyano-phenyl)-urea con OH 64 Cl\At H NH 1-Benzo [1, 3] dioxol-S-yl-3- (3- chloro-2-hydroxy-phenyl)-urea 0 0 OH CI N N 1- (3-Chloro-2-hydroxy-phenyl)-3- OH ! 65''YTYS -2-hydroxy-phenyl)-3-ci4H13CIN202 A 276. 72 276. 9 o-tolyl-urea /o i OH 66 N N Me 1- (3-Chloro-2-hydroxy-phenyl)-3- C14Hl3CIN203 A 292. 72 292. 9 0 (3-methoxy-phenyl)-urea Oh OU 67 ci N 1- (3-Chloro-2-hydroxy-phenyl)-3- C15Hl5CIN202 A 290. 75 290. 9 II (2, 6-dimethyl-phenyl)-urea i o r OH H H CI N N OMe 1- (3-Chloro-2-hydroxy-phenyl)-3- C16H17C1N205 A 352. 77 353. 2 | OMe | (3, 4, 5-trimethoxy-phenyl)-urea OMe OH H Hz 69 H H 1- (3-Chloro-2-hydroxy-phenyl)-3- naphthalen-1-yl-urea o w oH H l-Adamantan-1-yl-3- (3-chloro-2- C17H21CIN202 A 320. 82 321. 4 Cl/N'NH hydroxy-phenyl)-urea ! tu 0 OH CI/N N /1- (3-Chloro-2-hydroxy-phenyl)-3- C19H15C1N203 A 354. 79 354. 9 WJJ ° uOJU (4-phenoxy-phenyl)-urea 0 OH CI N N 1- (3-Chloro-2-hydroxy-phenyl)-3- II \ phenyl-urea C13H11C1N202 A 262. 70 263. 2 ! ! phenyl-urea 0 OH 73 F N N O 3- 3- (3-Fluoro-2-hydroxy-phenyl)- W ° o ureido]-propionic acid ethyl ester r o o OH 74 F-_6N 1- (3-Fluoro-2-hydroxy-phenyl)-3- C12Hl7FN202 A 240. 27 240. 5 pentyl-urea OH F-_ N N I-Benzyl-3- (3-fluoro-2-hydroxy- phenyl)-urea C14H13FN202 A 260. 26 260. 8 r o OH N N/I OH \Wt OH"T) 76 FlN N 1- (3-Fluoro-2-hydroxy-phenyl)-3- C15Hl5FN202 A 274. 29 274. 9 (2-methyl-benzyl)-urea zozo OH 77 F^s4 N N < 1-(3-Fluoro-2-hydroxy-phenyl)-3-C 1 SH15FN202 A 274. 29 274. 6 II II I phenethyl-urea i o OH F N N I n I/1- (3-Fluoro-2-hydroxy-phenyl)-3- C15H23FN202 A 282. 35 282. 9 (1, 1, 3, 3-tetramethyl-butyl)-urea OH Ho 0 hydroxy-phenyl)-urea OH OU F N N I- (3-Fluoro-2-hydroxy-phenyl)-3- C14H19FN202 A 266. 31 266. 7 cyclohexylmethyl-urea r o OH/CF3 F N N 1- (3-Fluoro-2-hydroxy-phenyl)-3- 81 C15H12F4N202 A 328. 26 328. 4 OH oh OH H H 0 (3, 5-dichloro-phenyl)-urea Oh ho OH OH F N N 1- (3-Fluoro-2-hydroxy-phenyl)-3- C13H10CiFN202 A 280. 68 281. 1 , o , (4-chloro-phenyl)-urea. ci ci F N N 1- (3-Fluoro-2-hydroxy-phenyl)-3- OH cl I caf9 OH Nrv 1- (3-Fluoro-2-hydroxy-phenyl)-3- C13H17FN202 A 252. 28 252. 6 cyclohexyl-urea OH H H Fu"4gN H a 1-(3-Fluoro-2-hydroxy-phenyl)-3-C14H10FF3N203 A 330. 23 330. 5 86 (4-trifluoromethoxy-phenyl)-urea OCF3 OH F N N 1- (3-Fluoro-2-hydroxy-phenyl)-3- C14H10FFN303 A 271. 25 271. 4 II II I (4-cyano-phenyl)-urea ZON OH F N N Q 1-Benzo [l, 3] dioxol-5-yl-3- (3- 88 C14H11FN204 A 290. 25 290. 7 ( !) !)/ftuoro-2-hydroxy-phenyl)-urea _ OH OH. 89 Fl : N N 1 C14Hl3FN202 A 260. 26 260. 5 o-tolyl-urea OH 90 F\/E N N < ZOMe 1-(3-Fluoro-2-hydroxy-phenyl)-3-C14H13FN203 A 276. 26 276. 5 W ° W (3-methoxy-phenyl)-urea r o i OH 91 F-_6N 1- (3-Fluoro-2-hydroxy-phenyl)-3- C15Hl5FN202A274. 29 274. 7 91 X (2, 6-dimethyl-phenyl)-urea v ° v OH H H F N N OMe 92 1- (3-Fluoro-2-hydroxy-phenyl)-3- C16H17FN205 A 336. 31 336. 6 9 ° (3, 4, 5-trimethoxy-phenyl)-urea OMe Oh F N N 1- (3-Fluoro-2-hydroxy-phenyl)-3- 93 C17H13FN202 A 296. 3 296. 6 V T naphthalen-1-yl-urea w ° w 94 OH \1V l-Adamantan-1-yl-3-(3-fluoro-2-C17H21FN202 A 304. 36 304. 6 F*\03/N) (NH hydroxy-phenyl)-urea o ' o OH 95 F/Nu N , 1- (3-Fluoro-2-hydroxy-phenyl)-3- C19Hi5FN203 A 338. 33 338. 6 U ° uoH (4-phenoxy-phenyl)-urea 0 OH 96 1 1-z phenyl-urea C13HllFN202 A 246. 24 246. 5 r o OH OH N N" 3- [3- (3, 5-Dichloro-2-hydroxy-4- 97 | methyl-phenyl)-ureido]-propionic C13H16C12N204 A 335. 19 335. 9 acid ethyl ester cl OH H H CI N N 1- (3, 5-Dichloro-2-hydroxy-4- C13H18C12N202 A 305. 20 305. 9 a methyl-phenyl)-3-pentyl-urea cl OH H Hs 99 C I NN \ 1-Benzyl-3- (3, 5-dichloro-2- C15H14C12N202 A 325. 19 325. 5 /9 hydroxy-4-methyl-phenyl)-urea cl OH Cl NH HN < 1-(3, 5-Dichloro-2-hydroxy-4- 100 Al lz T methyl-phenyl)-3-(2-methyl-C16H16C12N202 A 339. 22 339. 9 ° benzyl)-urea cl OH H H C1 N N 101 Cl), N N 1-(3, 5-Dichloro-2-hydroxy-4-C16H16C12N202 A 339. 22 339. 4 o methyl-phenyl)-3-phenethyl-urea cl OH CI N N I n I/1- (3, 5-Dichloro-2-hydroxy-4- 102 JL J o T) methyl-phenyl)-3- (l, l, 3, 3- C16H24CI2N202 A 347. 28 347. 4 tetramethyl-butyl)-urea cl OH ) H H CHYH* 0 hydroxy-4-methyl-phenyl)-urea OH Cri OH N N I-Cyclohexylmethyl-3- (3, 5- 104 !))"dichloro-2-hydroxy-4-methyl-C15H20C12N202 A 331. 24 332. 1 xfm phenyl)-urea ci Oti CF3 CI N N \ 1- (3, 5-Dichloro-2-hydroxy-4- 105 + Y methyl-phenyl)-3-(4-CI6H13C12F3N202 A 393. 19 393. 8 C trifluoromethyl-benzyl)-urea ci OH N NqCi 1- (3, 5-Dichloro-2-hydroxy-4- 106 0 methyl-phenyl)-3- (3, 5-dichloro- C14HIOC14N202 A 380. 06 380. 2 OH oh OH N N 1- (4-Chloro-phenyl)-3- (3, 5- 107 {dichloro-2-hydroxy-4-methyl-CI4HllC13N202 A 345. 61 345. 9 ci phenyl)-urea ci OH OH 1-(3, 5-Dichloro-2-hydroxy-4- 108 , , methyl-phenyl)-3- (4- C15H11CI2F3N202 A 379. 16 379. 9 /\j CF3 trifluoromethyl-phenyl)-urea o OH H H CI N N 109 1-Cyclohexyl-3- (3, 5-dichloro-2- C14H18C12N202 A 317. 21 317. 8 109/9 hydroxy-4-methyl-phenyl)-urea cl OH 1- (3, 5-Dichloro-2-hydroxy-4- 110 0 methyl-phenyl)-3- (4- C15HllCl2F3N203 A 395. 16 395. 4 ocF3 trifluoromethoxy-phenyl)-urea o OH H H OH 1-(4-Cyano-phenyl)-3- (3, 5- 111) ° < dichloro-2-hydroxy-4-methyl-C15HlIC12N302 A 336. 18 336. 4 T CN phenyl)-urea o OH H H NyN I-Benzo [1, 3] dioxol-5-yl-3- (3, 5- 112 0 dicldoro-2-hydroxy-4-methyl-C15Hl2Cl2N204 A 355. 18 355. 2 phenyl)-urea " ! OH H H 1- (3, 5-Dichloro-2-hydroxy-4- 113 methyl-phenyl)-3-o-tolyl-urea Cl C ! OH N N OMe 1- (3, 5-Dichloro-2-hydroxy4- methyl-phenyl)-3- (3-methoxy- C15Hl4Cl2N203 A 341. 19 341. 4 phenyl)-urea cl OH Cl oL N N 1-(3, 5-Dichloro-2-hydroxy-4- 115) o Xl methyl-phenyl)-3-(2, 6-dimethyl-C16HI6C12N202 A 339. 22 339. 4 phenyl)-urea cl OH N N-, qome 1- (3, 5-Dichloro-2-hydroxy-4- 116 0 methyl-phenyl)-3- (3, 4, 5- C17H18C12N205 A 401. 24 401. 3 /° \jOMe trimethoxy-phenyl)-urea Cl OMe OH Cl H 1- (3, 5-Dichloro-2-hydroxy-4- 117 T T T ! methyl-phenyl)-3-naphthalen-l-yl-C18H14C [2N202 A 361. 23 361. 3 C# urea cul OH 118 Cl, N NH l-Adamantan-1-yl-3-(3, 5-dichloro-C18H22C12N202 A 369. 29 369. 3 2-hydroxy-4-methyl-phenyl)-urea zozo ci OH CI 1- (3, 5-Dichloro-2-hydroxy-4- 119 tJL ! i f !) methyl-phenyl)-3- (4-phenoxy- C20H16CI2N203 A 403. 26 403. 3 phenyl)-urea oh OH OH H H CI N N 120 1- (3, 5-Dichloro-2-hydroxy-4- C14Hl2Cl2N202 A 311. 17 311. 3 o v methyl-phenyl)-3-phenyl-urea ci OH F N N O H N 3- [3- (5-Bromo-3-fluoro-2- 121 0 0 hydroxy-phenyl)-ureidol-propionic C12Hl4BrFN204 A 349. 15 349. 9 acid ethyl ester OH OU H H F N N 122 1- (5-Bromo-3-fluoro-2-hydroxy- C12H16BrFN202 A 319. 17 320. 0 0 phenyl)-3-pentyl-urea Br OH 123 F) NyN I-Benzyl-3- (5-bromo-3-fluoro-2- C14Hl2BrFN202A339. 16 340. 0 123 ' C14H12BrFN202 A 339. 16 340. 0 Br hydroxy-phenyl)-urea OH OU H H 124 F I N'N \ 1- (5-Bromo-3-fluoro-2-hydroxy- C15H14BrFN202 A 353. 19 353. 9 , o phenyl)-3- (2-methyl-benzyl)-urea Br OH HO F N N 125 1- (5-Bromo-3-fluoro-2-hydroxy- C15Hl4BrFN202A353. 19 353. 9 Br phenyl)-3-phenethyl-urea Br OH FlrNyN 1- (5-Bromo-3-fluoro-2-hydroxy- 126 0 phenyl)-3- (1, 1, 3, 3-tetramethyl- C15H22BrFN202 A 361. 25 362. 0 butyl)-urea er OU F N N 1-tert-Butyl-3- (5-bromo-3-fluoro- 127 2-h drox-hen 1-urea C11H14BrFN202 A 305. 14 305. 8 zu YP Y) ! OH HO F \ N N 1- (5-Bromo-3-fluoro-2-hydroxy- II C14H18BrFN202 A 345. 21 346. 1 o phenyl)-3-cyclohexylmethyl-urea Br OH OH f" ! N N 1- (5-Bromo-3-fluoro-2-hydroxy- 129 ! ! ! phenyl)-3- (4-triRuoromethyI- C15HllBrF4N202 A 407. 16 407. 8 t benzyl)-urea Br OH HO F Nu N CI 1- (5-Bromo-3-fluoro-2-hydroxy- 130 9 o 4 phenyl)-3-(3, 5-dichloro-phenyl)-C13H8BrCl2FN202 A 394. 02 394. 9 urea Br OH HO oh 'L o phenyl)-3- (4-chloro-phenyl)-urea Br OH HO FICN yN 1- (5-Bromo-3-fluoro-2-hydroxy- 132 0 phenyl)-3- (4-trifluorometfiyl- C14H9BrF4N202 A 393. 13 393. 9 T CF3 phenyl)-urea Br OH H H F N N 133 1- (5-Bromo-3-fluoro-2-hydroxy- C13H16BrFN202 A 331. 18 332. 0 0,-o phenyl)-3-cyclobexyl-urea Br OH F N N 1- (5-Bromo-3-fluoro-2-hydroxy- 134 1 phenyl)-3- (4-trifluoromethoxy- C14H9BrF4N203 A 409. 13 409. 8 ocF3 phenyl)-urea OH OH H H F N N 135 N N l-(S-Bromo-3-fluoro-2-hydroxy-C14H9BrFN302 A 350. 14 350. 9 0l>CN phenyl)-3- (4-cyano-phenyl)-urea Br OH OH NyN,,. il 1-Benzo [1, 3] dioxol-5-yl-3- (5- 136 FoßH N O> bromo-3-Suoro-2-hydroxy-C14HlOBrFN204 A 369. 14 369. 7 g phenyl)-urea OH OH H H F N N + Y ß l-(S-Bromo-3-fluoro-2-hydroxy-C14H12BrFN202 A 339. 16 339. 8 57 L 9 phenyl)-3-o-tolyl-urea Br E OH H H F N N OMe 1-(5-Bromo-3-fluoro-2-hydroxy- 138 e Y < phenyl)-3-(3-methoxy-phenyl)-C14H12BrFN203 A 355. 16 355. 5 urea OH On H H F N N 1- (5-Bromo-3-fluoro-2-hydroxy- 139 LW T X phenyl)-3-(2, 6-dimethyl-phenyl)-C15H14BrE202 A 353. 19 353. 6 urea Br OH H H F N N OMe 1- (5-Bromo-3-fluoro-2-hydroxy- 140 0 phenyl)-3- (3, 4, 5-tfimethoxy- C16Hl7BrFN205A415. 21 415. 6 OMe phenyl)-urea Br OMe OH H H 141 F/N N/1- (5-Bromo-3-fluoro-2-hydroxy- phenyl)-3-naphthalen-1-yl-urea Br Oh 142 F, 2s N NH l-Adamantan-l-yl-3-(5-Brorno-3-C17H20BrFN202 A 383. 26 383. 7 fluoro-2-hydroxy-phenyl)-urea zozo Br OH H H OH 1-(S-Bromo-3-fluoro-2-hydroxy- 143 qJJ ° aoJ 3 phenyl)-3-(4-phenoxy-phenyl)-C19H14BrFN203 A 417. 23 417. 6 olim urrea Br OH H H F) N y N phenyl)-3-phenyl-urea Cl3HlOBrFN202 A 325. 13 325. 7 Br OH H H 3- [3- (3, 5-Difluoro-2-hydroxy- 145 Ft, N H pheñyl)-ureido]-propiomc acid C12H14F2N204 A 288. 25 288. 9 F 0 0 ethyl ester OH H H 146 F N I C12Hl6F2N202 A 258. 26 258. 9 phenyl)-3-pentyl-urea Oh Oh 147 1-Benzyl-3- (3 5-difluoro-2- ! ! hydroxy-phenyi)-urea Oh /O OH 148 H, ) OI 1- (3, 5-Difluoro-2-hydroxy- phenyl)-3- (2-methyl-benzyl)-urea /o F OH H H r 149 F N'N I j phenylD phenethyl-n ea C15H14F2N202 A 292_28 292. 9 oh _ OU F w0 N N | l 1-(3, 5-Difluoro-2-hydroxy- phenyl)-3- (1, 1, 3, 3-tetramethyl-C15H22F2N202 A 300. 34 300. 5 butyl)-urea OH 151 F N N 1-tert-Butyl-3- (3, 5-difluoro-2- C11H14F2N202 A 244. 24 244. 3 52 | F tzNH NO |-(3, 5-Difluoro 2 hydroxy | C14H1SF211202 | | 284. 30 | 284. 6 hydroxy-phenyl)-urea F OHM 152 F N,. N 1- (3, 5-Difluoro-2-hydroxy- F- ° phenyl)-3-cyclohexylmethyl-urea /O Caf3 OH H H \ 1- (3, 5-Difluoro-2-hydroxy- 153 phenyl)-3- (4-trifluoromethyl- C15HI IF5N202A346. 25 346. 5 Fw benzyl)-urea OH. F N N CI 1- (3, 5-Difluoro-2-hydroxy- 154 y phenyl)-3- (3, 5-dichloro-phenyl)- C13H8Cl2F2N202A333. 12 333. 3 urea ci OH 155 F N N 1- (3, 5-Difluoro-2-hydroxy- C13H9C1F2N202 A 298. 67 298. 9 y phenyl)-3- (4-chloro-phenyl)-urea Oh OH F N N - (3, 5-Difluoro-2-hydroxy- 156 t yN phenyl)-3- (4-trifluoromethyl- C14H9F5N202A332. 23 332. 7 cF phenyl)-urea oh OH 157 FX Y 1-(3, 5-Difluoro-2-hydroxy-C13H16F2N202 A 270. 28 270. 7 phenyl)-3-cyclohexyl-urea FRO OH HH 1- (3, 5-Difluoro-2-hydroxy- 158 I I phenyl)-3- (4-trifluoromethoxy- C14H9F2F3N203 A 348. 22 348. 6 Fw WOCF3 phenyl)-urea oh OH 159 F N N 1- (3, 5-Difluoro-2-hydroxy- C14H9F2N302 A 289. 24 289. 5 )"i phenyl)-3- (4-cyano-phenyl)-urea Oh OH NyN, 0I-Benzo [1, 3] dioxol-5-yl-3- (3, 5- , o , > difluoro-2-hydroxy-phenyl)-urea F OH 161 F N N 1- (3, 5-Difluoro-2-hydroxy- phenyl)-3-o-tolyl-urea C14H12F2N202 A 278. 25 278. 6 0 OH H H 1- (3, 5-Difluoro-2-hydroxy- 162 < T t phenyl)-3-(3-methoxy-phenyl)-C14H12F2N203 A 294. 25 294. 5 urea OH H H 1- (3, 5-Difluoro-2-hydroxy- 163 Fv ° X phenyl)-3-(2, 6-dimethyl-phenyl)-ClSH14F2N202 A 292. 28 292. 6 11 o i urea OH H H F N Nqome 1- (3, 5-Difluoro-2-hydroxy- 164 | phenyl)-3-(3, 4, 5-trimethoxy- C16H17F2N205 A 354. 31 354. 6 F OMe phenyl)-urea OMe OH 165 F, N N 1- (3, 5-Difluoro-2-hydroxy- C17H12F2N202 A 314. 29 314. 6 phenyl)-3-naphthalen-1-yl-urea F 166 fH 1-Adamantan-l-yl-3-(3, 5-difluoro-C17H20F2N202 A 322. 35 322 7 Foc N NH 2-hydroxy-phenyl)-urea F w I p'o t OH OH H 1- (3, 5-Difluoro-2-hydroxy- 167 F i I NN I i I phenyl)-3- (4-phenoxy-phenyl)- C19H14F2N203 A 356. 32 356. 6 urea OH H H 168 FW T < 1-(3, 5-Difluoro-2-hydroxy-C13HlOF2N202 A 264. 23 264. 7 II phenyl)-3-phenyl-urea F 0 OH OH H H Ny 3-f 3- [5-Chloro-2-hydroxy-3- (I- 169 0 0 hydroxy-ethyl)-phenyl]-urcidol-C14Hl9CIN205 A 330. 76 331. 1 propionic acid ethyl ester OH OH OH OH N 1- [5-Chloro-2-hydroxy-3- (l- 170 J S hydroxy-ethyl)-phenyl]-3-pentyl-C14H21C1N203 A 300. 78 301. 2 urea ci OH OU H H 1- [5-Chloro-2-hydroxy-3- (l- 171 ! i"hydroxy-ethyl)-phenyl]-3-pentyl-C16H17C1N203 A 320. 77 321. 0 urgea ci OH Oh N N \ 1- [5-Chloro-2-hydroxy-3- (1- 172 + Y hydroxy-ethyl)-phenyl]-3-(2-C17H19CIN203 A 334. 80 335. 1 ° methyl-benzyl)-urea C ! OH OH H H N N 1- [5-Chloro-2-hydroxy-3- (1- 173 t xJ o ~ hydroxy-ethyl)-phenyl]-3-C17H19CIN203 A 334. 80 335. 3 phenethyl-urea OH OH OH OH Ny N 1- [5-Chloro-2-hydroxy-3- (l- 174 0 hydroxy-ethyl)-phenyl]-3- (1, 1, 3, 3- C17H27C12N202 A 342. 86 343. 7 tetramethyl-butyl)-urea ci OH OH NyN, N 1-tert-Butyl-3- [5-chloro-2- 175 t j o hydroxy-3-(1-hydroxy-ethyl)-C13H19CIN203 A 286. 75 287. 6 phenyl]-urea ci OH OU Ny N 1- [5-Chloro-2-hydroxy-3- (I- 176 0 O hydroxy-ethyl)-phenyl]-3-C16H23CIN203 A 326. 82 327. 5 ° cyclohexylmethyl-urea ci OH OH/I CF3 N N 1- [5-Chloro-2-hydroxy-3- (1- 177 + o hydroxy-ethyl)-phenyl]-3-(4-C17H16CIF3N203 A 388. 77 389. 4 rl trifluoromethyl-benzyl)-urea Ci OH OH N N CI N ci 1- [5-Chloro-2-hydroxy-3- (l- 178 y hydroxy-ethyl)-phenyl]-3- (4- C15Hl3Cl3N203 A 375. 63 376. 2 chloro-phenyl)-urea Cl Cl OH OH N 1- [5-Chloro-2-hydroxy-3- (l- 179 J E Y JL hydroxy-ethyl)-phenyl]-3- (4- C15H14C12N203 A 341. 19 341. 6 ci chloro-phenyl)-urea cl OH OH H H 1- [5-Chloro-2-hydroxy-3- (l- 180 hydroxy-ethyl)-phenyll-3- (4- C16Hl4CIF3N203 A 374. 74 375. 0 cF3 trifluoromethyl-phenyl)-urea cl OH OH H H NyN, o 1- [5-Chloro-2-hydroxy-3- (l- 181 hydroxy-ethyl)-phenyl]-3-C15H21CIN203 A 312. 79 313. 0 cyclohexyl-urea cl OH OH H H Ny NNao 1- [5-Chloro-2-hydroxy-3- (I- 182 Tl T) hydroxy-ethyl)-phenyl]-3-(4-CI6H14CIF3N204 A 390. 74 391. 2 ocF3 trifluoromethoxy-phenyl)-urea ci OH OH H H FIYH-Chlofo-2-hydfoxy-3- (I- 183 0 hydroxy-ethyl)-phenyll-3- (4- C16Hl4CIN303 A 331. 75 332. 0 T CN cyano-phenyl)-urea cl OH OH H H AN N>/< O 1-Benzo [1, 3] dioxol-5-yl-3- [5- 184 ! chloro-2-hydroxy-3- (1-hydroxy- C16H15C1N205 A 350. 75 351. 1 ethyl)-phenyl]-urea ci OH OH H H N y N 1- [5-Chloro-2-hydroxy-3- (I- 185 9 < W hydroxy-ethyl)-phenyl]-3-o-tolyl-C16H17CIN203 A 320. 77 321. 0 urea o OH OH H H NyN'Ome 1- [5-Chloro-2-hydroxy-3- (I- 186 0 hydroxy-ethyl)-phenylj-3- (3- A 336. 77 337. 1 methoxy-phenyl)-urea cul OH OH H H NyN) 1- [5-Chloro-2-hydroxy-3- (l- 187 11 1 o ll 1 hydroxy-ethyl)-phenyl]-3-(2, 6-C17H19CIN203 A 334. 80 335. 2 dimethyl-phenyl)-urea ci OH OH H H NyN,, qOMe 1- [5-Chloro-2-hydroxy-3- (l- 188 0 hydroxy-ethyl)-phenyl]-3- (3, 4, 5- C18H21C1N206 A 396. 82 397. 2 'oMe trimethoxy-phenyl)-urea ci oye OH OH NyN 1- [5-Chloro-2-hydroxy-3- (I- 189 r Z hydroxy-ethyl)-phenyl]-3-C19H17CIN203 A 356. 80 357. 1 naphthalen-1-yl-urea ci OH OH H 1-Adamantan-1-yl-3- [5-chloro-2- 190 N NH hydroxy-3- (I-hydroxy-ethyl)- C19H25CIN203 A 364. 87 365. 1 or phenyl]-urea cl OH OH H H N N 1- [5-Chloro-2-hydroxy-3- (I- 191 1 0 o <> hydroxy-ethyl)-phenyl]-3-(4-C21H19CIN204 A 398. 84 399. 0 o phenoxy-phenyl)-urea o OH OH Ny N-0 1- [5-Chloro-2-hydroxy-3- (l- 192 J 6 J hydroxy-ethyl)-phenyl]-3-phenyl-C15H15CIN203 A 306. 74 307. 0 urea cl OH H H 1_ (5-Chloro-2-hydroxy-phenyl)-3- 193 VH pentyl-thiourea C12H17CiN20S I 272. 79 272. 9 ci OH Cl pentyl-thuourea OH H H 194 C14H13C1N20S I 292. 78 293. 1 s phenyl)-thiourea ci OH H H 195 Y'" H5-CMoro-2-hydroxy-phenyl)-3-ci5H150N20S I 306. 81 306. 9 ta s (2-methyl-benzyl)-thiourea OH OH H H 1- (5-Chloro-2-hydroxy-phenyl)-3- < phenethyl-thiourea cl OH N N 1- (5-Chloro-2-hydroxy-phenyl)-3- 197 s (1, 1, 3, 3-tetramethyl-butyl)-C15H23ClN20S I 314. 87 315. 0 thiourea cul OH N N 198 fY'TY l-tert-Butyl-3- (5-cMoro-2- C11H15C1N20S I 258. 77 258. 9 t hydroxy-phenyl)-thiourea Ci OH ! H H 199 lS T 1/1 (5 Chloro-2-hydroxy-phenyl)-3-ClOH13CIN20S I 244. 74 245. 0 l ' s'isopropyl-thiourea ci OH H H 200 S f 1-(5-Chloro-2-hydroxy-phenyl)-3-C14H19CIN20S I 298. 83 299. 1 cl cyclohex ylmethyl-thiourea OH CF3 OH f" ! H 1- (5-Chloro-2-hydroxy-phenyl)-3- 201 fl r Af (4-trifluoromethyl-benzyl)-C15H12ClF3N20S I 360. 78 361. 1 thiourea Ci OH H H N N C 1- (5-Chloro-2-hydroxy-phenyl)-3- Y s Y (3, 5-dichloro-phenyl)-thiourea ci OH H H 203 1- (5-Chloro-2-hydroxy-phenyl)-3- C13HlOCl2N20S 1 313. 20 313. 5 '-- s' (4-chloro-phenyl)-thiourea cl OH H H N N 1- (5-Chloro-2-hydroxy-phenyl)-3- 204 (4-trifluoromethyl-phenyl)-C14HIOCIF3N20S 1 346. 76 347. 0 c3 thiourea cl OH H H 1- (5-Chloro-2-hydroxy-phenyl)-3- s cyclohexyl-thiourea cl OH COG ) D) J t N N 1- (5-Chloro-2-hydroxy-phenyl)-3- 206 J 5'L J (2-tnf ! uoromethyl-phenyl)- C14HloaF3N20S I 346. 76 347. 0 thiourea cl OH H H N N 1- (5-Chloro-2-hydroxy-phenyl)-3- 207 f 1- (5-Chloro-2-hydroxy-phenyl)-3- C13HIlCIN20S 1 278. 76 279. 0 t ci Y OH H H CI N N 208 1- (3, 5-Dichloro-2-hydroxy- C12Hl6Cl2N20S 1 307. 24 307. 5 cl phenyl)-3-pentyl-thlourea cl OH CI N N 1_genz 1-3- (3, 5-dichloro-2-, 209 Clap'NN y C14H12C12N20S I 327. 23 327. 4 s hydroxy-phenyl)-thiourea ci OH -1 H Cl N N<3 1-(3, 5-Dichloro-2-hydroxy- 210 s phenyl)-3- (2-methyl-benzyl)- C15Hl4Cl2N20S 1 341. 26 341. 4 thiourea o OH H H CI N N \ 1- (3, 5-Dichloro-2-hydroxy- phenyl)-3-phenethyl-thiourea cl a OH N N 1- (3, 5-Dichloro-2-hydroxy- 212 s phenyl)-3- (1, 1, 3, 3-tetamethyl-ClSH22Cl2N20S I 349. 32 349. 6 butyl)-thiourea cl OH CI N N 213 'YYY l-tert-Butyl-3- (3dicMoro-2- C11H14CL2N20S I 293. 21 293. 6 hydroxy-phenyl)-thiourea cl OH H H CI N N 214''Yj'Y l- (5-CMo2-hydroxy-phenyl)-3- ciOH12C12N20S I 279. 19 279. 5 isopropyl-thiourea C ! OH CI N N 1- (3, 5-Dichloro-2-hydroxy- 215 Tl I T phenyl)-3-cyclohexylmethyl-C14H18C12N20S I 333. 28 333. 5 thiourea cl OH/I CF3 CI N N 1- (3, 5-Dichloro-2-hydroxy- 216 y phenyl)-3- (4-trifluoromethyl- C15HIIC12F3N20S1395. 23 395. 5 benzyl)-thiourea cl OH H H CI N N CI 1- (3, 5-Dichloro-2-hydroxy- 217 y phenyl)-3- (3, 5-dichloro-phenyl)- C13H8Cl4N20S1382. 09 382. 3 thiourea ci OH H H CI N N 1- (3, 5-Dichloro-2-hydroxy- 218 s phenyl)-3- (4-chloro-phenyl)- C13H9Cl3N20S 1 345. 65 345. 9 ci thiourea C ! OH H H CI N N 1- (3, 5-Dichloro-2-hydroxy- Y J s JL phenyl)-3- (4-tniluoromethyl- C14H9C12F3N20S I 381. 2 381. 6 s CF ; 3 phenyl)-thiourea ci OH H H CI N N 1- (3, 5-Dichloro-2-hydroxy- C13H16C12N20S I 319. 25 319. 6 s phenyl)-3-cyclohexyl-thiourea ci OH CFS H H N N 1- (3, 5-Dichloro-2-hydroxy- 221 s phenyl)-3- (2-trifluoromethyl- C14H9Cl2F3N20S 1 381. 20 381. 4 phenyl)-thiourea cl OH H H CI N N 222 1- (3, 5-Dichloro-2-hydroxy- C13141OC12N20S 1 313. 20 313. 5 phenyl)-3 phenyl-thiourea Ci OH 223 N 1- (3-Chloro-2-hydroxy-phenyl)-3- C12Hl7CIN20S 1 272. 79 273. 2 pentyl-thiourea i s OH ¢ NN/t3 1-Benzyl-3 (3-ch oro 2 hydroxy-1 292. 78 293. 1 oh Oh 225 C N N 1- (3-Chloro-2-hydroxy-phenyl)-3- 225 c. . M HkJ) l (3-Chloro-2-hydroxy-phenyl)-3- ci5H15C ! N20S I 306. 81 307. 0 L (2-methyl-benzyl)-thiourea C15H15CiN20S I 306. 81 307. 0 s OH 226 CI N N 1- (3-Chloro-2-hydroxy-phenyl)-3- C15H15C1N20S I 306. 81 307. 1 N phenethyl-thiourea /s/ oh OH 227 N N (1, 1, 3, 3-tetramethyl-butyl)- C15H23C1N20S I 314. 87 315. 2 OH thiourea OH 228 N N 1-tert-Butyl-3- (3-Chloro-2- CIIH15ClN20S1 258. 77 259. 0 hydroxy-phenyl)-thiourea OH Cl, &H H 229 YY l- (3-CMoro-2-hydroxy-phenyl)-3- ciOH13CIN20S I 244. 74 244. 9 isopropyl-thiourea OH OH Ny N 1- (3-Chloro-2-hydroxy-phenyl)-3-'IN20S h ! cyclohexylmethyl-ttuourea 230 cyclohexylmethyl-thiourea C14Hl9C 1 298. 83 299. 3 IFS OH H H 1- (3-Chloro-2-hydroxy-phenyl)-3- 231 NYN (4-trifluoromethyl-benzyl)-C15Hl2CIF3N20S 1 360. 78 361. 1 361. 1 s OH H 232 J /1- (3-Chloro-2-hydroxy-phenyl)-3- C13H9C13N20S I 347. 65 348. 0 (3, 5-dichloro-phenyl)-thiourea Ci OH 233 N N 1- (3-Chloro-2-hydroxy-phenyl)-3- 233 C13H10C12N20S I 313. 20 313. 5 OH cl OH | H H 1-(3-Chloro-2-hydroxy-phenyl)-3- 234 (4-trifluoromethyl-phenyl)-C14Hi0CIF3N20S I 346. 76 347. 2 CF3 thiourea OH OH 235 N N 1- (3-Chloro-2-hydroxy-phenyl)-3- c13H17CIN20S I 284. 8 285. 1 I I cyclohexyl-thiourea U OH H H 1- (3-Chloro-2-hydroxy-phenyl)-3- 236 a\NN> (2-bifluoromethyl-phenyl)-C14HlOCIF3N20S I 346. 76 347. 2 s thiourea OH 237 CI N N 1- (3-Chloro-2-hydroxy-phenyl)-3- C13H11C1N20S I 278. 76 279. 0 phenyl-thiourea OH 238 N 1- (3-Fluoro-2-hydroxy-phenyl)-3- C12Hl7FN20S 1 256. 34 256. 8 pentyl-thiourea oh/ OH [ OH HYH ; r" 1-Benzyl-3- (3-fluoro-2-hydroxy- phenyl)-thiourea C14H13FN20S I 276. 33 276. 7 s OH 240 F N N 1- (3-Fluoro-2-hydroxy-phenyl)-3- C15Hi5FN20S I 290. 36 290. 5 (2-methyl-benzyl)-thiourea OH OU 241 y N,, _o 1- (3-Fluoro-2-hydroxy-phenyl)-3- (II phenethyl-thiourea s OH OH H''1- (3-Fluoro-2-hydroxy-phenyl)-3- n n 242 F-_&N N (1, 1, 3, 3-tetramethyl-butyl)- C15H23FN20S I 298. 42 298. 7 9 s thiourea OH 243 F/4 N N/1-tert-Butyl-3-(3-fluoro-2- s hydroxy-phenyl)-thiourea i s OH N N 1- (3-F'luoro-2-hydroxy-phenyl)-3- C1oH13FN20S I 228. 29 228. 5 s isopropyl-thiourea OH 245 F N N 1- (3-Fluoro-2-hydroxy-phenyl)-3- C14H19 2- cyclohexylmethyl-thiourea s OH H lt 1-(3-Fluoro-2-hydroxy-phenyl)-3- F-_6N N (4-trifluoromethyl-benzyl)-C15Hl2F4N20S 1 344. 33 344. 7 thiourea i s OH Ho 247 1- (3-Fluoro-2-hydroxy-phenyl)-3- C13H9C12FN2os I 331. 19 331. 5 s (3, 5-dichloro-phenyl)-thiourea Cl OH HO 248 F N N 1- (3-Fluoro-2-hydroxy-phenyl)-3- C13H10C1FN20S I ( (4-chloro-phenyl)-thiourea ci OH F N N 1- (3-Fluoro-2-hydroxy-phenyl)-3- 249 y (4-trifluorometllyl-phenyl)-C14HIOF4N20S 1 330. 30 330. 6 9 WCF3 thiourea Crg OH 250 F N N 1- (3-Fluoro-2-hydroxy-phenyl)-3- C13H17FN20S I 268. 35 268. 6 cyclohexyl-thiourea \ s' H H 3 1-(3-Fluoro-2-hydroxy-phenyl)-3- 251 F) (N N (2-trifluoromethyl-phenyl)-C14HIOF4N20S 1 330. 30 330. 5 thiourea OH F_, [ : NYN, o 1- (3-Fluoro-2-hydroxy-phenyl)-3- phenyl-thiourea s OH ! H H 253 1- (3, 5-Dichloro-2-hydroxy-4- C13H18C12N20S I 321. 27 321. 8 i S methyl-phenyl)-3-pentyl-thiourea ci OU Cl N N JS 1-Benzyl-3-(3, 5-dichloro-2- 254 hydroxy-4-methyl-phenyl)-C15Hl4Cl2N20S 1 341. 26 341. 5 thiourea Ci OU/ Ny N 1- (3, 5-Dichloro-2-hydroxy-4- 255 < Y methyl-phenyl)-3-(2-methyl-C16H16Cl2N20S I 355. 28 355. 6 benzyl)-thiourea cl OH OH 1-(3, 5-Dichloro-2-hydroxy-4- 256 ATJ s < methyl-phenyl)-3-phenethyl-C16H16Cl2N20S I 355 28 355. 6 thiourea ci OH H H N N 1- (3, 5-Dichloro-2-hydroxy-4- , S methyl-phenyl)-3- (1, 1, 3, 3- C16H24C12N20S I 363. 35 363. 6 tetramethyl-butyl)-thiourea ci OH CI N N 1-tert-Butyl-3- (3, 5-dichloro-2- 258 j ! J"'hydroxy-4-methyt-phenyl)-C12H16C12N20S I 307. 24 307. 5 thiourea 307. 5 ci OH H H 259 y'-r 1- (5-CWoro-2-hydroxy-4-methyl- phenyl)-3-isopropyl-thiourea ci OH CI N N 1- (3, 5-Dichloro-2-hydroxy-4- 260 Y J"methyl-phenyl)-3-C15H20C12N20S I 347. 30 347. 5 cyclohexylmethyl-thiourea cl Cl Non 1- (3, 5-Dichloro-2-hydroxy-4- 261 I methyl-phenyl)-3- (4- C16H13C12F3N20S I 409. 25 409. 5 trifluoromethyl-benzyl)-thiourea cl OH N ci 1- (3, 5-Dichloro-2-hydroxy-4- 262 11, 1 Y v methyl-phenyl)-3-(3, 5-dichloro-C14HlOC14N20S I 396. 12 396. 3 phenyl)-thiourea ci ci OH N N 1- (3, 5-Dichloro-2-hydroxy-4- 263 4 l methyl-phenyl)-3-(4-chloro-C14H1 lCl3N20S I 361. 67 361. 9 1'phenyl)-thiourea ci OH NYN,, A 1- (3, 5-Dichloro-2-hydroxy-4- 264 methyl-phenyl)-3- (4- C15HllCl2F3N20S 1 395. 23 395. 7 1' CFS trifluoromethyl-phenyl)-thiourea ci OH NyN, o 1- (3, 5-Dichloro-2-hydroxy-4- 265 s methyl-phenyl)-3-cyclohexyl-C14Hl8Cl2N20S 1 333. 28 333. 8 thiourea ci OH CF3 OH COG t LI LJ ! Ny N 1- (3, 5-Dichloro-2-hydroxy-4- 266 JL methyl-phenyl)-3-(2-ClSHllCI2F3N20S I 395. 23 395. 8 ot trifluoromethyl-phenyl)-thiourea ci OH CI I N N I \ 267 N 1- (3, 5-Dichloro-2-hydroxy-4- C14Hl2Cl2N20S1327. 23 327. 7 i S methyl-phenyl)-3-phenyl-thiourea ci OH F I N N 268 1- (5-Bromo-3-fluoro-2-hydroxy- c12H16BrFN20S I 335. 24 335. 8 s phenyl)-3-pentyl-tWourea Br OH H H 269 N N \ 1-Benzyl-3- (5-bromo-3-fluoro-2- Br Ber OH OH/ F N N 1- (5-Bromo-3-fluoro-2-hydroxy- 270 Y J T phenyl)-3- (2-methyl-benzyl)- C15H14BrFN20S I 369. 25 369. 5 -thiourea Br OH F I N N 271 1- (5-Bromo-3-fluoro-2-hydroxy- C15Hl4BrFN20S1369. 25 369. 5 i phenyl)-3-phenethyl-thiourea C15H14BrFN20S I 369. 25 369. 5 Br OH F) N'rN 1- (5-Bromo-3-fluoro-2-hydroxy- 272 s phenyl)-3- (1, 1, 3, 3-tetramethyl- C15H22BrFN20S I 377. 32 377. 5 butyl)-thiourea Br OH tuf ho F N N 273 1 1-tert-Butyl-3- (5-bromo-3-fluoro- 321. 21 321. 5 2-hydroxy-phenyl)-thiourea Br OH H H N N L n 9 I (s Bromo-3-fluoro-2-hydroxy-ClOHl2B I 307. 19 307. 4 phenyl)-3-isopropyl-thiourea Br OH FI NH N N 1- (5-Bromo-3-fluoro-2-hydroxy- 275 phenyl)-3-cyclohexylmethyl-C14Hl8BrFN20S 1 361. 28 361. 5 -thiourea Br OH CF3 H H 1- (5-Bromo-3-fluoro-2-hydroxy- 276 + t phenyl)-3-(4-trifluoromethyl-C15H1 lBrF4N20S I 423. 23 423. 5 s benzyl)-thiourea Br OH F-, N ci 1- (5-Bromo-3-fluoro-2-hydroxy- 77 | phenyl) 3 (3, 5-dichloro-phenyl)- C13H8BrCl2FN20S1410. 09 410. 5 -thiourea Br cl OH 1- (5-Bromo-3-fluoro-2-hydroxy- , J , phenyl)-3- (4-chloro-phenyl)- C13H9BrCIFN20S I 375. 65 375. 9 cl thiourea Br OH F 4 N N 1-(5-Bromo-3-fluoro-2-hydroxy- 279 y phenyl)-3- (4-trifluoromethyl- C14H9BrF4N20S1409. 20 409. 5 T CF3 phenyl)-thiourea Br OH F N N 280 Ny'-o 1- (5-Bromo-3-fluoro-2-hydroxy- C13H16BrFN20S I 347. 25 347. 6 t phenyl)-3-cyclohexyl-thiourea Br OH CFS 1- (5-Bromo-3-fluoro-2-hydroxy- 281 | phenyl)-3-(2-trifluoromethyl-C14H9BrF4N20S I 409. 20 409. 5 phenyl)-thiourea Br I I OH ! H H F) N N s phenyl)-3-phenyl-thiourea Br OH H H 283 F N N 1- (3, 4-Difluoro-2-hydroxy- C12H16F2N20S I 274. 33 274. 8 s phenyl)-3-pentyl-thiourea OU Oh 284 F N N 1-Benzyl-3- (3, 4-difluoro-2- 14 hydroxy-phenyl)-thiourea F OH H H/ 1- (3, 4-Difluoro-2-hydroxy- 285 F N N phenyl)-3- (2-methyl-benzyl)- C15Hl4F2N20S1 308. 35 308. 6 Fw S thiourea OH H H 286 F N N 1- (3, 4-Difluoro-2-hydroxy- C15H14F2N20S I 308. 35 308. 6 OH l F s OH | H H 1-(3, 4-Difluoro-2-hydroxy- « | phenyl)-3- (1, 1, 3, 3-tetramethyl- C15H22F2N20S I 316. 41 316. 8 F s butyl)-thiourea OH 288 N N 1-tert-Butyl-3- (3, 4-Difluoro-2- CllHl4F2N20S 1 260. 30 260. 5 (, hydroxy-phenyl)-thiourea Fiv OH H H 2g9 N N 1- (3, 4-Difluoro-2-hydroxy- C10HI2F2N20S phenyl)-3-isopropyl-thiourea 246. 28 246. 5 F OH 1- (3, 4-Difluoro-2-hydroxy- 290 F N'N phenyl)-3-cyclohexylmethyl-C14H18F2N20S I 300. 37 300. 6 s thiourea CAF3 OH H H t f) l- (3, 4-DiBuoro-2-hydroxy- 291 y phenyl)-3- (4-trMuoromethyl- C15HllF5N20S 1 362. 32 362. 8 , S benzyl)-thiourea OH OU H H N N CI 1- (3, 4-Difluoro-2-hydroxy- 292 y phenyl)-3- (3, 5-dichloro-phenyl)- C13H8Cl2F2N20S 1 349. 18 349. 7 thiourea ci OU | H H 1-(3, 4-Difluoro-2-hydroxy-e 293 FeC NN phenyl)-3-(4-chloro-phenyl)-C13H9CIP2N20S I 314. 74 315. 2 thiourea F OH OH r 1-(3, 4-Difluoro-2-hydrox y- phenyl)-3- (4-trifluoromethyl- C14H9F5N20S I 348. 29 348. 8 F CFi ; phenyl)-thiour : OH OH 295 F N N ^ 1- (3, 4-Difluoro-2-hydroxy- C13H16F2N20S I 286. 34 286. 6 I j phenyl)-3-cyclohexyl-thiourea OH 296 F N N 1- (3, 4-Difluoro-2-hydroxy- phenyl)-3- (2-trifluoromethyl- C14H9F5N20S I 348. 29 348. 8 t s phenyl)-thiourea OH H H 297 F N N 1- (3, 4-Difluoro-2-hydroxy- 280. 29 280. 5 phenyl)-3-phenyl-thiourea C13H10F2N20S I F OH OH H H 1- [5-Chloro-2-hydroxy-3- (1- 298 1 !. J S hydroxy-ethyl)-phenyl]-3-pentyl-C14H21CIN202S I 316. 85 316. 9 thiourea ci OH OU N N 1-Benzyl-3- [5-chloro-2-hydroxy- 299 1f j"3- (l-hydroxy-ethyl)-phenyl]- C16H17CIN202S I 336. 84 337. 2 thiourea ci Structure Chemical name Formula Synthesis MolWeight MS data methods OH OH N N 1- [5-Chloro-2-hydroxy-3- (I- 300 y hydroxy-ethyl)-phenyl]-3- (2- C17Hl9CIN202S 1 350. 86 351. 1 methyl-benzyl)-thiourea ci OH OH H H N N 1- [5-Chloro-2-hydroxy-3- (l- 301 J § C. J hydroxy-ethyl)-phcnyl]-3-C17H19C1N202S I 350. 86 351. 0 phenethyl-thiourea Ct OH OH NyN, N 1- [5-Chloro-2-hydroxy-3- (l- 302 s hydroxy-ettiyl)-phenyl]-3- (1, 1, 3, 3- C17H27C1N202S I 358. 93 359. 2 tetramethyl-butyl)-thiourea cl OH OH 1-tert-Butyl-3- [5-chloro-2- 303 TL J t hydroxy-3- (l-hydroxy-ethyl)- C13H19C1N202S I 302. 82 303. 0 phenyl]-thiourea ci OH OH H H 304 Ny N, 1- [5-Chloro-2-hydroxy-3- (1- hydroxy-ethyl)-phenyl]-3-C12H17C1N202S I 288. 79 289. 0 isopropyl-thiourea ci OH OH N N 1- [5-Chloro-2-hydroxy-3- (1- 305 I hydroxy-ethyl)-phenyl]-3-C16H23C1N202S I 342. 88 343. 1 cyclohexylmethyl-thiourea ci OH OH CF3 N N 1- [5-Chloro-2-hydroxy-3- (I- 306 I hydroxy-ethyl)-phenyl]-3- (4- C17H16CIF3N202S I 404. 83 405. 2 trifluoromethyl-benzyl)-thiourea cl OH OH Ny NqCl 1- [5-Chloro-2-hydroxy-3- (l- 307 J t J hydroxy-ethyl)-phenyl]-3- (3, 5- C15H13C13N202S I 391. 70 392. 0 dichloro-phenyl)-thiourea ci cl OH OH 1- [5-Chloro-2-hydroxy-3- (1- 308 1L J J. hydroxy-ethyl)-phenyl]-3- (4- C15H14CI2N202S I 357. 25 357. 6 ci chloro-phenyl)-thiourea OH OH OH OH H H N N 1- [5-Chloro-2-hydroxy-3- (I- 309 L /hydroxy ethyl)-phenyl]-3- (4- C16H14C1F3N202S I 390. 81 391. 0 CF3 trifluoromethyl-phenyl)-thiourea C ! OH OH 1- [5-Chloro-2-hydroxy-3- (1- 310 11 J L J hydroxy-ethyl)-phcnyl]-3-C15H21C1N202S I 328. 86 329. 4 cyclohexyl-thiourea a OH OH N N 1- [5-Chloro-2-hydroxy-3- (I- 311 | hydroxy-ethyl)-phenyl]-3-(2-CI 6HI4ClF3N202S I 390. 81 391. 0 | trifluoromethyl-phenyl)-thiourea o OH OH I- [5-Chloro-2-hydroxy-3- (l- 312 s hydroxy-ethyl)-phenyl]-3-phenyl-C15Hl5CIN202S 1 322. 81 323. 1 thiourea Ci OU N j ! H} jj 313 4-Chloro-2- (2-phenylsulfanyl- C19Hl6CINOS D 341. 85 342. 2 benzylamino)-phenol ci OH H 1 d 314 4-Chlaro-2- (2-p-tolylsulfanyl- C2OHl8CINOS D 355. 88 356. 3 Y sAA benzylamino)-phenol ci OH 4-Chloro-2- [2- (4-chloro- 315 phenylsulfanyl)-benzylamino]-C19Hl5Cl2NOS D 376. 30 376. 8 phenol ci Cl WCI OH 4-Chloro-2- [2- (4-nitro- 316 phenylsulfanyl)-benzylamino]-C19Hl5CIN203S D 386. 85 387. 2 phenol ci OU H OH 4-Chloro-2- [2- (4-methoxy- 317 J J ! phenylsulfanyl)-benzylamino]-C20H18CIN02S D 371. 88 372. 4 phenol ci TOME OU N 4-Chloro-2- [2- (2-chloro- 318 W s phenylsulfanyl)-benzylamino]-C19H15C12NOS D 376. 30 376. 8 phenol ci OH H 4-Chloro-2- [2- (3-chloro- 319 ll l phenylsulfanyl)-benzylarnino]-C19H15C12NOS D 376 30 376. 8 phénol Y ! phenol ci OH N 4-Chloro-2- [2- (3, 4-dichloro- 320 cl phenylsulfanyl)-benzylaTnino]-C19Hl4Cl3NOS D 410. 74 411. 2 phenol ci ci OH -Nt N-(4-{2-[(5-Chloro-2-hydroxy-| 321 t d s phenylanlino)-methyl]-C21H1 9CIN202S D 398. 91 399. 3 phenylsulfanyl}-phenyl)-acetamide cri OU Oh 322 4-Chloro-2- [2- (quinolin-7- s ylsulfanyl)-benzylamino]-phenol NO, NOz Oh 4-Chloro-2- [2- (4-chloro- 323 N phenylsulfanyl)-5-nitro-C19Hl4Cl2N203S D 421. 30 421. 7 benzylamino]-phenol cul ci Nô, Oh < OH 4 4-Chloro-2-(5-nitro-2-p- tolylsulfanyl-benzylamino)-phenol ci NHZ oh OH rT ! 2- [5-Amino-2- (4-chloro- 325 N phenylsulfanyl)-benzylamino]-4-C19Hl6Cl2N20S D 391. 31 391. 9 chloro-phenol ci cul OH N 4-Chloro-2- [2- (4-chloro- t N 3 benzenesu fonyl)-benzylalllino]-C19H15CI : phénol cl, OH OH CIN 327 2, 4-Dichloro-6- (2-phenylsulfanyl- benzylamino)-phenol cl Oh CI N \ 328 2, 4-Dichloro-6- (2-p-tolylsulfanyl- s benzylamino)-phenol cul OH cri N 2, 4-Dichloro-6- [2- (4-chloro- 329 9 S\¢ 1s phenylsulfanl)-benzylamino]-C19H14Cl3NOS D 410. 75 411. 1 I Tl P phenol cl ci OH H N 2, 4-Dichloro-6- [2- (4-nitro- 330 phenylsulfanyl)-benzylamino]-C19Hl4Cl2N203S D 421. 30 421. 8 phenol cl nô CL H oH H cul N 2, 4-Dichloro-6- [2- (4-methoxy- 331 phenylsulfanyl)-benzylamino]-C2OHl7Cl2NO2S D 406. 33 406. 7 phénol cl cul OYE OU r OH Jp 2, 4-Dichloro-6- [2- (2-chloro- 332 tS s phenylsulfanyl)-benzylamino]-C19H14C13NOS D 410. 75 411. 2 phenol cl, jazz OH I T OH +/03 2, 4-Dichloro-6- [2- (3-chloro- 333 !)) T phenylsulfanyl)-benzylamino]-C19H14C13NOS D 410. 75 411. 2 s ci phenol ci OH H cl N 2, 4-Dichloro-6- [2- (3, 4-dichloro- 334 phenylsulfanyl)-beiazylamino]-C19Hl3Cl4NOS D 445. 19 445. 6 phénol ci ci OH H ci N N- (4- {2- [ (3, 5-Dichloro-2-hydroxy- 335 W S phenylamino)-methyl]-C2 lH18Cl2N202S D 433. 36 433. 8 phenylsulfanyl}-phenyl)-acetamide cis NHZ OH Cl", [ [H N ylsulfanyl)-benzylamino]-phenol ci NOS OH 0 T OH 4 ! 2, 4-Dichloro-6- [2- (4-chloro- phenylsulfanyl)-5-nitro-C19H13C13N203S D 455. 74 456. 0 s benzylamino]-phenol ci cul NO, OH 338 CI'N@ 2, 4-Dichloro-6- (5-nitro-2-p- C20H16C12N203S D 435. 33 435. 7 tolylsulfanyl-benzylamino)-phenol cri NHZ OH C,", H I 2- [5-Amino-2- (4-chloro- phenylsulfanyl)-benzylamino]-4, 6- C19H15C13N20S D 425. 76 426. 0 s dichloro-phenol ci ci OH H ci N 2, 4-Dichloro-6- [2- (4-chloro- 340 benzenesulfonyl)-benzylamino]-C19Hl4Cl3NO3S D 442. 75 443. 1 phénol cul ci "Ct OH CI N \ 341 2-Chloro-6- (2-phenylsulfanyl- benzylamino)-phenol oh Oh CI N \ 342 2-Chloro-6- (2-p-tolylsulfanyl- benzylamino)-phenol OH N 2-Chloro-6- [2- (4-chloro- 343) ! J ! phenylsuHanyl)-benzylamino]-C19H15C12NOS D 376. 30 376. 7 phenol ci OH H 2-Chloro-6- [2- (4-nitro- 344 phenylsulfanyl)-benzylamino]-C19Hl5CIN203S D 386. 85 387. 2 phenol Nô Oh OH/ H ci N 2-Chloro-6- [2- (4-methoxy- 345 phenylsulfanyl)-benzylamino]-C20Hl8CIN02S D 371. 88 372. 2 phenol zone OU H 2-Chloro-6- [2- (2-chloro- 346 Sx phenylsulfanyl)-benzylamino]-C19Hl 5C12NOS D 376. 30 376. 8 phenol cl OH H 2-Chloro-6- [2- (3-chloro- 347 tJ s oeCI phenylsulfanyl)-benzylamino]-C19H15C12NOS D 376. 30 376. 8 phenol OH Oh/ H N-, p 2-Chloro-6- [2- (3, 4-dichloro- 348 WJ s¢ a phenylsulfanyl)-benzylamino]-C19H14C13NOS D 410. 74 411. 0 phenol ci OU H N- (4- {2- [ (3-Chloro-2-hydroxy- 349 WJ s phenylamino)-methyl]-C21H l9ClN202S D 398. 91 399. 3 phenylsulfanyl}-phenyl)-acetamide _NHAc OH 350 2-Chloro-6- [2- (quinolin-7- C22H17C1N20S D 392. 90 393. 4 ylsulfanyl)-benzylamino]-phenol I i i N02 OH je 1H 2-Chloro-6- [2- (4-chloro- phenylsulfanyl)-5-nitro-C19H14Cl2N203S D 421. 30 421. 5 9 S) g 8 benzylamino]-phenol ci Nez OH 352 C, __6H 2-Chloro-6- (5-nitro-2-p- C20Hl7CIN203S D 400-. 88 401. 3 tolylsulfanyl-benzylamino)-phenol i NH2 OH 2- [5-Amino-2- (4-chloro- 353 N phenylsulfanyl)-benzylamino]-6-CI9H16C12N20S D 391. 31 392. 4 s chloro-phenol ci OH C, H N,,-g 2-Chloro-6- [2- (4-chloro- 354 02S benzenesulfonyl)-benzylanlino]-C19Hl5C] 2NO3S D 408. 30 408. 6 phenol ci Oh 1 F N \ 355 2-Fluoro-6- (2-phenylsulfanyl- C19H16FNOS D 325. 40 324. 6 I i s benzylamino)-phenol OH OU F N \ 356 2-Fluoro-6- (2-p-tolylsulfanyl- 20H18FNOS D 339. 43 340. 8 i s benzylamino)-phenol OH OH i' H 2-Fluoro-6- [2- (4-chloro- tJ s phenylsulfamyl)-benzylamino]-C19H15C1FNOS D 359. 84 360. 1 phenol a ci OH N F s, A,, NJQ 2-Fluoro-6-[2-(4-nitro- 358 s phenylsulfanyl)-benzylamino]-C19Hl5FN203S D 370. 40 370. 8 phenol NO OH OH/I- H 2-Fluoro-6- [2- (4-methoxy- 359 s phenylsulfanyl)-benzylamino]-C20Hl8FN02S D 355. 43 355. 8 phenol 'OMe OH F N \ 2-Fluoro-6- [2- (2-chloro- 360 s phenylsulfanyl)-benzylamino]-C19Hl5CIFNOS D 359. 84 360. 2 phenol oh Oh H 2-Fluoro-6- [2- (3-chloro- 361 , s phenylsulfanyl)-benzylamino]-C19H15C1FNOS D 359. 84 360. 3 phenol i OH H N 2-Fluoro-6- [2- (3, 4-dichloro- 362 phenylsulfanyl)-benzylamino]-C19Hl4Cl2FNOS D phenol cl OH H F N N- (4- {2- [ (3-Fluoro-2-hydroxy- 363 W (phenylamino)-methyl]-C21H19FN202S D 382. 45 382. 9 phenylsulfanyl}-phenyl)-acetamide NHZ Oh F N \ 364 2-Fluoro-6- [2- (quinolin-7- C22Hl7FN20S D 376. 45 377. 0 i s N ylsulfanyl)-benzylamino]-phenol I i i Nos Oh t H J ! Jj 2-Fluoro-6- [2- (4-chloro- 365 N phenylsulfanyl)-5-nitro-C19Hl4CIFN203S D 404. 84 405. 3 s benzylamino]-phenol ci NOS OU 366 F w N I 2-Fluoro-6- (5-nitro-2-p- C20H17FN203S D 384. 42 384. 9 tolylsulfanyl-benzylamino)-phenol nu2 NHz NHZ OH i' 2- [5-Amino-2- (4-chloro- 367 F N phenylsulfanyl)-benzylamino]-6-C19H16CIFN20S D 374. 86 375. 1 s fluoro-phenol ci OH H N,,, g 2-Fluoro-6- [2- (4-chloro- 368 , ozS benzenesulfonyl)-benzylamino]-C19H15C1FN03S D 391. 84 392. 0 phenol ci OH cl N 2, 4-Dichloro-3-methyl-6- (2- 369 XTßTw s phenylsulfanyl-benzylamino)-C20H17C12NOS D 390. 33 390. 6 phenol cri OH CI N 370 2, 4-Dichloro-3-methyl-6- (2-p- cw tolylsulfanyl-benzylalruno)-phenol cri OH H N 2, 4-Dichloro-3-methyl-6- [2- (4- 371 ll l S chloro-phenylsulfanyl)-C20H16C13NOS D 424. 77 425. 2 benzylamino]-phenol cl, ci OH H ci N w 2, 4-Dichloro-3-methyl-6- [2- (4- 372 ll, I s nitro-phenylsulfanyl)-C20H16C12N203S D 435. 32 435. 8 benzylamino]-phenol ci "NO Oh OH/I _ H c N 2, 4-Dichloro-3-methyl-6- [2- (4- 373 , s methoxy-phenylsulfanyl)-C21H19C12N02S D 420. 35 420. 6 benzylamino]-phenol ci OMe OH H ci \ N 2, 4-Dichloro-3-methyl-6- [2- (2- 374 ; t s chloro-phenylsulfanyl)-C20H1 6Cl3NOS D 424. 77 425. 1 benzylamino]-phenol cl cl cl OH OH . 1 N 2, 4-Dichloro-3-methyl-6- [2- (3- 375 chloro-phenyisulfanyl)-C20Hl6Cl3NOS D 424. 77 425. 