GB1377975A - 17alpha-hydroxy-16alpha,18-dimethyl-delta4-pregnene-3,20-dione and its esters - Google Patents
17alpha-hydroxy-16alpha,18-dimethyl-delta4-pregnene-3,20-dione and its estersInfo
- Publication number
- GB1377975A GB1377975A GB5173971A GB5173971A GB1377975A GB 1377975 A GB1377975 A GB 1377975A GB 5173971 A GB5173971 A GB 5173971A GB 5173971 A GB5173971 A GB 5173971A GB 1377975 A GB1377975 A GB 1377975A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- methyl
- converting
- dione
- hydrolysing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Landscapes
- Steroid Compounds (AREA)
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.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19702056512 DE2056512A1 (en) | 1970-11-10 | 1970-11-10 | 17 alpha-hydroxy-16 alpha, 18-dimethyl-4-pregnen-3,20-dione and its esters |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1377975A true GB1377975A (en) | 1974-12-18 |
Family
ID=5788360
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5173971A Expired GB1377975A (en) | 1970-11-10 | 1971-11-08 | 17alpha-hydroxy-16alpha,18-dimethyl-delta4-pregnene-3,20-dione and its esters |
Country Status (11)
Country | Link |
---|---|
AT (3) | AT308985B (en) |
BE (1) | BE775190A (en) |
CH (3) | CH591519A5 (en) |
CS (3) | CS166290B2 (en) |
DE (1) | DE2056512A1 (en) |
DK (1) | DK127851B (en) |
ES (1) | ES394771A1 (en) |
FR (1) | FR2113873B1 (en) |
GB (1) | GB1377975A (en) |
HU (1) | HU163628B (en) |
NL (1) | NL7115418A (en) |
-
1970
- 1970-11-10 DE DE19702056512 patent/DE2056512A1/en active Granted
-
1971
- 1971-08-31 CS CS690971A patent/CS166290B2/cs unknown
- 1971-08-31 CS CS691073A patent/CS166291B2/cs unknown
- 1971-08-31 CS CS622471A patent/CS166289B2/cs unknown
- 1971-09-03 DK DK433271A patent/DK127851B/en unknown
- 1971-09-03 ES ES394771A patent/ES394771A1/en not_active Expired
- 1971-11-01 CH CH1287475A patent/CH591519A5/xx not_active IP Right Cessation
- 1971-11-01 CH CH1287375A patent/CH601348A5/xx not_active IP Right Cessation
- 1971-11-01 CH CH1588371A patent/CH590886A5/xx not_active IP Right Cessation
- 1971-11-08 HU HUSE000360 patent/HU163628B/hu unknown
- 1971-11-08 GB GB5173971A patent/GB1377975A/en not_active Expired
- 1971-11-09 NL NL7115418A patent/NL7115418A/xx unknown
- 1971-11-09 AT AT966571A patent/AT308985B/en not_active IP Right Cessation
- 1971-11-09 FR FR7140076A patent/FR2113873B1/fr not_active Expired
- 1971-11-09 AT AT585172A patent/AT319490B/en not_active IP Right Cessation
- 1971-11-09 AT AT585072A patent/AT319489B/en not_active IP Right Cessation
- 1971-11-10 BE BE775190A patent/BE775190A/en unknown
Also Published As
Publication number | Publication date |
---|---|
FR2113873B1 (en) | 1975-03-14 |
BE775190A (en) | 1972-05-10 |
CS166290B2 (en) | 1976-02-27 |
FR2113873A1 (en) | 1972-06-30 |
DK127851B (en) | 1974-01-21 |
AT308985B (en) | 1973-07-25 |
CS166289B2 (en) | 1976-02-27 |
CH601348A5 (en) | 1978-07-14 |
AT319489B (en) | 1974-12-27 |
DE2056512A1 (en) | 1972-05-18 |
NL7115418A (en) | 1972-05-15 |
CH590886A5 (en) | 1977-08-31 |
AT319490B (en) | 1974-12-27 |
DE2056512C3 (en) | 1980-12-04 |
CS166291B2 (en) | 1976-02-27 |
ES394771A1 (en) | 1974-03-01 |
DE2056512B2 (en) | 1980-04-03 |
CH591519A5 (en) | 1977-09-30 |
HU163628B (en) | 1973-09-27 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |