Aralkyl-tetrahydro-pyridines, their preparation and pharmaceutical compositions containing same

1. A compound of formula (I):

in which

X represents N or CH;

R 1 represents a hydrogen or halogen atom or a CF 3 group;

n is an integer from 1 to 5; and

A represents a group of formula (a) to (d):

 in which m is 1 or 2; or

a salt, solvate or N-oxide thereof.

2. The compound according to claim 1 , where n is 1.

3. The compound according to claim 1 , where R 1 is a CF 3 group.

4. The compound according to claim 1 , where X is CH and R 1 is at the 3-position of the benzene.

5. The compound according to claim 1 , where X is N and the pyridine is substituted at the 2,6-positions.

6. The compound according to claim 1 , selected from the group consisting of:

1-[2-(2,3-dihydro-1H-cyclopenta[b]naphthalen-6-yl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine;

1-[2-(2,3-dihydro-1H-inden-5-yl)ethyl]-4-[3-trifluoromethylphenyl]-1,2,3,6-tetrahydropyridine;

1-[2-(5,6,7,8-tetrahydronaphthalen-2-yl)ethyl]-4-[3-trifluoromethylphenyl]-1,2,3,6-tetrahydropyridine;

1-[2-(2,3-dihydro-1H-cyclopenta[b]naphthalen-6-yl)ethyl]-4-(6-chloropyrid-2-yl)-1,2,3,6-tetrahydropyridine;

1-[2-(2,3-dihydro-1H-cyclopenta[b]naphthalen-6-yl)ethyl]-4-(6-trifluoromethylpyrid-2-yl)-1,2,3,6-tetrahydropyridine;

1-[3-(2,3-dihydro-1H-inden-5-yl)propyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine;

1-[4-(2,3-dihydro-1H-inden-5-yl)butyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine;

1-[2-(fluoren-2-yl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine;

1-[2-(9,10-dihydrophenanthren-2-yl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine;

1-[2-(2,3-dihydro-1H-cyclopenta[b]naphthalen-6-yl)ethyl]-(4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine;

1-[2-(fluoren-3-yl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine;

1-[2-(2,3-dihydro-1H-cyclopenta[a]naphthalen-8-yl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine;

1-[2-(5,6,7,8-tetrahydrophenanthren-3-yl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine; and

1-[2-(5,6,7,8-tetrahydroanthracen-2-yl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine;

or a salt, solvate or N-oxide thereof.

7. A method for preparing a compound according to claim 1 comprising:

(a) the reacting a compound of formula (II):

 with an acid compound of formula (III) or one of its functional derivatives

 to form a compound of formula IV

(b) reducing the carbonyl group of the compound of formula (IV), to form a compound of formula V;

(c) dehydrating the compound of formula (V)

wherein R 1 , X, n and A in the above formulae are as defined in claim 1 .

8. The compound according to claim 2 wherein R 1 is CF 3 .

9. The compound according to claim 2 wherein X is CH and R 1 is at the 3-position of the benzene.

10. The compound according to claim 3 wherein X is CH and R 1 is at the 3-position of the benzene.

11. The compound according to claim 8 wherein X is CH and R 1 is at the 3-position of the benzene.

12. The compound according to claim 2 wherein X is N and the pyridine is substituted at the 2,6-positions.

13. A compound according to claim 3 wherein X is N and the pyridine is substituted at the 2,6-positions.

14. A pharmaceutical composition comprising a pharmaceutically acceptable amount of the compound according to claim 1 and a pharmaceutically acceptable vehicle.

15. A pharmaceutical composition comprising a pharmaceutically acceptable amount of the compound according to claim 6 and a pharmaceutically acceptable vehicle.

16. A pharmaceutical composition comprising a pharmaceutically acceptable amount of the compound according to claim 11 and a pharmaceutically acceptable vehicie.

17. A pharmaceutical composition according to claim 14 containing from 0.001 to 100 mg of active ingredient.

18. A method for producing analgesia in a patient in need thereof comprising administering to said patient an analgesically effective amount of a compound according to claim 1 .

19. A method for producing analgesia in a patient in need thereof comprising administering to said patient an analgesically effective amount of a compound according to claim 6 .

20. A method for producing analgesia in a patient in need thereof comprising administering to said patient an analgesically effective amount of a compound according to claim 11 .