Compounds useful for treating AIDS

Patent metadata

Field	Value
Publication number	US-10017498-B2
Application number	US-201514789250-A
Country	US
Kind code	B2
Filing date	Jul 1, 2015
Priority date	Jun 12, 2009
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

A compound having the following formula or a pharmaceutically acceptable salt thereof:

where:
R independently represents a hydrogen atom, a halogen atom, 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, or 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, a (C 1 -C 3 )alkyl group, or a (C 1 -C 4 )alkoxy group, R″ is a hydrogen atom or a (C 1 -C 4 )alkyl group, n is 1, 2, or 3, and n′ is 1 or 2.

First claim

The invention claimed is:

1. A compound having the following formula or a pharmaceutically acceptable salt thereof:

where:
R′ is a hydrogen atom, a halogen atom, a (C 1 -C 3 )alkyl group, or a (C 1 -C 4 )alkoxy group,
R″ is a hydrogen atom or a (C 1 -C 4 )alkyl group,
n is 1 or 2, and
n′ is 1 or 2;
when n is 1, then R is a (C 1 -C 3 ) fluoroalkoxy group, a NR 1 R 2 group or a phenoxy group, where
R 1 and R 2 are independently a (C 1 -C 3 )group; and
when n is 2, then one of the two R is a (C 1 -C 3 ) fluoroalkoxy group and the other R is a (C 1 -C 3 )alkyl group.

2. A compound having the following formula or a pharmaceutically acceptable salt thereof:

where:
R independently represents a hydrogen atom, a halogen atom, 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, or 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, a (C 1 -C 3 )alkyl group, or a (C 1 -C 4 )alkoxy group, with the proviso that R′ is different from a methyl group at position 4 of the quinoline group,
R″ is a hydrogen atom or a (C 1 -C 4 )alkyl group,
n is 1, 2, or 3, and
n′ is 1 or 2.

3. A compound having the following formula or a pharmaceutically acceptable salt thereof:

where:
R independently represents a hydrogen atom, a halogen atom, 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, or 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 or a (C 1 -C 4 )alkyl group,
n is 1, 2, or 3, and
n′ is 1 or 2,
with the proviso that when n is 1, R is not a hydrogen atom, a methyl group in para of the bond linked to NR″, an ethoxy group in para of the bond linked to NR″, nor a fluorine atom in para of the bond linked to NR″.

4. A compound selected from the group consisting of:
(8) Quinolin-2-yl-(4-trifluoromethoxy-phenyl)-amine,
(75) 4-N-(8-chloroquinolin-2-yl)-1-N,1-N-dimethylbenzene-1,4-diamine,
(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,
(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) N-(4-(trifluoromethoxy)phenyl)quinolin-2-amine
(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-N-(4-(trifluoromethoxy)phenyl)quinolin-2-amine
(96) 6-chloro-N-(4-(trifluoromethoxy)phenyl)quinolin-2-amine,
(97) 4-methyl-N-(4-(trifluoromethoxy)phenyl)quinolin-2-amine
(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,
(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, and
their pharmaceutically acceptable salts.

5. The compound of claim 4 , wherein the pharmaceutically acceptable salts are selected from hydrobromide, tartrate, citrate, trifluoroacetate, ascorbate, hydrochloride, triflate, maleate, mesylate, formate, acetate, and fumarate.

6. A pharmaceutical composition comprising at least one compound as defined in claim 1 .

7. A pharmaceutical composition comprising at least one compound as defined in claim 2 .

8. A pharmaceutical composition comprising at least one compound as defined in claim 3 .

9. A pharmaceutical composition comprising at least one compound as defined in claim 4 .

10. A pharmaceutical composition comprising at least one compound as defined in claim 5 .

11. The pharmaceutical composition according to claim 6 , further comprising a pharmaceutically acceptable support.

12. The pharmaceutical composition according to claim 7 , further comprising a pharmaceutically acceptable support.

13. The pharmaceutical composition according to claim 8 , further comprising a pharmaceutically acceptable support.

14. The pharmaceutical composition according to claim 9 , further comprising a pharmaceutically acceptable support.

15. The pharmaceutical composition according to claim 10 , further comprising a pharmaceutically acceptable support.

16. A compound having the following formula or a pharmaceutically acceptable salt thereof:

where:
R independently represents a (C 1 -C 3 )fluoroalkoxy group,
R′ is a hydrogen atom, a halogen atom, a (C 1 -C 3 )alkyl group or a (C 1 -C 4 )alkoxy group,
R″ is a hydrogen atom or a (C 1 -C 4 )alkyl group,
n is 1, and
n′ is 1 or 2.

17. A pharmaceutical composition comprising at least one compound as defined in claim 16 .

18. The pharmaceutical composition according to claim 16 , further comprising a pharmaceutically acceptable support.

Assignees

• Abivax
• Centre Nationale De Recherche Scient
• Inst Curie
• Univ Montpellier 2
• Centre Nat Rech Scient
• Univ Montpellier

Inventors

• Tazi Jamal
• Mahuteau Florence
• Najman Romain
• Scherrer Didier
• Campos Noelie
• Garcel Aude

Classifications

• A61P35/00

  Antineoplastic agents · CPC title

• C07D213/74

  Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals · CPC title

• C07D401/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D403/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D215/38 Primary

  Nitrogen atoms (nitro radicals C07D215/18) · CPC title