A method for the production of steroid - 17beta - sulfo acetate - esters of androstan - and oestranreihe

摘要

The invention comprises compounds of the formula FORM:1016372/C2/1 wherein the dotted line in ring A denotes the optional presence of double bonds, R1 represents a hydrogen atom or a methyl group, R2 represents two hydrogen atoms when a D 4 double bond is absent, or a hydrogen or chlorine atom or a hydroxyl group when a D 4 double bond is present, R3 represents a hydrogen atom or an alkyl group preferably having less than six carbon atoms, R4 represents two hydrogen atoms or one hydrogen atom with an a -methyl group, and X represents a chlorine atom or the group -OR in which R represents an alkyl, alkenyl, cycloalkyl, aryl, halo-substituted aryl, aralkyl, alkaryl, alkoxyaryl, aryloxy alkyl or heterocyclic radical. The compounds may be prepared by direct acylation of a steroid compound having a hydroxy group in the 17b position with chlorosulphonylacetyl chloride in an inert solvent to give the sulphonyl chloride. The sulphonate esters may be prepared by reaction of the sulphonyl chloride so produced with an alcohol or directly by addition of an alcohol during the acylation. The sulphoacetates may be prepared from 3,17-androstenediones by protecting the D 4-3-keto position, reducing the 17-keto group and reacting with chlorosulphonyl acetyl chloride. Esters of testosterone-17-sulphoacetate may be prepared by treating testosterone with a Grignard reagent and reacting the resulting 17-halomagnesium compound with chlorosulphonylacetyl chloride and an alcohol. Therapeutic compositions with anabolic and androgenic properties, in the form of oil solutions or aqueous suspensions for parenteral administration, contain esters of androstaneand estrane-17-sulphoacetates of the above general formula.