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Title:
TRICYCLIC COMPOUNDS WITH ANTIVIRAL ACTIVITY
Document Type and Number:
WIPO Patent Application WO/2001/051479
Kind Code:
A2
Abstract:
The present invention provides a compound of the formula (I) and pharmaceutically acceptable salts having useful antiviral activity against viruses of the herpes family. In said formula, X = O, (CH¿2?)¿m?, S, SO, SO¿2?, NH, NR¿8? or a chemical bond; Y = O, (CH¿2?)¿m?, S, SO, SO¿2?, NH, NR¿8?; Z = NH, O, NR¿8?, S, SO, SO¿2?. The remaining substituents are described in the specification.

Inventors:
BOOTH RICHARD JOHN (US)
JOSYULA VARA PRASAD VENKATA NA (US)
MEYER ANNETTE LYNN (US)
STEINBAUGH BRUCE ALLAN (US)
Application Number:
PCT/US2000/032571
Publication Date:
July 19, 2001
Filing Date:
November 30, 2000
Export Citation:
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Assignee:
WARNER LAMBERT CO (US)
BOOTH RICHARD JOHN (US)
JOSYULA VARA PRASAD VENKATA NA (US)
MEYER ANNETTE LYNN (US)
STEINBAUGH BRUCE ALLAN (US)
International Classes:
A61K31/136; A61K31/137; A61K31/343; A61K31/357; A61K31/36; A61K31/381; A61K31/382; A61K31/39; A61K31/403; A61K31/4035; A61K31/404; A61K31/4178; A61K31/426; A61K31/427; A61K31/4355; A61K31/4365; A61K31/44; A61K31/4402; A61K31/4406; A61K31/4409; A61K31/443; A61K31/4433; A61K31/4439; A61K31/444; A61K31/4468; A61K31/4525; A61K31/47; A61K31/4709; A61K31/5415; A61K31/55; A61P31/12; A61P31/22; C07C211/61; C07C215/88; C07C217/94; C07C317/32; C07D209/88; C07D211/58; C07D213/38; C07D215/12; C07D223/22; C07D279/10; C07D279/20; C07D307/91; C07D319/24; C07D327/08; C07D333/20; C07D333/54; C07D333/76; C07D335/02; C07D401/12; C07D405/04; C07D405/12; C07D407/12; C07D407/14; C07D409/12; C07D409/14; C07D411/12; C07D417/12; C07D491/048; C07D497/04; (IPC1-7): C07D307/91; A61K31/39; A61P31/22; C07C211/61; C07D209/88; C07D223/22; C07D279/10; C07D319/24; C07D327/08; C07D333/54; C07D333/76; C07D409/12; C07D497/04
Domestic Patent References:
WO1998030544A11998-07-16
WO1995004723A11995-02-16
Foreign References:
US3932424A1976-01-13
US3929802A1975-12-30
US3673191A1972-06-27
US3592819A1971-07-13
GB1040737A1966-09-01
US5049464A1991-09-17
DE19813979A11999-09-30
US3413291A1968-11-26
US2990368A1961-06-27
GB863550A1961-03-22
GB1268772A1972-03-29
Other References:
PATENT ABSTRACTS OF JAPAN vol. 1998, no. 09, 31 July 1998 (1998-07-31) & JP 10 101591 A (EISAI CO LTD), 21 April 1998 (1998-04-21)
HAGEN ET AL.: "Synthesis of 6-substituted beta-carbolines..." J.MED.CHEM., vol. 30, 1987, pages 750-753, XP002163825
CHEMICAL ABSTRACTS, vol. 128, no. 23, 8 June 1998 (1998-06-08) Columbus, Ohio, US; abstract no. 279731, DAS ET AL.: "Investigation on the pesticidal.." XP002163826
CHEMICAL ABSTRACTS, vol. 94, no. 23, 8 June 1981 (1981-06-08) Columbus, Ohio, US; abstract no. 192046, KUMAR ET AL.: "A novel aromatization during enamine..." XP002163827
CHEMICAL ABSTRACTS, vol. 36, no. 14, 20 July 1942 (1942-07-20) Columbus, Ohio, US; UFIMTSEV: "Enoid systems without auxo-groups" column 4110; XP002163828
CHEMICAL ABSTRACTS, vol. 63, no. 7, 27 September 1965 (1965-09-27) Columbus, Ohio, US; ZHURAVLEV ET AL.: "Synthesis in the phenothiazine series..." column 8348; XP002163829
CHEMICAL ABSTRACTS, vol. 127, no. 17, 27 October 1997 (1997-10-27) Columbus, Ohio, US; abstract no. 234293, LOLOIU ET AL.: "Isatin chemistry..." XP002163830
CHEMICAL ABSTRACTS, vol. 77, no. 17, 23 October 1972 (1972-10-23) Columbus, Ohio, US; abstract no. 114109, LETUNOV ET AL.: "Synthesis and basicity ..." XP002163831
CHEMICAL ABSTRACTS, vol. 111, no. 24, 11 December 1989 (1989-12-11) Columbus, Ohio, US; abstract no. 215115, ROSLANIEC ET AL.: "Preparation of polyester..." XP002163832
CHEMICAL ABSTRACTS, vol. 108, no. 10, 7 March 1988 (1988-03-07) Columbus, Ohio, US; abstract no. 76424, KYZIOL ET AL.: "Carbazole antioxidants..." XP002163833
WANG W ET AL: "Hepatitis C viral IRES inhibition by phenazine and phenazine-like molecules" BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,GB,OXFORD, vol. 10, no. 11, June 2000 (2000-06), pages 1151-1154, XP004200544 ISSN: 0960-894X
Attorney, Agent or Firm:
Federman, Evan J. (NJ, US)
MANSMANN, Ivo (Patent Dept. Gödecke AG Mooswaldallee 1 Freiburg, DE)
Download PDF:
Claims:
CLAIMS :
1. A compound of Formula I or a pharmaceutically acceptable salt thereof wherein : X0,(CH2)m,S,SO,S02,NH,NRs or a chemical bond ; Y = 0, (CH2) m, S, SO, S02, NH, NRs ; Z = N, NH, O, NHRg, NRs, S, SO, S02 ; n = an integer of from 0 to 2 ; m = an integer of 1, 2, or 3 ; Ri, R2, Rs, R4, Rs independently are hydrogen, halogen, hydroxyl, amino, mono or dialkylamino, cyano, nitro, alkyl groups (16 carbon atoms), alkoxy groups (16 carbon atoms), CF3, OCF3, aminoalkyl (16 carbon atoms), aminoaryl, Oaryl, or a heterocyclic ring having 57 atoms with 14 hetero atoms of N, O or S ; Ar = phenyl, substituted phenyl, benzoheterocyclic ring, substituted benzoheterocyclic ring, heterocyclic ring, or substituted heterocyclic ring, which have substitutions R6 or R7 ; R6 and R7 are independently hydrogen, alkyl group (16 carbon atoms), cycloalkyl (3 12 carbon atoms), halogen, alkoxy, CF3, aminoalkyl (16 carbon atoms), aminoaryl, or a heterocyclic ring of from 57 atoms with 14 heteroatoms of N, O or S ; R6 and : may also form a ring, optionally cycloalkyl or aryl or substituted aryl ; Rg is hydrogen, alkyl (16 carbon atoms), cycloalkyl (312 carbon atoms), phenyl or substituted phenyl wherein the substituents are as defined above.
2. The compound of claim 1 having Formula II.
3. The compound of claim 1 having Formula III.
4. The compound of claim 1 having Formula IV.
5. The compound of claim 1 having Formula V.
6. The compound of claim 1 having Formula VI.
7. The compound of claim 1 having Formula VII.
8. A pharmaceutical composition for the treatment of infection or disease caused by a virus, which comprises an amount of the compound of Claim 1 sufficient to provide an antivirally effective dosage of the compound of Formula I and a pharmaceutically effective carrier.
9. A pharmaceutical composition for the treatment of infection or disease caused by a virus, which comprises an amount of the compound of Claim 1 in the range of about 1 to about 50 mg/kgday or up to 3 g per day and a pharmaceutically effective carrier.
10. A method of treatment of infection or disease caused by a virus, which comprises administering to a subject in need of such treatment a composition of Claim 1.
11. The composition of claim 8 wherein the virus is a Herpes virus.
12. The composition of claim 9 wherein the virus is a Herpes virus.
13. The method of claim 10 wherein the virus is a Herpes virus.*& 14.
14. 2. 1] hept2yldibenzofuran2ylamine 21 (4tertButylcyclohexyl)dibenzofuran2ylamine 22 Bicyclo [3. 2. 1] oct2yldibenzoiran2ylamine 23 Cyclopentyldibenzofuran2ylamine 24 Cyclohexyl (2methoxydibenzofuran3yl)amine 25Cyclohexyl (9Hfluoren2yl)amine 26 Dibenzofuran2ylbis (3methylsulfanylpropyl)amine 27 Dibenzofuran2ylbis (3methylbutyl)amine 28 Dibenzofuran2yldipropylamine 29 N3(1,1Dioxohexahydrothiopyran4yl)N2,N2dimethyl9Hfluorene2, 3 diamine 30 N3IsopropylN2, N2dimethyl9Hfluorene2, 3diamine 31 N2, N2DimethylN3(tetrahydrothiopyran4yl)9XIfluorene2, 3diamine 32 N3CyclohexylN2, N2dimethyl9Hfluorene2, 3diamine 33 N3CycloheptylN2, N2dimethyl9Hfluorene2, 3diamine 34 N3(lEthylpropyl)N2, N2dimethyl9Hfluorene2, 3diamine 35 N3(lCyclopropylethyl)N2, N2dimethyl9Hfluorene2, 3diamine 36 N3secButylN2, N2dimethyl9Hfluorene2, 3diamine 37 (9HFluoren2yl)isopropylamine 38 (9HFluoren2yl) (tetrahydrothiopyran4yl)amine <BR> <BR> <BR> <BR> 39 Cycloheptyl (9Hfluoren2yl)amine<BR> <BR> <BR> <BR> <BR> <BR> 40 Dibenzo : filran2yl(l, 1dioxohexahydrothiopyran4yl)amine<BR> <BR> <BR> <BR> <BR> <BR> 41 Dibenzofuran2ylpiperidin4ylamine<BR> <BR> <BR> <BR> <BR> <BR> 42Dibenzofuran2ylisopropylamine 43 Cyclohexyldibenzofuran2ylamine <BR> <BR> <BR> 44 (1Cyclopropylethyl)dibenzofuran2ylamine<BR> <BR> <BR> <BR> <BR> <BR> <BR> 45 Dibenzofuran3yl (l, 1dioxohexahydrothiopyran4yl)amine<BR> <BR> <BR> <BR> <BR> <BR> 46 Dibenzofuran3ylpiperidin4ylamine 47Dibenzofuran3ylisopropylamine 48Dibenzofuran3yl (tetrahydrothiopyran4yl)amine 49 Cyclohexyldibenzofuran3ylamine 50 Cycloheptyldibenzofuran3ylamine 51 (4Chlorobenzyl)dibenzofuran2ylamine 52 (4Chloro3nitrobenzyl)dibenzofuran2ylamine 53 Dibenzofuran2yl (3trifluoromethoxybenzyl)amine 54 Benzo[1,3]dioxol5ylmethyldibenzofuran2ylamine 55 Dibenzofilran2yl(2, 3dihydrobenzo [1, 4] dioxin6ylmethyl)amine <BR> <BR> <BR> <BR> 56Dibenzofuran2yl (3, 5dimethoxybenzyl)amine<BR> <BR> <BR> <BR> <BR> <BR> 57 Dibenzofiuran2yl(4trifluoromethylbenzyl)amine 58 Dibenzofuran2yl (2methylbenzyl)amine 59 Dibenzofuran2ylthiophen3ylmethylamine 60 Dibenzofuran2yl (4nitrobenzyl)amine 61 Dibenzofuran2yl (4methylsulfanylbenzyl)amine 62 Dibenzofuran2yl(4methylbenzyl)amine 63 Benzyldibenzofuran2ylamine 64 (3Benzyloxybenzyl)dibenzofuran2ylamine 65 (1Benzylbutyl)dibenzofuran2ylamine 66 Dibenzofuran2yl[2(2methoxyphenyl)1methylethyl]amine 673 (Dibenzofuran2ylamino)2methylbutan1ol 68 Dibenzofuran2yl (1ethylbutyl)amine 69 Dibenzofuran2yl (1ethylpropyl)amine 70 Dibenzofuran2yl (1, 3dimethylbutyl)amine 71 (1Cyclohexylethyl)dibenzofuran2ylamine 72 Cyclooctyldibenzofuran2ylamine 73 Cycloheptyldibenzofuran2ylamine 74 Dibenzofuran2yl(tetrahydrothiopyran4yl)amine 75 Dibenzofuran2yl (tetrahydrothiophen3yl)amine 76 Dibenzofuran2yl (1, 2dimethylpropyl)amine 77 Dibenzofuran2yl (1methylbutyl)amine 78 secButyldibenzofuran2ylamine 79 Benzofurp [3, 2b] pyridin8yl (2fluorobenzyl)amine 80 Benzofuro [3, 3b] pyridin8ylpyridin4ylmethylamine 81 Benzofuro [3, 2b] pyridin8yl(2methylbenzyl)amine <BR> <BR> <BR> <BR> 82 N (2Fluorobenzyl)N'methyldibenzofuran2, 8diamine<BR> <BR> <BR> <BR> <BR> <BR> <BR> 83 NMethylN'quinolin4ylmethyldibenzofuran2, 8diamine<BR> <BR> <BR> <BR> <BR> <BR> 84NMethylN"naphthanlen1ylmethyldib enzofuran2, 8diamine 85 N (4Methanesulfonylbenzyl)N'methyldiebnzofuran2, 8diamine 86NMethylN'pyridin4ylmethyldibensofuran2, 8diamine 87 NMethylN' (2methylbenzyl)dibenzofuran2, 8diamine 88 Naphthanlen1ylmethyl (1 OHphenothiazin2yl)amine 89 (4Methanesulfonylbenzyl) (lOHphenothiazin2yl)amine 90 (3Fluoro2methylbenzyl) (10oxa9thia1azaanthracen6yl)amine 91 (2Fluoro2methylbenzyl) (10oxa9thialazaanthracen6yl)amine 92 (10Oxa9thia1azaanthracen6yl)qinolin4ylmethylamine 93 Naphthalenelylmethyl(10oxa9thia1azaanthracen6yl)amine 94 (4Methanesulfonylbenzyl) (10oxa9thia1azaanthracen6yl)amine 95 (10Oxa9thia1azaanthracen6yl)pyridin4ylmethylamine 96 (2Methylbenzyl) (10oxa9thialazaanthracen6yl)amine 97 Anthracen2ylquinolin4ylmethylamine <BR> <BR> 98 Anthracen2yl (4methanesulfonylbenzyl)amine<BR> <BR> 99 Anthracen2ylpyridin4ylmethylamine 100 Anthracen2yl (2methylbenzyl)amine 101 Dibenzo [b, e] [1, 43dioxin2yl(2fluorobenzyl)amine 102 Dibenzo [b, e] [1, 4] dioxin2yl (2fluorobenzyl)amine 103 Dibenzo [b, e] [1, 4] fioxin2ylquinolin4ylmethylamine 104 Dibenzo [b, e] [1, 4] fioxin2ylnaphthalen1ylmethylamine 105 Dibenzo [b, e] [1, 4] fioxin2yl (4methanesulfonylbenzyl)amine 106 Dibenzo [b, e] [1, 4] fioxin2ylpyridin4ylmethylamine 107 8 (3Fluoro2methylbenzylamino)dibenzofuran2ol 1088 (2Fluorobenzylamino)dibenzofuran2ol 109 8(4Methanesulfonylbenzylamino)dibenzofuran2ol 110 8 [ (Pyridin4ylmethyl)amino]dibenzofuran2ol 111 8(2Methylbenzylamino)dibenzofuran2ol 112 (8Chlorodibenzofuran2yl) (2fluorobenzyl)amine 113 8Chlorodibenzofuran2yl)naphthalen1ylmethylamine 114 8Chlorodibenzofuran2yl) (4methanesulfonylbenzyl)amine 115 (4Methanesulfonylbenzyl)(6, 7, 8, 9tetrahydro5Hcarbazol3yl)amine 116 Pyridin4ylmethyl(6, 7 ; 8, 9tetrahydro5Hcarbazol3yl)amine 117 Benzofuro [3, 2b] pyridin8yl (3fluoro2methylbenzyl)amine <BR> <BR> 118 Dibenzofuran2ylquinolin4ylmethylamine<BR> <BR> 119 Dibenzofuran2ylquinolin2ylmethylamine<BR> <BR> 120 (4Dimethylaminobenzyl) (8fluorodibenzofuran2yl)amine 121 Dibenzofuran2yl (4dimethylaminobenzyl)amine <BR> <BR> 122 Diebnzofuran2yl (5nitrothiophen2ylmethyl)amine<BR> <BR> 123 Dibenzofuran2ylthiazol2ylmethylamine 124 Benzyl (8fluorodibenzofuran2yl)amine <BR> <BR> 125 N (3Methoxybenzyl)N'methyldibenzofuran2, 8diamine<BR> <BR> 1 26 N(3, 5Dimethoxybenzyl)N'methyldibenzofuran2, 8diamine 127 N (4tertButylbenzyl)N'methyldibenzofuran2, 8diamine <BR> <BR> 128 NBenzylN'methyldibenzofuran2, 8diamine<BR> <BR> 129 2 [ (8Methylaminodibenzofuran2ylamino)methyl]benzonitrile 130 (4Methoxybenzyl)phenoxathiin3ylamine 131 (8Chlorodibenzofuran2yl) (3methoxybenzyl)amine 132 (3Methoxybenzyl)phenoxathiin3ylamine 133 (3, 5Dimethoxybenzyl)phenoxathiin3ylamine 134 (3Fluoro4methoxybenzyl)phenoxathiin3ylamine 135 (4tertButylbenzyl)phenoxathiin3ylamine 136 Benzylphenoxathiin3ylamine 137 (2Ethoxybenzyl)phenoxathiin3ylamine 138 (8Chlorodibenzofuran2yl) (3, 5dimethoxybenzyl)amine 139 (8Chlorodibenzofuran2yl) (3fluoro4methoxybenzyl)amine 140 Benzyl (8chlorodibenzofuran2yl)amine 141 (9HFluoren2yl) (4methoxybenzyl)amine 142 (8Chlorodibenzofuran2yl)thiazol2ylmethylamine 143 (9HFluoren2yl) (3methoxybenzyl)amine 144 (3, 5Dimethoxybenzyl) (9Hfluoren2yl)amine 145 (9HFluoren2yl) (3fluoro4methoxybenzyl)amine 146 (4tertButylbenzyl)(9Hfluoren2yl)amine 147 Benzyl (9Hfluoren2yl)amine 148 (9HFluoren2yl)thiazol2ylmethylamine 149 (2Ethoxybenzyl) (9Hfluoren2ylamine 150 Dibenzofuran4yl (4methoxybenzyl)amine 151 2 [ (8Chlorodibenzofuran2ylamino)methyl]benzonitrile 152 Dibenzofuran4yl (3methoxybenzyl)amine 153 Dibenzofuran4yl (3, 5dimethoxybenzyl)amine 154 Dibenzofuran4yl (3fluoro4methoxybenzyl)amine 155 (4tertButylbenzyl)dibenzofilran4ylamine 156Dibenzofuran4yl (2ethoxybenzyl)amine 157 N (4Methoxybenzyl)N'methyldibenzofuran2, 8diamine 158 (8Chlorodibenzofuran2yl) (4methoxybenzyl)amine 159 (8Chlorodibenzofuran2yl) (2ethoxybenzyl)amine 160 Dibenzofuran4yl (2, 4dimethylbenzyl)amine 161 NMethylN'thiophen3ylmethyldibenzofuran2, 8diamine 162 NMethylN'pyridin2ylmethyldibenzofuran2, 8diamine 163 (2Bromobenzyl)phenoxathiin3ylamine 164 Phenoxathiin3ylquinolin4ylmethylamine 165 Phenoxathiin3ylthiophen3ylmethylamine 166 (3Methylpyridin2ylmethyl)phenoxathiin3ylamine 167 Phenoxathiin3ylpyridin3ylmethylamine 168 Phenoxathiin3ylpyridin2ylmethylamine 169 (8Chlorodibenzofuran2yl)thiophen3ylmethylamine 170 (2Bromobenzyl) (9ethyl9Hcarbazol3yl)amine 171 (8Chlorodibenzofuran2yl) (3methylpyridin2ylmethyl)amine 172 (9Ethyl9Hcarbazol3yl)thiophen3ylmethylamine <BR> <BR> 173 (5Chlorothiophen2ylmethyl) (9ethyl9Hcarbazol3yl)amine 174 (9Ethyl9Hcarbazol3yl)pyridin3ylmethylamine <BR> <BR> 175 (2Bromobenzyl) (9Hfluoren2yl)amine<BR> <BR> 176 (8Chlorodibenzofuran2yl)pyridin4ylmethylamine 177 (9HFluoren2yl)quinolin2ylmethylamine 178 (9HFluoren2yl)thiophen3ylmethylamine 179 (9HFluoren2yl) (3methylpyridin2ylmethyl)amine 180 (9HFluoren2yl)pyridin4ylmethylamine 181 (9HFluoren2yl)pyridin3ylmethylamine 182 (9HFluoren2yl)pyridin2ylmethylamine 1 33 (8Chlorodibenzofuran2yl)pyridin3ylmethylamine 184 Dibenzofuran4ylquinolin4ylmethylamine 185 Dibenzofuran4ylquinolin2ylmethylamine 186Dibenzofuran4ylthiophen3ylmethylamine <BR> <BR> 187 Dibenzofuran4yl (3methylpyridin2ylmethyl)amine<BR> <BR> 188 Dibenzofuran4ylpyridin4ylmethylamine<BR> <BR> 1 89 Dibeffzofuran4ylpyridin3ylmethylamine<BR> <BR> 190 l7ibenzofuran4ylpyridin2ylmethylamine<BR> <BR> 191 (2Bromobenzyl) (8chlorodibenzofuran2yl)amine 192 (8Chlorodibenzofuran2yl)pyridin2ylmethylamine 193 NMethylN' (2, 3, 6trifluorobenzyl)dibenzofuran2, 8diamine 194 NMethylN' (2, 3, 4trifluorobenzyl)dibenzofuran2, 8diamine 195 N (2, 6Difluorobenzyl)N'methyldibenzofuran2, 8diamine 1 96 N(2, 5Difluorobenzyl)N'methyldibenzofilran2, 8diamine 197 N (2, 4Difluorobenzyl)N'methyldibenzofuran2, 8diamine 198 N (2, 3Difluorobenzyl)N'methyldibenzofuran2, 8diamine 199 N (2, 5Dimethylbenzyl)N'methyldibenzofuran2, 8diamine 200 N(2, 4Dimethylbenzyl)N'methyldibenzofuran2, 8diamine 201 N (2, 3Dihydrobenzo [l, 4] dioxin6ylmethyl)N'methyldibenzofuran2, 8 diamine 202 (3Fluoro2methylbenzyl)phenoxathiin3ylamine 203 (8Chlorodibenzofuran2yl) (2, 3, 6trifluorobenzyl)amine 204 Phenoxathiin3yl (2, 3, 6trifluorobenzyl)amine 205 Phenoxathiin3yl (2, 3, 4trifluorobenzyl)amine 206 (2, 6DiRuorobenzyl)phenoxathiin3ylamine 207 (2, 5Difluorobenzyl)phenoxathiin3ylamine 208 (2, 4Difluorobenzyl)phenoxathiin3ylamine 209 (2, 3Difluorobenzyl)phenoxathiin3ylamine 210 (2, 4Dimethylbenzyl)phenoxathiin3ylamine 211 (2, 3Dihydrobenzo [1, 4] dioxin6ylmethyl)phenoxathiin3ylamine 212 Benzo [b] thiophen5yl (3fluoro2methylbenzyl)amine 213 (8Chlorodibenzofuran2yl) (2, 3, 4trifluorobenzyl)amine 214 (8Chlorodibenzofuran2yl) (2, 6difluorobenzyl)amine 215 (8Chlorodibenzofuran2yl) (2, 5difluorobenzyl)amine 216 (8Chlorodibenzofuran2yl) (2, 4difluorobenzyl)amine 217 (9Ethyl9Hcarbazol3yl)(3fluoro2methylbenzyl)amine 218 (8Chlorodibenzofuran2yl) (2, 3difluorobenzyl)amine 219 (9Ethyl9Hcarbazol3yl) (2, 3, 6trifluorobenzyl)amine 220 (9Ethyl9Hcarbazol3yl)(2, 3, 4trifluorobenzyl)amine 221 (2, 6Difluorobenzyl) (9ethyl9Hcarbazol3yl)amine 222 (2, 5Difluorobenzyl) (9ethyl9Hcarbazol3yl)amine 223 (2, 4Difluorobenzyl) (9ethyl9Hcarbazol3yl)amine 224 (2, 3Difluorobenzyl) (9ethyl9Hcarbazol3yl)amine 225 (2, 5Dimethylbenzyl)(9ethyl9Hcarbazol3yl)amine 226 (2, 4Dimethylbenzyl) (9ethyl9Hcarbazol3yl)amine 227 (2, 3Dihydrobenzo [1, 4] dioxin6ylmethyl) (9ethyl9Hcarbazol3yl)amine 228 (9HFluoren2yl) (3fluoro2methylbenzyl)amine 229 (8Chlorodibenzofuran2yl)(2, 5dimethylbenzyl)amine 230 (9HFluoren2yl) (2, 3, 6trifluorobenzyl)amine 231 (9HFluoren2yl)(2, 3, 4trifluorobenzyl)amine 232 (2, 5Difluorobenzyl)(9IIfluoren2yl)amine 233 (2, 4Difluorobenzyl) (9Hfluoren2yl)amine 234 (2, 3Difluorobenzyl) (9Hfluoren2yl)amine 235 (2, 5Dimethylbenzyl) (9Hfluoren2yl)amine 236 (2, 4Dimethylbenzyl) (9Hfluoren2yl)amine 237 (2, 3Dihydrobenzo [1, 4] dioxin6ylmethyl) (9Hfluoren2yl)amine 238 (8Chlorodibenzofuran2yl)(2, 4dimethylbenzyl)amine 239 Dibenzofuran4yl (2, 5dimethylbenzyl)amine 240 Dibenzofuran4yl (3fluoro2methylbenzyl)amine 241 N(3Fluoro2methylbenzyl)N'methyldibenzofuran2,8diamine 242 (8Chlorodibenzofuran2yl) (3fluoro2methylbenzyl)amine 243 (8Chlorodibenzofuran2yl) (2, 3dihydrobenzo [1, 4] dioxin6ylmethyl)amine 244 (2, 5Dimethoxybenzyl)phenoxathiin3ylamine 245 (2, 3Dimethoxybenzyl)phenoxathiin3ylamine 246 (2Chlorobenzyl)phenoxathiin3ylamine 247 (2Methoxybenzyl)phenoxathiin3ylamine 248 (2Methylbenzyl)phenoxathiin3ylamine 249 Anthracen2yl(2chlorobenzyl)amine 250 Anthracen2yl (2fluorobenzyl)amine 251 Dibenzo [1, 4] dioxin2yl(2, 3dimethoxybenzyl)amine 252 (2Chlorobenzyl)dibenzo [1, 4] dioxin2ylamine 253 2(lDibenzo [1, 4] dioxin2ylaminomethyl)phenol 254 Dibenzo [1, 4] dioxin2yl (2methoxybenzyl)amine 255 2 [ (9Ethyl9Hcarbazol3ylamino)methyl]phenol 256 (9Ethyl9Hcarbazol3yl) (2fluorobenzyl)amine 257 (9Ethyl9Hcarbazol3yl)(2methylbenzyl)amine 258 (2Chlorobenzyl) (9Hfluoren2yl)amine 259 2 [ (9HFluoren2ylamino)methyl]phenol 260 (9HFluoren2yl)(2methoxybenzyl)amine 261 (9HFluoren2yl) (2trifluoromethylbenzyl)amine 262 (9HFluoren2yl) (2fluorobenzyl)amine 263 Dibenzofuran4yl (2, 5dimethoxybenzyl)amine 264 Dibenzofuran4yl (2, 3dimethoxybenzyl)amine <BR> <BR> <BR> 265 2 (Dibenzofuran4ylaminomethyl)phenol<BR> <BR> <BR> <BR> <BR> 266 Dibenzofuran4yl (2methoxybenzyl)amine 267 (2, 5Dimethoxybenzyl) (3methoxydibenzofuran2yl)amine 268 (2, 3Dimethoxybenzyl) (3methoxydibenzofuran2yl)amine 269 (2Methoxybenzyl) (3methoxydibenzofuran2yl)amine <BR> <BR> 270 Dibenzofiaran2yl (2, 5dimethoxybenzyl)amine<BR> <BR> <BR> <BR> <BR> <BR> 271 Dibenzofuran2yl (4methoxybenzyl)amine 272 (2Bromobenzyl)dibenzofuran2ylamine 273 (8Fluorodibenzofuran2yl) (3Himidazol4ylmethyl)amine 274 2 [ (8Fluorodibenzofuran2ylamino)methyl]benzonitrile 275 (2Ethoxybenzyl) (8fluorodibenzofuran2yl)amine 276 (8Fluorodibenzofuran2yl) (4methylsulfanylbenzyl)amine 277 (2Bromobenzyl) (8fluorodibenzofuran2yl)amine 278 (8Fluorodibenzofuran2yl)quinolin4ylmethylamine 279 (8Fluorodibenzofuran2yl)quinolin2ylmethylamine 280 Dibenzofuran2ylnaphthalen1ylmethylamine 281 (8Fluorodibenzofuran2yl)naphthalen2ylmethylamine 282 (8Fluorodibenzofuran2yl)naphthalen1ylmethylamine 283 Dibenzofuran2yl (2nitrobenzyl)amine 284 Dibenzofuran2yl (3Himidazol4ylmethyl)amine 285 2(Dibenzofuran2ylaminomethyl)benzonitrile <BR> <BR> <BR> 286 Dibenzofuran2yl(2ethoxybenzyl)amine<BR> <BR> <BR> <BR> <BR> 287 Dibenzofuran2yl(3trifluoromethylbenzyl)amine 288 (4tertButylbenzyl)dibenzofuran2ylamine 289 Dibenzofuran2yl (3fluorobenzyl)amine 290 (2, 5Dimethoxybenzyl) (8fluorodibenzofuran2yl)amine 291 (2, 3Dimethoxybenzyl) (8fluorodibenzofuran2yl)amine 292 (4Benzyloxybenzyl) (8fluorodibenzofuran2yl)amine 293 (3Benzyloxybenzyl) (8fluorodibenzofuran2yl)amine 294 (4Chlorobenzyl) (8fluorodibenzofuran2yl)amine 295 (3Chlorobenzyl) (8fluorodibenzofuran2yl)amine 296 (2Chlorobenzyl) (8fluorodibenzofuran2yl)amine 297 4 [ (8Fluorodibenzofuran2ylamino)methyl]phenol 298 3 [ (8Fluorodibenzofuran2ylamino)methyl]phenol 299 Dibenzofuran2yl (2fluorobenzyl)amine 300 (8Fluorodibenzofuran2yl) (4methoxybenzyl)amine 301 (8Fluorodibenzofuran2yl) (3methoxybenzyl)amine 302 (8Fluorodibenzofuran2yl) (2methoxybenzyl)amine 303 (8Fluorodibenzofuran2yl) (4trifluoromethylbenzyl)amine 304 (8Fluorodibenzofuran2yl) (3trifluoromethylbenzyl)amine 305 (4tertButylbenzyl) (8fluorodibenzofuran2yl)amine 306 (4Fluorobenzyl) (8fluorodibenzofuran2yl)amine 307 (3Fluorobenzyl) (8fluorodibenzofuran2yl)amine 308 (2Fluorobenzyl) (8fluorodibenzofuran2yl)amine 309 (8Fluorodibenzofuran2yl) (4methylbenzyl)amine 310 (8Fluorodibenzofuran2yl) (3methylbenzyl)amine 311 Dibenzofuran2yl (2, 6dimethoxybenzyl)amine 312 Dibenzofuran2yl (2, 4dimethoxybenzyl)amine 313 Dibenzofuran2yl (2, 3dimethoxybenzyl)amine 314 (4Benzyloxybenzyl)dibenzofuran2ylamine 315 Dibenzofuran2yl (3methylbenzyl)amine 316 (3Chlorobenzyl)dibenzofilran2ylamine 317 3 (Dibenzofuran2ylaminomethyl)phenol 318 (2Chlorobenzyl)dibenzoiran2ylamine 319 Dibenzofuran2yl (3methoxybenzyl)amine 320 Dibenzofuran2yl (2methoxybenzyl)amine 321 (9HFluoren2yl) (2methylbenzyl)amine 322Dibenzofuran4yl (2methylbenzyl)amine 323 (8Chlorodibenzofuran2yl) (2methylbenzyl)amine 324 (2Methylbenzyl)(lOHphenothiazin2yl)amine 325 Dibenzo [b, e] [1, 4] dioxin2yl (2methylbenzyl)amine 326 Dibenzofuran2yl (2, 6difluorobenzyl)amine 327 Dibenzofuran2yl (2, 5difluorobenzyl)amine 328Dibenzofuran2yl (2, 4difluorobenzyl)amine 329 Dibenzofuran2yl (2, 3difluorobenzyl)amine 330 (8Fluorodibenzofuran2yl)thiophen2ylmethylamine 331Dibenzofuran2yl (2, 5dimethylbenzyl)amine 332 (8Fluorodibenzofuran2yl)thiophen3ylmethylamine 333 (8Fluorodibenzofuran2yl)furan2ylmethylamine 334 (8Fluorodibenzofuran2yl)furan3ylmethylamine 335 (8Fluorodibenzofuran2yl) (6methylpyridin2ylmethyl)amine 336 (8Fluorodibenzofuran2yl) (4methanesulfonylbenzyl)amine 337 (8Fluorodibenzofuran2yl)pyridin4ylmethylamine 338 (8Fluorodibenzofuran2yl)pyridin3ylmethylamine 339 (8: Fluorodibenzofilran2yl)pyridin2ylmethylamine 340 (8Fluorodibenzofuran2yl) (3fluoro4methoxybenzyl)amine 341 Dibenzofuran2yl (2, 4dimethylbenzyl)amine 342 (8Fluorodibenzofuran2yl) (3fluoro2methylbenzyl)amine 343 (8Fluorodibenzofuran2yl) (2, 3, 6trifluorobenzyl)amine 344 (8Fluorodibenzofuran2yl) (2, 3, 4trifluorobenzyl)amine 345 (3, 5Difluorobenzyl) (8fluorodibenzofuran2yl)amine 346 (3, 4Difluorobenzyl) (8fluorodibenzofuran2yl)amine 347 (3, 5difluorobenzyl) (8fluorodibenzofuran2yl)amine 348 (2, 6Difluorobenzyl (2, 5Difluorobenzyl) (8fluorodibenzofuran2yl)amine 349 (2, 4Difluorobenzyl) (8fluorodibenzofuran2yl)amine 350 (2, 3Difluorobenzyl)(8fluorodibenzofiuran2yl)amine 351 (2, 5Dimethylbenzyl) (8fluorodibenzofuran2yl)amine 352 (2, 4Dimethylbenzyl) (8fluorodibenzofuran2yl)amine 353 (2, 3Dihydro1, 4benzodioxin6ylmethyl) (8fluorodibenzofuran2yl)amine 354 (3, 5Dimethoxybenzyl) (8fluorodibenzofuran2yl)amine 355 Dibenzofuran2ylfuran2ylmethylamine 356 Dibenzofuran2ylfuran3ylmethylamine <BR> <BR> <BR> 357 Dibenzofuran2yl (6methylpyridin2ylmethyl)amine<BR> <BR> <BR> <BR> <BR> <BR> 358 Dibenzofuran2yl (4methanesulfonylbenzyl)amine<BR> <BR> <BR> <BR> <BR> 359 Dibenzofuran2ylpyridin4ylmethylamine 360 Dibenzofuran2ylpyridin3ylmethylamine <BR> <BR> 361 Dibenzofuran2ylpyridin2ylmethylamine<BR> <BR> 362 Dibenzofuran2yl (3fluoro4methoxybenzyl)amine 363 Dibenzofuran2yl (3fluoro2methylbenzyl)amine 364 Dibenzofuran2yl(2, 3, 6trifluorobenzyl)amine 365 Dibenzofuran2yl(2, 3, 4trifluorobenzyl)amine 366 Dibenzofuran2yl (3, 5difluorobenzyl)amine 367 Dibenzofuran2yl(3, 4difluorobenzyl)amine 368 Dibenzoirarl2yl(3, 4dimethoxybenzyl)amine 369 Dibenzofuran2ylmethyl (2methylbenzyl)amine 370 Dibenzothiohen2yl(2,4dimethylbenzyl)amine 371 (4tertButylbenzyl)dibenzothiohen2ylamine 372 (2Chlorobenzyl)dibenzothiohen2ylamine 373 Dibenzothiohen2yl (2, 6difluorobenzyl)amine 374 Dibenzothiohen2yl(2, 3, 6trifluorobenzyl)amine 375 Dibenzothiohen2yl (2fluorobenzyl)amine 376 Benzyldibenzothiohen2ylamine <BR> <BR> 377 Dibenzothiohen2yl (4methoxybenzyl)amine<BR> <BR> 378 Dibenzothiohen2yl(2, 3dimethoxybenzyl)amine 379 Dibenzothiohen2yl (2, 5difluorobenzyl)amine 380 Dibenzothiohen2yl (3methoxybenzyl)amine 381 Dibenzothiohen2yl(2, 3, 4trifluorobenzyl)amine 382 (2Bromobenzyl)dibenzothiohen2ylamine 383 Dibenzothiohen2yl(2, 3dihydro1, 4benzodioxin6ylmethyl)amine 384 Dibenzothiohen2yl (3fluoro4methoxybenzyl)amine 385 Dibenzothiohen2yl(2, 5dimethylbenzyl)amine 386 Dibenzothiohen2ylthiophen3ylmethylamine <BR> <BR> 387 Dibenzothiohen2ylnaphthalene1ylmethylamine<BR> <BR> 388 Dibenzothiohen2yl (2trifluoromethylbenzyl)amine 389 Dibenzothiohen2ylnaphthalen2ylmethylamine 390 Dibenzothiohen2yl(2ethoxybenzyl)amine 391 (10, 11Dihydro5Hdibenz [b, Qazepin2yl)(3fluoro2methylbenzyl)amine 392 (10, 11Dihydro5Hdibenz [b, f]azepin2yl)(2methylbenzyl)amine 393 (10, 11Dihydro5Hdibenz [b, f]azepin2yl)(2,4dimethylbenzyl)amine 394 (4tertButylbenzyl)(10,11dihydro5Hdibenz [b, flazepin2yl)amine 395 (2Chlorobenzyl) (10, 11dihydro5Hdibenz[b,f]azepin2yl)amine 396 (2, 6Difluorobenzyl)(10,11dihydro5Hdibenz[b,f]azepin2yl)amine 397 (10, 11Dihydro5Hdibenz [b, l9azepin2yl)(2, 3, 6trifluorobenzyl)amine 398 (10, 11DihydroSHdibenz [b, f] azepin2yl)(2fluorobenzyl)amine 399 (10, 11Dihydro5Hdibenz [b, f]azepin2yl)(3, 5dimethoxybenzyl)amine 400 Benzyl(10, 11dihydro5EIdibenz [b, Qazepin2yl)amine 401 (10, 11Dihydro5Hdibenz [b, rqazepin2yl)(4methoxybenzyl)amine 402 (10, 11Dihydro5Hdibenz [b, nazepin2yl)(2, 3dimethoxybenzyl)amine 403 (2, 5difluorobenzyl)(10,11dihydro5Hdibenz [b, f]azepin2yl)amine 404 (10, 11Dihydro5Hdibenz [b, f] azepin2yl) (3methoxybenzyl)amine 405 (10, 11Dihydro5Hdibenz [b, fazepin2yl)(2, 3, 4trifluorobenzyl)amine 406 (2Bromobenzyl)(10, 11dihydro5Hdibenz [b, Qazepin2yl)amine 407 (2, 3Dihydro1, 4benzodioxin6ylmethyl)(10,11dihydro5H dibenz [b, fazepin2yl)amine 408 (10, 11Dihydro5Hdibenz [b, f] azepin2yl) (3fluoro4methoxybenzyl)amine 409 (10, 11Dihydro5Hdibenz [b, f) azepin2yl) (2, 5dimethylbenzyl)amine 410 (10, 11Dihydro5Hdibenz [b, vqåzepin2yl)thiophen3ylmethylamine 411 (10, 1 lDihydro5Hdibenz [b, fJazepin2yl)naphthalen1ylmethylamine 412 (10, 11Dihydro5Hdibenz [b, nazepin2yl)(2trifluoromethylbenzyl)amine 413 (10, 1 lDihydro5Hdibenz [b, fjazepm2yl)naphthalen2ylmethylamme 414 (10, 11Dihydro5Hdibenz [b, f]azepin2yl)(2ethoxybenzyl)amine 415 (3Fluoro2methylbenzyl) (10Hphenothiazin2yl)amine 416 (2, 4Dimethylbenzyl) (10Hphenothiazin2yl)amine 417 (4tertButylbenzyl)(10Hphenothiazin2yl)amine 41 8 (2Chlorobenzyl)(lOHphenothiazin2yl)amine 419 (2, 6Difluorobenzyl)(lOHphenothiazin2yl)amine 420 (10HPhenothiazin2yl)(2, 3, 6trifluorobenzyl)amine 421 (2lFluorobenzyl)(lOHphenothiazin2yl)amine 422 (3, 5Dimethoxybenzyl)(10Hphenothiazin2yl)amine 423 Benzyl(10Hphenothiazin2yl)amine 424 (4Methoxybenzyl)(10Hphenothiazin2yl)amine 425 (2, 5Difluorobenzyl)(lOHphenothiazin2yl)amine 426 (lO : HPhenothiazin2yl)(2, 3, 4trifluorobenzyl)amine 427 (2, 3Dihydro1, 4benzodioxin6ylmethyl)(lOHphenothiazin2yl)amine 428 (3Fluoro4methoxybenzyl) (10Hphenothiazin2yl)amine 429 (2, 5Dimethylobenzyl)(10Hphenothiazin2yl)amine 430 (lOHPhenothiazin2yl)thiophen3ylmethylamine 431 (lOHPhenothiazin2yl)(2trifluoromethylbenzyl)amine 432 (9HCarbazol3yl) (3fluoro2methylbenzyl)amine 433 (9HCarbazol3yl)(2methylbenzyl)amine 434 (9HCarbazol3yl) (2, 4dimethylbenzyl)amine 435 (4tertButylbenzyl) (9Hcarbazol3yl)amine 436 (9HCarbazol3yl) (2chlorobenzyl)amine 437 (9HCarbazol3yl) (2, 6difluorobenzyl)amine 438 (9HCarbazol3yl)(2, 3, 6trifluorobenzyl)amine 439 (9HCarbazol3yl) (3, 5dimethoxybenzyl)amine 440 (9HCarbazol3yl) (2, 3dimethoxybenzyl)amine' 441 (9HCarbazol3yl) (2, 5difluorobenzyl)amine 442 (9Hcarbazol3yl)(2, 3, 4trifluorobenzyl)amine 443 (9HCarbazol3yl)(2, 3dihydro1, 4benzodioxin6ylmethyl)amine 444 (9HCarbazol3yl) (2, 5dimethylbenzyl)amine 445 (9HCarbazol3yl)naphthalen1ylmethylamine 446 (9HCarbazol3yl)naphthalen2ylmethylamine 447 Dibenzofuran2ylbis (2, 3dihydrobenzo [1, 4] dioxin6ylmethyl)amine 448 Dibenzofuran2ylbisthiophen3ylmethylamine 449 Dibenzofuran2yl (4phenoxybenzyl)amine 450 2Dibenzofuran2yl2, 3dihydroIHisoindole 451 2Dibenzofiran2yl lH~isoindole1, 3dione 452 Dibenzofuran2yl (4trifluoromethoxybenzyl)amine 453 Dibenzofuran2yl (2methoxybenzyl)amine 454 Dibenzofuran2yl (3phenoxybenzyl)amine 455 Dibenzofuran2ylmethyl (2methylbenzyl)amine 456 Dibenzofuran2yl (lphenylbutyl)amine 457 Dibenzofuran2ylphenethylamine 458 Dibenzofuran2yl(1phenylethyl)amine.
Description:
TRICYCLIC COMPOUNDS AND METHOD OF TREATING HERPES VIRUS FIELD OF THE INVENTION The present invention relates to compounds possessing antiviral activity against viruses of the herpes family, or a composition containing them. These compounds provide a method for treating herpes viral infections, including condition caused by herpes simplex I such as cold sores, herpes simplex II such as genital herpes, as well as shingles caused by herpes zoster and infections caused by cytomegalovirus, Epstein Barr Virus.

