IP Library › Patent Application 13377745
Patent Application
App. No. 13/377,745

COMPOUNDS USEFUL FOR TREATING CANCER

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Patent No.
US None
App. No.
13/377,745
Abstract

The present invention relates to compound (I) wherein: means a pyridazine, a pyrimidine or a pyrazine group, R independently represent a hydrogen atom, a halogen atom or a group chosen among a CN group, a hydroxyl group, a COOR 1 group, a (C 1 -C 3 )fluoroalkyl group, a (C 1 -C 3 )fluoroalkoxy group, a NO 2 group, a NR 1 R 2 group, a (C 1 -C 4 )alkoxy group, a phenoxy group and a (C 1 -C 3 )alkyl group, said alkyl being optionally mono-substituted by a hydroxyl group, n is 1, 2 or 3, n is 1 or 2, R is a hydrogen atom, a halogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a hydroxyl group, a COOR 1 group, a NO 2 group, a NR 1 R 2 group, a morpholinyl or a morpholino group, a N-methylpiperazinyl group, a (C 1 -C 3 )fluoroalkyl group, a (C1-C4)alkoxy group and a CN group, Z is N or C, Y is N or C, X is N or C, W is N or C, T is N or C, U is N or C, for use as an agent for preventing, inhibiting or treating cancer. Some of said compounds are new and also form part of the invention.

Claims (369)

1 . A method of preventing, inhibiting, or treating cancer comprising contacting a cell with at least one compound of formula (I):

wherein:

is an aromatic ring wherein V is C or N and when V is N, V is in an ortho, meta or para position with respect to Z such that the ring respectively forms a pyridazine, a pyrimidine, or a pyrazine,

R independently represents a hydrogen atom, a halogen atom or a group chosen among a —CN group, a hydroxyl group, a —COOR 1 group, a (C 1 -C 3 )fluoroalkyl group, a (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, a —NR 1 R 2 group, a (C 1 -C 4 )alkoxy group, a phenoxy group and a (C 1 -C 3 )alkyl group, said alkyl group being optionally mono-substituted by a hydroxyl group,

R 1 and R 2 are independently a hydrogen atom or a (C 1 -C 3 )alkyl group,

n is 1, 2 or 3,

n′ is 1 or 2,

R′ is a hydrogen atom, a halogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a hydroxyl group, a —COOR 1 group, a —NO 2 group, a —NR 1 R 2 group, a morpholinyl or a morpholino group, a N-methylpiperazinyl group, a (C 1 -C 3 )fluoroalkyl group, a (C 1 -C 4 )alkoxy group and a —CN group,

R″ is a hydrogen atom or a (C 1 -C 4 )alkyl group,

Z is N or C,

Y is N or C,

X is Nor C,

W is N or C,

T is N or C,

U is N or C,

and wherein at most four of the groups V, T, U, Z, Y, X and W are N,

and at least one of the groups T, U, Y, X and W is N,

or a pharmaceutically acceptable salt thereof.

2 . The method of claim 1 , wherein

Z is N, V is C, Y is N, X is C, T is C, U is C and W is C,

Z is C, V is C, Y is N, X is C, T is C, U is C and W is C,

Z is N, V is C, Y is C, X is N, T is C, U is C and W is C,

Z is N, V is C, Y is C, X is C, T is C, U is C and W is N,

Z is N, V is N and is in the para position with respect to Z, Y is N, X is C, T is C, U is C and W is C

Z is C, V is N and is in the para position with respect to Z, Y is C, X is N, T is C, U is C and W is C,

Z is C, V is N and is in the meta position with respect to Z and is in a para position with respect to the bond linked to NR″, Y is N, X is C, T is C, U is C and W is C,

Z is C, V is N and is in the meta position with respect to Z and is in the para position with respect to of the bond linked to NR″, Y is C, X is N, T is C, U is C and W is C,

Z is C, V is C, Y is C, X is N, T is C, U is C and W is C,

Z is C, V is C, Y is N, X is N, T is C, U is C and W is C,

Z is N, V is N and is in the meta position with respect to Z and in an ortho position with respect to the bond linked to NR″, Y is N, X is C, T is C, U is C and W is C,

Z is N, V is N and is in the para position with respect to Z, Y is C, X is C, T is C, U is C and W is N,

Z is N, V is N and is in the para position with respect to Z, Y is C, X is N, T is C, U is C and W is C,

Z is N, V is C, Y is N, X is N, T is C, U is C and W is C,

Z is N, V is N and is in the meta position with respect to Z and is in the ortho position with respect to of the bond linked to NR″, Y is N, X is N, T is C, U is C and W is C,

Z is C, V is C, Y is C, X is C, T is N, U is C and W is C,

Z is N, V is C, Y is C, X is C, T is N, U is C and W is C, or

Z is N, V is C, Y is C, X is C, T is C, U is N and W is C.

