GB915129A - New steroid compounds and a process for their preparation - Google Patents

Abstract

The invention comprises salts of testerone 3,5-disulphamylbenzoate of the general formula <FORM:0915129/IV (b)/1> wherein M represents an alkali metal or a quaternary ammonium salt forming group, and the 3,5-dinitrobenzoate of testosterone, and the preparation of the salts of the above general formula wherein M represents an alkali metal by esterifying testosterone with a functional derivative of 3,5-dinitrobenzoic acid to form testosterone 3,5-dinitrobenzoate, treating this compound with a mixture of alkali metal sulphite and bisulphite in the presence of a solvent e.g. dimethylformamide, to form the 3,5-disulphamylbenzoate of testosterone and isolating this compound in the form of a relatively water insoluble salt, and converting this salt into the required alkali metal salt by double decomposition. The above process may be modified for the preparation of the sodium salt in that the potassium salt is first produced, the free sulphonic acid groups are then liberated e.g. by contact with an ion exchange resin, and are then neutralised with sodium hydroxide to form the sodium salt which is precipitated by the addition of a water-miscible solvent e.g. ethanol. A quaternary ammonium salt may be added to form the insoluble salt in the above process e.g. benzyl dimethyl 2 - [2- (p-1,1,3,3-tetramethylbutyl - phenoxy) - ethoxy] - ethyl ammonium chloride.