1 benzylamino]-phenol ci OH H N 2, 4-Dichloro-3-methyl-6- [2- (3, 4- 376) tS s Cl dichloro-phenylsulfanyl)-C20HlSC14NOS D 459. 22 459. 5 benzylamino]-phenol cl, ci OH H N N- (4- f2- [ (3, 5-Dichloro-2-hydroxy- i S \ 4-methyl-phenylamino)-methyl]-C22H20C12N202S D 447. 38 447. 8 phenylsulfanyl}-phenyl)-acetamide ci ci NHAC OH H w I 2, 4-Dichloro-3-methyl-6- [2- (quinolin-7-ylsulfanyl)-C23H18C12N20S D 441. 37 441. 6 benzylamino]-phenol ci NOS OH oH H I 2, 4-Dichloro-3-methyl-6- [2- (4- 379 T Y chloro-phenylsulfanyl)-5-nitro-C20H15C13N203S D 469. 77 470. 0 s benzylamino]-phenol cl Wcl NO2-- « OH oH H I 2, 4-Dichloro-3-methyl-6- (5-nitro- 380 N 2-p-tolylsulfanyl-benzylamino)-C21HISC12N203S D 449. 35 449. 6 phenol ci NH2 OH A CH 2- [5-Aniino-2- (4-chloro- 381 N phenylsulfanyl)-benzylamino]-4, 6-C20H17C13N20S D 439. 79 439. 9 s dichloro-5-methyl-phen. ol ci I ci OH ci N 2, 4-Dichloro-3-methyl-6- [2- (4- 382 Jt S o s chloro-benzenesulfonyl)-C20H16C13N03S D 456. 77 457. 0 benzylamino]-phenol cl OH F N \ 4-Bromo-2-fluoro-6- (2- 383 phenylsulfanyl-benzylamino)-C19H15BrFNOS D 404. 30 404. 7 phenol Oh Oh i H ! H) H < 384 C20H17BrFNOS D 418. 33 418. 6 tolylsulfanyl-benzylamino)-phenol Bu OH N 4-Brorno-2- [2- (4-chloro- 385 S phenylsulfanyl)-benzylamino]-6-C19H14BrClFNOS D 438. 74 439. 0 fluoro-phenol ci OH N-,,-p 4-Bromo-2-fluoro-6- [2- (4-iaitro- 386 s phenylsulfanyl)-benzylamino]-C19Hl4BrFN203S D 449. 30 449. 8 phenol Nô OH H OH F N \ I 4-Bromo-2-fluoro-6- [2- (4- 387 methoxy-phenylsulfanyl)-C20Hl7BrFN02S D 434. 33 434. 7 benzylamino]-phenol Oye OMe OH 4-Bromo-2- [2- (2-chloro- 388 F\ S phenylsulfanyl)-benzylamino]-6-C19H14BrCIFNOS D 438. 74 439. 2 fluoro-phenol Br OH N 4-Bromo-2- [2- (3-chloro- 389 phenylsulfanyl)-benzylamiiaol-6-C19Hl4BrCIFNOS D 438. 74 439. 1 /s\ ^/ci fluoro-phenol Bu OU H NN-,-p 4-Bromo-2- [2- (3, 4-dichloro- 390 3 cl phenylsulfanyl)-benzylamino]-6-C19Hl3BrCl2FNOS D 473. 19 473 6 fluoro-phenol zea Oh OU F N \ N- (4- {2- [ (5-Bromo-3-fluoro-2- 391 , S hydxoxy-phenylamino)-methyl]-C21H18BrFN202S D 461. 35 461. 8 phenylsulfanyl}-phenyl)-acetamide Ber OU Oh F N \ 4-Bromo-2-fluoro-6- [2- (quinolin- 392 C22H16BrFN20S D 455. 35 455. 7 /s N 7-ylsulfanyl)-benzylammo]-phenol Br I// NO2 OH H I 4-Bromo-2- [2- (4-chloro- F N C19H13BrC1FN203 393 Fl, N phenylsulfanyl)-5-nitro-C19Hl3BrCIFN203 D 483. 74 484. 1 s benzylamino]-6-fluoro-phenol ber NOS OH 394 F \ N I 4-Bromo-2-fluoro-6- (5-nitro-2-p- C20H16BrFN203S D 463. 32 463. 7 tolylsulfanyl-benzylamino)-phenol S,, a Air NHZ OU 2- [5-Amino-2- (4-chloro- 395 I phenylsulfanyl)-benzylamino]-4-C19H15BrC1FN20S D 453. 76 454. 1 s bromo-6-fluoro-phenol Br Ut OH F, N 4-Bromo-2- [2- (4-chloro- 396 8 benzenesulfonyl)-benzylamino]-6-C19H14BrClFN03S D 470. 74 471. 2 fluoro-phenol ar I ci OH 397 F N 2, 3-DifluoTo-6- (2-phenylsulfanyl- C19Hl5F2NOS D 343. 39 343. 6 397 'C19H15F2NOS D 343. 39 343. 6 5XC benzylamino)-phenol OH H H jf) t 398 'C20H17F2NOS D 357. 42 357. 8 F) : benzylamino)-phenol Oh OU OH 4C3 \ [ 399 . benzyjamino]-2, 3-difluoro-phenol ci OU OH H N 2, 3-Difluoro-6- [2- (4-nitro- 400 F) s phenylsulfanyl)-benzylamino]-C 19H14F2N203 S D 388. 39 388 8 phenol OU F OH N 2, 3-Difluoro-6- [2- (4-methoxy- 401 Fu S phenylsulfanyl)-benzylamino]-C20H17F2N02S D 373. 42 373. 7 phenol OMe OH F N 6- [2- (2-Chloro-phenylsulfanyl)- 402 F , S benzylamino]-2, 3-difluoro-pheno1 Oh OU w 6- [2- (3-Chloro-phenylsulfanyl)- 403 C19H14C1F2NOS D 377. 83 378. 2 i s ci benzylamino]-2, 3-difluoro-phenol i OH H N 6- [2- (3, 4-Dichloro- 404 F S \ i phenylsulfanyl)-benzylamino]-2, 3- C19H13C12F2NOS D 412. 28 412. 6 difluoro-phenol ci OH F N \ N- (4- {2- [ (3, 4-Difluoro-2-hydroxy- 405 phenylamino)-methyl]-C2lHl8F2N202S D 400. 44 400. 8 phenylsulfanyl}-phenyl)-acetamide v'NHAc OH F F N \ 2, 3-Difluoro-6- [2- (quinolin-7- 406 C22H16F2N20S D 394. 44 394. 9 s N\ ylsulfanyl)-benzylamino]-phenol i i NOYA Oh 6- [2- (4-Chloro-phenylsulfanyl)-5- 407 W T nitro-benzylamino]-2, 3-difluoro-C 19H13ClF2N203S D 422. 83 423. 3 Fw S phenol ci NOS Oh 408 F N 2, 3-Difluoro-6- (5-nitro-2-p- C20H16F2N203S D 402. 41 402. 8 tolylsulfanyl-benzylamino)-phenol F < NH2 OH F N 6- [5-Amino-2- (4-chloro- 409 phenylsulfanyl)-benzylamino]-2, 3- C19Hl5CIF2N20S D 392. 85 393. 0 difluoro-phenol Sci OH 6- [2- (4-Chloro-benzenesulfonyl)- Fv 02S> beIlZylat o]-2X3-difluoro-phenol cl OH OH N 4-Chloro-2- (l-hydroxy-ethyl)-6- 411 t ! j' (2-phenylsulfanyl-benzylamino)-C21H20CIN02S D 385. 91 386. 4 phénol cl OH OH H N 4-Chloro-2- (l-hydroxy-ethyl)-6- 412 (/S (2-p-tolylsulfanyl-benzylamino)-C22H22C1N02S D 399. 93 400. 2 7 phenol ci OH OH 4-Chloro-2- [2- (4-chloro- 413 l l l phenylsulfanyl)-benzylamino]-6-C21H19Cl2N02S D 420. 35 420. 9 (1-hydroxy-ethyl)-phenol cl OH OU 4-Chloro-2- (1-hydroxy-ethyl)-6- 414 t XJ S [2-(4-nitro-phenylsulfanyl)-C21H19ClN204S D 430. 90 431. 3 benzylamino]-phenol Ci 2 1 OH OH N,, p 4-Chloro-2- (I-hydroxy-ethyl)-6- 415 , S [2- (4-methoxy-phenylsulfanyl)- C22H22C1N03S D 415. 93 416. 3 benzylamino]-phenol ci OMe OH OH 4-Chloro-2- [2- (2-chloro- 416 + s phenylsulfanyl)-benzylamino]-6-C21H19C12N02S D 420. 35 420. 9 (1-hydroxy-ethyl)-phenol cri OH Cl 4-Chloro-2- [2- (3-chloro- w 417 phenylsulfanyl)-benzylamino]-6-C21H19C12N02S D 420. 35 420. 8 /s\ ^/ci 1_hydroxy-ethyl)-phenol ci OH OH N 4-Chloro-2- [2- (3, 4-dichloro- 418 phenylsulfanyl)-benzylamino]-6-C2lHl8Cl3NO2S D 454. 80 455. 2 T n (1-hydroxy-ethyl)-phenol ci Cul H N- [4- (2- { [5-Chloro-2-hydroxy-3- 419 / (l-hydroxy-ethyl)-phenylamino]-C23H23C1N203S D 442. 96 443. 4 s methyl-phenylsulfanyl)-phenyl]- Cl t NHAc acetamide | OH OU OH OH N 4-Chloro-2- (l-hydroxy-ethyl)-6- 420 [2- (quinolin-7-ylsulfanyl)- C24H21CIN202S D 436. 95 437. 3 3 N benzylamino]-phenol ci NOS OH OH ß 4-Chloro-2- [2- (4-chloro- w phenylsulfanyl)-5-nitro- s benzylamino]-6-(1-hydroxy-ethyl)- n j ! benzylamino]-6- (l-hydroxy-ethyl)- phenol ci ci Nos OH OH Cb 4-Chloro-2-(1-hydroxy-ethyl)-6- 422 N (5-nitro-2-p-tolylsulfanyl-C22H21CIN204S D 444. 93 445. 3 benzylamino)-phenol ci NH2 OH Oh OH OH ß 2-[5-Amino-2-(4-chloro- 423 I phenylsulfanyl)-benzylamino]-4-C21H20C12N202S D 435. 37 435. 6 Y sugh chloro-6-(1-hydroxy-ethyl)-phenol ci OH OU 4-Chloro-2- [2- (4-chloro- 424 02S benzenesulfonyl)-benzylamino]-6-C2lHl9Cl2NO4S D 452. 35 452. 5 ( (1-hydroxy-ethyl)-phenol ci OH OH N 2-Hydroxymethyl-6- (2- 425 W | phenylsulfanyl-benzylamino)-C20H19N02S D 337. 44 337. 8 phenol OH OH OH OU 426 2-Hydroxymethyl-6- (2-p- C21H21N02S D 351. 46 351. 8 s o} tolylsulfanyl-benzylamino)-phenol i OH OH N 2- [2- (4-Chloro-phenylsulfanyl)- 427 W I benzylamino]-6-hydroxymethyl-C20H18ClN02S D 371. 88 371. 9 phenol ci OH OH 2-Hydroxymethyl-6- [2- (4-nitro- 428 phenylsulfanyl)-benzylamino]-C20Hl8N204S D 382. 43 382. 7 phenol NO z OH OH 2-Hydroxymethyl-6- [2- (4- 429 W I methoxy-phenylsulfanyl)-C21H1lN03S D 367. 46 367. 9 benzylamino]-phenol OMe OH OU 2- [2- (2-Chloro-phenylsulfanyl)- 430 s benzylamino]-6-hydroxymethyl-C20H18CIN02S D 371. 88 371. 9 phenol Cl OH OH 2- [2- (3-Chloro-phenylsulfanyl)- 431 W s Cl benzylamino]-6-hydroxymethyl-C20H18ClN02S D 371. 88 371. 9 phenol OH OH N 2- [2- (3, 4-Dichlora- 432 W s Cl phenylsulfanyl)-benzylamino]-6-C20H17Cl2N02S D 406. 33 406. 5 hydroxymethyl-phenol cri OH OH N- (4- {2- [ (2-Hydroxy-3- hydxoxymethyl-phenylamino)- ' s, methyl]-phenylsulianyl}-phenyl)- acetamide NHZ OH OU N 434 2-Hydroxymethyl-6- [2- (quinolin- C23H20N202S D 388. 48 388. 8 seC Nq 7-ylsulfanyl)-benzylammo]-phenol i i NHZ oH oH r 2- [2- (4-Chloro-phenylsulfanyl)-5- 435 W nito-benzylarnino]-6-C20H17ClN204S D 416. 88 417. 2 hydroxymethyl-phenol cul NOS OH OU NO2 4 436 N C21H20N204S D 396. 46 396. 8 nu2 _ NH i NHz OH OH 2- [5-Amino-2- (4-chloro- 437 N phenylsulfanyl)-benzylamino]-6-C20Hl9CIN202S D 386. 90 387. 1 hydroxymethyl-phenol ci OH OH N 2- [2- (4-Chloro-benzenesulfonyl)- 438 benzylamino]-6-hydroxymetliyl-C20Hl8CIN04S D 403. 88 44. 0 phenol Cul- OH | OH X 2, 4-Dichloro-3-ethyl-6- (2- 439 \t s phenylsulfanyl-benzylamino)-C21H19Cl2NOS D 390. 33 390. 5 phenol cl OH 440 N 2, 4-Dichloro-3-ethyl-6- (2-p- C22H2lCl2NOS D 418. 37 418. 7 r so tolylsulfanyl-benzylamino)-phenol ci OH H N 2, 4-Dichloro-3-ethyl-6- [2- (4- 441 Xl d s chloro-phenylsulfanyl)-C21H18C13NOS D 438. 79 439. 0 benzylamino]-phenol ci I ci ci N 2, 4-Dichloro-3-ethyl-6- [2- (4-nitro- 442 Jf su¢Ds phenylsulfanyl)-benzylamino]-C21H18C12N203S D 449. 34 449-7 phénol a <k. Cl NO2 I oh OH ci N 2, 4-Dichloro-3-ethyl-6- [2- (4- 443 1I wJ s methoxy-phenylsulfanyl)-C22H21C12N02S D 43437 434_6 benzylamino]-phenol ci ORME OH N 2, 4-Dichloro-3-ethyl-6- [2- (2- 444 1 chloro-phenylsulfanyl)-C21Hl 8Cl3NOS D 438. 79 438. 9 benzylamino]-phenol cl cl OH cl HN\JU 2, 4-Dichloro-3-ethyl-6- [2- (3- 445 chloro-phenylsulfanyl)-C21H18Cl3NOS D 438. 79 438. 9 g So benzylamino]-phenol ci OH N 2, 4-Dichloro-3-ethyl-6- [2- (3, 4- 446 dichloro-phenylsulfanyl)-C2lHl7Cl4NOS D 473. 24 473. 5 benzylamino]-phenol ci I i ci OH cl ei N N- (4-12- [ (3, 5-Dichloro-4-ethyl-2- 447 hydroxy-phenylainino)-methyl]-C23H22Cl2N202S D 461. 40 461. 6 phenylsulfanyl}-phenyl)-acetamide ci NHAc OH N 2, 4-Dichloro-3-ethyl-6- [2- 448 l l l (quinolin-7-ylsulfanyl)-C24H20Cl2N20S D 455. 39 455. 7 I--z benzylaminol-phenol cl w NO2 OH OH,"2, 4-Dichloro-3-ethyl-6- [2- (4- W chloro-phenylsulfanyl)-5-nitro-C21H17C13N203S D 483. 79 484. 0 i s benzylamino]-phenol cl ci cl v c NO2 OH A « oH H \ I'2, 4-Dichloro-3-ethyl-6- (5-nitro-2- 450 w t T p-tolylsulfanyl-benzylamino)-C22H20Cl2N203S D 463. 37 463. 5 phenol cri NH2 OH A 2- [5-Amino-2- (4-chloro- 451 N phenylsulfanyl)-benzylan-lino]-4, 6- C2lHl9Cl3N20S D 453. 81 454. 1 s dichloro-5-ethyl-phenol cul cl OH N 2, 4-Dichloro-3-ethyl-6- [2- (4- 452 chloro-benzenesulfonyl)-C21H18C13N03S D 470. 79 471. 0 i o2s benzylamino]-phenol ci cl OH Hooc N 2-Hydroxy-3- (2-phenylsulfanyl- 453 C2H17N03S D 351. 42 351. 6 i s benzylarnino)-benzoic acid OH HOOC N 454 2-Hydroxy-3- (2-p-tolylsulfanyl- C21H19N03S D 365. 44 365. 8 benzylamino)-benzoic acid i OH H H N 3- [2- (4-Chloro-phenylsulfanyl)- 455 benzylamino]-2-hydroxy-benzoic C20II16CIN03SD385. 86 385. 1 acrid cl OH Hooc N 2-Hydroxy-3- [2- (4-nitro- 456 W s, phenylsulfanyl)-benzylamino]-C20H16N205S D 396. 11 396. 4 benzoic acid 'nô 2 OH H N 2-Hydroxy-3- [2- (4-methoxy- 457 11 l I phenylsulfanyl)-benzylamino]-C21H19N04S D 381. 44 381. 6 benzoic acid OMe OH H HOOC N \ 3- [2- (2-Chloro-phenylsulfanyl)- 458 WJ s benzylamino]-2-hydroxy-benzoic C20H16CIN03S D 385. 86 386. 0 acid OH OH HOOC N 3- [2- (3-Chloro-phenylsulfanyl)- 459 W s cl benzylamino]-2-hydroxy-benzoic C20H16CIN03S D 385. 86 386. 0 acid OH OU HOOC N 3- [2- (3, 4-Dichloro- 460 W S Cl phenylsulfanyl)-benzylamino]-2-C20HlSC12N03S D 420. 31 420. 7 hydroxy-benzoic acid ci OH HOOC N 3- [2- (4-Acetylamino- 461 U s phenylsulfanyl)-benzylamino]-2-C22H20N204S D 408. 47 408. 7 hydroxy-benzoic acid NHZ OH Hoo N 2-Hydroxy-3- [2- (quinolin-7- 462 3 N ylsulfanyt)-benzylaTnino]-benzoic C23Hl8N203S D 402. 46 402. 8 acid N02 Oh wt'3-[2-(4-Chloro-phenylsulfanyl)-5-j | 463 Hooc N nitro-benzylamino]-2-hydroxy-C20Hl5CIN205S D 430. 86 430. 9 s benzoic acid cl N02 OH H I 2-Hydroxy-3- (5-nitro-2-p- 464 H N tolylsulfanyl-benzylamino)-C2lHl8N205S D 410. 44 410. 7 benzoic acid NH, OH OH HOOC N 2- [5-Amino-2- (4-chloro- 465 + T phenylsulfanyl)-benzylamino]-6-C20H19ClN202S D 386. 90 387. 2 s hydroxymethyl-phenol ci OH OH HOOC N 3- [2- (4-Chloro-benzenesulfonyl)- 466 tJ o2s benzylamino]-2-hydroxy-benzoic C20H16ClN05S D 403. 88 404. 1 acid Sci OH F) N 2-Fluorc-4-nitro-6- (2- 467 rs, phenylsulfanyl-benzylamino)-C 19H15FN203S D 370. 40 370. 8 phenol N02 OH H 468 C20H17FN203S D 384. 43 384. 9 Y sxlí q tolylsulfanyl-benzylamino)-phenol N02 OH H FA N 2- [2- (4-Chloro-phenylsulfanyl)- 469 benzylamino]-6-fluoro-4-nitro-C19Hl4ClFN203S D 404. 84 405. 0 phenol NOZ I CI OH H F) N 2-Fluoro-4-nitro-6- [2- (4-nitro- 470 phenylsulfanyl)-benzylamino]-C19Hl4FN305S D 415. 40 415. 8 phenol NOZ I NO oh OH H N 2-Fluoro-6- [2- (4-methoxy- 471 t J s phenylsulfanyl)-benzylamino]-4-C20H17FN204S D 400. 43 400. 9 nitro-phenol NOz OMe OH H F N 2- [2- (2-Chloro-phenylsulfanyl)- 472 , S benzylamino]-6-fluoro-4-nitro-C19H14C1FN203S D 404. 84 405. 0 phénol NOZ CI I/ Oh 2- [2- (3-Chloro-phenylsulfanyl)- 473) ! T'benzylammo]-6-fluoro-4-mtro-C19H14C] FN203S D 404. 84 405. 0 phénol NOZ I/ OH H F) N 2- [2- (3, 4-Dichloro- 474 phenylsulfanyl)-benzylamino]-6-C19Hl3Cl2FN203S D 439. 29 439. 9 fluoro-4-nitro-phenol NOZ I CI OH FuANx N-(4-{2-[(3-Fluoro-2-hydroxy-5- 475 nitro-phenylamino)-methylj-C2lHl8FN304S D 427. 45 427. 9 phenylsulfanyl}-phenyl)-acetamide N02 NHZ NH OU 2-Fluoro-4-nitro-6- [2- (quinolin-7- 476 , s \ N ylsulfanyl)-benzylamino]-phenol Noz i i NOS OH 2- [2- (4-Chloro-phenylsulfanyl)-5- 477 nitro-benzylarnino]-6-fluoro-4-C19Hl3CIFN3059 D 449. 84 450. 1 s nitro-phenol N02 cri Nos OH H F N \ 2-Fluoro-4-nitro-6- (5-nitro-2-p- C20H16FN304S D 429. 42 429. 8 tolylsulfanyl-benzylamino)-phenol OH A NHz NHZ Oh F N 2- [5-Amino-2- (4-chloro- 479' phenylsulfanyl)-benzylamino]-6-C19H15CIFN302S D 419. 86 420. 2 s fluoro-4-nitro-phenol Nô, ci OH H FI (N 2- [2- (4-Chloro-benze-nesulfonyl)- 480 benzylamino]-6-fluoro-4-nitro-C19Hl5CIFN205S D 436. 84 437. 1 phenol T ! ! ! phenol NOZ I CI Ct OH CI NO 481 2, 4-Dichloro-6-(3-phenoxy-C19H15CI'N02 D 360. 23 360. 5 cl 43 benzylamino)-phenol ci OH CI N \ O 482 /2, 4-Dichloro-6- [3- (4-chloro- C19H15C13N02 D 394. 68 395. 0 i phenoxy)-benzylamino]-phenol ci ci OH CI N O 483 2- [3- (4-tert-Butyl-phenoxy)- C23H23Cl2NO2 D 416. 34 416. 8 benzylamino]-4, 6-dichloro-phenol OH Oh CI N 484 N 0 2- (3-Benzyloxy-benzylamino)-4, 6- C201417Cl2NO2 D 374. 26 374. 6 dicliloro-phenof cl OH CI N 4 I i o 2- (2-Benzyloxy-benzylamino)-4, 6- C20H17C12N02 D 374. 26 374. 6 dichloro-phenol cl, OH H ci N w 2, 4-Dichloro-6- [ (naphthalen-1- t . yimethyl)-amino]-phenol Cl OH/I S H 2, 4-Dichloro-6- (4-methylsulfanyl- C14H13C12NOS D 314. 23 314. 7 benzylamino)-phenol C ! OH H I w N 2, 4-Dichloro-6- (2-ethylsulfanyl- C15H15C12NOS D 328. 26 328. 6 benzylamino)-phenol Ci OH CI N 489 2, 4-Dichloro-6- (2-morpholin-4-yl- C17H18C12N202 D 353. 24 353. 6 ci 009 benzylammo)-phenol cl 0 OU 2, 4-Dichloro-6- { [2- (4-chloro- 490 , S phenylsulfanyl)-thiophen-3-C17H12C13NOS2 D 416. 77 416. 9 ylmethyl]-amino}-phenol cl OH Nez I N N 2, 4-Dichloro-6- [ (5-phenyl-2H- 491 i imidazol-4-ylmethyl)-amino]-C16H13C12N30 D 334. 20 334. 6 phenol ci Br 2- [ (5-Bromo-thiophen-2- 492 I ylxnethyl)-amino]-4, 6-d. ichloro- C11H8BrC12NOS D 353. 06 353. 4 /-phenol cl OU OH , H O 493 I 2 4-Dichloro-6- [3- (4-methoxy- phenoxy)-benzylamino]-phenol ci OH H ci N w 2 4-Dichloro-6- (3-ethyl- benzylamino)-phenol o OH ci N caf 2, 4-Dichloro-6- 3-trifluorometh 1- 495 X benzylamino)-ph nol C14HlOCI F3NO D 330. 14 336. 5 cl OH H ci N W 2, 4-Dichloro-6- (2-chloro-6-fluoro- 496.'C13H9C13FN0 D 320. 57 320. 8 benzylamino)-phenol cl Oh ci N 0 2, 4-Dichloro-3-methyl-6- (3- phenoxy-benzylamino)-phenol ci OH CI N 2, 4-Dichloro-3-methyl-6- [3- (4- 498 I i chloro-phenoxy)-benzylamino]-C20H17C13N02 D 408. 71 409. 2 c. J P phenol ci OH CI I N 2- [3- (4-tert-Butyl-phenoxy)- 499/9Y A benzylamino]-4, 6-dichloro-3- C24H25C12N02 D 430. 37 430. 5 methyl-phenol OH S H \ a w 500 CN 0 2- (3-Benzyloxy-benzylamino)-4, 6- dichloro-3-methyl-phenol cl OH CI N 501 0 2- (2-Benzyloxy-benzylamino)-4, 6- C2lHl9Cl2NO2 D 388. 29 388. 6 dichloro-3-methyl-phenol cul OH Cl 1 Ns 2, 4-Dichloro-3-methyl-6- 502 [ (naphthalen-1-ylmethyl)-amino]- C18Hl5Cl2NO D 332. 23 332. 6 phenol cl OH Cl N 2, 4-Dichloro-3-methyl-6- (4- 503 W methylsulfanyl-benzylamino)-C15HlSC12NOS D 328. 26 328. 6 phenol ci OH H 5n N w 2, 4-Dichloro-3-methyl-6- (2- 504 C16H17C12NOS D 342. 29 342. 8 cl A ethylsulfanyl-benzylammo)-phenol cl OH ci N w 2, 4-Dichloro-3-methyl-6- (2- 505 Jt S I morpholin-4-yl-benzylamino)-C18H20C12N202 D 367. 27 367. 6 cl to) phenol OH ci NS 2, 4-Dichloro-3-methyl-6- { [2-(4- 506, J-J s/+ chloro-phenylsulfanyl)-thiophen-3-C18H14C13NOS2 D 430. 80 431. 2 T} CI ylmethyl]-amino}-phenol cl OH N-\ N 2, 4-Dichloro-3-methyl-6- [ (5- 507 , phenyl-2H-imidazol-4-ylmethyl)-C17H15C12N30 D 348. 23 348. 8 amino]-phenol c Br 2- [ (5-Bromo-thiophen-2- 508 Cls4f N ylmethyl)-amino]-4, 6-dichloro-3-C12HlOBrC12NOS D 367. 09 367. 4 CI) methyl-phenol OH , I OH I CI N Cl 2, 4-Dichloro-6- [3- (4-methoxy- 509 I i/phenoxy)-benzylamino]-3-methyl-. C21H19CI2N03 D 404. 29 404. 5 cul phenol OH OH H ci N 2, 4-Dichloro-6- (3-methyl- benzylamino)-3-methyl-phenol Ci Oh OH \/X3s 2, 4-Dichloro-3-methyl-6- (3- 511 trifluoromethyl-benzylammo)-C15Hl2Cl2F3NO D 350. 17 350. 7 phenol ci OH ci N 2, 4-Dichloro-3-methyl-6- (2- 512 I chloro-6-fluoro-benzylamino)-C14H11C13FNO D 334. 60 335. 0 cl phenol C ! OH ci N 0 2-Chloro-6- (3-phenoxy- 513 C19H16C1N02 D 325. 79 326. 1 benzylamino)-phenol OH cul N O 514 i 2-Chloro-6- [3- (4-chloro-phenoxy)- C19H15C12N02 D 360. 23 360. 6 benzylamino]-phenol Ci ci N OH CI N O 515 2- [3- (4-tert-Butyl-phcnoxy)- C23H24CIN02 D 381. 90 382. 2 benzylamino]-6-chloro-phenol oh OH I CI NO C, I (tH i . chloro-phenol C20H18C1N02 D 339. 82 340. 1 I 1 X chloro-phenol F 1-0. I OH CI N 517 o 2-(2-Benzyloxy-benzylamino)-6-C20H1 8ClN02 D 339. 82 340. 1 chloro-phenol oh 518 N 2-Chloro-6- [ (naphthalen-l- W W ylmethyl)-amino]-phenol ----- OH ci N 2-Chloro-6- (4-methylsulfanyl- 519 C14H14C1NOS D 279. 79 280. 2 benzylamino)-phenol OH H 520 v X 2Choro-6-2-ehylsulfanyl-C15H16CDIOS D 293. 81 294. 3 OH n OH CI N 521 2-Chloro-6- (2-morpholin-4-yl- C17H19C1N202 D 318. 80 319. 1 benzylamino)-phenol ou OH N 2-Chloro-6-f [2- (4-chloro- 522 W A phenylsulfanyl)-iophen-3-C17H13C12NOS2 D 3 82. 33 382. 6 ylmethyl]-amino}-phenol 1/cri OH Nez H N 2-Chloro-6- [ (5-phenyl-2H- 523 W L iniidazol-4-ylmethyl)-amino]-C16H14ClN30 D 299. 75 300. 2 phenol Br 524 I f HN jf 2-[(5-Bromo-dliophen-2-C1 lH9BrClNOS D 318. 62 319. 5 y i ylmethyl)-amino]-6-chloro-phenol OH ci N Clo8<r"N o 2-Chloro-6- [3- (4-methoxy- phenoxy)-benzylamino]-phenol OH H vo q | OH < s l benzylamino)-phenol Oh 2-Chloro-6- (3-trifluoromethyl- H ! s benzylamino)-phenol OH 528 2-Chloro-6- (2-chloro-6-fluoro- w 13H10C12FN0 D 286. 13 286. 6 OH ci OH F N 2-Fluoro-6- (3-phenoxy- ', '\ beazylammo)-phenol Oh OU F NEZ O 530 /2-Fluoro-6- [3- (4-chloro-phenoxy)- C19H15C1FN02 D 343. 77 344. 0 benzylaminol-phenol OH oh F N O 531 I i 2- [3- (4-tert-Butyl-phenoxy)- C23H24FN02 D 365. 44 366. 0 benzylarnimo]-6-fluoro-phenol Oh H 0 2- (3-Benzyloxy-benzylamino)-6- C20H18FN02 D 323. 36 323. 8 fluoro-phenol OH oh F < ZON 533 2- (2-Benzyloxy-benzylammo)-6- c20H18FN02 D 323. 36 323. 8 fluoro-phenol w OH 2-Fluoro-6- [ (naphthalen-1- 534 F-_ W ylmethyl)-amino]-phenol i OH S. 2-Fluoro-6- (4-methylsulfanyl- 535 F N C14H14FNOS D 263. 33 263. 5 535 FA. HJi 2-Fluoro-6- (4-methylsulfanyl- ci4H14FNOS D 263. 33 263. 5 OH OH H 536 F \ 2-Fluoro-6- (2-ethylsulfanyl- C15H16FNOS D 277. 36 277. 8 benzylamino)-phenol 1 OH F N 2-Fluoro-6- (2-morpholin-4-yl- 537 , N benzylamino)-phenol C17H19FN202 D 302. 34 302. 8 0 oh N 2-Fluoro-6- ( [2- (4-chloro- 538 phenylsulfanyl)-thiophen-3-C17Hl3CIFNOS2 D 365. 87 366. 0 ylmethyl]-amino}-phenol ,/cri OH NEZ F N i N 2-Fluoro-6- [ (5-phenyl-2H- 539 imidazol-4-ylmethyl)-aminol-C16Hl4FN30 D 283-30 283. 8 phenol Br f a phenol w . ' "/ylmethyl)-ammo]-6-fluoro-phcnol i oh \ N O 541 2-Fluoro-6- [3- (4-methoxy- C20Hl8FN03 D 339. 36 339. 8 phenoxy)-benzylamino]-phenol 0 Oh 2-Fluoro-6- (3-methyl- C14H14FN0 D 231. 27 231. 4 h) benzylammoj-phenol OH 2-Fluoro-6- (3-trifluoromethyl- C14H11F4NO D 285. 24 285. 5 543 F I \ N CF3 benzylamino)-phenol zu OH 2-Fluoro-6- (2-chloro-6-fluoro- N ! benzylammo)-phenol f 0 OH 544 F N C13H1 C1F2N0 D 269. 67 270. 1 cul 0 OH f OH 0 2, 3-Difluoro-6- (3-pheno- 545 F ,, benzylamino)-phenol C19H15F2N02 D 327. 32 327. 6 OH F N 546 2, 3-Difluoro-6- [3- (4-chloro- C19Hl4CIF2NO2 D 361. 76 362. 0 phenoxy)-benzylamino]-phenol cl OH :''O 547 FJ 2- [3- (4-tert-Butyl-phenoxy)- C23H23F2N02 D 383. 43 383. 8 benzylamino]-5, 6-difluoro-phenol OH 0 2- (3-Benzyloxy-benzylamino)-5, 6- 548 Ft/N\/4 2-(3-Benzyloxy-benzylamino)-5, 6-C20H1 7F2NO2 D 341. 35 341. 7 548 + difluoro-phenol W F OH F N 549 F JS ° 2-(2-Benzyloxy-benzylamino)-5, 6-C20H17F2NO2 D 341. 35 341. 7 difluoro-phenol OH 2, 3-Difluoro-6- [ (naphthalen-l- !) ! ylmethyl)-amino]-phenol it Fuzz /su OH 2 3-Difluoro-6- (4-methylsulfanyl- 551 F N/r'C14H13F2NOS D 28132 281. 6 benzylamino)-phenol F OH H 552 FNs JQ 2, 3-Difluoro-6- (2-ethylsulfanyl- C15H15F2NOS D 295. 35 295. 7 s) benzylamino)-phenol OH OU F N 553 F, N 9 2, 3-Difluoro-6-(2-morpholin-4-yl-C17H18FZN 202 D 320. 33 320. 8 benzylamino)-phenol ou OH F N 2, 3-Difluoro-6- { [2- (4-chloro- 554 phenylsulfanyl)-thiophen-3-C17Hl2CIF2NOS2 D 383. 86 384. 2 ylmethyl]-amino}-phenol /cri OH N ~\ H N F N 2, 3-Difluoro-6- [ (5-phenyl-2H- 555 ) 0 imidazol-4-ylmethyl)-amino]-C16H13F2N30 D 301. 29 301. 6 phenol Br OH S 2-[(5-Bromo-thiophen-2-s 556 FX/N-ylmethyl)-amino]-5, 6-difluoro-Cl lH8BrF2NOS D 320. 15 320. 4 phenol F OH F N \ 557 F I i I 2, 3-Difluoro-6- [3- (4-methoxy- C20H17F2N03 D 357. 35 357. 6 phenoxy)-benzylamino]-phenol oh o OH 2, 3-Difluoro-6- (3-methyl- 558 w Cl4H13F2NO D 249. 26 249. 6 OH i F OH 2 3-Difluoro-6- (3-trifluoromethyl- 559 F \ N/\F'C14H10FSN0 D 303. 23 303. 7 benzylamino)-phenol OH F/ OH 560 F N 2, 3-Difluoro-6- (2-chloro-6-fluoro- 560 I C13H9C1F3N0 D 287. 66 288. 1 benzylamino)-phenol CI cl N- (3, 5-Dichloro-2-hydroxy-4- 61 methyl-phenyl)-C-phenyl-C14Hl3Cl2NO3S B 346. 23 347. 0 methanesulfonamide ci Fr Cl Butane-1-sulfonic acid (3, 5- 562 N 50 dichloro-2-hydroxy-4-methyl-C11H15C12N03S B 312. 21 312. 1 ci phenyl)-amide Octane-1-sulfonic acid (3, 5- 563 H 0 dichloro-2-hydroxy-4-methyl-C15H23Cl2NO3S B 368. 32 368. 3 s phenyl)-amide OH Cl ci Propane-2-sulfonic acid (3, 5- 564 XNH o dichloro-2-hydroxy-4-methyl-ClOH13C12N03S B 298. 18 298. 1 ci phenyl)-amide ci ci N- (3, 5-Dichloro-2-hydroxy- 565 vNH o phenyl)-C-phenyl-C13Hl lC12N03S B 332. 20 332. 4 cl methanesulfonamide ci ci 566 NH Butane-l-sulfonic acid (3 5- - , s- dichloro-2-hydroxy-phenyl)-amide ci ou Octane-1-sulfonic acid (3, 5- 567 I N\ clichlro-2-hydroxy-phenyl)-amide C14H21C12N03S B 354. 29 354. 6 s oh CL cl tOH 1 l Y 568 ''0 t'. 'C9H11CI2N03S B 284. 16 284. 5 r Cl OHO e a ofP)- 569 X n'-° N-(3-Chloro-2-hydroxy-phenyl)-C13H12CIN03 S B 297. 76 297. 9 C-phenyl-methanesulfonarnide ci oe Buta-ne-l-sulfonic acid (3-chloro- 2 h x hen 1-amide C10H14C1N03S B 263. 74 264. 0 Cl OHO Y-P Y) Octane-1-sulfonic acid (3-chloro- 571 H o [ Octe-l-sulfomc acid (3-chloro-ci4H22C ! N03S B 319. 85 320. 3 571 \ N\ 0 2-hydroxy-phenyl)-amide C14H22C1N03S B 319. 85 320. 3 o OH o nu 572 Propane-2-sulfonic acid (3-chloro- 'S 2-hydroxy-phenyl)-amide a ot -- N- (3-Fluoro-2-hydroxy-phenyl)-C- 573 phenyl-methanesulfonamide C13Hl2FN03S B 281. 30 281. 8 F oit Butane-l-sulfonic acid (3-fluoro-2- 574 s C10H14FN03S B 247. 29 247. 8 F o hydroxy-phenyl)-amide 575 H o Octane-1-sulfonic acid (3-fluoro-2-C14H22FN03S B 303. 39 303. 8 ¢ hydroxy-phenyl)-de 0 o OH F 576 ANXHS"O Propane-2-sulfonic acid (3-fluoro- 'S 2-hydroxy-phenyl)-amide NH N- (3, 4-Difluoro-2-hydroxy- 577 S ; l phenyl)-C-phenyl-C13HllF2NO3S B 299. 29 300. 8 methanesulfonamide NH o Butane-1-sulfonic acid (3, 4- p difluoro-2-hydroxy-phenyl)-amide C10H13F2N03S B 265. 28 265. 7 F Ot-f 579 H O 2 Octanol-sulfonic acid (3, 4- r N S/u) difluoro-2-hydroxy-phen : yl)-amide ils F OH F 580 Propane-2-sulforiic acid (3, 4- F ox diBuoro-2-hydroxy-phenyl)-amide ci CI 581 HO cl (3, 5-Dichloro-2-hydroxy-4- 581 o methyl-phenyl)-carbamic acid C14H19C12N03 F, G, H 320. 22 320. 2 NH hexyl ester 0 ci 582 HO-O-C ( (3, 5-Dichloro-2-hydroxy-phenyl)-C13H17C12N03 F, G, H 306. 18 306. 4 o-carbamic acid hexyl ester NH zozo O ci 583 HO (3-Chloro-2-hydroxy-phenyl)-C13Hl8CIN03 F, G, H 271. 74 272. 1 o carbamic acid hexyl ester l 0 F 584 HOX (3-Fluoro-2-hydroxy-phenyl)-C13H18FN03 F, G, H 255. 29 255. 6 o carbamic acid hexyl ester \ FNH zozo F 585 HO Br (5-Bromo-3-fluoro-2-hydroxy- 0 phenyt)-carbamic acid hexyl ester F F zozo ZU 586 HO (3, 4-Difluoro-2-hydroxy-phenyl)-C1 3H17F2N03 F, G, H 273. 28 273. 6 \ carbamic acid hexyl ester OH 0 Oh NN 2- [3- (3, 5-Dichloro-2-hydroxy-4- 587 | methyl-phenyl)-ureido]-4-methyl-C1 6H22C12N204 A 377. 26 377. 1 g 4 pentanoic acid ethyl ester cl OH N N 2- [3- (3, 5-Dichloro-2-hydroxy- 588 ¢ o 0 ; phenyl)-ureido]-4-methyl-C15H20C12N204 A 363. 24 363. 6 T pentanoic acid ethyl ester ci OH Cl N 2- [3- (3-Chloro-2-hydroxy-phenyl)- 589 ureido]-4-methyl-pentanoic acid C15H21C1N204 A 328. 79 329. 1 0 0 ethyl ester OH F_, (N y N 2- [3- (3-Fluoro-2-hydroxy-phenyl)- 590 0 ureido]-4-methyl-pentanoic acid C15H21FN204 A 312. 34 312. 8 o o ethyl ester L-1 OH F N N 2- [3- (3, 4-Difluoro-2-hydroxy-4- 591 0 phenyl)-ureido]-4-methyl-C15H2OF2N204 A 330. 33 330. 8 F O Ok pentanoic acid ethyl ester ON F N N 2- [3- (5-Bromo-3-fluoro-2- hydroxy-4-methyl-phenyl)- 592 A hydroxy-4-methyl-phenyl ?-C1 5H20BrFN204 A 391. 23 391. 6 w 00sO ureido]-4-methyl-pentanolc acid ethyl ester Bu I OH 2- [3- (3, 5-Dichloro-2-hydroxy-4- 593 ci N N methyl-phenyl)-uxeido]-3-phenyl-C19H20C12N204 A 411. 28 411. 1 propionic acid ethyl ester 0 0 0'--, ci oh OH H 2- [3- (3, 5-Dichloro-2-hydroxy- 594 m I N N phenyl)-ureido]-3-phenyl-C18H18C12N204 A 397. 25 397. 6 II propionic acid ethyl ester /o 0 0 ci 0 H 2- [3- (3-Chloro-2-hydroxyphenyl)- 595 N N ureido]-3-phenyl-propionic acid C18H19CIN204 A 362. 81 363. 0 XY T t ethyl ester ° o o 2- [3- (3-Fluoro-2-hydroxy-phenyl)- OH 596 F N N ureido]-3-phenyl-propionic acid C18H19FN204 A 346. 35 346. 7 ethyl ester ° oWo\ 2- [3- (3, 4-Difluoro-2-hydroxy- 597 F 1 NN J phenyl)-ureido]-3-phenyl-C18H18F2N204 A 364. 34 364. 8 propionic acid ethyl ester 0 o ou OH 2- [3- (5-Broma-3-fluoro-2- 598 F__ (N N hydroxy-phenyl)-ureido]-3-phenyl-C18Hl8BrFN204 A 425. 25 425. 6 II propionic acid ethyl ester 4 °. Br OH H cl N 0 3, 5, 5-Trimethyl-hexanoic acid 599 (3, 5-dichloro-2-hydroxy-4-methyl- C16H23C12N02 C, E 332. 27 332. 5 phenyl)-amide Structure Chemical name Formula Synthesis MolWeight MS data methods OH N 0 CI N O 3, 5, 5-Trimethyl-hexanoic acid 600 (3, 5-dichloro-2-hydroxy-phenyl)-C15H21Cl2N02 C, E 318. 24 318. 5 amie ci OH H cul N 0 601 3, 5, 5-Trimethyl-hexanoic acid (3-C15H22CIN02 C, E 283. 79 284. 0 chloro-2-hydroxy-phenyl)-amide OH H F N O 602 3, 5, 5-Trimethyl-hexanoic acid (3-C15H21FN02 C, E 267. 34 267. 7 uU2 \. ,,, ., d3tiZlt<J\U2 L, c. 26/. J4 26/./ fluoro-2-hydroxy-phenyl)-amide OH H N O 3, 5, 5-Trimethyl-hexanoic acid 603 I (3, 4-difluoro-2-hydroxy-phenyl)- Ci5H21F2N02 C, E 285. 33 285. 7 amide OH H 0 3, 5, 5-Trimethyl-hexanoic acid (5- 604 V bromo-3-fluoro-2-hydroxy-ClSH21BrFN02 C, E 346. 24 346. 5 Br phenyl)-amide HN 1-tert-Butyl-3- [3-chloro-5- (3- J followed by 605 cyclohexyl-ureido)-2-hydroxy-C18H27CIN403 A 382. 88 383. 4 k R Ac NN/CI H H OH NU HN-'O 1-L3-Chloro-5- (3-cyclohexyl- J followed by 606 ureido)-2-hydroxy-phenyl]-3-C22H35CIN403 A 438. 99 439. 8 (1, 1, 3, 3-tetramethyl-butyl)-urea N'k N#ci H H OH han- i 1- {3-Chloro-5- [2- (4-chloro- /HN-'0 phenylsulfanyl)-benzylamino]-4-J followed by 516. 48 517. 4 607 " hydroxy-phenyl}-3-cyclohexyl-D urea N cri OU HN ho-v WJ H J HN/O 608 \ HN amino]-5-chloro-4-hydroxy-C26H28C1N302 J followed by q. 49, 97 450. 9 phenyl}-3-cyclohexyl-urea N ci H4-- OH Han-v HAN-'O 1- (3-Chloro-5- (2-chloro-6-fluoro- J followed bu 609 benzylamino)-4-hydroxy-phenyl]-C20H22C12FN302 D 426. 31 426. 4 3-cyclohexyl-urea I w H c H OH N N / HN\ O 1-tert-Butyl-3- [3-chloro-2- 610 Y hydroxy-5- (3-phenethyl-ureido)- C20H25C1N403 J followed by q. 04. 89 404. 9 HN phenyl]-urea OH OH ! a-o N T09 HNO L3-Chlora-2-hydroxy-5- (3- 611 phenethyl-ureido)-phenyl]-C20H24C1N304 J followed by 405. 88 406. 8 HN carbamic acid isobutyl ester OH H CI NO O [3-Chloro-2-hydroxy-5- (3- 612 phenethyl-ureido)-phenyl]-C20H24CIN304 JfolloGedby 405. 88 406. 8 HN carbamic acid sec-butyl ester i OH H 0 I 0 Cyclopentanecarboxylic acid [3- HN O J followed by 613 Y chloro-2-hydroxy-5- (3-phenethyl- C21H24C1N303 J 401. 89 401. 9 HN ureido)-phenyl]-amide OH OH OU PO '0 I/O Cyclohexanecarboxylic acid [3- 614"N (° chloro-2-hydroxy-5- (3-phenethyl- C22H26C1N303 J folloC ed by q. 15. 92 415. 9 HN ureido)-phenyl]-amide OH N N CI H H i i. i i/O I 1-tert-Butyl-3- {3-chloro-2- J followed by 615 HN o hydroxy-5- [3- (1, 1, 3, 3-tetramethyl- C20H33C1N403 A 412. 95 413. 8 butyl)-ureido]-phenyl}-urea HN OH H cil, N O ° {3-Chloro-2-hydroxy-5- [3- 616 HN (1, 1, 3, 3-tetramethyl-butyl)- C20H32CIN304 J followed by 413. 94 413. 8, [ureido]-phenyl}-carbaimc acid G HN isobutyl ester OH N CI N'O ° {3-CMoro-2-hydroxy-5- [3- 617 HN o (1, 1, 3, 3-tetramethyl-butyl)- J folloG ed by q. 13. 94 414. 1 ureido]-phenyl}-carbamic acid sec-G HN butyl ester OH CI tS ° Cyclopropanecarboxylic acid {3- 618 HN 0 chloro-2-hydroxy-5- [3- (1, 1, 3, 3-C19H28ClN303 J followed by 381. 90 381. 9 S 618 t tetramethyl-butyl)-ureido]- HN phenyl}-amide t OH CI N cl, Nl,, C ° Cyclobutanecarboxylic acid {3- chloro-2-hydroxy-5- [3- (1, 1, 3, 3- J followed by tetramethyl-butyl)-ureido]-C phenyl}-amide OH | H 1% -iro C N Cyclopentanecarboxylic acid {3- 620 . o chloro-2hydroxy-5- [3- (U. 3, 3- C21H32CIN303 J followed by 409. 95 410. 1 620 tetramethyl-butyl)-ureido]-C HN phenyl}-amide tt OH H CI N Cyclohexanecarboxylic acid {3-S 621 HNo chloro-2-hydroxy-5- [3- (1, 1, 3, 3- J followed by tetramethyl-butyl)-ureido]-C HN tt phenyll-amide OH a HJ T r o i HN o N- [3- (3-tert-Butyl-ureido)-5- 622 HN¢O chloro-4-hydroxy-phenyl]-3-C20H24C1N303 A 389. 88 389. phenyl-propionamide O l OH OH) ICI 0 [3-Chloro-2-hydroxy-5-(3-phenyl-L followed by 623 HN o propionylamino)-phenyl]-carbamic C20H23C1N204 G 390. 86 390. 8 acid isobutyl ester OH H cl nu HN o [3-Chloro-2-hydroxy-5- (3-phenyl- L followed by 624 propionylamino)-phenyl]-carbamic C20H23CIN204 G 390. 86 390. 8 acid sec-butyl ester i OH ! H A /o HN o Cyclopropanecarboxylic acid [3- 0 625 chloro-2-hydroxy-5- (3-phenyl- C19H19CIN203 L foll C ed by 358. 82 358. 9 propionylamino)-phenyl]-aaude OH H ci N 0 0 - hen 1-C20H21C1N203 C 372. 85 373. 8 626 chloro-2-hydroxy-5- (3-phenyl- followed by propionylamino)-phenyl]-amide OH H CIN Iso Ç t Cl t N X t 627 chloro-2-hydroxy-5- (3-phenyl- C21H23C1N203 L 386. 87 386. 8 propionylamino)-phenyl]-amide OH H ' 0 0 Cyclohexanecarboxylic acid [3-L followed by 628"N o chloro-2-hydroxy-5- (3-phenyl- C22H24CIN203 L 400. 90 401. 8 propionylamino)-phenyl]-amide OH N N 1-Cyclopentyl-3- (3, 5-dichloro-2- 629 t 2 (n hydroxy-$methyl-phenyl)-C13H16Cl2N20S I 319. 25 319. 7 / thiourea ci OH 630 N 2- [2- (4-Chloro-phenylsulfanyl)- C19Hl6CINOS D 341. 85 342. 3 s benzylaminol-phenol ci -9 i HN l-Benzyl-3- {3-chloro-5-[2-(4- 631 > chloro-phenylsulfanyl)-C27H23C12N302S J followed by 524. 46 525. 1 j n UN u benzylamino]-4-hydroxy-phenyl}-D ursa \ N I CI OH /OH HN 1- {3-Chloro-5- [2- (4-chloro- 632 C/HN-'O phenylsulfanyl)-benzylamino-4-C28H25CI2N302S J followed by 538. 49 539. 1 hydroxy-phenyl}-3-phenethyl-urea ~ OH Oh CUL /OU ^/cri HN\ I 1- {3-Chloro-5- [2- (4-chloro- Cl HNXO phenylsulfanyl)-benzylamino]-4-C26H20C13N302S J followed by 544. 88 545. 5 hydroxy-phenyl}-3- (4-chloro- D phenyl)-urea ci H /OH HN r HN/O Ethtnesulfonic acid [3-chloro-5-J followed by 634 (3-cyclohexyl-ureido)-2-hydroxy-C15H22C1N304S B 375. 9 376. 1 o JXcB phenyl]-amide OH 3 OHM H# OU HN_ v < N- 3-Chloro-5- (3-cyclohexyl- J followed by 635 ureido)-2-hydroxy-phenyl]-3, 3- C19H28CIN303 c 381. 90 382. 2 o I w dimethyl-butyramide OH OH OH OH H H cl ZON I/O I' 636 1- (5-Benzothiazol-2-yl-3-chloro-2- C18Hl8CIN302S K followed by 375. 9 376. 1 hydroxy-phenyl)-3-tert-butyl-urea A s N OH ci !"H K followed by74no cl t 1-(5-Benzothiazol-2-yl-3-chloro-2-C21H16CIN302S K followed by 409. 9 410. 1 hydroxy-phenyl)-3-benzyl-urea A SON OH OH CI OH N 638 1- (5-Benzothiazol-2-yl-3-chloro-2- C22H18C1N302S K followed by 423. 9 424. 1 . hydroxy-phenyl)-3-phenethyl-urea A OH H H C ! N 1/N s 1- (5-Benzothiazol-2-yl-3-chloro-2- 639 A hydroxy-phenyl)-3-isopropyl-C17H16CIN30S2 I 377. 9 S N thiourea 0) OH H H CI NN s I 1- (5-Benzothiazol-2-yl-3-chloro-2- 640 hydroxy-phenyl)-3-tert-butyl-C18H18CIN30S2 I 391. 9 392. 1 s N thiourea --. 0 HN 3, 5, 5-Trimethyl-hexanoic acid (5- K foll C ed by q. 17. 0 417. 2 641 l i benzothiazol-2-yl-3-chloro-2-C22H25C1N202S N \= (hydroxy-phenyl)-amide Ci cl S H N- (5-Benzothiazol-2-yl-3-chloro- 642 I I 2-hydroxy-phenyl)-3-phenyl-C22H17CIN202S K followed by 408. 9 409. 2 propionamide OH OH OH 643 N N 1- (2-Hydroxy-4-methyl-phenyl)-3- C13H2oN202 A 263. 31 256. 9 pentyl-urea 0 1-I H Biphenyl-4-carboxylic acid (3, 5- 644 cw sHX dichloro-2-hydroxy-4-methyl-C20HlSCl2N02 C or E 372. 24 372. 6 phenyl)-amide ci o oh OH Y 645 H v Biphenyl-4-carboxylic acid (3, 5- C20H15C12N02 C or E 358. 22 358. 5 dichloro-2-hydroxy-phenyl)-amide Cl ci Oh H ci N, j 2, 4-Dichloro-6- [ (furan-2- C12H11CI2N02 D 272. 13 272. 6 ylmethyl)-amino]-3-methyl-phenol cl OH o H 2, 4-Dichloro-6- [ (furan-2- C11H9C12N02 D 258. 10 258. 4 ylmethyl)-amino]-phenol ci Oui oh o 648 F N 2, 3-Difluoro-6- [ (furan-2- C11H9F2N02 D 225. 19 225. 7 ylmethyl)-amino]-phenol F Oh ci N 2, 4-Dichloro-3-methyl-6- (2- 649 t ! i'triGuoromethyl-benzylamino)-C15H12C12F3NO D 350. 16 350. 5 cl3 phenol Ci OU H r Cl 2 4-Dichloro-6-(2-tl ifluoromethyl-C14HIOCI e 9 benzylamino)-phenol cl OU 651 F N 2, 3-Difluoro-6- (2-trifluoromethyl- benzylamino)-phenol C fus cl CI _ AN HN 4CI 1-{3-Chloro-5-[2-(4-chloro- 652 C HN''O phenylsulfanyl)-benzylamino]-4-J followed by t j ! hydroxy-phenyl}-3- (2, 6-dichloro- D hydroxy-phenyl}-3- (2, 6-dichloro- D wu ft pyndm-4-yl)-urca I \ H CI /OH OH H H ou ZON 1- (5-Benzothiazol-2-yl-3-chloro-2- 653 hydroxy-phenyl)-3-cyclopentyl-C19Hl8ClN3OS2 1 403. 95 404. 6 S/% N thiourea \/ po HAN- L 1-{3-Chloro-5-[2-(4-chloro- 654 HN"O phenylsu-Ifanyl)-benzylarninol-4-C24H24Cl2N403S f followed by 519. 44 520. 1 hydroxy-phenyl}-3-morpholn-4-D y-urgea ! i ! i yl-urea \ N) +CI OH OH 655 CI I \ 6-Benzylamino-2, 4-dichloro-3- C14H13C12NO D 282. 17 282. 7 methyl-phenol Ci OH N N-, N 1- [2- (IH-Benzoimidazol-2-yl)- 656 !) ! !'y\ ethyl]-3- (3, 5-dichloro-2-bydroxy- C17H16C12N402 A 379. 24 379. 9 4-methyl-phenyl)-urea _ Cl OH H H ci No I i S 1- (5-Benzothiazol-2-yl-3-chloro-2- 657 hydroxy-phenyl)-3-cyclopentyl-C19H18ClN30S2 ov e y 403. 95 404. 6 s N thiourea b-4 0OH H N 1- [5-Chloro-2-hydroxy-3- (2- 658 Ll I s phenylsulfanyl-benzylamino)-C21H18CIN02S D 383. 89 384. 4 phenyl]-ethanone / cri N 1- [5-Chloro-2-hydroxy-3- (2-p- 659 tolylsulfanyl-benzylamino)-C22H20CIN02SD397. 92 398. 2 phenyl]-ethanone cri ci lu O OU N 1-t5-Chloro-3- [2- (4-chloro- 660 , S phenylsulfanyl)-benzylamino]-2-C21H17C12N02S D 418. 34 418. 9 hydroxy-phenyl}-ethanone cl cl 0 OH w I 1- {5-Chloro-2-hydroxy-3- [2- (4- 661 nitro-phenylsulfanyl)- benzylamino]-phenyl}-ethanone cl N02 0 oh O oh N 1- {5-Chloro-2-hydroxy-3- [2- (4- 662 ll l methoxy-phenylsulfanyl)-C22H20ClN03S D 413. 92 414. 3 benzylamino]-phenyl)-ethanone ou OMe O oh N 1-15-Chloro-3- [2- (2-chloro- 663 0, J s phenylsulfanyl)-benzylamino]-2-C21H17C12N02S D 418. 34 418. 9 hydroxy-phenyl}-ethanone cul 0 OH H N 1-15-Chloro-3- [2- (3-chloro- w 664 | phenylsulfanyl)-benzylanuno]-2-C21H17C12N02S D 418. 34 418. 8 s ^/ci hyxy-phenyl}-ethanone cul O oh H N 1-15-Chloro-3- [2- (3, 4-dichloro- 665 W J s a phenylsulfanyl)-benzylamino]-2-C21H16Cl3N02S D 452. 78 453. 2 hydroxy-phenyl}-ethanone Ci I ci 0 OH N N- (4-f2- [ (3-Acetyl-5-chloro-2- 666 , S hydroxy-phenylamino)-methyl]-C23H21CIN203S D 440. 94 441. 4 phenylsulfanyl}-phenyl)-acetamide ci '-NHAo Cl (+NHAc 0 oh N 1-15-Chloro-2-hydroxy-3- [2- 667 (quinolin-7-ylsulfanyl)-C24Hl9CIN202S D 434. 94 435. 3 1 < benzylamino]-phenyl}-ethanone ci N02 N0 0 OH ß 1-{5-Chloro-3-[2-(4-chloro- 668) +, NH phenylsulfanyl)-5-nitro-C21H16C12N204S D 463. 33 463. 9 benzylamino]-2-hydroxy-phenyl}- ethanone ci I ct ci N0 O OH H 1- [5-Chloro-2-hydroxy-3- (5-nitro- 669 JA N t 2-p-tolylsulfanyl-benzylamino)-C22H19CIN204S D 442. 92 443. 3 phenyl]-ethanone ci NH2 0 oH H 1- {3- [5-Amino-2- (4-chloro- 670 w N I phenylsulfanyl)-benzylamino]-5-C21H18C12N202S D 433. 35 433. 