GB826838A - Arylsulfonyl derivatives of bicyclic guanidines - Google Patents

Abstract

The invention comprises compounds of the formula <FORM:0826838/IV (b)/1> wherein n is an integer from 2 to 4, m is an integer from 2 to 3 and Ar is a phenyl radical optionally substituted by alkyl, amino, nitro, acylamino, hydroxy or alkoxy groups, preferably in the para position; and their preparation by reacting the corresponding bicyclic guanidine with an aryl sulphonyl chloride in aqueous alkaline solution in the presence of a solvent such as diethyl ether. The preparation may also be carried out using pyridine as both solvent and acid-binding agent. Compounds in which Ar is an aminophenyl group are made by hydrolysis of the corresponding acylamino compounds. Examples describe the preparation of 1-p-toluenesulphonyl-, 1-p-acetylaminobenzenesulphonyl-, 1 - p - nitrobenzenesulphonyl- and (by hydrolysis) 1-p-aminobenzenesulphonyl-, 2 : 3 : 5 : 6 - tetrahydro - 1 - imidaz-(1 : 2-a)-imidazole; 1-p-toluenesulphonyl- and 1-p-acetylaminobenzenesulphonyl-, D 8-hexahydro-1 : 4 : 8-pyrimidazole and 1-p-toluenesulphonyl-, 1 - p - acetylaminobenzenesulphonyl- and (by hydrolysis) 1 - p - aminobenzenesulphonyl -, D 9 - 1 : 4 : 9 - triazabicyclo - (5 : 3 : 0) - decene. Specification 826,837 is referred to.ALSO:Bacteriostatic preparations for external use comprise sulphonyl derivatives of bicyclic guanidines of the formula <FORM:0826838/VI/1> wherein n is an integer from 2 to 4, m is an integer from 2 to 3 and Ar is a phenyl or alkyl-, amino-, nitro acylamino-, hydroxy- or alkoxy-substituted phenyl group (see Group IV (b)) and a carrier. A cream for external use comprises 1 - p - toluenesulphonyl - D 8 - hexahydro - 1 : 4 : 8 - pyrimidazole, yellow beeswax, wool fat, liquid paraffin and water. Specification 826,837, [Group IV (b)], is referred to.