4-(4-imidazolyl) piperidines substituted at position 1, their preparation and also their therapeutic applications

Compounds corresponding to the general formula ##STR112## in which R.sub.1 represents a hydrogen atom or a group --COR.sub.2, in which R.sub.2 represents a phenyl group, cyclopentylmethyl, cyclohexylmethyl, cyclopentylethyl or cyclohexylethyl groups or cyclopentylamino, cyclohexylamino, or phenylamino, chlorophenylamino or dichlorophenylamino groups;

• R represents a hydrogen atom or a group COR.sub.3, in which R.sub.3 represents
• (a) a linear or branched aliphatic group containing 1 to 11 carbon atoms,
• (b) a cyclane ring-system selected from the group consisting of cyclopropane, phenylcyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornane, adamantane, noradamantane, chlorooxonorbornane, chloroethylenedioxynorbornane, bromoethylenedioxynorbornane and the anhydride group of hydroxycarboxy-1,2,2-trimethylcyclopentanecarboxylic acid,
• (c) a phenyl group, unsubstituted or substituted at the para-position with a linear or branched aliphatic group containing 3 to 5 carbon atoms, or with a halogen,
• (d) a group (CH.sub.2).sub.m R.sub.4, in which m is a number between 1 and 10, and R.sub.4 represents a cyclane ring system selected from the group consisting of cyclopropane, cyclobutane, cyclopentane, cyclopentane, cyclohexane, cycloheptane, norbornane, noradamantane, adamantane and 6,6-dimethylbicyclo-heptene;
• a phenyl group unsubstituted or monosubstituted with a fluorine atom, a chlorine atom, a methyl group or a methoxy group;
• a 2-thienyl or 3-thienyl group;
• a carboxylic acid ester group COOR.sub.5 in which R.sub.5 is a cyclane ring-system selected from the group consisting of cyclopropane, cyclobutane, cyclopentane, cyclohexane or norbornane;
• a carboxylic acid amide group of structure CONHR.sub.6, in which R.sub.6 represents a cyclane ring-system selected from the group consisting of cyclopropane, cyclobtuane, cyclopentane, cyclohexane or norbornane;
• a carboxylic acid amide group of structure ##STR113## in which the group ##STR114## represents pyrrolidine, piperidine or 2,6-dimethyl-morpholine;
• or an ether group --O--R.sub.7, it being possible for R.sub.7 to be a phenyl group, unsubstituted or monosubstituted with a chlorine or fluorine atom or disubstituted with a chlorine atom and with a methyl group;
• (e) a group --CH.dbd.CHR.sub.8, in which R.sub.8 represents a cyclane ring-system selected from the group consisting of cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornane or norbornene;
• (f) a secondary amine group --NH(CH.sub.2).sub.n R.sub.9, in which n is a number between 1 and 5 and R.sub.9 constitutes a cyclane ring-system selected from the group consisting of cyclopropane, cyclobutane, cyclopentane, cyclohexane or norbornane, or a phenyl group, unsubstituted, monosubstituted with a fluorine or chlorine atom or with a methoxy group or trisubstituted with methoxy groups;
• R also represents a hydroxyalkenyl group ##STR115## in which p is a number between 2 and 9 and R.sub.10 represents a phenyl group or a phenoxy group;
• as well as a group CSNH(CH.sub.2).sub.n R.sub.9 in which n is a number between 1 and 5 and R.sub.9 has the meaning stated above, provided that when R.sub.1 represents a hydrogen atom or R.sub.2 a phenyl group a cyclopentylamino, cyclohexylamino or phenylamino group, R cannot represent a hydrogen atom, R.sub.3 cannot represents a phenyl group unsubstituted or substituted at the para-position by a methyl group or a halogen, a secondary amine group --NH--(CH.sub.2).sub.1-4 --R.sub.9 in which R.sub.9 represents a cycloalkyl (3 to 6 C), a phenyl group unsubstituted or monosubstituted with a fluorine or chlorine atom and provided that when R.sub.1 represents a hydrogen atom or R.sub.2 a phenyl group, a cyclopentylamino, cyclohexylamino or phenylamino group, R cannot represent a group CSHN(CH.sub.2).sub.1-3 --R.sub.9 in which R.sub.9 has the meaning given above.