1-benzenesulfonyl-1,3-dihydro-indol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present

A compound of the formula ##STR158## in which R.sub.1 and R.sub.2 are each independently a hydrogen, a hydroxy, a C.sub.1 -C.sub.7 -.omega.-halogenoalkoxy, a halogen, a C.sub.1 -C.sub.7 -alkyl, a trifluoromethyl, a C.sub.1 -C.sub.7 -alkoxy, a C.sub.1 -C.sub.7 -polyhalogenoalkoxy, a C.sub.2 -C.sub.7 -.omega.-hydroxyalkoxy, an .omega.-methoxyalkoxy in which the alkyl is C.sub.2 -C.sub.7, a C.sub.2 -C.sub.7 -.omega.-aminoalkoxy which is free or substituted by one or two C.sub.1 -C.sub.7 -alkyls;

• a C.sub.3 -C.sub.7 -cycloalkoxy;
• a cycloalkyl methoxy in which the cycloalkyl is C.sub.3 -C.sub.7 ;
• a phenoxy, a benzyloxy;
• a C.sub.1 -C.sub.7 -alkylthio;
• a phenylthio;
• a nitro;
• an amino which is free or substituted by one or two C.sub.1 -C.sub.7 -alkyls;
• a cyano;
• a C.sub.1 -C.sub.7 -acyl;
• a C.sub.1 -C.sub.7 -acyloxy;
• a C.sub.1 -C.sub.7 -alkylsulfonamido;
• a phenylsulfonamido;
• a benzylsulfonamido;
• a C.sub.1 -C.sub.7 -alkylamido;
• a C.sub.1 -C.sub.7 -alkoxycarbonylamino;
• a ureido which is unsubstituted or substituted by a phenyl, by a benzyl or by one or two C.sub.1 -C.sub.7 -alkyls;
• or a thioureido which is unsubstituted or substituted by a phenyl, by a benzyl or by one or two C.sub.1 -C.sub.7 -alkyls;
• R.sub.3 and R.sub.4, together form a group --(CH.sub.2).sub.p X(CH.sub.2).sub.q --
• R.sub.5 and R.sub.6 are each independently a hydrogen, a halogen, a C.sub.1 -C.sub.7 -alkyl, a trifluoromethyl, a cyano, a nitro, an amino which is free or substituted by one or two C.sub.1 -C.sub.7 -alkyls;
• a hydroxyamino;
• a hydroxy;
• a carboxy;
• a guanidino which is unsubstituted or mono-substituted or disubstituted by a C.sub.1 -C.sub.7 -alkyl, a phenyl or a benzyl;
• a group OR.sub.7 ;
• a group SR.sub.7 ;
• a C.sub.1 -C.sub.7 -acyl;
• a C.sub.1 -C.sub.7 -alkoxycarbonyl;
• a phenoxycarbonyl;
• a benzyloxycarbonyl;
• a carbamoyl substituted by groups R'.sub.6 and R".sub.6 ;
• a thiocarbamoyl which is free or substituted by one or two C.sub.1 -C.sub.7 -alkyls;
• a sulfamoyl;
• an alkylsulfamoyl or dialkylsulfamoyl in which the alkyl is C.sub.1 -C.sub.7 ;
• a group SO.sub.2 R'.sub.7 ;
• an alkylsulfonamido in which the alkyl is C.sub.1 -C.sub.7 ;
• a phenylsulfonamido;
• a benzylsulfonamido;
• a group COR'.sub.7 ;
• a group NR.sub.8 R.sub.9 or a group CO--NH--CR.sub.10 R'.sub.10 -COR.sub.12 ;
• if appropriate, the phenyl group forming part of the substituent R.sub.5 and/or R.sub.6 can be unsubstituted or monosubstituted or polysubstituted by a C.sub.1 -C.sub.7 -alkyl, a trifluoromethyl, a C.sub.1 -C.sub.7 -alkoxy, a halogen, a sulfamoyl, an alkylsulfamoyl in which the alkyl is C.sub.1 -C.sub.7, a carboxy, an alkoxycarbonyl in which the alkyl is C.sub.1 -C.sub.7, a C.sub.1 -C.sub.7 -acyloxy or an imidazolyl;
• R'.sub.6 and R".sub.6 are each independently hydrogen, a C.sub.1 -C.sub.7 -alkyl which is unsubstituted or substituted by one or more halogens or by R"'.sub.6 :