BACKGROUND OF THE INVENTION Various subfamilies of herpes viruses (Herpes viridae) exist : a-herpesvirinae, P-herpesvirinae, y-herpesvirinae and cercopithecing Herpes virus I (B virus) ; some specific viruses are : Herpes simplex virus-1 (HSV-1), Herpes simplex virus-2 (HSV- 2), Cytomegalovirus (CMV), Varicella Zoster virus (VZV), Epstein-Barr virus (EBV), human herpes virus-6 (HHV-6), human herpes virus-7 (EIHV-7), human herpes virus-8 (HHV) as well as others which may not yet be defined.

The incidence of infections by Herpes simplex virus is very high throughout the world. Serological studies showed that herpes viral infections affect a substantial percentage of the population. Reactivation of herpes virus infections may lead to recurrent infections. The risk of severe diseases increases with decreasing immunocompetence of the host. There is a pressing need for improved therapy for treating this disease. Currently, exclusive of vaccines, treatment involves primarily nucleoside drugs such as acyclovir, which target thymidine kinase and suffer from. development of resistance.

SUMMARY OF THE INVENTION The present invention provides a compound of the formula and its pharmaceutically acceptable salts, or the compound and its pharmaceutical composition having useful antiviral activity against viruses of the herpes family. wherein : X = 0, (CH2) m, S SOS SO2, NH, NRs or a chemical bond ; Y = 0, (CH2) m, S, SO, S02, NH, NRg ; Z = N, NH, O, NHR8, NRs, S, SO, SO2; n = an integer of from 0 to 2 ; m = an integer of 1, 2, or 3 ; Ri, R2, R3, R4, R5 independently are hydrogen, halogen, hydroxyl, amino, mono or dialkylamino, cyano, nitro, alkyl groups (1-6 carbon atoms), alkoxy groups (1-6 carbon atoms), CF3, OCF3, aminoalkyl (1-6 carbon atoms), aminoaryl, Oaryl, or a heterocyclic ring having 5-7 atoms with 1-4 hetero atoms of N, O or S ; Ar = phenyl, substituted phenyl, benzoheterocyclic ring, substituted benzoheterocyclic ring, heterocyclic ring, or substituted heterocyclic ring, which have substitutions R6 or R7 ; R6 and R7 are independently hydrogen, alkyl group (1-6 carbon atoms), cycloalkyl (3- 12 carbon atoms), halogen, alkoxy, CF3, aminoalkyl (1-6 carbon atoms), aminoaryl, or a heterocyclic ring of from 5-7 atoms with 1-4 heteroatoms of N, O or S ; R6 and R7 may also form a ring, optionally cycloalkyl or aryl or substituted aryl ; Rs is hydrogen, alkyl (1-6 carbon atoms), cycloalkyl (3-12 carbon atoms), phenyl or substituted phenyl wherein the substituents are as defined above.

The invention also provides for a pharmaceutical composition for the treatment of infection or disease caused by a virus, optionally a Herpes virus which comprises an amount of the compound of Claim 1 sufficient to provide an antivirally effective dosage of the compound of Formula I and a pharmaceutically effective carrier.

The invention also provides for a method of treatment of infection or disease caused by a virus, optionally a Herpes virus which comprises administering to a subject in need of such treatment an effective antivirally dosage of a composition of formula I.

DESCRIPTION OF PREFERRED EMBODIMENTS The present invention pertains to anti viral compounds. Preferred compounds are as follows : One preferred compound is : Another preferred compound is : Another preferred compound is : Another preferred compound is : Another preferred compound is : Another preferred compound is : R3 R X R4 t rtho substituted air vn Another preferred compound is : R\/Rz \R4 I N, Ortho-substituted L vm Ri rus The term"alkyl"means a straight or branched hydrocarbon radical having from 1 to 12 carbon atoms unless otherwise specified and includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, and dodecyl. The alkyl group may be unsubstituted or independently substituted by from 1 to 3 substituents selected from F, Cl, Br, I, OH, NH2, SH, CN, NO2, OCHs, OCH2CH20H, NHCHs, or N (CH3) 2.

The term"cycloalkyl"means a hydrocarbon ring, which contains from 3 to 12 carbon atoms unless otherwise specified, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl. Where possible, the cycloalkyl group may contain double bonds. The cycloalkyl ring may be unsubstituted or substituted by from 1 to 3 substituents selected from alkyl, cycloalkyl, alkoxy, thioalkoxy all as defined herein, hydroxy, thiol, nitro, halogen, amino, formyl, carboxyl, nitrile, -NH-CO-R, -CO-NHR-, -CO2R, -COR, aryl, or heteroaryl wherein alkyl (R), aryl, and heteroaryl are defined as herein.

The term"alkoxy"having 1-6 carbon atoms means a Cl-C6 alkyl-O-group or radical wherein Cl-C6 alkyl has the meaning as defined above. Illustrative examples of a straight or branched alkoxy group or radical having from 1 to 6 carbon atoms, also known as a Cl-C6 alkoxy, include methoxy, ethoxy, 1-propoxy, 2-propoxy, 1- butoxy, 2-butoxy, 2-methyl-1-propoxy, and 1, 1-dimethylethoxy, 1-pentoxy, 2- pentoxy, 3-pentoxy, 2, 2-dimethylpropoxy, 1-hexoxy, 2-hexoxy, 3-hexoxy, and 4- methyl-1-pentoxy.

The term"thioalkoxy"having 1-6 carbon atoms means a Cl-C6 alkyl-S-group or radical wherein Ci-C6 alkyl has the meaning as defined above. Illustrative examples of a straight or branched thioalkoxy group or radical having from 1 to 6 carbon atoms, also known as a Cl-C6 thioalkoxy, include methylthio, ethylthio, 1- propylthio, 2-propylthio, 1-butylthio and 2-butylthio, 1-pentylthio, 2-pentylthio, 3- pentylthio, 2, 2-dimethylpropylthio, 1-hexylthio, 2-hexylthio, 3-hexylthio, and 4- methyl-1-pentylthio.

The term"aryl"means an aromatic carbocyclic ring having from 6 to 10 carbon atoms. Illustrative examples of an aryl group or radical include phenyl, 1- naphthyl, and 2-napthyl. The aryl group may be unsubstituted or independently substituted by from 1 to 3 substituents selected, unless otherwise specified, from F, Cl, Br, I, OH, NH2, SH, CN, NO2, OCH3, OCH2CH20H, NHCH3, or N (CH3) 2.

The term"Oaryl"means an aryl-O-group or radical wherein aryl has the meaning as defined above. Illustrative examples of an Oaryl group or radical include phenoxy, 1-naphthyloxy, and 2-napthyloxy. Oaryl groups may be unsubstituted or independently substituted by from 1 to 3 substituents selected, unless otherwise specified, from F, Cl, Br, I, OH, NH2, SH, CN, NO2, OCH3, OCH2CH20H, NHCH3, or N (CH3) 2.

The term"halogen"means bromine, chlorine, fluorine or iodine.

The term"monoalkylamino"means an NEt-alkyl group or radical wherein alkyl has the meaning as defined abve.

The term "dialkylamino" means an N- (alkyl) 2 group or radical wherein alkyl has the meaning as defined abve.

The term"aminoalkyl"having 1-6 carbon atoms means an H2N- (Cl-C6 alkyl)- group or radical wherein Cl-C6 alkyl has the meaning as defined above. The aminoalkyl group is a substituted Cl-C6 alkyl group or radical containing at least one substituent which is NH2.

The term"aminoaryl"means an H2N-aryl-group or radical wherein aryl has the meaning as defined above. The aminoaryl group is a substituted aryl group or radical containing at least one substituent which is NH2.

The term"carbocycle"means cycloalkyl as defined above.

The term"heteroatom"means a nitrogen, sulfur, or oxygen.

The term"heterocycle"means a heterocyclic radical which are 5-7 atoms having 1-4 heteroatoms and are selected from : furan, pyrrole, thiophene, oxazole, isoxazole, thiazole, pyrazole, 1, 2, 3-triazole, 1, 2, 4-triazole, tetrazole, pyridine, pyridazine, pyrimidine, pyrazin, tetrahydrofuran, tetrahydrothiophene, pyrrolidine, piperazine, piperidine, morpholine, thiomorpholine, oxolane, dioxane, sulfolan, unsubstituted or substituted by 1 to 2 substituents selected from alkyl as defined above. For heterocycles containing sulfur, the oxidized sulfur heterocycles containing SO or SO2 groups are also included.

The term"benzoheterocyclic ring" ("fused heterocycle") refers to a heterocycle that is adjoined at two consecutive positions with a phenyl ring or another heterocycle. such rings may include 2-, 3-, 4-, 5-, 6-, 7-, or 8-quinolinyl, 1-, 3-, 4-, 5-, 6-, 7-, or 8-isoquinolinyl, 2-, 3-, 4-, 5-, 6-, or 7-indolyl, 2-, 3-, 4-, 5-, 6-, or 7-benzo [b] thienyl, 2-, 4-, 5-, 6-, or 7-benzoxazolyl, 2-, 4-, 5-, 6-, or 7-benzimidazolyl, 2-, 4-, 5-, 6-, or 7-benzothiazolyl.

Some of the compounds of Formula I are capable of further forming pharmaceutically acceptable acid-addition and/or base salts. All of these forms are within the scope of the present invention.

Pharmaceutically acceptable acid addition salts of the compounds of Formula I include salts derived from nontoxic inorganic acids such as hydrochloric, nitric, phosphoric, sulfuric, hydrobromic, hydriodic, hydrofluoric, phosphorous, and the like, as well as the salts derived from nontoxic organic acids, such as aliphatic mono-and dicarboxylic acids, phenyl-substituted alkanoic acids, hydroxy alkanoic acids, alkanedioic acids, aromatic acids, aliphatic and aromatic sulfonic acids, etc. Such salts thus include sulfate, pyrosulfate, bisulfate, sulfite, bisulfite, nitrate, phosphate, monohydrogenphosphate, dihyrogenphosphate, metaphosphate, pyrophosphate, chloride, bromide, iodide, acetate, trifluoroacetate, propionate, caprylate, isobutyrate, oxalate, malonate, succinates suberate, sebacate, fumarate, maleate, mandelate, benzoate, chlorobenzoate, methylbenzoate, dinitrobenzoate, phthalate, benzenesulfonate, toluenesulfonate, phenylacetate, citrate, lactate, maleate, tartrate, methanesulfonate, and the like. Also contemplated are salts of amino acids such as arginate and the like and gluconate, galacturonate (see, for example, Berge S. M., et al.,"Pharmaceutical Salts,"Journal of Phclrmaceulrical Science, 1977 ; 66 : 1-19.

The acid addition salt of said basic compounds are prepared by contacting the free base form with a sufficient amount of the desired acid to produce the salt in the conventional manner.

Pharmaceutically acceptable base addition salts are formed with metals or amines, such as alkali and alkaline earth metals or organic amines. Examples of metals used as cations are sodium, potassium, magnesium, calcium, and the like.

Examples of suitable amines are N, N'-dibenzylethylenediamine, chloroprocaine, choline, diethanolamine, dicyclohexylamine, ethylenediamine, N-methylglucamine, and procaine (see, for example, Berge, supra., 1977).

The base addition salts of said acidic compounds are prepared by contacting the free acid form with a sufficient amount of the desired base to produce the salt in the conventional manner.

Certain of the compounds of the present invention can exist in unsolvated forms as well as solvated forms, including hydrated forms. In general, the solvated forms, including hydrated forms, are equivalent to unsolvated forms and are intended to be encompassed within the scope of the present invention.

Certain of the compounds of the present invention possess one or more chiral centers and each center may exist in the R (D) or S (L) configuration. The present invention includes all enantiomeric and epimeric forms as well as the appropriate mixtures thereof. Configuration drawn is most preferred.

The compounds of the present invention can be prepared and administered in a wide variety of oral and parenteral dosage forms. Thus, the compounds of the present invention can be administered by injection, that is, intravenously, intramuscularly, intracutaneously, subcutaneously, intraduodenally, or intraperitoneally. Also, the compounds of the present invention can be administered by inhalation, for example, intranasally. Additionally, the compounds of the present invention can be administered transdermally. It will be obvious to those skilled in the art that the following dosage forms may comprise as the active component, either a compound of Formula I or a corresponding pharmaceutically acceptable salt of a compound of Formula I For preparing pharmaceutical compositions from the compounds of the present invention, pharmaceutically acceptable carriers can be either solid or liquid.

Solid form preparations include powders, tablets, pills, capsules, cachets, suppositories, and dispersible granules. A solid carrier can be one or more substances, which may also act as diluents, flavoring agents, binders, preservatives, tablet disintegrating agents, or an encapsulating material.

In powders, the carrier is a finely divided solid, which is in a mixture with the finely divided active component.

In tablets, the active component is mixed with the carrier having the necessary binding properties in suitable proportions and compacted in the shape and size desired.

The powders and tablets preferably contain from five or ten to about seventy percent of the active compound. Suitable carriers are magnesium carbonate, magnesium stearate, talc, sugar, lactose, pectin, dextrin, starch, gelatin, tragacanth, methylcellulose, sodium carboxymethylcellulose, a low melting wax, cocoa butter, and the like. The term"preparation"is intended to include the formulation of the active compound with encapsulating material as a carrier providing a capsule in which the active component with or without other carriers, is surrounded by a carrier, which is thus in association with it. Similarly, cachets and lozenges are included. Tablets, powders, capsules, pills, cachets, and lozenges can be used as solid dosage forms suitable for oral administration.

For preparing suppositories, a low melting wax, such as a mixture of fatty acid glycerides or cocoa butter, is first melted, and the active component is dispersed homogeneously therein, as by stirring. The molten homogenous mixture is then poured into convenient sized molds, allowed to cool, and thereby to solidify.

Liquid form preparations include solutions, suspensions, and emulsions, for example, water or water propylene glycol solutions. For parenteral injection, liquid preparations can be formulated in solution in aqueous polyethylene glycol solution.

Aqueous solutions suitable for oral use can be prepared by dissolving the active component in water and adding suitable colorants, flavors, stabilizing and thickening agents as desired.

Aqueous suspensions suitable for oral use can be made by dispersing the finely divided active component in water with viscous material, such as natural or, synthetic gums, resins, methylcellulose, sodium carboxymethylcellulose, and other well-known suspending agents.

Also included are solid form preparations, which are intended to be converted, shortly before use, to liquid form preparations for oral administration. Such liquid forms include solutions, suspensions, and emulsions. These preparations may contain, in addition to the active component, colorants, flavors, stabilizers, buffers, artificial and natural sweeteners, dispersants, thickeners, solubilizing agents, and the like.

The pharmaceutical preparation is preferably in unit dosage form. In such form the preparation is divided into unit doses containing appropriate quantities of the active component. The unit dosage form can be a packaged preparation, the package containing discrete quantities of preparation, such as packeted tablets, capsules, and powders in vials or ampoules. Also, the unit dosage form can be a capsule, tablet, cachet, or lozenge itself, or it can be the appropriate number of any of these in packaged form.

The quantity of active component in a unit dose preparation may be varied or adjusted from 0. 1 mg to 100 mg preferably 0. 5 mg to 100 mg according to the particular application and the potency of the active component. The composition can, if desired, also contain other compatible therapeutic agents.

In therapeutic use as antagonists of a virus, as agents for the treatment of infections caused by a virus or as agents for the treatment of diseases due to a virus, the compounds utilized in the pharmaceutical method of this invention are administered at the initial dosage of about 0. 01 mg to about 100 mg/kg daily. A daily dose range of about 0. 01-mg to about 10 mg/kg is preferred. The dosages, however, may be varied depending upon the requirements of the patient, the severity of the condition being treated, the compound being employed. Determination of the proper dosage for a particular situation is within the skill of the art. Generally, treatment is initiated with smaller dosages, which are less than the optimum dose of the compound. Thereafter, the dosage is increased by small increments until the optimum effect under the circumstances is reached. For convenience, the total daily dosage may be divided and administered in portions during the day, if desired.

General procedure 1 (for Singleton synthesis) : Reductive amination of aryl amines with aldehydes or ketones.

Reagent 2 (1 eq.) was taken in a solvent (dichloromethane, 1, 2-dichloroethane or tetrahydrofuran or diethyl ether) and to it reagent 1 (1 to 1. 2 eq.) was added. To this solution cooled at 0°C was added a reducing agent (sodium cyanoborohydride or sodium triacetoxyborohydride) (1 to 2 eq.). To it a drop of acetic acid was added and kept under stirring at room temperature for 6 to 24 hours. The excess hydride was quenched by adding methanol. The reaction mixture was diluted with ethyl acetate and washed with saturated ammonium chloride solution, aqueous sodium bisulfite and brine ; dried over anhydrous magnesium sulfate or sodium sulphate. Organic layer was concentrated and crude product was purified by flash silica gel chromatography to afford the final product. The products were characterized by spectral data. The compounds synthesized using this procedure are shown in Table 4.

