Triazolopyridine carboxamide derivatives, preparation thereof and therapeutic use thereof

1. A compound of the formula (I):

in which:

X is hydrogen, halogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkyl, S(O) m R″, hydroxyl or cyano;

A is a bond, (C 1 -C 2 )alkylene or (C 2 )alkenyl group;

or A is absent and the attachment is a benzhydryl group;

R 1 and R 2 are, independently of one another, one or more groups selected from the group consisting of hydrogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 3 -C 7 )cycloalkyl, (C 3 -C 7 )cycloalkyl(C 1 -C 6 )alkyl, (C 3 -C 7 )cycloalkyl(C 1 -C 6 )alkoxy, halogen, cyano, C(O)R′, C(O)OR′, C(O)NR 10 R 20 , NO 2 , NR 10 R 20 and NR 10 C(O)—R 20 group, wherein (C 1 -C 6 )alkyl and (C 1 -C 6 )alkoxy are optionally substituted with one or more groups selected, independently of one another, from halogen, hydroxyl, amino and NR 10 R 20 ;

R′ is selected from hydrogen, (C 1 -C 6 )alkyl, (C 3 -C 7 )cycloalkyl and (C 3 -C 7 )cycloalkyl(C 1 -C 6 )alkyl;

R″ is selected from (C 1 -C 6 )alkyl, (C 3 -C 7 )cycloalkyl and (C 3 -C 7 )cycloalkyl(C 1 -C 6 )alkyl; and

R 10 and R 20 are, independently of one another, selected from hydrogen, (C 1 -C 6 )alkyl, (C 3 -C 7 )cycloalkyl and (C 3 -C 7 )cycloalkyl(C 1 -C 6 )alkyl; or

R 10 and R 20 form a saturated or partially unsaturated ring containing from 5 to 7 carbon atoms and optionally containing a heteroatom chosen from 0, N or S(O) m ; wherein

m represents 0, 1 or 2; or

a salt thereof.

2. The compound of formula (I) according to claim 1 , wherein:

X is hydrogen or halogen; and

A is a bond, or (C 1 -C 2 )alkylene; or

when A is absent the attachment is a benzhydryl group; or

a salt thereof.

3. The compound of formula (I) according to claim 1 , wherein:

X is hydrogen or halogen;

A is a bond or (C 1 -C 2 )alkylene; and

R 1 and R 2 are, independently of one another, one or more groups selected from hydrogen, halogen, cyano or alkoxy; or

a salt thereof.

4. The compound of formula (I) according to claim 1 , wherein:

X is hydrogen or halogen;

A is a bond or ethylene; and

R 1 and R 2 are, independently of one another, one or more groups selected from hydrogen or halogen; or

a salt thereof.

5. The compound of formula (I) according to claim 1 , wherein:

X is hydrogen or chlorine;

A is a bond or ethylene; and

R 1 and R 2 are, independently of one another, one or more groups selected from hydrogen, fluorine or chlorine; or

a salt thereof.

6. The compound of formula (I) according to claim 1 , which is selected from the group consisting of:

(4-benzhydrylpiperazin-1-yl)[1,2,3]triazolo[4,5-b]pyridin-1-ylmethanone;

(4-benzhydrylpiperazin-1-yl)(6-chloro[1,2,3]triazolo[4,5-b]pyridin-1-yl)methanone;

{4-[bis(4-fluorophenyl)methyl]piperazin-1-yl}[1,2,3]triazolo[4,5-b]pyridin-1-ylmethanone;

{4-[bis(4-chlorophenyl)methyl]piperazin-1-yl}[1,2,3]triazolo[4,5-b]pyridin-1-ylmethanone;

{4-[bis(4-fluorophenyl)methyl]piperazin-1-yl} (6-chloro[1,2,3]triazolo[4,5-b]pyridin-1-yl)methanone;

{4-[bis(4-chlorophenyl)methyl]piperazin-1-yl} (6-chloro[1,2,3]triazolo[4,5-b]pyridin-1-yl)methanone;

[4-(10,11-dihydro-5H-dibenzo[a,d] cyclohepten-5-yl)piperazin-1-yl][1,2,3]triazolo[4,5-b]pyridin-1-ylmethanone; and

[4-(9H-fluoren-9-yl)piperazin-1-yl][1,2,3]triazolo[4,5-b]pyridin-1-ylmethanone.

7. A process for preparing the compound of formula (I) according to claim 1 , comprising:

reacting a compound of formula (II):

in which X is as defined in claim 1 , with a compound of formula (III):

in which A, R 1 and R 2 are as defined in claim 1 .

8. A process for preparing a compound of formula (I) according to claim 1 , comprising:

reacting a compound of formula (IV):

in which X is as defined in claim 1 , with a compound of formula (V):

in which A, R 1 and R 2 are as defined in claim 1 and L represents a leaving group.

9. A compound of formula (IV):

in which

X is hydrogen, halogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkyl, S(O) m R″, hydroxyl or cyano.

10. A pharmaceutical composition comprising a compound of formula (I) according to claim 1 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.

11. A pharmaceutical composition comprising a compound of formula (I) according to claim 2 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.

12. A pharmaceutical composition comprising a compound of formula (I) according to claim 3 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.

13. A pharmaceutical composition comprising a compound of formula (I) according to claim 4 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.

14. A pharmaceutical composition comprising a compound of formula (I) according to claim 5 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.

15. A pharmaceutical composition comprising a compound of formula (I) according to claim 6 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.