6 chloro-2-hydroxy-phenyl}- ethanone cl cri 1- {5-Chloro-3- [2- (4-chloro- 671 /o2S benzenesulfonyl)-benzylamino]-2-C21H17C12N04S D 450. 33 448. 5 hydroxy-phenyl}-ethanone ci cl OH 672 4- [2- (4-Chloro-phenylsulfanyl)- C19H16CIN02S D 357. 85 358. 4 Ho s w benzylamino]-benzene-1, 3-diol cri OH OH OH OH CI N N . N N CI 673''TSYYT l, 6-Di- (35-Do-ydroxy-4- c22H26C14N404 AfoUowedby i o methyl-phenyl)-3-hexyl-urea E1 ci H H 3_ [3- (3-Chloro-4-hydroxy-phenyl)- H H 674 jfT Y 3- (3-Chloro-4-hydroxy-phenyl). ci2H15C ! N204 A 286. 71 286. 9 Ho ureido]-propionic acid ethyl ester a 170 H H 1_ (3-Chloro-4-hydroxy-phenyl)-3- 675 C12H17C1N202 A 256. 73 256. 9 a | pertyl-urea p HA Cl N N \ I 1-Benzyl-3- (3-chloro-4-hydroxy- 676 T 1-Benzyl-3-(3-chloro-4-hydroxy-C14H13C1N202 A 276. 72 276. 9 0 phenyl)-urea HA cl / 677 \ I 1- (3-Chloro-4-hydroxy-phenyl)-3- HO) 9I (2-methyl-benzyl)-urea HOIR ho Cl H H H H /o , C15Hi5C1N202 A 290. 75 291. 2 Ho phenethyl-urea cl H H H H t) 679 o C15H23C1N202 A 298. 81 299. 4 < Ho (1, 1, 3, 3-tetramethyl-butyl)-urea cl HAN H 680 jOT Y f l-tert-Butyl-3- (3-chloro-4- C11H15C1N202 A 242. 70 243. 0 680 HOX hydroxy-phenyl)-urea C ! HH 681 N,-"O 1- (3-Chloro-4-hydroxy-phenyl)-3- C14Hl9ClN202A282. 77 283. 1 681 o cyclohexylmethyl-urea H Y Y ho CI Cl CF3 rw Y 1-(3-Chloro-4-hydroxy-phenyl)-3-C15H12ClF3N202 A 344. 72 345. 0 4 o (4-tntluoromethyl-benzyi)-urea HO C ! H H 3 NN) qzCI 1-(3-Chloro-3-hydroxy-phenyl)-3-C13H9Cl3N202 A 331. 59 331. 9 683 , o , C13H9C13N202 A 331. 59 331. 9 H (3, 5-dichloro-phenyl)-urea Ci ci H H 1- (3-Chloro-4-hydroxy-phenyl)-3- C13H10C12N202 A 297. 14 297. 7 684 Ho, o/i (4-chloro-phenyl)-urea cl H H oj : : NyN,, 685 Nslí q 1-(3-Chloro-4-hydroxy-phenyl)-3-C14HlOClF3N202 Å 330. 69 331. 0 (4-trifluoromethyl-phenyl)-urea N N CI H H N'N 1- (3-Chloro-4-hydroxy-phenyl)-3- 686 , o C13H17CiN2o2 A 268. 74 269. 1 ho cyclohexyl-urea o H H I N'N I j 1- (3-Chloro-4-hydroxy-phenyl)-3- C14H1oC1F3N203 A 346_69 346. 9 HO ocF (4-lxifluoromethoxy-phenyl)-urea a CI H H NN>q 1-(3-Chloro-4-hydroxy-phenyl)-3-C14HlOCIN302 A 287. 70 287. 9 6gg , o , C14H1oC1N302 A 287. 70 287. 9 HO CN (4-cyano-phenyl)-urea o H H O 689 0 C (I-Benzo [1, 3] dioxol-5-yl-3-(3-C 14H1 l C1N204 A 306. 70 306. 9 68 HoXI chloro-Shydroxy-phenyl)-urea HA Cl H H N N 690 1t s 1-(3-Chloro-4-hydroxy-phenyl)-3-C14H13CIN202 A 276. 72 276. 9 HOw o-tolyl-urea Cl H H N N ome 691 ,lo', C14H13CiN2o3 A 292. 72 292. 9 o Xl (3-methoxy-phenyl)-urea Cri H H N N 692 1N) 6 1- (3-Chloro-4-hydroxy-phenyl)-3- C15Hl5CIN202A 290. 75 290. 9 Ho., q N 0 (2, 6-dimethyl-phenyl)-urea Ho CI H H 693 ij ILJ. l (3-Chloro-4-hydroxy-phenyl)-3- ci6H17CtN205 A 352. 77 353. 2 H 0 OMe (3, 4, 5-trimethoxy-phenyl)-urea Cl OMe CI OMe H H 694 Ny 1- (3-Chloro-4-hydroxy-phenyl)-3- C17Hl3CIN202A312. 75 313. 1 o . naphthalen-1-yl-urea Ho Cl 695 N NH 1-Adamantan-1-yl-3- (3-chloro-4- c17H21CIN202 A 320. 82 321. 4 HOJS ! f n hydroxy-phenyl)-urea o HA ci H H H H 696 N II N C19H15C1N2o3 A 354. 79 354. 9 Ho o (4-phenoxy-phenyl)-urea ci H H 697 jO"TT l-Chloro-4-hydroxy-phenyl)-3-ci3HlldN202 A 262. 70 263. 2 HO< phenyl-urea C ! H H Cl H N O 3-[3-(3, 5-Dichloro-4-hydroxy- 698 D o o phenyl)-ureido]-propionic acid C12H14C12N204 A 321. 16 321. 9 HO ethyl ester ci H H CI Nu N 699 1- (3, 5-Dichloro-4-hydroxy- C12Hl6Cl2N202 A 291. 17 292. 0 Ho phenyl)-3-pentyl-urea ci cri CI N N \ I 1-Benzyl-3- (3, 5-dichloro-4- 700 drox-hen 1)-urea C14H12C12N202 A 311. 16 312. 0 700 Y Y P Y HO Cl ci N N w I 1- (3, 5-Dichloro-4-hydroxy- HOJ ? phenyl)-3-(2-methyl-benzyl ?-urea HO o H H H H 702 cl I/N/N I % 1_ (3, 5-Dichloro-4-hydroxy- C15H14CI2N202 A 325. 19 325. 9 0 Ha phenyl)-3-phenethyl-urea Ci H H -NyN_f,-* 1- (3, 5-Dichloro-4-hydroxy- 703 0 phenyl)-3- (1, 1, 3, 3-tetramethyl- C15H22C12N202 A 333. 25 334. 0 HO T butyp-urea cl H H ! 704 1-tert-Butyl-3- (3, 5-dichloro-4.- C11H14C12N202 A 277. 15 277. 8 hydroxy-phenyl)-urea Ci Ny N,-"O 1- (3, 5-Dichloro-4-hydroxy- 705 Y hen 1-3 c clohex lmeth 1-urea C14H18C12N202 A 317. 21 318. 1 HO HO cl CF3 H 1- (3, 5-Dichloro-4-hydroxy- 706 J)) T phenyl)-3- (4-trifluoromethyl- C15H11C12F3N202 A 379. 16 379. 8 HO benzyl)-urea cl H H Cl HNN Cl 1-(3, 5-Dichloro4-hydroxy- 707 oD ° W phenyl)-3-(3, 5-dichloro-phenyl)-C13H8C14N202 A 366. 03 366. 9 Ho ures ci cl N N H H 1- (3, 5-Dichloro-4-hydroxy- C13H9C13N202 A 331. 58 331. 9 708 0 phenyl)-3- (4-chloro-phenyl)-urea Cl H H Ny N 1- (3, 5-Dichloro-4-hydroxy- 709 , o , phenyl)-3- (4-trifluoromethyl- C14H9C12F3N202 A 365. 13 365. 9 phenyl)-urea C ! H H 710 N N 1_ (3, 5-Dichloro-4-hydroxy- 710 , p C13H16C12N202 A 303. 18 304. 0 HO phenyl)-3-cyclohexyl-urea Cl H H 1- (3, 5-Dichloro-4-hydroxy- 711 , o , phenyl)-3- (4-trifluoromethoxy- C14H9C12F3N203 A 381. 13 381. 8 HO T OCFs phenyl)-urea w Cl H H 712 y 1- (3, 5-Dichloro-4-hydroxy- HO CN phenyl)-3- (4-cyano-phenyl)-urea C ! H H O 713 1-Benzo [1, 3] dioxol-5-yl-3- (3, 5- C14HlOCl2N204 A 341. 15 341. 7 o dichloro-4-hydroxy-phenyl)-urea HO H H N N CI N. - N HO y 1- (3, 5-Dichloro-4-hydroxy- C14Hl2Cl2N202 A 311. 16 311. 8 HOe phenyl)-3-o-tolyl-urea ci N N, ome 1 : : , 1- (3, 5-Dichloro-4-hydroxy- 715 lXJ õ J phenyl)-3-(3-methoxy-phenyl)-C14H12C12N203 A 327. 16 327. 5 HO urea o H H N N) 6 1- (3, 5-Dichloro-4-hydroxy- 716 D o JtJ phenyl)-3-(2, 6-dimethyl-phenyl)-ClSH14C12N202 A 325. 19 325. 6 HO urea ci H H Cl/< N N <OMe 1-(3, 5-Dichloro-4-hydroxy- 717 0 phenyl)-3- (3, 4, 5-trimethoxy- C16H17C12N205 A 387. 21 387. 6 HO Me phenyl)-urea Ci OMe / H H 718 CI/N/N/1- (3, 5-Dichloro-4-hydroxy- C17H12CI2N202 A 347. 20 347. 6 >1 phenyl)-3-naphthalen-1-yl-urea HO CI H I-Adamantan-1-yl-3- (3, 5-dichloro- Hon 4-hydroxy-phenyl)-urea o HO ci H H Cl N N 1 (3, 5-Dichloro-4-hydroxy- 720 on <043 phenyl)-3-(4-phenoxy-phenyl)-C19H14C12N203 A 389. 23 389. 6 Who l urea Ct H H 7 I N/N I 1- (3, 5-Dichloro-4-hydroxy- C13H10C12N202 A 297. 14 297. 7 721/o/phenyl)-3-phenyl-urea HO cul CL 722 N N a 3- [3- (4-Hydroxy-3-nitro-phenyl)- {H H j oreido]-propionic acid ethyl ester /o 0 HO H H 723 2N \ N N- (4-Hydroxy-3-nitro-phenyl)-3-C12H17N304 A 267. 28 267. 9 pentyl-urea HO 724 OZN N N 1-Benzyl-3- (4-hydroxy-3-nitro- C14H13N304 A 287. 27 287. 9 HO m Ho 725 zN N N 1-t-Hyc'oxy-3-nitro-phenyl)-3-C15H15N304 A 301. 30 301. 8 (2-methyl-benzyl)-urea HO ° HO 02N N N 1- (4-Hy (Iroxy-3-nifTo-phenyl)-3- 726 /lol phenethyl-urea Ho \ Nu N /1- (4-Hydroxy-3-nitro-phenyl)-3- _ HOX (1, 1, 3, 3-tetramethyl-butyl)-urea HO 0, N NN 1-tert-Butyl-3- (4-hydroxy-3-nitro- CllHl5N304A253. 25 253. 8 phenyl)-urea Holz HYH 1-Cyclohexylmethyl-3- (4- 729 ! hydroxy-3-mtro-phenyl)-urea o HO HO CFS 730 H"1- (4-Hydroxy-3-nitro-phenyl)-3- 355. 8 ( (4-trifluoromethyl-benzyl)-urea o. HA HO X)"y 1- (3, 5-Dichloro-phenyl)-3- (4- C13H9Cl2N304A342. 13 342. 7 o , C13H9C12N3o4 A 342. 13 342. 7 Ho hydroxy-3-nitro-phenyl)-urea cri H H O, N NN 1- (4-Chloro-phenyl)-3- (4-hydroxy- C13HIOCIN304A307. 69 308. 4 H H 3-nitro-phenyl)-urea Ho HO 733 NN 1- (4-Hydroxy-3-nitro-phenyl)-3- C14HlOF3N304A341. 24 341. 8 0 (4-trifluoromethyl-phenyl)-urea HO CA HO 734 NN 1-CyClohexyl-3- (4-hydroxy-3- nitro-phenyl)-urea HO HO 735 YYYY H4-Hydroxy-3-nitro-phenyl)-3-ci4H10P3N305 A 357. 24 357. 9 , o , (4-trifluoromethoxy-phenyl)-urea HO"-'-OCFs HO 736 NN 1- (4-Cyano-phenyl)-3- (4-hydroxy- J o L*. . L 3-mtn)-phcnyl)-urea HO CON H 737 I Nt I 0 1-Benzo [l, 3] dioxol-5-yl-3-(4-C14HllN306 A 317. 25 317. 9 737 H H hyoroxy-3-n tro-phenylfurea HO - 0 0 C (hydroxy-3-nitro-phenyl)-urea H H /o/ Ho-J HO 739 °2NA NNA OMe 1-(4-Hydroxy-3-nitro-phenyl)-3-C14H13N305 A 303. 27 303. 8 o L (3-methoxy-phenyl)-urea Ho H H 740 N N 1- (2, 6-Dimethyl-phenyl)-3- (4- 740 ,' ( C15H15N304 A 30130 301. 9 HO « HO HO OzN N N OMe 0 C16Hl7N307A 363. 32 364. 0 Ho onze (3, 4, 5-trimethoxy-phenyl)-urea OMe 742 o2N N N, (1- (4-Hydroxy-3-nitro-phenyl)-3- c17H13N304 A 323_30 323. 9 naphthalen-1-yl-urea y L 743 H l-Adamantan-l-yl-3-(4-hydroxy-C17H21N304 A 331. 37 331. 9 o2N, N NH 3-nitro-phenyl)-urea Z"Y 0 hou HOX 0, N N N (4-Hydroxy-3-nitro-phenyl)-3- HO82 C19Ht5N305 A 365. 34 366. 0 H H 745 1 xv-3-nitro-phenyl)-3-C13HllN304 A 273. 24 273. 9 J o phenyl-urea H H 746 FA NN fO 3-[3-(3-Fluoro-4-hydroxy-phenyl)-C12H15FN204 A 270. 26 270. 6 /o o ureido]-propionic acid ethyl ester HO H H 1- (3-Fluoro-4-hydroxy-phenyl)-3- r 747 o pentyl-urea C12H17FN202 A 240. 27 240. 5 Ho F N N \ 1-Benzyl-3- (3-fluoro-4-hydroxy- HO"-- 748 AJ l-Benzyl-3- (3-Huoro-4-hydioxy- ci4H13FN202 A 260. 26 260. 8 HOD phenyl)-urea L. o 749 F N N. v% 1- (3-Fluoro-4-hydroxy-phenyl)-3- (2-methyl-benzyl)-urea ho HO F NU F ^ N N n n 1_ (3-Fluoro-4-hydroxy-phenyl)-3- Ci5H15FN202 A 274. 29 274. 6 , , phenethyl-urea HO- F N N 1- (3-Fluoro-4-hydroxy-phenyl)-3- HO) a 0 (1, 1, 3, 3-tetramethyl-butyl)-urea HA' H H F N N 1-tert-Butyl-3- (3-fluoro-4- . 1 ! J o'hydroxy-phenyl)-urea HOI v H H [1 F N N 0 1-(3-Fluoro-4-hydroxy-phenyl)-3-C14H19FN202 A 266. 31 266. 7 cyclohexylmethyl-urea 0 Ha _ HO CF3 754 N N 1-(3-Fluoro-4-hydroxy-phenyl)-3-C15H12F4N202 A 328. 26 328. 4 (4-trifluoromethyl-benzyl)-urea /a Ho H H 755-) : r 0 1- (3-Fluoro-4-hydroxy-phenyl)-3- C13H9Ct2FN202 A 315. 13 315. 5 Ho (3, 5-dichloro-phenyl)-urea o HO 56 F N N 1-(3-Fllloro-4-hydroxy-phenyl)-3-C 13HlOCIFN202 A 280. 68 281. 1 7 D o 4Xc (4-chloro-phenyl)-urea HO//CI H H F Nu N 1- (3-Fluoro-2-hydroxy-phenyl)-3- C14H10F4N202 A 314. 24 314. 6 /o / (4-trifluoromethyl-phenyl)-nrea HO CFs -HH 1- (3-Fluoro-4-hydroxy-phenyl)-3- C13H17FN202 A 252. 28 252. 6 cyclohexyl-urea Ho HA H H F\ ^'N N ^ 1- (3-Fluoro-4-hydroxy-phenyl)-3- C14H10FF3N203 A 330. 23 330. 5 1 , , (4-trifluoromethoxy-phenyl)-urea HO OFFS HO F\ ^'N N 1- (3-Fluoro-4-hydroxy-phenyl)-3- C14H10FN302 A 271. 25 271. 5 760 o'L L (4-cyano-phenyl)-urea HO CON HO 761 F I N I ° 1-Benzo [1, 3] dioxol-5-yl-3- (3- C14H11FN204 A 290. 25 290. 7 Y fluoro-4-hydroxy-phenyl)-urea HA | H H _ 4 762 \ C14H13FN202 A 260. 26 260. 5 Ji J o J o-tolyl-urea HH F OMe 1-(3-Fluoro4-hydroxy-phenyl)-3-C14H13FN203 A 276. 26 276. 5 763 3-methoxy-phenyl)-urea HO, F N N 1- (3-Fluoro-4-hydroxy-phenyl)-3- 764 C15H15FN202 A 274. 29 274. 7 (2, 6-dimethyl-phenyl)-urea Ha H H ? f 765 F N'N (j onne 1_3-Fluoro-4-hydroxy-phenyl)-3-C16H17FN205 A 336. 31 336. 6 'oj , J o c- <-i\ L. lDtli7bJN2U5 A jjo. ji jjo. o Ho oMe (3, 4, 5-trimethoxy-phenyl)-urea OMe F N N/ 1- (3-Fluoro-4-hydroxy-phenyl)-3- 766 ! t naphthalen-1-yl-urea Ha 767 H 1-Adamantan-1-yl-3- (3-fluoro-4- C17H21FN202 A 304. 36 304. 6 F N y NH hydroxy-phenyl)-urea HO Ho H H 768 F I N'N I I 1- (3-Fluoro-4-hydroxy-phenyl)-3- HOX ° uoAJ (4-phenoxy-phenyl)-urea « Ho H H F N N F\ ^'N N ^ 1_t3_uoro-4-hydroxy-phenyl)-3-C13H11FN202 A 246. 24 246. 5 . - 1' 769 Ho /lol , phenyl-urea OH NN ^/o 3- [3- (2, 4-Dihydroxy-phenyl)- C12H16N205 A 268. 27 268. 7 tJ ureido]-propionic acid ethyl ester /o 0 HA OH 1- (2, 4-Dihydroxy-phenyl)-3- C12H18N203 A 238. 28 238. 6 lol pentyl-urea HO Ohm N N 1-Benzyl-3- (2, 4-dihydroxy- C14H14N203 A 258. 27 258. 6 HO /o Ho oh N N 1 1- (2, 4-Dihydroxy-phenyl)-3- (2- C15H16N203 A 272. 30 272. 5 HOX meffiyl-benzyl)-urea /o. OH ON N N 1- (2, 4-Dihydroxy-phenyl)-3- Ci5H16N203 A 272. 30 272. 5 HO ° k ' OH OH 775 N N 1- (2, 4-Dihydroxy-phenyl)-3- C15H24N203A280. 36 280. 7 (1, 1, 3, 3-tetramethyl-butyl)-urea HA OH 1-tert-But 1-3- (2, 4-dih drox- II phenyl)-urea y y C11H16N203 A 224. 26 224. 8 /o HA OH 777 N N I-Cyclohexylmethyl-3- (2, 4- C14H2ON203A264. 32 264. 7 dihydroxy-phenyl)-urea /o HO /CF3 OU N N (1- (2, 4-Dihydroxy-phenyl)-3- (4- 778 ifluoromethyl-benzyl)-urea C15H13F3N203 A 326. 27 326. 8 OH HOLZ OH H fi N N C 1- (3, 5-Dichloro phenyl)-3- (2, 4- 9 II CI3H10C12N203 A 313. 14 313. 7 Ho ° dihydroxy-phenyl)-urea OH OU OH C13H11C1N203 A 278. 69 279. 2 dihydroxy-phenyl)-urea HO CRI OH 781 N N 1- (2, 4-Dihydroxy-phenyl)-3- (4- C14HllF3N203A312. 24 312. 8 gl C14H11F3N203 A 312. 24 312. 8 , trifluoromethyl-phenyl)-urea H OH CF3 OU 782 phenyl) ureal 3- (2, 4-dihydroxy- C13H18N203 A 250. 29 250. 8 i o ho OH H H 1- (2, 4-Dihydroxy-phenyl)-3- (4- c14H11F3N204 A 328. 24 328. 7 0 tdfluoromethoxy-phenyl)-urea OC3 OH 784 N 1- (4-Cyano-phenyl)-3- (2, 4- !'dihydroxy-phenylt-urea ho con Oh OH 785 1-Benzo [1, 3] dioxol-5-yl-3- (2, 4- ! !' ! L/dihydroxy-phenyl)-urea OH __. Oh 786 < T A 1-(2, 4-Dihydroxy-phenyl)-3-o-C14H14N203 A 258. 27 258. 7 I o 0 C OH OU N N OMe 1- (2, 4-Dihydroxy-phenyl)-3- (3- 787 C14H14N204 A 274. 27 274. 8 methoxy-phenyl)-urea HO" OH 788 N 1- (2, 4-Dihydroxy-phenyl)-3- (2, 6- C15Hl6N203A272. 30 272. 9 OH HO OH H H N N \ OMe 1_2, 4-Dihydroxy-phenyl)-3- 789 C16Hi8N206 A 334. 32 334. 8 HO OMe (3, 4, 5-trimethoxy-phenyl)-urea OMe OMe OH 790, N N, I 1- (2, 4-Dihydroxy-phenyl)-3- C17H14N203 A 294. 30 294. 9 naphthalen-1-yl-urea HO HO 791 OH H l-Adamantan-1-yl-3- (2, 4- C17H22N203 A 302. 37 302. 8 iio., N b NH dihydroxy-phenyl)-urea O HO OH 792 N N 1- (2, 4-Dihydroxy-phenyl)-3- (4- C19Hl6N204 A 336. 34 336. 9 HOv ° >° phenoxy-phenyl)-urea OH OH OH 793 I phenyl-urea C13H12N203 A 244. 25 244. 7 /o HA H H HO Brß NN (0 3-[3-(3, 5-Dibromo-4-hydroxy- 794 H Jl d o o phenyl)-ureido]-propionic acid C12H14Br2N204 A 410. 06 410. 4 Ho ethyl ester bar H H Br N N 795 Br\ 1- (3, 5-Dibromo-4-hydroxy- C12H16Br2N202 A 380. 08 380. 5 Ho phenyl)-3-pentyl-urea Br 796 H sr N N 1_Benz 1-3-3, 5-Dibromo-4- 796 II y C14H12Bi2N202 A 400. 07 400. 4 o hydroxy-phenyl)-urea HO Br H Hm 797 Ny No 1- (5-Bromo-3-fluoro-2-hydroxy- C15Hl4Br2N202 A 414. 09 414. 5 phenyl)-3- (2-methyl-benzyl)-urea HO BER Br H H Br N N 1- (3, 5-Dibromo-4-hydroxy- C15H14Br2N202 A 414. 09 414. 4 phenyl)-3-phenethyl-urea Br H H r Y oW/1-(3, 5-Dibromo-4-hydroxy- 799 D o phenyl)-3-(1, 1, 3, 3-tetramethyl- C15H22Br2N202 A 422. 16 422. 5 HO butyl)-urea Br H H ! 800 BrCSNN > l-tert-Butyl-3-(3, 5-dibromo-4-C1 lH14Br2N202 A 366. 05 366. 4 , hydroxy-phenyl)-urea 4 Br er N N 1_ (3, 5-Dibromo-4-hydroxy- X o phenyl)-3-cyclohexylmethyl-urea H Br Br /caf3 N N 1- (3, 5-Dibromo-4-hydroxy- y phenyl)-3- (4-trifluoromethyl- C15HllBr2F3N202 A 468. 06 468. 4 HO benzyl)-urea HA Br H H NyNqCl 1- (3, 5-Dibromc)-4-hydroxy 803 v o lJ phenyl)-3-(3, 5-dichloro-phenyl)-C13H8Br2C12N202 A 454. 93 455. 4 HO urea Ho H H Br N N 804 Br>eC 1-(3, 5-Dibromo-4-hydroxy-C13H9Br2CIN202 A 420. 48 420. 7 Ho phenyl)-3-(4-chloro-phenyl)-urea Br H H _ Br N N 1-(3, 5-Dibromo-4-hydroxy- 805 , o , phenyl)-3- (4-trifluoromethyl- C14H9Br2F3N202 A 454. 04 454. 3 Ho T CF phenyl)-urea Br H H Br N N 806 2,) qNYN"o 1- (3, 5-Dibromo-4-hydroxy- Cl3Hl6Br2N202 A 392. 09 392. 5 Xr phenyl)-3-cyclohexyl-urea X Br H H er N N 1-(3, 5-Dibromo-4-hydroxy- w 807 0 phenyl)-3- (4-trifluoromethoxy- C14H9Br2F3N203 A 470. 04 470. 3 phenyl)-urea Br HO Br N N 1- (3, 5-Dibromo-4-hydroxy- C14H9Br2N302 A 411. 05 411. 5 HO phenyl)-3- (4-cyano-phenyl)-urea Br H H 131) , NYN,, ( er N'N 1-Benzo [1, 3] dioxol-5-yl-3- (3, 5- $9 I, p /> C14H10Br2N204 A 430. 05 430. 3 Ho r dibromo-4-hydroxy-phenyl)-urea Br H H Br N. - N 1- (3, 5-Dibromo-4-hydroxy- C14Hl2Br2N202A400. 07 400. 4 Br phenyl)-3-o-tolyl-urea Br H H NyN OMe 1- (3, 5-Dibromo-4-hydroxy- w 811 B'q 0 phenyl)-3- (3-methoxy-phenyl)- C14Hl2Br2N203A416. 06 416. 3 urea Br H H r bo 1 (3, 5-Dibromo-4-hydroxy- 812 v °/phenyl)-3-(2, 6-dimethyl-phenyl)-ClSH14Br2N202 A 414. 09 414. 5 HO T urea Br H H Br) q, NyN_qOMe 1- (3, 5-Dibromo-4-hydroxy- 813 0 phenyl)-3- (3, 4, 5-trimethoxy-C16Hl7Br2N205 A 476. 12 476. 4 Br OMe Br OMe /I Br/N N/1- (3, 5-Dibromo-4-hydroxy- 814 o phenyl)-3-naphthalen-l-yl-urea HO H z bar 815 Br N NH l-Adamantan-l-yl-3-(3, 5-dibromo-C17H20Br2N202 A 444. 16 144. 2 4-hydroxy-phenyl)-urea HO I O HO H H H H Br/N N /1- (3, 5-Dibromo-4-hydroxy- 816 HoXl ° <0<3 phenyl)-3-(4-phenoxy-phenyl)-C19Hl4Br2N203 A 478. 13 478. 3 urea Br H H Bro2N202 A 386. 04 386. 2 1- (3, 5-Dibromo-4-hydroxy- C13H10Br2N202 A 386. 04 386. 2 Ho phenyl)-3-phenyl-urea HO H H NN\ ^'o 3_ [3- (3, 5-Difluoro-4-hydroxy- 818 o"o o phenyl)-ureido]-propionic acid C12H14F2N204 A 288. 25 288. 9 Ho ethyl ester F H H H H 819 F) NN 1-(3, 5-Difluoro-4-hydroxy-C12H16F2N202 A 258. 26 258. 9 HOX phenyl)-3-pentyl-urea F H H i 820 F N'N \ 1-Benzyl-3- (3, 5-difluoro-4- C14H12F2N202 A 278. 25 278. 8 o hydroxy-phenyl)-urea Holz F F F N N \ 1- (3, 5-Difluoro-4-hydroxy- ' o phenyl)-3- (2-methyl-benzyl)-urea Holz F H H \ 1_ (3, 5-Difluoro-4-hydroxy- 822 F'NAfN ¢) 1-(3, 5-Difluoro-4-hydroxy-C15H14F2N202 A 292. 28 292. 9 Ho phenyl)-3-phenethyl-urea F F) (N y N 1- (3, 5-Difluoro-4-hydroxy- r i l 823 0 phenyl)-3- (1, 1, 3, 3-tetramethyl- C15H22F2N202 A 300. 34 300. 5 Ho butyl)-urea F H H j 824 D f T l-tert-Butyl-3-(3, 5-difluoro-4-CllH14F2N202 A 244. 24 244. 3 Ho hydroxy-phenyl)-urea F H H N N N1- (3, 5-Difluoro-4-hydroxy- C14H18F2N202 A 284. 30 284. 6 825 HOFV phenyl)-3-cyclohexylmethyl-urea HA F F caf3 F N N \ 1- (3, 5-Diffuoro-4-hydroxy- 826 I phenyl)-3- (4-trifluoromethyl- C15H11FSN202 A 346. 25 346. 5 benzyl)-urea HA H H H H' F N'N C 1- (3, 5-Difluoro-4-hydroxy- 827 D ° v phenyl)-3-(3, 5-dichloro-phenyl)-C13H8C12F2N202 A 333. 12 333. 3 Ho urea F CRI H H N'N, j 1_ (3, 5-Difluoro-4-hydroxy- C13H9C1F2N202 A 298. 67 298. 9 8 HOX I phenyl)-3-(4-chloro-phenyl)-urea F F H H 829 F, 1- (3, 5-Difluoro-4-hydroxy- w 0 phenyl)-3- (4-trifluoromethyl- C14H9F5N202A332. 23 332. 7 phenyl)-urea F N H 830 0 1- (3, 5-Difluoro-4-hydroxy- C13Hl6] F2N202A270. 28 270. 7 830 , o C13H16F2N202 A 270. 28 270. 7 Ho phenyl)-3-cyclohexyl-urea F H H F NH N 1-(3, 5-DinUoTo-4-hydroxy- w 831-HoD ° X phenyl)-3-(4-tifluoromethoxy-C14H9F2F3N203 A 348. 22 348. 6 phenyl)-urea p H H 832 N N> 1-(3, 5-Difluoro-4-hydroxy-C14H9F2N302 A 289. 24 289. 5 832 H 0 ON phenyl)-3- (4-eyano-phenyl)-urea F H H F., q N y N 833. 0> 1-Benzo, [1, 3] dioxol-5-yl-3- (3, 5- C14HIOF2N204 A 308. 24 308. 5 Ho o difluoro-4-hydroxy-phenyl)-urea F H H F N/N 834 I 1- (3, 5-Difluoro-4-hydroxy- C14H12FZN202 A 278. 25 278. 6 Ho 0 phenyl)-3-o-tolyl-urea F H H 1- (3, 5-Difluoro-4-hydroxy- 835 phcnyl)-3- (3-methoxy-phenyl)- C14Hl2F2N203 A 294. 25 294. 5 H ures H H H H F N N 1- (3, 5-Difluoro-4-hydroxy- 836 0 phenyl)-3- (2, 6-dimethyl-phenyl)- C15Hl4F2N202 A 292. 28 292. 6 H) ure F H H F : qNYN, qOMe 1- (3, 5-Difluoro-4-hydroxy- 837 J' o" phenyl)-3- (3, 4, 5-trimethoxy- C16H17F2N205 A 354. 31 354. 6 phenyl)-urea F OMe H H 838 NyN i- (3, 5-Difluoro-4-hydroxy- C17Hl2F2N202A314. 29 314. 6 phenyl)-3-naphthalcn-1-yl-urea C17H12F2N202 A 314. 29 314. 6 Ho') F 1-Adanantan-1-yl-3- (3, 5-difluoro- t { 839 F HN-NH l-Adamantan-l-yl-3-(3, 5-diíluoro-C17H20F2N202 A 322. 35 322. 7 n o 4-hydroxy-phenyl)-urea HO T HA F H H F) p, N yN 1- (3, 5-Difluoro-4-hydroxy- 840 o, 4, ! o, phenyl)-3-(4-phenoxy-phenyl)-C19H14F2N203 A 356. 32 356. 6 HO'r 0 Hj. g urea H H H H F N N 841 1- (3, 5-Difluoro-4-hydroxy- C13HlOF2N202A264. 23 264. 7 Ho phenyl)-3-phenyl-urea F OH rvNo 3- {3- [3-Chloro-4-hydroxy-5- (1- 842 < o o hydroxy-ethyl)-phenyl]-ureido}-C14H19CIN205 A 330. 76 331. 1 HO T propionic acid ethyl ester cl OH N 1- [3-Chloro-4-hydroxy-5- (I- 843 W T hydroxy-ethyl)-phenyl]-3-pentyl-C14H2 lCIN203 A 300. 78 301. 2 HO urea cri o OH N N 1- [3-Chloro-4-hydroxy-5- (l- 844 HOX hydroxy-ethyl)-phenyl]-3-pentyl-C16H17ClN203 A 320. 77 321. 0 HO 0 urea o GI OH N N (1- [3-Chloro-4-hydroxy-5- (I- 845 Tl T Y hydroxy-ethyl)-phenyl]-3-(2-C17H19ClN203 A 334. 80 335. 1 HOX methyl-benzyl)-urea ci OH N N 1- [3-Chloro-4-hydroxy-5- (1- 846 hydroxy-ethyl)-phenyll-3-C17Hl9CIN203 A 334. 80 335. 3 HO T phenethyl-urea o OH N N 1- [3-Chloro-4-hydroxy-5- (l- 847 0 hydroxy-ethyl)-phenyl]-3- (1, 1, 3, 3- 17H27C12N202 A 342. 86 343. 7 Ho T tetramethyl-butyl)-urea cl OH N N 1-tert-Butyl-3- [3-chloro-4- 848 JJ. J K'hydroxy-5- (l-hydroxy-ethyl)- C13H19C1N203 A 286. 75 287. 6 HO T phenyl]-urea C) OH N N 1- [3-Chloro-4-hydroxy-5- (1- 859 || | T hydroxy-ethyl)-phenyl]-3-C16H23ClN203 A 326. 82 327. 5 HO X cyclohexylmethyl-urea cl ^'CF3 OH CES OH F ! N N 1- [3-Chloro-4-hydroxy-5- (1- 850 v Y hydroxy-ethyl)-phenyl]-3-(4-C17H16CIF3N203 A 388. 77 389. 4 HoX trifluoromethyl-benzyl)-urea C) OH N ci 1- [3-Chloro-4-hydroxy-5- (I- 851 0 hydroxy-ethyl)-phenyl]-3-(4-ClSH13C13N203 A 375. 63 376. 2 Ho zu chloro-phenyl)-urea Cl Cl OH NyNa 1- [3-Chloro-4-hydroxy-5- (l- 852 0 J E JL hydroxy-ethyl)-phenyl]-3- (4- C15H14C12N203 A 341. 19 341. 6 H T Cl chloro-phenyl)-urea Cl OH OH... ! OH - Ny N, 1- [3-Chloro4-hydroxy-5- (I- 853 x : ° W hydroxy-ethyl)-phenyl]-3-(4-C16H14ClF3N203 A 374. 74 375. 0 HO ~ CF3 trifluoromethyl-phenyl)-urea cl OH NYNO 1- [3-Chforo4-hydroxy-5- (I- 854 Q xJ ° k) hydroxy-ethyl)-phenyl]-3-C15H21CIN203 A 312. 79 313. 0 HO cyclohexyl-urea OH OH N N Ny N 1- [3-Chloro-4-hydroxy-5- (l- 855, Jt xJ õ hydroxy-ethyl)-phenyl]-3-(4-C16H14ClF3N204 A 390. 74 391. 2 HO T OCF3 trifluoromethoxy-phenyl)-urea Ci OH 1- [3-Chloro-4-hydroxy-5- (I- 856 ß d o Ws hydroxy-ethyl)-phenyl]-3-(S C16H14CIN303 A 331. 75 332. 0 HO T CN cyano-phenyl)-urea cl OH N N __o 1-Benzo [1, 3] dioxol-5-yl-3- [3- 857 chloro-4-hydroxy-5- (l-hydroxy- C16Hl5CIN205A350. 75 351. 1 HO ethyl)-phenyll-urea o OH NyN 1- [3-Chloro-4-hydroxy-5- (l- 858 HOX ° W hydroxy-ethyl)-phenyl]-3->tolyl-C16Hl7ClN203 A 320. 77 321. 0 w cl cl OH N N OMe 1- [3-Chloro-4-hydroxy-5- (l- 859 JL J o 1i. J hydroxy-ethyl)-phenyl]-3- (3- C16H17CIN204 A 336. 77 337. 1 < methoxy-phenyl)-urea OH OH 1- [3-Chloro-4-hydroxy-5- (l- 860 {hydroxy-ethyl)-phenyl]-3-(2, 6-C17H19CIN203 A 334. 80 335. 2 cl dimethyl-phenyl)-urea Ci OH N N OMe 1- [3-Chloro-4-hydroxy-5- (l- 861 11 1 0 n hydroxy-elyl)-phenyl]-3-(3, 4, 5- C18H21CIN206 A 396. 82 397. 2 HOX wOMe ttimethoxy-phenyl)-urea Cl OMe OU N N I 1- [3-Chloro-4-hydroxy-5- (1- 862 y hydroxy-ethyl)-phenyl]-3-C19Hl7CIN203 A 356. 80 357. 1 HO 0 naphthalen-1-yl-urea cl X Z OH H I-Adamainitan-1-yl-3- [3-chloro-4- H 863 N NH hydroxy-5- (l-hydroxy-ethyl)- C19H25CIN203 A 364. 87 365. 1 phenyl]-urea HO zozo HO"Y' Ci OH N N 1- [3-Chloro-4-hydroxy-5- (1- 864 t hydroxy-ethyl)-phenyl]-3-(4-C21H19CIN204 A 398. 84 399. 0 HOt ° O9 phenoxy-phenyl)-urea o OH Ny No 1- [3-Chloro-4-hydroxy-S- (l- 865 hydroxy-ethyl)-phenyll-3-phenyl-C15Hl5CIN203 A 306. 74 307. 0 Cl. Cri C ! 1- (3-Chloro-4-hydroxy-phenyl)-3- 866 J s pentyl-thiourea C12H17CIN20S I 272. 79 272. 9 HO o I-Berlzyl-3- (3-chloro-4-hydroxy- 867 I II y Y y C14H13C1N20S I 292. 78 293. 1 Ho dz Ho CI N N 1- (3-Chloro-4-h drox-hen 1)-3- 868 lys Y ci5H15CIN20S I 306. 81 306. 9 1 (2-methyl-benzyl)-thiourea HOIR C ! H H N N , 869 , Sf , 1- (3-Chloro-4-hydroxy-phenyl)-3- C15H15C1N20S I 306. 81 307. 1 Ho phenethyl-thiourea cl 1- (3-Chloro-4-hydroxy-phenyl)-3- 870 s (1, 1, 3, 3 tetramethyl-butyl)-Cl5=06 I 314. 81 315. 0 Ha thiourea o N N N 1-tert-Butyl-3- (3-chloro-4- C11H15C1N20S I 258. 77 258. 9 hydroxy-phenyl)-thiourea ci H H N N 1- (5-Chloro-2-hydroxy-phenyl)-3- ClOH13CIN20S I 244. 74 245. 0 Ho isopropyl-thiourea o N N 1_ (3-Chloro-4-hydroxy-phenyl)-3- 873 1- (3-Chloro-4-hydroxy-phenyl)-3- C14Hl9CIN20S 1 298. 83 299. 1 cyclohexylmethy1-thiourea HO'"T' Cl i CI CF3 N NJS 1-(3-Chloro4-hydroxy-phenyl)-3- « 1 874 « Y (4-tifluoromethyl-benzyl)-ClSH12CIF3N20S I 360. 78 361. 1 thiourea HA H H H H 875 t Y vcl 1-(3-Chloro-4-hydroxy-phenyl)-3-C13H9Cl3N20S I 347. 65 347. 9 H (3, 5-dichloro-phenyl)-thiourea a o ci ci H H 876 jCTTY. H3Chloro-4-bydroxy-phenyl)-3-ci3H10C12N20S I 313. 20 313. 5 HOXI (4-chloro-phenyl)-thiourea cl H H f, N, NA 1-(3-Chloro-4-hydroxy-phenyl)-3- w ( (4-trifluoromethyl-phenyl)-C14H10C1F3N20S I 346. 76 347. 0 -thiourea ci H H N'N 1- (3-Chloro-4-hydroxy-phenyl)-3- gg C13H17C1N20S Ii 284. 80 285. 0 Ho i S cyclohexyl-thiourea o CFS NH N o 1-(3-Chloro-4-hydroxy-phenyl)-3- 879 t Y 4 (2-trifluoromethyl-phenyl)-C14HIOCIF3N20S I 346. 76 347. 0 HO"q S thiourea CI H H N N 1- (3-Chloro-4-hydroxy-phenyl)-3- C13H11C1N20S I 278. 75 279. 0 Ho S phenyl-thiourea Ci H H CI N N 1- (3, 5-Dichloro-4-hydroxy- C12H16C12N20S I 307. 24 307. 5 HO< phenyl)-3-pentyl-thiourea cri H H Ny N 1-Benzyl-3- (3, 5-dichloro-4- C14Hl2Cl2N20S 1 327. 23 327. 4 hydroxy-phenyl)-thiourea HO Cl / CI N N 1- (3, 5-Dichloro-4-hydroxy- 883 II phenyl)-3- (2-methyl-benzyl)- C15H14CL2N20S I 341. 26 341. 4 HO thiourea o H H CI N N 1- (3, 5-Dichloro-4-hydroxy- C15H14C12N20S I 341. 26 341. 5 HO phenyl)-3-phenethyl-thiourea cl H H Ny N 1- (3, 5-Dichloro-4-hydroxy- 885 D s phenyl)-3-(1, 1, 3, 3-tetramethyl-C15H22C12N20S I 349. 32 349. 6 s P y) > > Y Ho butyl)-thiourea ci Cl NH HNsS 1-tert-Butyl-3- (3, 5-dichloro-4- C11H14C12N20S I 293. 21 293. 6 Ho hydroxy-phenyl)-thiourea cl H H Cl/< N N </z 887 Ny N_r 1- (5-Chloro-4-hydroxy-phenyl)-3- ClOH12Cl2N20S 1 279. 19 279. 5 gg, sr C10HI2CI2N20S I 279. 19 279. 5 Ho isopropyl-thiourea ci N N 1- (3, 5-Dichloro-4-hydroxy- 888 II phenyl)-3-cyclohexylmethyl-C14H18Ct2N20S I 333. 28 333. 5 HO thiourea Cl CF3 N N 1- (3, 5-Dichloro-4-hydroxy- 889 phenyl)-3- (4-trifluoromethyl- C15H11C12F3N20S I 395. 23 395. 5 H benzyl)-thiourea cl ci H H Ny N-qCl 1- (3, 5-Dichloro-4-hydroxy- 890 s phenyl)-3- (3, 5-dichloro-phenyl)- C13H8Cl4N20S 1 382. 09 382. 3 nrY Cl thiourea ci ci H H Cl N Y NH 1-(3, 5-Dichloro-4-hydroxy- 891 s phenyl)-3- (4-chloro-phenyl)- C13H9Cl3N20S 1 345. 65 345. 9 thiourea ci H H N yN 1- (3, 5-Dichloro-4-hydroxy- 892 0zW s s phenyl)-3- (4-trifluoromethyl- C14H9Cl2F3N20S 1 381. 2 381. 6 phenyl)-thiourea CI H H CI N N 893 X s 0 1-(3, 5-Dichloro-4-hydroxy-C13H16C12N20S I 319. 25 319. 6 HO phenyl)-3-cyclohexyl-thiourea Cl CF3. H H i clw Y 1-(3, 5-Dichloro4-hydroxy- 894 II phenyl)-3- (2-trifluoromethyl- C14H9C12F3N20S I 381. 20 381. 4 HO phenyl)-thiourea cl NU N CI N N 1- (3, 5-Dichloro-4-hydroxy- C13H1OCl2N20S I 313. 20 313. 5 HO phenyl)-3-phenyl-thiourea ci H H 896 2N N 1- (4-Hydroxy-3-nitro-phenyl)-3- 896 I C12H17N303S I 283. 35 283. 9 pentyl-thiourea HO H H ZN N \ 1-Benzyl-3- (4-hydroxy-3-nitro- HO-' ho Ho I s i O N N N 1- (4-Hydroxy-3-nitro-phenyl)-3-- (2-methyl-benzyl)-thiourea Ci5H15N303S I 317. 36 317. 9 Ho HO y 1- (4-Hydroxy-3-nitro-phenyl)-3- HO, I s (I i phenethyl-thiourea HO Structure Chemical name Formula Synthesis MolWeight MS data methods 02N H HXz 1-(4-Hydroxy-3-nitro-phenyl)-3- 900 HOv t l l (1, 1, 3, 3-tetramethyl-butyl)- C15H23N303S I 325. 43 326. 1 HO thiourea H H_ I/ 901 o2N I N ici N 1-tert-Butyl-3- (4-hydroxy-3-nitro-CllHl5N303S 1 269. 32 239. 9 How s P Y) H H 902 02N >>NN 1 (4 Hydroxy-3-nitro-phenyl)-3-ClOH13N303S I 255. 29 255. 9 lez s isopropyl-thiourea HO OzN N N 1-Cyclohexylmethyl-3- (4- 903 02N) S hydroxy-3-nitro-phenyl)-thiourea HO CF3 HO' H H 1- (4-Hydroxy-3-nitro-phenyl)-3- 904 (4-trifluoromethyl-benzyl)-C15Hl2F3N303S 1 371. 33 372. 0 s -thiourea HA H H H H 02N : % N CI 905 1- (3, 5-Dichloro-phenyl)-3- (4- C13H9C12N303S I 358. 20 358. 6 cl o H H 02N N N 1- (4-Chloro-phenyl)-3- (4-hydroxy- y 3-nitro-phenyl)-thiourea HO CI 02N N HN 1-(4-Hydroxy-3-nitro-phenyl)-3- 907 < Y Yq (4-tåfluoromethyl-phenyl)-C14HlOF3N303S I 357. 31 357. 9 HO/ thiourea H H 908 o2N I N'N\ ^ 1-Cyclohexyl-3- (4-hydroxy-3- C13H17N303S I 295. 36 296. 0 /S nitro-phenyl)-thiourea Ho ON H CF3 1- (4-Hydroxy-3-nitro-phenyl)-3- 909 02N, N NfA (2-tlifluoromethyl-phenyl)-C14HlOF3N303S I 357. 31 357. 6 HO'a thiourea H H 910 NN N 1- (4-Hydroxy-3-nitro-phenyl)-3- C13HIIN303S1289. 31 289. 5 s phenyl-ffiiourea HA 911 F I NN 1- (3-Fluoro-4-hydroxy-phenyl)-3- C12H17FN20S I 256. 34 256. 8 , S pentyl-thiourea Howl N-Benzyl-3- (3-fluoro-4-hydroxy- 912 C14H13FN20S I 276. 33 276. 7 phenyl)-thiourea HO) as N Nn F N N 1- (3-Fluoro-4.-hydroxy-phenyl)-3- HO42 S (2-methyl-benzyl)-thiourea HO Ho 914 F N N 1- (3-Fluoro-4-hydroxy-phenyl)-3- Ho I I/phenethyl-thiourea C15H15FN20S I 290. 36 290. 5 H H H F Ny N 1- (3-Fluoro-4-hydroxy-phenyl)-3- 915 v s < (1, 1, 3, 3-tetramethyl-butyl)- C15H23FN20S I 298. 42 298. 7 Ho thiourea H H F rNyN- 1-tert-Butyl-3- (3-fluoro-4- 916 ( C11H15FN20S I 242. 31 242. 8 Ho H H H H 917 F>PC N N 1 (3 Fluoro-4-hydroxy-phenyl)-3-ClOH13FN20S I 228. 29 228. 5 s isopropyl-thiourea HO 918 F Ny N 1- (3-Fluoro-4-hydrox3t"phenyl)-3- C14Hl9FN20S 1 282. 38 282. 7 Ho) I cyclohexylmethyl-thiourea HOw S | HO . CFs H H 1- (3-Fluoro-4-hydroxy-phenyl)-3- 919 y (4-trifluoromethyl-benzyl)-C15Hl2F4N20S 1 344. 33 344. 7 thiourea s HO H H 920 F I/NN I/ 1- (3-Fluoro-4-hydroxy-phenyl)-3- C13H9C12FN20S I 331. 19 331. 5 HO Cl. (3, 5-dichloro-phenyl)-thlourea cl H H 921 F \ \ 1- (3-Fluoro-4-hydroxy-phenyl)-3- C13H10C1FN20S I 296. 75 297. 1 (4-chloro-phenyl)-thiourea Ho cl F N N 1- (3-Fluoro-4-hydroxy-phenyl)-3- 922 YjYYi (4-triauoromethyl-phenyl)-C14H10F4N20S I 330. 30 330. 6 H H H H 923 F \ N'N ^ 1- (3-Fluoro-4-hydroxy-phenyl)-3- 13H17FN20S I 268. 35 268. 6 cyclohexyl-thiourea Ha CFs H H 1- (3-Fluoro-4-hydroxy-phenyl)-3- 924 < Y T ol (2-tifluoromethyl-phenyl)-C14HlOF4N20S I 330. 30 330. 5 Ha s thiourea H F N N 925 F \ N'N ^ 1- (3-Fluoro-4-hydroxy-phenyl)-3- C13Hi1FN20S I 262. 30 262. 5 HO s phenyl-thiourea OH OH N N 1- (2, 4-Dihydroxy-phenyl)-3- 926 I pentyl-thiourea C12H18N202S I 254. 35 254. 6 HO S OH 927 N N 1-Benzyl-3- (2, 4-dihydroxy- C14H14N202S I 274. 34 274. 7 phenyl)-thiourea HO I S HO- OH 928 g4zH H> 1-(2, 4-Dihydroxy-phenyl)-3-(2-C15H16N202S I 288. 36 288. 6, a methyl-benzyl)-thiourea /s HA OH N N 1- (2, 4-Dihydroxy-phenyl)-3- 929 phenethyl-thiourea C15Hl6N202S1 288. 36 288. 6 OH OH 1- (2, 4-Dihydroxy-phenyl)-3- 930 N N (1, 1, 3, 3-tetramethyl-butyl)-C15H24N202S I 296. 43 296. 7 s thiourea HA OH 931 N N 1-tert-Butyl-3- (2, 4-dihydroxy- CllHl6N202S1240. 32 240. 6 OH Ho OH 932 N N, r 1- (2, 4-Dihydroxy-phenyl)-3- ClOH14N202S1226. 30 226. 7 isopropyl-thiourea H OH HYH I-Cyclohexylmethyl-3- (2, 4- dihydroxy-phenyl)-thiourea - s oh OH H CF3 1- (2, 4-Dihydroxy-phenyl)-3- (4- trifluoromethyl-benzyl)-thiourea s HA OH H H Nu N C 1- (3, 5-Dichloro-phenyl)-3- (2, 4- s dihydroxy-phenyl)-thiourea ! Ho Cl OH N N 1- (4-Chloro-phenyl)-3- (2, 4- 936 I I dihydroxy-phenyl)-thiourea C13H11CIN202S I 294. 76 295. 0 OH OH 1- (2, 4-Dihydroxy-phenyl)-3- (4- 937 C14H11F3N202S I 328. 31 328. 7 , S , trrifluoromethyl-phenyl)-thiourea H CL OH 938 N 1-Cyclohexyl-3- (2, 4-dihydroxy- 0., &HYH s phenyl)-thiourea HA OH CF3 1- (2, 4-Dihydroxy-phenyl)-3- (2- 939 C14Hi1F3N202S I 328. 31 328. 6 trifluoromethyl-phenyl)-thiourea Ho OH 940 N N 1- (2, 4-Dihydroxy-phenyl)-3- C13H12N202S I 260. 31 260. 6 Ho ' H H H 941 1- (3, 5-Dibromo-4-hydroxy- C12Hl6Br2N20S1396. 14 396. 5 /S C12H16Br2N20S I 396. 14 396. 5 <, phenyl)-3-pentyl-thiourea er /I H H ar N N 1-Benzyl-3- (3, 5-dibromo-4- 942'/ s hydroxy-phenyl)-thiourea HO I Br / er N N 1- (3, 5-Dibromo-4-hydroxy- 943 ! f j"phenyl)-3- (2-methyl-benzyl)- C15H14Br2N20S I 430. 16 430. 5 thiourea Br H H Br N N 944 1- (3, 5-Dibromo-4-hydroxy- ClSH14Br2N20S1430. 16 430. 5 HO phenyl)-3-phenethyl-thiourea Bof H H sr N N 1- (3, 5-Dibromo-4-hydroxy- 945a Ho s phenyl)-3- (1, 1, 3, 3-tetramethyl- C15H22Br2N20S I 438. 22 438. 6 Ho s P butyl)-thiourea Br H H ! 946 tT ! l-tert-Butyl-3- (3, 5-dibromo-4- cilH14Br2N20S I 382. 11 382. 4 Ho hydroxy-phenyl)-thiourea Br H H er i N N 1_ (3, 5-Dibromo-4-hydroxy- 947 Ho i ls phenyl)-3-isopropyl-thiourea ci0H12B2. N20S I 368. 09 368. 4 HO< S phOnyl)-3-iSOprOpyl-thiOUIea v v Br H H ri Br N NO 1-(3, 5-Dibromo-4-hydroxy- 948 II phenyl)-3-cyclohexylmethyl-C14H18Br2N20S I 422. 18 422. 5 thiourea Br Br CF3 N N 1- (3, 5-Dibromo-4-hydroxy- 949) j ! Y phenyl)-3- (4-trifluoromethyl- C15HllBr2F3N20S I 484. 13 484. 5 benzyl)-thiourea Br H H Ny N_qCl 1- (3, 5-Dibromo-4-hydroxy- 950 , S , phenyl)-3- (3, 5-dichloro-phenyl)- C13H8Br2C12N20S I 470. 99 471. 4 HO thiourea Br Ci H H Br y N 1- (3, 5-Dibromo-4-hydroxy- 951 J' s phenyl)-3- (4-cbloro-phenyD- C13H9Br2CIN20S I 436. 55 437. 0 Ho thiourea Br H H B N N 1-(3, 5-Dibromo-4-hydroxy- 952 phenyl)-3- (4-trifluoromethyl- C14H9Br2F3N20S 1 470. 10 470. 6 HO CF3 phenyl)-thiourea Br H H Br N N 953 , 1- (3, 5-Dibromo-4-hydroxy- C13H16B2N20S I 408. 15 408. 5 Ho phenyl)-3-cyclohexyl-iourea Br CF3 H H f N N >/4. 1-(3, 5-Dibromo-4-hydroxy- 954 J'J J phenyl)-3- (2-tnfluoromethyl- C14H9Br2F3N20S I 470. 10 470. 5 Ho phenyl)-thiourea Br H H 955 Br I, N'S'N , 1- (3, 5-Dibromo-4-hydroxy- C13H10Br2N20S I 402. 10 402. 6 Ho phenyl)-3-phenyl-thiourea Br H H j 956 s 1- (3, 5-Difluoro-4-hydroxy- C12Hl6F2N20S 1 274. 33 274. 8 Ho, phenyl)-3-pentyl-thiourea F / H H 957 I-Benzyl-3- (3, 5-difluoro-4- C14Hl2F2N20S 1 294. 32 294. 7 s hydroxy-phenyl)-thiourea HA F H H, _o 1- (3, 5-Difluoro-4-hydroxy- 958 phenyl)-3- (2-methyl-benzyl)- C15H14F2N20S I 308. 35 308. 6 S thiourea F H H f H H F N'N \ 1_ (3, 5-Difluoro-4-hydroxy- 959 , S (, C15Hl4F2N20S I 308. 35 308. 6 Ho phenyl)-3-phenethyl-thiourea F F : q Ny N 1- (3, 5-Difluoro-4-hydroxy- 960 s phenyl)-3- (1, 1, 3, 3-tetramethyl- C15H22F2N20S I 316. 41 316. 8 Ho butyl)-thiourea F H H j 961 y 1-tert-Butyl-3- (3, 5-Difluoro-4- CllHl4F2N20S 1 260. 30 260. 5 No S hydroxy-phenyl)-thiourea F H H 962 y 1- (3, 5-Difluoro-4-hydroxy- ClOH12F2N20S 1 246. 28 246. 5 II C10H12F'2N20S I 246. 28 246. 5 962 Ho/s phenyl)-3-isopropyl-thiourea F HH 1- (3, 5-Difluoro-4-hydroxy- 963 II phenyl)-3-cyclohexylinethyl-C14H18F2N20S I 300. 37 300. 6 thiourea F CF3 F N N 1- (3, 5-Difluoro-4-hydroxy- 964- phenyl)-3- (4-trifluoromethyl- C15H11F5N20S I 362. 32 362. 8 Houx S benzyl)-thiourea F H H F, 1- (3, 5-Difluoro-4-hydroxy- 965 s phenyl)-3- (3, 5-dichloro-phenyl)- C13H8Cl2F2N20S 1 349. 18 349. 7 Ho thiourea F CI H H 966 FqNyN 1- (3, 5-Difluoro-4-hydroxy- 966, 4J s CI phenyl)-3-(4-chloro-phenyl)-C13H9CIF2N20S I 314. 74 315. 2 HO A thiourea F H H Fa N H 1-(3, 5-Difluoro-4-hydroxy- 1'f 1 967 s phenyl)-3- (4-trifluoromethyl- C14H9F5N20S 1 348. 29 348. 8 phenyl)-thiourea F F H H F N'N 1_ (3, 5-Difluoro-4-hydroxy- 968 S C13H16F2N2oS I 28634 286. 6 Ho phenyl)-3-cyclohexyl-thiourea F CF3 H H) F, zN N J 1-(3, 5-Difluoro-4-hydroxy- 969 | phenyl)-3-(2-trifluoromethyl-C14H9F5N20S I 348. 29 348. 8 HOX S v phenyl)-thiourea F H H y 1- (3, 5-Difluoro-4-hydroxy- C13H10F2N20S I 280. 29 280. 5 Ho phenyl)-3-phenyl-thiourea F OH N 1- [3-Chloro-4-hydroxy-5- (I- 971 10, J T hydroxy-ethyl)-phenyl]-3-pentyl-C14H21ClN202S I 316. 85 316. 9 Ho Y thiourea ci OH on r !) N N 1-Benzyl-3- [3-chloro-4-hydroxy- 972 \ II 5- (1-hydroxy-ethyl)-phenyl]- C16H17C1N202S I 336. 84 337. 2 HOX S thiouxea cl OH N N \ 1- [3-Chloro-4-hydroxy-5- (1- 973 ll Al Y hydroxy-ethyl)-phenyl]-3-(2-C17H19CIN202S I 350. 86 351. 1 HO s methyl-benzyl)-thiourea cl OH N N 1- [3-Chloro-4-hydroxy-5- (l- A J S 1L J hydroxy-ethyl)-phenyl]-3-C17H19CIN202S I 350. 86 351. 0 HO phenethyl-thiourea ci OH Nu N 1- [3-Chloro-4-hydroxy-5- (1- 975 Jl x ; s hydroxy-ethyl)-phenyl]-3-(1, 1, 3, 3-C17H27CIN202S I 358. 93 359. 2 HO tetramethyl-butyl)-thiourea OH OH N 1-tert-Butyl-3- [3-chloro-4- 976 Jl xJ s hydroxy-5-(1-hydroxy-ethyl)-C13H19ClN202S I 302. 82 303. 0 HO phenyl]-thiourea C ! OH H H 1- [3-Chloro-4-hydroxy-5- (1- 977 jL J !'hydroxy-ethyl)-phenyl]-3-C12H17CIN202S I 288. 79 289. 0 HO T isopropyl-thiourea cl Cl. OH < _ 978 Ny N 1- [3-Chloro-4-hydroxy-5- (l- 978 lit T hydroxy-ethyl)-phenyl]-3-C16H23CIN202S L 342. 88 343. 1 cyclohexylmethyl-thiourea cri cl OH L N N 1- [3-Chloro-4-hydroxy-5- (l- 979))))) hydroxy-ethyl)-phenyl]-3- (4- C17H16CIF3N202S I 404. 83 405. 2 HO < trifluoromethyl-benzyl)-thiourea a OH H H N Cl 1- [3-Chloro-4-hydroxy-5- (1- 980 | hydroxy-ethyl)-phenyl]-3-(3, 5-ClSH13Cl3N202S I 391. 70 392. 0 HO s dichloro-phenyl)-thiouirea ci ci OH H H N N 1- [3-Chloro-4-hydroxy-5- (1- 981 JL J § TL JL hydroxy-ethyl)-phenyl]-3- (4- C15H14CI2N202S t 357. 25 357. 6 Ho ci chloro-phenyl)-thiourea ci OH H H Ny N 1- [3-Chloro-4-hydroxy-5- (l- 982 t hydroxy-ethyl)-phenyl]-3-(4-C16H14CIF3N202S I 390. 81 391. 0 HOX 9CF3 wifluoromethyl-phenyl)-thiourea cl OH H H NyNo 1- [3-Chloro-4-hydroxy-5- (l- 983 jL J S L J hydroxy-ethyl)-phenyl]-3-C1SH21CIN202S I 328. 86 329. 4 HO4g < cyclohexyl-thiourea Ci OH CF3 H H N N 1- [3-Chloro-4-hydroxy-5- (1- 984 z /hydroxy-ethyl)-phenyl]-3- (2- C16H14CIF3N202S I 390. 81 391. 0 HO trifluoromethyl-phenyl)-thiourea cl OH N N 1- [3-Chloro-4-hydroxy-5- (1- 985 , (, hydroxy-ethyl)-phenyl]-3-phenyl-C15H15C1N202S I 322. 81 323. 1 Ho thiourea cl N 2-Chloro-4- (2-phenylsulfanyl- 986 C19H16C1NOS D 341. 85 342_2 Ho s benzylamino)-phenol asz 2-Chloro-4- (2-p-tolylsulfanyl- H _qN benzylamino)-phenol ci i 2-Chloro-4- [2- (4-chloro- 9 8 , S phenylsulfanyl)-benzylamino]-C19H15C12NOS D 376. 