New sulphonamides and process for preparing same

摘要

The invention comprises compounds of the formula wherein one of the symbols R1 and R2 represents a p-amino-, p-nitro-, p-azo- or p-acyl-amino - benzenesulphonamido group and the other represents hydrogen or a C1- 6 alkyl group and Ph represents a phenyl group, optionally bearing a C1- 6 alkyl or alkoxy or a halogen or CF3 substituent, salts, e.g. alkali-, alkaline earth or earth-metal salts, and N1-acyl, e.g. N1-alkanoyl, derivatives of the above sulphanilamides; and processes for their manufacture by condensing the appropriate p-substituted benzenesulphonyl halide with a 4- or 5-amino-1,2,3-triazole, or by reacting a benzenesulphonamide with a 4- or 5-halo-1,2,3-triazole and/or if necessary converting any p-nitro-, azo- or acylamino-substituent to an amino substituent by reduction or hydrolysis, converting any bisbenzenesulphonyl - aminotriazole formed into the mono-compound and/or N1-acylating the product and/or converting into a salt or a salt into a free compound. 4 - Amino - 1 - phenyl - 1,2,3 - triazoles, e.g. 1 - phenyl- and 1 - phenyl - 5 - methyl-, 4-amino-1,2,3-triazole, used as starting materials are made by reacting the appropriate phenyl azide with propiolic acid t-butyl ester, transesterifying the resulting l-phenyl-1,2,3-triazole-4-carboxylic acid t-butyl ester to the methyl or ethyl ester, converting to the amide and subjecting to Hoffmann degradation with bromine. Alternatively, e.g. in the case of 4-amino-1-(p-chlorophenyl)-1,2,3-triazole, propiolic acid is used in place of the t-butyl ester and the resulting 1-(p-chlorophenyl) - 1,2,3 - triazole - 4 - carboxylic acid converted via the acid chloride, the azide and the urethane. Pharmaceutical and veterinary preparations having anti-bacterial activity comprise the sulphanilamide compounds of the invention and a carrier suitable for enteral, parenteral or local administration. The veterinary preparations may take the form of additives for animal feedstuffs.