3 . The method of claim 1 , wherein

Z is N, V is C, Y is N, X is C, T is C, U is C and W is C,

Z is N, V is N and is in the para position with respect to Z, Y is N, X is C, T is C, U is C and W is C,

Z is C, V is C, Y is C, X is C, T is N, U is C and W is C, or

Z is N, V is C, Y is C, X is C, T is C, U is N and W is C.

4 . The method of claim 1 , wherein the compound of formula (I) is selected from the group consisting of

wherein:

R independently represents a hydrogen atom, a halogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a —CN group, a hydroxyl group, a —COOR 1 group, a (C 1 -C 3 )fluoroalkyl group, a —NO 2 group, a —NR 1 R 2 group and a (C 1 -C 3 )alkoxy group,

R′ is a hydrogen atom, a halogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a —NO 2 group, a (C 1 -C 3 )alkoxy group and a —NR 1 R 2 group,

R 1 and R 2 are a hydrogen atom or a (C 1 -C 3 )alkyl group,

wherein:

R independently represents a hydrogen atom, a halogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a —NR 1 R 2 group, a (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, a phenoxy group and a (C 1 -C 4 )alkoxy group,

R 1 and R 2 are independently a hydrogen atom or a (C 1 -C 3 )alkyl group,

R′ is a hydrogen atom, a halogen atom or a group chosen among a (C 1 -C 3 )alkyl group and a (C 1 -C 4 )alkoxy group,

wherein:

R independently represents a hydrogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a (C 1 -C 3 )fluoroalkyl group, a —NR 1 R 2 group, a —COOR 1 group, a—NO 2 group and a (C 1 -C 3 )alkoxy group,

R′ is a hydrogen atom,

R 1 and R 2 are independently a hydrogen atom or a (C t —C 3 )alkyl group,

wherein:

R independently represents a hydrogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a (C 1 -C 3 )fluoroalkyl group and a (C 1 -C 3 )alkoxy group,

R′ is a hydrogen atom,

wherein:

R is a hydrogen atom,

R′ is a hydrogen atom, a halogen atom or a group chosen among a (C 1 -C 3 )alkyl group and a (C 1 -C 3 )alkoxy group,

wherein:

R is a hydrogen atom,

R′ is a hydrogen atom,

wherein:

R is a hydrogen atom,

R′ is a hydrogen atom or a halogen atom,

wherein:

R is a hydrogen atom,

R′ is a hydrogen atom,

wherein:

R independently represents a hydrogen atom or a group chosen among a (C 1 -C 3 )fluoroalkoxy group and a (C 1 -C 3 )alkoxy group,

R′ is a hydrogen atom,

wherein:

R independently represents a hydrogen atom or a group chosen among a (C 1 -C 3 )fluoroalkoxy group and a (C 1 -C 3 )alkyl group,

R′ is a hydrogen atom,

wherein:

R is a hydrogen atom,

R′ is a hydrogen atom, a halogen atom or a (C 1 -C 3 )alkyl group,

wherein:

R is a hydrogen atom,

R′ is a hydrogen atom,

wherein:

R is a hydrogen atom,

R′ is a hydrogen atom,

wherein:

R independently represents a hydrogen atom, a halogen atom or a group chosen among, a —NO 2 group, a —CN group and a (C 1 -C 3 )alkyl group, said alkyl being optionally mono-substituted by a hydroxyl group,

R′ is a hydrogen atom, a halogen atom or a (C 1 -C 3 )fluoroalkyl group,

wherein:

R is a hydrogen atom,

R′ is a hydrogen atom,

wherein:

R independently represents a hydrogen atom, a (C 1 -C 3 )alkoxy group or a (C 1 -C 3 )fluoroalkoxy group,