30 376. 8 H cri phenol ci cl i N 2-Chloro-4- [2- (4-nitro- 989 A s phenylsulfanyD-benzylamino]-C19H15CIN203S D 386. 85 387. 2 Cul phenol NO, N02 / 2-Chloro-4- [2- (4-methoxy- 990 (phenylsulfanyl)-benzylamino]-C20H18CIN02S D 371. 88 372. 4 phenol cl OMe 2-Chloro-4- [2- (2-chloro- 991 HoX s phenylsulfanyl)-benzylamino]-C19HlSC12NOS D 376. 30 376. 8 phenol cl H 2-Chloro-4- [2- (3-chloro- 992 J J ! phenylsulfanyl)-benzylamino]-C19H15C12NOS D 376. 30 376. 8 H 1nl phénol cl i N 2-Chloro-4- [2- (3, 4-dichloro- 993 phenylsulfanyl)-benzylaminol-C19Hl4Cl3NOS D 410. 74 411. 2 Ho I phenol ci cri N- (4- f 2- [ (3-Chloro-4-hydroxy- phenylamino)-methyl]- 994 phenylaniino)-methyl]-C2lHl9CIN202S D 398. 91 399. 3 H phenylsulfanyl I-phenyl)- Y acetamide Ci NHAE , fez w N wl 995 2-Chloro-4- [2- (quinolin-7- C22Hl7CLN20S D 392. 90 393. 4 Ho"qN 8 N yisulfanyl)-benzylamino]-phenol ci NOS H 2-Chloro-4- [2- (4-chloro- 996 N Y phenylsulfanyl)-5-nitro-Cl9Hl4C12N203S D 421. 30 421. 7 Ho ?,, N s benzylamino]-phenol ci NOs Nos / 997 N '2-Chloro-4- (5-nitro-2-p- tolylsulfanyl-benzylamino)-phenol HA jazz NH2 4- [5-Amino-2- (4-chloro- 998 I phenylsulfanyl)-benzylamino]-2-C19H16C12N20S D 391. 31 391. 9 H ci s cworo-phenol cl ci / 2-Chloro-4- [2- (4-chloro- 999 Ho , o2s \ benzenesulfonyl)-benzylamino]-C19H15C12N03S D 408. 30 408. 7 phenol ci ci 1000--in 2, 6-Dichloro-4- (2-phenylsulfanyl- HOX S) benzylamíno)-phenol ci i ci N 2, 6-Dichloro-4- (2-p-tolylsulfanyl- 1001 C20H17C12NOS D 390. 33 390. 7 Hoq benzylamino)-phenol HO Y i ! ci i Cl NJp 2, 6-Dichloro-4- [2- (4-chloro- 1002 phenylsulfanyl)-benzylamino]-C19Hl4Cl3NOS D 410. 75 411. 1 HO ci cl phenol ci, cri i H 2, 6-Dichloro-4- [2- (4-nitro- 1003 , S phenylsulfanyl)-benzylamino]-C19H14CI2N203S D 421. 30 421. 8 phenol cri N02 NOZ H N 2, 6-Dichloro-4- [2- (4-methoxy- 1004 phenylsulfanyl)-benzylamino]-C20H17C12N02S D 406. 33 406. 7 phénol cl OMe H 41 N 2, 6-Dichloro-4- [2- (2-chloro- 1005 , S phenylsulfanyl)-benzylamino]-C19H14CI3NOS D 410. 75 411. 2 Ho I phenol cl, ci H N 2, 6-Dichloro-4- [2- (3-chloro- 1006 !) j phenylsulfanyl)-benzylamino]-C19H14CI3NOS D 410. 75 411. 2 HO cl phenol ira jazz H Cl N/9 2, 6-Dichloro-4- [2- (3, 4-dichloro- 1007 Ho S ci phenylsulfanyl)-benzylamino]-C19H13C14NOS D 445. 19 445. 6 Phenol if c i Cl No 9 N-(4-{2-[(3, 5-Dichloro-4-hydroxy- N 1008 HOv S phenylamino)-methyl] ; C21H18C12N202S D 433. 36 433. 8 acetamide lio ci acetamide ci N 2, 6-Dichloro-4- [2- (quinolin-7- 1009 C22H16C12N20S D 427. 35 427. 8 1009 s N ylsulfanyl)-benzylamino]-phenol cl... cl N02 H | 11 2, 6-Dichloro-4- [2- (4-chloro- 1010 N phenylsulfanyl)-5-nitro-C19Hl3Cl3N203S D 455. 74 456. 0 Ho ci benzylamino]-phenol ci ci NO2 / H 1011 N 2, 6-Dichloro-4- (5-nitro-2-p- C20Hl6Cl2N203S D 435. 33 435. 7 Ci s tolylsulfanyl-benzylamino)-phenol HO cl NH2 / 4- [5-Amino-2- (4-chloro- 1012 N phenylsulfanyl)-benzylaniinol-2, 6- C19Hl5Cl3N20S D 425. 76 426. 0 Ho ci s dichloro-phenol cl ci H C,) ( N 2, 6-Dichloro-4- [2- (4-chloro- 1013 Ho , o2s \ benzenesulfonyl)-benzylanino]-C19H14C13N03S D 442. 75 443. 1 phenol ci Sci H f) T 1014 2-Nitro-4- (2-phenylsulfanyl- 352. 41 352. 8 Ho I s benzylamino)-phenol HO" 1015 2-Nitro-4- (2-p-tolylsulfanyl- 366. 43 366. 8 Ho I s benzylamino)-phenol C2oH18N203s D i Ha 1016 Yj T 4- [2- (4-Chlorophenylsulfanyl)- ci9H15C ! N203S D 386. 85 387. 2 Ho'v S w benzylarnino]-2-nitro-phenol i ci i I,, I % Ns NX | 2-Nitro4-[2-(4-nitro- 1017 1" ;" s phenylsulfanyl)-benzylamino]-C19Hl5N305S D 397. 40 397. 7 -phenol Nô H OZN N \ 1018 4- [2- (4-Methoxy-phenylsulfanyl)- C20H18N204S D HO S\ [3\OMe benzylarruno]-2-mtro-phenol Oye ZONE 0, N N - 1019 4- [2- (2-Chloro-phenylsulfanyl)- C19H15C1N203S D 386 85 387. 2 HO benzylamino]-2-nitro-phenol cl 02N N 02N N 4- [2- (3-Chloro-phenylsulfanyl)- Ho I s ci benzylamino]-2-nitro-phenol HO . H 1021 0'N N 4- [2- (3, 4-Dichloro- 1021 JXJ s cs phenylsulfanyl)-benzylamino]-2-C19H14C12N203S D 421. 30 421. 7 nitro-phenol cl . 02N N N- (4- {2- [ (4-Hydroxy-3-nitro- phenylamino)-methyl]- 1022 Ho i s \ phenylsulfanyl}-phenyl)-C21H19N304S D 409_46 409. 9 .,,, \. phenylsulfanyl}-phenyl)- nu jj acetamide NHAc / OzN N \ 1023 2-Nitro-4- [2- (quinolin-7- " ylsulfanyl)-benzylammo]-phenol HO NOS / 1024 02N N 4- [2- (4-Chloro-phenylsulfanyl)-5- C19Hl4CIN305S D 431. 85 432. 2 NO2 Ho I cl N02 H ruz 1025 o, m N 2-Nitro-4- (5-nitro-2-p- C20Hl7N305S D 411. 43 411. 9 ' tolylsulfanyl-benzylamino)-phenol NHZ / NHAc O N-f 4- (4-Chloro-phenylsulfanyl)-3- 1026 02Nll N [ (4-hydroxy-3-nitro-phenylamino)- C2lHl8CIN304S D 443. 90 444. 3 Ho I s methylj-phenyl}-acetamide i ci H J ! n 1027 II/4- [2- (4-Chloro-benzenesulfonyl)- C19H15C1N205S D 418. 85 419. 2 HO 1n1 | cul Xi F N \ 1028 2-Fluoro-4- (2-phenylsulfanyl- Ho ' s benzylammo)-phenol Ha 1029 2-Fluoro-4- (2-p-tolylsulfanyl- Ho I s benzylamino)-phenol C20H18FNOS D 339. 43 340. 8 Ha F N 2-Fluoro-4- [2- (4-chloro- 1030 Jl J'phenylsulfanyl)-benzylamino]-C19H15CIFNOS D 359. 84 360. 1 Ho phenol phenol V ci H F N 2-Fluoro-4- [2- (4-nitro- I03I uNO2 phenylsulfanyl)-benzylamino]-| CI9H15F1 2035 D 370. 40 370. 8 Phenol N02 N02 / H F NHJ 3 2-Fluoro-4-[2-(4-methoxy-_ 1032 phenylsulfanyl)-benzylamino]-C20H18FN02S D 355. 43 355. 8 Ho phénol phenol i OMe H H F N 2-Fluoro-4- [2- (2-chloro- 1033 J} J'phenylsulfanyl)-benzylamino]-C19H15CIFNOS D 359. 84 360. 2 phénol. cl N 2-Fluoro-4- [2- (3-chloro- 1034 phenylsulfanyl)-benzylamino]-C19Ht5CIFNOS D 359. 84 360. 3 Ho I phenol . H I F N---p 2-Fluoro-4- [2- (3, 4-dichloro- 1035 HOJW SCCCI phenylsulfanyl)-benzylamino]-C19H14C12FN0S D 394. 29 394. 6 Phenol cl N- (4- {2- [ (3-Fluoro-4-hydroxy- 1036 phenylamino)-methyl]-C21H19FN202S D 382. 45 382. 9 Ho I S phenylsulfanyl}-phenyl)- acetamide v-NHAc F N \ 1037 2-Fluoro-4- [2- (quinolin-7- Ho I s N ylsulfanyl)-benzylamino]-phenol C22H17FN20S D 376. 45 377. 0 Ho / H 2-Fluoro-4- [2- (4-chloro- 1038 phenylsulfanyl)-5-nitro-C19H14C1FN203S D 404. 84 405. 3 Hoa s benzylamino]-phenol i ci NO2 / 1039 F N 2-Fluoro-4- (5-nitro-2-p- H S¢ tolylsulfanyl-benzylamino)-phenol Ha NOS NHZ 4- [5-Arnino-2- (4-chloro- 1040 F I N phenylsulfanyl)-benzylamino]-2-C19H16CIFN20S D 374. 86 375. 1 ",) a s fluoro-phenol Cri ci f / H I N 2-Fluoro-4- [2- (4-cWoro- 1041 I) J., ! benzenesulfony !)-benzylamino]- C19H15CIFN03S D 391. 84 392. 0 Phenol ci OH H N 1042 4- (2-Phenylsulfanyl-benzylamino)- C19H17N02S D 323. 41 323. 8 Ho I s benzene-l, 3-diol HO OH N benzylamino)-benzene-1, 3-diol C20H19N02S D 337_44 337. 8 Oh OH/ H 1044 4- [2- (4-Chloro-phenylsulfanyl) Ho I i S benzylamino]-benzene-1, 3-diol ci OH ON i' N 1045 , S 4- [2- (4-Nitro-phenylsulfanyl)- C19H16N204S D 368. 41 36$. 7 Ho \ benzylamino]-benzene-1, 3-diol Nô No2 OH N 4- [2- (4-Methoxy-phenylsulfanyl)- C20H19N03S D 1046 HO , S \ benzylamino]-benzene-1, 3-diol 353. 43 353. 7 xi "OMe OH H N 1047 4- [2- (2-Chloro-phenylsulfanyl)- C19H16CIN02S D Ho s benzylamino]-benzene-1, 3-diol oh cW OH/ N OH. __. _ 1048 Cl9H16CIN02S D 357. 86 358. 1 s c benzylamino]-benzene-1, 3-diol OU H 4- [2- (3, 4-Dichloro- 1049 s cl phenylsulfaiayl)-benzylaminol-C19Hl5Cl2NO2S D 392. 30 392. 7 OH l oh OU N- (4- {2- [ (2, 4-Dihydroxy- 1050 phenylamino)-methyl]- phenylsulfanyl}-phenyl)-C21H20N203S D 380. 45 38b. 8 acetamide NHZ OH H 1051 \ C22H18N202S D 374. 46 374. 9 HO S N\ benzylamino]-benzene-1, 3-diol Nô, L oh 4- [2- (4-Chloro-phenylsulfanyl)-5- 1052 N nitro-benzylamino]-benzene-1, 3- C19Hl5ClN204S D 402. 85 403. 2 diol i NOs N02 OH OH A 1053 C20H18N204S D 382. 43 382. 7 benzylamino)-benzene-1, 3-diol HA NHZ OH 4- [5-Amino-2- (4-chloro- 1054 yN so t phenylsulfanyl)-benzylamino]-C19H17ClN202S D 372. 87 373. 0 H s benzene-1, 3-diol cri a OH 4- [2- (4-Chloro-benzenesulfonyl)- 1055 o- o&s benzylaouno]-benzene-l, 3-diol H _cl Br N 2, 6-Dibromo-4- (2-phenylsulfanyl- 1056 C19H15Br2NOS D 465. 20 465. 7 benzylamino)-phenol Ha Ber Br N 1057 I 2, 6-Dibromo-4- (2-p-tolylsulfanyl- C20H17Br2NOS D 479. 23 479. 3 Ho s benzylamino)-phenol Ber H 2 No 2, 6-Dibromo-4- [2- (4-chloro- 1058 phenylsulfanyl)-benzylaxnino]-C19H14Br2CiNOS D 499. 65 500. 1 HO Br phenol cl / H 2, 6-Dibromo-4- [2- (4-nitro- 1059 JL. J s phenylsulfanyl)-benzylamino]-C19H14Br2N203S D 510. 2 510. 1 HO uns phenol Nô, NOz / N 2, 6-Dibromo-4- [2- (4-methoxy- 1360 iJ I phenylsulfanyl)-benzylamino]-C20H17Br2N02S D 495. 23 495. 3 Ho I phenol mo phenol OMe / N 2, 6-Dibromo4- [2- (2-chloro- 1061 phenylsulfanyl)-benzylamino]-C19Hl4Br2CINOS D 499. 65 499. 8 Ho I phenol Br cl, H Br NJ ; 3 2, 6-Dibromo-4- [2- (3-chloro- 1062 phenylsulfanyl)-benzylamino]-C19H14Br2CINOS D 499. 65 499. 8 Ho phenol Br / er N 2, 6-Dibromo-4- [2- (3, 4-dichloro- 1063 s ci phenylsulfanyl)-benzylamino]-C19Hl3Br2Cl2NOS D 534. 09 534. 2 Ho Br phenol cl N- (4- {2- [ (3, 5-Dibromo-4- hydroxy-phenylamino)-methyl]- 1064 C21H18BfZN202S D 522. 25 522. 4 Ho, q phenylsuffanyll-phenyl)-c acetamid NHZ - NHAc H Br N 2, 6-Dibromo-4- [2- (quinolin-7- '% \ ylsmranyl)-benzylanmio]-phenol HO Br N02 ion Br N 'C19H13Br2C1N203 ,,, "'- L i ir i\c-. C19H13Br2C, lN203 . o 1066 phenylsulfanyl)-5-nitro-S D 544.. 64 544. 8 s benzylaniinol-phenol s Ho ber NOS Nô, 1067) HiJQ t 2, 6-Dibromo-4- (5-nitro-2-p- C20H16Br2N203S D 524. 23 524. 6 tolylsulfanyl-benzylamino)-phenol /s Ho NHZ Br nu2 H 4- [5-Amino-2- (4-chloro- 1068 BreN phenylsulfanyl)-benzylamino]-2, 6-C19H15Br2CIN20S D 514. 66 514. 9 s dibromo-phenol Br I CI / 2, 6-Dibromo-4- [2- (4-chloro- 1069 l ! J ! benzenesulfonyl)-benzylamino]-C19H14Br2CIN03S D 531. 65 531. 7 8 uct phenol Br CI Cri F N 2, 6-Difluoro-4- (2-phenylsulfanyl- C19H15F2NOS D 343. 39 343. 6 S"o benzylarnino)-phenol Ha F / F N I 2, 6-Difluoro-4.- (2-p-tolylsulfanyl- 1071 C20H17F2NOS D 357. 42 357. 8 F \ benzylamino)-phenol H F 1072 4- [2- (4-Chloro-phenylsulfanyl)- C19H14CIF2NOS D 377. 83 378. 1 Ho benzylaniino]-2, 6-Muoro-phenol cl CRI F N \ I 2, 6-Difluoro-4- [2- (4-nitro- 1073 , S phenylsulfanyl)-benzylamino]-C19H14F2N203S D 388. 39 388. 8 phénol F/ N02 / 2, 6-Difluoro-4- [2- (4-methoxy- 1074 phenylsulfanyl)-benzylarninol-C20Hl7F2NO2S D 373. 42 373. 7 phenol oye ORME FN 1075 4- [2- (2-Chloro-phenylsulfanyl)- C19H14C1F2NOS D 377. 83 378. 1 Ho s bfnzylamino]-2, 6-difluora-phenol F CI I 1076 F N 4- [2- (3-Chloro-phenylsulfanyl)- C19Hl4CIF2NOS D 377. 83 378. 2 1076 C19H14CIF2NOS D 377. 83 378. 2 HO) ( S ci benzylamino]-2, 6-difluoro-phenol F / N 4- [2- (3, 4-Dichloro- 1077 Fq C, phenylsulfanyl)-benzylamino]-2, 6- C19Hl3Cl2F2NOS D 412. 28 412. 6 difluoro-phenol cri CI N- (4- {2- [ (3, 5-Difluoro-4-hydroxy- phenylamino)-methyl]- HOX S\ffiG} phenylsulfanyl}-phenyl)- acetamide NHZ H 2 6-Difluoro-4- [2- (quinolin-7- Ho S N ylsulfanyl)-benzylaminol-phcnol HO i N02 / S) r H 4- [2- (4-Chloro-phenylsulfanyl)-5- 1080 I T nitro-benzylamino]-2, 6-difluoro-C19H13CIF2N203S D 422. 83 423. 3 Ho s phenol cri cl NO2 1081 F : qN 2, 6-Difluoro-4- (5-nitro-2-p- C20Hl6F2N203S D 402. 41 402. 8 F 4\ tolylsulfanyl-benzylamino)-phenol HA F/ NH2 H 4- [5-Amino-2- (4-chloro- 1082 F : qN phenylsulfanyl)-benzylamino]-2, 6- C19Hl5CIF2N20S D 392. 85 393. 0 Ho difluoro-phenol F wCI cl I 4- [2- (4-Chloro-benzenesulfonyl)- C19FI14C1F2N03S D 391. 84 392. 3 . OH < | HO'I Cl OH N 2-Chloro-6- (l-hydroxy-ethyl)-4- 1084 (2-phenylsulfaiayl-benzylamino)-C2lH20CIN02S D 341. 85 342. 3 Ho phenol ci OH N 2-Chloro-6- (l-hydroxy-ethyl)-4- 1085 (2-p-tolylsulfanyl-benzylamino)-C22H22CIN02S D 399. 93 400. 2 Ho phenol ci OH H N 2-Chloro-4- [2- (4-chloro- 1086 | phenylsulfanyl)-benzylarnino]-6-C21H19CI2NO2S D 420. 35 420. 9 H O (1-hydroxy-ethyl)-phenol Cl WCI OH ci 2-Chloro-6- (1-hydroxy-ethyl)-4- 1087 S, [2- (4-nitro-phenylsulfanyl)- C2lHl9CIN204S D 430. 90 431. 3 HO q', Yq benzylamino]-phenol Ci eNO2. N02 OH w I 2-Chloro-6- (1-hydroxy-ethyl)-4- 1088 , S [2- (4-methoxy-phenylsulfanyl)- C22H22CIN03S D 415. 93 416. 3 HO T 4 benzylamino]-phenol OMe. OH 2-Chloro-4- [2- (2-chloro- 1089 Jt d s phenylsulfanyl)-benzylamino]-6-C21H19C12NO2S D 420. 35 420. 9 (1-hydroxy-ethyl)-phenol HO OH N 2-Chlofo-4- [2- (3-chloro- 1090 phenylsulfanyl)-benzylaminol-6-C2lHl9Ct2NO2S D 420. 35 420. 8 HO" Y (l-hydroxy-ethyl)-phenol OH n cul N 2-Chloro-4- [2- (3, 4-dichloro- 1091 phenylsulfanyl)-benzylamino]-6-C2lHl8Cl3NO2S D 454. 80 455. 2 Ho I (1-hydroxy-ethyl)-phenol ci cl OH N \ I N- [4- (2- { [3-Chloro-4-hydroxy-5- (1-hydroxy-ethyl)-phenylamino]- i methyl}-phenylsulfanyl)-phenyl]- acetamide cri NHAc OH N 2-Chloro-6- (l-hydroxy-ethyl)-4- 1093/+ s N [2-(quinolin-7-ylSulfanyl)-C24H21CIN202S D 436. 95 437. 3 S N benzylaminol-phenol NO2 N02 OH N02 2-Chloro-4- [2- (4-cWoro- phenylsulfanyl)-5-nitro- s benzylamino]-6- (l-hydroxy-ethyl)- HO phenol cl ci NO2 OH 2-Chloro-4- (l-hydroxy-ethyl)-6- 1095 N (5-nitro-2-p-tolylsulfanyl-C22H21CIN204S D 444. 93 445. 3 HOC S\Cx benzylaniino)-phenol ci NHZ Ohm 4- [5-Amino-2- (4-chloro- 1096 N phenylsulfanyl)-benzylamino]-2-C2lH2OCl2N202S D 435. 37 435. 6 Ho s chloro-6- (l-hydroxy-ethyl)-phenol ci 0'< a OH 2-Chloro-4- [2- (4-chloro- 1097 e o2s benzenesulfonyl)-benzylarnino]-6-C21H19C12NO4S D 452. 35 452. 5 (1-hydroxy-ethyl)-phenol ci ci OH 2-Hydroxymethyl-4- (2- 1098 phenylsulfanyl-benzylamino)-C20Hl9NO2S D 337. 44 337. 8 Ho phenol OH OU 1099 2-Hydroxymethyl-4.- (2-p- C21H21N02S D 351. 46 351. 8 Ho s tolylsulfanyl-benzylamino)-phenol H OH 4- [2- (4-Chloro-phenylsulfanyl)- 1100 s benzylaminol-2-hydroxymethyl-C20Hl8CIN02S D 371. 88 371. 9 Ho phenol ci Oh 2-Hydroxymethyl-4- [2- (4-rlitro- 1101 phenylsulfanyl)-benzylaminol-C20Hl8N204S D 382. 43 382. 7 "o I phenol i NO2 OU 2-Hydroxymethyl-4- [2- (4- 1102 HOX S methoxy-phenylsulfanyl)-C21H21NO3S D 367. 46 367. 9 < benzylamino]-phenol OMe OH 4- [2- (2-Chloro-phenylsulfanyl)- 1103 HOAJ S benzylamino]-2-hydroxymethyl-C20H18CINO2S D 371. 88 371. 9 Ho phenol ci OH 4- [2- (3-Chloro-phenylsulfanyl)- 1104 benzylamino]-2-hydroxymethyl-C20H18CIN02S D 371. 88 371. 9 HOw ci phenol OH N 4- [2- (3, 4-Dichloro- 1105 0I, J s a phenylsulfanyl)-benzylamino]-2-C20H17C12NO2S D 406. 33 406. 5 hydroxymethyl-phenol OH OH [ N- (4- {2- [ (4-Hydroxy-3- 1106 hydroxymethyl-phenylamino)-C22H22N203S D 394. 49 349. 9 HOw Sg : +] methyl]-phenylsulfanyl}-phenyl)- acetamide NHAc OH N 1107 \ 2-Hydroxymethyl-4- [2- (quinolin- C23H20N202S D 388. 48 388. 8 HO S 7-ylsulfanyl)-benzylamino]-phenol Ho, OU oH f< r 4- [2- (4-Chloro-phenylsulfanyl)-5- 1108 NC Ns/tZ nitro-benzylamino]-2-C20H17CIN204S D 416. 88 417. 2 H s hydroxymethyl-phenol ci N02 OH OH fl 1109 w N I 2-Hydroxymethyl-4- (5-nitro-2-p- C21H20N204S D 396. 46 396. 8 tolylsulfanyl-benzylamino)-phenol NOS NHZ OH 4- [5-Amino-2- (4-chloro- 1110 N phenylsulfanyl)-benzylamino]-2-C20Hl9CIN202S D 386. 90 387. 1 Ho s hydroxymethyl-phenol i ci OH 4- [2- (4-Chloro-benzenesulfonyl)- 1111 , ozs benzylamino]-2-hydroxymethyl-C20H18CIN04S D 403. 88 44. 0 Ho, O, S phenol ci 0 w 1- [3-Chloro-2-hydroxy-5- (2- 1112) t s phenylsulfanyl-benzylanlino)-C21H18CIN02S D 383. 89 384. 2 HO phenyl]-ethanone ci o fi o i N 1- [3-Chloro-2-hydroxy-5- (2-p- 1113 | tolylsulfanyl-benzylamino)-C22H20C1N02S D 397. 92 398. 2 Ho s¢Ds phenyl]-ethanone cul cl H 1- {3-Chloro-5- [2- (4-chloro- 1114 s phenylsulfanyl)-benzylamino]-2-C21H17C12N02S D 418. 34 418. 8 HO T \CI hydroxy-phenyl}-ethanone ci cl 1- {3-Chloro-2-hydroxy-5- [2- (4- - l- {3-Chloro-2-hydroxy-5- [2- (4- 1115 nitro-phenylsulfanyl)-C2lHl7CIN204S D 428. 89 429. 3 Ho benzylamino]-phenyl}-ethanone cl NO 2 0 1116 l- (3-Chloro-2-hydroxy-5- [2- (4- methoxy-phenylsulfanyl)-C22H20CIN03S D 413. 92 414. 5 0 benzylaminol-phenyll-ettianone cul OMe 0 1- {3-Chloro-5- [2- (2-chloro- 1117 phenylsulfanyl)-benzylamino-2-CZ1H17C12N02S D 418. 34 418. 6 hydroxy-phenyl I-ethanone cl ci H W 1- {3-Chloro-5- [2- (3-chloro- 1118 phenylsulfanyl)-benzylamino]-2-C2lHl7Cl2NO2S D 418. 34 418. 5 hydroxy-phenyl}-ethanone ci 0 1- {3-Chloro-5- [2- (3, 4-dichloro- 1119 s ci phenylsulfanyl)-benzylamino]-2-C2lHl6Cl3NO2S D 452. 78 453. 0 hydroxy-phenyl}-ethanone ci ci o N- (4- {2- [ (3-Acetyl-5-chloro-4- hydroxy-phenylamino)-methyl]- HO phenylsulfanyl)-phenyl)- HO ci acetamde NHZ '-'NHAc 0 fol 1- {3-Chloro-2-hydroxy-5- [2- 1121) (quinolin-7-ylsulfanyl)-C24Hl9ClN202S D 434. 94 435. 2 s N-benzylamino]-phenyl}-ethanone NO2 d ci o I 1- {3-Chloro-5- [2- (4-chloro- 1122 JleNN\C phenylsulfanyl)-5-nitro-C21H16C12N204S D 463. 33 463. 7 s benzylaminol-2-hydroxy-phenyl}- HO ethanone ci ci NO2 ° ! ! l- [3-CMoro-2-hydroxy-5- (5-nitro- 1123 N 2-p-tolylsulfanyl-benzylamino)-C22Hl9CIN204S D 442. 92 443. 2 , S phenyl]-ethanone HO ci NH2 o H 1-15- [5-Amino-2- (4-chloro- 1124 N phenylsulfanyl)-benzylamino]-3-C2lHl8Cl2N202S D 433. 35 433. 6 chloro-2-hydroxy-phenyl}- Ho S ethanone ci 0 1- {3-Chloro-5- [2- (4-chloro- 1125-) + benzenesulfonyl)-benzylamino]-2-C21H17CI2NO4S D 450. 33 450. 5 HO ; 2S I hydroxy-phenyl}-ethanone c I ci 1126 HOOC N 2-Hydroxy-5- (2-phenylsulfanyl- C20Hl7NO3S D 351. 42 351. 6 HOw S [benzylamino)-benoic acid HO H u HOOC N '2-Hydroxy-5- (2-p-tolylsulfanyl- -" ' benzylamino)-benzoic acid H HOOC\ ^/N 5- [2- (4-Chloro-phenylsulfanyl)- w 1128 benzylaniinol-2-hydroxy-benzoic C20I-Il6CIN03S D 385. 86 385. 1 HO acid ci Hoot N 2-Hydroxy-5- [2- (4-nitro- 1129 phenylsulfanyl)-benzylaminol-C20Hl6N205S D 396. 11 396. 4 HO I benzoic acid 'nô z / 1130 Hooc N 2-Hydroxy-5- [2- (4-methoxy- 1130 A J s phenylsulfanyl)-benzylamino]-C21H19N04S D 381 44 381. 6 benzoic acid OMe me H HOOC N 5- [2- (2-Chloro-phenylsulfanyl)- 1131 D s benzylaIriino]-2-hydroxy-benzoic C20H16CIN03S D 385. 86 386. 0 HO-"'Y add Ho acid ci HOOG N 5- [2- (3-Chloro-phenylsulfanyl)- 1132 i J'benzylanuno]-2-hydroxy-bsnzoic C20H16QN03S D 385. 86 386. 0 HO v aCld / HOOC N 5- [2- (3, 4-Dichloro- 1133 X s a phenylsulfanyl)-benzylamino]-2-C20H15C12NO3S D 420. 31 420. 7 HO a s ci hydroxy-benzoic acid ci Hooc N 5- [2- (4-Acetylarriino- 1134 XJ s phenylsulfanyl)-benzylarnino]-2-C22H20N204S D 408. 47 408. 7 Ho I hydroxy-benzoic acid NHAc H Hooc N 2-Hydroxy-5- [2- (quinolin-7- 1135 ^II/J ylsulfanyl)-benzylamino]-benzoic C23H18N203S D 402. 46 402. 8 1135 acid Ho NO, H 5- [2- (4-Chloro-phenylsulfanyl)-5- 1136 < nitro-benzylamino]-2-hydroxy-C20HlSCIN205S D 430. 86 430. 9 HO » J S benzoic acid fact NOS H 2-Hydroxy-5- (5-nitro-2-p- 1137 Hooc I N w tolylsulfanyl-benzylamino)-C21H18N205S D 410. 44 410. 7 benzoic acid HO "i ! HO NH, Nu2 HOOC N 5- [5-Amino-2- (4-chloro- 1138 N phenylsulfanyl)-benzylamino]-2-C2OHl9CIN202S D 386. 90 387. 2 i s hydroxymethyl-phenol s ci Hooc r w (5- [2- (4-Chloro-benzenesulfonyl)- 1139 < o benzylamino]-2-hydroxy-benzoic C20H 16ClNO5S D 403. 88 404. 1 HO 02S acid cl / F N 2-Fluoro-6-nitro-4- (2- 1140 j ! J'phenylsulfanyl-benzylainino)-C19H15FN203S D 370. 40 370. 8 Ho s phenol rio2 i H F HN03 2-Fluoro-6-nitro-4-(2-p-C20H17FN203S D 384. 43 384. 9 C20H17FN203S D 384. 43 384. 9 1141 Ho s tolylsulfanyl-benzylamino)-phenol NO2 N02 N 4- [2- (4-Chloro-phenylsulfanyl)- 1142 benzylaminol-2-fluoro-6-nitro-C19Hl4CIFN203S D 404. 84 405. 0 Ha acI phenol l NoZ ci I F HNog3 2-Fluoro-6-nitro-4-[2-(4-nitro- 1143 t S phenylsulfanyl)-benzylamino]-C19H14FN305S D 415. 40 415. 8 HO N02 N02 phenol Nô2 i top / 2-Fluoro-4- [2- (4-methoxy- 1144 , S phenylsulfanyl)-benzylamino]-6-C20H17FN204S D 400. 43 400. 9 Ho I nitro-phenol OMe / F N \ I 4- [2- (2-Chloro-phenylsulfanyl)- 1145 benzylamino]-2-fluoro-6-nitro-C19Hl4CIFN203S D 404. 84 405. 0 NOS B phenol N02 cri H r F N 4- [2- (3-Chloro-phenylsulfanyl)- 1146 benzylaminol-2-fluoro-6-nitro-C19Hl4CIFN203S D 404. 84 405. 0 Ho : q H, S Cl phenol NO2 / N 4- [2- (3, 4-Dichloro- 1147 JI S Ci phenylsulfanyl)-benzylamino]-2-C19H13C12FN203S D 439. 29 439. 9 HO T < fluoro-6-nitro-phenol NO2 WCI F NXS N-(4-{2-[(3-Fluoro-4-hydroxy-5- nitro-phenylamino)-methyl]-C21H18FN304S D 427. 45 427. 9 \<"Y phenylsulfanyl}-phenyl)- Ho acetamide NOa \ ""NHAc H 1149 2-E ; 2-Fluoro-6-nitro-4- [2- (quinolin-7- C22H16FN303S D 421. 45 421. 6 H s N ylsulfanyl)-benzylaminol-phenol HO NO2 l N02 H 4- [2- (4-Chloro-phenylsulfanyl)-5- 1150 F,/t nitro-benzylamino]-2-fluoro-6-C19H13CIFN305S D 449. 84 450. 1 s nitro-phenol N02 ex Lut) H 1 1151 F : qN 2-Fluoro-6-nitro-4- (5-nitro-2-p- C20Hl6FN304SD429A2 429. 8 tolylsulfanyl-benzylamino)-phenol N02 Nô N02 NHZ H 4- [5-Arnino-2- (4-chloro- 1152 F N t phenylsulfanyl)-benzylamino]-2-C19HlSCIFN302S D 419. 86 420. 2 HOeJ S fluoro-6-nitro-phenol HO) y) H FX N 4- [2- (4-Chloro-benzenesulfonyl)- 1153 benzylamino]-2-fluoro-6-nitro-C19H15C1FN205S D 436. 84 437. 1 02S phenol Ho NO, Cl 1154 HNJ 2, 6-Dichloro-4- (3-phenoxy- C19H15C12N02 D 360. 23 360. 5 Ho , benzylamino)-phenol Ci Cl 1155 I i 2, 6-Dichloro-4- [3- (4-chloro- C19H15C13N02 D 394. 68 395. 0 Ho i I phenoxy)-benzylamino]-phenol cul cl CI NO 4- [3- (4-tert-Butyl-phenoxy)- 1156 t henzylãmino3-2, 5-dichoro-phenol C23H23CI NO2 D 416. 34 416. 8 ci ( y H ci N 0 4- (3-Benzyloxy-benzylamino)-2, 6- C20H17C12N02 D 374. 26 374. 6 1157 Ho , dichloro-phenol ci CIN N 1158 HO 4- (2-Benzyloxy-benzylamino)-2, 6- C2OHl7Cl2NO2 D 374. 26 374. 6 dichloro-phenol 6 ci H H 1159 CIPr N/<} 2, 6-Dichloro-4-[(naphthalen-1-C17H13C12NO D 318. 20 318. 6 ylmethyl)-amino]-phenol HO cri ^/su Fl I CI N 2, 6-Dichloro-4- (4-methylsulfanyl- 1160 benzylamino)-phenol HO CRI H ci N w 2, 6-Dichloro-4- (2-ethylsulfanyl- 1161'"q benzylamino)-phenol C15H mo / CI N 2, 6-Dichloro-4- (2-morpholin-4-yl- C17H18C12N202 D 353. 24 353. 6 a tOD benzylammo)-phenol T r 1 HO 0 ci N w S 2, 6-Dichloro-4- { [2- (4-chloro- 1163 phenylsulfanyl)-thiophen-3-C17H12C13NOS2 D 416. 77 416. 9 HI _ci ylmethyl]-amino I-phenol ci N N 2, 6-Dicbloro-4- [ (5-phenyl-2H- 1164 imidazol-4-ylmethyl)-amino]-C16H13C12N30 D 334. 20 334. 6 Ho 1 phenol ci Br N 4- [ (5-Bromo-thiophen-2- 1165 cw N ylmethyl)-amino]-2, 6-dichloro-Cl lH8BrC12NOS D 353. 06 353. 4 phenol HO ci I CI No 1166 Ho I , 2, 6-Dichloro-4- [3- (4-methoxy- C20H17C12N03 D 390. 26 390. 6 cl ci "lo H S S HNJ\ 2, 6-Dichloro-4- (3-methyl- 1167 C14H13C12N0 D 282. 17 282. 4 HO HO Cl / H 1168 ClA CFs 2, 6-Dichloro-4-(3-trifluoromethyl-C14HlOC12F3NO D 336. 14 336. 5 | 1168 3 C14H10C12F3N0 D 336. 14 336. 5 , benzylamino)-phenol HO CRI H ! 1169 ClA N qz 2, 6-Dichloro-6-(2-chloro-6-fluoro-C13H9C13FN0 D 320. 57 320. 8 HO HOLZ Cl OH 1170 N 0 4- (3-Phenoxy-benzylamino)- C19Hl7NO3 D 307. 34 307. 8 C19H17N03 D 30734 307. 8 HO"j benzene-1, 3-diol OH ohm 4- [3- (4-Chloro-phenoxy)- benzylamino]-benzene-1, 3-diol cri a Oh \ Nv v'O 1172 I i, 4- [3- (4-tert-Butyl-phenoxy)- C23H25N03 D 363. 45 363. 9 Ho I benzylamino-benzene-1, 3-diol OH OH fl 1173 N 0 4- (3-Benzyloxy-benzylamino)- C20Hl9NO3D 321. 37 321. 6 benzene-l, 3-diol OH oh N,\ OH f 1174 Ho C2oH19N03 D 321. 37 321. 5 benzene-1, 3-diol OH 4- [ (Naphthalen-1-ylmethyl)- oj ! ! anuno]-benzene-l, 3-diol' HA /su OH 4- (4-Methylsulfanyl- C14H15N02S D 261. 34 261. 7 1176 I w benzylamino)-benzene-1, 3-diol HO OH 4- (2-Ethylsulfanyl-benzylamino)- 1177 , S benzene-1, 3-diol C15H17N02S D 275. 37 275. 9 noj [tN s benzene-1, 3-diol OH OH r. i t H JLJJ 4- (2-Morpholin-4-yl- 1178 N. benzylamino)-benzene-l, 3-diol OH N w S 4- { [2- (4-Chloro-phenylsulfanyl)- 1179 jf X4S thiopheñ-3-ylmethyl]-amino}-C17H14CINO2S2 D 363. 88 364. 1 S-0-Cl benzene-1, 3-diol /cri OH NEZ N I/N 4- [ (5-Phenyl-2H-imidazol-4- 0"&H N . . \ ylmethyl)-amino]-benzene-l, 3-diol HO Br H < 2-[(5-Bromo-thiophen-2- 1181 CN ylmethyl)-aminol-4, 6-dichloro-3- C12HIOBrCl2NOSD367. 09 367. 4 methyl-phenol a OH 0 \ N v v'O 1182 I i 4- [3- (4-Methoxy-phenoxy)- C20H19N04 D 337. 37 337. 8 Ho I benzylamino]-benzene-1, 3-diol pro Oh 1183 N I 4- (3-Methyl-benzylamino)- C14H15N02 D 229. 27 229. 6 oh Hou Ho OH 1184 OH/C1 4-(3-Trifluoromethyl-C14H12F3NO2 D 283. 25 283. 6 benzylamino)-benzene-1, 3-diol HO Ho OH H F/ 1185 OH 4- (2-Chloro-6-fluoro- C13HIlCIFN02D267. 68 268. 0 1185 w benzylamino)-benzene-1, 3-diol cri HO H ci N 0 2-Chloro-4- (3-phenoxy- 1186 benzylamino)-phenol HO I \ H cl N 0 2-Chloro-4- [3- (4-chloro-phenoxy)- HO ; y 3 benzylamino]-phenol ) Cl i \ 6 t ci CRI 1188 (i, 4- [3- (4-tert-Butyl-phenoxy)- C23H24C1N02 D 381. 90 382. 2 benzylaminol-2-chloro-phenol H ci No 4-3-Benz lox-benz larnino-2- HO t) 1 1189 , chloro-phenol HA ci N CI N 0 4- (2-BenzyIoxy-benzylamino)-2- f BI NJ ; 3 i 1190 HO chloro-phenol C20H18C1N02 D 339. 82 340. 1 11 t 1191 C N I 2-Chloro-4- [ (naphthalen-l- t) ! ! ylmethyl)-amino]-phenol HO I I s H 2-Chloro-4- (4-methylsulfanyl- C14H14CINOS D 279. 79 280. 2 HOw HO H 1193 C \ \ 2-Chloro-4- (2-ethylsulfanyl- C15H16C1NOS D 293. 81 2943 1193 Ho4J S) benzylamino)-phenol HO H 2-Chloro-4- (2-morpholin-4-yl- HOw f N) benzylamino)-phenol HO cl N Cs 2-Chloro-4-{ [2-(4-chloro- 1195 < \ phenylsulfanyl)-thiophen-3-C17H13C12NOS2 D 382. 33 382. 6 Ho'v ylmethyl]-amino}-phenol /cri Nez ci N 2-Chloro-4- [ (5-phenyl-2H- 1196 < t imidazol-4-ylmethyl)-amino]-C16H14CIN30 D 299. 75 300. 2 HO phenol Br Ber 4- [ (5-Bromo-thiophen-2- 1197 c, : ylmethyl)-amino]-2-chloro-phenol ho'v CL 1198 Ho I 2-Chloro-4- [3- (4-methoxy- C20H18CIN03 D 355. 81 356. 5 phenoxy)-benzylamino]-phenol H o ci N 2-Chloro-4- (3-methyl- 1199 w 2-Chl4H14CINO D 247. 72 248. 5 benzylamino)-phenol HA Structure Chemical name Formula Synthesis MolWeight MS data methods cr r" 2-Chloro-4- (3-trifluoromethyl- 1200 w F C14H11ClF3N0 D 30I. 69 302. 2 benzylamino)-phenol HA' F j 1201 ci N 2-Chloro-4- (2-chloro-6-fluoro- C13111OC12FNO D 286. 13 286. 6 ! ! ! ! benzylaimno)-phenol cri HO Hz rif 1202 oa N 0 2-Fluoro-4- (3-phenoxy- C19Hl6FN02 D 309. 33 309. 8 HO t3 benzylammo)-phenol F N 1203 Ho je 2-Fluoro-4- [3- (4-chloro-phenoxy)- C19H15CIFN02 D 343. 77 344. 0 benzylammo]-phenol Ct r v'O 1204 : :, 4- [3- (4-tert-Butyl-phenoxy)- S benzyla7mno]-2-fluoro-phenol H H < s I 1205 4- (3-Benzyloxy-benzylamino)-2- C20H18FN02 D 323. 36 323. 8 Ho fluoro-phenol .. F N 1206 I i o 4- (2-Benzyloxy-benzylamino)-2- Ho fluora-phenol C20H18FN02 D 323. 36 323. 8 w vs 1207 F N 2-Fluoro-4- [ (naphthalen-l- C17Hl4FNO D 267. 30 267. 7 ") a yhnethyl)-amino]-phenol HO 2-Fluoro-4- (4-methylsulfanyl- 1208 I w benzylamino)-phenol C14H14FNOS D 263. 33 263. 5 HO r H I F N 2-Fluoro-4- (2-ethylsulfanyl- 1209 C15H16FNOS D 277. 36 277. 8 benzylamino)-phenol / 2-Fluoro-4- (2-morpholin-4-yl- N benzylammo)-phenol Ou zu F N, 2-Fluoro-4-1 [2- (4-chloro- 1211 phenylsulfanyl)-thiophen-3-C17Hl3CIFNOS2 D 365. 87 366. 0 Ho ylinethyl]-amino}-phenol cri Nez H F N 2-Fluoro-4- [ (5-phenyl-2H- 1212 II | t imidazol-4-ylmethyl)-amino]-C16H14FN30 D 283. 30 283. 8 Ho phenol +/ Br 1213 F NJf 4-[(5-Bromo-thiophen-2-C1 IH9BrFNOS D 302 16 302. 5 ylmethyl)-amino]-2-fluoro-phenol HOUA H v _O 1214 Ho I i, 2-Fluoro-4- [3- (4-methoxy- C20H18FN03 D 339. 36 339. 8 phenoxy)-benzylamino]-phenol po F N 2-Fluoro-4- (3-methyl- 1215 W C14H14FN0 D 231. 27 231. 4 Ho HOLZ 1216 F N \ 2-Fluoro-4- (3-trifluoromethyl- -'cF C14H11F4N0 D 285. 24 285. 5 benzylamino)-phenol HO F/ 1217 F N 2-Fluoro-4- (2-chloro-6-fluoro- C13HlOClF2NO D 269. 67 270. 1 benzylamino)-phenol ci Ha F N I o 2 6-Difluoro-4- H N 0 2, 6-Difluoro-4- (3-phenoxy- C19Hl5F2NO2 D 327. 32 327. 6 1218 Fq berizylamino)-phenol HO H I F \. N W//O 1219 Ho I , 2, 6-Difluoro-4- [3- (4-chloro- C19H14CiF2N02 D 361. 76 362. 0 phenoxy)-benzylamino]-phenol FI cri ruz 0 4- [3- (4-tert-Butyl-phenoxy)- 383. 8 benzylamino]-2, 6-difluoro-phenol F F NEZ 1221 4- (3-Benzyloxy-benzylamino)-2, 6- 1221 C20H17F2N02 D 341. 35 341. 7 q difluoro-phenol N) 03 4 F H FqN 1222 No I i o 4- (2-Benzyloxy-benzylamino)-2, 6- C20H17F2N02 D 341. 35 341. 7 difluoro-phenol F/ H 2, 6-Difluoro-4- [ (naphthalon-l- C17Hl3F2NO D 285. 29 285. 6 1223 I C17H13F2N0 D 285. 29 285. 6 1223 ylmcthyl)-amino]-phenol HO s F H I 1224 nu 2, 6-Difluoro-4- (4-methylsulfanyl- HOC benzylamino)-phenol HO F H 1225 HN $3 2, 6-Difluoro-4- (2-ethylsulfanyl- 1225 C15H15F2NOS D 295. 35 295. 7 -phenol Ho Ho Zu 1226 2, 6-Difluoro-4- (2-morpholin-4-yl- C17H18F2N202 D 320. 33 320. 8 Ho benzylamino)-phenol F O zu H s F N S 2, 6-Difluoro-4- [2- (4-chloro- 1227 # s/+ phenylsulfanyl)-thiophen-3-C17Hl2CIF2NOS2 D 383. 86 384. 2 Who _ci ylmethyl]-amino}-phenol F r Nez H N F No \N 2, 6-Difluoro-4- [ (5-phenyl-2H- 1228 imidazol-4-yhnethyl)-aminc]-C16Hl3F2N30 D 301. 29 301. 6 Ho phenol F Br 4- [ (5-Bromo-thiophen-2- 1229 ylmethyl)-amino]-2, 6-difluoro- Cl lH8BrF2NOS D 320. 15 320. 4 phenol HO F H 2 6-Difluoro-4- [3- (4-methoxy- 1230 Ho I /'C20H17F2N03 D 357. 35 357. 6 F C phenoxy)-benzylamino]-phenol Xi H F 2, 6-Difluoro-4- (3-methyl- 1231 I'C14H13F2N0 D 249. 26 249. 6 H HA F hi N CF, 2, 6-Difluoro-4- (3-trifluoromethyl-- 1232 3' y C14H10FSN0 D 303. 23 303. 7 HO F F F/ 1233 F p 2, 6-Difluoro-4- (2-chlorc-6-fluoro- C13H9CIF3NO D 287. 66 288. 1 i ! J benzylammo)-phenol ho nu F F 1234 HO NH N- (2, 4-Dihydroxy-phenyl)-C- /\ phenyl-methanesulfonamide C13H13N04S B 279. 31 279. 8 o Ho NH 1235'\/-P/'o Butane-1-sulfonic acid (2 4- s'C10H15N04S B 245. 30 245. 6 dihydroxy-phenyl)-amide Octane-1-sulfonic acid (2, 4- 1236 o dihydroxy-phenyl)-amide po HO OH fYJ HOO Propane-2-sulfonic acid (2, 4- OHO e dihydroXy-phenyl)-arnidO or cri HO NH N- (3, 5-Dichloro-4-hydroxy- 1238 v o phenyl)-C-phenyl-C13H11C12N03S B 332. 20 332. 4 cl meflmnesulfonamide ei 1239 Ho NH Butanl-sulfonic acid (3 5- 1239 \S., o CtOH13Cl2NO3S B 298. 19 298. 5 ci Octane-l-sulfonic acid (3, 5- C14H21C12N03S B 354. 29 354. 6 N,/i dichloro-4-hydroxy-phenyl)-arnide 0 HO ci CI 1241 Ho NHo Propane-2-sulfonic acid (3, 5- C9H11C12N03S B 284. 16 284. 5 dichloro-4-hydroxy-phenyl)-amide cri HO-P-, NH 1242 HO NH N- (3-Chloro-4-hydroxy-phenyl)- ci °S C-phenyl-methanesulfonamide Ho nu 1243 HO NH Butane-1-sulfonic acid (3-chloro- O, 4-hydroxy-phenyl)-amide ci 1244 H o Octane-1-sulfonic acid (3-chloro-C14H22C1N03S B 319. 85 320. 3 4-hydroxy-phenyl)-amide 0 HO C ! "Propane-2-sulfonic acid (3-chloro- 1245 ci 4-hydroxy-phenyl)-amide cri Ho NHO N- (3-Fluoro-4-hydroxy-phenyl)-C- 1246 os C13H1. 2FN03S B 281. 30 281. 8 /\ phenyl-methanesulfonamide /\ 1247 H s ! Butane-1-sulfonic acid (3-fluoro-4-C10H14FN03S B 247. 29 247. 8 F °'\ hydroxy-phenyl)-aBide 1248 Octane-1-sulfonic acid (3-fluoro-4-C14H22FN03S B 303. 39 303. 8 l 0 hydroxy-phenyl)-amide Ho HO 1249 \/ Propane-2-sulfomcacid (3-Quoro- c9H12FN03S B 233. 26 233. 7 /o \ 4-hydroxy-phenyl)-amids R F N- (3, 5-Difluoro-4-hydroxy- 1250"°\/'o phenyl)-C-phenyl-C13H11F2N03S B 299. 29 300. 8 F methanesulfonamide F 1251 , o ClOH13F2NO3S B 265. 28 265. 7 iji \/\0,..-.,,, ., LluHi.) r2J\U3b H 6j. 2o 2o.)./ difluorc-4-hydroxy-phenyl)-amide Octane-1-sulfonic acid (3, 5- 1252 F I \ N\SO difluoro-4-hydroxy-phenyl)-amide C14H21F2N03S B 321. 38 321. 8 Ho HO A o HO Y F F 1253 Ho NH Propane-2-sulfonic acid (3 5- o s' difluoro-4-hydroxy-phenyl)-amide C9H11F2N03S B 251. 25 251. 6 s difluoro-4-hydroxy-phenyl)-amide OH OH 1254 0-acid hyl ester C13H19N04 F, G, H 253. 29 253. 7 0 acid hexyl ester NH 0 Cl OH 1255 CCI (3, 5-Dichloro-4-hydroxy-phenyl)-Cl3H17C12NO3 F, G, H 306 18 306. 4 0 carbamic acid hexyl ester -NH 0 Ci OH 1256 (3-Chloro-4-hydroxy-phenyl)-C13Ht8CIN03 F, G, H 271. 74 272. 1 carbamic acid hexyl ester NH zozo H 1257 (3-Fluoro-4-hydroxy-phenyl)-C13Hl8FN03 F, G, H 255. 29 255. 6 - carbamic acid hexyl ester NH zozo Br OH ( (3, 5-Dibromo-4-hydroxy-phenyl)- 1258 o Br carbamic acid hexyl ester NH -o F OH 1259 o $ (3, 5-Difluoro-4-hydroxy-phenyl)-C13H17F2NO3 F G, H 273 28 273 6 l 1259 0-carbamic acid hexyl ester ohm 0 OH N N- [3- (2, 4-Dihydroxy-phenyl)- 1260 y ureido]-4-methyl-pentanoic acid C15H22N205 A 310. 35 310. 7 Ho ° o ethyl ester N N 2- [3- (3, 5-Dichloro-4-hydroxy- 1261 t J Y s phenyl)-ureido]-4-methyl-C15H20CI2N204 A 363. 24 363. 6 Who T k pentanoic acid ethyl ester ci H H ci N N 2- [3- (3-Chloro4-hydroxy-phenyl)- 12Ti ureido]-4-methyl-pentanoic acid C15H21C1N204 A 328. 79 329. 1 HO ethyl ester F N N 2- [3- (3-Fluoro-4-hydroxy-phenyl)- 1263 y ureido]-4-methyl-pentanoic acid C15H21FN204 A 312. 34 312. 8 Ho/v ° o o eth 1 este H H \ 1 F N N 2- [3- (3, 5-Difluoro-4-hydroxy-4- 1264 | phenyl)-ureido]-4-methyl-C15H20F2N204 A 330. 33 330. 8 H 0 0 0 pentanoic acid ethyl ester F < F N N 2- [3- (3, 5-Dibromo-4-hydroxy-4- 1265 t methyl-phenyl)-ureido]-4-methyl-ClSH2OBr2N204 A 452. 14 452. 3 HO anoic acid ethyl ester Br OH 2- [3- (2, 4-Dihydroxy-phenyl)- 1266 N N ureido]-3-phenyl-propionic acid C18H20N205 A 344. 36 344. 8 ethyl ester HOw 0+0/\, l 2- [3- (3, 5-Dichloro-4-hydroxy- 1267 m I N. N phenyl)-ureido]-3-phenyl-C18H18C12N204 A 397. 25 397. 6 propionic acid ethyl ester 0 cl 2- [3- (3-Chloro-4-hydroxy-phenyl)- 1268 H H ureido]-3-phenyl-propionic acid C18H19CIN204 A 362. 81 363. 0 ethyl ester ") : > 0 HO 2- [3- (3-Fluoro-4-hydroxy-phenyl)- 1269 F N N ureido]-3-phenyl-propionic acid C18H19FN204 A 346. 35 346. 7 ethyl ester Ho 0 o---- 2- [3- (3, 5-Difluoro-4-hydroxy- 1270 F NN phenyl)-ureido]-3-phenyl-C18H18F2N204 A 364. 34 364. 8 0 propionic acid ethyl ester Ha 0 0 F H H 2- [3- (3, 5-Dibromo-3-fluoro-4- 1271 Br N N hydroxy-phenyl)-ureido]-3-phenyl-C18H18Br2N204 A 486. 15 486. 2 propionic acid ethyl ester Ho 0 0 Br OH N 0 N O 1272 Ho I i 3, 5, 5-Trimethyl-hexanoic acid C15H23N03 C 265. 35 265. 7 (2, 4-dihydroxy-phenyl)-amide H N 3, 5, 5-Trimethyl-hexanoic acid 1273 Ho (3, 5-dichloro-4-hydroxy-phenyl)- C15H21CI2N02 C 318. 24 318. 5 ci amide H ci N 0 1274 Ho I 3, 5, 5-Trimethyl-hexanoic acid (3- chloro-4-hydroxy-phenyl)-amide H F N 1275 Ho 3, 5, 5-Trimethyl-hexanoic acid (3- fluoro-4-hydroxy-phenyl)-amide H H 3, 5, 5-Trimethyl-hexanoic acid 1276 Ho (3, 5-difluoro-4-hydroxy-phenyl)- C15H21F2N02 C 285. 33 285. 7 F amide H Br N O 3, 5, 5-Trimethyl-hexanoic acid 1277 HO (3, 5-dibromo-4-hydroxy-phenyl)-ClSH21Br2NO2 C 407. 14 407. 3 Br amide Oh. N cl 1278 1- (3-Benzothiazol-2-yl-5-chloro-4- K followed by i l ° 0/hydroxy-phenyl)-3-te t-butyl-nrea p L J ICI O OH N-- CI 1279 1- (3-Benzothiazol-2-yl-5-chloro-4- K followed by ¢ O ; hydroxy-phenyl) S3-benzyl-urea t t Hz il OH N-- OH N cl 1- (3-Denzothiazol-2-yl-5-chloro-4- K followed by hydroxy-phenyl)-3-phenethyl-urea A H L H : N C _ oh s Cl'N 1- (3-Benzothiazol-2-yl-5-chloro-4- K followed by 1281 hydroxy-phenyl)-3-isopropyl-C17H16C1N30S2 I 377. 9 378. 1 thiourea "TY tir y s oH s ci l 1282 N 1- (3-Benzothiazol-2-yl-5-chloro-4- C18Hl8CIN3082 K followed by 391. 9 392. 1 H hydroxy-phenyl)-3-tert-butyl- HN N>v| thiourea . _ _ OH S 1283 ci N 3, 5, 5-Trimethyl-hexanoic acid (3-K followed by benzothiazol-2-yl-5-chloro-4-C22I-I25CIN202S c 417. 0 417. 2 hydroxy-phenyl)-amide han o''L oh s ci w N- (3-Benzothiazol-2-yl-5-chloro- K followed by 4-hydroxy-phenyl)-3-phenyl-C22Hl7CIN202S c 408. 9 409. 2 propionamide HN \ O H H 1- (4-Hydroxy-2-methyl-phenyl)-3-. 1285 p pentyl-urea C13H20N202 A 263. 31 256. 9 HA oh "Biphenyl-4-carboxylic acid (2, 4- HOJ (R N dihydroxy-phcnyl)-amide HO oc 1287 c I N Biphenyl-4-carhoxylic acid (3, 5- C20H15C12N02 C, E 358. 22 358. 5 dichloro-4-hydroxy-phenyl)-arnide ho HA OH 1288 w N 4- [ (Fut'an-2-ylmethyl)-amino]- C11H11N03 D 205. 21 205. 7 benzène-1, 3-diol HA zu H f 1289 2, 6-Dichloro-4- [ (uran-2- -'ylmethyl)-ammo]-phenol HO CUL H FN 1290 2, 6-Difluoro-4- [ (furan-2- \ ylmethyl)-a. mmo]-phenol HA OH Oh 1291 H 4- (2-Trifluorornethyl- C14Hl2F3NO2 D 283. 25 283. 5 benzylamino)-benzene-1, 3-diol CL H 1292 F 2, 6-Difluoro-4- (2-trifluoromethyl- cF3 benzylamino)-phenol HO F H 1293"YY N- (3, 5-DicMo4-hydroxy- C15H13C12N02 C, E 310. 18 310. 4 /o phenyl)-3-phenyl-propionamide HO c Nos H Cl N4 N-(3, 5-Dichloro-4-hydroxy-_ 1294 X o W phenyl)-2-(2-nitro-phenyl)-C14HlOC12N204 C, E 341. 15 341. 3 HO acetamide cl H CIK « NX O 2-Benzo [1, 3] dioxol-5-yl-N- (3, 5- 1295 J !. J S J./dichloM-4-hydroxy-phenyl)-C15H11C12N04 C, E 340. 16 340. 3 Ho acetamide ci H CIN 3-Methyl-but-2-enoic acid (3, 5- 1296 Ho / dichloro-4-hydroxy-phenyl)-amide C11H11C12N02 C 260. 12 260. 2 ci Ct H Naphthalene-2-carboxylic acid 1297 i I N w I (3, 5-dichloro-4-hydroxy-phenyl)- C17H11C12N02 C, E 332. 18 332. 4 ! !) amide HO HO"r CI H 1298 NYO N- (3, 5-Dichloro-4-hydroxy- C13H9Cl2NO2 C, E 282. 12 282. 3 o phenyl)-benzamide Ho Cl H CI \ N \ yod Furan-2-carboxylic acid (3, 5- C11H7C12N03 C, E 272. 08 272. 3 Ho I ° dichloro-4-hydroxy-phenyl)-amide cl I H J< CF-. benzylammo)-phenoi HO ! ci or a pharmaceutical acceptable salt or prodrug thereof.

