GB1377975A - 17alpha-hydroxy-16alpha,18-dimethyl-delta4-pregnene-3,20-dione and its esters - Google Patents

Abstract

1377975 17α - Hydroxy - 16α,18 - dimethyl- #<SP>4</SP> - pregnene - 3,20 - dione SCHERING AG 8 Nov 1971 [10 Nov 1970] 51739/71 Heading C2U The novel title steroid and its novel 17α- monoesters and 3-enol-17α-diesters are prepared by reducing 17α-hydroperoxy-16α,18-dimethyl- #<SP>4</SP> - pregnene - 3,20 - dione or a 3 - protected derivative thereof or by oxidizing a 3#-hydroxy- 17α - acyloxy - 16α,18 - dimethyl - #<SP>5</SP> - pregrien- 20-one or the corresponding 17α-ol and, when desired, hydrolysing or esterifying the product. 3-Enol-17α-diesters thus-produced may subsequently be partially hydrolysed to 17α- monoesters. 17α - Hydroperoxy - 16α,18 - dimethyl - #<SP>4</SP>- pregnene - 3,20 - dione is prepared by converting 17# - acefoxy - 18 - methyl - #<SP>5(10)</SP>- estren-3#-ol (prepared by reduction of the 3-one) to 17# - acetoxy - 18 - methyl - 5,10# - methylene- 5# - estran - 3# - ol, oxidizing this to the corresponding 3-one, converting this to 17#- acetoxy - 18 - methyl - #<SP>4</SP> -androsten - 3 - one, converting this to the #<SP>5</SP> - 3 - ethyleneketal, hydrolysing this to the 17#-ol, oxidizing this to 3,3 - ethylenedioxy - 18 - methyl- #<SP>5</SP>-androsten-17-one, converting this to the corresponding 17α - ethynyl - 17# - ol, dehydrating to 18 - methyl - 17 - ethynyl - #<SP>4,16</SP> - androstadien-3-one, oxidizing this to 18-methyl-#<SP>4,16</SP>- pregnadiene - 3,20 - dione, ketalizing this to 3,3 - (2<SP>1</SP>,2<SP>1</SP> - dimethylpropylene - dioxy) - 18- methyl - #<SP>5,16</SP> - pregnadien - 20 - one, converting this to 3,3 - (2<SP>1</SP>,2<SP>1</SP> - dimethylpropylenedioxy) - 17α- hydroperoxy - 16α,18 - dimethyl - #<SP>5</SP> - pregnen- 20-one and hydrolysing this. 3# - Hydroxy - 17α - acyloxy - 16α,18 - dimethyl - #<SP>5</SP> - pregnen - 20 - ones (wherein acyl is heptanoyl, formyl or acetyl) are prepared by converting 3#-acetoxy-18-methyl-#<SP>5,16</SP>-pregnadien - 20 - one to 17α - hydroperoxy - 3#- acetoxy - 16α,18 - dimethyl - #<SP>5</SP> - pregnen - 20- one, hydrolysing this to the 3#-ol, reducing this to 3#,17α - dihydroxy - 16α,18 - dimethyl - #<SP>5</SP>- pregnen-20-one, converting this to the 3#,17α- diacylate and partially hydrolysing this. The novel steroids are stated to possess strong ovulation-inhibiting properties coupled with a minor gestagenic activity, and they may be made up into pharmaceutical compositions with suitable carriers. These compositions may be used for contraceptive purposes. Reference has been directed by the Comptroller to Specification 1,277,266.