IP Library › Granted Patent US 9,637,475
Granted Patent B2
US 9,637,475 · App. 14/789,149 · Granted May 2, 2017

Compounds for treating cancer

Inventors: Pierre Roux (Saint-Gely-du-Fesc, FR); Florence Mahuteau (Saint Remy les Chevreuse, FR); Romain Najman (L'Hay-les-Roses, FR); Jamal Tazi (Clapiers, FR); Gilles Gadea (Matelles, FR); Didier Scherrer (Castelnau le Lez, FR); Carsten Brock (Montpellier, FR); Nathalie Cahuzac (Jacou, FR)
Assignees: ABIVAX; CENTRE NATIONALE DE RECHERCHE SCIENTIFIQUE; INSTITUT CURIE; UNIVERSITE DE MONTPELLIER
C07D403/12A61K31/4709A61K31/4985C07D213/74C07D215/38C07D215/42C07D215/46C07D241/44C07D401/12
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Quick Facts
Patent No.
US 9,637,475
App. No.
14/789,149
Granted
May 2, 2017
Kind
B2
Abstract

A method of preventing, inhibiting, or treating cancer that includes contacting a cell with at least one compound of formula (Ia) or a pharmaceutically acceptable salt thereof: 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.

Claims (57)

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

wherein:

R independently represent a hydrogen atom, a halogen atom, 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, or a (C 1 -C 3 )alkyl group 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, 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 group, a morpholino group, a N-methylpiperazinyl group, a (C 1 -C 3 )fluoroalkyl group, a (C 1 -C 4 )alkoxy group, or a —CN group, and

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, and

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

2. The compound of claim 1 , wherein R is a (C 1 -C 3 )fluoroalkoxy group.

3. The compound of claim 1 , wherein R′ is a —NR 1 R 2 group.

4. The compound of claim 1 , wherein R′ is a morpholinyl, a morpholino group, or a N-methylpiperazinyl group.

5. A compound selected from the group consisting of:

(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;

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

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

their pharmaceutically acceptable salts.

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

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

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

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

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

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

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

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

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

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

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

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

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

19. A method of treating cancer selected from the group consisting of breast cancer, pancreatic cancer, prostate cancer, lung cancer, non-small cell lung cancer, thyroid cancer, liver cancer, and kidney cancer, comprising:

contacting a cell with at least one compound of formula (Iq) or a pharmaceutically acceptable salt thereof:

wherein:

R independently represent a hydrogen atom, a halogen atom, 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, or a (C 1 -C 3 )alkyl group 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, 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 group, a morpholino group, a N-methylpiperazinyl group, a (C 1 -C 3 )fluoroalkyl group, a (C 1 -C 4 )alkoxy group, or a —CN group, and

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

20. The method of claim 19 , wherein:

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

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

21. The method of claim 19 , wherein R is a (C 1 -C 3 )fluoroalkoxy group.

22. A method of treating cancer selected from the group consisting of breast cancer, pancreatic cancer, prostate cancer, lung cancer, non-small cell lung cancer, thyroid cancer, liver cancer, and kidney cancer comprising contacting a cell with at least one compound selected from the group consisting of:

(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;

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

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

pharmaceutically acceptable salts thereof.

23. The method of claim 22 , wherein the pharmaceutically acceptable salts are selected from hydrobromide, citrate, trifluoroacetate, ascorbate, hydrochloride, tartrate, triflate, maleate, mesylate, formate, acetate, or fumarate.

24. The method of claim 19 , further comprising a step of administering the compound to a patient in need of cancer treatment.

25. The method of claim 24 , wherein the compound is administered to the patient orally.

26. The method of claim 22 , further comprising a step of administering the compound to a patient in need of cancer treatment.

27. The method of claim 26 , wherein the compound is administered to the patient orally.

Assignments (1)
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 →
Priority Claims (2)
EP 09162630 · Jun 12, 2009 · regional
EP 09305540 · Jun 12, 2009 · regional
Continuity (5)
Continuation 14087762 · Nov 22, 2013
Continuation 13377745
Provisional Application 61186552 · Jun 12, 2009
Provisional Application 61186544 · Jun 12, 2009
Related Publication 20150299129A1 · Oct 22, 2015