Even more preferred compounds according to the present invention are those mentioned in any of the tables herein and those further disclosed and/or characterized in the examples.

As used herein, each of the following terms, used alone or in conjunction with other terms, are preferably used in the following meaning (except where noted to the contrary): The term"alkyl"refers to a saturated aliphatic radical containing from one to ten carbon atoms or a mono-or polyunsaturated aliphatic hydrocarbon radical containing from two to twelve carbon atoms, containing at least one double and triple bound, respectively."Alkyl" refers to both branched and branched alkyl groups. Preferred alkyl groups are straight chain alkyl groups containing from one to eight carbon atoms. More preferred alkyl groups are straight chain alkyl groups containing from one to six carbon atoms and branched alkyl groups containing from three to six carbon atoms. It should be understood that any combination term using an"alk"or"alkyl"prefix refers to analogs according to the above definition of"alkyl". For example, terms such as"alkoxy", "alkylthio"refer to alkyl group linked to a second group via an oxygen or sulfur atom. "Alkanoyl"refers to an alkyl group linked to a carbonyl group (C=O)."Substituted alkyl"refers to alkyl groups straight or branched further bearing one or more substituents. One substituent also means mono- substituted and more substitutents mean poly-substituted. It should be understood that any combination term using a"substituted alkyl"prefix refers to analogs according to the above definition of"substituted alkyl". For example, a term such as"substituted alkylaryl"refers to substituted alkyl group linked to an aryl group.