General procedure 2 for multiple, simultaneous solution phase synthesis (combinatorial chemistry synthesis) : To a 2-dram glass vial were added, by Tecan liquid handling robot, a solution of reagent 2 (0. 05mmol) in trimethyl orthoformate (0. 2ml) followed by reagent 1 (0. 05mmol) in trimethyl orthoformate (0. 2ml). The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight), then concentrated to dryness. To each vial was added, by Tecan liquid handling robot, 1, 2- dichloroethane (lml). Solid sodium triacetoxyborohydride (-23mg) was added manually to each vial. A a solution of acetic acid (0. 05mmol) in dichloroethane (0. 05ml) was added to each vial by Tecan liquid handling robot. The vial was again capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan liquid handling robot, methanol (lml). The reaction mixture was then transferred, by Tecan liquid handling robot, to be prewashed (That is washed with methanol (2ml) and dichloroethane (lml)) BAKERBOND speTM Aromatic Sulfonic Acid (S03H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2xlml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3xlml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromotography mass spec).

General procedure 3 for multiple, simultaneous solution phase synthesis (combinatorial Chemistry synthesis) : To a 2-dram glass vial were added, by TecanTM liquid handling robot, a solution of reagent 2 (0. 05mmol) inN, N-dimethylformamide (0. lml) followed by reagent 1 (0. 05mmol) in N, N-dimethylformamide (0. lml). Each vial was treated with trimethylorthoformate (0. 2ml) by Tecan liquid handling robot. The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight), then concentrated to dryness. To each vial was added, by Tecan liquid handling robot, 1, 2-dichloroethane (lml). Solid sodium triacetoxyborohydride (-23mg) was added manually to each vial. A solution of acetic acid (0. 05mmol) in 1, 2- dichloroethane (0. 05ml) was added to each vial by Tecan liquid handling robot.

The vial was again capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan liquid handling robot, methanol (lml). The reaction mixture was then transferred, by TecanTM liquid handling robot, to be prewashed (That is washed with methanol (2ml) and 1, 2-dichloroethane (lml)) BAKERBOND sperm Aromatic Sulfonic Acid (S03H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2xlml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3xlml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).

General procedure 4 for multiple, simultaneous solution phase synthesis (combinatorial Chemistry synthesis)- To a 2-dram glass vial were added, by Tecan liquid handling robot, a solution of reagent 2 (0. 05mmol) in methanol (0. 2ml) followed by reagent 1 (0. 2mmol) in methanol (0. 2ml). To each vial was added, by Tecan liquid handling robot, a 1N solution of sodium cyanoborohydride in methanol (0. 2ml) and a 10% acetic acid in methanol (0. 05ml) solution. The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight), then concentrated to dryness. The vial was again capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan liquid handling robot, methanol (1ml). The reaction mixture was then transferred, by Tecan liquid handling robot, to be prewashed (That is washed with methanol (2ml) and 1, 2- dichloroethane (lml)) BAKERBOND speTM Aromatic Sulfonic Acid (SOsH) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2xlml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3xlml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).

General procedure 5 for multiple, simultaneous solution phase synthesis (combinatorial Chemistry synthesis) : To a 2-dram glass vial were added, by Tecan liquid handling robot, a solution of reagent 2 (0. 05mmol) in 1, 2-dichloroethane (0. 2ml) followed by reagent 1 (0. 15mmol) in 1, 2-dichloroethane (0. lml). To each vial solid sodium triacetoxyborohydride (-25mg) was added manually. A solution of acetic acid (0. 05mmol) in 1, 2-dichloroethane (0. 05ml) was added to each vial by TecanTM liquid handling robot. The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan liquid handling robot, methanol (lml). The reaction mixture was then transferred, by Tecan liquid handling robot, to be prewashed (washed with methanol (2ml) and 1, 2-dichloroethane (lml)) BAKERBOND speT"4 Aromatic Sulfonic Acid (S03H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2xlml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3xlml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).

General procedure 6 for multiple, simultaneous solution phase synthesis (combinatorial Chemistry synthesis) : To a 2-dram glass vial were added, by Tecan liquid handling robot, a solution of reagent 2 (0. 05mmol) in methanol (0. 2ml) followed by reagent 1 (0. 15mmol) in methanol (0. lml). To each vial was added a 1N solution of sodium cyanoborohydride in methanol (0. lml) and a 10% acetic acid in methanol solution (0. 05ml). The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by TecanTM liquid handling robot, methanol (1ml). The reaction mixture was then transferred, by Tecan liquid handling robot, to be prewashed (washed with methanol (2ml) and 1, 2-dichloroethane (lml)) BAKERBOND sperm Aromatic Sulfonic Acid (S03H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2xlml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3xlml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).

General procedure 7 for multiple, simultaneous solution phase synthesis (combinatorial Chemistry synthesis) : To a 2-dram glass vial were added, by TecanTM liquid handling robot, a solution of reagent 2 (0. 05mmol) followed by reagent 1 in N, N-dimethylformamide (0. 32ml) or methanol (0. 2ml). The vials were then concentrated overnight to dryness. Each vial was treated by Tecan liquid handling robot with reagent 1 (0. 15mmol) in methanol (O. lml) and methanol (0. 2ml). To each vial was added a IN solution of sodium cyanoborohydride in methanol (0. lml) and a 10% acetic acid in methanol solution (0. 05ml). The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by TecanTM liquid handling robot, methanol (lml). The reaction mixture was then transferred, by Tecan liquid handling robot, to be prewashed (washed with methanol (2ml) and 1, 2-dichloroethane (1m1)) BAKERBOND sperm Aromatic Sulfonic Acid (S03H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2xlml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3xlml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).

Synthesis of Compound 450 : To dibenzofuran-2-yl-amine (0. 91 g, 5 mmol) taken in dichloromethane (75 mL) was added a, a'-dibromo-ortho-xylene (1. 85 g, 7 mmol) followed by triethylamine (3. 03 g, 30 mmol). The reaction was stirred at room temperature for 24 hours. The solvents were evaporated and the residue was purified by flash silica gel chromatography to give the title compound (1. 43 g).

Synthesis of Compound 451 : To dibenzofuran-2-yl-amine (0. 91 g, 5 mmol) taken in dichloromethane (75 mL) was added phthaloyl dichloride (1. 16 g, 6 mmol) followed by triethylamine (3. 03 g, 30 mmol). The reaction was stirred at room temperature for 5 minutes. The reaction was quenched with sodium bicarbonate solution and the organic layer was separated. The crude product was purified by flash silica gel chromatography to give the title compound (0. 51 g).

Synthesis of Compound 463 : To compound 58 (0. 25 g, 0. 87 mmol) taken in tetrahydrofuran (10 mL) was added sodium hydride (60% in mineral oil, 0. 035 g, 0. 87 mmol). To it methyl iodide (0. 25 g, 1. 74 mmol) was added. The reaction was stirred at room temperature for 24 hours. The solvents were evaporated and the residue was purified by flash silica gel chromatography to give the title compound (0. 18 g).

Deprotection of t-butyloxycarbonyl group : The general procedure for the removal of tert-butyoxycarbonyl (Boc) group is as follows : To the compound taken a flask was added hydrochloric acid in an appropriate solvent (dioxane, methanol, 1, 2- dichloromethane and the reaction was kept under shaking for 5 to 18 hours. Removal of volatiles furnished the corresponding product.

Reagents 1 are shown in Table 1.

Table 1 : Aldehydes/ketones (reagent 1) No. Reagent 1 (aldehydes/lçetones) 1 o-tolualdehyde 2 meta-tolualdehyde 3 para-tolualdehyde 4 2-fluorobenzaldehyde 5 3-flúorobenzaldehyde 6 4-fluorobenzaldehyde 7 4-tert-butylbenzaldehyde 8 a, a, a-Trilfluoro-o-tolualdehyde <BR> <BR> <BR> <BR> 9 oe Trilfluoro-m-tolualdehyde<BR> <BR> <BR> <BR> <BR> <BR> <BR> 10 a, a, a-Trilfluoro-p-tolualdehyde<BR> <BR> <BR> <BR> <BR> <BR> 11 o-anisaldehyde 12 m-anisaldehyde 13 p-anisaldehyde 14 Salicylaldehyde 15 3-hydroxybenzaldehyde 16 4-hydroxybenzaldehyde 17 2-chlorobenzaldehyde 18 3-chlorobenzaldehyde 19 4-chlorobenzaldehyde 20 3-benzyloxybenzaldehyde 21 4-benzyloxybenzaldehyde 22 2, 3-dimethoxybenzaldehyde 23 2, 4-dimethoxybenzaldehyde 24 2, 5-dimethoxybenzaldehyde 25 2, 6-dimethoxybenzaldehyde 26 3, 4-dimethoxybenzaldehyde 27 3, 5-dimethoxybenzaldehyde 28 1, 4-Benzodioxan-6-carboxaldehyde 29 2, 4-dimethylbenzaldehyde 30 2, 5-dimethylbenzaldehyde 31 2, 3-difluorobenzaldehyde 32 2, 4-difluorobenzaldehyde 33 2, 5-difluorobenzaldehyde 34 2, 6-difluorobenzaldehyde 35 3, 4-difluorobenzaldehyde 35 3, 5-difluorobenzaldehyde 37 2, 3, 4-trifluorobenzaldehyde 38 2, 3, 6-trifluorobenzaldehyde 39 3-fluoro-2-methylbenzaldehyde 40 3-fluoro-p-anisaldehyde 41 2-pyridinecarboxaldehyde 42 3-pyridinecarboxaldehyde 43 4-pyridinecarboxaldehyde 44 4-pyridinecarboxaldehyde N-oxide <BR> <BR> 45 6-methyl-2-pyridinecarboixaldehyde 46 3-furaldehyde 47 2-furaldehyde <BR> <BR> 48 5-chloro-2-thiophenecarboxaldehyde<BR> <BR> 49 3-thiophenecarboxaldehyde<BR> <BR> 50 2-thiophenecarboxaldehyde<BR> <BR> 51 pyrrole-2-carboxaldehyde<BR> <BR> 52 1-methyl-2-pyrrolecarboxaldehyde<BR> <BR> 53 1-naphthaldehyde<BR> <BR> 54 2-naphthaldehyde<BR> <BR> 55 2-quinolinecarboxaldehyde 56 3-quinolinecarboxaldehyde <BR> <BR> 57 4-quinolinecarboxaldehyde<BR> <BR> 58 indole-3-carboxaldehyde 59 2-bromobenzaldehyde 60 2-chlorobenzaldehyde 61 2-ethoxybenzaldehyde 62 2-cyanobenzaldehyde 635- (2-chlorophenyl) furfural <BR> <BR> 64 5- (3-chlorophenyl) furfural<BR> <BR> 65 5- (4-chlorophenyl) furfural 66 2-thiazolecarboxaldehyde 67 2-imidazolecarboxaldehyde 68 4 (5)-imidazolecaboxaldehyde 69 5-nitro-2-thiophenecarboxaldehyde 70 2-nitrobenzaldehyde 71 4-formyluracil 72 4-acetoxybenzaldehyde 73 4-(dimethylamino) benzaldehyde <BR> <BR> 74 1-acetyl-3-indolecarboxaldehyde<BR> <BR> 75 4-bromo-2-thiophenecarboxaldehyde 76 Piperonal 77 3-trifluoromethoxybenzaldehyde 78 4-chloro-3-nitro-benzaldehyde 79 Benzaldehyde 80 3-benzyloxybenzaldehyde <BR> <BR> 81 3-phenoxybenzaldehyde<BR> 822-butanone' 83 2-Pentanone <BR> <BR> 84 3-Methyl-2-butanone<BR> <BR> 85 Tetrahydrothiophene-3-one 86 Tetrahydrothiopyran-4-one 87 Cycloheptanone 88 Cyclooctanone 89 Cyclohexylmethylketone 90 4-Methyl-2-pentanone 91 3-Pentanone 92 3-Hexanone 93 4-Hydroxy-3-methyl-2-butanon 94 2-Methoxyphenylacetone 95 4-nitrobenzaldehyde 96 4- (methylthio) benzaldehyde 97 Propionaldehyde 98 Isovaleraldehyde 99 3-(methylthio) propionaldehyde 100 1-phenyl-2-pentanone 101 Acetone.

