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Document Type and Number:
Japanese Patent JP2010522147
Kind Code:
Hydroxy quinoline amino compounds (I) and their enantiomers are new. Hydroxy quinoline amino compounds of formula (I) and their enantiomers are new. R 1, R 2H, 1-10C alkyl, halo group comprising F, Br, Cl or a group -O-R, one of R 1 and R 2 is phenyl compounds of formula (a) having asymmetric carbon; R : 1-10C alkyl, 4-8C cycloalkyl, 1-10C alcohol, 4-8C heterocycloalkyl which contains heteroatoms of N, O or S, 2-10C alkenyl or alkynyl, (hetero)aryl, alkylphenyl or 1-10C alkyl, or alkanoyl phenyl having 1-3 C atoms of alkonyl, phenyl optionally substituted with 1-2 halo atoms of F, Br, I or Cl or -CF 3, R-NO 2 (where R is 1-10C alkyl or 5-methylene-8-hydroxyquinole); R 3-R 7H, 1-10C alkyl, 4-8C cycloalkyl, 2-10C alkenyl, 2-10C alkynyl, -CF 3, -O-R (where R is 5-methylene-8-hydroxyquinole); X, Y 1H, 1-10C alkyl, aryl, -OH, Cl, Br, I, F, -CF 3, R-NH 2, -CN, R-NO 2, R-COOH or -COOR, where R is 1-10C alkyl, either in the case one of R 1 and R 2 is Y 1-N-Y 1 or Y 1 is a -(CH 2) n-, aryl optionally substituted with 1 or 2 atoms of halo comprising F, Br, Cl, or 1-10C alkyl, 4-8C heterocycloalkyl, and where Y 1 is 5-methylene-8-hydroxyquinole, the other atoms is H, or in the case one of R 1 and R 2 is -(CH 2) n-naphthalene, where the naphthalene is optionally substituted with 1-10C alkyl, 4-8C cycloalkyl, 2-10C alkenyl, 2-10C alkynyl, 1-10C alkanoyl, -CF 3 or -O-R, where R is 1-10C alkyl, ant the other is H, 5-methylene-8-hydroxyquinole or t-butyloxycarbonyl, or R 1 and R 2 form a 4-8C cyclic aliphatic ring optionally substituted with 1-6C alkyl or -O-R, where R is 1-10C alkyl, or aryl, possibly H, 1-6C alkyl optionally substituted with F, Br or Cl, or one of R 1 and R 2 form 5-6 membered cyclic polyamine or unsubstituted piperazine or which one of the carbon atom in the cycle is substituted with 1-6C alkyl and/or in which one of the N atom is not a part in the group -CH 2-NR 1R 2 or substituted by 5-methylene-8-hydroxyquinole, or R 1 and R 2 form a polyazamacrocycle (cyclam) comprising 1,4,8,12-tetraazacyclopentadecan or 1,4,8,11-tetraazacyclotetradecane (both are unsubstituted), where at least one of the N of the cycle in position 1, 4 and 8 is replaced with t-butoxycarbonyl, 5-methylene-8-hydroxyquinole or -(CH 2) n-phenyl-(CH 2) n-Z; n : 1-10; and Z : one of N of a 1,4,8,12-tetraazacyclopentadecane or a 1,4,8,11- tetraazacyclotetradecane in which the other atoms N of the cycle in position 1,4 and 8 are optionally substituted with t-butoxycarbonyl. [Image] [Image] ACTIVITY : Cytostatic. MECHANISM OF ACTION : None given. (I) were tested for cytotoxic effect in KB cell line. The medium inhibitory concentration value of 5,5'-(benzylazanediyl)bis(methylene)diquinolein-8-ol was 0.0015/0.005 mu M.

Application Number:
Publication Date:
July 01, 2010
Filing Date:
March 25, 2008
Export Citation:
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International Classes:
C07D215/26; A61K31/4709; A61P35/00; A61P35/04; C07D215/38; C07D401/06; C07D401/12; C07D407/12; C07D409/12
Domestic Patent References:
Foreign References:
Other References:
JPN6013018323; Bioorganic & Medicinal Chemistry Letters Vol.16, 2006, pp.5988-5992
JPN6013018326; Journal of Heterocyclic Chemistry Vol.3, 1966, pp.275-277
JPN6013018328; Journal of Organic Chemistry Vol.26, 1961, pp.4078-4083
JPN6013018330; Materials Letters Vol.60, 2006, pp.3342-3345
JPN6013018332; Journal of Neurochemistry Vol.95, 2005, pp.68-78
JPN6013056903; Journal of the Indian Chemical Society Vol.66, No.5, 1989, pp.319-321
Attorney, Agent or Firm:
田中 光雄
山崎 宏
元山 忠行
冨田 憲史
西野 満
稲井 史生