A procedure for preparing compounds as therapeutic agents comprising derivatives in N-phenyl indoline. (Machine-translation by Google Translate, not legally binding)

摘要

A process for preparing compounds of formula I of the specification, and their pharmaceutically acceptable acid addition salts, provided that when R1, R2 and R3 are each methyl, X is an oxygen atom and benzene rings are unsubstituted, so it is CnH2n, other than ethylene, characterized by reacting a compound of the formula **(See formula)** (in which any benzene ring may be substituted, as already described and R3 has been defined above), (a) with a compound with an alcohol group of the formula **(See formula)** (in which neither R1 nor R2 are hydrogen) or of the formula Hal (Cn-1 H2n-2) CN in which (Cn-1 H2n-2) represents a bivalent saturated lower aliphatic hydrocarbon group, in which n is at least 2, and reduce the cyano group, or of the formula Br- (CnH2n) Cl, and react the bromoalcoyl derivative thus formed with a secondary amine of the formula R1 R2 NH, in which neither R1 nor R2 are hydrogen and when the compound of formula I being prepared is an indoline, reduce the product previously formed and, if desired, at any desired moment in the reaction sequence, carry out one or more of the following operations, (b) When R1 is an alcoholic group and when R2 is methyl, remove it by treatment with an alkoxycarbonyl group, followed by hydrolysis, or when R2 is benzyl, replace the benzyl group with a hydrogen atom by catalytic de-benzylation; (c) when at least one of R1 and R2 is hydrogen, converting it into compounds in which R1 and/or R2 is alcoholic or benzyl by alcoholization or benzylation; (d) when the compound of formula I is substituted in the 5-position with a halogen, mitro, sulfamoyl, N-substituted sulfamoyl, hydroxyl or lower alkoxy group which forms these groups by halogenation; nitration, sulfonation followed by conversion of the derivative formed to the N-substituted sulfoyl or sulfamoyl group; or by acetylation followed by conversion of the 5-acetyl compound to a 5-hydroxy or 5-alkoxy group by well known methods; (e) forming the pharmaceutically acceptable acid addition salts of the foregoing. (Machine-translation by Google Translate, not legally binding)