R′ is a hydrogen atom or a group chosen among a —NR 1 R 2 group, a N-methylpiperazinyl group, a (C 1 -C 3 )alkoxy group and a morpholino group,

R 1 and R 2 are independently a hydrogen atom or a (C 1 -C 3 )alkyl group,

wherein:

R independently represents a hydrogen atom or a (C 1 -C 3 )alkyl group,

R′ is a hydrogen atom or a group chosen among a —NR 1 R 2 group, a morpholino group and a (C 1 -C 3 )alkoxy group,

R 1 and R 2 are independently a hydrogen atom or a (C 1 -C 3 )alkyl group,

wherein:

R independently represents a hydrogen atom, a (C 1 -C 3 )alkyl group or a (C 1 -C 3 )fluoroalkyl group,

R′ is a hydrogen atom or a (C 1 -C 3 )alkyl group,

or (19) a pharmaceutically acceptable salt thereof.

5 . The method of claim 1 wherein the compound of formula (I) is selected from the group consisting of:

wherein:

R independently represents a hydrogen atom, a halogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a—CN group, a —COOR 1 group and a (C 1 -C 3 )fluoroalkyl group,

R 1 is a hydrogen atom or a (C 1 -C 3 )alkyl group,

R′ is a hydrogen atom, a halogen atom or a (C 1 -C 3 )alkyl group,

wherein:

R is a hydrogen atom,

R′ is a hydrogen atom or a halogen atom,

wherein:

R is a (C 1 -C 3 )fluoroalkoxy group,

wherein:

R is independently a hydrogen atom or a (C 1 -C 4 )alkyl group,

or (5) a pharmaceutically acceptable salt thereof.

6 . The method of claim 1 , wherein the compound of formula (I) has the formula (Iq)

wherein

n is 1 or 2,

with the proviso that

R′ and R are not simultaneously a hydrogen atom,

when R′ is a hydrogen atom, R is not a —NO 2 group or a —NH 2 group,

when n is 2 and R′ is a hydrogen atom, R is not a COOC 2 H 5 group or a chlorine atom,

or a pharmaceutically acceptable salt thereof.

7 . The method of claim 1 , wherein the compound of formula (I) has the formula (Iee)

or a pharmaceutically acceptable salt thereof,

with the exclusion of the following compound

and with the exclusion of compounds wherein R is a —NO 2 group or a —NH 2 group when R′ is a hydrogen or a methyl group.

8 . A method of preventing, inhibiting, or treating cancer comprising contacting a cell with at least one compound chosen from:

