US 5,849,780 AGranted

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

AssigneeSanofi

InventorsAlain Di Malta, Loic Foulon, Georges Garcia, Dino Nisato, Richard Roux, Claudine Serradeil-Legal, Gerard Valette, Jean Wagnon

Life of this patent

Estimating the term…

Abstract

The invention relates to 1-Benzenesulfonyl-1,3-dihydroindol-2-one derivatives of the formula ##STR1## and their salts, where appropriate, to their preparation and to pharmaceutical compositions in which they are present. These compounds have an affinity for the vasopressin and/or ocytocin receptors.

Claims31

Dependent claims

A compound of 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 with the carbon to which they are bonded, form an optionally fused, saturated or unsaturated C.sub.3 -C.sub.12 hydrocarbon ring which is unsubstituted or substituted by one or more C.sub.1 -C.sub.7 -alkyl groups, by an oxo group, by a C.sub.3 -C.sub.5 -spirocycloalkyl or by a hydroxy which is free or substituted by a group selected from the group consisting of C.sub.1 -C.sub.4 -alkyl groups, C.sub.1 -C.sub.2 -alkoxyalkyl groups in which the alkyl is C.sub.1 -C.sub.4, phenylalkoxyalkyl groups in which the alkoxy is C.sub.1 -C.sub.2 and the alkyl is C.sub.1 -C.sub.4, and tetrahydrofuranyl and tetrahydropyranyl groups;
or else
R.sub.5 and R.sub.6 are each independently a hydrogen, a halogen, a C.sub.1 -C.sub.7 -alkyls, a trifluoromethyl, a cyano, a nitro, an amino which is free or substituted by one or two C.sub.1 -C.sub.7 -alkyl;
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 ;
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.alpha..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 with a physiologically acceptable anion;
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 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.-benzyl-oxyacyl;
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, 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 the group consisting of 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 and 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.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;
t is an integer which can vary from 2 to 5;
t' is an integer which can vary from 1 to 5;
and its salts.

98 more elements

A compound of the formula ##STR169## in which R.sub.1 and R.sub.2 are each independently a hydrogen, a hydroxy, a halogen, a C.sub.1 -C.sub.7 -alkyl, a trifluoromethyl, a C.sub.1 -C.sub.7 -alkoxy, a C.sub.2 -C.sub.7 -.omega.-hydroxyalkoxy, 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 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;
C.sub.1 -C.sub.7 -acyloxy;
a C.sub.1 -C.sub.7 -alkylamido;
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;
R.sub.3 and R.sub.4, together with the carbon to which they are bonded, form a cyclopentane, a cycloheptane, a tetrahydrofuran, an adamantane, a tricyclo-5.2.1.0.sup.2,6 !dec-8-ene, a bicyclo2.2.1!heptane, a bicyclo3.3.1 !nonane or a cyclohexane which is unsubstituted or substituted by a C.sub.3 -C.sub.5 -spirocycloalkyl or by one or two C.sub.1 -C.sub.7 -alkyl groups,
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 hydroxy;
a carboxy;
a group OR.sub.7 ;
(C.sub.1 -C.sub.4)alkylthio;
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;
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 ;
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, a carboxy 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;
R'".sub.6 is a hydroxy;
a C.sub.1 -C.sub.7 -alkoxy;
a carboxy which is free or esterified by a C.sub.1 -C.sub.7 -alkyl or by a benzyl;
R.sub.7 is a C.sub.1 -C.sub.7 -alkyl, a phenyl, a benzyl, 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;
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 with a physiologically acceptable anion;
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 piperazine-1-yl group which is unsubstituted or substituted in the 4-position by a group R".sub.7 ;
R".sub.7 is a C.sub.1 -C.sub.7 -alkyl;
R'".sub.7 is 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.1 -C.sub.7 -acyl;
a cycloalkylcarbonyl in which the cycloalkyl is C.sub.3 -C.sub.7 ;
a cycloalkylthio-carbonyl 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.-benzyloxyacyl;
a phenoxycarbonyl;
a thienocarbonyl;
a benzoyl;
a phenacetyl;
a carbamoyl which is unsubstituted or substituted by a phenyl or one or two C.sub.1 -C.sub.4 alkyls;
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;
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, and its salts.

55 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/323,921Filed 17 Oct 1994 · continuation in part
Priority: FR 92 0103430 Jan 1992
Granted: 15 Dec 1998
Term ends: Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 209/34
Oxygen atoms: in position 2
C07D 209/92
Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles: naphthostyrils
C07D 209/96
Ring systems containing three or more rings: spiro-condensed ring systems
C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links

Family

Serial129,310Parent of this continuation-in-part · filed 30 Sep 1993
US 5,849,780 AThis patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

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 with the carbon to which they are bonded, form an optionally fused, saturated or unsaturated C.sub.3 -C.sub.12 hydrocarbon ring which is unsubstituted or substituted by one or more C.sub.1 -C.sub.7 -alkyl groups, by an oxo group, by a C.sub.3 -C.sub.5 -spirocycloalkyl or by a hydroxy which is free or substituted by a group selected from the group consisting of C.sub.1 -C.sub.4 -alkyl groups, C.sub.1 -C.sub.2 -alkoxyalkyl groups in which the alkyl is C.sub.1 -C.sub.4, phenylalkoxyalkyl groups in which the alkoxy is C.sub.1 -C.sub.2 and the alkyl is C.sub.1 -C.sub.4, and tetrahydrofuranyl and tetrahydropyranyl groups;
or else
R.sub.5 and R.sub.6 are each independently a hydrogen, a halogen, a C.sub.1 -C.sub.7 -alkyls, a trifluoromethyl, a cyano, a nitro, an amino which is free or substituted by one or two C.sub.1 -C.sub.7 -alkyl;
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 ;
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.alpha..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 with a physiologically acceptable anion;
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 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.-benzyl-oxyacyl;
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, 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 the group consisting of 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 and 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.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;
t is an integer which can vary from 2 to 5;
t' is an integer which can vary from 1 to 5;
and its salts.

98 more elements

Facts

Application

08/323,921Filed 17 Oct 1994 · continuation in part

Priority

FR 92 0103430 Jan 1992

Granted

15 Dec 1998

Term ends

Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 209/34
Oxygen atoms: in position 2
C07D 209/92
Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles: naphthostyrils
C07D 209/96
Ring systems containing three or more rings: spiro-condensed ring systems
C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links