GB1066729A - 6-substituted pregnanes - Google Patents
6-substituted pregnanesInfo
- Publication number
- GB1066729A GB1066729A GB5047065A GB5047065A GB1066729A GB 1066729 A GB1066729 A GB 1066729A GB 5047065 A GB5047065 A GB 5047065A GB 5047065 A GB5047065 A GB 5047065A GB 1066729 A GB1066729 A GB 1066729A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- diene
- ethoxy
- bis
- treating
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of formula <FORM:1066729/C2/1> where W is hydrogen, hydroxy or C1- 3 alkanoyloxy, Y is hydrogen or hydroxy, and Z is carbonyl, b -hydroxymethylene or b -C1- 3-alkanoyl-oxymethylene, with the proviso that, when Y is hydrogen, Z is b -hydroxymethylene or b -C1- 3-alkanoyloxymethylene, and their preparation by (a) reaction of a 6-methylene-pregnane with di-methylsulphoxonium methylide, any 17a ,21-dihydroxy compounds being protected by a 17a ,20: 20,21 - bis - methylenedioxy group which is subsequently removed by hydrolysis, followed, if desired, by (b) hydrolysis of a 20b -alkanoyloxy product to a 20b -hydroxy compound, (c) oxidation of a 20b -hydroxy product to a 20-keto compound, or (d) reaction of a 21-hydroxy compound with methane sulphonyl chloride to form the 21-methanesulphonate, reacting this with sodium iodide to form the 21-iodide, and treating this with a reducing agent to form 21-unsubstituted compound. The compounds of the invention have progestational activity. 6 - Methylene - 17a ,20 : 20,21 - bis - methylenedioxy - pregn - en - 3 - one is prepared by reaction of 17a ,20 : 20,21-bis-methylenedioxy-pregn-4-en-3-one with ethyl orthoformate in the presence of an acid catalyst to form the corresponding 3-ethoxy-3,5-diene, reacting this with a mixture of phosgene or phosphorus oxychloride with dimethylformamide to form the 3-ethoxy-6-formyl-3,5-diene, treating this with sodium borohydride to form the 3-ethoxy-6-hydroxymethyl-3,5-diene, and treating this with aqueous acetic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5047065A GB1066729A (en) | 1965-11-26 | 1965-11-26 | 6-substituted pregnanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5047065A GB1066729A (en) | 1965-11-26 | 1965-11-26 | 6-substituted pregnanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1066729A true GB1066729A (en) | 1967-04-26 |
Family
ID=10456003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5047065A Expired GB1066729A (en) | 1965-11-26 | 1965-11-26 | 6-substituted pregnanes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1066729A (en) |
-
1965
- 1965-11-26 GB GB5047065A patent/GB1066729A/en not_active Expired
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