(1) (8-Chloro-quinolin-2-yl)-pyridin-2-yl-amine

(2) 2-(Quinolin-2-ylamino)-isonicotinic acid

(3) (4-Methyl-pyridin-2-yl)-quinolin-2-yl-amine

(4) Pyridin-2-yl-quinolin-2-yl-amine

(5) 2-(8-Chloro-quinolin-2-ylamino)-isonicotinic acid

(6) (8-Chloro-quinolin-2-yl)-(4-methyl-pyridin-2-yl)-amine

(7) 6-(Quinolin-2-ylamino)-nicotinonitrile

(8) Quinolin-2-yl-(4-trifluoromethoxy-phenyl)-amine

(9) Pyridin-2-yl-quinolin-3-yl-amine

(10) (3-Methoxy-pyridin-2-yl)-quinolin-3-yl-amine

(11) Quinolin-3-yl-(5-trifluoromethyl-pyridin-2-yl)-amine

(12) (5-Nitro-pyridin-2-yl)-quinolin-3-yl-amine

(13) (5-Methyl-pyridin-2-yl)-quinolin-3-yl-amine

(14) 2-(Quinolin-3-ylamino)-isonicotinic acid

(15) Quinolin-6-yl-(5-trifluoromethyl-pyridin-2-yl)-amine

(16) (6-Methyl-pyridin-2-yl)-quinolin-6-yl-amine

(17) N-(6-methylpyridin-2-yl)quinolin-2-amine

(18) 8-chloro-N-(6-methylpyridin-2-yl)quinolin-2-amine

(19) 4-methyl-N-(pyridin-2-yl)quinolin-2-amine

(20) 4-methyl-N-(4-methylpyridin-2-yl)quinolin-2-amine

(21) 3-methyl-N-(4-methylpyridin-2-yl)quinolin-2-amine

(22) 3-methyl-N-(pyridin-2-yl)quinolin-2-amine

(23) 6-((4-methylquinolin-2-yl)amino)nicotinonitrile

(24) 6-((3-methylquinolin-2-yl)amino)nicotinonitrile

(25) 6-chloro-N-(4-methylpyridin-2-yl)quinolin-2-amine

(26) 6-chloro-N-(6-methylpyridin-2-yl)quinolin-2-amine

(27) 4-methyl-N-(5-nitropyridin-2-yl)quinolin-2-amine

(28) N-(3-nitropyridin-2-yl)quinolin-2-amine

(29) 8-chloro-N-(3-nitropyridin-2-yl)quinolin-2-amine

(30) 2-((4-methylquinolin-2-yl)amino)nicotinonitrile

(31) N-(3-methylpyridin-2-yl)quinolin-2-amine

(32) N-(5-methylpyridin-2-yl)quinolin-2-amine

(33) 2-(quinolin-2-ylamino)isonicotinonitrile

(34) N-(5-(trifluoromethyl)pyridin-2-yl)quinolin-2-amine

(35) 8-chloro-N-(3-methylpyridin-2-yl)quinolin-2-amine

(36) 8-chloro-N-(5-methylpyridin-2-yl)quinolin-2-amine

(37) 8-chloro-N-(5-(trifluoromethyl)pyridin-2-yl)quinolin-2-amine

(38) N-(3-methoxypyridin-2-yl)quinolin-2-amine

(39) N-(5-nitropyridin-2-yl)quinolin-2-amine

(40) 6-((8-chloroquinolin-2-yl)amino)nicotinonitrile

(41) N-(5-fluoropyridin-2-yl)quinolin-2-amine

(42) N-(6-(trifluoromethyl)pyridin-2-yl)quinolin-2-amine

(43) 8-chloro-N-(5-fluoropyridin-2-yl)quinolin-2-amine

(44) 2-((8-chloroquinolin-2-yl)amino)nicotinic acid

(45) 4-methyl-N-(6-methylpyridin-2-yl)quinolin-2-amine

(46) 3-methyl-N-(6-methylpyridin-2-yl)quinolin-2-amine

(47) 5-cyano-2-(quinolin-2-ylamino)pyridin-1-ium chloride

(48) 2-((8-chloroquinolin-2-yl)amino)-4-methylpyridin-1-ium chloride

(49) 8-chloro-N-(4-ethylpyridin-2-yl)quinolin-2-amine

(50) 8-chloro-N-(6-ethylpyridin-2-yl)quinolin-2-amine

(51) 8-chloro-N-(4,6-dimethylpyridin-2-yl)quinolin-2-amine

(52) 6-((8-chloroquinolin-2-yl)amino)-2-methylnicotinonitrile

(53) 8-chloro-N-(4-chloropyridin-2-yl)quinolin-2-amine

(54) 8-methyl-N-(4-methylpyridin-2-yl)quinolin-2-amine

(55) N-(5-bromo-4-methylpyridin-2-yl)-8-chloroquinolin-2-amine

(56) 8-chloro-N-(3-ethyl-6-methylpyridin-2-yl)quinolin-2-amine

(57) 8-fluoro-N-(4-methylpyridin-2-yl)quinolin-2-amine

(58) 8-bromo-N-(4-methylpyridin-2-yl)quinolin-2-amine

(59) methyl 6-(quinolin-2-ylamino)nicotinate