102 Cyclopropyl methyl ketone 103 Cyclohexanone 104 n-tert-butoxycarbonyl-4-piperidone 105 3, 3, 5, 5-tetramethylcyclohexanone 106 1-decalone 107 4-cyclohexylcyclohexanone 108 2-norbornanone<BR> 109 4-tert-butylcyclohexanone 110 Cyclopentanone 111 2-adamantanone 112 Bicyclo [3, 2, 1] octan-2-one 113 1, 1-dioxo-tetrahydro-thiopyran-4-one Reagent 2 (amines) used in the above general procedures are shown in Table 2 : Table 2 : No. Reagent 2 (amines) 1 Dibenzofuran-2-yl-methyl-amine<BR> 2 8-fluoro-dibenzofuran-2-yl-amine 3 8-chloro-dibenzofuran-2-yl-amine 4 8-amino-dibenzofuran-2-ol<BR> 5 3-methoxy-diebenzofuran-2-yl-amine 6 9H-Fluoren-3-yl-amine 7 9H-Fluorene-2-yl-amine<BR> 8 Dibenzofuran-4-yl-amine 9 Benzo [4, 5] furo [2, 3-H]pyridin-3-yl-amine 10 9-Ethyl-9H-carbazol-3-ylamine 11 3-Amino-carbazole-9-carboxylic acid tert-butyl ester 12 Dibenzofuran-2-yl-methyl-amine 13 Dibenzofuran-2-yl-dimethyl-amine<BR> 14 Dibenzothiophene-2-yl-amine 15 Dibenzothiophene-3-yl-amine 16 6-Amino-1, 2, 3, 4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester 17 Dibenzo [1, 4] dioxin-2-yl-amine 18 Phenoxanthiin-3-yl-amine 19 10-Oxa-9-thia-l-aza-anthracen-3-yl-amine 20 10H-Benzo-b] pyrido [2, 3-e] [1, 4] oxazin-3-ylamine acetic acid, tert-butyl ester 21 Anthracen-2-yl-amine 22 10, 11 1-Dihydro-5H-diebnzo [b, fazepin-3-yl-amine 23 6, 7, 8, 9-Tetrahydro-5H-carbazol-3-yl-amine 24 7-Amino-1-aza-phenoxathiin The compounds of Formula I include : (1-Cyclopropyl-ethyl)-(2-methoxy-dibenzofilran-3-yl)-amine 2 Cyclopentyl- (9H-fluoren-2-yl)-amine 3 (1-Cyclopropyl-ethyl)- (9H-fluoren-2-yl)-amine 4 N3-Cyclopentyl-N2, N2-dimethyl-9H-fluorene-2, 3-diamine 5 Isopropyl-(2-methoxy-dibenzofuran-3-yl)-amine 6 (2-Methoxy-dibenzofuran-3-yl)- (tetrahydro-thiopyran-4-yl)-amine 7 Cycloheptyl- (2-methoxy-dibenzofuran-3-yl)-amine 8 (1-Ethyl-propyl)-(2-methoxy-dibenzofuran-3-yl)-amine 9 sec-Butyl- (2-methoxy-dibenzofuran-3-yl)-amine 10 N2, N2-Dimethyl-N3-piperidin-4-yl-9H-fluorene-2, 3-diamine 11 N3-(1-Benzyl-butyl)-N2,N2-dimethyl-9H-fluorene-2, 3-diamine 12 (9H-Fluoren-2-yl)-piperidin-4-yl-amine<BR> 13 (1-Benzyl-butyl)- (9H-fluoren-2-yl)-amine 14 sec-Butyl- (9H-fluoren-2-yl)-amine 15 (1, 1-Dioxo-hexahydro-thiopyran-4-yl)-(2-methoxy-dibenzofuran-3- yl)-amine 16 Dibenzofuran-2-yl- (3, 3, 5, 5-tetramethyl-cyclohexyl)-amine 17 (Decahydro-naphthalen-1-yl)-dibenzofuran-2-yl-amine 1 8 Adamantan-2-yl-dibenzofuran-2-yl-amine 19 Bicyclohexyl-4-yl-dibenzofuran-2-yl-amine 20 Bicyclo [2. 2. 1] hept-2-yl-dibenzofuran-2-yl-amine 21 (4-tert-Butyl-cyclohexyl)-dibenzofuran-2-yl-amine 22 Bicyclo [3. 2. l] oct-2-yl-dibenzofuran-2-yl-amine 23 Cyclopentyl-dibenzofuran-2-yl-amine 24Cyclohexyl- (2-methoxy-dibenzofuran-3-yl)-amine 25 Cyclohexyl- (9H-fluoren-2-yl)-amine <BR> <BR> <BR> <BR> 26 Dibenzofuran-2-yl-bis- (3-methylsulfanyl-propyl)-amine<BR> <BR> <BR> <BR> <BR> <BR> <BR> 27 Dibenzofuran-2-yl-bis- (3-methyl-butyl)-amine 28 Dibenzofuran-2-yl-dipropyl-amine 29 N3- (l, 1-Dioxo-hexahydro-thiopyran-4-yl)-N2, N2-dimethyl-9H-fluorene-2, 3- diamine 30 N3-Isopropyl-N2, N2-dimethyl-9H-fluorene-2, 3-diamine 31 N2, N2-Dimethyl-N3-(tetrahydro-thiopyran-4-yl)-9H-fluorene-2, 3-diamine 32 N3-Cyclohexyl-N2, N2-dimethyl-9H-fluorene-2, 3-diamine 33 N3-Cycloheptyl-N2, N2-dimethyl-9H-fluorene-2, 3-diamine 34 N3- (1-Ethyl-propyl)-N2, N2-dimethyl-9H-fluorene-2, 3-diamine 35 N3-(l-Cyclopropyl-ethyl)-N2, N2-dimethyl-9H-fluorene-2, 3-diamine 36 N3-sec-Butyl-N2,N2-dimethyl-9H-fluorene-2, 3-diamine 37 (9H-Fluoren-2-yl)-isopropyl-amine 38 (9H-Fluoren-2-yl)- (tetrahydro-thiopyran-4-yl)-amine 39 Cycloheptyl- (9H-fluoren-2-yl)-amine 40 Dibenzofuran-2-yl- (l, 1-dioxo-hexahydro-thiopyran-4-yl)-amine 41 Dibenzofuran-2-yl-piperidin-4-yl-amine 42 Dibenzofuran-2-yl-isopropyl-amine 43 Cyclohexyl-dibenzofuran-2-yl-amine 44 (1-Cyclopropyl-ethyl)-dibenzofuran-2-yl-amine 45 Dibenzofuran-3-yl- (1, 1-dioxo-hexahydro-thiopyran-4-yl)-amine 46 Dibenzofuran-3-yl-piperidin-4-yl-amine 47 Dibenzofuran-3-yl-isopropyl-amine 48Dibenzofuran-3-yl- (tetrahydro-thiopyran-4-yl)-amine <BR> <BR> <BR> <BR> 49 Cyclohexyl-dibenzofuran-3-yl-amine<BR> <BR> <BR> <BR> <BR> <BR> 50 Cycloheptyl-dibenzofuran-3-yl-amine 51 (4-Chloro-benzyl)-dibenzofuran-2-yl-amine 52 (4-Chloro-3-nitro-benzyl)-dibenzofuran-2-yl-amine 53 Dibenzofuran-2-yl- (3-trifluoromethoxy-benzyl)-amine 54 Benzo [1, 3] dioxol-5-ylmethyl-dibenzofuran-2-yl-amine 55 Dibenzofuran-2-yl- (2, 3-dihydro-benzofl, 4] dioxin-6-ylmethyl)-amine 56 Dibenzofuran-2-yl- (3, 5-dimethoxy-benzyl)-amine 57 Dibenzofuran-2-yl- (4-trifluoromethyl-benzyl)-amine 58 Dibenzofuran-2-yl- (2-methyl-benzyl)-amine <BR> <BR> <BR> <BR> 59 Dibenzofuran-2-yl-thiophen-3-ylmethyl-amine<BR> <BR> <BR> <BR> <BR> 60 Dibenzofuran-2-yl- (4-nitro-benzyl)-amine 61 Dibenzofuran-2-yl- (4-methylsulfanyl-benzyl)-amine <BR> <BR> <BR> <BR> 62 Dibenzofuran-2-yl- (4-methyl-benzyl)-amine<BR> <BR> <BR> <BR> <BR> <BR> 63 Benzyl-dibenzofuran-2-yl-amine 64 (3-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine 65 (1-Benzyl-butyl)-dibenzofuran-2-yl-amine <BR> <BR> <BR> <BR> 66 Dibenzofuran-2-yl-[2-(2-methoxy-phenyl)-1-methyl-ethyl]-amin e<BR> <BR> <BR> <BR> <BR> <BR> 67 3-(Dibenzofuran-2-ylamino)-2-methyl-butan-1-ol 68 Dibenzofuran-2-yl- (1-ethyl-butyl)-amine 69 Dibenzofuran-2-yl- (1-ethyl-propyl)-amine 70 Dibenzofuran-2-yl- (1, 3-dimethyl-butyl)-amine 71 (1-Cyclohexyl-ethyl)-dibenzofuran-2-yl-amine 72 Cyclooctyl-dibenzofuran-2-yl-amine <BR> <BR> <BR> <BR> 73 Cycloheptyl-dibenzofuran-2-yl-amine<BR> <BR> <BR> <BR> <BR> 74 Dibenzofuran-2-yl- (tetrahydro-thiopyran-4-yl)-amine 75 Dibenzofuran-2-yl- (tetrahydro-thiophen-3-yl)-amine 76 Dibenzofuran-2-yl- (1, 2-dimethyl-propyl)-amine 77 Dibenzofilran-2-yl-(1-methyl-butyl)-amine 78 sec-Butyl-dibenzofuran-2-yl-amine 79 Benzofurp [3, 2-b] pyridin-8-yl- (2-fluoro-benzyl)-amine 80 Benzofuro [3, 3-b] pyridin-8-yl-pyridin-4-ylmethyl-amine 81 Benzofuro [3, 2-b] pyridin-8-yl- (2-methyl-benzyl)-amine 82 N- (2-Fluoro-benzyl)-N'-methyl-dibenzofuran-2, 8-diamine 83 N-Methyl-N'-quinolin-4-ylmethyl-dibenzofuran-2, 8-diamine 84 N-Methyl-N'-naphthanlen-1-ylmethyl-dibenzofuran-2, 8-diamine 85 N- (4-Methanesulfonyl-benzyl)-N'-methyl-diebnzofuran-2, 8-diamine 86 N-Methyl-N'-pyridin-4-ylmethyl-dibensofuran-2, 8-diamine 87 N-Methyl-N'- (2-methyl-benzyl)-dibenzofuran-2, 8-diamine 88 Naphthanlen-1-ylmethyl-(1 01EI-phenothiazin-2-yl)-amine 89 (4-Methanesulfonyl-benzyl)- (10H-phenothiazin-2-yl)-amine 90 (3-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6- yl)-amine 91 (2-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6- yl)-amine 92 (10-Oxa-9-thia-1-aza-anthracen-6-yl)-qinolin-4-ylmethyl-amin e 93 Naphthalene-1-ylmethyl-(10-oxa-9-thia-1-aza-anthracen-6-yl)- amine 94 (4-Methanesulfonyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6- yl)-amine 95 (10-Oxa-9-thia-1-aza-anthracen-6-yl)-pyridin-4-ylmethyl-amin e 96 (2-Methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine <BR> <BR> 97 Anthracen-2-yl-quinolin-4-ylmethyl-amine<BR> <BR> 98 Anthracen-2-yl- (4-methanesulfonyl-benzyl)-amine<BR> <BR> 99 Anthracen-2-yl-pyridin-4-ylmethyl-amine 100Anthracen-2-yl- (2-methyl-benzyl)-amine 1 01 Dibenzo [b, e] [1, 4]-dioxin-2-yl- (2-fluoro-benzyl)-amine 102 Dibenzo [b, e] [1, 4] dioxin-2-yl- (2-fluoro-benzyl)-amine 103 Dibenzo [b, e] [1, 4] fioxin-2-yl-quinolin-4-ylmethyl-amine 104Dibenzo [b, e] [1, 4] fioxin-2-yl-naphthalen-1-ylmethyl-amine 105 Dibenzo [b, e] [1, 4] fioxin-2-yl- (4-methanesulfonyl-benzyl)-amine 106 Dibenzo [b, e] [1, 4] fioxin-2-yl-pyridin-4-ylmethyl-amine <BR> <BR> 1078- (3-Pluoro-2-methyl-benzylamino)-dibenzofuran-2-ol<BR> <BR> 1 08 8-(2-liluoro-benzylamino)-dibenzofuran2-ol<BR> <BR> 1 09 8-(4-Methanesulfonyl-benzylamino)-dibenzoiran-2-ol<BR> <BR> 110 8- [ (Pyridin-4-ylmethyl)-amino]-dibenzofuran-2-ol 111 8- (2-Methyl-benzylamino)-dibenzofuran-2-ol 112 (8-Chloro-dibenzofuran-2-yl)- (2-fluoro-benzyl)-amine 113 8-Chloro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine 114 8-Chloro-dibenzofuran-2-yl)- (4-methanesulfonyl-benzyl)-amine 115 (4-Methanesulfonyl-benzyl)-(6, 7, 8, 9-tetrahydro-5H-carbazol-3-yl)-amine 116 Pyridin-4-ylmethyl- (6, 7, 8, 9-tetrahydro-5H-carbazol-3-yl)-amine 117 Benzofuro [3, 2-b] pyridin-8-yl- (3-fluoro-2-methyl-benzyl)-amine 118 Dibenzofuran-2-yl-quinolin-4-ylmethyl-amine <BR> <BR> 119 Dibenzofuran-2-yl-quinolin-2-ylmethyl-amine<BR> <BR> 120 (4-Dimethylamino-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine<BR> <BR> 121 Dibenzofuran-2-yl-(4-dimethylamino-benzyl)-amine<BR> <BR> 122 Diebnzofuran-2-yl- (5-nitro-thiophen-2-ylmethyl)-amine 123 Dibenzofuran-2-yl-thiazol-2-ylmethyl-amine<BR> <BR> 124 Benzyl- (8-fluoro-dibenzofuran-2-yl)-amine 125 N- (-3-Methoxybenzyl)-N'-methyl-dibenzofuran-2, 8-diamine 126 N- (3, 5-Dimethoxy-benzyl)-N'-methyl-dibenzofuran-2, 8-diamine 127 N- (4-tert-Butyl-benzyl)-N'-methyl-dibenzofuran-2, 8-diamine 128 N-Benzyl-N'-methyl-dibenzofuran-2, 8-diamine <BR> <BR> 129 2- [ (8-Methylamino-dibenzofuran-2-ylamino)-methyl]-benzonitrile& lt;BR> <BR> 130 (4-Methoxy-benzyl)-phenoxathiin-3-yl-amine 131 (8-Chloro-dibenzofuran-2-yl)- (3-methoxy-benzyl)-amine 132 (3-Methoxy-benzyl)-phenoxathiin-3-yl-amine 133 (3, 5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine <BR> <BR> 134 (3-Fluoro-4-methoxy-benzyl)-phenoxathiin-3-yl-amine<BR> ; <BR> 135 (4-tert-Butyl-benzyl)-phenoxathiin-3-yl-amine 136 Benzyl-phenoxathiin-3-yl-amine 137 (2-Ethoxy-benzyl)-phenoxathiin-3-yl-amine 138 (8-Chloro-dibenzoCuran-2-yl)- (3, 5-dimethoxy-benzyl)-amine 139 (8-Chloro-dibenzofuran-2-yl)- (3-fluoro-4-methoxy-benzyl)-amine <BR> <BR> 140 Benzyl- (8-chloro-dibenzofuran-2-yl)-amine<BR> <BR> 141 (9H-Fluoren-2-yl)- (4-methoxy-benzyl)-amine<BR> <BR> 142 (8-Chloro-dibenzofuran-2-yl)-thiazol-2-ylmethyl-amine<BR& gt; <BR> 143 (9H-Fluoren-2-yl)- (3-methoxy-benzyl)-amine 144 (3, 5-Dimethoxy-benzyl)-(9H-fluoren-2-yl)-amine 145 (9H-Fluoren-2-yl)- (3-flUoro-4-methoxy-benzyl)-amine 146 (4-tert-Butyl-benzyl)- (9H-fluoren-2-yl)-amine 147 Benzyl- (9H-fluoren-2-yl)-amine 148 (9H-Fluoren-2-yl)-thiazol-2-ylmethyl-amine 149 (2-Ethoxy-benzyl)- (9H-fluoren2-yl-amine <BR> <BR> 150Dibenzofuran-4-yl- (4-methoxy-benzyl)-amine<BR> <BR> 151 2- [ (8-Chloro-dibenzofuran-2-ylamino)-methyl]-benzonitrile 152 Dibenzofuran-4-yl- (3-methoxy-benzyl)-amine <BR> <BR> 153 Dibenzofaran-4-yl- (3, 5-dimethoxy-benzyl)-amine<BR> <BR> 154 Dibenzofuran-4-yl- (3-fluoro-4-methoxy-benzyl)-amine<BR> <BR> 155 (4-tert-Butyl-benzyl)-dibenzofuran-4-yl-amine 156 Dibenzofuran-4-yl- (2-ethoxy-benzyl)-amine 157 N- (4-Methoxy-benzyl)-N'-methyl-dibenzofuran-2, 8-diamine 158 (8-Chloro-dibenzofuran-2-yl) (4-methoxy-benzyl)-amine 159 (8-Chloro-dibenzofuran-2-yl)- (2-ethoxy-benzyl)-amine 160 Dibenzofuran-4-yl- (2, 4-dimethyl-benzyl)-amine 161 N-Methyl-N'-thiophen-3-ylmethyl-dibenzofuran-2, 8-diamine 162 N-Methyl-N'-pyridin-2-ylmethyl-dibenzofuran-2, 8-diamine 163 (2-Bromo-benzyl)-phenoxathiin-3-yl-amine 164 Phenoxathiin-3-yl-quinolin-4-ylmethyl-amine 165 Phenoxathiin-3-yl-thiophen-3-ylmethyl-amine 166 (3-Methyl-pyridin-2-ylmethyl)-phenoxathiin-3-yl-amine 167 Phenoxathiin-3-yl-pyridin-3-ylmethyl-amine 168 Phenoxathiin-3-yl-pyridin-2-ylmethyl-amine 169 (8-Chloro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine 170 (2-Bromo-benzyl)- (9-ethyl-9H-carbazol-3-yl)-amine 171 (8-Chloro-dibenzofuran-2-yl)- (3-methyl-pyridin-2-ylmethyl)-amine 172 (9-Ethyl-9H-carbazol-3-yl)-thiophen-3-ylmethyl-amine 173 (5-Chloro-thiophen-2-ylmethyl)- (9-ethyl-9H-carbazol-3-yl)-amine 174 (9-Ethyl-9H-carbazol-3-yl)-pyridin-3-ylmethyl-amine 175 (2-Bromo-benzyl)- (9H-fluoren-2-yl)-amine 176 (8-Chloro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine 177 (9H-Fluoren-2-yl)-quinolin-2-ylmethyl-amine 178 (9H-Fluoren-2-yl)-thiophen-3-ylmethyl-amine 179 (9H-Fluoren-2-yl)- (3-methyl-pyridin-2-ylmethyl)-amine 180 (9H-Fluoren-2-yl)-pyridin-4-ylmethyl-amine 181 (9H-Fluoren-2-yl)-pyridin-3-ylmethyl-amine 182 (9H-Fluoren-2-yl)-pyridin-2-ylmethyl-amine 183 (8-Chloro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine 184 Dibenzofaran-4-yl-quinolin-4-ylmethyl-amine <BR> <BR> 185 Dibenzofuran-4-yl-quinolin-2-ylmethyl-amine<BR> <BR> 186 Dibenzofuran-4-yl-thiophen-3-ylmethyl-amine 187 Dibenzofuran-4-yl- (3-methyl-pyridin-2-ylmethyl)-amine 188 Dibenzofuran-4-yl-pyridin-4-ylmethyl-amine 189 Dibenzofuran-4-yl-pyridin-3-ylmethyl-amine<BR> <BR> 190 Dibenzofuran-4-yl-pyridin-2-ylmethyl-amine<BR> <BR> 1 91 (2-Bromo-benzyl)-(8-chloro-dibenzofuran-2-yl)-amine 192 (8-Chloro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine 193 N-Methyl-N'- (2, 3, 6-trifluoro-benzyl)-dibenzofuran-2, 8-diamine 194 N-Methyl-N'- (2, 3, 4-trifluoro-benzyl)-dibenzofuran-2, 8-diamine 195 N- (2, 6-Difluoro-benzyl)-N'-methyl-dibenzofuran-2, 8-diamine 1 96 N-(2, 5-Difluoro-benzyl)-N'-methyl-dibenzofuran-2, 8-diamine 197 N- (2, 4-Difluoro-benzyl)-N-methyl-dibenzofuran-2, 8-diamine 198 N- (2, 3-Difluoro-benzyl)-N'-methyl-dibenzofuran-2, 8-diamine 199 N- (2, 5-Dimethyl-benzyl)-N'-methyl-dibenzofuran-2, 8-diamine 200 N- (2, 4-Dimethyl-benzyl)-N'-methyl-dibenzofuran-2, 8-diamine 201 N-(2, 3-Dihydro-benzo [1, 4] dioxin-6-ylmethyl)-N'-methyl-dibenzofuran-2, 8- diamine 202 (3-Fluoro-2-methyl-benzyl)-phenoxathiin-3-yl-amine 203 (8-Chloro-dibenzofuran-2-yl)- (2, 3, 6-trifluoro-benzyl)-amine 204 Phenoxathiin-3-yl- (2, 3, 6-trifluoro-benzyl)-amine 205 Phenoxathiin-3-yl-(2, 3, 4-trifluoro-benzyl)-amine 206 (2, 6-Difluoro-benzyl)-phenoxathiin-3-yl-amine 207 (2, 5-Difluoro-benzyl)-phenoxathiin-3-yl-amine 208 (2, 4-Difluoro-benzyl)-phenoxathiin-3-yl-amine 209 (2, 3-Difluoro-benzyl)-phenoxathiin-3-yl-amine 210 (2, 4-Dimethyl-benzyl)-phenoxathiin-3-yl-amine 211 (2, 3-Dihydro-benzo [1, 4] dioxin-6-ylmethyl)-phenoxathiin-3-yl-amine 212 Benzo [b] thiophen-5-yl- (3-fluoro-2-methyl-benzyl)-amine 213 (8-Chloro-dibenzofuran-2-yl)- (2, 3, 4-trifluoro-benzyl)-amine 214 (8-Chloro-dibenzofuran-2-yl)- (2, 6-difluoro-benzyl)-amine 215 (8-Chloro-dibenzofuran-2-yl)-(2,5-difluoro-benzyl)-amine 216 (8-Chloro-dibenzofuran-2-yl)- (2, 4-difluoro-benzyl)-amine 217 (9-Ethyl-9H-carbazol-3-yl)- (3-fluoro-2-methyl-benzyl)-amine 218 (8-Chloro-dibenzoRtran-2-yl)- (2, 3-difluoro-benzyl)-amine 219 (9-Ethyl-9H-carbazol-3-yl)-(2, 3, 6-trifluoro-benzyl)-amine 220 (9-Ethyl-9H-carbazol-3-yl)- (2, 3, 4-trifluoro-benzyl)-amine 221 (2, 6-Difluoro-benzyl)- (9-ethyl-9H-carbazol-3-yl)-amine 222 (2, 5-Difluoro-benzyl)- (9-ethyl-9H-carbazol-3-yl)-amine 223 (2, 4-Difluoro-benzyl)- (9-ethyl-9H-carbazol-3-yl)-amine 224 (2, 3-Difluoro-benzyl)- (9-ethyl-9H-carbazol-3-yl)-amine 225 (2, 5-Dimethyl-benzyl)- (9-ethyl-9H-carbazol-3-yl)-amine 226 (2, 4-Dimethyl-benzyl)- (9-ethyl-9H-carbazol-3-yl)-amine 227 (2, 3-Dihydro-benzo [1, 4] dioxin-6-ylmethyl)- (9-ethyl-9H-carbazol-3-yl)-amine 228 (9H-Fluoren-2-yl)- (3-fluoro-2-methyl-benzyl)-amine 229 (8-Chloro-dibenzofuran-2-yl)- (2, 5-dimethyl-benzyl)-amine 230 (9H-Fluoren-2-yl)- (2, 3, 6-trifluoro-benzyl)-amine 231 (9H-Fluoren-2-yl)- (2, 3, 4-trifluoro-benzyl)-amine 232 (2, 5-Difluoro-benzyl)- (9H-fluoren-2-yl)-amine 233 (2, 4-Difluoro-benzyl)- (9H-fluoren-2-yl)-amine 234 (2, 3-Difluoro-benzyl)- (9H-fluoren-2-yl)-amine 235 (2, 5-Dimethyl-benzyl)- (9H-fluoren-2-yl)-amine 236 (2, 4-Dimethyl-benzyl)- (9H-fluoren-2-yl)-amine 237 (2, 3-Dihydro-benzo [1, 4] dioxin-6-ylmethyl)- (9H-fluoren-2-yl)-amine 238 (8-Chloro-dibenzofuran-2-yl)- (2, 4-dimethyl-benzyl)-amine 239 Dibenzofuran-4-yl- (2, 5-dimethyl-benzyl)-amine 240 Dibenzofuran-4-yl- (3-fluoro-2-methyl-benzyl)-amine 241 N- (3-Fluoro-2-methyl-benzyl)-N'-methyl-dibenzofuran-2, 8-diamine 242 (8-Chloro-dibenzofuran-2-yl)- (3-fluoro-2-methyl-benzyl)-amine 243 (8-Chloro-dibenzofaran-2-yl)- (2, 3-dihydro-benzo [1, 4] dioxin-6-ylmethyl)-amine 244 (2, 5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 245 (2, 3-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 246 (2-Chloro-benzyl)-phenoxathiin-3-yl-amine 247 (2-Methoxy-benzyl)-phenoxathiin-3-yl-amine 248 (2-Methyl-benzyl)-phenoxathiin-3-yl-amine <BR> <BR> <BR> <BR> 249 Anthracen-2-yl- (2-chloro-benzyl)-amine<BR> <BR> <BR> <BR> <BR> <BR> <BR> 250 Anthracen-2-yl-(2-fluoro-benzyl)-amine 251 Dibenzo [1, 4] dioxin-2-yl- (2, 3-dimethoxy-benzyl)-amine 252 (2-Chloro-benzyl)-dibenzo [1, 4] dioxin-2-yl-amine 253 2- (Dibenzo [1, 4] dioxin-2-ylaminomethyl)-phenol 254 Dibenzo[1, 4] dioxin-2-yl- (2-methoxy-benzyl)-amine 255 2-[(9-Ethyl-9H-carbazol-3-ylamino)-methyl]-phenol 256 (9-Ethyl-9H-carbazol-3-yl)- (2-fluoro-benzyl)-amine 257 (9-Ethyl-9H-carbazol-3-yl)- (2-methyl-benzyl)-amine 258 (2-Chloro-benzyl)- (9H-fluoren-2-yl)-amine 259 2- [ (9H-Fluoren-2-ylamino)-methyl]-phenol 260 (9H-Fluoren-2-yl)- (2-methoxy-benzyl)-amine 261 (9H-Fluoren-2-yl)- (2-trifluoromethyl-benzyl)-amine 262 (9H-Fluoren-2-yl)- (2-fluoro-benzyl)-amine 263 Dibenzofuran-4-yl- (2, 5-dimethoxy-benzyl)-amine 264 Dibenzofuran-4-yl- (2, 3-dimethoxy-benzyl)-amine 265 2- (Dibenzofuran-4-ylaminomethyl)-phenol 266 Dibenzofuran-4-yl- (2-methoxy-benzyl)-amine 267 (2, 5-Dimethoxy-benzyl)- (3-methoxy-dibenzofuran-2-yl)-amine 268 (2, 3-Dimethoxy-benzyl)- (3-methoxy-dibenzofuran-2-yl)-amine 269 (2-Methoxy-benzyl)-(3-methoxy-dibenzoiran-2-yl)-amine 270 Dibenzofuran-2-yl- (2, 5-dimethoxy-benzyl)-amine 271Dibenzofuran-2-yl- (4-methoxy-benzyl)-amine 272 (2-Bromo-benzyl)-dibenzofuran-2-yl-amine 273 (8-Fluoro-dibenzofuran-2-yl)- (3H-imidazol-4-ylmethyl)-amine 274 2- [ (8-Fluoro-dibenzofuran-2-ylamino)-methyl]-benzonitrile 275 (2-Ethoxy-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 276 (8-Fluoro-dibenzofuran-2-yl)- (4-methylsulfanyl-benzyl)-amine 277 (2-Bromo-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 278 (8-Fluoro-dibenzofuran-2-yl)-quinolin-4-ylmethyl-amine 279 (8-Fluoro-dibenzofuran-2-yl)-quinolin-2-ylmethyl-amine 280 Dibenzoiran-2-yl-naphthalen-l-ylmethyl-amine 281 (8-Fluoro-dibenzofuran-2-yl)-naphthalen-2-ylmethyl-amine 282 (8-Fluoro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine 283Dibenzofurati-2-yl- (2-nitro-benzyl)-amine 284 Dibenzofuran-2-yl- (3H-imidazol-4-ylmethyl)-amine 285 2- (Dibenzofuran-2-ylaminomethyl)-benzonitrile 286 Dibenzofuran-2-yl- (2-ethoxy-benzyl)-amine 287 Dibenzofuran-2-yl- (3-trifluoromethyl-benzyl)-amine 288 (4-tert-Butyl-benzyl)-dibenzofuran-2-yl-amine 289 Dibenzofuran-2-yl- (3-fluoro-benzyl)-amine 290 (2, 5-Dimethoxy-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 291 (2, 3-Dimethoxy-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 292 (4-Benzyloxy-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 293 (3-Benzyloxy-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 294 (4-Chloro-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 295 (3-Chloro-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 296 (2-Chloro-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 297 4- [ (8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol 298 3- [ (8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol 299 Dibenzofuran-2-yl- (2-fluoro-benzyl)-amine 300 (8-Fluoro-dibenzofuran-2-yl)- (4-methoxy-benzyl)-amine 301 (8-Fluoro-dibenzofuran-2-yl)- (3-methoxy-benzyl)-amine 302 (8-Fluoro-dibenzofuran-2-yl)- (2-methoxy-benzyl)-amine 303 (8-Fluoro-dibenzofuran-2-yl)- (4-trifluoromethyl-benzyl)-amine 304 (8-Fluoro-dibenzofuran-2-yl)- (3-trifluoromethyl-benzyl)-amine 305 (4-tert-Butyl-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 306 (4-Fluoro-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 307 (3-Fluoro-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 308 (2-Fluoro-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 309 (8-Fluoro-dibenzofuran-2-yl)- (4-methyl-benzyl)-amine 310 (8-Fluoro-dibenzofuran-2-yl)- (3-methyl-benzyl)-amine 311 Dibenzofuran-2-yl- (2, 6-dimethoxy-benzyl)-amine 312Dibenzofuran-2-yl- (2, 4-'dimethoxy-benzyl)-amine 313 Dibenzofuran-2-yl- (2, 3-dimethoxy-benzyl)-amine 314 (4-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine 315 Dibenzofuran-2-yl- (3-methyl-benzyl)-amine 316 (3-Chloro-benzyl)-dibenzofuran-2-yl-amine 317 3- (Dibenzofuran-2-ylaminomethyl)-phenol 318 (2-Chloro-benzyl)-dibenzofuran-2-yl-amine 319 Dibenzofuran-2-yl- (3-methoxy-benzyl)-amine 320 Dibenzofuran-2-yl- (2-methoxy-benzyl)-amine 321 (9H-Fluoren-2-yl)- (2-methyl-benzyl)-amine 322 Dibenzofuran-4-yl-(2-methyl-benzyl)-amine 323 (8-Chloro-dibenzofuran-2-yl)- (2-methyl-benzyl)-amine 324 (2-Methyl-benzyl)-(lOH-phenothiazin-2-yl)-amine 325 Dibenzo [b, e] [1, 4] dioxin-2-yl- (2-methyl-benzyl)-amine 326 Dibenzofuran-2-yl-(2, 6-difluoro-benzyl)-amine 327 Dibenzofuran-2-yl- (2, 5-difluoro-benzyl)-amine 328 Dibenzofuran-2-yl- (2, 4-difluoro-benzyl)-amine 329 Dibenzofuran-2-yl- (2, 3-difluoro-benzyl)-amine 330 (8-Fluoro-dibenzofuran-2-yl)-thiophen-2-ylmethyl-amine 331 Dibenzofuran-2-yl- (2, 5-dimethyl-benzyl)-amine 332 (8-Fluoro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine 333 (8-Fluoro-dibenzofuran-2-yl)-furan-2-ylmethyl-amine 334 (8-Fluoro-dibenzofuran-2-yl)-furan-3-ylmethyl-amine 335 (8-Fluoro-dibenzofuran-2-yl)- (6-methyl-pyridin-2-ylmethyl)-amine 336 (8-Fluoro-dibenzofuran-2-yl)- (4-methanesulfonyl-benzyl)-amine 337 (8-Fluoro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine 338 (8-Fluoro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine 339 (8-Fluoro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine 340 (8-Fluoro-dibenzofuran-2-yl)- (3-fluoro-4-methoxy-benzyl)-amine 341 Dibenzofuran-2-yl-(2, 4-dimethyl-benzyl)-amine 342 (8-Fluoro-dibenzofuran-2-yl)- (3-fluoro-2-methyl-benzyl)-amine 343 (8-Fluoro-dibenzofuran-2-yl)- (2, 3, 6-trifluoro-benzyl)-amine 344 (8-Fluoro-dibenzofuran-2-yl)- (2, 3, 4-trifluoro-benzyl)-amine 345 (3, 5-Difluoro-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 346 (3, 4-Difluoro-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 347 (3, 5-difluoro-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 348 (2, 6-Difluoro-benzyl (2, 5-Difluoro-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 349 (2, 4-Difluoro-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 350 (2, 3-Difluoro-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 351 (2, 5-Dimethyl-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 352 (2, 4-Dimethyl-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 353 (2, 3-Dihydro-1, 4-benzodioxin-6-ylmethyl)- (8-fluoro-dibenzofuran-2-yl)-amine 354 (3, 5-Dimethoxy-benzyl)- (8-fluoro-dibenzofuran-2-yl)-amine 355 Dibenzofuran-2-yl-furan-2-ylmethyl-amine 356 Dibenzofuran-2-yl-furan-3-ylmethyl-amine <BR> <BR> <BR> <BR> 357 Dibenzofuran-2-yl- (6-methyl-pyridin-2-ylmethyl)-amine<BR> <BR> <BR> <BR> <BR> <BR> 358 Dibenzofuran-2-yl- (4-methanesulfonyl-benzyl)-amine<BR> <BR> <BR> <BR> <BR> 359 Dibenzofuran-2-yl-pyridin-4-ylmethyl-amine 360 Dibenzofuran-2-yl-pyridin-3-ylmethyl-amine 361 Dibenzofuran-2-yl-pyridin-2-ylmethyl-amine 362 Dibenzofuran-2-yl- (3-fluoro-4-methoxy-benzyl)-amine 363 Dibenzofuran-2-yl- (3-fluoro-2-methyl-benzyl)-amine 364 Dibenzofuran-2-yl- (2, 3, 6-trifluoro-benzyl)-amine 365 Dibenzofuran-2-yl- (2, 3, 4-trifluoro-benzyl)-amine 366 Dibenzofuran-2-yl- (3, 5-difluoro-benzyl)-amine 367 Dibenzofuran-2-yl- (3, 4-difluoro-benzyl)-amine 368 Dibenzofuran-2-yl- (3, 4-dimethoxy-benzyl)-amine <BR> <BR> <BR> <BR> 369 Dibenzofilran-2-yl-methyl-(2-methyl-benzyl)-amine<BR> <BR> <BR> <BR> <BR> 370 Dibenzothiohen-2-yl-(2, 4-dimethyl-benzyl)-amine 371 (4-tert-Butyl-benzyl)-dibenzothiohen-2-yl-amine 372 (2-Chloro-benzyl)-dibenzothiohen-2-yl-amine 373 Dibenzothiohen-2-yl- (2, 6-difluoro-benzyl)-amine 374 Dibenzothiohen-2-yl- (2, 3, 6-trifluoro-benzyl)-amine 375 Dibenzothiohen-2-yl-(2-fluoro-benzyl)-amine 376 Benzyl-dibenzothiohen-2-yl-amine 377 Dibenzothiohen-2-yl- (4-methoxy-benzyl)-amine 378 Dibenzothiohen-2-yl-(2, 3-dimethoxy-benzyl)-amine 379 Dibenzothiohen-2-yl- (2, 5-difluoro-benzyl)-amine 380 Dibenzothiohen-2-yl- (3-methoxy-benzyl)-amine 381 Dibenzothiohen-2-yl- (2, 3, 4-trifluoro-benzyl)-amine 382 (-2-Bromo-benzyl)-dibenzothiohen-2-yl-amine 383 Dibenzothiohen-2-yl- (2, 3-dihydro-1, 4-benzodioxin-6-ylmethyl)-amine 384 Dibenzothiohen-2-yl- (3-fluoro-4-methoxy-benzyl)-amine 385 Dibenzothiohen-2-yl- (2, 5-dimethyl-benzyl)-amine 386 Dibenzothiohen-2-yl-thiophen-3-ylmethyl-amine <BR> <BR> <BR> <BR> 387 Dibenzothiohen-2-yl-naphthalene-1-ylmethyl-amine<BR> <BR> <BR> <BR> <BR> <BR> 388 Dibenzothiohen-2-yl- (2-trifluoromethyl-benzyl)-amine 389 Dibenzothiohen-2-yl-naphthalen-2-ylmethyl-amine 390 Dibenzothiohen-2-yl- (2-ethoxy-benzyl)-amine 391 (10, 11-Dihydro-5H-dibenz [b, f] azepin-2-yl)- (3-fluoro-2-methyl-benzyl)-amine 392 (10, 11-Dihydro-5H-dibenz [b, fazepin-2-yl)-(2-methyl-benzyl)-amine 393 (10, 11-Dihydro-5H-dibenz [b, fRazepin-2-yl)-(2, 4-dimethyl-benzyl)-amine 394 (4-tert-Butyl-benzyl)- (10, 11-dihydro-5H-dibenz [b, q azep in-2-yl)-amine 395 (2-Chloro-benzyl)- (10, 1 l-dihydro-5H-dibenz [b, fJazepin-2-yl)-amine 396 (2, 6-Difluoro-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl) -amine 397 (10, 11-Dihydro-5H-dibenz [bvinazepin-2-yl)-(2, 3, 6-trifluoro-benzyl)-amine 398 (10, 1 1-Dihydro-5H-dibenz [b, fzazepin-2-yl)-(2-fluoro-benzyl)-amine 399 (10, 1 1-Dihydro-5H-dibenz [b, f]azepin-2-yl)-(3, 5-dimethoxy-benzyl)-amine 400 B enzyl-(10, 11-dihydro-5H-dibenz [b, f] azepin-2-yl)-amine 401 (10, 1 1-Dihydro-5H-dibenz [b, f]azepin-2-yl)-(4-methoxy-benzyl)-amine 402 (10, 1 1-Dihydro-5H-dibenz [b, flazepin-2-yl)-(2, 3-dimethoxy-benzyl)-amine 403 (2, 5-difluoro-benzyl)-(10,11-dihydro-5H-dibenz [b, f]azepin-2-yl)-amine 404 (10, 11-Dihydro-5H-dibenz [b, f]azepin-2-yl)-(3-methoxy-benzyl)-amine 405 (10, 11-Dihydro-5H-dibenzrb, Qazepin-2-yl)-(2, 3, 4-trifluoro-benzyl)-amine 406 (2-Bromo-benzyl)-(10, 11-dihydro-5H-dibenz [b, f]azepin-2-yl)-amine 407 (2, 3-Dihydro-1, 4-benzodioxin-6-ylmethyl)- (10, 11-dihydro-5H- dibenz [b, fgazepin-2-yl)-amine 408 (10, 11-Dihydro-5H-dibenz [b, rnazepin-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine 409 (10, 11-Dihydro-5H-dibenz [b, f]azepin-2-yl)-(2, 5-dimethyl-benzyl)-amine 410 (10, 1 l-Dihydro-5H-dibenz [b, Qazepin-2-yl)-thiophen-3-ylmethyl-amine 411 (10, 11-Dihydro-5H-dibenz [b, f] azepin-2-yl)-naphthalen-1-ylmethyl-amine 412 (10, 11-Dihydro-5H-dibenz [b, luazepin-2-yl)-(2-trifluoromethyl-benzyl)-amine 413 (10, 1 l-Dihydro-5H-dibenz [b, fJazepin-2-yl)-naphthalen-2-ylmethyl-amine 414 (10, 11-Dihydro-5H-dibenz [b, f]azepin-2-yl)-(2-ethoxy-benzyl)-amine 415 (3-Fluoro-2-methyl-benzyl)-(10H-phenothiazin-2-yl)-amine 416 (2, 4-Dimethyl-benzyl)- (10H-phenothiazin-2-yl)-amine 417 (4-tert-Butyl-benzyl)- (10H-phenothiazin-2-yl)-amine 418 (2-Chloro-benzyl)-(lOH-phenothiazin-2-yl)-amine 419 (2, 6-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine 420 (lOH-Phenothiazin-2-yl)-(2, 3, 6-trifluorobenzyl)-amine 421 (2-Fluoro-benzyl)- OH-phenothiazin-2-yl)-amine 422 (3, 5-Dimethoxy-benzyl)-(lOH-phenothiazin-2-yl)-amine 423 Benzyl-(10H-phenothiazin-2-yl)-amine 424 (4-Methoxy-benzyl)-(10H-phenothiazin-2-yl)-amine 425 (2, 5-Difluoro-benzyl)-(lOH-phenothiazin-2-yl)-amine 426 (10H-Phenothiazin-2-yl)- (2, 3, 4-trifluoro-benzyl)-amine 427 (2, 3-Dihydro-1, 4-benzodioxin-6-ylmethyl)- OH-phenothiazin-2-yl)-amine 428 (3-Fluoro-4-methoxy-benzyl)-(lOlI-phenothiazin-2-yl)-amine 429 (2, 5-Dimethyl-benzyl)-(lOlH-phenothiazin-2-yl)-amine 430 (lOH-Phenothiazin-2-yl)-thiophen-3-ylmethyl-amine 431 (10H-Phenothiazin-2-yl)- (2-trifluoromethyl-benzyl)-amine 432 (9H-Carbazol-3-yl)- (3-fluoro-2-methyl-benzyl)-amine 433 (9H-Carbazol-3-yl)- (2-methyl-benzyl)-amine 434 (9H-Carbazol-3-yl)-(2, 4-dimethyl-benzyl)-amine 435 (4-tert-Butyl-benzyl)- (9H-carbazol-3-yl)-amine 436 (9H-Carbazol-3-yl)- (2-chloro-benzyl)-amine 437 (9H-Carbazol-3-yl)-(2, 6-difluoro-benzyl)-amine 438 (9H-Carbazol-3-yl)- (2, 3, 6-trifluoro-benzyl)-amine 439 (9H-Carbazol-3-yl)- (3, 5-dimethoxy-benzyl)-amine 440 (9H-Carbazol-3-yl)-(2, 3-dimethoxy-benzyl)-amine 441 (9H-Carbazol-3-yl)- (2, 5-difluoro-benzyl)-amine 442 (9H-Carbazol-3-yl)- (2, 3, 4-trifluoro-benzyl)-amine 443 (9H-Carbazol-3-yl)- (2, 3-dihydro-1, 4-benzodioxin-6-ylmethyl)-amine 444 (9H-Carbazol-3-yl)- (2, 5-dimethyl-benzyl)-amine 445 (9H-Carbazol-3-yl)-naphthalen-1-ylmethyl-amine 446 (9H-Carbazol-3-yl)-naphthalen-2-ylmethyl-amine 447 Dibenzofuran-2-yl-bis- (2, 3-dihydro-benzo [1, 4] dioxin-6-ylmethyl)-amine 448 Dibenzofuran-2-yl-bis-thiophen-3-ylmethyl-amine 449 Dibenzofuran-2-yl- (4-phenoxy-benzyl)-amine 450 2-Dibenzofuran-2-yl-2, 3-dihydro-lH-isoindole 451 2-Dibenzofuran-2-yl--lH-isoindole-1, 3-dione<BR> <BR> <BR> 452 Dibenzofuran-2-yl- (4-trifluoromethoxy-benzyl)-amine<BR> <BR> <BR> 453 Dibenzofuran-2-yl- (2-methoxy-benzyl)-amine<BR> <BR> <BR> 454 Dibenzofuran-2-yl- (3-phenoxy-benzyl)-amine<BR> <BR> <BR> 455 Dibenzofuran-2-yl-methyl (2-methyl-benzyl)-amine 456 Dibenzofuran-2-yl- (l-phenyl-butyl)-amine 457 Dibenzofuran-2-yl-phenethyl-amine 458 Dibenzofuran-2-yl-(1-phenyl-ethyl)-amine EXAMPLES Example MOLSTRUCTURE General M+H MOLECULAR proce- (APCI) * FORMULA dure 1 H, c 7 282 C18H19N 02 H CH3 o, 0 2 7 250 C18 H19 N W f H H 3 7 250 C18 H19 N CH3 4 H, c c 7 293 C20H24N2 H /N\ ^ A CH, 256 C16 H17 N 02 NOCH3 /NOCH3 0 OUZO O (3) 5. 314C18H19N 02 S w its ouzo o 5 310 C20 H23 IV H23 LINO /nez 0 8 5 284 C18 H21 N 02 0 , CH3 Zu H3c, 0 i HaC 9 270 C 17 H 19 N 02 H CL3 \ I CH3 OUZO O 10 H 7'5 308 C20 H25 N3 N"*'ON H rr nu 11 sN 5 371 C26 H30 N2 NNo cl3 CH3 12 5, 7 265 C18 H20 N2 roh N H 13 5 328 C24 H25 N cl 3 H 14 7238C17H19N CH H H 15''5346C18H19N04 o S 0 s N je NIT H3c'0H 16 H3C CH3 6 322 C22 H27 N O o i'v\ CH3 c3 17 6 320 C22 H25 H25 N O o zon H 18 0 H H 6 318 C22 H23 N O IN I [JH H 19 H 6 348 C24 H29 N O o 20 0 6 278 C19 H19 N 0 \/'N H 21 6 322 C22 H27 N 0 \/ p HaC CH3 H H H 22 6 292 C20 H21 N 0 N I H 23 eN 6 252 C17 H17 N O ooh o 6, 5 296 C19 H21 N 02 erz H3C-O H<O 25 6, 5 264 C19 H21 N Neo 26 0 4 360 C20 H25 N 0 N"'S'CH 3 S2 vs CH3 27 o I w cH3 4 324 C22 H29 N 0 -N'-'CH3 HOCH HCCH, 28 4 268 C18 H21 N 0 CH3 29 4 5 357 C20 H24 N2 02 H ru'tu w o s /\ 30 c cH, 5, 7267C18H22N2 H NOCH3 / CH, 31 H3c, N'CH3 5, 7 325 C20 H24 N2 S H tS S 32 c en, 5, 7 307 C21 H26 N2 H neo \ U 33 c en, 5, 7 321 C22 H28 N2 H neo \ 34 n, c en, 5 295 C20H26N2 H Nr CH3 CH3 35 HscN-cH3 5 293 C20 H24 N2 N , N CH3 36 5, 7 281 C19 H24 N2 H N--CH3 CH3 37 5, 7 224 C16 H17 N 1 \ HJCH3 5 282 G 18 Fi 19 N S i a , s N-v H 39 H 5, 7 278 C20 H23 N nez H H 40 5 316 C17H17iV03 s o \ _ o zizi H 9 SGNH 5, 6 267 C N H 42 wH CH3 5, 6 226 C15 H15 N 0 noch3 43 5, 6 266 C18 H19 N 0 N'O H 5 252 C17H17N0 NEZ H 45. H 5 316 C17 H17 N 03 0 S So zozo 5 267 C17 H18 N2 0 H ZON H H H 47 5 226 C15 H15 N 0 cl I CfH3 ii r' \=tH CH3 5 24 C17H17iVOS 0 \t N ruz N 495266C18H19NO % N I H H 50 NO % N'O w H 51 5 308, 310 C19Hl4CINO o H 52 ci CI 2 353. 