IP Library › Patent Application 13377753
Patent Application
App. No. 13/377,753

COMPOUNDS USEFUL FOR TREATING PREMATURE AGING AND IN PARTICULAR PROGERIA

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Patent No.
US None
App. No.
13/377,753
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 —NO2 group, a —NRiR2 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 (Ci-C3)alkyl group, a hydroxyl group, a —COOR 1 group, a —NO2 group, a —NR 1 R 2 group, a morpholinyl or a morpholino group, a N-methylpiperazinyl group, a (Ci-C3)fluoroalkyl group, a (C 1 -C 4 )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 pathological or nonpathological conditions linked with premature aging. Some of said compounds are new and also form part of the invention.

Claims (572)

1 . A method of preventing, inhibiting, or treating a pathological or nonpathological condition linked with premature aging, comprising administering to an individual 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 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 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 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 is 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 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 the bond linked to NR″, Y is N, X is N, T is C, U is C and W is C, or

Z is N, V is C, Y is C, X is C, T is N, is C 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 1 -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, a (C 1 -C 3 )fluoroalkyl group, a —NO 2 group and a (C 1 -C 3 )alkoxy 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 independently represents a hydrogen atom, a halogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a (C 1 -C 3 )fluoroalkoxy group and a phenoxy group,

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

R′ is a hydrogen atom,

wherein:

R independently represents a hydrogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a —NO 2 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 or a halogen atom,

wherein:

R independently represents a hydrogen atom or 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,

wherein:

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

R′ is a hydrogen atom,

or (9) a pharmaceutically acceptable salt thereof.

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

(1) the compound of formula (Ia)

wherein:

n′ is 1,

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 (C 1 -C 3 )fluoroalkoxy 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 —COOR 1 group, and a —CN group,

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

with the proviso that

R and R′ are not simultaneously a hydrogen atom,

when n is 1, R is not a methyl group in the ortho or para position with respect to Z,

Z being N,

when R′ is a hydrogen atom, R is not a bromine atom or a chlorine atom,

when R is a hydrogen atom, R′ is not a methyl or ethyl group, a —COON group, a COOC 2 H 5 group or a bromine atom, said bromine atom being in an ortho position with respect to the bond linked to NR″;

(2) the compound of formula (Ic)

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

n is or 1 or 2,

n′ is 1 or 2,

R′ is a hydrogen atom or a group chosen among 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,

R is not a bromine atom when R′ is a hydrogen atom;

(3) the compound of formula (Id)

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 (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group and 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 group chosen among 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 when R′ is a hydrogen atom, R is different from a —NO 2 group, a —NH 2 group or a —COOH group;

(4) A compound of formula (Ii′)

wherein:

R 3 is a (C 1 -C 3 )fluoroalkyl group 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, a hydroxyl group, a —COOR 1 group, a —NO 2 group, a —NR 1 R 2 group, a (C 1 -C 3 )alkoxy group and a —CN group,

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

with the proviso that

when R′ is a hydrogen atom, R 3 is not a methyl group or a trifluoromethyl group or (5) a pharmaceutically acceptable salt thereof.

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

(1) a compound of formula (Ik)

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 (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, a —NR 1 R 2 group and a (C 1 -C 3 )alkoxy,

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 (C 1 -C 3 )alkoxy group and a —CN group;

(2) a compound of formula (Io)

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 (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, a NR 1 R 2 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,

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 (C 1 -C 3 )alkoxy group and a —CN group,

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

with the proviso that

when R is a hydrogen atom and n′ is 1, R′ is not a hydroxyl group;

(3) a compound of formula (Ij′)

wherein:

R 4 is a (C 1 -C 3 )fluoroalkyl group 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, a hydroxyl group, a —COOR 1 group, a —NO 2 group, a —NR 1 R 2 group, a (C 1 -C 3 )alkoxy group and a —CN group,

with the proviso that

when R′ is a hydrogen atom, R 4 is not a methyl group;

(4) a compound of formula (Ij″)

wherein:

R 4 is a (C 1 -C 3 )fluoroalkyl group or a (C 1 -C 3 )alkyl group,

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

(5) a compound of formula (Ij′″)

wherein:

R 4 is a (C 1 -C 3 )fluoroalkyl group 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, a hydroxyl group, a —NO 2 group, a —NR 1 R 2 group, a (C 1 -C 3 )alkoxy group and a —CN group,

with the proviso that

when R′ is a chlorine atom or a hydrogen atom, R 4 is not an ethyl group or a methyl group,

when R′ is a methyl group or a tertio-butyl group, R 4 is not a methyl group,

or (6) a pharmaceutically acceptable salt thereof.

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

(1) a compound of formula (Ip)

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 (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, a —NR 1 R 2 group and a (C 1 -C 3 )alkoxy group,

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 (C 1 -C 3 )alkoxy group and a —CN group,

with the proviso that

R and R′ are not simultaneously a hydrogen atom,

when n and n′ are 2 then R and R′ are not simultaneously a methyl group. group;

(2) a compound of formula (Ir)

wherein:

R independently represent 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 (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, a —NR 1 R 2 group and a (C 1 -C 3 )alkoxy group,

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 (C 1 -C 3 )alkoxy group and a —CN group,

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

or (3) a pharmaceutically acceptable salt thereof.

9 . A method of preventing, inhibiting, or treating a pathological or nonpathological condition linked with premature aging comprising administering to an individual at least one compound chosen selected from the group consisting of

(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.

10 . The method of claim 9 , wherein the compound is selected from the group consisting of 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), (168), and pharmaceutically acceptable hydrochloride, hydrobromide, tartrate, fumarate, citrate, trifluoroacetate, ascorbate, triflate, mesylate, tosylate, formate, acetate and malate salts thereof.