(60) methyl 6-[(8-chloroquinolin-2-yl)amino]pyridine-3-carboxylate

(61) methyl 6-[(3-methylquinolin-2-yl)amino]pyridine-3-carboxylate

(62) methyl 2-[(8-chloroquinolin-2-yl)amino]pyridine-3-carboxylate

(63) 8-methoxy-N-(4-methylpyridin-2-yl)quinolin-2-amine

(64) N-(4-methylpyridin-2-yl)-5-nitroquinolin-2-amine

(65) 2-N-(4-methylpyridin-2-yl)quinoline-2,8-diamine

(66) 2-N-(4-methylpyridin-2-yl)quinoline-2,5-diamine

(67) methyl 6-[(4-methylquinolin-2-yl)amino]pyridine-3-carboxylate

(68) 8-chloro-N-[4-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine

(69) 2-[(8-chloroquinolin-2-yl)amino]pyridin-3-ol

(70) 8-chloro-N-[6-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine

(71) 6-chloro-N-(5-fluoropyridin-2-yl)quinolin-2-amine

(72) N-(6-ethylpyridin-2-yl)-3-methylquinolin-2-amine

(73) N-(5-fluoropyridin-2-yl)-3-methylquinolin-2-amine

(74) 3-methyl-N-[5-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine

(75) 4-N-(8-chloroquinolin-2-yl)-1-N,1-N-dimethylbenzene-1,4-diamine

(76) N-(4-methoxyphenyl)quinolin-2-amine

(77) 8-chloro-N-(4-methoxyphenyl)quinolin-2-amine

(78) 4-methyl-N-[4-(trifluoromethoxy)phenyl]quinolin-2-amine

(79) N-(4-methoxyphenyl)-3-methylquinolin-2-amine

(80) 3-methyl-N-[4-(trifluoromethoxy)phenyl]quinolin-2-amine

(81) 1-N,1-N-dimethyl-4-N-(3-methylquinolin-2-yl)benzene-1,4-diamine

(82) N-[2-methyl-4-(trifluoromethoxy)phenyl]quinolin-2-amine

(83) N-[3-(trifluoromethoxy)phenyl]quinolin-2-amine

(84) N-[2-(trifluoromethoxy)phenyl]quinolin-2-amine

(85) N-(4-nitrophenyl)quinolin-2-amine

(86) N-(3-fluorophenyl)quinolin-2-amine

(87) 8-chloro-N-[3-(trifluoromethoxy)phenyl]quinolin-2-amine

(88) 8-chloro-N-(3-fluorophenyl)quinolin-2-amine

(89) 2-{[4-(trifluoromethoxy)phenyl]amino}quinolin-1-ium chloride

(90) 8-chloro-N-[4-(trifluoromethoxy)phenyl]quinolin-2-amine

(91) 3-methyl-N-[2-methyl-4-(trifluoromethoxy)phenyl]quinolin-2-amine

(92) 3-methyl-N-[3-(trifluoromethoxy)phenyl]quinolin-2-amine

(93) 3-methyl-N-[2-(trifluoromethoxy)phenyl]quinolin-2-amine

(94) 8-chloro-N-[2-methyl-4-(trifluoromethoxy)phenyl]quinolin-2-amine

(95) 3-methyl-2-{[4-(trifluoromethoxy)phenyl]amino}quinolin-1-ium chloride

(96) 6-chloro-N-(4-(trifluoromethoxy)phenyl)quinolin-2-amine

(97) 4-methyl-2-{[4-(trifluoromethoxy)phenyl]amino}quinolin-1-ium chloride

(98) 8-bromo-N-[4-(trifluoromethoxy)phenyl]quinolin-2-amine

(99) 8-fluoro-N-[4-(trifluoromethoxy)phenyl]quinolin-2-amine

(100) 8-methyl-N-[4-(trifluoromethoxy)phenyl]quinolin-2-amine

(101) N-(4-butoxyphenyl)-8-chloroquinolin-2-amine

(102) N-(4-phenoxyphenyl)quinolin-2-amine

(103) 8-methoxy-N-[4-(trifluoromethoxy)phenyl]quinolin-2-amine

(104) 8-chloro-N-[3-chloro-4-(trifluoromethoxy)phenyl]quinolin-2-amine

(105) N-(6-methylpyridin-2-yl)quinolin-3-amine

(106) N-(3-nitropyridin-2-yl)quinolin-3-amine

(107) N-(5-methylpyridin-2-yl)quinolin-6-amine

(108) N-(3-methoxypyridin-2-yl)quinolin-6-amine

(109) 6-chloro-N-(pyrazin-2-yl)quinolin-2-amine

(110) 8-bromo-N-(pyrazin-2-yl)quinolin-2-amine

(111) 8-methyl-N-(pyrazin-2-yl)quinolin-2-amine

(112) 8-chloro-N-(pyrazin-2-yl)quinolin-2-amine

(113) N-(pyrazin-2-yl)quinolin-2-amine

