GB1101791A - New 1ª‡:7ª‡-dimethyl steroids and a process for their manufacture - Google Patents

Abstract

Novel compounds of the general formula <FORM:1101791/C2/1> in which R1 represents a hydrogen atom or a saturated or unsaturated aliphatic radical and R2 represents a hydrogen atom, the acyl radical of an organic carboxylic acid or the radical of a physiologically acceptable inorganic acid are obtained in a process wherein the double bond in compounds of the formula <FORM:1101791/C2/2> is reduced, if necessary after shielding of the 3-keto group, and if necessary, a free 17b -hydroxyl group is esterified with an organic carboxylic acid or a reactive derivative thereof or with a physiologically acceptable inorganic acid or a 17b -ester is hydrolysed, and if R1 in the compounds used as starting materials represents hydrogen and the end-products required are compounds in which R1 represents a saturated or unsaturated aliphatic group, the 3-keto group in 1a ,7a -dimethylandrostanes of the formula <FORM:1101791/C2/3> first formed is shielded and the 17b -hydroxyl group is oxidized and subsequently the resulting 17-keto group is converted by the Grignard reaction into the <FORM:1101791/C2/4> group in which R1 represents the saturated or unsaturated aliphatic radical and the 3-keto group is reformed by elimination of the 3-keto shield, and finally, if desired, the 17b -hydroxyl group is esterified with the desired organic acid or a reactive derivative thereof or with a physiologically acceptable inorganic acid. Reduction may be effected by means of metallic lithium in liquid ammonia. Pharmaceutical compositions having androgenic and anabolic activity and containing the above compounds are administered orally or parenterally.