N-SULFONYLINDOLINE DERIVATIVES CARRYING AN AMIDE FUNCTIONAL GROUP, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS IN WHICH THEY ARE PRESENT

摘要

Compounds of formula (6): 6in whichA' is NR6R7;- R1 is a halogen atom, a C1-C4 alkyl, a hydroxyl, aC1-C4 alkoxy, a benzyloxy group, a cyano group, atrifluoromethyl group, nitro group or an aminogroup;- R2 is a C1-C6 alkyl, a C3-C7 cycloalkyl, a C5-C7cycloalkene or a phenyl which is unsubstituted ormonosubstituted or polysubstituted by a C1-C4alkyl, a C1-C4 alkoxy, a halogen, a trifluoromethylgroup or an amino group, or R2 is a nitrophenylwhich is unsubstituted or monosubstituted by atrifluoromethyl group or monosubstituted orpolysubstituted by a C1-C4 alkyl, a C1-C4 alkoxy ora halogen;- R5 is a C1-C4 alkyl; a 1-naphthyl; a 2-naphthyl; a5-dimethylamino-1-naphthyl; a phenyl which isunsubstituted or substituted by one or moresubstituents selected from a halogen atom, a C1-C4alkyl, a trifluoromethyl group, an amino groupwhich is free or substituted by one or two C1-C4alkyls, a hydroxyl, a C1-C4 alkoxy, a C2-C4alkenoxy, a C1-C4 alkylthio, a trifluoromethoxygroup, a benzyloxy group, a cyano group, acarboxyl group, a C1-C4 alkoxycarbonyl group, a87carbamoyl group which is free or substituted byone or two C1-C4 alkyls or a C1-C4 alkylamidogroup, or R5 is a nitrophenyl which isunsubstituted or monosubstituted by atrifluoromethyl group or a C2-C4 alkenoxy ormono- or polysubstituted by a halogen, a C1-C4 alkyl, aC1-C4 alkoxy, a C1-C4 alkylthio, a trifluoromethoxygroup or a benzyloxy group;- R6 is a C1-C6 alkyl or R6 is identical to R7;- R7 is a 4-piperidyl group or a 3-azetidinyl group,the said groups being substituted or unsubstitutedon the nitrogen by a C1-C4 alkyl, by abenzyloxycarbonyl or by a C1-C4 alkoxycarbonyl; agroup (CH2)r which is itself substituted by a 2-,3- or 4-pyridyl group, by a hydroxyl group or byan amino group which is free or substituted by oneor two C1-C4 alkyls, a carboxyl group, a C1-C4alkoxycarbonyl group, a benzyloxycarbonyl group ora carbamoyl group which is free or substituted byone or two C1-C4 alkyls;- or R6 and R7 together, with the nitrogen atom towhich they are connected, form a heterocycleselected from:. morpholine,. thiomorpholine,. thiazolidine or 2,2-dimethylthiazolidine,unsubstituted or substituted by R8,. piperazine, unsubstituted or substituted at the4-position by a group R"8,. an unsaturated, a 5-membered ring containing asingle nitrogen atom and substituted by R8 or asaturated, 3-, 4-, 5-, 6- or 7-membered ringcontaining a single nitrogen atom andsubstituted by R8 and R9;- R8 is R'8 or a group (CH2)r which is itselfsubstituted by a hydroxyl or by an amino which isfree or substituted by one or two C1-C4 alkyls;88- R'8 is a group (CH2)q which is itself substitutedby a carboxyl group, a C1-C4 alkoxycarbonyl group,a benzyloxycarbonyl group, a carbamoyl group whichis free or substituted by a hydroxyl or by one ortwo C1-C4 alkyls or an aminocarbothioyl group whichis free or substituted by one or two C1-C4 alkyls;- R"8 is R'8 or a group (CH2)2NH2 which is free orsubstituted by one or two C1-C4 alkyls;- R9 is hydrogen, a halogen, a group (CH2) rOR10, agroup (CH2)rNR11R12, a group (CH2)sCONR11R'11 or anazido group;- R10 is hydrogen, a C1-C4 alkyl, a mesyl or a tosyl;- R11, R'11 and R12 are each a hydrogen or a C1-C4alkyl or R11 is hydrogen and R12 is abenzyloxycarbonyl or a C1-C4 alkoxycarbonyl;- n is 0, 1 or 2;- m is 0, 1 or 2;- q is 0, 1, 2 or 3;- r is 0, 1, 2 or 3, with the limitation that r isnot zero when R8 or R9 is at the alpha-position ofthe intracyclic amide nitrogen;- s is 0 or 1;are useful as intermediates of the preparation ofN-sulfonylindoline derivatives which are useful in thetreatment of complaints of the central nervous system,the cardiovascular system and the gastric sphere inhumans and animals.