(114) 4-methyl-N-(pyrazin-2-yl)quinolin-2-amine

(115) 3-methyl-N-(pyrazin-2-yl)quinolin-2-amine

(116) 8-fluoro-N-(pyrazin-2-yl)quinolin-2-amine

(117) 8-methoxy-N-(pyrazin-2-yl)quinolin-2-amine

(118) N-(pyridin-3-yl)quinolin-3-amine

(119) 8-chloro-N-(pyridin-4-yl)quinolin-2-amine

(120) N-(pyridin-4-yl)quinolin-2-amine

(121) N-(pyridin-4-yl)quinolin-3-amine

(122) N-[4-(trifluoromethoxy)phenyl]quinolin-3-amine

(123) N-(4-methoxyphenyl)quinolin-3-amine

(124) N-[4-(trifluoromethoxy)phenyl]quinoxalin-2-amine

(125) N-[2-methyl-4-(trifluoromethoxy)phenyl]quinoxalin-2-amine

(126) N-[3-(trifluoromethoxy)phenyl]quinoxalin-2-amine

(127) N-[2-(trifluoromethoxy)phenyl]quinoxalin-2-amine

(128) N-(pyrimidin-2-yl)quinolin-2-amine

(129) 8-chloro-N-(pyrimidin-2-yl)quinolin-2-amine

(130) 4-methyl-N-(pyrimidin-2-yl)quinolin-2-amine

(131) N-(pyrazin-2-yl)quinolin-6-amine

(132) N-(pyrazin-2-yl)quinolin-3-amine

(133) 6-methyl-N-(naphthalen-2-yl)pyridin-2-amine

(134) N-(naphthalen-2-yl)pyridin-2-amine

(135) N-(pyridin-2-yl)quinoxalin-2-amine

(136) N-(4-methylpyridin-2-yl)quinoxalin-2-amine

(137) 6-(quinoxalin-2-ylamino)pyridine-3-carbonitrile

(138) N-(6-methylpyridin-2-yl)quinoxalin-2-amine

(139) N-(4-methylpyridin-2-yl)-3-(trifluoromethyl)quinoxalin-2-amine

(140) N-(3,5-dichloro-4-methylpyridin-2-yl)quinoxalin-2-amine

(141) N-(4-methyl-3-nitropyridin-2-yl)quinoxalin-2-amine

(142) N-(pyrimidin-2-yl)quinoxalin-2-amine

(143) 4-N,4-N-dimethyl-7-N-[4-(trifluoromethoxy)phenyl]quinoline-4,7-diamine

(144) 4-(morpholin-4-yl)-N-[4-(trifluoromethoxy)phenyl]quinolin-7-amine

(145) 4-methoxy-N-(pyridin-2-yl)quinolin-7-amine

(146) 4-methoxy-N-(4-methylpyridin-2-yl)quinolin-7-amine

(147) 4-N,4-N-dimethyl-7-N-(4-methylpyridin-2-yl)quinoline-4,7-diamine

(148) 5,8-dimethyl-N-(5-methylpyridin-2-yl)isoquinolin-6-amine

(149) 5,8-dimethyl-N-(5-methylpyridin-2-yl)isoquinolin-6-amine

(150) N-(4-methylpyridin-2-yl)-8-nitroquinolin-2-amine

(151) 6-chloro-N-(6-ethylpyridin-2-yl)quinolin-2-amine

(152) 6-chloro-N-(5-methylpyridin-2-yl)quinolin-2-amine

(153) 6-chloro-N-[5-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine

(154) N2-(8-chloroquinolin-2-yl)-4-methylpyridine-2,3-diamine

(155) N-(4-butoxyphenyl)-3-methylquinolin-2-amine

(156) 4-N-(6-chloroquinolin-2-yl)-1-N,1-N-dimethylbenzene-1,4-diamine

(157) 8-chloro-N-(3-chloro-4-methoxyphenyl)quinolin-2-amine

(158) N1-(8-chloroquinolin-2-yl)-4-(trifluoromethoxy)benzene-1,2-diamine

(159) 2-{4-[(8-chloroquinolin-2-yl)amino]phenoxy}ethan-1-ol

(160) 6-chloro-N-(4-methylpyridin-2-yl)quinoxalin-2-amine

(161) N-(4-ethylpyridin-2-yl)quinoxalin-2-amine

(162) N-(5-bromo-4-methylpyridin-2-yl)quinoxalin-2-amine

(163) N-(4,6-dimethylpyridin-2-yl)quinoxalin-2-amine

(164) [2-(quinoxalin-2-ylamino)pyridin-4-yl]methanol

(165) N-(4-methyl-5-nitropyridin-2-yl)quinoxalin-2-amine

(166) N-(4-methoxyphenyl)-4-(4-methylpiperazin-1-yl)quinolin-7-amine

(167) 4-methoxy-N-[4-(trifluoromethoxy)phenyl]quinolin-7-amine

(168) N-(4-methylpyridin-2-yl)-4-(morpholin-4-yl)quinolin-7-amine

and a pharmaceutically acceptable salt thereof.