The term"cycloalkyl"refers to the cyclic analog of an alkyl group, as defined above, optionally unsaturated and/or substituted. Preferred cycloalkyl groups are saturated cycloalkyl groups, more particularly those containing from three to eight carbon atoms, and even more preferably three to six carbon atoms."Substituted cycloalkyl"refers to cycloalkyl groups further bearing one or more substituents."Mono-unsaturated cycloalkyl"refers to cycloalkyl containing one double bond or one triple bond."Poly-unsaturated cycloalkyl"refers to cycloalkyl containing at least two double bonds or two triple bonds or a combination of at least one double bond and one triple bond.

The term"alkenyl"refers to an unsaturated hydrocarbon group containing at least one carbon- carbon double bond, including straight-chain, branched-chain, and cyclic groups. Preferred alkenyl groups have one to twelve carbons. More preferred alkenyl groups have one to six carbons."Substituted alkenyl"refers to alkenyl groups further bearing one or more substitutents.

The term"cycloalkenyl"refers to the cyclic analog of an alkenyl group, as defined above, optionally substituted. Preferred cycloalkenyl groups are containing from four to eight carbon atoms. "Substituted cycloalkenyl"refers to cycloalkenyl groups further bearing one or more substituents. "Mono-unsaturated cycloalkenyl"refers to cycloalkenyl containing one double bond."Poly-unsaturated cycloalkenyl"refers to cycloalkenyl containing at least two double bonds.

The term"alkynyl"refers to an unsaturated hydrocarbon group containing at least one carbon- carbon triple bond, including straight-chain, branched-chain, and cyclic groups. Preferred alkynyl groups have one to twelve carbons. More preferred alkynyl groups have one to six carbons. "Substituted alkynyl"refers to alkynyl groups further bearing one or more substitutents.

The term"aryl"refers to aromatic groups having in the range of 6 to 14 carbon atoms and "substituted aryl"refers to aryl groups further bearing one or more substituents. It should be understood that any combination term using an"ar"or"aryl"prefix refers to analogs according to the above definition of"aryl". For example, a term such as"aryloxy"refers to aryl group linked to a second group via an oxygen.

Each of the above defined"alkyl","cycloalkyl", and"aryl"shall be understood to include their halogenated analogs, whereby the halogenated analogs may comprise one or several halogen atoms. The halogenated analogs thus comprise any halogen radical as defined in the following.

The term"halo"refers to a halogen radical selected from fluoro, chloro, bromo, iodo.

Preferred halo groups are fluoro, chloro and bromo.

The term"heteroaryl"refers to a stable 5 to 8 membered, preferably 5 or 6 membered monocyclic or 8 to 11 membered bicyclic aromatic heterocycle radical. Each heterocycle consists of carbon atoms and from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur. The heterocycle may be attached by any atom of the cycle, which preferably results in the creation of a stable structure. Preferred heteroaryl radicals as used herein include, for example, furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, tetrazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolizinyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, benzimidazolyl, benzthiazolyl, benzoxazolyl, purinyl, quinolizinyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl and phenoxazinyl."Substituted heteroaryl"refers to heteroaryl groups further bearing one or more substituents.

The term"heterocyclyl"refers to a stable 5 to 8 membered, preferably 5 or 6 membered monocyclic or 8 to 11 membered bicyclic heterocycle radical which may be either saturated or unsaturated, and is non-aromatic. Each heterocycle consists of carbon atom (s) and from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur. The heterocycle may be attached by any atom of the cycle, which preferably results in the creation of a stable structure. Preferred heterocycle radicals as used herein include, for example, pyrrolinyl, pyrrolidinyl, pyrazolinyl, pyrazolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, pyranyl, thiopyranyl, piperazinyl, indolinyl, azetidinyl, tetrahydropyranyl, tetrahydrothiopyranyl, tetrahydrofuranyl, hexahydropyrimidinyl, hexahydropyridazinyl, 1, 4,5, 6-tetrahydropyrimidin-2-ylamine, dihydro-oxazolyl, 1, 2-thiazinanyl-1, 1-dioxide, 1,2, 6- thiadiazinanyl-1, 1-dioxide, isothiazolidinyl-1, 1-dioxide and imidazolidinyl-2,4-dione.

"Mono-unsaturated heterocyclyl"refers to heterocyclyl containing one double bond or one triple bond."Poly-unsaturated heterocyclyl"refers to heterocyclyl containing at least two double bonds or two triple bonds or a combination of at least one double bond and one triple bond.

"Substituted heterocyclyl"refers to heterocyclyl groups further bearing one or more substituents.

The terms"heterocyclyl","heteroaryl"and"aryl", when associated with another moiety, unless otherwise specified, shall have the same meaning as given above. For example,"aroyl" refers to phenyl or naphthyl linked to a carbonyl group (C=O).

Each aryl or heteroaryl unless otherwise specified includes its partially or fully hydrogenated derivative. For example, quinolinyl may include decahydroquinolinyl and tetrahydroquinolinyl, naphthyl may include its hydrogenated derivatives such as tetrahydranaphthyl.

As used herein above and throughout this application,"nitrogen"or"N"and"sulfur"or"S" include any oxidized form of nitrogen and sulfur and the quaternized form of any basic nitrogen sulfoxide, sulfone, nitrone, N-oxide.

As used herein a wording defining the limits of a range of length such as e. g."from 1 to 5" means any integer from 1 to 5, i. e. 1,2, 3,4 and 5. In other words, any range defined by two integers explicitly mentioned is meant to comprise any integer defining said limits and any integer comprised in said range.

As used herein the term substituted shall mean that one or more H atom of the group or compound which is substituted, is replaced by a different atom, a group of atoms, a molecule or a molecule moiety. Such atom, group of atoms, molecule or molecule moiety is also referred to herein as substituent.

The substituent can be selected from the group comprising hydroxy, alkoxy, mercapto, cycloalkyl, heterocyclic, aryl, heteroaryl, aryloxy, halogen, trifluoromethyl, difluoromethyl, cyano, nitrone, amino, amido,-C (O) H, acyl, oxyacyl, carboxyl, carbamate, sulfonyl, sulphonamide and sulfur. Any of the substituents may be substituted itself by any of the aforementioned substituents. This applies preferably to cycloalkyl, heterocylic, aryl, heteroaryl and aryloxy. It is also preferred that alkoxy and mercapto are those of a lower alkyl group. It is to be acknowledged that any of the definition provided herein also applies to any substituent.

A substituent can also be any of Ra, Rb, RC, Rd, Re, Rf, and Rg and/or any of Rl to R2l. It is also within the present invention that any substitutent may in turn be substituted by a substituent. A group, structure, moiety or the like which is substituted may comprise several substituents which may either be different or the same.

As used herein =T can mean in any embodiment of the various aspects of the present invention that with =T is selected from electron withdrawing groups, whereby preferably the electron withdrawing groups are selected from =O, =N-Re, =N-CN, =N-N02 and =CH- NO2, and =S, It is within the present invention that any thiourea moieties and derivates therefrom, particularly those described herein, can, in principle be replaced by a cyanoguanidine moiety or residue and respective derivates therefrom as described in J. Med. Chem 1977,20, 901- 906. In Addition to being weakly basic cyanoguanidine and thiourea are also weakly acidic and both are therefore neutral and weakly amphoteric compounds. Cyanoguanidine is also similar to thiourea in its geometry since both are planar structures with almost identical C-N bond lengths and bond angles. Another property common to thioureas and cyanoguanidines is conformational isomerism resulting from restricted C-N bond rotation. Cyanoguanidine and thiourea are similar in their hydrophilicity and hydrogen-bonding properties; they have comparably low octanol-water partition coefficients (P) and are both reasonably soluble in water.

As used herein in connection with an embodiment of the various aspects of the present invention the term"wherein Rl and R2, R2 and R3, R3 and R4, Rl and R3, Rl and R4, or R2 and R4 may be linked so as to form a ring comprising 4 to 12 members, preferably 5 to 10 members"shall mean that any of the two residues R, such as, for example, Rl and R2 or R2 and R3, are linked to each through a covalent bond, a non-covalent bond or any combination thereof. The formation of the ring may be the result of one or several of this kind of bonds. It is to be understood that the molecule may comprise one or more of those rings formed by two residues R.

In a preferred embodiment wherein Rl and R2, R2 and R3, R3 and R4, Ri and R3, RI and R4, or R2 and R4 linked so as to form a ring comprising 4 to 12 members, preferably 5 to 10 members, more preferably 5 or 6 members, RI, R2, R3 and R4 are each and independently selected from the group comprising H, OR6, SR7, NR8R9, halo, alkyl, substituted alkyl, alkylaryl, substituted alkylaryl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, aryl, substituted aryl, heterocyclyl, substituted heterocyclyl, alkylheterocyclyl, substituted alkylheterocyclyl, heteroaryl, substituted heteroaryl, alkylheteroaryl and substituted alkylheteroaryl ; The ring may be cycloalkyl, heterocyclyl, aryl, or heteroaryl. The cycloalkyl or heterocyclyl ring can be mono-unsaturated or poly-unsaturated. The ring can be substituted by one or more substituents as defined herein As used herein in connection with an embodiment of the various aspects of the present invention the term"each and independently selected from a group"or"are independently from each other selected from the group"refers to two or more atoms, groups, substituents, moieties or whatsoever and describes that the single atom, group etc. mentioned can be selected from the group. The wording used is a truncation which avoids unnecessary repetition as otherwise for each of the atoms, groups etc. the same group definition would have to be repeated.

As used herein in connection with an embodiment of the various aspects of the present invention the term"each and individually absent"refers to two or more atoms, groups, substituents, moieties or whatsoever and describes that the single atom, group etc. mentioned can be absent regardless whether any of the other atoms, groups etc. mentioned is absent. The wording used is a truncation which avoids unnecessary repetition as otherwise for each of the atoms, groups etc. the fact that it may be absent in an embodiment of the invention would have to be repeated.

In connection with the present invention some groups such as, e. g.,- (CRaRb)- or- (CRfRg are repeated, i. e. are repeatedly present in a compound according to the present invention.

Typically such repetition occurs in such a manner that, e. g.,- (CRR)- is repeated one or several times. In case, e. g.,- (CRaRb- is repeated one time which means that there are two consecutive groups of- (CRaRb-, these two forms of- (CRaRb)- can be either the same or they may be different in a different embodiment which means that either Ra or Rb or both of them are different between said two- (CRaRb- groups. If there are three or more of these groups such as, e. g.,- (CRaRb-, it is possible that all of them are different or only some or different whereas others are the same in the sense defined above. Any permutation for the arrangement for such identical or different groups is within the present invention.

The same applies to the design and arrangement of the spacer-M1-L1-K-L2-M2-.

In connection with any of the compounds according to the present invention and more particularly in connection with the compounds according to formulae VI to XIII and XIX to XXVI it is to be noted that the formation of a ring structure through E between the cyclic moiety A such as the phenol moiety and the spacer X can occur between the cyclic moiety A such as the phenol moiety and any of the spacer moieties-Ml-L1-K-L2-M2-, regardless whether they are of a linear or any of the cyclic structures themselves. It is therefore within the present invention that in case of a repetition of the above described spacer moiety-M1- L1-K-L2-M2-the ring formation can either occur at the-Ml-Ll-K-L2-M2-moiety which is next or closest to the ring as represented in the respective formulae, or at the or any of the further-Ml-Ll-K-L2-M2-moieties present in the particular compound.

As used herein in connection with an embodiment of the various aspects of the present invention the term C=T shall represent a C atom having a double bond with T which represents certain atoms, groups, substituents, moieties or the like as further defined herein.

It is within the present invention that the features of the various embodiments of the present invention can be realized either alone or in combination with the features of any other embodiment (s) of the present invention. Thus any combination of an/the individual feature or the combination of features of an embodiment of the present invention with an/the individual feature (s) or the combination of features of any other embodiment (s), either alone or in combination with other embodiments, shall be disclosed by the present specification.

As used herein in connection with an embodiment of the various aspects of the present invention the term referring to a group, substituent, moiety, spacer or the like specifying that it"can be inserted in any orientation into any of the preceding formulae"means that the group etc. can be attached to another atom, group, substitutent, moiety spacer or the like of any of the compounds according to the present invention or any of the formulae disclosed herein via any of its ends an in particular through any of the atoms arranged at the ends of said group, substituent, moiety, spacer or the like.

In a further aspect the present invention is related to the use of a compound according to any of the aspects of the present invention as an inhibitor to or for a rotamase.

In an embodiment the rotamase regulates a part of the cell cycle.

In a preferred embodiment the rotamase regulates a part of the cell cycle, whereby preferably the part of the cell cycle is mitosis.

In an even more preferred embodiment the rotamase is a mammalian rotamase, preferably a human rotamase, more preferably hPinl.

In a further aspect the present invention is related to the use of the compounds according to the present invention as a pharmaceutical or in a pharmaceutical composition or for the manufacture of such pharmaceutical composition which is preferably for the prophylaxis and/or treatment of a disease, whereby the disease involves a rotamase, whereby the rotamase is a mammalian rotamase, preferably a human rotamase, more preferably hPinl.

In connection with the further aspect of the present invention related to the use of any of the aforementioned compounds according to the present invention as an inhibitor to rotamases the following will be acknowledged by the one skilled in the art. In view of the characteristics of the compounds according to the present invention to be active as an inhibitor of (a) rotamase (s), it is sufficient that the respective compound is at least suitable to inhibit at least one rotamase. The compounds according to the present invention which may be used as inhibitors, are also referred to as rotamase inhibitors herein.

Rotamases as such are known in the art and, for example, described in the introductory part of this specification which is incorporated by reference. Rotamases as used herein shall mean cyclophilins, FK-506 binding proteins and the rotamases of the Pinl/parvulin class. The Pinl/parvulin class includes Pins 1 to 3, PinL/parvulin, dodo, and Esl/Pftl. Suitable assays to determine whether a compound is suitable to inhibit a rotamase are known to the one skilled in the art and also described in the present examples. Basically, a rotamase is provided the activity of which or non-activity of which may be determined. A candidate inhibitor, i. e. a compound which is to be tested whether it is active as an inhibitor to rotamase, is added to the rotamase and tested whether upon the addition and/or influence of the candidate inhibitor the activity of the rotamase is changed relative to the activity without candidate rotamase inhibitor. If the rotamase activity is decreased by the candidate rotamase inhibitor, said candidate rotamase inhibitor is a rotamase inhibitor according to the present invention.

In another aspect of the present invention the compounds according to the present invention may be used in a method for inhibiting a rotamase. In such case a rotamase is provided and a candidate rotamase inhibitor is added thereto whereupon the activity of rotamase is decreased.

Optionally, such decrease in rotamase activity is measured. The techniques used theretofore are basically the same as outlined in connection with the use of the compounds according to the present invention as rotamase inhibitors.

The compounds according to the present invention are preferably reversible rotamase inhibitors.

By"reversible"herein is meant that the inhibitor binds non-covalently to the enzyme, and is to be distinguished from irreversible inhibition. See Walsh, Enzymatic Reaction Mechanisms, Freeman & Co. , N. Y. , 1979. "Reversible"in this context is a term understood by those skilled in the art. Preferably the rotamase inhibitors according to the present invention are competitive inhibitors, that is, they compete with substrate in binding reversibly to the enzyme, with the binding of inhibitor and substrate being mutually exclusive.

In a preferred embodiment of the compounds according to the present invention being active as a rotamase inhibitor, the dissociation constant for inhibition of a rotamase with the inhibitor, generally referred to and characterized by those in the art as Kj, is at most about 100 pM. By the term"binding constant"or"dissociation constant"or grammatical equivalents herein is meant the equilibrium dissociation constant for the reversible association of inhibitor with enzyme. The dissociation constants are defined and determined as described below. The determination of dissociation constants is known in the art. For example, for reversible inhibition reactions such as those of the present invention, the reaction scheme is as follows: kl E+I = E*I (Equation 1) k2 The enzyme (E) and the inhibitor (I) combine to give an enzyme-inhibitor complex (E*I).

