Imidazole derivatives and their use for modulating the GABA

1. A compound of the general formula (I):

any of its stereoisomers or any mixture of its stereoisomers,

or a pharmaceutically acceptable salt thereof,

wherein R 1 represents —COOR 3 ;

wherein R 3 represents hydrogen, alkyl, cycloalkyl, cycloalkylakyl, alkenyl, alkynyl, aryl or heteroaryl;

which aryl or heteroaryl group is optionally substituted with one or more substituents independently selected from the group consisting of:

halo, hydroxy, R a R b N—, R a R b N-alkyl, cyano, nitro, trifluoromethyl, trifluoromethoxy, alkoxy, cycloalkoxy, R a —(C═O)—, R a —O—(C═O)—, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, and alkynyl;

wherein R a and R b independent of each other are hydrogen or alkyl;

R 2 represents halo, nitro, R c — or R c —(CH 2 ) m —O—(CH 2 ) n —;

wherein m is 0 or 1; n is 0 or 1; and

R c is an aryl or heteroaryl group;

which aryl or heteroaryl group is optionally substituted with one or more substituents independently selected from the group consisting of:

halo, hydroxy, R d R e N—, R d R e N-alkyl, R d R e N—(C═O)—, cyano, nitro, trifluoromethyl, trifluoromethoxy, alkoxy, cycloalkoxy, R d —(C═O)—, R d —O—(C═O)—, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, and alkynyl;

wherein when both m and n are 0, R c is not phenyl or pyridinyl; and

wherein R d and R e independent of each other are hydrogen or alkyl

with the provisos that

when R 3 represents hydrogen, R 2 is not halo; and

when R 3 represents alkyl, R 2 is not nitro or halo.

2. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein

R 1 represents —COOR 3 ; wherein R 3 represents hydrogen or alkyl.

3. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein

R 1 represents —COOR 3 ; wherein R 3 represents heteroaryl.

4. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein

R 2 represents halo or nitro.

5. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein

R 2 represents R c — or R c —(CH 2 ) m —O—(CH 2 ) n —;

wherein m is 0 or 1; n is 0 or 1; and

R c is an aryl or heteroaryl group;

which aryl or heteroaryl group is optionally substituted with one or more substituents independently selected from the group consisting of:

halo, hydroxy, R d R e N—, R d R e N-alkyl, R d R e N—(C═O)—, cyano, nitro, trifluoromethyl, trifluoromethoxy, alkoxy, cycloalkoxy, R d —(C═O)—, R d —O—(C═O)—, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, and alkynyl;

wherein R d and R e independent of each other are hydrogen or alkyl.

6. A compound selected from the group consisting of:

1-[3-(Pyridin-2-ylmethoxymethyl)-phenyl]-1H-imidazole-4-carboxylic acid ethyl ester;

1-[3-(1-Methyl-1H-imidazol-2-ylmethoxymethyl)-phenyl]-1H-imidazole-4-carboxylic acid ethyl ester;

1-Biphenyl-3-yl-1H-imidazole-4-carboxylic acid ethyl ester;

1-[3-(6-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazole-4-carboxylic acid ethyl ester;

1-(3-Nitro-phenyl)-1H-imidazole-4-carboxylic acid;

1-(3-Nitro-phenyl)-1H-imidazole-4-carboxylic acid pyridin-3-yl ester;

1-(3-Bromo-phenyl)-1H-imidazole-4-carboxylic acid pyridin-3-yl ester;

1-(5′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid ethyl ester;

1-(T-Methoxy-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid ethyl ester;

1-(2′-Cyano-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid ethyl ester;

1-(2′-Chloro-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid ethyl ester;

1-(2′-Trifluoromethoxy-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid ethyl ester;

1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid ethyl ester;

1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid ethyl ester;

1-[3-(2-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazole-4-carboxylic acid ethyl ester;

1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazole-4-carboxylic acid ethyl ester;

1-[3-(2-Fluoro-pyridin-4-yl)-phenyl]-1H-imidazole-4-carboxylic acid ethyl ester;

1-[3-(2-Chloro-pyridin-3-yl)-phenyl]-1H-imidazole-4-carboxylic acid ethyl ester;

1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazole-4-carboxylic acid ethyl ester;

1-Biphenyl-3-yl-1H-imidazole-4-carboxylic acid;

1-(5′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid;

1-(T-Methoxy-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid;

1-(T-Cyano-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid;

1-(2′-Chloro-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid;

1-(T-Trifluoromethoxy-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid;

1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid;

1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazole-4-carboxylic acid;

1-[3-(2-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazole-4-carboxylic acid;

1-[3-(2,4-Difluoro-pyridin-3-ye-phenyl]-1H-imidazole-4-carboxylic acid;

1-[3-(2-Fluoro-pyridin-4-yl)-phenyl]-1H-imidazole-4-carboxylic acid;

1-[3-(2-Chloro-pyridin-3-yl)-phenyl]-1H-imidazole-4-carboxylic acid;

1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazole-4-carboxylic acid;

stereoisomers and mixtures of stereoisomers thereof;

or a pharmaceutically acceptable salt thereof.

7. A pharmaceutical composition, comprising a therapeutically effective amount of a compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, together with at least one pharmaceutically acceptable carrier, excipient or diluent.