GB957542A - Cycloalkenyl ethers of 17ª‰-hydroxy androstanes - Google Patents

Abstract

The invention comprises 17-11-cycloalkenyl ethers of 17b -hydroxy-androstanes of the general formula: <FORM:0957542/C2/1> wherein n is 1 or 2 and S represents one of the following groups: <FORM:0957542/C2/2> <FORM:0957542/C2/3> <FORM:0957542/C2/4> <FORM:0957542/C2/5> <FORM:0957542/C2/6> <FORM:0957542/C2/7> <FORM:0957542/C2/8> <FORM:0957542/C2/9> and the D 1-, D 1,4-and D 4,6-dehydro analogues of the compounds having grouping (a); the D 4-dehydro analogues of the compounds having grouping (a) and the corresponding 9a -fluoro-11b -hydroxy, 11b -hydroxy and 11-keto D 4-compounds; the D 4- and D 5(10)-dehydro analogues of the compounds having the grouping (b); the D 1-, D 4-, D 1,4- and D 5(6)- analogues of the compounds having the formula (c) and the lower alkyl ethers and lower alkanoyl esters of the compounds having the grouping (c) as well as of the various dehydro analogues thereof; and the 19-nor-D 4-dehydro analogues of the compounds having the formula (d); and the preparation thereof by reacting a corresponding 17b -hydroxy-steroid having any 3-hydroxy group protected as a lower alkyl ether or a lower alkanoyl ester and an acetal, hemiacetal or enol ether of cyclopentanone or of cyclohexanone derived from an aliphatic alcohol at a temperature higher than 80 DEG C. and thereafter, if desired, hydrolysing a 3-ester group in an alkaline medium. By "lower alkyl" is meant a saturated hydrocarbon radical containing 1 to 5 carbon atoms, and by "lower alkanoyl" is meant the acyl residue of an alkanoic acid containing 1 to 3 carbon atoms. The above process may be extended in the case of a product containing a 3-keto group by reducing the said keto group to a 3-hydroxy group by means of a conventional reduction method, for example by reducing with lithium aluminium hydride or sodium borohydride.