Derivatives of N-heterocyclylmethylbenzamides, preparation method thereof and application of same in therapeutics

1. A compound of the formula (I)

in which

R represents a hydrogen atom;

n represents 1;

X represents a group of formula CH;

R 1 represents either a phenyl or naphthyl group optionally substituted with one or more substituents chosen from halogen atoms, linear or branched (C 1 -C 6 )alkyl, hydroxyl and (C 1 -C 6 )alkoxy groups, the trifluoromethyl group, or a cyclohexyl group, or a heteroaryl group chosen from thienyl, pyridinyl, oxazolyl, furanyl, thiazolyl, quinolinyl, and isoquinolinyl groups;

R 2 represents either a hydrogen atom, or one or more substituents chosen from halogen atoms, trifluoromethyl, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, thienyl, phenyloxy, hydroxyl, mercapto, thio(C 1 -C 6 )alkyl and cyano group or a group of formula —NR 4 R 5 , SO 2 NR 4 R 5 , —SO 2 —(C 1 -C 6 )alkyl, —SO 2 -phenyl, —CONR 4 R 5 , —COOR 7 , —CO—(C 1 -C 6 )alkyl, —CO-phenyl, —NHCOR 8 , —NHSO 2 —(C 1 -C 6 )alkyl, —NHSO 2 -phenyl and —NHSO 2 NR 4 R 5 or a group of formula—OCF 2 O— attached at the 2- and 3-positions of the phenyl group;

the groups (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, —SO 2 —C 1 -C 6 )alkyl, —CO—(C 1 -C 6 )alkyl and —NHSO 2 —(C 1 -C 6 )alkyl being optionally substituted with one or more groups R 3 ;

the groups phenyl, —SO 2 -phenyl, —CO-phenyl and —NHSO 2 -phenyl being optionally substituted with a group R 6 ;

R 3 represents a halogen atom, or a phenyl, (C 1 -C 6 )alkoxy or —NR 4 R 5 group;

R 4 and R 5 represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group or R 4 and R 5 form with the nitrogen atom bearing them a pyrrolidine ring, a piperidine ring or a morpholine ring;

R 6 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, a cyano group, a hydroxyl group, a mercapto group, a (C 1 -C 6 )alkyl or (C 1 -C 6 )alkoxy group;

R 7 represents a hydrogen atom or a (C 1 -C 6 )alkyl group optionally substituted with one or more groups R 3 , or a phenyl group optionally substituted with a group R 6 ;

R 8 represents a (C 1 -C 6 )alkyl group optionally substituted with one or more groups R 3 , or a (C 1 -C 6 )alkoxy group, or a phenyl group optionally substituted with a group R 6 ; or

said compound in the form of a free base or an addition salt with an acid, or a stereoisomer.

2. The compound as claimed in claim 1 , which is in the threo configuration.

3. The compound as claimed in claim 1 , wherein R 1 represents an optionally substituted phenyl group.

4. The compound as claimed in claim 2 , wherein R 1 represents an optionally substituted phenyl group.

5. The compound as claimed in claim 1 , which is selected from the group consisting of:

threo-2-chloro-N-[(1-azabicyclo[2.2.2]oct-2-yl)phenylmethyl]-3-trifluoromethylbenzamide hydrochloride 1:1;

threo-2,6-dichloro-N-[(1-azabicyclo[2.2.2]oct-2-yl)phenylmethyl]-3-trifluoromethylbenzamide hydrochloride 1:1;

2,6-dichloro-N-[(1S)-[(2S)(1-azabicyclo[2.2.2]oct-2-yl)phenylmethyl]-3-(trifluoromethyl)benzamide hydrochloride 1:1;

threo-N-[1-Azabicyclo[2.2.2]oct-2-yl(4-fluorophenyl)methyl]-2,6-dichloro-3-(trifluoromethyl)benzamide hydrochloride 1:1; or

said compound in the form of a free base or an addition salt with an acid.

6. A compound which is 2-chloro-N-(8α,9S)cinchonan-9-yl)-3-trifluoromethyl-benzamide hydrochloride 2:1.