Patent IL-102703-A (IL)
Title: N-sulfonyl indoline derivatives carrying an amide functional group, their preparation and pharmaceutical compositions containing them
IPC: C07D295/192
Filed: 1992-07-31
Abstract: Compounds with affinity for the vasopressin and ocytocin receptors of the formula R2OH R3R4N (R1)nSO2 (CH2)m R5 in which R1 is a halogen atom, a C1-C4 alkyl, a hydroxyl, a C1-C4 alkoxy, a benzyloxy group, a cyano group, a trifluoromethyl group, nitro group or an amino group; R2 is a C1-C6 alkyl, a C3-C7 cycloalkyl, a C5-C7 cycloalkene or a phenyl which is unsubstituted or monosubstituted or polysubstituted by a C1-C4 alkyl, a C1-C4 alkoxy, a halogen, a trifluoromethyl group or an amino group, or R2 is a nitrophenyl which is unsubstituted or monosubstituted by a trifluoromethyl group or monosubstituted or polysubstituted by a C1-C4 alkyl or a halogen; R3 is a hydrogen atom; R4 is a carbamoyl group of formula CONR6R7; R5 is a C1-C4 alkyl; a l-naphthyl; a 2-naphthyl; a 5-dimethylamino-1-naphthyl; a phenyl which is un-substituted or substituted by one or more substituents selected from a halogen atom, a C1-C4 alkyl, a trifluoromethyl group, an amino group which is free or substituted by one or 2 C1-C4 alkyls, a hydroxyl, a C1-C4 alkoxy, a C2-C4 alkenoxy, a C1-C4 alkylthio, a trifluoromethoxy group, a benzyloxy group, a cyano group, a carboxyl group, a C1-C4 alkoxycarbonyl group, a carbamoyl group which is free or substituted by one or two C1-C4 alkyls or a C1-C4 alkylamido group, or R5 is a nitrophenyl which is unsubstituted or monosubstituted by a trifluoromethyl group or a C2-C4 alkenoxy or mono- or poly- substituted by a halogen, a C1-C4 alkyl, a C1-C4 alkoxy, a C1-C4 alkylthio, a trifluoromethoxy group or a benzyloxy group; R6 is a C1-C6 alkyl or R6 is similar to R7; R7 is a 4-piperidyl group or a 3-azetidinyl group, the said groups being substituted or unsubstituted on the nitrogen by a C1-C4 alkyl, by a benzyloxy-carbonyl or by a C1-C4 alkoxycarbonyl; a group (CH2)r which is itself substituted by a phenyl group, 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 C1-C4 alkyls, a carboxyl group, a C1-C4 alkoxycarbonyl group, a benzyloxycarbonyl group or a carbamoyl group which is free or substituted by one or 2 C1-C4 alkyls; or R6 and R7 together, with the nitrogen atom to which they are connected, form a heterocycle selected from: morpholine, thiomorpholine, thiazolidine or 2, 2-dimethylthiazolidine, unsubstituted or substituted by R8, piperazine, unsubstituted or substituted at the 4-position by a group R"8, an unsaturated, 5-membered ring containing a single nitrogen atom and substituted by R8 or a saturated, 3-, 4-, 5-, 6- or 7-membered ring containing a single nitrogen atom and substituted by R8 and R9; or an azetidinyl group substituted by a t-butoxy-carbonyl group; R8 is R(8 or a group (CH2)r which is itself substituted by a hydroxyl or by an amino which is free or substituted by one or two C1-C4 alkyls; R(8 is a group (CH2)q which is 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 two C1-C4 alkyls or an aminocarbothioyl group which is free or substituted by one or two C1-C4 alkyls; R"8 is R(8 or a group (CH2)2NH2, which is free or substituted by one or two C1-C4 alkyls or a methyl group; R9 is hydrogen, a halogen, a group (CH2)rOR10, a group (CH2)rNR11R12, a group (CH2)5CONR11R(11 or an azido 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-C4 alkyl or R11 is hydrogen or methyl and R12 is a benzyloxycarbonyl 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 is not zero when R8 or R9 is at the alpha- position of the intracyclic amide nitrogen; s is 0 or 1; as well as their possible salts.