ES258380A1 - Isoindoline derivatives and methods of preparing same - Google Patents

Abstract

The invention comprises compounds of the general formula <FORM:0916101/IV (b)/1> (wherein Hal represents a halogen atom, R1 represents a C1-5 alkyl group and R2 represents hydrogen or a C1-5 alkyl group) and the preparation thereof by reacting a compound of the general formula <FORM:0916101/IV (b)/2> (wherein X represents chlorine or bromine) or <FORM:0916101/IV (b)/3> (wherein Y represents hydrogen or a methyl or ethyl group) with a compound of the general formula R2-NH2 IV or by reacting a compound of the general formula <FORM:0916101/IV (b)/4> (wherein Z represents chlorine or bromine) with a compound of the general formula R1-NH2 VI or (when R1 and R2 are identical) reacting a compound of the general formula <FORM:0916101/IV (b)/5> with at least two molecular proportions of a compound VI. The products are pharmaceutically useful on account of their diuretic, saluretic and hypotensive activity. Lactones of the general formulae II and VII are prepared by treating compounds III and VIII respectively with mineral acid halides. Acids and esters of the general formula III are prepared by reacting compounds VIII with compounds VI under relatively mild conditions. Lactams of the general formula V are prepared by nitrating 1-oxo-3-(p-halophenyl)-3-hydroxyisoindolines, reducing the nitration products, diazotizing the amino compounds and treating the diazonium salts with sulphur dioxide in the presence of copper chloride or bromide. Sulphohalides of the general formula VIII are prepared by nitrating the 41-halo-2-carboxybenzophenones resulting from FriedelCrafts condensation of halobenzenes with phthalic anhydrides or phthalic acid ester halides, reducing the 41-halo-31-nitro-2-carboxybenzophenones so formed, diazotizing the resulting 31-amino compounds and decomposing the diazonium halides with sulphur dioxide in the presence of copper salts.