GB1035917A - New sulphonamides and process for preparing same - Google Patents

Abstract

The invention comprises sulpha-pyrimidines of the formula <FORM:1035917/C2/1> wherein one of R1 and R2 is a lower alkoxy-lower alkyl group and the other is hydrogen, halogen or a lower alkyl, lower alkoxy, lower alkoxy-lower alkyl or lower alkoxy-lower alkoxy group (the word "lower" indicating a group of 1-6 carbon atoms), and Z1 is an amino, nitro, azo or acylamino group, with the exception of 6 - sulphanilamido - 2 - methoxymethyl - 4 - methoxy pyrimidine; salts and N1-acyl derivatives of the sulphanilamides of the above formula; corresponding 6-bis(p-Z-benzenesulphonyl) -amino pyrimidines and processes for the preparation of these compounds by reacting a p-substituted benzenesulphonyl halide with a 4-amino-pyrimidine, or reacting a p-substituted benzenesulphonamide with a 4-halo-pyrimidine or a pyrimidine-4-trialkylammonium compound and, if desired, converting a nitro, azo or acylamino group in a resulting compound into an amino group by reduction or hydrolysis, N1-acylating the product and converting any free compound obtained into a salt or a salt into a free compound. 2 - Lower - alkoxy - lower - alkyl - 4 - R4 - 6 R7 - pyrimidines in which R4 is a hydrogen or halogen atom or a lower alkoxy or lower alkoxy-alkoxy group and R7 is a free hydroxyl, mercapto or amino group or a substituted mercapto, e.g. alkyl mercapto or benzyl mercapto group or a halogen atom, used as starting materials, are made by reacting an amidine of an alkoxy-alkanoic acid with a malonic acid diethyl ester or diacetonitrile and, if desired, converting hydroxyl groups in the 4- and/or 6-position of the resulting pyrimidine into a halogen atom (e.g. with phosphorus oxychloride) and/or a hydroxyl group in the 6-position to a mercapto group and/or a halogen atom in the 6-position into an amino or free or substituted mercapto group and any free mercapto group in the 6-position into a substituted amine group and/or a free or substituted mercapto group into a free amino group and/or a halogen atom in the 4-position into a lower alkoxy or lower alkoxy-alkoxy group or replacing it by hydrogen. Alkoxy-alkanoic-amidines, e.g. methoxy- and ethoxy-acetamidine and methoxy propionamidine are made by treating the appropiate nitrile with ethanolic hydrogen chloride and reacting the resulting imino-ether with ammonia. Pharmaceutical preparations for the treatment of bacterial infections in man and animals comprise the above compounds of the invention in admixture or conjunction with a pharmaceutically suitable carrier. The preparations may suitably take the form tablets, dragees, salves, creams, solutions, suspensions or emulsions or animal feedstuff additives.