11 . The method of claim 1 , wherein the compound is administered in a pharmaceutical composition.

12 . The method of claim 10 , wherein the compound is administered in a pharmaceutical composition.

13 . The method of claim 1 , comprising administering the compound to a patient having a condition linked with premature aging.

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

15 . The method of claim 9 , comprising administering the compound to a patient having a condition linked with premature aging.

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

17 . A compound selected from the group consisting of:

(1) a compound of formula (Ia)

wherein:

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

n is 1, 2, or 3,

n′ is 1,

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 (C 1 -C 3 )fluoroalkoxy 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 —COOR 1 group, and a —CN group,

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

with the proviso that

R and R′ are not simultaneously a hydrogen atom,

when n is 1, R is not a methyl group in an ortho or para position with respect to Z, Z being N,

when R′ is a hydrogen atom, R is not a bromine atom or a chlorine atom,

when R is a hydrogen atom, R′ is not a methyl or ethyl group, a —COOH group, a COOC 2 H 5 group or a bromine atom, said bromine atom being in an ortho position with respect to the bond linked to NR″;

(2) a compound of formula (Ic)

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 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 or a group chosen among 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,

R is not a bromine atom when R′ is a hydrogen atom;

(3) a compound of formula (Id)

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 (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group and 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,

R′ is a hydrogen atom or a group chosen among 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 when R′ is a hydrogen atom, R is different from a —NO 2 group, a —NH 2 group or a —COOH group;

(4) a compound of formula (Ii′)

wherein:

R 3 is a (C 1 -C 3 )fluoroalkyl group 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, a hydroxyl group, a —COOR 1 group, a—NO 2 group, a —NR 1 R 2 group, a (C 1 -C 3 )alkoxy group and a —CN group,

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

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

n′ is 1 or 2

with the proviso that

when R′ is a hydrogen atom, R 3 is not a methyl group or a trifluoromethyl group

(5) a compound of formula (Ik)

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 (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, a —NR 1 R 2 group and a (C 1 -C 3 )alkoxy,

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 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 (C 1 -C 3 )alkoxy group and a —CN group;

(6) a compound of formula (Io)

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 (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, a —NR 1 R 2 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,

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 (C 1 -C 3 )alkoxy group and a —CN group,

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

with the proviso that

when R is a hydrogen atom and n′ is 1, R′ is not a hydroxyl group;

(7) a compound of formula (Ij′)

wherein:

R 4 is a (C 1 -C 3 )fluoroalkyl group 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, a hydroxyl group, a —COOR 1 group, a —NO 2 group, a —NR 1 R 2 group, a (C 1 -C 3 )alkoxy group and a —CN group,

R 1 and R 2 are independently a hydrogen atom or a (C 1 -C 3 )alkyl group, R″ is a hydrogen atom or a (C 1 -C 4 )alkyl group,

n′ is 1 or 2,

with the proviso that

when R′ is a hydrogen atom, R 4 is not a methyl group;

(8) a compound of formula (Ij″)

wherein:

R 4 is a (C 1 -C 3 )fluoroalkyl group 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, a hydroxyl group, a —COOR 1 group, a —NO 2 group, a —NR 1 R 2 group, a (C 1 -C 3 )alkoxy group and a —CN group,

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

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

n′ is or 2;

(9) a compound of formula (Ij′″)

wherein:

R 4 is a (C 1 -C 3 )fluoroalkyl group 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, a hydroxyl group, a —NO 2 group, a —NR 1 R 2 group, a (C 1 -C 3 )alkoxy group and a —CN group,

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

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

n′ is 1 or 2,

with the proviso that

when R′ is a chlorine atom or a hydrogen atom, R 4 is not an ethyl group or a methyl group,

when R′ is a methyl group or a tertio-butyl group, R 4 is not a methyl group,

(10) a compound of formula (Ip)

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 (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, a —NR 1 R 2 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,

R″ is a hydrogen atom or a (C 1 -C 4 )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 (C 1 -C 3 )alkoxy group and a —CN group,

with the proviso that

R and R′ are not simultaneously a hydrogen atom,

when n and n′ are 2 then R and R′ are not simultaneously a methyl group,

(11) a compound of formula (Ir)

wherein:

R independently represent 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 (C 1 -C 3 )fluoroalkoxy group, a —NO 2 group, a —NR 1 R 2 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,

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 (C 1 -C 3 )alkoxy group and a —CN group,

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

and (12) a pharmaceutically acceptable salt thereof.

18 . A compound 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

(18) 8-chloro-N-(6-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

(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

(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

(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) 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 and

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

and pharmaceutically acceptable salts thereof, wherein the pharmaceutically acceptable salts are selected from hydrochloride, hydrobromide, tartrate, fumarate, citrate, trifluoroacetate, ascorbate, triflate, mesylate, tosylate, formate, acetate and malate salts.

Assignments (3)
MERGER AND CHANGE OF NAME Recorded Dec 1, 2015
From: UNIVERSITE DE MONTPELLIER 2; UNIVERSITE MONTPELLIER 2
To: UNIVERSITE DE MONTPELLIER
Reel/Frame 037179/0237 →
MERGER Recorded Jan 20, 2015
From: SPLICOS
To: ABIVAX
Reel/Frame 034759/0705 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 4, 2012
From: TAZI, JAMAL; MAHUTEAU, FLORENCE; NAJMAN, ROMAIN; SCHERRER, DIDIER; SANTO, JULIEN
To: SOCIETE SPLICOS; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; INSTITUT CURIE; UNIVERSITE MONTPELLIER 2
Reel/Frame 028345/0102 →