Patent EP-0526348-A1 (EP)
Inventor: WAGNON JEAN
IPC: C07D295/192
Filed: 1992-08-03
Abstract: The invention relates to compounds of formula (I) <IMAGE>  in which   - R1 represents a halogen atom, a C1-C4 alkyl, a hydroxyl, a C1-C4 alkoxy, or a benzyloxy, cyano, trifluoromethyl, nitro or amino group,   - R2 represents a C1-C6 alkyl, a C3-C7 cycloalkyl, a C5-C7 cycloalkene, a phenyl which is unsubstituted or substituted one or a number of times, a C1-C4 alkoxy, a halogen, a trifluoromethyl group, an amino group, or R2 represents a nitrophenyl which is unsubstituted or substituted one or a number of times;   - R3 represents a hydrogen atom;   - R4 represents a carbamoyl group of formula CONR6R7; - R5 represents a C1-C4 alkyl; a 1-naphthyl; a 2-naphthyl; a 5-dimethylamino-1-naphthyl; a phenyl which is unsubstituted or substituted one or a number of times, or R5 represents a nitrophenyl which is unsubstituted or substituted one or a number of times;   - R6 represents a C1-C6 alkyl, or R6 is similar to R7; - R7 represents a 4-piperidinyl group; a 3-azetidinyl group, the said groups being unsubstituted or substituted on the nitrogen by a C1-C4 alkyl, by a benzyloxycarbonyl or by a C1-C4 alkoxycarbonyl; a group (CH2)r itself substituted by a 2-, 3- or 4-pyridyl group, by a hydroxyl group, or by an amino group which is free or substituted by one or two substituents; - or R6 and R7 together constitute, with the nitrogen atom to which they are bonded, a heterocycle chosen from:     . morpholine,   . thiomorpholine, . thiazolidine or 2,2-dimethylthiazolidine, which is unsubstituted or substituted by R8, . piperazine which is unsubstituted or substituted at the 4 position by a group R''8; . a 5-membered mononitrogenated unsaturated ring substituted by R8 or a 3-, 4-, 5-, 6- or 7-membered mononitrogenated saturated ring substituted by R8 and R9;   - R8 represents R'8 or a group (CH2)r itself substituted by a hydroxyl or by an amino group which is free or substituted by one or two C1-C4 alkyls; - R'8 represents a group (CH2)q itself substituted by a carboxyl group, a C1-C4 alkoxycarbonyl group, a benzyloxycarbonyl group, a carbamoyl group which is free or substituted by a hydroxyl or by one or 2 C1-C4 alkyls, or an aminocarbothioyl group which is free or substituted by one or 2 C1-C4 alkyls; - R''8 represents R'8 or a (CH2)2NH2 group which is free or substituted by one or two C1-C4 alkyls; - R9 represents hydrogen, a halogen, a group (CH2)rOR10, a group (CH2)rNR11R12, a group (CH2)sCONR11R'11 or an azido group;   - R11 represents hydrogen, a C1-C4 alkyl, a mesyl or a tosyl; - R11, R'11 and R12 each represent a hydrogen or a C1-C4 alkyl or R11 represents hydrogen and R12 represents a benzyloxycarbonyl or a C1-C4 alkoxycarbonyl;   - n represents 0, 1 or 2;   - m represents 0, 1 or 2;   - q represents 0, 1, 2 or 3; - r represents 0, 1, 2 or 3, with the limitation that r is not 0 when R8 or R9 is in the position  alpha  to the intracyclic amide nitrogen;   - s represents 0 or 1;  and to its optional salts. These compounds are useful in the treatment of illnesses of the central nervous system, of the cardiovascular system and of the gastric sphere in man and animals.