This step is assumed to be rapid and reversible, with no chemical changes taking place; the enzyme and the inhibitor are held together by non-covalent forces. In this reaction, kl is the second order rate constant for the formation of the E*I reversible complex. k2 is the first order rate constant for the dissociation of the reversible E*I complex. In this reaction, Ki =k2/ki.

The measurement of the equilibrium constant Ki proceeds according to techniques well known in the art, as described in the examples. For example, assays generally use synthetic chromogenic or fluorogenic substrates. The respective Ki values may be estimated using the Dixon plot as described by Irwin Segel in Enzyme Kinetics: Behavior and analysis of rapid equilibrium and steady-state enzyme systems, 1975, Wiley-lnterscience Publication, John Wiley & Sons, New York, or for competitive binding inhibitors from the following calculation: l- (Vi/Vo) = [I]/ [+Ki (l+ ( [S]/K.))) (Equation2) wherein vo is the rate of substrate hydrolysis in the absence of inhibitor, and v ; is the rate in the presence of competitive inhibitor.

It is to be understood that dissociation constants are a particularly useful way of quantifying the efficiency of an enzyme with a particular substrate or inhibitor, and are frequently used in the art as such. If an inhibitor exhibits a very low K ; value, it is an efficient inhibitor.

Accordingly, the rotamase inhibitors of the present invention have dissociation constants, K ;, of at most about 100 uM. Preferably, the rotamase inhibitors according to the present invention exhibit dissociation constants of at most about 10 aM, more preferably about 1 uM, most preferably of at most about 100 nM.

The rotamase inhibitors of the present invention may be easily screened for their inhibitory effect. The inhibitor is first tested against different classes of rotamases for which the targeting group of the inhibitor was chosen, as outlined above. The activity of rotamases is typically measured by using a protease coupled assay with chromogenic substrates and conformer specific proteases. Basically, upon the conformer specific protease activity the chromogenic substrate is converted into a compound which has an absorption characteristic which is different from the starting chromogenic substrate and may thus be selectively measured. This reaction is accelerated in presence of the rotamase and decelerated in the presence of rotamase-inhibitors. Alternatively, many rotamases and their corresponding chromogenic substrates are commercially available. Thus, a variety of rotamases are routinely assayed with synthetic chromogenic substrates in the presence and absence of the rotamase inhibitor, to confirm the inhibitory action of the compound, using techniques well known in the art. The effective inhibitors are then subjected to kinetic analysis to calculate the Kj values, and the dissociation constants determined.

If a compound inhibits at least one rotamase, it is a rotamase inhibitor for the purposes of the present invention. Preferred embodiments of the rotamase inhibitors according to the present invention are compounds and inhibitors, respectively, that exhibit the correct kinetic parameters Ki below 100, uM against the targeted rotamases.

In a further aspect of the present invention any of the compounds used as rotamase inhibitors or as a medicament may be labelled.

By a"labelled rotamase inhibitor"herein is meant a rotamase inhibitor that has at least one element, isotope or chemical compound attached to enable the detection of the rotamase . inhibitor or the rotamase inhibitor bound to a rotamase. In general, labels as used herein, fall into three classes: a) isotopic labels, which may be radioactive or heavy isotopes; b) immune labels, which may be antibodies or antigens ; and c) colored or fluorescent dyes. The labels may be incorporated into the rotamase inhibitor at any position. Examples of useful labels include 14C, 13C, 15N, 3H, biotin, and fluorescent labels as are well known in the art.

In a further aspect the compounds according to the present invention, particularly those having rotamase inhibitory activity, may be used for removing, identifying and/or inhibiting contaminating rotamases in a sample.

Therefore, the rotamase inhibitors of the present invention are, for example, added to a sample where the catalytic activity by contaminating rotamases is undesirable. Alternatively, the rotamase inhibitors of the present invention may be bound to a chromatographic support, using techniques well known in the art, to form an affinity chromatography column. A sample containing an undesirable rotamase is run through the column to remove the rotamase.

Alternatively, the same methods may be used to identify new rotamases. In doing so, a new rotamase contained in a sample may bind to the rotamase inhibitor bound to the chromatographic support and upon elution, preferably a specific elution, from said chromatographic support, characterized and compared to other rotamase activities with regard to, among others, specificities. The characterization of the rotamase as such is known to the one skilled in the art.

In a further aspect the present invention is related to a pharmaceutical composition comprising a compound according to any of the aspects of the present invention and a pharmaceutically acceptable carrier, diluent or excipient.

In an embodiment the composition comprises a further pharmaceutically active compound, preferably such further pharmaceutically active compound is a chemotherapeutic agent.

In a preferred embodiment of the composition the compound is present as a pharmaceutically acceptable salt or a pharmaceutically active solvate.

In an even more preferred embodiment the pharmaceutically active compound is either alone or in combination with any of the ingredients of the composition present in a multitude of individualized dosages and/or administration forms.

The use of the compounds according to the present invention for the manufacture of a medicament is based on the fact that the compounds according to the present invention are inhibitors of rotamases and rotamases in turn have been identified in both procaryotic and eucaryotic cells such as in bacteria, fungi, insect and mammalian cells. In this cellular environment rotamases are known to have an impact on cell proliferation and mitosis, respectively. Because of this, rotamase inhibitors may be used for the treatment of a wide variety of disorders involving cell cycle regulation, both procaryotic and eucaryotic cell cycle regulation. The term"treatment"as used herein comprises both treatment and prevention of a disease. It also comprises follow-up treatment of a disease. Follow-up treatment is realized upon a treatment of a disease using compounds preferably different from the one according to the present invention. For example, after stimulating the growth of a cell, tissue or the like by the application of a respective compound such as, e. g., erythropoietin, it might be necessary to stop an overshooting reaction of cell proliferation which may be obtained using the compounds according to the present invention.

In a further aspect the present invention is related to the use of the compounds according to the present invention as a medicament and for the manufacture of a medicament, respectively.

It is to be understood that any of the compounds according to the present invention can be used for the treatment of or for the manufacture of a medicament for the treatment of any of the diseases disclosed herein, irrespective of the mode of action or the causative agent involved as may be specified herein. Of Course, it may particularly be used for any form of such disease where the particular causative agent is involved. Causative agent as used herein also means any agent which is observed in connection with the particular disease described and such agent is not necessarily causative in the sense that is causes the observed diseases or diseased condition.

In an embodiment the medicament is for the treatment or prevention of a disease, whereby the disease involves an undesired cell proliferation.

This use of the compounds according to the present invention is based on the fact that the compounds according to the present invention are suitable to inhibit undesired cell proliferation. Undesired cell proliferation comprises the undesired cell proliferation of procaryotic cells as well as undesired cell proliferation of eucaryotic cells. The term undesired cell proliferation also covers the phenomenon of abnormal cell proliferation, abnormal mitosis and undesired mitosis. Abnormal cell proliferation means any form of cell proliferation which occurs in a manner different from the normal cell proliferation. Normal cell proliferation is a cell proliferation observed under normal circumstances by the majority of cells and organisms, respectively. The same basic definition applies to abnormal mitosis.

More particularly, undesired cell proliferation and undesired mitosis mean a proliferation and a mitosis, respectively, which may be either a normal or an abnormal cell proliferation, however, in any case it is not a cell proliferation or mitosis which is desired. Desired may thus be defined by an individual such as a human being and in particular a physician, and defined within certain boundaries whereby the boundaries as such may reflect the extent of proliferation and mitosis, respectively, observed under usual conditions or in the majority of cells and organisms, respectively, or may be arbitrarily fixed or defined. Cell proliferation as used herein refers preferably to the proliferation of cells forming the organism to be treated or to which a compound according to the present invention shall be administered which is also referred to herein as the first organism. Cell proliferation as used herein also means the proliferation of cells which are different from the cells forming a first organism or species but are the cells forming a second organism or second species. Typically, the second organism enters in or has a relationship with the first organism. Preferably, the first organism is a human being or an animal or plant, also referred to herein as patient, and the second organism is a parasite and pathogen, respectively, to said first organism. Mitosis as used herein, preferably means the cell division of cells being subject to said cell proliferation whereby even more preferably mitosis is the process of cell division whereby a complete set of chromosomes is distributed to the daughter cells.

Without wishing to be bound by any theory, it seems that the compounds according to the present invention act on cells and thus influence their proliferation and mitosis, respectively, by being inhibitors to some enzymatic activity. Preferably, the inhibition is reversible. This activity is shown by the compounds according to the present invention with regard to bacteria, fungi, insect and mammalian cells.

Because of this, the compounds according to the present invention may be used for the treatment of a wide variety of disorders involving cell cycle regulation, both procaryotic and eucaryotic cell cycle regulation. The term"treatment"as used herein comprises both treatment and prevention of a disease. It also comprises follow-up treatment of a disease.

Follow-up treatment is realized upon a treatment of a disease using compounds preferably different from the one according to the present invention. For example, after stimulating the growth of a cell, tissue or the like by the application of a respective compound such as, e. g., erythropoietin, it might be necessary to stop an overshooting reaction of cell proliferation which may be obtained using the compounds according to the present invention.

By"reversible"herein is meant that the inhibitor binds non-covalently to the respective enzyme, and is to be distinguished from irreversible inhibition. See Walsh, Enzymatic Reaction Mechanisms, Freeman & Co. , N. Y., 1979. "Reversible"in this context is a term understood by those skilled in the art. Preferably the compounds according to the present invention are competitive inhibitors, that is, they compete with substrate in binding reversibly to the enzyme, with the binding of inhibitor and substrate being mutually exclusive.

In a preferred embodiment of the compounds according to the present invention the dissociation constant for inhibition of the enzyme (s) with the inhibitor, i. e. the compound according to the present invention, generally referred to and characterized by those in the art as Ki, is at most about 100 u. M. By the term"binding constant"or"dissociation constant"or grammatical equivalents herein is meant the equilibrium dissociation constant for the reversible association of inhibitor with enzyme. The dissociation constants are defined and determined as described below. The determination of dissociation constants is known in the art. For example, for reversible inhibition reactions such as those of the present invention, the reaction scheme is as follows: ksi Ei E*I (Equation 1) k2 The enzyme (E) and the inhibitor (I) combine to give an enzyme-inhibitor complex (E*I).

This step is assumed to be rapid and reversible, with no chemical changes taking place; the enzyme and the inhibitor are held together by non-covalent forces. In this reaction, kl is the second order rate constant for the formation of the E*I reversible complex. ka is the first order rate constant for the dissociation of the reversible E*I complex. In this reaction, Ki =k2/ki.

The measurement of the equilibrium constant K ; proceeds according to techniques well known in the art. For example, assays generally use synthetic chromogenic or fluorogenic substrates. The respective K ; values may be estimated using the Dixon plot as described by Irwin Segel in Enzyme Kinetics: Behavior and analysis of rapid equilibrium and steady-state enzyme systems, 1975, Wiley-lnterscience Publication, John Wiley & Sons, New York, or for competitive binding inhibitors from the following calculation: l- (Vi/Vo) = [Il/[I] +K ; (l+ ([S]/Km))) (Equation 2) wherein Vo is the rate of substrate hydrolysis in the absence of inhibitor, and v ; is the rate in the presence of competitive inhibitor.

The compounds according to the present invention may be easily screened for their efficacy in relation to the various uses disclosed herein By a"labelled compound according to the present invention"herein is meant a compound according to the present invention that has at least one element, isotope or chemical compound attached to enable the detection of the compound or the compound bound to a target such as an enzyme. In general, labels as used herein, fall into three classes: a) isotopic labels, which may be radioactive or heavy isotopes; b) immune labels, which may be antibodies or antigens; and c) colored or fluorescent dyes. The labels may be incorporated into the compound at any position. Examples of useful labels include 14C, 13C, lsN, 3H, biotin, and fluorescent labels as are well known in the art.

As used herein, the term"disease"describes any disease, diseased condition or pathological condition. Such disease may also be defined as abnormal condition. Also, in case of a . pathogen, disease means a condition where a pathogen or an unwanted organism is present or present in a concentration or compartment where it is undesired and thus subject to reduction in numbers, removal, elimination and/or destruction by using the compounds according to the present invention.

The compounds according to the present invention may be used as a medicament and for the manufacture of a medicament, respectively, whereby the medicament is for the treatment of cell proliferative disorders and any of the diseases specified herein. Cell proliferated disorders as used herein, typically involve an abnormal cell proliferation, an undesired cell proliferation, an abnormal mitosis and/or an undesired mitosis.

Cell proliferative disorders contemplated for treatment using the compounds according to the present invention and for the methods disclosed herein include also disorders characterized by unwanted or undesired, inappropriate or uncontrolled cell growth. Preferably, the disease is selected from the group comprising neurodegenerative diseases, stroke, inflammatory diseases, immune based disorders, infectious diseases, heart diseases, fibrotic disorders, cardiovascular diseases and cell proliferative diseases. Rotamases comprise families of ubiquitous and highly conserved enzymes who have been reported to play important roles in biological processes like protein folding, proteolysis, protein dephosphorylation, peptide transport function, cell cycle regulation, protein synthesis. Furthermore various isomerases have been shown to have regulatory functions as stable or dynamic part of heterooligomeric complexes containing physiologically relevant proteins e. g. hormone receptors, ion channels, kinases, and growth factor receptors.

Preferably, the neurodegenerative disease is selected from the group comprising Alzheimer's disease, Huntington's disease, Parkinson's disease, peripheral neuropathy, progressive supranuclear palsy, corticobasal degeneration, frontotemporal dementia, synucleinopathies, multiple system atrophy, amyotrophic lateral atrophy, prion diseases and motor neuron diseases.

The compounds according to the present invention are additionally useful in inhibiting cell cycle (mitosis) or cell division in pathogenic organisms and are, therefore, useful for treating infectious diseases.

In a preferred embodiment the infectious is selected from the group comprising fungal, viral, bacterial and parasite infection.

Fungal infections contemplated for treatment using the compounds and methods according to the present invention include systemic fungal infections, dermatophytoses and fungal infections of the genito-urinary tract. Fungal infections, preferably systemic fungal infections, include those caused by Histoplasma, Coccidioides, Cryptococcus, Blastomyces, Paracoccidioides, Aspergillus, Nocardia, Sporothrix, Rhizopus, Absidia, Mucor, Hormodendrum, Phialophora, Rhinosporidium, and the like. Dermatophyte infections include those caused by Microsporum, Trichophyton, Epidermophyton, Candida, Pityrosporum, and the like. Fungal disorders of the genito-urinary tract include infections caused by Candida, Cryptococcus, Aspergillus, Zygomycodoides, and the like. Infection by such organisms causes a wide variety of disorders such as ringworm, thrush or candidiasis, San Joaquin fever or Valley fever or coccidiodomycosis, Gilchrist's disease or blastomycosis, aspergillosis, cryptococcosis, histioplasmosis, paracoccidiomycosis, zygomycosis, mycotic keratitis, nail hair and skin disease, Lobo's disease, lobomycosis, chromoblastomycosis, mycetoma, and the like. These infections can be particularly serious, and even fatal, in patients with a depressed immune system such as organ transplant recipients and persons with acquired immunodefficiency syndrome (AIDS). Insofar a patient group which can be treated using the inhibitors according to the present invention are persons with AIDS, particularly those suffering from any of the infectious diseases described herein.

In a further embodiment the bacterial infection is selected from the group comprising infections caused by both Gram-positive and Gram-negative bacteria, including infections caused by Staphylococcus, Clostridium, Streptococcus, Enterococcus, Diplococcus, Hemophilus, Neisseria, Erysipelothricosis, Listeria, Bacillus, Salmonella, Shigella, Escherichia, Klebsiella, Enterobacter, Serratia, Proteus, Morganella, Providencia, Yersinia, Canaphylobacter, Mycobacteria, Helicobacter, Legionalla, Nocardia and the like.

In a preferred embodiment the bacterial infection causes a wide variety of diseases. Said disorders are selected, among others, from the group comprising pneumonia, diarrhea, dysentery, anthrax, rheumatic fever, toxic shock syndrome, mastoiditis, meningitis, gonorrhea, typhoid fever, brucellis, Lyme disease, gastroenteritis, tuberculosis, cholera, tetanus and bubonic plague.

In another embodiment the disease is a viral infection, more particularly a viral infection caused by a virus selected from the group comprising retrovirus, HIV, Papilloma virus, Polio virus, Epstein-Barr, Herpes virus, Hepatitis virus, Papova virus, Influenza virus, Rabies, JC, encephalitis causing virus, hemorrhagic fever causing virus such as Ebola Virus and Marburg Virus.

In a further embodiment the parasite infection is selected from the group comprising infections caused by Trypanosoma, Leishmania, Trichinella, Echinococcus, Nematodes, <BR> <BR> <BR> <BR> Classes Cestoda, Trematoda, Monogenea, Toxoplasma, Giardia, Balantidium, Paramecium, Plasmodium or Entamoeba.

The disease may further be a cell proliferative disorder which preferably is selected from the group characterized by unwanted, inappropriate or uncontrolled cell growth. Particular examples include cancer, fibrotic disorders, non-neoplastic growths. The neoplastic cell proliferative disorder is preferably selected from the group comprising solid tumors, and hematopoeitic cancers such as lymphom and leukemia.

More preferably, the solid tumor is selected from the group comprising carcinoma, sarcoma, osteoma, fibrosarcoma, and chondrosarcoma.

More preferably, the cell proliferative disorder is selected from the group comprising breast cancer, prostate cancer, colon cancer, brain cancer, lung cancer, pancreatic cancer, gastric cancer, bladder cancer, kidney cancer and head and neck cancer. Preferably, the lung cancer is non-small lung cancer and small lung cancer.

In case the disease is a non-neoplastic cell proliferative disorder, it is preferably selected from the group comprising fibrotic disorder. Preferably, the fibrotic disorder is fibrosis.

The disease may also be a non-neoplastic cell proliferative disorder which is selected from the group comprising prostatic hypertrophy, preferably benign prostatic hypertrophy, endometriosis, psoriasis, tissue repair and wound healing. Fibrotic disorders which may be treated using the compounds according to the present invention are generally characterized by inappropriate overproliferation of non-cancerous fibroblasts. Examples thereof include fibromyalgia, fibrosis, more particularly cystic, hepatic, idopathic pulmonary, and pericardial fibrosis and the like, cardiac fibromas, fibromuscular hyperplasia, restenosis, atherosclerosis, fibromyositis, and the like.

In another embodiment the immune based and/or inflammatory disease is an autoimmune disease or autoimmune disorder. In a further embodiment, the immune based and/or inflammatory disease is selected from the group comprising rheumatoid arthritis, glomerulonephritis, systemic lupus erythematosus associated glomerulonephritis, irritable bowel syndrome, bronchial asthma, multiple sclerosis, pemphigus, pemphigoid, scleroderma, myasthenia gravis, autoimmune haemolytic and thrombocytopenic states, Goodpasture's syndrome, pulmonary hemorrhage, vasculitis, Crohn's disease, and dermatomyositis.

In a further preferred embodiment the immune based and/or inflammatory disease is an inflammatory condition.

In a still further embodiment the immune based and/or inflammatory disease is selected from the group comprising inflammation associated with burns, lung injury, myocardial infarction, coronary thrombosis, vascular occlusion, post-surgical vascular reocclusion, artherosclerosis, traumatic central nervous system injury, ischemic heart disease and ischemia-reperfusion injury, acute respiratory distress syndrome, systemic inflammatory response syndrome, multiple organ dysfunction syndrome, tissue graft rejection and hyperacute rejection of transplanted organs.

It is also within the present invention that the compounds according to the present invention may be used for the treatment of a patient suffering from a disease or diseased condition as defined above. Such treatment comprises the administration of one or several of the compounds according to the present invention or a medicament or pharmaceutical composition described herein.

Toxicity and therapeutic efficacy of a compound can be determined by standard pharmaceutical procedures in cell culture or experimental animals. Cell culture assays and animal studies can be used to determine the LDso (the dose lethal to 50% of a population) and the EDso (the dose therapeutically effective in 50% of a population). The dose ratio between toxic and therapeutic effects is the therapeutic index, which can be expressed as the ratio LD5o/ED5o. Compounds which exhibit large therapeutic indices are preferred. The data obtained from these cell culture assays and animal studies can be used in formulating a range of dosages suitable for use in humans. The dosage may vary within this range depending upon a variety of factors, e. g. , the dosage form employed, the route of administration utilized, the condition of the subject, and the like For any compound according to the present invention, the therapeutically effective dose can be estimated initially from cell culture assays by determining an ICSO (i. e. , the concentration of the test substance which achieves a half-maximal inhibition of cell proliferation). A dose can then be formulated in animal models to achieve a circulating plasma concentration range that includes the ICSO as determined in cell culture. Such information can be used to more accurately determine useful doses in humans. Levels in plasma may be measured, for example by HPLC or LC/MS.

It should be noted that the attending physician would know how to and when to terminate, interrupt, or adjust administration due to toxicity, to organ dysfunction, and the like. Conversely, the attending physician would also know to adjust treatment to higher levels if the clinical response were not adequate (precluding toxicity). The magnitude of an administered dose in the management of the disorder of interest will vary with the severity of the condition to be treated, with the route of administration, and the like. The severity of the condition may, for example, be evaluated, in part, by standard prognostic evaluation methods.

Further, the dose and perhaps dose frequency will also vary according to the age, body weight, and response of the individual patient. Typically, the dose will be between about 1-10 mg/kg of body weight. About 1 mg to about 50 mg will preferably be administered to a child, and between 25 mg and about 1000 mg will preferably be administered to an adult.

A program comparable to that discussed above may be used in veterinary medicine. The exact dose will depend on the disorder to be treated and will be ascertainable by one skilled in the art using known techniques.

Depending on the specific conditions to be treated, such compounds may be formulated and administrated systemically or locally. Techniques for formulation and administration may be found in"Remington's Pharmaceutical Sciences", 1990, 18th ed., Mack Publishing Co., Easton, PA. The administration of a compound according to the present invention can be done in a variety of ways, including, but not limited to, orally, subcutaneously, intravenously, intranasally, transdermally, intraperitoneally, intramuscularly, intrapulmonary, vaginally, rectally, or intraocularly, just to name a few. In some instances, for example, in the treatment of wounds and inflammation, the compound according to the present invention may be directly applied as a solution or spray.

In a further aspect the present invention is related to a medicament or a pharmaceutical composition comprising at least one active compound and at least one pharmaceutically acceptable carrier, excipient or diluent. As used herein, the active compound is a compound according to the present invention, a pharmaceutically salt or base thereof or a prodrug thereof, if not indicated to the contrary.

For injection, compounds of the invention may be formulated in aqueous solution, preferably in physiologically compatible buffers such as Hank's solution, Ringer's solution, or physiologically saline buffer. For transmucosal administration, penetrants appropriate to the barrier to be permeated are used in the formulation. Such penetrants are generally known in the art.

The use of pharmaceutical acceptable carriers to formulate the compounds according to the present invention into dosages or pharmaceutical compositions suitable for systemic administration is within the scope of the present invention. With proper choice of carrier and suitable manufacturing practice, the compositions of the present invention, in particular those formulated as solutions, may be administered parenterally, such as by intravenous injection.

The compounds can be readily formulated using pharmaceutically acceptable carriers well known in the art into dosages suitable for oral administration. Such carriers enable the compounds according to the present invention to be formulated as tablets, pills, capsules, dragees, liquids, gels, syrups, slurries, suspensions and the like, for oral ingestion by a subject to be treated.

Compounds according to the present invention or medicaments comprising them, intended to be administered intracellularly may be administered using techniques well known to those of ordinary skill in the art. For example, such agents may be encapsulated into liposomes, then administered as described above. Liposomes are spherical lipid bilayers with aqueous interiors. All molecules present in an aqueous solution at the time of liposome formation are incorporated into the aqueous interior. The liposomal contents are both protected from the external microenvironment and, because liposomes fuse with cell membranes, are efficiently delivered into the cell cytoplasm. Delivery systems involving liposomes are disclosed in International Patent Publication No. WO 91/19501, as well as U. S. Patent No. 4, 880, 635 to Janoff et al. The publications and patents provide useful descriptions of techniques for liposome drug delivery and are incorporated by reference herein in their entirety.

Pharmaceutical compositions comprising a compound according to the present invention for parenteral administration include aqueous solutions of the active compound (s) in water- soluble form. Additionally, suspensions of the active compounds may be prepared as appropriate oily injection suspensions. Suitable lipophilic solvents or vehicles include fatty oils such as sesame oil or castor oil, or synthetic fatty acid esters, such as ethyl oleate or triglycerides, or liposomes. Aqueous injections suspensions may contain compounds which increase the viscosity of the suspension, such as sodium carboxymethyl cellulose, sorbitol, dextran, or the like. Optionally, the suspension may also contain suitable stabilizers or agents which increase the solubility of the compounds to allow for the preparation of highly concentrated solutions.

Pharmaceutical compositions comprising a compound according to the present invention for oral use can be obtained by combining the active compound (s) with solid excipient, optionally grinding the resulting mixture, and processing the mixture of granules, after adding suitable auxiliaries, if desired, to obtain tablets or dragee cores.

Suitable excipients are, in particular, fillers such as sugars, including lactose, sucrose, mannitol, sorbitol, and the like; cellulose preparations, such as, for example, maize starch wheat starch, rice starch, potato starch, gelatin, gum tragacanth, methyl cellulose, hydroxypropylmethyl cellulose, sodium carboxymethyl cellulose, polyvinylpyrrolidone (PVP) and the like, as well as mixtures of any two or more thereof. If desired, disintegrating agents may be added, such as cross-linked polyvinyl pyrrolidone, agar, alginic acid or a salt thereof such as sodium alginate, and the like.

Dragee cores as a pharmaceutical composition comprising a compound according to the present invention are provided with suitable coatings. For this purpose, concentrated sugar solutions may be used, which may optionally contain gum arabic, talc, polyvinyl pyrrolidone, carbopol gel, polyethylene glycol, titanium dioxide, lacquer solutions, suitable organic solvents or solvent mixtures, and the like. Dyestuffs or pigments may be added to the tablets or dragee coatings for identification or to characterize different combinations of active compound doses.

Pharmaceutical preparations comprising a compound according to the present invention which can be used orally include push-fit capsules made of gelatin, as well as soft, sealed capsules made of gelatin and a plasticizer, such as glycerol or sorbitol. The push-fit capsules can contain the active ingredients in admixture with filler such as lactose, binders such as starches and/or lubricants such as talc or magnesium stearate and, optionally, stabilizers. In soft capsules, the active compounds may be dissolved or suspended in suitable liquids, such as fatty oils, liquid paraffin, or liquid polyethylene glycols. In addition, stabilizers may be added.

A"patient"for the purposes of the present invention, i. e. to whom a compound according to the present invention or a pharmaceutical composition according to the present invention is administered, includes both humans and other animals and organisms. Thus the compounds, pharmaceutical compositions and methods are applicable to or in connection with both human therapy and veterinary applications including diagnostic (s), diagnostic procedures and methods as well as staging procedures and methods. For example, the veterinary applications include, but are not limited to, canine, bovine, feline, porcine, caprine, equine, and ovine animals, as well as other domesticated animals including reptiles, such as iguanas, turtles and snakes, birds such as finches and members of the parrot family, lagomorphs such as rabbits, rodents such as rats, mice, guinea pigs and hamsters, amphibians, fish, and arthropods.

Valuable non-domesticated animals, such as zoo animals, may also be treated. In the preferred embodiment the patient is a mammal, and in the most preferred embodiment the patient is human.

The pharmaceutical composition according to the present invention comprises at least one compound according to the present invention in a form suitable for administration to a patient.

Preferably, a compound according to the present application is in a water soluble form, such as being present as a pharmaceutically acceptable salt, which is meant to include both acid and base addition salts which are also generally referred to herein as pharmaceutically acceptable salts. "Acid addition salt", and more particularly"pharmaceutically acceptable acid addition salts"refers to those salts that retain the biological effectiveness of the free bases and that are not biologically or otherwise undesirable, formed with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid and the like, and organic acids such as acetic acid, propionic acid, glycolic acid, pyruvic acid, oxalic acid, maleic acid, malonic acid, succinic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, salicylic acid and the like. "Base addition salts"and more particularly"pharmaceutically acceptable base addition salts"include those derived from inorganic bases such as sodium, potassium, lithium, ammonium, calcium, magnesium, iron, zinc, copper, manganese, aluminum salts and the like. Particularly preferred are the ammonium, potassium, sodium, calcium, and magnesium salts. Salts derived from pharmaceutically acceptable organic non- toxic bases include salts of primary, secondary, and tertiary amines, substituted amines including naturally occurring substituted amines, cyclic amines and basic ion exchange resins, such as isopropylamine, trimethylamine, diethylamine, triethylamine, tripropylamine, and ethanolamine. The pharmaceutical compositions according to the present invention may also include one or more of the following: carrier proteins such as serum albumin; buffers ; fillers such as microcrystalline cellulose, lactose, corn and other starches; binding agents; sweeteners and other flavoring agents ; coloring agents; and polyethylene glycol. Additives are well known in the art, and are used in a variety of formulations.

The compounds according to the present invention are, in a further embodiment, administered to a subject either alone or in a pharmaceutical composition where the compound (s) is mixed with suitable carriers or excipient (s). In treating a subject, a therapeutically effective dose of compound (i. e. active ingredient) is administered. A therapeutically effective dose refers to that amount of the active ingredient that produces amelioration of symptoms or a prolongation of survival of a subject which can be determined by the one skilled in the art doing routine testing.

On the other hand, the compounds according to the present invention may as such or contained in a pharmaceutical composition according to the present invention be used in drug potential applications.

For example, therapeutic agents such as antibiotics or antitumor drugs can be inactivated through the catalytic action of endogenous enzymes, thus rendering the administered drug less effective or inactive. Accordingly, the compound (s) according to the present invention may be administered to a patient in conjunction with a therapeutic agent in order to potentiate or increase the activity of the drug. This co-administration may be by simultaneous administration, such as a mixture of the compound (s) according to the present invention and the drug, or by separate simultaneous or sequential administration.

According to the present invention the compounds disclosed herein, referred to as compounds according to the present invention, may be used as a medicament or for the manufacture of medicament or in a method of treatment of a patient in need thereof. Insofar any of these compounds constitute a pharmaceutical compound. The use of this kind of compound also comprises the use of pharmaceutically acceptable derivatives of such compounds.

In addition, the compounds according to the present invention may be transformed upon application to an organism such as a patient, into the pharmaceutically active compound.

Insofar the compounds according to the present invention may be prodrugs which, however, are nevertheless used for the manufacture of the medicaments as disclosed herein given the fact that at least in the organism they are changed in a form which allows the desired.

It is to be understood that any of the pharmaceutical compositions according to the present invention may be used for any of the diseases described herein.

The pharmaceutical compositions according to the present invention may be manufactured in a manner that is known as such, e. g. , by means of conventional mixing, dissolving, granulating, dragee-mixing, levigating, emulsifying, encapsulating, entrapping, lyophilizing, processes, or the like.

In a further aspect of the present invention the compounds of the present invention may be used as insecticides as they may prevent cell cycle mitosis in insect cells and thus can be used to control the growth and proliferation of a variety of insect pests. This aspect of the present invention has important applications in agriculture, such as in the field, in the storage of agricultural products and the like. Additionally, the compounds according to the present invention are useful for controlling insect populations, preferably in places inhabited by men, such as homes, offices and the like.

Any of the compounds according to the present invention containing one or more asymmetric carbon atoms may occur as racemates and racemic mixtures, single enantiomers, diastereomeric mixtures and individual diastereomers. All such isomeric forms of these compounds are expressly included in the present invention. Each stereogenic carbon may be in the R or S configuration, or a combination of configurations.

It shall be understood by the one of ordinary skill in the art that all compounds of the invention are preferably those which are chemically stable. This applies to any of the various uses of the compounds according to the present invention disclosed herein.

In determining the suitability of any of the compounds according to the present applications for the various uses, besides the particular use-specific profile to be met by such a compound, also it has to be checked whether it is stable to proteolytic degradation. The resistance of the compound used as a pharmaceutical may be tested against a variety of non-commercially available proteases in vitro to determine its proteolytic stability. Promising candidates may then be routinely screened in animal models, for example using labelled inhibitors, to determine the in vivo stability and efficacy. In any of the aforementioned uses the compound may be present in a crude or purified form. Methods for purifying the compounds according to the present invention are known to the one skilled in the art. The problem underlying the present invention is also solved by the technical teaching according to the attached independent claims. Preferred embodiments thereof may be taken from the dependent claims.

The invention is now further illustrated by reference to the following figures and examples from which further advantages, features and embodiments may be taken. It is understood that these examples are given for purpose of illustration only and not for purpose of limitation. All references cited herein are incorporated by reference.

Fig. 1 shows FACS results of compound 703, Fig. 2 show a FACS analysis of the effect of various compounds on HL 60 cells as a measure for the apoptotic activity of the compounds; and Fig. 3 shows fluorescence microscope photographs of DAPI stained HeLa cells after treatment with various compounds Example 1: Material and Methods In order that the invention herein described may be more fully understood, the following detailed description is set forth. As used herein, the following abbreviations are used: Ar is argon; D is doublet; DCM is dichloromethane; DIPEA is N, N-diisopropylethylamine ; DMF is N, N dimethylformamide ; DMSO is N, N-dimethylsulfoxide ; eq is equivalent; Et3N is triethylamine; HC1 is chlorhydric acid; HPLC is high performance liquid chromatography; h is hour; Hz is hertz; m is multiplet; mL is milliliter; NaHCO3 is sodium hydrogencarbonate ; s is singulet; THF is tetrahydrofuran.

Method A: Urea formation in solution Amine salt and DIPEA (1 eq each) or amine (1 eq) was dissolved in dry dioxan and a solution of the isocyanate (1 eq) in DCM or DMSO was added under Ar in one portion. The solution was stirred for 3 h at room temperature. The solution was diluted with 2 ml DCM and scavenger resins (tris- (2-aminoethyl)-amine polystyrene (3 eq), methylisocyanate polystyrene (3 eq) and N- (2-mercaptoethyl) aminomethyl polystyrene (3 eq)) were added to remove unreacted isocyanate, amine and electrophilic impurities respectively. After 18 h at 40°C, the solution was filtered off and the solvent was removed under reduced pressure. The obtained crude ureas were purified by HPLC.

Method B: Coupling of substituted anilines with sulfonyl chlorides Aniline (30 mg) and NEt3 (1.2 eq, 2.2 eq. when HC1 salt) were dissolved in dry acetonitrile (0.5 mL). Sulfonyl chloride (1 eq) was dissolved in dry acetonitrile (0.5 mL) and added to the solution. The reaction mixture was stirred under argon for 12 h at 40°C. Tris- (2-aminoethyl)- amine polystyrene (30 mg), (polystyrylmethyl) trimethylammonium bicarbonate (30 mg), N (2-mercaptoethyl) amino methyl polystyrene (30 mg), and methylisocyanate polystyrene (30 mg) were given to the solution and stirred for additional 12 h at 40°C. After filtration the solvent was removed under reduced pressure. The crude reaction product was purified by preparative HPLC using acetonitrile and water as mobile phase.

Method C: Coupling of substituted anilines with acid chlorides Aniline (30 mg) and NEt3 (1 eq, 2 eq. when HC1 salt) were dissolved at 0°C in dry DCM (0.5 mL) with 10% DMSO. Acid chloride (1 eq) was dissolved at 0°C in dry DCM (0.5 mL) and added to the solution. The reaction mixture was stirred under argon for 2 h while slowly warming up to room temperature. Work up was performed by pouring the reaction mixture with DCM over incubated HYDROMATRIX layers. 2 mL basic layer (saturated NaHCO3 solution 2 ml/g HYDROMATRIX), 2 mL acidic layer (2M HCl 2 ml/g HYDROMATRIX), and 2 mL of dry HYDROMATRIX layer in a 10 ml syringe were used. The solvent was removed under reduced pressure. The crude reaction product was purified by preparative HPLC using acetonitrile and water as mobile phase.

Method D: Reductive amination of aldehydes with hydroxyl anilines Amine hydrochloride (0.11 mmol, 1 eq), aldehyde (0.11 mmol, 1 eq), and DIPEA (0.11 mmol, 1 eq) were dissolved in anhydrous THF (1 mL), and molecular sieves 4A (10 mg) was added to the solution. After shaking for 1.5 h at room temperature, (polystyrylmethyl) trimethylammonium cyanoborohydride (4.3 mmol/g, 0.22 mmol) was added to the reaction mixture. After shaking for 8 h at room temperature, 4- benzyloxybenzaldehyde polystyrene (3 mmol/g, 0.22 mmol), 3- (4- (hydrazinosufonyl) phenyl) propionyl AM resin (1.5 mmol/g, 0.22 mmol), and N- (2- mercaptoethyl) aminomethyl polystyrene (2.1 mmol/g, 0.22 mmol) were added, after which the reaction mixture was shaken at room temperature for 18 h. Filtration, washing with DCM, and evaporation of the solvent in vacuo afforded the crude product, which was purified by reversed phase HPLC.

Method E: Condensation of amines with hydroxyl carboxylic acids l-Ethyl-3 (3'-dimethylaminophropyl) carbodiimide hydrochloride (0.15 mmol, 1.36 eq), hydroxyl carboxylic acid (0.15 mmol, 1.36 eq), and 1-hydroxy-7-azabenzotriazole (0.15 mmol, 1.36 eq) were dissolved in DMF (0.7 mL). After shaking for 30 min at room temperature, a solution of amine (0.11 mmol) in DMF (0.7 mL) was added to the reaction mixture. After shaking for 2 h at room temperature, amine (0.22 mmol) was added, after which the reaction mixture was shaken at 60 °C overnight. Then the solvent was evaporated in vacuo, and the residue was dissolved in DCM (7 mL). HYDROMATRIX (0.3 g) which was previously treated with HCl (2N, 0.6 mL) was added to the solution, and the mixture was shaken for 30 min. Filtration, washing with DCM, and evaporation of the solvent in vacuo afforded the crude product, which was purified by reversed phase HPLC.

Method F: Carbamate formation in solution Amine or amine salt (1 eq) and sodium bicarbonate (1 or 2 eq) were dissolved in a mixture of MeOH/H20 (3: 1). The mixture was treated with chloroformate (1 eq), which was added in three portions over 10 minutes. After 30 minutes at room temperature, the precipitating product was collected by filtration and washed with water. The obtained crude carbamate were purified by HPLC.

Method G: Carbamate formation in solution To an ice cooled mixture of amine or amine salt (1 eq) and DIPEA (1.1 eq or 2.2 eq) in dry DCM was added an ice cooled solution of chloroformate (1.1 eq) in DCM in one portion.

After 1. 5-8 h at room temperature the solvent was removed under reduced pressure. The obtained crude carbamates were purified by HPLC.

Method H: Carbamate formation in solution To a mixture of amine or amine salt (1 eq) and sodium bicarbonate (1 or 2.5 eq) in dry DCM was added chloroformate (1 eq) in one portion. After 4 hours at room temperature the sodium bicarbonate was filtered off and the solvent was removed under reduced pressure. The obtained crude carbamate were purified by HPLC.

Method I : Thiourea formation in solution Amine salt and DIPEA (1 eq each) or amine (1 eq) was dissolved in dry dioxan and a solution of the thioisocyanate (1 eq) in DCM or DMSO was added under Ar in one portion. The solution was stirred for 3 h at room temperature. The solution was diluted with 2 ml DCM and scavenger resins (tris- (2-aminoethyl)-amine polystyrene (3 eq), methylisocyanate polystyrene (3 eq) and N- (2-mercaptoethyl) aminomethyl polystyrene (3 eq) ) were added to remove unreacted isocyanate, amine and electrophilic impurities respectively. After 18 h at 40°C, the solution was filtered off and the solvent was removed under reduced pressure. The obtained crude thioureas were purified by HPLC.

Method J: Synthesis of (3-amino-5-chloro-4-hydroxy-phenyl)-ureas.

Isocyanate (5.0 mmol) was added to a stirred solution of 4-Amino-2-chloro-phenol (5.0 mmol) in anhydrous CH2Cl2 (23 mL) and THF (4 mL) at room temperature. After stirring for 12 h, the solvent was evaporated in vacuo. The residue was then dissolved in HOAc (95 mL) and added in one single portion to a stirred solution of NaN02 (1. 17 g, 17.0 mmol) in H2O (8. 4 mL). The flask was sealed with a stopper and the reaction mixture was stirred for 1.5 min at room temperature. The reaction was stopped by the addition of saturated aqueous NaHCO3 (190 mL). After stirring for 10 min at room temperature, the yellow precipitate was filtered, washed with H20 (3 x 30 mL), and dried in vacuo. The yellow residue was then dissolved in a mixture of toluene (75 mL) and MeOH (90 mL). Raney nickel (0.5 g) was washed with MeOH (5 x 10 mL) and added to the reaction mixture. Then the reaction mixture was vigorously stirred under a hydrogen atmosphere at 1 bar at room temperature for 2 h.

Filtration through a pad of Celite and evaporation of the solvent afforded the aniline, which was converted into the corresponding diureas by method A, the corresponding anilines by method D, the corresponding sulfonamides by method B, the corresponding amides by method C or E, or the corresponding thioureas by method I.

Method K: Synthesis of (5-benzothiazol-2-yl-3-chloro-2-hydroxy-phenyl)-ureas, (5- benzothiazol-2-yl-3-chloro-2-hydroxy-phenyl)-thioureas, (3-benzothiazol-2-yl-5-chloro- 4-hydroxy-phenyl)-ureas, (3-benzothiazol-2-yl-5-chloro-4-hydroxy-phenyl)-thioureas, (5- benzothiazol-2-yl-3-chloro-2-hydroxy-phenyl)-amides, and (3-benzothiazol-2-yl-5- chloro-4-hydroxy-phenyl)-amides.

3-Chloro-2-hydroxy-5-nitro-benzoic acid or 3-chloro-4-hydroxy-5-nitro-benzoic acid (0.41 g, 1.9 mmol) was dissolved inpolyphosphoric acid (12.3 g) at 110 °C. 2-Aminothiophenol (0. 36 mg, 2.9 mmol) was added and the resulting solution was stirred at 110 °C for 5 h. After cooling, ammonia (35% in H20, 12 mL) was added to the reaction mixture. The precipitate was filtered, washed with H20 (3 x 10 mL) and dried in vacuo. The residue was then dissolved in a mixture of MeOH (30 mL) and THF (70 mL). Raney nickel (0.5 g) was washed with MeOH (5 x 10 mL) and added to the reaction mixture. Then the reaction mixture was vigorously stirred under a hydrogen atmosphere at 1 bar at room temperature for 1 h.

Filtration through a pad of Celite and evaporation of the solvent afforded the aniline, which was converted into the corresponding ureas by method A, the corresponding amides by method C or E, or the corresponding thioureas by method I.

Method L: Synthesis of (3-amino-5-chloro-4-hydroxy-phenyl)-amides.

