GB889310A - Improvements in or relating to steroid compounds - Google Patents

Abstract

The invention comprises steroid compounds of the general formula <FORM:0889310/IV (b)/1> wherein A and R each represent a hydrogen atom or methyl radical and wherein one of the radicals X and Y represents an alkanoylthio radical and the other represents a hydrogen atom or an alkanoylthio radical, the alkanoylthio radical containing less than 9 carbon atoms, and of the general formula <FORM:0889310/IV (b)/2> wherein A, R, X and Y have the above significance and M represents hydrogen, ammonium or an alkali metal. The compounds may be prepared by mixing a thioalkanoic acid of the formula Alkyl-CO-SH with a D 1- and/or D 6 dehydro derivative of the corresponding steroid compound of the general formula <FORM:0889310/IV (b)/3> wherein A and R have the above significance, to form the compounds of the first general formula above. The compounds of the second general formula above are obtained by treating the compounds of the first general formula above with aqueous alkali to form the alkali metal and ammonium salts from which the free acids may be prepared by exposing the salts to a proton source. In the examples the following compounds are prepared: 1a -acetylthio - 17a - (2 - carboxyethyl) - 17b - hydroxy - androst-4-en-3-one lactone, 17a -(2-carboxyethyl)-17b - hydroxy - 1a - propionylthioandrost - 4 - en - 3-one, 7a -acetylthio-, 7a -propionylthio-, and 7a -octanoylthio - 17b - hydroxy - 4 - en - 3 - one lactone, 1a , 7a - diacetylthio - and 1a , 7a - di - propionylthio - 17a - (2 - carboxyethyl) - 17b - hydroxyandrost - 4 - en - 3 - one lactone, 7a - acetylthio - and 7a - propionylthio - 17a - (2 - carboxyethyl) - 17b - hydroxy - 19 - nor - androst - 4-en-3-one lactone, and 7a -acetylthio-17a -(2-carboxyethyl) - 17b - hydroxy - 6 - methylandrost - 4-en-3-one lactone. 17a - (2 - carboxyethyl) - 17b - hydroxy - 19 - nor - androsta - 4, 6 - dien - 3 - one lactone is prepared by reducing the corresponding 19-nor-androst-4-ene with chloranil. 17a - (2 - carboxyethyl) - 17b - hydroxy - 6b - methylandrost-4-en-3-one lactone is prepared by reducing the corresponding androst-4-ene with chloranil.