355 C19 H13 CIN2 Ji 03 g zozo 01- 53 2 358 C20 H14 F3 N L 02 O W I F l'F C) F 54 eNX 2 318 C20 H15 N 03 zozo o 55o2332C21H17N03 zozo 0' o 56 H3C>o 334 C21 H19 N 03 I gNto Neo W I CH3 O 57 F F 2 342 C20 H14F3N 0 H F of 58 e2> 1, 2, 3 288 C20 H17 N 0 / H ! ! ! oJ 59 280 G17H13NOS N 60 NO+ 2 319 C19 H14 N2 03 H N"'0 b 0 j' t 61 2 320 C20 H17 N 0 S N 62 X< 2 288 C20 H17 N 0 /\ w c" N_ 63 2 274 C19 H15 N 0 H j 1 0 O's 64 2 380 C26 H21 N 02 Ç eux 0 65 5 330 C23 H23 N 0 xi CH3 66oen, 5332C22 H21 N 02 3 H , 'CH3 67 o I w cH 5 270 270 C17 H19 N 02 H OH C H3 5 268 C18 H21 N O \ CHa CL3 CH, 69 CH3 5 254 C17 H19 N 0 '/NCH3 li 70 wHCCH3 5 268 C18 H21 N O /CHs 71 5 294 C20 H23 N O NEO CHUS 72 H23 N 0 in o 73 0 N'O 5, 6 280 C19 H21 NO H H 74 SNX 5, 6 284 C17 H17 N O S N'O XI H 75o-'5270C16H15NOS Nits H 76 CH3 5 254 C17 H19 N O N H "CL, 77/H5254C17H19NO 0-cr CH3 0' 3 78 ci3 5, 6 240 C16 H17 N O N H dan 79 N 3 293 C18 H13 F N2 0 zizi N H I/ 80-N 3 276 C17 H13 N3 0 0 o wu N w H N L TN 3 269 C19 H16 N2 0 H N 'N H I/ X 3 321 C20 H17 F N2 0 \/ F 83 H H 3 354 C23 H19 N3 O N/ 'LN XI H I N 84 3 353 C24 H20 N2 0 O HN /H I HN CH3 X M"3 381 C21 H20 N2 03 s 0 6 s"0 H3 o H3C 86 304 C19 H17 N3 O 0 N H 87 N-CH3 3 317 C21 H20N2 O 0 cl3 N H H I/ 88 NH 3, 2 355 C23 H18 N2S NH S wl li 89 w+vSs 3 383 C20 H18N2 02 I S2 H I/O H Is" H3C0 H, C"0 90 N SS CH3 3 339 C19 H15F N2 O S HO 91 3 325 C18 H13 F N2 os Nez N H FI F 92 N S 3 358 C21 H15 N3 0 jazz ". H N H 93 3 357 C22 H16 N2 0 SA (q s H H I w 3 385 C 19 H 16 N2 03 C- (S2 0 N H3C 95 3 308 C17 H13 N3 0 S+ N XN XI H N 96 3 321 C19 H16 N2 0 s Xi H LU H >3 97 3335C24H18N2 to 9 H XjN N 98 3 362 C22 H19 N 02 s N XI I . o H CSO 3 99 3 285 C20 H16 N2 N Zizi H 100 3 298 C22 H19 N CL3 N H 101 C20H16FN H 102 1 3 308 C19 H14 F N 0 02 F H 103o"3341C22H16N202 cy N 104 1 3 340 C23 H17 N 02 P-0 o lui H I 105 03368C20H17N04 I i o I i N Iw o S H, HO 3 106 3 291 C18 H14 N2 02 Po o H N H I N U7"ow3322C20H16FN 02 THX 0 cl 108 OH 3 308 C19 H14 F N \/) 02 0 F N H I/ 109 on 3 368 C20 H17 N 04 zu 0 H ."s"0 HIC 3 110 oH 3 291 C 18 H 14 N2 02 han o H H I 111 oH 3 304 C20 H17 N 02 cl3 0 N N H I/ 12"ci3326, 328 C19H13C ! FN 0 ru ! 1 N H I 113 3 359 C23 H16 Cl N 0 Ci ci l X H3C 03 S 03S o 1 N^ H. /O H CSO 3 115 5H'335502022 N2 02 XH CS O S H"0 HIC 124 F 2 292 C19H14FNO óA N H H I/ 125 Q-CH3 2 333 C21H20N202 zip N ! H H3c, 0 126 os 2 363 C22H22N203 HN 0 CH3 H3Co HN 127 0 2 359 C24H26N201 , C H 3 HN H3C CH3 CH3 128 N-CH3 2 303 C20H18N201 A N N I H 129H2328C21H17N301 X1 N H Nazi N N N 130. s2336C20H17N102 S1 W° H% loowCH3 116 3 278 C18 H19 N3 I H I ZON 117 3 307 C19 H15 F N2 O 0 cl3 F H I 118 . 2, 3325C22H16N20 N ici _ I N 119 o t 2 325 C22 H16 N2 0 0 N wl I 120 F 2 335 C21 H19 F N2 O o N H cl3 C H3 121 2 317 C21 H20 N2 0 0 o CL3 C s 0 - If 0 O S \ H \Lj/0 v/ H 1/o_ 123 2 281 C16 H12 N2 0 s o Non SU 131 ci 2 338, 340 C20H16N102 Cil 0 CH3 N'--au H I 132 2 336 C20Hl7O2SI 0 Nl s I I H3C 133 ° H X 2 366 C21H1903N1 I S1 . 0 134 s 2 354 C20H1602N1 I S1 F1 ho CH3 135. s2362C23H2301N1 w S1 H i'/ s 3 136 s 2 306 C19H15N101 SI "*fizz H 137cH, 2350C21H19N102 r oJ S1 N w a Fi 138 ci 2 368, 370 C21 H1 8N103 Cil 0 CH 3 O H I H, C H 139 2 356, 358 C20H15N102 Cil Fl 0 F CHEZ H CH3 140 ci 2 308, 310 C1 9H1 4NOCI \/ N I w H I/ 141 2 302 C2lHl9NO Cl 3 , cH3 142 ci 2 315, 317 C15H11N20CI zu 0 s 143 . 2302C21H19NO ? H, I 144 H 2 332 C22H21 N02 cl, H I N3C. 0 145 2 320 C21 H18NOF I N H I/ CL3 CH3 146 2 328 C24H25N zizi H CH3 H3C CH3 147 2 272 C20Hl7Nl - i N H I/ 148 2 279 C16Hl4N2S -ITS 149 CH3 2 316 C22H21NO 0 N H I/ 150 2 304 C20Hl7NO2 w 0 H /o, CH3 151'a2334C20H13N20d \/ o 11 H H I/ 152 a H3 2 304 C20H17N02 zizi o H I \/ 153 H3 2 334 C21 H19N03 Hic'° w w o H I H3C. 0 154 a 2 322 C20H16NF02 N cl 155 2 330 C23H23NO N -H /CH3 \ 156 CH3 2 318 C2lHl9NO2 o N H / 157 MH CH3 2 333 C21H20N202 N-CH3 \ H O CH3 158"a2338, 340 C20H16N02C ! 0 o H CH3 H /O, CH3 159 ß J 2 352, 354 C21 H1 8N02CI v i J H3 o I H H I/ 160 2 : 302C21 H19NO N I CH3 161 N-CH3 2 309 C18 H16 N2 0 s \ N H 162 r f Hr 304 C19 H17 N3 0 "nu \ H 163 s Br 2 383, 385 C19H14BrN Ors 1642357C22H16N20 i o S S I N i H I 165 2 312 C17 H13 N 0 19, o S2 zozo I 1662321C19H16N20 i o S S I w CH3 "nu H Nw 167s2307C18H14N20 IN S . ho 168s2307C18H14N20 S o 169 ci 2 314, 316 C17Hl2CINO S o H S 170 2 379, 381 C21 H 19 Br N2 /'-N Br Bu HIC H I 171 2 323, 325 C19 H15 CI N2 zu 0 N N H I/ HS 172 2 307 C19 H18 N2 S Y N S H ; C 173 2 341, S -N N li Ci 174 2 3b2 C20 H19 N3 f-N H3C N HaC w N N H I/ 175 ber 2 350, 352 C20 H16 Br N - H I/ 176 3 309, 311 C18 H13 Cl N2 \/ H XN xi H 1 177 2 323 C23 H18 N2 - i i 1 I 178 2 278 C18 H15 N S zon s 179 2 287 C20 H18 N2 - Hic Hic 180 2 273 C19 H16 N2 ) zon H 181 2 273 C19 H16 N2 -I/N N H I/ 182T2273C19H16N2 N N 183 311 C18H13C) N2 \/ o w N , N H 184 325 C22 H16 N2 0 zu H N 185 2 325 C22 H16 N2 0 c, N w 186 2 2. 80 C17Hl3NOS ors \/ 187 2 289 C19 H16 N2 0 o /hic 188 2 275 C18 H14 N2 0 N I N O 189 2 275 C18 H14 N2 0 H I/ zozo 1902275C18H14N20 N \/° 191 389 C19 H13BrC ! NO I N H I/ 192 ci 2 309, 311 C18 H13 Cl N2 0 0 N H I 193 F 2 357 C20 H15 F3 N2 F 0 F N CH, RUZ F^s 194 F 2 357 C20 H15F3 N2 F, F N i of N-CH3 195 HN 2 339 C20 H16 F2 N2 H °\J F N CH3 196 F 2 339 C20 H16 F2 N2 N \ F O 0 HN _CH, 197 F F 2 339 C20 H16 F2 N2 O If 0 l N-cH3 198 339 C20 H 16 F2 N2 F 0 I If NH H-CFi3 199 H 2 331 C22 H22 N2 0 Cri 'U N-CH3 H 200 HA3 CH3 2 331 C22 H22 N2 0 If 0 N-CH3 N-CH3 201 2 361 C22 H20 N2 03 o N / O N-CH3 202 2 338 C20 H16F N O S zozo cl 203 F 2 363 C19 H11 CIF3 NO ci C ! CI 204 F 2 360 C19 H12 F3 N //N I/F O S S F 205 F 2 360 C19 H12 F3 N ORS H I s I . 0 Ub kAsJ' 206 : 342C19H13F2N ORS F S 207 F 2 342 C19 H13 F2 N os p os I s I 208 NB 2 342 C19 H13F2 N ors I s s 209 2 342 C19 H13 F2 N OS -a N"' (F 210 HC CH3 2 334 C21 H19 N O S H IN su o 211 0 2 364 G21 H 17 N 03 o S I sr zozo 212F2272C16H14FNS H3C/ w w RIZ s 213 OF3 NH + N O cl O CI 214 2 345 C19H120F2 Nô F a CL 215 F 2 345 C19 H12 CI F2 Nô Nazi zu 0 /\ ce 216 2 345 C19 H12 CIF2 In O N N 0 F CRI 217 HX 2 333 C22 H21 F N2 F \ I CH3 N 218 2 345 C19 H12 CIF2 X N 0 cl'' Cl 219 g 2 355 C21 H17F3 N2 F H \ I F H3C F 220 H A 2 355 C21 H17F3N2 F HIC H3 L N 221 F 2 337 C21 H18F2 N2 RIZ H, C N \ I F 222 F 2 337 C21 H18 F2 N2 ZON H C N 3\-N F N 223 2 337 C21 H18 F2 N2 N i H \ I F N mos 2242337C21H18F2N2 F H, C N4 F \ I F 0 225 CH 2 329 C23 H24 N2 RIZ H N 1-4 W I CH3 0 226 2329C23 H24 N2 N I H3 .. _N CH3 N 227 2 359 C23 H22 N2 02 H I ° zon N 228 2 304 C21 H18 F N F " (F 229 337 C21 H18 CI fV O H JEU Cl 230 F 2 326 C20 H14 F3 N F IF 231 2 326 C20 H14 F3 N F N4F 232 F 2 308 C20 H15 F2 N I F 233 2 308 C20 H15 F2 N H F 234 I 2 308 C20 H 15 F2 N F F X X XCH 2 300 C2 m cl3 I i CH3 236 I cH3 2 300 C22 H21 N w \/I/CH3 237 0 2 330 C22 H19 N 02 xi . N 238 H 2 336, 338 C21 H18 Cl N If CH3 ci CI 239 2 302 C21 H19 NO cl3 i CH3 240 2 306 C20 H16 F N 0 /\ o /NIF . CH3 241 F 2, 3 335 C21 H19 F N2 ho \ \ C) H-CH3 242 2, 3 341 C20 H15 Cl F N 1 0 Cl3 Ci 243 o) 2 367 C21 H16 CIN ci 0 03 i /\ wI N wl o-J 244 s 2 366 C21 H19 N 03 C3 ho i CH3 CH, 245 H19N03 s s H N \O 0 246 H X ? 2 340, 342 C19 H14 CIN O S jazz ci 247 : 336C20H17N02 riz xi CH. 0""JI 248 S 2 320 C20 H17 N 0 S Cl "I H, CH2 249 WHd 2 318, 320 C21 H16 Cl N cri XI ci lu F "'S"6 250 2 302 C21 H 16 F N H I F N H 25102350C21 H19N04 0 H tjj HX CH H CH3 252 2 324, 326 C19Hl4CIN 02 ou 0 N 253 2 306 C19 H15 N 03 ho ou N HA 2542320C20H17N03 0 ou N H 255 2 317 C21 H20 N2 O ru HN OU I \ 256 2 319 C21 H1 F N2 ho .-N c rj) p \ nez 257 2 315 C22 H22 N2 ru H- N "6 H 258 ho 2 306, 308 C20 H18 CIN ci NEZ I \ 259 . 2288C20H17NO ou H i 260 H19NO % N O-CH l H i 261 '2 : 340C21H16F3N p F i N H i 262 2 290 C20 H16 F N % N F I i 263 , cH, 2 334 C21 H19 N 03 v o o H, cl 264 H19N03 1 u-° H CH3 265 2 290 C19 H15 N 02 Oh N 266 cH, 2304C20H17N02 N-16 ° s 267 2 364 C22 H21 N 04 H C Tich3 N \ N' H3C'o H3C. 0 268 2 364 C22 H21 N 04 0 H3c. 0 HC'LJ' H30H 3 . O H oCH3 H3C 269 2 334 C21 H19 N 03 vs oh 0'CH3 N H3CIO H3C. 0 , 270 Eco 2 334 C21 H19 N 03 W, v du cl O \ I 'CH 3 271 HND CH3 2 304 C20 H17 N 02 /N i C) 272 353 C19H14BrN N 0 Ber 0 273 N 2 282 C16 H12 F N3 H CL N F H 274 2317C20H13FN2 O H zon F 275 2 336 C21 H18 F N N,, P 02 C) 0) CH3 F 276 s2338C20H16FNO S H 3 s F 277 HN 4 2 369, 371 C19H13BrF N H Au ber OU F 278 N 2 343 C22 H15 F N2 \ I I O o i 279 2343C22H15FN2 H Xi 0 N F 280 e HN 4 2, 3 324 C23 H17 N O H o i 281 HN X 2 342 C23 H16F N O RIZ N 0 F F 282 F 2 342 C23 H16 F N 0 0 N I 283 2 319 C19 H14 N2 03 N I cy / 2 264 C16 H13 N3 O nu \. H 2852299C20H14N20 I N NU /\ 286 H19N02 H N 0 287 2 342 C20 H14 F3 N F \ I F O X 3 2 330 C23 H23 N O H \. CHs C) O 289 292 C19 H14 F N O H N F 290 H3CsO 2 352 C21 H18F N 03 N 0 F 291 2 352 C21 H18 F N , N I/o. CH3 3 N 0 CH3 F 292 2 398 C26 H20 F N 02 H 0 N XI F F 293 Ns, 2 398 C26 H 20 F N H) !) qu N 02 F F 294 ci cl 2 326, 328 C19Hl3CIFN I O F C) F 295 2 326, 328 C19 H13 Cl F N F ci 0 F 296 2 326, 328 C19 H13 Cl F N I O Cri cri o F 297 OH 2 308 C19 H14 F N 02 I C) /\ F 2, 3 308 C19 H14 F N H Oh ou F F 299 2 292 C19Hl4FNO I OU F 300 HX CH3 2 322 C20 H16F N N 02 0 F F 301 : 322C20 H16 FN H 02 0 C) CH3 F F 302 2322C20 H16 FN H L cn. F F 303 F F 2 360 C20 H13F4N H F 0 C) F 0 F 304 2 360 C20 H13F4 N O F F F C) F 305 N@3 2 348 C23 H22 F N O H W CHs , NAZI C) 0 F 306 F 2 310 C19 H13 F2 N H 0 XI F F 307 2 310 C19 H13 F2 N H ! ! n N F \ O F 308 3310C19H13F2N H 0 F O F F 309 nua 2 306 C20 H16 F N O , N I/ . O F 310 2 306 C20 H16 F N 0 c H3 0 311 HNX 2 334 C21 H19 N 03 o If C) 0, CH3 0 312 2 334 C21 Hl 9 N 03 I 0 CH, 3 313 H19N03 H N4"C'3 314 2 380 C26 H21 N 02 rY° o N I 0 0 315 2 288 C20H17 N0 N N CH3 C) 316 2 308, 310 C19 H14 CIN O N ci 0 / J, H Ja < I OUR \ O Ns9 2 308, 310 C19 H14 CIN O /N \ I CI ci 319 2304C20H17 N02 zozo N 0 CL3 320 2304C20H17 N02 H N dozy 321 2 286 C21 H19 N H N CH3 i 322 2 288 C20 H17 N O NH CH3 w % 323 323 R 2, 3 323 C20 H16 CIN O ci NH 0 O 324 2 319 C20 H18 N2 S H N-/CH, H N s 325 N9CH 2, 3 304 C20 H17 N 02 Hop N-/CHg 0 326 2 310 C19 H13 F2 N H N 0 F 327 F 2 310 C19 H13 F2 N w p I H F 328 2 310 C19 H13 F2 N H , qF N 0 F 329'. 2 : 310C19H13F2N H ! i ! n /N. I/F . 2 3in ZU 330 H s 2 298 G17H12FN0 N, S 0 F 331cHg2302C21 H19NO N RIZ N zu 332 H s 2 298 C17 H12 F N 0 N s XI F 333 H °) i 2 282 C17 H12 F N orN99/02 0 F F 334 nos 2 282 C17 H12FN 02 0 F F 335 2 307 C19 H15 F N2 H 0 C) 3 F 336 °\ o 2 370 C20 H16 F N 03 S N 0 F F 337 2, 3 293 C18 H13 F N2 N I p XI 0 F F 338 2 293 C18 H13 F N2 i N I N O 0 ZUR F 339 2 293 C18 H13 F N2 H IN O N N °\-J 340, CH3 2 340 C20 H15F2 N 02 F N F C) F 341 3 2 302 C21 H19 NO N I gNW CL3 342 2, 3 324 C20 H15 F2 N H N F 0 0 CH3 F F X » 2 346 C19 H11 F4N H ! j ! n N 0 F F 344 SF 2 346 C19 Hll F4 N H 0 N F F 0 F 345 F 2 328 C19 H12 F3 N 0 i N I F O o7N F F F 346 : 328C19H12F3N H 0 F F 0 347 F 2 328 C19 H12 F3 N H F F 0 348 F 2 328 C19 H12 F3 N 0 I BY F F 349 NX 2 328 C19 H12F3 N H", qu \ I F F 0 350 2328C19H12F3N H N 0 \ I F F F 351 9 2 320 C21 H18 F NO I \ I CH3 CL3 F 352 2320C21 H18FNO I N CL3 F 353 N 2 350 C21 H16F N 0 03 RIZ 0 F F F 354 H3Cso 2 352 03 03 zozo H F cl3 F 355 NX 2 264 C17 H13 N 02 r N./ O sL NX 2 264 C17 H13 N 02 N 0 357 2 289 C19 H16 N2 0 H) ! i b 0/ O 358 0. 0 2, 3 352 C20 H17 N 03 sus H CH, N 0 359 2, 3 275 C18 H14 N2 0 N I XI 0 360 2 275 C18 H14 N2 0 N N b 361 2 275 C18 H14 N2 0 N N b oy 362 C, H3 2 322 C20 H16F N 02 ob. N F C) 363 Ns9s 2, 3 306 C20 H16 F N O F N 0 CH3 364 2 328 C19 H12 F3 N H 0 NF F C) 365 : 328C19H12F3N N F F 0 F \ I F 0/ 366 F 2 310 C19H13F2N 0 /N. I/F C) 367F2310C19H13F2N H ft (n N F 0 /\ 368cw, 2334C21 H19N03 o I o N 0 CL3 369 304 C20H17NS cl3 N I N H I/ 370-2 318 C21 H 19NS CH3 N H I ""CH, 371 2 346 C23H23NS s SU H CH3 N H /CH3 H3C CH3 372 2 323, 325 C19H 14CINS ci cl I N H 373 2 326 C19Hl3F2NS s I F "H'Y) F F 374 2 344 C19Hl2F3NS S s F if H I H_ 375 2 308 C19Hl4FNS s F qN I N H I/ 376-2 290 C19H15NS \/ "' H I/ 377 2 320 C20H I 7NOS \/ s I N H /o, CH3 378-2 350 C21 H 19 N 02S \/ g H3C. 0 H J O. CH3 379 2 326 C19H13F2NS F sq N w H I/ F 360 HX 2 320 C20H 1 7NOS s CH3 /cl3 zozo H / 381 2 344 C19Hl2F3NS s F S F N l H I/ F 382 2 369 C19Hl4BrNS s ber Ber H H I/ 383 2 348 C21 H 17N025 s I N wl N w H I/ o1) J 384 2 338 C20H 16FNOS \/ N H Cl O CH3 385 2 318 C21 H I 9NS \/ S N H I/ 3 386 ti HX 2 296 C17H13NS2 N s 1 s 387 < 2 340 C23H17NS _ i /H I -2 358 C20H 14F3NS I,, F S/I F F,,,, s F F 1 ts 2 340 C23H17NS \/ s I H I I 390/=\ 2 334 C2im9NOS v i j H, s 0) H I/ 9 HXl 2 333 C22H21 FN2 N N HUI HIC H 392 2 315 C22H22N2 I HIC N HIC 393 2 329 C23H24N2 ZULU H3C CH3 CH3 394 357 C25H28N2 N 1, CH H3C CH3 395 2 334, 336 C21 H 19CIN2 "jazz N I N H CRI 396 2 337 C2lHl8F2N2 N F H--I N /\ 2 355 C21 H 17F3N2 "FRY N H F H I 398 2 319 C21 H I 9FN2 N N FUZZ cH3 2 361 C23H24N202 N 0 H 11 H3C, 0 400 | 2 301 C21 H20N2 N N I N H 401 0 CH,, 2 331 C22H22N20 I o, CHg 402 O CH 2 361 C23H24N202 N/ N HsKG. O w OC3 403 337 C21 H 1 8F2N2 N-1- F F 404 cH, 2 331 C22H22N20 I o N H I/ 405 2 355 C21 H1 7F3N2 F H I/ H 406 S HS 2 380 C21 H 1 9BrN2 N H Bu 407 N 2 359 C23H22N202 Holz H I 01.,) ZU 408 N 2 349 C22H21FN20 I F H H I/ O i CH3 74SX cH, 2 329 C23H24N2 Cl3 CHs 4102307C19H18N2S Herz H H \=/ 411 2 351 C25H22N2 N N H I 412 N \ F F F 2 369 C22H19F3N2 _' i N w H I/ 413y2351C25H22N2 N N Zu 414 CH3 2 345 C23H24N20 N v N oJ N" H I/ 415p2337C20H17FN2S NH Sk CH, F 416 2 333 C21 H20N25 NH Sk CH, "L-CH, CH3 417 2 361 C23H24N2S NU S 6-N W w H I/CH3 H3C CH3 4-18 2 2 338, 340 C19H15CIN2S ""NH CI H-b H I 4192341C19H14F2N2S NU SJ F I F H I H 420p2359C19H13F3N2S NH N-F F F H i F 421 2 323 C19Hl5FN2S Nu s I F H I 422 H C 2 365 C21 H20N2025 NU Cl 1 3 H. cl H3C, o 423 H3C'o 2 305 C19H16N2S NU S/ 424 2335C20H18N20S NU Su "" kO 425 1 2 341 C19H14F2N2S NH s-6, N F H"" (J F F 426 i 2 359 C19H13F3N2S NH S F F H / F 427 2 363 C21 H18N2025 NU S/ 0 0 J 428 2 353 C20H17FN20S NU S -6, N F CL, cl CH3 429 I HXI 2 333 C21H20N2S Nu S /CH3 CL, CH3 430 2 311 C17Hl 4N252 NU son H IS . 1 2 373 C20H I 5F3N2S NH S--6, NIF H N 432-2 305 C20H 17FN2 HN CH, NEZ F H I 433-2 287 C20H 18N HN CH3 N H / 434 2 301 C2lH2ON2 HN CH3 NEZ N H I/ CH3 435 2 329 C23H24N2 han HAN/ L H. H, H3C CH3 436 2 306, 308 C19Hl5CIN2 Ho cri N H H I/ 437 2 309 C19H14F2N2 N HN/ H H I/ F -2 327 C19H13F3N2 \/ HAN I F H / F 439 2 333 C21 H20N202 \/ HN CH3 ZOZO H I H3C, 0 440-2 333 C21 H20N202 HN b H C O N zu 441 t_ 2 309 C19H14F2N2 "n- HN F N H I/ F 442-2 327 C 19H 13F3N2 Ho F Han _ F N H I/ F 443 2 331 C21 H 1 8N202 han N N H i 7, 0 OUI 444 Xc 2 301 C21 H20N2 H N N w I e CH3 aha 2 323 C23H18N2 han HAN/ w H/ | HW 2 323 C23H18N2 " HN -N H I I * Analysis was done by LCMS. Number shown is M+l. In all cases mass shown agrees with the expected mass for the compound shown.

