Compounds useful for treating AIDS

1. A method of inhibiting replication of HIV-1 in a patient infected with HIV-1 comprising administering to a patient in need thereof an effective quantity of at least one compound of formula (I) or a pharmaceutically acceptable salt thereof to thereby inhibit replication of HIV-1:

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, 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, said alkyl group 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, 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, or 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,

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 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, or

Z is N, V is C, Y is N, X is N, T is C, U is C, and W is C.

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

(2)

wherein:

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, and

R′ is a hydrogen atom, a halogen atom, a (C 1 -C 3 )alkyl group, or a (C 1 -C 4 )alkoxy group,

(3)

wherein:

R independently represents a hydrogen atom, 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, or a (C 1 -C 3 )alkoxy group,

R′ is a hydrogen atom, and

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

(5)

wherein:

R is a hydrogen atom, and

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

(13)

wherein:

R independently represents a hydrogen atom, a halogen atom, a —NO 2 group, a —CN group, or a (C 1 -C 3 )alkyl group, said alkyl being optionally mono-substituted by a hydroxyl group, and

R′ is a hydrogen atom, a halogen atom, or a (C 1 -C 3 )fluoroalkyl group, and

(18) pharmaceutically acceptable salts thereof.

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

(2)

wherein:

R independently represents a hydrogen atom, a halogen atom, a (C 1 -C 4 )alkyl group, a —NR 1 R 2 group, a (C 1 -C 3 )alkoxy group, or a (C 1 -C 3 )fluoroalkoxy group,

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

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

(3)

wherein:

R independently represents a hydrogen atom, a (C 1 -C 3 )fluoroalkyl group, a —NO 2 group, or a (C 1 -C 3 )alkoxy group, and

R′ is a hydrogen atom,

(4)

wherein:

R is a hydrogen atom, and

R′ is a hydrogen atom or a halogen atom,

(5)

wherein:

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

n is 1, 2, or 3, and

R′ is a hydrogen atom or a (C 1 -C 3 )fluoroalkyl group, and

(6) pharmaceutically acceptable salts thereof.

4. The method of claim 2 , wherein formula (Ib) is

wherein:

n is 1, and

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

5. The method of claim 1 , wherein the compound of formula (I) is a compound of formula (Ie) or a pharmaceutically acceptable salt thereof:

with the proviso that when R is a hydrogen atom, R′ is not a bromine atom.

6. The method of claim 2 , wherein formula (Ic) is:

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, 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

R and R′ are not simultaneously a hydrogen atom, and

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

7. A method of inhibiting replication of HIV-1 in a patient infected with HIV-1 comprising administering to a patient in need thereof a quantity effective to inhibit replication of HIV-1 at least one compound selected from the group consisting of:

(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,

(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,

(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,

(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,

(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) 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

pharmaceutically acceptable salts thereof.

8. The method of claim 7 , wherein the compound is selected from the group consisting of the compounds (8), (10)-(14), (75), (77)-(84), (86)-(104), (105), (106), (109)-(117), (135)-(141), (155)-(157), (158), (159)-(165), and pharmaceutically acceptable hydrobromide, tartrate, citrate, trifluoroacetate, ascorbate, hydrochloride, tartrate, triflate, maleate, mesylate, formate, acetate, and fumarate salts thereof.

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

10. The method of claim 8 , wherein the compound is administered in a pharmaceutical composition.

11. The method of claim 1 , wherein the individual is a patient having HIV or AIDS.

12. The method of claim 11 , wherein the compound is orally administered to the patient.

13. The method of claim 7 , wherein the individual is a patient having HIV or AIDS.

14. The method of claim 13 , wherein the compound is orally administered to the patient.

15. A compound selected from the group consisting of:

(1)

wherein:

R independently represents 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, 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, 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, or a —CN group, and

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

with the proviso that when R is a hydrogen atom, R′ is not a bromine atom; and

(3) pharmaceutically acceptable salts thereof.

16. A compound selected from the group consisting of:

(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, and

pharmaceutically acceptable salts thereof, selected from hydrobromide, tartrate, citrate, trifluoroacetate, ascorbate, hydrochloride, tartrate, triflate, maleate, mesylate, formate, acetate, and fumarate salts.

17. A method of inhibiting replication of HIV-1 in a patient infected with HIV-1 comprising administering to a patient in need thereof an effective quantity of at least one compound of formula (Ij) or a pharmaceutically acceptable salt thereof to thereby inhibit replication of HIV-1:

wherein:

R independently represents a hydrogen atom, a (C 1 -C 3 )fluoroalkoxy group, or a (C 1 -C 3 )alkyl group;

R′ is a hydrogen atom;

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.

18. The method of claim 17 , wherein the compound is selected from the group consisting of:

(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, and

pharmaceutically acceptable salts thereof.