GB988803A - New steroid compounds, and processes for their preparation - Google Patents

Abstract

The invention comprises 11-(5b -androst-9(11)-en - 17b - yl) - 31,51,81 - trioxa - bicyclo - [2,2,2]-octane derivatives having the general formula <FORM:0988803/C2/1> in which R represents either a hydrogen atom or an acyl radical derived from a lower organic carboxylic acid having 1-7 carbon atoms, and processes for the preparation thereof in which a 3a ,211 - diacyloxy - 20,20 - bis - acyloxy-methylene - 11b - hydroxy - 5b - pregnane having the general formula <FORM:0988803/C2/2> (wherein Ac represents an acyl radical derived from a lower organic carboxylic acid having form 1-7 carbon atoms) is reacted with a dehydrating agent to form the corresponding 3a ,21 - diacyloxy - 20,20 - bis - acyloxymethylene - 5b - pregn - 9(11) - ene which is then saponified by treatment with alkali to form 3a , 21 - dihydroxy - 20,20 - bis - hydroxymethylene - 5b - pregn - 9(11) - ene, and the latter is subjected to condensation with a lower alkyl orthoformate to yield 11-(3a -hydroxy-5b -androst - 9(11) - en - 17b - yl) - 31, 51, 81 - trioxabicyclo - [2,2,2] - octane. As dehydrating agent there may be employed perchloric acid in acetic acid, or methane sulphonyl chloride and pyridine in N,N-dimethylformamide. Condensation may be effected in the presence of p-toluenesulphonic acid. Compositions for use in human and veterinary medicine having pharmacodynamic activities and containing compounds of the first of the above formulae are administered orally in tablets, powders, pills, syrups or elixirs, by injection in sterile liquid medium, or by the body cavities in the form of a suppository. Specification 988,801 is referred to.