The following compounds were prepared according to the general procedure 1 : Example Structure MS 1H-NMR in CDC13 unless Mp (M+H) otherwise noted (8) (°C) APCI 360 7. 90 (IR d) ; 7. 51 (In d) ; 26 N 7. 44-7. 26 (4H, m) ; < 95 (lu d) ; 3. 46 (4H, t) ; 2. 58 (4I-t t) ; 2. 12 (6H, s) ; 1. 91 (4H, quintet) HN 332 7. d) (lR 7. 52 7. d) (lX 55 7. 38-7. 46 (24 quartet) ; 7. 25-7. 35 (1EI, t) ; 7. 14 (1H, 6. 97-6. 86 (3H, m) ; 6. 76-6. 81 (In d) ; 4. 31 (2H, s) 4. 25 (4H, br s) N 480 7. 81 (I d) ; 7. 48 (In d) ; 447 1 \) =\ 7. 34-7. 41 (2H, m) ; 7. 22-7. 28 (2EI ; t) ; 6. 88-6. 92 (1H, d) ; 6. 74-6. 86 (6R m) ; 4. 56 (4X br s) ; 4. 23 (8H, br s) 376 7. 85 (1X d) ; 7. 51 (lH, d) ; 109- 448 7. 26-7. 42 (6EI m) ; 110 7. 7. 08 (2X br s) ; 6. 99-7. 06 (3H, m) ; 4. 60 (4H, br s) HN 280 7. d) (lI-t 7. 52 7. d) (1H, 62-63 59 7. 38-7. 44 (2H, m) ; 7. 25-7. 35 (3H, m) ; 7. 19 (1H, s) ; 7. 14 (1H, s) ; 6. 81 (1H, s) ; 4. 43 (2g s) HN 334 7. 86 (1H, d) ; 7. 52 (1H, d) ; 87-xs 56 8< AÓ 7. 29-7. 42 (3R m) ; 7. 7. 12 (lHs) ; 6. 78 (liez d) ; 0-0 60 (2H, s) ; 6. 41 (liez t) ; 4. 35 (2H, s) ; 3. 79 (6H, s) _ HN > 274 7. d) (1H, 7. 53 (1H, d) (IH, 81-82 63 7. 31-7. 48 (8H, m) ; 7. 18 (lg s) ; 6. 81 (lad) ; ooo 4. 43 (2H, s) ; 4. 10 (1H, br s) HN 320 INDMSO 103- 61 7. 93 (liez d) ; 7. 54 (1H, d) ; 104 7. 17-7. 42 (8H, m) ; o p S 6. 81 (1H, d) ; 6. 22 (1H, t) ; 4. 30 (2H, d) ; 2. 41 (3H, s) H 294 7. 90 (1H, d) ; 7. 51 (1H, d) ; 50-52 73 7. 36-7. 44 (2H, quartet) ; 7. 26-7. 33 (1H, t) ; 7. 09 (1H, O s) ; 6. 72 (1H, d) ; 3. 60 (2H, br m) ; 1. 95 (2R br m) ; 1. 61 (12H, br m) H 342 7. 86 (1H, d) ; 7. 63 (2H, d) ; 89-90 57 N 7. 54 (3g t) ; CF3 7. 43 (2H, quartet) ; O 32 (1H, t) ; 7. 11 (1H, s) ; 6. 77 (lit d) ; 4. 46 (2H, s) 4. 15 (111, br s) HN 364 7. 90 (lek d) ; 7. 53 (lH, d) ; 91-93 449 7. 30-7. 45 (7H, m) ; 7. 03-7. 18 (6HE m) ; +° ° 69 6. 81 (1H, d) ; 4. 39 (2H, s) ; 4. 08 (1H, br s) /==\867. 96 (1H, d) ; 193- 286 7. 96 (1E, d) ; 193- 450 < < 7. 31 7. 55 (8H [, m) ; 195 450 15 (lH, s) ; 6. 83 (lH, d) ; 195 4. 73 (4I-, s) 314 INDMSO 217- 451 8. 22 t ! ; 8. 13 (Ig d) ; 218 0 7. 75 (1TI, d) ; 7. 57 (2H, m) ; 7. 43 (1H, t) H 288 7. 95 (1EI, d) ; 7. 57 (lH, d) ; 84-85 58 N 7. 28-7. 41 (4Et m) ; 7. 12-7. 20 (4H, m) ; 0 6. 87 (lH, d) ; 6. 03 (liez t) ; 4. 28 (2ex, d) ; 2. 36 (3H, s) H 358 7. 85 (lu, d) ; 75-77 452 N 7. 37-7. 53 (5cm) ; 7. 20-7. 31 (3I, m) ; O 7. 14 (in s) ; 6. 90 (IR d) ; OCF3 4. 43 (2H, s) ; 4. 22 (1H, br s H 290 7, 86 (1H, d) ; 7. 55 (lH, d) ; 145- 453 N bo 7. 41-7. 47 (3H, t) ; 147 + \) < 7. 18-7. 34 (4X m) ; 6. 89-7. 02 (3H, m) ; 4. 52 (2H, s) H 366 7. 85 (lH, d) ; 7. 51 (1H, d) ; 93-94 454 N 7. 26-7. 44 (6riz m) ; 7. 17 (lX d) ; O 0 7. 06-7. 13 (3H, m) ; 6. 99-7. 02 (2H, m) ; 6. 95 (1H, s) ; 6. 77 (1H, dd) 4. 40 (2Et s) ; 4. 17 (In s) H 316 7. 86 (1H, d) ; 7. 51 (1H, d) ; 85-86 54 N 7. 26-7. 43 (31Et m) ; 7. 14 (1H, s) ; O \@0 6. 87-6. 92 (2H, m) ; 6. 77-6. 81 (2Et m) ; 5. 96 (2H, s) ; 4. 32 (2EI, s) ; 4. 12 (1H, br s) \ 302 7. 99 (Ig d) ; 7. 52 (1H, d) ; 7. 44-7. 39 (2Et m) ; 7. 32-7. 15 (6Et m) ; 455 6. 89 (1H, s) ; 4. 52 (2EI, s) ; 3. 09 (3K s) ; 2. 37 (3R s) H 316 7. 77 (1I3, d) ; 7. 48-7. 21 (9Et m) ; zu 7. 00 (lX d) ; 6. 70 (1H, dd) ; 456 4. 40 (lu t) ; 4. 13 (llH, br s) 1. 88-1. 78 (2H, m) ; 1. 51-1. 38 (2H, m) ; 0. 97 (3H, t) b 392 7. 87 (IR d) ; 7. 53-7. 53-7. 26 (9X m) ; 7. 16 (il d) ; 6. 77 (lH, dd) ; 457 vo U 3. 50 (2X t) ; 3. 00 (2H, t) 288 7. 76 (IR d) ; 94-95 7. 48-7. 21 (9H ; m) ; 458 6. 99 (lX d) ; 6. 70 (IH, dd) ; 4. 4. 57 (lH, q) ; 4. 07 (lI3, br s) ; 1. 57 3H, d) b 338 7. 09 (4H, m), 7. 09 (3H, m),- 202 om n 6. 96 (1H, d), 6. 30 (2H, m), /< \)-F 4. 26 (sH, s), 2. 26 (3H, s) o 210 334 7. 26 (1H, s), 7. 18 (1H, d), oH ()-/ 7. 09 (s, lH), 7. 07 (lH, s), 7. 02 (11-t s), 6. 9S (lH, s), -6. 97 (2H, s), 6. 96 (lH, s), 6. 87 (lH, d), 6. 36 (lH, s), 6. 34 (lH, d), 4. 2 (2EI, s), 2. 31 (6H, s). 135 362 7. 26 (1H, s), 7. 18 (lH, d), om < 7. 09 (s, 1H), 7. 07 (1H, s), 7. 02 (1H, s), 6. 95 (1H, s), 6. 97 (2H, s), 6. 96 (lH, s), 6. 87 (lH, d), 6. 36 (lH, s), 6. 34 (lH, d), 4. 2 (2EI, s), 1. 3 (9H, s). 146 N 328 7. 61 (d, 1EI), 7. 58 (d, lH), 7. 45 (d, 1H), 7. 39 (d, IM, 7. 37 (s, lH), 7. 34 (s, lH), 7. 32 (s, 1H), 7. 28 (d, 1H), 7. 16 (t, 1EI), 6. 86 (s, lH), 6. 68 (dd, 1H), 4. 35 (s, 3EI), 3. 8 (s, 2H), 1. 31 (s, 9H). 90 M 339 815 (d, 1H), 7. 22 (s, lH), o ()-/ 7. 05 (m, 3H), 6 ; 98 (m, 2H), /< 6. 88 (d, 1gui), 6. 32 (d, 1W, \N F 6. 29 (s, 1H), 4. 3 (s, 2Ei), 2. 3 (s, 3H).

