Use of quinoline derivatives for the treatment of inflammatory diseases
The present disclosure relates to the use of a compound of formula (I) or anyone of its pharmaceutically acceptable salts, in the treatment and/or prevention of an inflammatory disease; wherein: means an aromatic ring wherein V is C or N and when V is N; Q is N or O, provided that R″ does not exist when Q is O; R′ independently represent a hydrogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a halogen atom, 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 —O—P(═O)—(OR 3 )(OR 4 ) group, a (C 1 -C 4 )alkoxy group and a —CN group, and can further be a group chosen among:
1. A method of treating an inflammatory disease comprising administering a compound of formula (I) to a patient in need thereof:
wherein:
Z is C or N,
V is C or N,
means an aromatic ring wherein V is C or N and when V is N, V is in ortho, meta or para of Z, i.e. forms respectively a pyridine, 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 (C 1 -C 3 )fluoroalkyl group, a (C 1 -C 3 )fluoroalkoxy group, a (C 3 -C 6 )cycloalkyl group, a —NO 2 group, a —NR 1 R 2 group, a (C 1 -C 4 )alkoxy group, a phenoxy group, a —NR 1 —SO 2 —NR 1 R 2 group, a —NR 1 —SO 2 —R 1 group, a —NR 1 —C(═O)—R 1 group, a —NR 1 —C(═O)—NR 1 R 2 group, a —SO 2 —NR 1 R 2 group, a —SO 3 H group, a —O—SO 2 —OR 3 group, a —O—P(═O)—(OR 3 )(OR 4 ) group, a —O—CH 2 —COOR 3 group and a (C 1 -C 3 )alkyl group, said alkyl being optionally mono-substituted by a hydroxyl group,
Q is N or O, provided that R″ does not exist when Q is O,
R 1 and R 2 are independently a hydrogen atom or a (C 1 -C 3 )alkyl group,
R 3 and R 4 independently represent a hydrogen atom, Li + , Na + , K + , N + (Ra) 4 or a benzyl group,
n is 1, 2 or 3,
n′ is 1, 2 or 3,
R′ independently represent a hydrogen atom or a group chosen among a (C 1 -C 3 )alkyl group, a halogen atom, 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 —O—P(═O)—(OR 3 )(OR 4 ) group and a —CN group, and can further be a group chosen among:
A is a covalent bond, an oxygen atom or NH,
B is a covalent bond or NH,
m is 1, 2, 3, 4 or 5,
p is 1, 2 or 3,
Ra and Rb independently represent a hydrogen atom, a (C 1 -C 5 )alkyl group or a (C 3 -C 6 )cycloalkyl group,
Ra and Rb can further form together with the nitrogen atom to which they are attached a saturated 5- or 6-membered heterocycle optionally containing a further heteroatom chosen among N, O and S, said heterocycle being optionally substituted by one or more Ra, provided that when R′ is a group (IIa) or (IIIa), n′ may be 2 or 3 only if other R′ groups are different from said group (IIa) or (IIIa),
R″ is a hydrogen atom, a (C 1 -C 4 )alkyl group or is a group (IIa) as defined above,
or any one of its pharmaceutically acceptable salt; wherein
said inflammatory disease is selected from the group consisting of: psoriasis, dermatitis, eczema, bronchitis, and asthma.
2. The method according to claim 1 , wherein R″ is a hydrogen atom, a (C 1 -C 4 )alkyl group or a group
wherein m is 2 or 3 and X 1 is O, CH 2 or N—CH 3 .
3. The method according to claim 1 , wherein R independently represent a hydrogen atom, a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an amino group, a halogen atom and a —O—P(═O)—(OR 3 )(OR 4 ) group.
4. The method according to claim 1 , wherein R′ independently represent a hydrogen atom, a halogen atom, an amino group, a methyl group, a —O—P(═O)—(OR 3 )(OR 4 ) group or a group
wherein A is O or NH, m is 2 or 3 and X 1 is O, CH 2 or N—CH 3 , provided that when R′ is such a group, n′ is 1 or 2, and when n′ is 2, the other R′ group is different from said group or alternatively R′ independently represent a hydrogen atom, a halogen atom, a methyl group or a group
wherein A is O or NH, m is 2 and X 1 is O, CH 2 or N—CH 3 , provided that when R′ is such a group, n′ is 1 or 2, and when n′ is 2, the other R′ group is different from said group.
5. The method according to claim 1 , wherein Q is N.
6. The method according to claim 1 , wherein the compound of formula (I) is selected from
7. The method according to claim 1 , wherein the compound of formula (I) is selected from compounds of formula (Id) and (Ie):
wherein R, R′, n and n′ are as defined in claim 1 .
8. The method according to claim 1 , wherein said inflammatory disease is selected from the group consisting of: psoriasis, dermatitis, and eczema.
9. The method according to claim 1 , wherein said inflammatory disease is selected from the group consisting of: dermatitis and eczema.
10. The method according to claim 1 , wherein said inflammatory is eczema.
11. The method according to claim 1 , wherein said inflammatory is dermatitis.
12. The method according to claim 1 , wherein said inflammatory disease is selected from the group consisting of: bronchitis and asthma.
13. The method according to claim 1 , wherein said inflammatory disease is psoriasis.
14. The method according to claim 1 , wherein said inflammatory disease is bronchitis.
15. The method according to claim 1 , wherein said inflammatory disease is asthma.
16. The method according to claim 1 , wherein the compound of formula (I) is 8-chloro-N-[4-(trifluoromethoxy)phenyl]quinolin-2-amine.
17. The method according to claim 16 , wherein said inflammatory disease is selected from the group consisting of: psoriasis, eczema, bronchitis, and asthma.
18. The method according to claim 16 , wherein said inflammatory disease is psoriasis.
19. The method according to claim 16 , wherein said inflammatory disease is dermatitis.
20. The method according to claim 16 , wherein said inflammatory disease is eczema.
21. The method according to claim 16 , wherein said inflammatory disease is bronchitis.
22. The method according to claim 16 , wherein said inflammatory disease is asthma.