9 . The method of claim 8 , wherein the compound is chosen among the compounds (1), (2), (5)-(7), (10)-(16), (18), (21)-(44), (46)-(74), (105)-(108), (124)-(130), (135)-(141), (145)-(147), (150)-(154), (159), (160)-(165), and (168) and the pharmaceutically acceptable salts are hydrobromide, tartrate, citrate, trifluoroacetate, ascorbate, hydrochloride, tartrate, triflate, maleate, mesylate, formate, acetate and fumarate.

10 . The method of claim 1 , wherein compound is in a pharmaceutical composition.

11 . The method of claim 9 , wherein the compound is in a pharmaceutical composition.

12 . The method of claim 1 , further comprising a step of administering the compound to a patient in need of cancer treatment.

13 . The method of claim 12 , comprising orally administering the compound.

14 . The method of claim 8 , further comprising a step of administering the compound to a patient in need of cancer treatment.

15 . The method of claim 14 , comprising orally administering the compound.

16 . A compound selected from the group consisting of:

wherein

R independently represents a hydrogen atom, a halogen atom or a group chosen among a —CN group, a hydroxyl group, a —COOR 1 group, a (C 1 -C 3 )fluoroalkyl group, a (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, a —NR 1 R 2 group, a (C 1 -C 4 )alkoxy group, a phenoxy group and a (C 1 -C 3 )alkyl group, said alkyl group being optionally mono-substituted by a hydroxyl group,

R 1 and R 2 are independently a hydrogen atom or a (C 1 -C 3 )alkyl group,

n is 1 or 2,

n′ is 1 or 2,

R′ is a hydrogen atom, a halogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a hydroxyl group, a —COOR 1 group, a —NO 2 group, a —NR 1 R 2 group, a morpholinyl or a morpholino group, a N-methylpiperazinyl group, a (C 1 -C 3 )fluoroalkyl group, a (C 1 -C 4 )alkoxy group and a —CN group,

R″ is a hydrogen atom or a (C 1 -C 4 )alkyl group,

with the proviso that

R′ and R are not simultaneously a hydrogen atom,

when R′ is a hydrogen atom, R is not a —NO 2 group or a —NH 2 group,

when n is 2 and R′ is a hydrogen atom, R is not a COOC 2 H 5 group or a chlorine atom,

wherein:

R independently represents a hydrogen atom, a halogen atom or a group chosen among a —CN group, a hydroxyl group, a —COOR 1 group, a (C 1 -C 3 )fluoroalkyl group, a (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, a —NR 1 R 2 group, a (C 1 -C 4 )alkoxy group, a phenoxy group and a (C 1 -C 3 )alkyl group, said alkyl group being optionally mono-substituted by a hydroxyl group,

R 1 and R 2 are independently a hydrogen atom or a (C 1 -C 3 )alkyl group,

n is 1, 2 or 3,

n′ is 1 or 2,

R′ is a hydrogen atom, a halogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a hydroxyl group, a —COOR 1 group, a —NO 2 group, a —NR 1 R 2 group, a morpholinyl or a morpholino group, a N-methylpiperazinyl group, a (C 1 -C 3 )fluoroalkyl group, a (C 1 -C 4 )alkoxy group and a —CN group,

R″ is a hydrogen atom or a (C 1 -C 4 )alkyl group,

with the exclusion of the following compound

and with the exclusion of compounds wherein R is a —NO 2 group or a —NH 2 group when R′ is a hydrogen or a methyl group, and

(3) a pharmaceutically acceptable salt thereof.

