GB969393A - Steroids - Google Patents

Abstract

The invention comprises steroids of the general formula <FORM:0969393/C1/1> wherein R1 represents hydrogen or R2, R2 represents an aliphatic acid acyl radical containing not more than 4 carbon atoms, and R3 represents hydrogen or an alkyl or aliphatic carboxylic acyl radical containing not more than 4 carbon atoms, and a process for the preparation of a ,b -unsaturated keto-steroids by treating 13b -methyl-11, 17-diketo-steroids of the androstane or oestrone series saturated at the 1,2-position with an aliphatic monocarboxylic acid anhydride with 3 to 8 carbon atoms containing 0.1 to 5 per cent by weight of a strong acid and isolating the 17b -methyl-17a -acyloxy -11-keto -12- ene-steroid thus obtained as well as the relevant 17b -methyl -17a - acyloxy -12-acyl -11- keto -12- ene-steroid and, if desired, converting the latter compound into the 17b -methyl -17a - acyloxy -11- keto -12- ene-steroid by repeating the treatment with the carboxylic acid anhydride containing acid. The preferred reactants for use in the above are of the general formula <FORM:0969393/C1/2> wherein R1 represents hydrogen or the methyl group, R2 represents hydrogen, or a hydroxy, methyl or alkoxy group, R3 represents a keto, hydroxy, alkoxy or acyloxy group, R4 represents hydrogen, chlorine or fluorine or a methyl, hydroxy or keto group, R5 represents a keto group or (H, 0H), R6 represents hydrogen or, in conjunction with R7, a keto group, R7 represents hydrogen or chlorine or a hydroxy or methyl group, and R8 represents hydrogen or fluorine, and the said reactants may contain double bonds, for example at the 1-, 3-, 4-, 5-, 5(10)- and 6-position. Products containing an acyloxy group may be subjected to hydrolysis to hydrolyse the acyloxy group, products containing a hydroxy group may be oxidised to convert the hydroxy group to a keto group or converted to an acyloxy group, and products saturated at the 1,2-position may be dehydrogenated to form a 1,2-double bond. Therapeutic compositions, which may be in the form of pills, tablets, coated pills, emulsions, solutions or injectable solutions, contain as the active ingredients 17b -methyl -17a - acyloxy -11-keto -12- ene-steroids and 17b -methyl -17a -acyloxy -12- acyl -11- keto -12- ene steroids.