Antiviral activity assays : Screening assays : Anti-herpes simplex virus-1 (HSV) activity is determined in a yield reduction assay utilizing a recombinant HSV (HSV US3 : : pgC-lacZ) which expresses E. coli p-galactosidase (0-gal) under the control of an HSV late gene promoter (Fink, D. J. ; Sternberg, L. R. ; Weber, P. C. ; Mata, M. ; Goins, W. F. ; Glorioso, J. C. Human Gene Therapy 3 : 11-19, 1992). Vero (African Green Monkey kidney) cells are infected at a multiplicity of infection of 0. 01 with the virus, and serial dilutions of the compound in dimethyl sulfoxide (DMSO) are added. The final concentration of DMSO in all wells is 1%. DMSO is added to control wells. The infection is allowed to proceed for 2 days at which time the (3-gal activity in cell lysates is measured. Activity in wells containing compound is compared to control wells and percent inhibition determined. The ECso is defined as the concentration of drug that produces a 50% reduction in 0-gal production relative to control wells.

Anti-human cytomegalovirus (HCMV) activity is determined in a yield reduction assay utilizing a recombinant HCMV (RC256) that produces p-gal (Spaete, R. R. ; Mocarski, E. S. Proceedings of the National Academy of Sciences USA 84 : 7213-7217, 1987). Primary human diploid fibroblasts (EIFF cells) are infected at an moi of 0. 01 with RC256, and serial dilutions of the compound in DMSO are added.

The final concentration of DMSO in all wells is 1%. The infection is allowed to proceed for 7 days at which time the (3-gal activity in cell lysates is measured.

Activity in wells containing compound is compared to control wells and percent inhibition determined. The ECso is defined as the concentration of compound that produces a 50% reduction in (3-gal production relative to control wells. TCso is defined as concentration of compound that produces cytotoxicity in 50% of uninfected cells.

Secondary yield reduction assays : To determine the activity of compounds against HSV, Vero cells are plated in 6 well dishes at a density of 5 x 105 cells/well. Cells are infected at a multiplicity of infection of 0. 01 with HSV (strain Synl7+). 30pL of one of six threefold serial dilutions of test compound in DMSO is added to each well at the time of infection. The plates are returned to a 37°C incubator and the infection allowed to proceed for 2 days. Aliquots of the supernatant are harvested, and the virus titer determined. Vero cells in 24 well plates are infected with threefold serial dilutions of supernatant. The virus is allowed to adsorb to the monolayer for 1. 5 hours, after which it is aspirated and replaced with growth medium containing 0. 5% methylcellulose. Plaques are allowed to develop for 5 days, at which time the medium aspirated and the monolayer stained with crystal violet. The plaques are enumerated under low power magnification. Percent inhibition is determined by comparison with the titer from cells infected in the presence of DMSO alone.

To determine the activity of compounds against CMV, HFF cells, plated in 24 well plates at 1 x 105 cells/well, are infected with CMV (strain AD 169) at an moi of 0. 01. 10 u, L of one of six threefold dilutions of test compound in DMSO is added to each well at the time of infection. The plates are returned to a 37°C incubator and the infection allowed to proceed for 7 days. Aliquots of the supernatant of infected cells are harvested and the virus titer determined. HFF cells in 24 well plates are infected with threefold serial dilutions of supernatant. The virus is allowed to adsorb to the cells for 2 hours, at which time the inoculum is aspirated and replaced with growth medium containing 0. 5% methylcellulose. The plaques are allowed to develop for 7- 10 days, at which time the medium is aspirated and the monolayer stained with crystal violet. The plaques are enumerated under low power magnification. Percent inhibition is determined by comparison with the titer from cells infected in the presence of DMSO alone.

Cellular toxicity assays : Cellular toxicity is measured in ME cells. Cells are plated in 96 well plates at 1x104 cells/well. Serial dilutions of compounds are added to the wells in DMSO, with the final concentration of DMSO in all wells at 1%, in a total volume of 200pL. The plates are maintained in a 37°C incubator for 7 days. 5011L of a solution of XTT (sodium-3' [1- (phenyl-amino-carbonyl)-3,-tetrazolium]-bis (bis (4- methoxy-6-nitro)-benzene sulfonic acid hydrate) (3 x 10-4 mg/ml) is added to each well, and the plates returned to the incubator for 4 hours, after which the A450 (absorbance at wavelength of 450 nm) for each well is measured in a plate reader.

(Roehm, N. W., et al J. Immunol. Meth. 142 : 257-265, 1991). Toxicity is determined by comparison of the OD (optical density) of a well containing compound to the OD of wells containing DMSO only.

The effect of test compounds on cellular DNA synthesis is measured in a 14C- thymidine incorporation assay, utilizing scintillation proximity assay technology.

Cells are plated at 2 x 104 cells/well in Amersham Cytostar 96 well scintillating microplates. The following day, serial dilutions of test compounds in DMSO are added to the wells, along with 0. 1 Ci/well of [methyl-14C]-thymidine (specific activity 50-62mCi/mmol). The plates are counted immediately in a tbeta scintillation counter (Wallac), to determine background, then placed in a 37°C incubator for 7 days. The plates are removed from the incubator at intervals and the thymidine incorporation into the cellular DNA determined by scintillation counting.

Percent inhibition is determined by comparing 14C incorporation in wells containing test compound to incorporation in wells containing DMSO only.

Table 3 contains the results of the antiviral efficacy (HSV : ECso, TC50 and TI) screening results, where TI is the therapeutic index (TCso/ECso).

TABLE 3 Antiviral Efficacy in a Yield Reduction Assay (HSV-1) Antiviral Efficacy (Vero Cells) Example EC50 (µM) TC50 (µM) TI (EC50/TC50) 60 0. 5 >100 >200 57 0. 81 >100 >124 56 0. 7 >100 >143 208 0. 26 >100 >385 217 0. 32 >100 >313 139 0. 4 >100 >250 150 0. 85 >100 >118 93 1. 3 >100 >77 Reference 0. 2 >100 >500 Agent (Acyclovir) Table 4 contains the results of the antiviral efficacy (HSV : ECso, TCso and TI) screening results, where TI is the therapeutic index (TC5o/EC50).

TABLE4 Antiviral Efficacy in a Yield Reduction Assay (CMV) Antiviral Efficacy (HFF Cells) Example EC50. (µM) TC50 (µM) TI (EC50/TC50) 61 2. 9 >100 >35 57 1. 7 >100 >59 65 3. 0 >100 >33 60 1. 3 >100 >77 Reference 2. 6 >100 >39 Agent (Ganciclovir) Tables 3 and 4 indicates that the compounds of the present invention have good to excellent activity in HSV infected cells from HSV pathogenecity at uM to sub-jjM concentrations.

While the forms of the invention herein disclosed constitute presently preferred embodiments, many others are possible. It is not intended herein to mention all of the possible equivalent forms or ramifications of the invention. It is understood that the terms used herein are merely descriptive, rather than limiting, and that various changes may be made without departing from the spirit or scope of the invention.