| 摘要 |
<p>1425636 15,16 - Methylene - estr - 4 - enes SCHERING AG 12 Feb 1973 [11 Feb 1972] 6821/73 Heading C2U [Also in Division A5] Novel steroids of the formula wherein R<SP>1</SP> is C 1-5 alkyl; R<SP>2</SP> is H or acyl; R<SP>3</SP> is H or an optionally substituted aliphatic hydrocarbon group of at most 5 carbon atoms (exclusive of substituents); and X is O or H (OR<SP>4</SP>) in which OR<SP>4</SP> is in the alpha or beta position and R<SP>4</SP> is H or acyl are prepared from steroids of the formulµ wherein Y is a protected keto group and the dotted lines in the rings indicate the presence of a #<SP>5</SP>- or #<SP>5(10)</SP>-double bond and when a #<SP>5(10)</SP>- double bond is present then the 10-H atom is absent, by reduction in the 17-position or conversion to a 17α-substituted-17#-ol followed when required, by hydrolysis to a free #<SP>4</SP>-3-one and, if desired, by hydrogenation of a 17α- unsaturated group and/or reduction to a 3-ol and/or acylation of a free OH group. 3,3 - (2<SP>1</SP>,2<SP>1</SP> - Dimethyl - 1<SP>1</SP>,3<SP>1</SP> - propylenedioxy)- 18 - methyl - 15α,16α- methylene - #<SP>5</SP> or #<SP>5(10)</SP>- estren-17-one is prepared from 3,3-(2<SP>1</SP>,2<SP>1</SP>-dimethyl - 1<SP>1</SP>,3<SP>1</SP> - propylenedioxy) - 18 - methyl - 19- nor - #<SP>5,16</SP> or <SP>15(10),16</SP> - pregnadien - 20 - one (prepared from the #<SP>4</SP>-3-one and 2,2-dimethyl-1,3- propane-diol) by oxygenation to give the corresponding #<SP>15</SP> - 17α- ol, reduction of this to the corresponding 20-ol, reaction of this with methylene iodide in the presence of a Zn-Cu couple to give 17α,20# - dihydroxy - 3,3 - (2<SP>1</SP>,2<SP>1</SP>- dimethyl - 1<SP>1</SP>,3<SP>1</SP> - propylenedioxy) - 18 - methyl- 15α,16α- methylene - 19 - nor - #<SP>5</SP>- or #<SP>5(10)</SP>- pregnene and oxidation of this. 3,3-(2<SP>1</SP>,2<SP>1</SP> -dimethyl - 1<SP>1</SP>,3<SP>1</SP> - propylenedioxy) - 15α,16α- methylene - #<SP>5</SP> or <SP>15(10)</SP> - estren - 17 - one is prepared similarly via corresponding intermediates. The novel steroids are stated to possess a strong androgenic and anabolic activity or a strong gestagenic activity and they may be made up into pharmaceutical compositions with suitable carriers. The gestagenic compounds can be used, possibly together with estrogens, in contraceptive preparations (see Heading A5B).</p> |