Acyl chloride (5.0 mmol) was added to a stirred solution of 4-Amino-2-chloro-phenol (5.0 mmol) in anhydrous CH2CI2 (23 mL) and THF (4 mL) at O°C. After stirring for 12 h, the solvent was evaporated in vacuo. The residue was then dissolved in HOAc (95 mL) and added in one single portion to a stirred solution of NaN02 (1.17 g, 17.0 mmol) in Ha0 (8.4 mL). The flask was sealed with a stopper and the reaction mixture was stirred for 1.5 min at room temperature. The reaction was stopped by the addition of saturated aqueous NaHC03 (190 mL). After stirring for 10 min at room temperature, the yellow precipitate was filtered, washed with H2O (3 x 30 mL), and dried in vacuo. The yellow residue was then dissolved in a mixture of toluene (75 mL) and MeOH (90 mL). Raney nickel (0.5 g) was washed with MeOH (5 x 10 mL) and added to the reaction mixture. Then the reaction mixture was vigorously stirred under a hydrogen atmosphere at 1 bar at room temperature for 2 h.

Filtration through a pad of Celite and evaporation of the solvent afforded the aniline, which was converted into the corresponding ureas by method A, the corresponding anilines by method D, the corresponding sulfonamides by method B, the corresponding diamides by method C or E, or the corresponding thioureas by method I.

Example 2: 1-Adamantan-1-yl-3- (3, 5-dichloro-2-hydroxy-4-methyl-phenyl) -urea To a solution of 6-amino-2, 4-dichloro 3-methyl-phenol hydrochloride (113.5 mg, 1 eq) and DIPEA (48 µL, 1 eq) in dioxan (1.1 mL) was added 1-adamantylisocyanate (88. 5 mg, 1 eq) in 580 uL DMSO in one portion. The solution was stirred at room temperature for 3 h. The solution was diluted with 2 mL DCM and scavenger resins (tris- (2-aminoethyl)-amine polystyrene (3 eq), methylisocyanate polystyrene (3 eq) and N (2-mercaptoethyl) aminomethyl polystyrene (3 eq) ) were added. After 18 h at 40°C the solution was filtered off and the solvent was removed under reduced pressure. The crude product was purified by HPLC to obtain 118 mg (64 %) of the title compound as a white powder.

NMR-'H (DMSO-d6) 8 = 1. 62 (sb, 6H), 1.92 (sb, 6H), 2.05 (sb, 3H), 2.29 (s, 3H), 6.79 (s, 1H), 7.95 (s, 1H), 8.15 (s, 1H), 9.82 (s, 1H).

NMR-13C (DMSO-d6) 8 = 17.1, 29.3, 36.1, 41.5, 50.3, 116.3, 122.1, 123.8, 124.7, 129.9, 140.6, 154. 3 ; MS (m/z) : 369. 2 [M+H+].

Example 3: 1- (3, 5-Dichloro-4-hydroxy-phenyl)-3- (1, 1, 3,3-tetramethyl-butyl)-urea To a solution of 4-amino-2, 6-dichloro-phenol (44.5 mg, 1 eq) in dioxan (2.0 mL) was added 2-isocyanato-2,4, 4-trimethyl-pentane (38 mg, 1 eq) in one portion. The solution was stirred at room temperature for 3 h. The solution was diluted with 2 mL DCM and scavenger resins (tris-(2-aminoethyl)-amine polystyrene (3 eq), methylisocyanate polystyrene (3 eq) and N- (2- mercaptoethyl) aminomethyl polystyrene (3 eq)) were added. After 18 h at 35°C the solution was filtered off and the solvent was removed under reduced pressure. The crude material was purified by HPLC to obtain 67 mg (81%) of the title compound as a white powder.

NMR-'H (DMSO-d6) a = 0.95 (s, 9H), 1.30 (s, 6H), 1.70 (s, 2H), 2.30 (s, 3H), 6.80 (s, 1H), 8. 00 (s, 1H), 8. 08 (s, 1H), 9.83 (Sb, 1H).

NMR-13C (DMSO-d6) 6 = 29. 7,31. 2,50. 5,53. 2,117. 3,122. 4,134. 0,142. 8,153. 9; MS (m/z) : 333.2 [M+H+].

Example 4: 2 N-(2-Hydroxy-4-methyl-phenyl)-C-phenyl-methanesulfonamide The compound was obtained in 32% yield (21.2 mg) using the protocol described in method A.

NMR-'H (DMSO-d6) 8 = 2.13 (s, 3H), 4.97 (s, 2H), 6.70 (d, 1H, J= 8. 2 Hz), 6.78 (s, 1H), 6.83 (d, 1H, J= 8.2 Hz), 7.43 (m, 2H), 7.49 (m, 2H) ; MS (m/z) : 278.1 [M+].

Example 5: Propane-2-sulfonic acid (3,5-dichloro-2-hydroxy-4-methyl-phenyl)-amide The compound was obtained in 47% yield (22.1 mg) using the protocol described in method B.

NMR-'H (DMSO-d6) 6 = 2.25 (d, 6H, J= 6.8), 2.27 (s, 3H), 3.97 (hep, 1H, J= 6.8), 5.39 (s, 1H), 6.91 (s, 1H) ; MS (mlz) : 298. 1 [MH+].

Example 6: N- (3, 5-Dichloro-2-hydroxy-phenyl)-2-phenyl-acetamide The compound was obtained in 22% yield (11.0 mg) using the protocol described in method C.

NMR-'H (DMSO-d6) 6 = 3.06 (s, 2H), 7.25 (m, 1H), 7.31 (m, 2H), 7.32 (m, 2H), 7.61 (m, 2H), 9. 87 (m, 1H); MS (m/z) : 296. 2 [MH+].

Example 7: N- (3, 5-Dichloro-2-hydroxy-4-methyl-phenyl)-N-methyl-2-trifluorome thyl- benzamid Aniline HCL salt (300 mg, 1.3 mmol) and K2CO3 (500 mg) were dissolved in DMSO (5 mL).

CH3I (187 mg, 1.3 mmol) was added and the suspension was stirred for 48 h at room temperature. After filtration, the solvent was removed under reduced pressure. The crude reaction product was purified by preparative HPLC using acetonitrile and water as mobile phase to give the N-methyl amino phenol derivative (130 mg, 31 %).

The amide was obtained in 56% yield (19.7 mg) using the protocol described in method C.

NMR-'H (DMSO-d6) 8 = 2.41 (s, 3H), 3.75 (s, 3H), 7.70-7. 85 (m, 4H), 8.05 (d, 1H, J= 5. 0) ; MS (m/z) : 377.9 [Nfffl.

Example 8: 2, 4-Dichloro-3-methyl-6- (3-methyl-benzylamino)-phenol The compound was obtained in 49% yield (16 mg) using the protocol described in method D.

According to method D. NMR-'H (DMSO-d6) (5 2. 21 (s, 3 H), 2.27 (s, 3 H), 4.27 (s, 2 H), 5.80 (br s, 1 H), 6.35 (s, 1 H), 7.02-7. 24 (m, 4 H), 9.18 (br s, 1 H); MS (m/z) : 296.2 [M+H+].

Example 9: 1-{5-Chloro-3-[2-(4-chloro-phenylsulfanyl)-benzylamino]-2-hy droxy-phenyl}- ethanone The compound was obtained in 18 % yield (12 mg) using the protocol described in method D.

NMR-'H (DMSO-d6) 8 2.60 (s, 3 H), 4.40 (s, 2 H), 6.24 (d, J= 2.0 Hz, 1H), 6.41 (m, 1H), 7.10 (d, J= 2 Hz, 1H), 7.18-7. 24 (m, 2 H), 7.29-7. 44 (m, 6 H), 12.66 (s, 1 H); MS: m/z : 418.5 [M+H+].

Example 10: 4-Chloro-2-[2-(4-chloro-phenylsulfanyl)-benzylamino]-6-(1-hy droxy-ethyl)- phenol The compound was obtained in 34 % yield (23 mg) using the protocol described in method D.

NMR-'H (DMSO-d6) 8 1.27 (d, J= 6.4 Hz, 3 H), 4.33 (s, 2 H), 4.97 (q, J= 6.4 Hz, 1 H), 5.96 . (d, J= 2. 4 Hz, 1 H), 6.47 (d, J= 2.4 Hz, 1 H), 7.19-7. 47 (m, 8 H), 8.69 (br. S, 1 H) ; MS: m/z : 420.7 [M+H+]/ Example 11: (3, 5-Dichloro-2-hydroxy-phenyl)-carbamic acid phenyl ester The compound was obtained in 26 % yield (11 mg) using the protocol described in method F.

NMR-'H (DMSO-d6) S= 7.25 (m, 3H), 7.43 (m, 2 H), 7.50 (s, 2H) NMR-13C (DMSO-d6) 6= 109.1, 118.8, 121.4, 128.2, 129.4, 132.6, 153.2, 157.3 Example 12: (3,5-Dichloro-2-hydroxy-4-methyl-phenyl)-carbamic acid phenyl ester The compound was obtained in 31 % yield (24 mg) using the protocol described in method F.

NMR-'H (DMSO-d6) a= 2.38 (s, 3 H), 6.76 (m, 3H), 7.15 (m, 3H) NMR-i3C (DMSO-d6) #= 16. 5,109. 1,115. 2,118. 8,126. 7, 128. 5,129. 5,129. 7,139. 4,153. 4, 157.4 Example 13: (3,5-Dichloro-2-hydroxy-phenyl)-carbamic acid benzyl ester According to method F 2-amino-4,6-dichloro-phenol (25 mg, 1 eq) and phenylchloroformate (23 I1L, 1 eq) gave 10.9 mg (26 %) of the title compound as a white solid.

NMR-'H (DMSO-d6) 5= 5. 30 (d, 2 H), 7.43 (m, 2 H), 7.25 (m, 2H), 7.50 (s, 2H) Example 14: (3,5-Dichloro-2-hydroxy-4-methyl-phenyl)-carbamic acid 2-isopropyl-5- methyl-cyclohexyl ester The compound was obtained in 39% yield (22 mg) using the protocol described in method G. NMR-'H (DMSO-d6) 6= 0.84-0. 90 (m, 3H), 1.22-1. 41 (m, 6H), 2.35 (s, 3H), 3.28-3. 33 (m, 2H), 4.06 (t, 2H), 7.57 (s, 1H), 8.74 (s, 1H).

Example 15: (3, 5-Dichloro-2-hydroxy-phenyl)-carbamic acid 2-isopropyl-5-methyl- cyclohexyl ester The compound was obtained in 54% yield (44 mg) using the protocol described in method G.

NMR-'H (DMSO-d6) d= 0.75 (d, 3H), 0.82-093 (m, 7H), 0.96-1. 14 (m, 2H), 1.29-1. 53 (m, 2H), 1.59-1. 71 (m, 2H), 1. 88-2. 02 (m, 2H), 4.54 (ddd, 1H), 7.47 (s, 2H), 9.67 (s, 1H), 9.73 (s, 1H) Example 16: (3, 5-Dichloro-2-hydroxy-4-methyl-phenyl)-carbamic acid hexyl ester The compound was obtained in 21% yield (10 mg) using the protocol described in method G. NMR-'H (DMSO-d6) J= 0.87 (t, 3H), 1.25-1. 40 (m, 6H), 1.55-1. 66 (m, 2H), 2.35 (s, 3H), 4.06 (t, 2H), 7.56 (s, 1H), 8.74 (s, 1H), 9.73 (s, 1H).

Example 17: (3, 5-Dichloro-2-hydroxy-phenyl)-carbamic acid hexyl ester The compound was obtained in 43% yield (30 mg) using the protocol described in method G. NMR-'H (DMSO-d6) (5 = 0.87 (t, 3H), 1.21-1. 40 (m, 6H), 1.54-1. 66 (m, 2H), 4.06 (t, 2H), 7.46 (s, 2H), 9.67 (s, 1H), 9.73 (s, 1H).

Example 18: 1- [3-Chloro-5- (3-cyclohexyl-ureido)-2-hydroxy-phenyl]-3- (1, 1,3, 3- tetramethyl-butyl)-urea The compound was obtained in 31% yield (16 mg) using the protocol described in method J.

NMR-'H (DMSO-d6) 8 1.06 (s, 9 H), 1.08-1. 28 (m, 5 H), 1.35 (s, 6 H), 1. 45-1. 76 (m, 7 H), 3.30-3. 42 (m, 1 H), 6.84 (s, 1 H), 7.24 (s, 1 H), 7.73 (s, 1 H), 8. 20 (br. s, 1 H), 8.82 (s, 1 H), 8.97 (s, 1 H), 9.11 (s, 1 H); MS: m/z : 439.2 [M+H+].

Example 19: N-[3-Chloro-5-(3-cyclohexyl-ureido)-2-hydroxy-phenyl]-2-nitr o- benzenesulfonamide According to method J 1- (3-amino-5-chloro-4-hydroxy-phenyl)-3-cyclohexyl-urea (19 mg, 67 (J. mol) and 2-nitro-benzenesulfonyl chloride (15 mg, 67 fimol) gave N [3-Chloro-5- (3- cyclohexyl-ureido)-2-hydroxy-phenyl]-2-nitro-benzenesulfonam ide (15 mg, 48%).

NMR-'H (DMSO-d6) 6 1.05-1. 37 (m, 5 H), 1.49-1. 83 (m, 5 H), 3.42-3. 47 (m, 1 H), 5.94 (d, J = 7.9 Hz, 1 H), 6.99 (d, J= 2.4 Hz, 1 H), 7.46 (d, J= 2.4 Hz, 1 H), 7. 78-7. 90 (m 2 H), 7.93- 8.03 (m, 2 H), 8.27 (s, 1 H), 9.19 (br s, 1 H), 9.70 (s, 1 H) ; MS: m/z : 469.1 [M+H+].

Example 20: 1- (3-Benzothiazol-2-yl-5-chloro-4-hydroxy-phenyl)-3-cyclohexyl -urea According to method K 4-amino-2-benzothiazol-2-yl-6-chloro-phenol (21 mg, 76 4mol) and isocyanato-cyclohexane (9.5 mg, 76 llmol) gave 1- (3-Benzothiazol-2-yl-5-chloro-4-hydroxy- phenyl)-3-cyclohexyl-urea (3.0 mg, 10%).

NMR-'H (DMSO-d6) 8 1.09-1. 41 (m, 5 H), 1.49-1. 87 (m, 5 H), 3.41-3. 47 (m, 1H), 6.12 (d, J = 7. 8 Hz, 1 H), 7.51 (t, J= 7.8 Hz, 1 H), 7.60 (t, J=7. 1 Hz, 1 H), 7.68 (d, J= 2.4 Hz, 1 H), 8.06 (d, J= 2.4 Hz, 1 H), 8. 11 (d, J= 8.3 Hz, 1 H), 8.21 (d, J= 7.3 Hz, 1 H), 8.52 (s, 1 H), 11.92 (s, 1 H); MS: mlz : 402.2 [M+H+].

Example 21: 1- (5-Benzothiazol-2-yl-3-chloro-2-hydroxy-phenyl)-3- (2-trifluoromethyl- phenyl)-thiourea According to method K 2-Amino-4-benzothiazol-2-yl-6-chloro-phenol (20 mg, 72 pmol) and 1-isothiocyanato-2-trifluoromethyl-benzene (15 mg, 72 µmol) gave 1- (5-benzothiazol-2-yl-3- chloro-2-hydroxy-phenyl)-3- (2-trifluoromethyl-phenyl)-thiourea (12 mg, 35%).

NMR-'H (DMSO-d6) 8 7.40-7. 56 (m, 3 H), 7.66-7. 79 (m, 3 H), 7.92 (d, J= 2.4 Hz, 1 H), 8.03 (d, J= 7.8 Hz, 1 H), 8.12 (d, J= 8.8 Hz, 1 H), 8. 68 (br s, 1 H), 9.65 (s, 1 H), 9.94 (s, 1 H), 10.65 (s, 1 H); MS: m/z : 480.0 [M+H+]. Example 22: 1- (3, 5-Dichloro-2-hydroxy-4-methyl-phenyl)-3- (4-trifluoromethyl-phenyl)- thiourea The compound was obtained in 57% yield (59 mg) using the protocol described in method I. NMR-'H (DMSO-d6) 8 = 2.38 (s, 3 H), 7.68-7. 85 (m, 5 H), 9.43 (s, 1 H), 9.90 (s, 1 H), 10.37 (s, 1 H) ; MS (m/z) : 278.1 [M+].

Example 23: 1-Adamantan-1-yl-3- (3, 5-dichloro-4-hydroxy-phenyl) -urea The compound was obtained in 60% yield (35 mg) using the protocol described in method A. NMR-'H (DMSO-d6) 6 = 1. 60 (Sb, 6H), 1.95 (Sb, 6H), 2.08 (Sb, 3H), 6.79 (s, 1H), 7.95 (s, 1H), 8. 18 (s, 1H), 9.82 (s, 1H).

NMR-l3C (DMSO-d6) 6 = 17. 2,29. 5, 36. 1, 41.7, 50.3, 116.2, 122.2, 123.8, 124.8, 140.6, 154.3 ; MS (m/z) : 369.2 [M+H+].

Example 24: 1- (3, 5-Dichloro-4-hydroxy-phenyl)-3- (1, 1, 3,3-tetramethyl-butyl)-urea To a solution of 4-amino-2, 6-dichloro-phenol (44.5 mg, 1 eq) in dioxan (2.0 mL) was added 2-isocyanato-2,4, 4-trimethyl-pentane (38 mg, 1 eq) in one portion. The solution was stirred at room temperature for 3 h. The solution was diluted with 2 mL DCM and scavenger resins (tris- (2-aminoethyl)-amine polystyrene (3 eq), methylisocyanate polystyrene (3 eq) and N- (2- mercaptoethyl) aminomethyl polystyrene (3 eq)) were added. After 18 h at 35°C the solution was filtered off and the solvent was removed under reduced pressure. The crude material was purified by HPLC to obtain 67 mg (81 %) of the title compound as a white powder.

NMR-'H (DMSO-d6) 8 = 0.95 (s, 9H), 1.28 (s, 6H), 1.69 (s, 2H), 5.90 (s, 1H), 7.33 (s, 2H), 8.22 (s, 1H), 9.50 (Sb, 1H).

NMR-l3C (DMSO-d6) 6 =29. 9,31. 2,50. 9,54. 2,117. 3,121. 4,134. 0,142. 8, 152.9 ; MS (m/z) : 333.2 [M+H+].

Example 25: 1- (3, 5-Dichloro-4-hydroxy-phenyl)-3- (4-trifluoromethyl-phenyl)-thiourea The compound was obtained in 58% yield (34.8 mg) using the protocol described in method I.

NMR-'H (DMSO-d6) 6 = 6.32 (m, 2 H), 6.80 (m, 2 H), 7.42 (m, 2 H), MS (m/z) : 381.2 [M+].

Example 26: Propane-2-sulfonic acid (3, 5-dichloro-2-hydroxy-4-methyl-phenyl)-amide The compound was obtained in 40% yield (21 mg) using the protocol described in method B. NMR-'H (DMSO-d6) 3 = 2.43 (d, 6H), 2.51 (s, 3H), 3.97 (m, 1H), 5. 43 (s, 1H), 6.8 (s, 1H); MS (m/z) : 284.1 [MH+].

Example 27: N-(3,5-Dichloro-4-hydroxy-phenyl)-2-phenyl-acetamide The compound was obtained in 22% yield (11.0 mg) using the protocol described in method C.

NMR-'H (DMSO-d6) 6 = 3.12 (s, 2H), 7.24 (m, 1H), 7.36 (m, 2H), 7.37 (m, 2H), 7.61 (m, 2H), 9.91 (m, 1H) ; MS (m/z) : 296.2 [MH+].

Example 28: 2, 6-Dichloro-4- (3-methyl-benzylamino)-phenol The compound was obtained in 55% yield (15.0 mg) using the protocol described in method D.

NMR-'H (DMSO-d6) # 2. 26 (s, 3 H), 4.29 (s, 2 H), 5.92 (s, 1 H), 6.50 (s, 1 H), 7.00-7. 28 (m, 4 H), 9.20 (s, 1 H); MS (m/z) : 282.2 [M+H+].

Example 29: (3,5-Dichloro-4-hydroxy-phenyl)-carbamic acid phenyl ester The compound was obtained in 49% yield (55.7 mg) using the protocol described in method.

F.

NMR-iH (DMSO-d6) 8= 7.22 (m, 2H), 7.36 (m, 2 H), 7.50 (s, 2H) NMR-t3C (DMSO-d6) d= 118.5, 121.9, 122.5, 125.5, 129.4, 131.7, 144.7, 150.3, 151.6 Example 30: (3-Chloro-4-hydroxy-phenyl)-carbamic acid phenyl ester The compound was obtained in 46% yield (32.1 mg) using the protocol described in method F.

NMR-'H (DMSO-d6) J= 2.38 (s, 3 H), 6.76 (s, 1H), 7.15 (m, 5H), 7.32 (m, 2 H).

NMR-13C (DMSO-d6) = 16.5, 109.1, 115.2, 118.8, 126.7, 128.5, 129.5, 129.7, 139.4, 153.4, 157.4 Example 31: (3,5-Dibromo-4-hydroxy-phenyl)-carbamic acid phenyl ester The compound was obtained in 25 % yield (10.2 mg) using the protocol described in method F.

NMR-'H (DMSO-d6) S= 7.33 (m, 2 H), 7.45 (m, 2H), 7.50 (s, 2H) Example 32: (3,5-Dichloro-4-hydroxy-phenyl)-carbamic acid 2-isopropyl-5-methyl- cyclohexyl ester According to method G 4-amino-2, 6-dichloro-phenol (40 mg, 1 eq) and (-)- menthylchloroformate (54 p1, 1.1 eq) in DCM gave 44.1 mg (54 %) of the title compound as a white solid.

NMR-IH (DMSO-d6) S= 0.71 (d, 3H), 0. 78-0. 96 (m, 7H), 0.99-1. 16 (m, 2H), 1.29-1. 58 (m, 2H), 1.59-1. 71 (m, 2H), 2.0-2. 15 (m, 2H), 4.58 (m, 1H), 7.49 (s, 2H), 9.68 (s, 1H), 9.73 (s, 1H) Example 33: (3, 5-Dichloro-4-hydroxy-phenyl)-carbamic acid hexyl ester According to method G 4-amino-2, 6-dichloro-phenol (40 mg, 1 eq) and hexylchloroformate (41 µL, 1.1 eq) gave 30 mg (43 %) of the title compound as a white solid.

NMR-IH (DMSO-d6) d= 0.75 (m, 3H), 1.21-1. 40 (m, 6H), 1.48-1. 62 (m, 2H), 4.22 (m, 2H), 7.32 (s, 2H), 9.69 (s, 1H), 9.75 (s, 1H). Example 34: 1- [3-Chloro-5- (3-cyclohexyl-ureido)-2-hydroxy-phenyl]-3- (2-trifluoromethyl- phenyl)-urea According to method J 1- (3-amino-5-chloro-4-hydroxy-phenyl)-3-cyclohexyl-urea (30 mg, 0.11 mmol) and 1-isocyanato-2-trifluoromethyl-benzene (21 mg, 0.11 mmol) gave 1- [3- chloro-5- (3-cyclohexyl-ureido)-2-hydroxy-phenyl]-3- (2-trifluoromethyl-phenyl)-urea (16 mg, 31%).

NMR-'H (DMSO-d6) 8 0.98-1. 28 (m, 5 H), 1.39-1. 76 (m, 5 H), 3.30-3. 42 (m, 1 H), 5.84 (d, J = 7. 8 Hz, 1 H), 7.24 (d, J= 7.8 Hz, 1 H), 7.31 (d, J= 2.4 Hz, 1 H), 7.52-7. 67 (m, 2 H), 7.71- 7.75 (m, 2 H), 8.20 (br. s, 1 H), 8.80-8. 82 (m, 1 H), 8.97-9. 04 (m, 1 H), 9.11 (s, 1 H); MS: m/z : 471.1 [M+H+].

Example 35: Specificity of inhibition of certain enzymes by compounds according to the present invention In order to characterize the specificity of various compounds the following assays were performed. PPIase activity of hFinl, hCypl8, LpCypl8, hFKBP12 and EcParvulin was measured using the protease-coupled PPIase assay according to Fischer et al. (Fischer, G.; Bang, H.; Mech, C. Determination of enzymatic catalysis fort he cis-trans-isomerization of peptide binding in proline-containing peptides. [German] Biomed. Biochem. Acta 1984,43, 1101-1111 ; Hennig et al. , Selective Inactivation of Parvulin-like peptidyl-prolyl cis/trans isomerases by Juglon, Biochemistry. 1998,37 (17): 5953-5960). For hPinl measurements Ac- Ala-Ala-Ser (P03H2)-Pro-Arg-pNA was used as a substrate and trypsin (final concentration 190 llg/ml) as an isomer-specific protease. Activity measurements of other PPIases were made with the substrate peptide Suc-Ala-Phe-Pro-Phe-pNA and the protease-chymotrypsin (final concentration 470 tig/ml). The assays were performed in a final reaction volume of 150 gel at final concentrations of 6 nM hPinl, 10 nM hCypl8, 5 nM LpCypl8, 20 nM EcParvulin and 20 nM hFKBP12, respectively, and 120, uM substrate peptide in 35 mM HEPES (pH 7.8). For inhibition experiments 100-0.01 uM of effector freshly diluted from a DMSO stock solution were added. The amount of solvent was kept constant within each experiment, usually below 0.3% (v/v). All reactions were started by addition of protease. The test was performed by observing the released 4-nitroaniline at 390 nm with a MR5000 W/Vis spectrophotometer (Dynex) at 6°C. Data were evaluated by calculation of pseudo-first-order rate constants kobs in presence of PPIase and PPIase/effector, respectively, and corrected for the contribution of the non-catalyzed reaction (ko). Inhibition constants ICSO were calculated using SigmaPlot 8.0 (SPSS).

The following target enzymes which are all rotamases belonging to different classes of rotamases were used: T-1 : Protein interacting with NIMA (-kinase), hPinl T-2: First described human Rapamycin receptor, hFKBP12 T-3: Human Cyclosporin A receptor with 18 kDa molecular weight, hCypl8 T-4: Leishmonia pneumophila virulence Cyclosporin A receptor with 18 kDa molecular weight, LpCypl8 T-5: Bacterial Juglon sensitive non proteolytic enzyme, EcParv These rotamases are known in the art. Their production and characteristics may be taken from the following references.

Review about all PPIase families Gothel, S. F.; Marahiel, M. A. TI Peptidyl-prolyl cis-trans isomerases, a superfamily of ubiquitous folding catalysts [Review]. Cell. Molec. Life Sci. 1999,55, 423-436 Pinl Lu, K. P.; Hanes, S. D. ; Hunter, T. (1996) A human peptidyl-prolyl isomerase essential for regulation of mitosis. Nature 1996, 380, 544-547 Yaffe, M. B.; Schutkowski, M.; Shen, M. H.; Zhou, X. Z.; Stukenberg, P. T.; Rahfeld, J.

U.; Xu, J.; Kuang, J.; Kirschner, M. W.; Fischer, G.; Cantley, L. C.; Lu K. P.

SEQUENCE-SPECIFIC AND PHOSPHORYLATION-DEPENDENT PROLINE ISOMERIZATION-A POTENTIAL MITOTIC REGULATORY MECHANISM.

Science 1997, 278, 1957-1960 Shen, M. ; Stukenberg, P. T.; Kirschner, M. W.; Lu, K. P. The essential mitotic peptidyl-prolyl isomerase Pinl binds and regulates mitosis-specific phosphoproteins. Genes Develop. 1998, 12, 706-720.

EcParvulin Rahfeld JU. Schierhorn A. Mann K. Fischer G. A novel peptidyl-prolyl cis/trans isomerase from Escherichia coli. FEBSLetters. 1994, 343, 65-69 Rahfeld JU. Rucknagel KP. Schelbert B. Ludwig B. Hacker J. Mann K. Fischer G.

Confirmation of the existence of a third family among peptidyl-prolyl cis/trans isomerases.

Amino acid sequence and recombinant production of parvulin. FEBS Letters. 1994, 352, 180- 184 FKBPs (including FKBP12) and Cyclophilins (including Cypl8) For recent reviews on cyclophilins and FKBPs and their effectors, see: (a) Fischer, G.

Peptidyl-prolyl cisltrans isomerases and their effectors. Angew. Chem., Int. Ed. Engl. 1994, 33, 1415-1436. (b) Galat, A.; Metcalfe, S. M. Peptidylproline cisltrans isomerases. Prog.

Biophys. Molec. Biol. 1995, 63, 67-118.

LpCypl8 Schmidt B. Tradler T. Rahfeld JU. Ludwig B. Jain B. Mann K. Rucknagel KP. Janowski B.

Schierhorn A. Kullertz G. Hacker J. Fischer G. A cyclophilin-like peptidyl-prolyl cis/trans isomerase from Legionella pneumophila--characterization, molecular cloning and overexpression. Mol. Microbiol. 1996, 21, 1147-1160 In order to cluster the various rotamase inhibitors the following classes were defined with"A" indicating the most potent rotamase inhibitor.

A: IC50 < 1, uM B: 1 µM <IC50 <10 µM C : 10 µM <IC50 <50 µM D: 50 µM<IC50 <100 µM E : IC50 > 100 uM Table 2 Specificity of the inhibition with rotamases A: IC50 < 1 SLM B: lM<IC50<10uM C: 10 gM < IC50 < 50 uM D: 50 µM <IC50 <100 µM E: IC50 > 100 uM Table 2 Specificity of the inhibition with rotamases No Target Compound T-1 T-2 T-3 T-4 T-5 OH H H CI N N fizz 120 c D c E- ce ? Target N° Target Compound T-1 T-2 T-3 T-4 T-5 OH OH . 655 C E E E C cl OH HOP cl N sX A3 cl 512 C E D E C ci OH OH OH. _ _ Cl >/kg N S w /9 02 563 B E E E E ci OH H H ci NyN 109 A E C E C 0 -o ci OH H CI N 0 599 B E E D C ci OU CI N N C ! N Nj J c 11 NyN 118 B D C C B ci OH H H NyN 643 c E E E E H H IIN,,, qNyN 605 E C E B H N N 605 A E C E B 101 HO I ci N° Target Compound T-l T-Z T-3 T-4 T-5 OH H H_5 CI N N CtCN) 266 A E E B ci OH OH ! H H ci N N 629 A E C E B ce ci OH OH cri NEZ N 102 B E C C B ci C ! OH ! H H ! C'N N cl 30 B E E E E i o ci OH H H cl NyN 264 s CF3 Cl OH f ! l ! H H OH ci N N 254 A _ _ _ _ ci OH H H CI N'N 639 s N No Target Compound T-1 T-2 T-3 T-4 T-5 OH OH cl NyN r s S N 640 B t s < 257 A Cl OH OH Ho Su C ! OH H H F N N OH _ cl OH OU F N N 127 B-_ _ _ ber OH OU H H F ; N N 127 B II _ _ _ _ OH Br OH HO o ci OH 0 y 31 A 0 cl o n' N° Target Compound T-1 T-2 T-3 T-4 T-5 OH ! H H ci N N 637 B---_ Son OU OH b CI N\ . N A W OH.. __ t S < 638 638 B SON OH H H CI 0 N HH son OH su ci Ny N 0' O.. L 622 A S4N OH ! H H OH H H CI N N\ /9 O HN < 656 A ) r 0 ci No Target Compound T-1 T-2 T-3 T-4 T-5 OH CI N \ ci N. 371 A E c E ce ci ci OU N \ 672 A C B C C OH ° _ ci OU OH H O cri N OH 647 B E E E E ci OH CIN I O ci 483 B E C E D ci Oh CI N O ci 482 B E C E E ci Ci OU CI N \ , S 343 B E C E E ci ? Target Compound T-1 T-2 T-3 T-4 T-5 OHM CI N \ J 441 B E C E E ci ci OH F N ! ! J I 399 A E D D C i ci OH OH ILS cri N ce un cri OH OH N N NN i o o i 673 A--_ _ ci cri Oh Oh , s \ 400 A-_ _ _ 400 A NOS 'a,, NO 719 A E D C HO H H ci NyN H H CI N'N I n I/ If zu 703 A E E E B HO C) CI N° Target Compound T-1 T-2 T-3 T-4 T-5 Ho CI NON q. 700A E E E C HO I 0 HO c NYNO H H C'N N o 710 A E E E E HO Of CI c N t) n jj 716 B E E E C Ho 0 CRI H CI N ci 1273 A E E E B HA CL / CI N 1293 B E E E C HO I O CL NOS cri N A C 1294 A E E E B Ho CL CFs H H CI N N cl B94 A E X E B s HO CRI H CI N I O 0 1295 B E E E B Cri Ct N° Target Compound T-1 T-2 T-3 T-4 T-5 CIN 4 1296 B E C E C HOIR I cl ZIZI cj NHb) 1297 A E E E C HO I O Ci CI CI N \ 1298 A E E E C HO CI o o- Hov 1299 A E A E C HO HO"y Ci OH N HOX Su 1044 A C C B C Ho I \ As may be taken from the above table 2 the following compounds 24, 88, 89,110, 169,170, 298,342, 344,377, 378,700, 703,710, 894,1273, 1294,1297 are of class A and are thus extremely specific for hPinl.

Example 36: Specificity of inhibition of proteases In order to investigate the impact of some of the inventive compounds on the activity of key proteases the following assay was performed: Protease activities were measured spectrophotometrically at 30°C according to Schomburg and Salzmann (Schomburg, B.; Salzmann M. GBF: Enzyme Handbook. Springer Verlag, Berlin Heidelberg, 1991) and Bergmeyer et al. (Bergmeyer, H. U.; Bergmeyer, J.; Graßl, M. Methods of Enzymatic Analysis, Vol. V Enzymes 3: Peptides, Proteinases and Their Inhibitors. pp 55-371, VCH, Weinheim, 1988). The release of 4-nitroaniline was determined at 390 nm with a Spectramax Plus UV/Vis spectrophotometer (Molecular Devices). The cathepsin B assay was performed in a reaction mixture containing 0.2 µ/ml cathepsin B, 2 mM Z-Arg-Arg-pNA in 88 mM KH2P04, 12 mM Na2HPO4, 1.33 mM EDTA, 0.03% Brij 35 (pH 5.8). The trypsin assay was carried out in a reaction mixture containing 0. 1 µg/ml trypsin and 120 aM Ac-Ala-Ala- Ser (P03H2)-Pro-Arg-pNA in 35 mM HEPES (pH 7.8) and the papain assay in a mixture consisting of 16 ug/ml papain and 2 mM Bz-DL-Arg-pNA in 10 mM Na2HP04, 2 mM L-Cys, 5 mM EDTA (pH 6.5). In general, reactions were started by addition of peptide substrate after a 30 min incubation of 1-100 uM effector with given concentrations of enzyme.

The key proteases used were the following: T-6: Papain T-7: Trypsin T-8: Cathepsin In order to cluster the various compounds the following classes of activity were defined.

A: IC50 < 1 uM B : 1, uM < IC50 < 10 pM C: 10 uM < IC50 < 50, uM D: 50 µM <IC50 <500 µM E: IC50 > 100 pM Table 3 Specificity of the inhibition of some proteases N° Target Compound T-6 T-7 T-8 N° Target Compound T-6 T-7 T-8 OH HO 102 D C D C ! ci OH HH ci NyN 109E 0 cul ci OH CI N N , Nv N 118 f E- ci OH HO NyN 643E X o OH ! H H OH HO 264 E E E caf3 CI OH CI N S 02 563E cri Ci OU CI N 371 E-- ci ci OH OH CIN cl 599 E D ci N° Target Compound T-6 T-7 T-8 OH cul N 645 E i o ci OH cri N , 497 E-C cl OH ci N 644 E- o ci OH CI N t 646 E E ci OH CI N 6 9 E-D CF3 ci OU H ci N 498E ci C) ? Target Compound T-6 T-7 T-8 OH CRI N I O ci 499 E ce H CI N \ 343 E ci OH H Cl N 441 E s ci ci OH FN 385 E bar/ Cl ci OH 399 E zu ce ci CloN v 1296 E E E HO ci CL CI N Ho 0 1273 E E E cl N° Target Compound Compound T-6 T-7 T-8 HO - NyN p i i 703 E D E HO ci CL Tin CI N'N Ho 710 E HO CI. H H CI N N T 716 B-- HO cl As may be taken from table 3 none of the tested compound is a strong inhibitor of any of the key proteases tested.

Example 37: Cytotoxic effects on tumor cell lines In order to show that the compounds according to the present invention are actually useful in the treatment of tumors, the cytotoxic effects of some of said compounds on tumor cell lines were determined.

For this cytotoxic evaluation of the compounds the commercial available WST-1 assay (Roche) was used according to the manufacturer's instructions. The assay is based on the cleavage of the tetrazolium salt WST-1 by mitochondrial dehydrogenases found in viable cells. In general compounds were added to cells cultured in 96-well plates at 37°C. After 48 h of incubation 10 ul of WST-1 solution was added. The formazan dye was analyzed with an ELISA plate reader at (450 vs. 620) nm.

The following tumor cell lines were used in this assay: CL-1 : human acute myeloid leukemia, HL-60 CL-2: human cervix carcinoma, HeLa CL-3: human prostate carcinoma, PC-3 CL-4: human colon adenocarcinoma, Caco-2 CL-5 : human breast adenocarcinoma, MCF-7 In order to cluster the efficacy of the various compounds the following classes in terms of EC50 were defined.

A: EC50 < 10 uM B: 10 µM <EC50 <50 µM C : 50 µM <EC50 <100 µM D: 100 uM < EC50 < 200 uM E: EC50 200 uM Table 4 Cytotoxic effects on tumor cell lines N° Target Compound CL-1 CL-2 CL-3 CL-4 CL-5 OH OH ci N N T | {102 A A A A A cl I ci OH COG H H a-N N ! ! 261 A B B B B s cl OH H H C'N II II 264 A A A A A s caf3 cl N° Target Compound CL-1 CL-2 CL-3 CL-4 CL-5 OH HO GI N NEZ ci I I 109. B A B-A ci OH ! H H ci N N CI N N \ y 254 B B B-B s Cl t N Y N < 3 0 A _ _ A _ ci Cl tN < N t 221 B _ _ _ B OH HO CI N N 30 A--A- cl Ci HO CI N N , /221 B-_ _ ci OH HO NyN 6 B A /O Cl OH H H k'4 (yTTT 6 a---A o OH NN 54 B A , oui OH __N N 150 B A F) j HYH*T F 0 N° Target Compound CL-1 CL-2 CL-3 CL-4 CL-5 OH H H CI S ! I/Sr I, son OH OH CI s N t S f 640 B---B SON ou OH H H CI N'N\ /S / 653 A---B A W OH H H ci N N T 629 A A A A-A s ci OH OH oX 645 A A A-A 0 ci N° Target Compound CL-1 CL-2 CL-3 CL-4 CL-5 OH CI N \ 329. B B B-B cl ce OH OH 11 N O i, 493 B A A ce OMe OH CRI N Cl X 484 B A A cl OH CI N 483 B B cri Cri H F N \ 399 A A A ZEA s cl OH H cl N 0 cl CN han 0 N° Target Compound CL-1 CL-2 CL-3 CL-4 CL-5 OH r.) OH F \ N \ 357. A A A-_ ce Cri OH OH 413 B A B ci, ci ci OH F'W s 402 B B B Cl ; NH 9 332 j B B {3 | _ l cil ce OU CI N \ 332 B, B B-- cri/ OH OH 630 B A A ci OH F N 403 B A A-- C ! ce N° Target Compound CL-1 CL-2 CL-3 CL-4 CL-5 OH CI N cri N han 631 A-B-- ci OH \ zizi CI N \ HN NtHO Cl 632 A B ce OH OU ci N s ci Oh ou ! H H H H ! OH OH CI N N. . N N CI o ° f\ o a ci ci N° Target Compound CL-1 CL-2 CL-3 CL-4 CL-5 OH H cri N I----p cl HN 9, CI Zon Ci CI N , 0 1273 B C B B- Ho H H CL C ! N/N I n r I 4 ! 703 B B B B HO ci CRI H CI N n/ 1296 C HO Ci /I Holy Po Ho iso HA OH i 1044 B B B-- HO CRI As may be taken from table 4 all of the tested compounds are highly efficient in exhibiting a cytotoxic effect on at least one of the various tumor cell lines tested. Of particular relevance are compounds 102,264, 357,399, 629,633, 645,652, 673,703, 1044,1273.

Example 38: FACS measurements and TUNEL assay In order to show that the compounds according to the present invention are actually useful for inducing apoptosis in tumor cells, FACS measurements and TUNEL assay were performed.

Enari M. Sakahira H. Yokoyama H. Okawa K. Iwamatsu A. Nagata S. A caspase-activated DNase that degrades DNA during apoptosis, and its inhibitor ICAD [erratum appears in Nature 1998 May 28 ; 393 (6683): 396. ]. Nature. 391 : 43-50, 1998 Darzynkiewicz Z. Juan G. Li X. Gorczyca W. Murakami T. Traganos F. Cytometry in cell necrobiology: analysis of apoptosis and accidental cell death (necrosis). Cyromet7y. 27 : 1-20, 1997 Apoptotic HL-60 cells were detected by FACS analysis of FITC-dUTP-labelled DNA breaks using the Apo-Direct kit (BD-Pharmingen) according to the manufacturer's protocol.

As may be taken from Fig. 2 compounds 102 and 264 induce apoptosis in tumor cells.

Example 39 : Cyclin D1 down regulation In order to show that the compounds according to the present invention are actually acting the expected way and induces cyclin D1 down regulation, cyclin D1 marker analysis were performed MCF-7 (5X105 cells/well) and HeLa cells (1. 5X105 cells/well) were seeded in 6-well plates and incubated at 37°C over night. Compounds or DMSO (final solvent concentration 0. 1%) were added to the cells and incubated for different times as indicated. Subsequently, cells were lysed in RIPA buffer for 30 min on ice and centrifuged for 20 min at 4°C. After addition of electrophoresis sample buffer (4x) and 50 mM DTT to the supernatant, samples were boiled for 4 min at 95°C. Samples (equivalent to 2x105 cells/well) were run on a 15% SDS gel followed by blotting onto PVDF membrane.

The membrane was blocked for 1 h in 10 mM Tris (pH 7.5), 100 mM NaCI, 0. 1% Tween-20 and 5% non-fat dry milk (blocking buffer) and incubated for 1 h with mouse anti-hCyclin D1 monoclonal antibody (clone DCS-6, BD Biosciences) diluted to 1 Mg/ml in blocking buffer.

Blots were washed 3 x 10 min with 10 mM Tris (pH 7.5), 100 mM NaCl, 0.1% Tween-20 (washing buffer) and incubated with 0. 7 ug/ml peroxidase-conjugated sheep anti-mouse IgG - (Sigma) in blocking buffer for 1 h. After washing 3 x 10 min with washing buffer, the plot was developed with the ECL+ detection kit (Amersham Biosciences).

Of particular relevance are compounds 30,102, 264,399, 629,639, 657,673.

Example 40: DAPI staining In order to show that the compounds according to the present invention are actually useful for inducing apoptosis in tumor cells, DAPI staining was performed.

Hela cells grown on poly-L-Lys-coated coverslips were fixed with 2% paraformaldehyde/MeOH.

Cellular DNA was stained with DAPI staining buffer (100 mM Tris (pH 7.4), 150 mM NaCI, 1 mM CaCl2, 0.5 mM MgC12, 0. 1% nonidet P-40, 1 , g/ml DAPI (Molecular Probes) ). All the steps were performed at room temperature, and cells were washed two times with PBS after each step. Finally, cells were mounted in 80% glycerol/PBS.

As may be taken from Fig. 3 compounds 30,102, 264 and 399 induce apoptosis in tumor cells.

The features of the present invention disclosed in the specification, the claims and/or the drawing may both separately and in any combination thereof be material for realizing the invention in various forms thereof.