• a phenyl, a pyridyl, a methylpyridyl, a piperidin-4-yl or a methylpiperidin-4-yl;
• or R'.sub.6 and R".sub.6 form, with the nitrogen atom to which they are bonded, a pyrrolidino group which is unsubstituted or substituted by a hydroxymethyl or by a carbamoyl which is free or substituted by one or two C.sub.1 -C.sub.7 -alkyls;
• R"'.sub.6 is a hydroxy;
• a C.sub.1 -C.sub.7 -alkoxy;
• an amino which is free or substituted by one or two C.sub.1 -C.sub.7 -alkyls, a carbamoyl which is free or substituted by one or two C.sub.1 -C.sub.7 -alkyls or in which the two substituents, together with the nitrogen atom to which they are bonded, form a pyrrolidino, a piperidino or an azepino;
• a cyano;
• a carboxy which is free or esterified by a C.sub.1 -C.sub.7 -alkyl or by a benzyl;
• a phenyl;
• a C.sub.3 -C.sub.7 -cycloalkyl;
• an adamantyl or a heterocyclic radical selected from pyridyl, methylpyridyl, furanyl, tetrahydrofuranyl, thienyl, methylthienyl, pyrrolidino, piperidino and azepino groups;
• R.sub.7 is a C.sub.1 -C.sub.7 -alkyl, a phenyl, a benzyl, a C.sub.3 -C.sub.7 -cycloalkyl, a C.sub.2 -C.sub.7 -alkenyl, a C.sub.1 -C.sub.7 -.omega.-halogenoalkyl, a C.sub.1 -C.sub.7 -polyhalogenoalkyl, a C.sub.1 -C.sub.7 -acyl, a C.sub.1 -C.sub.7 -.omega.-carboxyalkyl which is free or esterified by a C.sub.1 -C.sub.7 -alkyl or by a benzyl;
• a C.sub.2 -C.sub.7 -.omega.-aminoalkyl in which the amino group is free, substituted by one or two C.sub.1 -C.sub.7 -alkyls or in the form of an ammonium ion;
• or a C.sub.1 -C.sub.7 -.omega.-carbamoylalkyl which is free or substituted by one or two C.sub.1 -C.sub.7 -alkyls;
• R'.sub.7 is a piperazin-1-yl group which is unsubstituted or substituted in the 4-position by a group R".sub.7 ;
• a piperidino group which is unsubstituted or substituted in the 4-position by a group R"'.sub.7 ;
• an azetidin-1-yl group which is unsubstituted or substituted in the 3-position by a group R"'.sub.7 ;
• a pyridyl group which is unsubstituted or substituted by a methyl;
• or a pyrrolidino group which is unsubstituted or substituted by a group R"".sub.7 ;
• R".sub.7 is a C.sub.1 -C.sub.7 -alkyl, a phenyl, a benzyl or a C.sub.1 -C.sub.7 -acyl;
• R"'.sub.7 is R".sub.7 or an amino which is free or carries a protecting group;
• R"".sub.7 is R"'.sub.7 or a carboxy group which is free or esterified by a C.sub.1 -C.sub.7 -alkyl;
• R.sub.8 and R.sub.9 are each independently a hydrogen, a C.sub.1 -C.sub.7 -alkyl or a benzyl;
• R.sub.9 can also be a C.sub.3 -C.sub.8 -alkene in which the double bond is in the C.sub.3 -C.sub.4 -position;
• a C.sub.1 -C.sub.7 -acyl;
• a C.sub.1 -C.sub.7 -thioacyl;
• a cycloalkylcarbonyl in which the cycloalkyl is C.sub.3 -C.sub.7 ;
• a cycloalkylthiocarbonyl in which the cycloalkyl is C.sub.3 -C.sub.7 ;
• a C.sub.1 -C.sub.7 -.omega.-aminoacyl;
• a C.sub.1 -C.sub.7 -.omega.-hydroxyacyl;
• a C.sub.1 -C.sub.7 -.omega.-benzyloxyacyl;
• a phenoxycarbonyl;
• a thienocarbonyl;
• a pyridylcarbonyl;
• a methylpyridylcarbonyl;
• a C.sub.1 -C.sub.7 -alkoxycarbonyl;
