GB1192825A - Improvements in or relating to 6alpha,7alpha-Methylene and -Halomethylene Steroids - Google Patents

Abstract

1,192,825. 6α,7α - Methylene- and halomethylene-steroids. SYNTEX CORP. 26 July, 1967, No. 34331/67. Heading C2U. Novel steroids of the formulµ (wherein X is H, Cl or F; R<SP>1</SP> is OH or O acyl; R<SP>2</SP> is H, OH, O acyl or, with R<SP>1</SP>, alkylidenedioxy; R<SP>3</SP> is H, α- or #-CH 3 , or in (II) and (III) together with R<SP>2</SP>, 1-alkoxy-alk-1,1-ylidenedioxy; R<SP>4</SP> is H, Cl or F; R<SP>5</SP> is OH or Cl, R<SP>4</SP> being Cl when R<SP>5</SP> is Cl; R<SP>7</SP> is H or CH 3 ; R<SP>8</SP> is H or phenyl which may be Cl-, F-, CH 3 O- or CH 3 -substituted; and Z is a carbon-carbon single or double bond, being single when R<SP>7</SP> is H) are prepared from the corresponding #<SP>6</SP>- steroids by reaction with dimethylsulphoxonium methylide or with an alkali or alkaline earth metal salt of an acid WCHXCOOH where W is Cl, I or Br and X is Cl or F. The 6α,7α-isomers are separated from the usually formed mixtures with the 6#,7#-compounds by standard procedures. Hydroxy groups which become esterified during the reactions can be regenerated by alkaline hydrolysis; alternatively they may be protected. The products may be subjected to conventional procedures to introduce or interconvert substituents and double bonds. These processes and the preparation of starting materials are described in Specification 1,192,824. The 6α,7α - methylene and -halomethylene steroids of the invention have variously corticoid, anti-inflammatory and progestational activity, and the progestational agents also possess varying degrees of anti-androgenic, anti-estrogenic and anti-gonadotrophic activity; and they may be made up into pharmaceutical compositions with suitable carriers.