GB943041A - 1-methyl-oestratriene-derivatives and the preparation thereof - Google Patents

Abstract

The invention comprises steroids of the general formula: <FORM:0943041/C2/1> wherein R1 represents <FORM:0943041/C2/2> or =O, R2 represents a hydrogen atom or an alkyl or alkenyl group containing not more than 5 carbon atoms or an ethinyl group, R3 represents a hydrogen atom or an acyl group, R4 represents a hydrogen atom or an alkyl group containing not more than 5 carbon atoms or an acyl group, and R5 represents H, OH or =O, and the corresponding compounds obtained by reacting a 17-keto compound of the above formula with hydroxylamine or an isonicotinic hydrazide, and the preparation of the steroids of the above general formula by treating steroids of the general formula: <FORM:0943041/C2/3> wherein R1, R2 and R3 have the above significance, with a strong acid such as perchloric, sulphuric acid or p-toluenesulphonic acid, or a Lewis acid such as zinc chloride, in the presence of a carboxylic anhydride and, if desired, saponifying the 3-acyloxy group in the product of the first formula to form the corresponding 3-hydroxy compound and, if desired, esterifying or etherifying the hydroxy group. The above process may be modified in that a keto group or keto groups present in the 11- and/or 17-positions of an intermediate or final product is or are reduced to a hydroxy group or hydroxy groups and, if desired, a 17-hydroxy group may be acylated. The above process may also be modified in that either before or after the acid treatment, a 17-keto group is reacted with a Grignard reagent or with an alkali metal acetylide and, if desired, by a subsequent hydrogenation and/or acylation reaction or reactions to form at the 17-position a grouping of the formula <FORM:0943041/C2/4> , wherein R2 and R3 have the above significance, or a 17-keto group in the final product is reacted with hydroxylamine or an isonicotinic hydrazide which may be substituted to form a 17-oxime or a 17-isonicotinic hydrazone. Pharmaceutical compositions having an antilipaemic activity, comprise as the active ingredients steroid compounds of the first general formula above and an additive. The composition may be in the form of a tablet, pill, dragee, suppository, emulsion, suspension or solution for injection.