• a benzoyl;
• a phenacetyl;
• a group CO--CR.sub.10 R'.sub.10 --NR.sub.11 R'.sub.11 ;
• a group CR.sub.10 R'.sub.10 COR.sub.12. a group (CH.sub.2).sub.t COR.sub.12 ;
• a group CO(CH.sub.2).sub.t' COR.sub.12 ;
• a carbamoyl which is unsubstituted or substituted by R.sub.14 and R'.sub.14 ;
• a thiocarbamoyl which is unsubstituted or substituted by R.sub.14 and R'.sub.14, or a heterocyclic radical selected from pyrazolyl, imidazolyl, triazolyl, tetrazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyridyl and thiazolyl groups;
• or
• R.sub.8 and R.sub.9, together with the nitrogen atom to which they are bonded, form hydantoin, N-methylhydantoin or a heterocycle selected from pyrrole, dihydropyrrole, pyrrolidine and isoindole, in which the benzene ring can be unsubstituted or substituted by a halogen, a C.sub.1 -C.sub.7 -alkyl, a trifluoromethyl or a methoxy;
• R.sub.10 and R'.sub.10 are each independently hydrogen, a C.sub.1 -C.sub.7 -alkyl or a benzyl, or R.sub.10 and R'.sub.10, together with the carbon atom to which they are bonded, form a C.sub.3 -C.sub.7 -cycloalkyl;
• R.sub.11 and R'.sub.11 are each independently hydrogen or a C.sub.1 -C.sub.7 -alkyl;
• R.sub.12 is a hydroxy, a C.sub.1 -C.sub.7 -alkoxy or an amino which is unsubstituted or substituted by one or two C.sub.1 -C.sub.7 -alkyls;
• R.sub.13 is hydrogen;
• a C.sub.1 -C.sub.7 alkyl;
• a phenyl;
• a benzyl;
• a C.sub.1 -C.sub.7 acyl;
• a C.sub.1 -C.sub.7 -alkoxycarbonyl;
• or a carbamoyl which is unsubstituted or substituted by one or two C.sub.1 -C.sub.7 alkyls;
• R.sub.14 and R'.sub.14 are each independently a C.sub.1 -C.sub.7 -alkyl which is unsubstituted or substituted by R.sub.15, a phenyl which is unsubstituted or substituted by R'.sub.15, a C.sub.3 -C.sub.7 -cycloalkyl or an adamantyl;
• or
• R.sub.14 and R'.sub.14, together with the nitrogen atom to which they are bonded, form a heterocycle selected from morpholine, thiomorpholine, piperazine, azetidine, pyrrolidine, piperidine and azepine, said heterocycle being unsubstituted or substituted by one or more methyl groups, by a phenyl or by an amino group which is free or carries a protecting group;
• R.sub.15 is a phenyl, a pyridyl, a hydroxy, a C.sub.1 -C.sub.7 -alkoxy, an amino which is free or substituted by one or two C.sub.1 -C.sub.7 -alkyls, or a carboxy which is free or esterified by a C.sub.1 -C.sub.7 -alkyl;
• R'.sub.15 is a hydroxy or an amino which is free or substituted by one or two C.sub.1 -C.sub.7 -alkyls;
• m is 1 or, if R.sub.6 is a halogen, a C.sub.1 -C.sub.7 -alkyl or a C.sub.1 -C.sub.7 -alkoxy, m can also be 2, 3 or 4, or else (R.sub.6).sub.m can be m substituents having different meanings selected from halogen, C.sub.1 -C.sub.7 -alkyl and C.sub.1 -C.sub.7 -alkoxy;
• p and q are each an integer, it being possible for their sum to vary from 3 to 6;
• t is an integer which can vary from 2 to 5;
• t' is an integer which can vary from 1 to 5;
• X is oxygen;
• a group S(O).sub.n ;
• or a group N(O)R.sub.13 ;
• and
• n is O, 1 or 2;
• and its salts.