17 . A compound selected from the group consisting of:

(1) (8-Chloro-quinolin-2-yl)-pyridin-2-yl-amine

(2) 2-(Quinolin-2-ylamino)-isonicotinic acid

(5) 2-(8-Chloro-quinolin-2-ylamino)-isonicotinic acid

(6) (8-Chloro-quinolin-2-yl)-(4-methyl-pyridin-2-yl)-amine

(7) 6-(Quinolin-2-ylamino)-nicotinonitrile

(18) 8-chloro-N-(6-methylpyridin-2-yl)quinolin-2-amine

(46) 3-methyl-N-(6-methylpyridin-2-yl)quinolin-2-amine

(47) 5-cyano-2-(quinolin-2-ylamino)pyridin-1-ium chloride

(48) 2-((8-chloroquinolin-2-yl)amino)-4-methylpyridin-1-ium chloride

(49) 8-chloro-N-(4-ethylpyridin-2-yl)quinolin-2-amine

(50) 8-chloro-N-(6-ethylpyridin-2-yl)quinolin-2-amine

(51) 8-chloro-N-(4,6-dimethylpyridin-2-yl)quinolin-2-amine

(52) 6-((8-chloroquinolin-2-yl)amino)-2-methylnicotinonitrile

(53) 8-chloro-N-(4-chloropyridin-2-yl)quinolin-2-amine

(54) 8-methyl-N-(4-methylpyridin-2-yl)quinolin-2-amine

(55) N-(5-bromo-4-methylpyridin-2-yl)-8-chloroquinolin-2-amine

(56) 8-chloro-N-(3-ethyl-6-methylpyridin-2-yl)quinolin-2-amine

(57) 8-fluoro-N-(4-methylpyridin-2-yl)quinolin-2-amine

(58) 8-bromo-N-(4-methylpyridin-2-yl)quinolin-2-amine

(59) methyl 6-(quinolin-2-ylamino)nicotinate

(60) methyl 6-[(8-chloroquinolin-2-yl)amino]pyridine-3-carboxylate

(61) methyl 6-[(3-methylquinolin-2-yl)amino]pyridine-3-carboxylate

(62) methyl 2-[(8-chloroquinolin-2-yl)amino]pyridine-3-carboxylate

(63) 8-methoxy-N-(4-methylpyridin-2-yl)quinolin-2-amine

(64) N-(4-methylpyridin-2-yl)-5-nitroquinolin-2-amine

(65) 2-N-(4-methylpyridin-2-yl) quinoline-2,8-diamine

(66) 2-N-(4-methylpyridin-2-yl)quinoline-2,5-diamine

(67) methyl 6-[(4-methylquinolin-2-yl)amino]pyridine-3-carboxylate

(68) 8-chloro-N-[4-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine

(69) 2-[(8-chloroquinolin-2-yl)amino]pyridin-3-β1

(70) 8-chloro-N-[6-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine

(71) 6-chloro-N-(5-fluoropyridin-2-yl)quinolin-2-amine

(72) N-(6-ethylpyridin-2-yl)-3-methylquinolin-2-amine

(73) N-(5-fluoropyridin-2-yl)-3-methylquinolin-2-amine

(74) 3-methyl-N-[5-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine

(150) N-(4-methylpyridin-2-yl)-8-nitroquinolin-2-amine

(151) 6-chloro-N-(6-ethylpyridin-2-yl)quinolin-2-amine

(152) 6-chloro-N-(5-methylpyridin-2-yl)quinolin-2-amine

(153) 6-chloro-N-[5-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine and

(154) N2-(8-chloroquinolin-2-yl)-4-methylpyridine-2,3-diamine

and a pharmaceutically acceptable salt, wherein the pharmaceutically acceptable salt is selected from hydrobromide, tartrate, citrate, trifluoroacetate, ascorbate, hydrochloride, tartrate, triflate, maleate, mesylate, formate, acetate and fumarate.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 5, 2012
From: ROUX, PIERRE; MAHUTEAU, FLORENCE; NAJMAN, ROMAIN; TAZI, JAMAL; GADEA, GILLES; SCHERRER, DIDIER; BROCK, CARSTEN; CAHUZAC, NATHALIE
To: SOCIETE SPLICOS CAMPUS DU CNRS; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; INSTITUT CURIE; UNIVERSITE MONTPELLIER 2
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