Compounds for preventing, inhibiting, or treating cancer, aids and/or premature aging
The manufacture and use of compounds of formula (Ia) or a pharmaceutically acceptable salt thereof for preventing, inhibiting or treating cancer, AIDS and/or premature aging. The compounds of formula (Ia) being: where: R independently represents a hydrogen atom, a halogen atom, 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, or a (C 1 -C 3 )alkoxy group; R′ is a hydrogen atom, a halogen atom, a (C 1 -C 3 )alkyl group, a —NO 2 group, a (C 1 -C 3 )alkoxy group, or a —NR 1 R 2 group; and R 1 and R 2 are a hydrogen atom or a (C 1 -C 3 ) alkyl group.
1. A compound, or a pharmaceutically acceptable salt thereof, selected from the group consisting of:
a compound of formula (Ic):
wherein:
R independently represents a hydrogen atom, a halogen atom, 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, or 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,
n is 1 or 2,
n′ is 1 or 2,
R″ is a hydrogen atom or a (C 1 -C 4 )alkyl group,
R′ is a hydrogen atom, a (C 1 -C 3 )alkyl group, a —NO 2 group, a —NR 1 R 2 group and a (C 1 -C 3 )alkoxy group,
with the proviso that:
R and R′ are not simultaneously a hydrogen atom, and
R is not a bromine atom when R′ is a hydrogen atom;
a compound of formula (Id):
wherein:
R independently represents a hydrogen atom, a halogen atom, 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 (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, or a —NR 1 R 2 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 or a (C 1 -C 4 )alkyl group, and
R′ is a hydrogen atom, a (C 1 -C 3 )alkyl group, a —NO 2 group, a —NR 1 R 2 group, or a (C 1 -C 3 )alkoxy group,
with the proviso that when R′ is a hydrogen atom, R is different from a —NO 2 group, a —NH 2 group, or a —COOH group;
a compound of formula (Io):
wherein:
R independently represents
a hydrogen atom,
a halogen atom,
a (C 1 -C 3 )alkyl group where the (C 1 -C 3 )alkyl group is optionally mono-substituted by a hydroxyl group,
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, or
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,
n is 1, 2 or 3,
n′ is 1 or 2,
R′ is a hydrogen atom, a halogen atom, a (C 1 -C 3 )alkyl group, a (C 1 -C 3 )fluoroalkyl group, a —COOR 1 group, a —NR 1 R 2 group, a (C 1 -C 3 )alkoxy group, or a —CN group, and
R″ is a hydrogen atom or a (C 1 -C 4 )alkyl group;
and
a compound of formula (Ir):
wherein:
R independently represent a hydrogen atom, a halogen atom, 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 (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, a —NR 1 R 2 group, or 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,
n is for 2,
n′ is 1 or 2,
R′ is a hydrogen atom, a halogen atom, a (C 1 -C 3 )alkyl group, a —COOR 1 group, a —NO 2 group, a —NR 1 R 2 group, a (C 1 -C 3 )alkoxy group, or a —CN group, and
R″ is a hydrogen atom or a (C 1 -C 4 )alkyl group.
2. The compound, or a pharmaceutically acceptable salt thereof, of claim 1 , wherein the compound is a compound of the formula (Ir):
3. The compound, or a pharmaceutically acceptable salt thereof, of claim 2 , wherein the compound is a compound of the formula (Ic):
4. The compound, or a pharmaceutically acceptable salt thereof, of claim 3 , wherein the compound is a compound of the formula (Id):
5. The compound, or a pharmaceutically acceptable salt thereof, of claim 4 , wherein the compound is a compound of the formula (Io):
6. The compound of claim 5 , wherein the pharmaceutically acceptable salt is selected from the group consisting of a hydrochloride salt, a hydrobromide salt, a tartrate salt, a fumarate salt, a citrate salt, a trifluoroacetate salt, an ascorbate salt, a triflate salt, a mesylate salt, a tosylate salt, a formate salt, an acetate salt, and a malate salt.
7. A compound, or a pharmaceutically acceptable salt thereof, selected from the group consisting of:
(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
(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
(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
(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
(159) N-(3-aminopyridin-2-yl)quinolin-3-amine
(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 and
(168) N-(4-methylpyridin-2-yl)-4-(morpholin-4-yl)quinolin-7-amine.
8. The compound of claim 7 , wherein the pharmaceutically acceptable salt is selected from the group consisting of a hydrochloride salt, a hydrobromide salt, a tartrate salt, a fumarate salt, a citrate salt, a trifluoroacetate salt, an ascorbate salt, a triflate salt, a mesylate salt, a tosylate salt, a formate salt, an acetate salt, and a malate salt.
9. A pharmaceutical composition comprising at least one compound, or a pharmaceutically acceptable salt thereof, of claim 6 and a pharmaceutically acceptable carrier.
10. A pharmaceutical composition comprising at least one compound, or a pharmaceutically acceptable salt thereof, of claim 7 and a pharmaceutically acceptable carrier.