GB1425267A - 6beta,11alpha-dihydroxy-16alpha,17alpha-epoxy-delta4-pregnene- 3,20-dione - Google Patents
6beta,11alpha-dihydroxy-16alpha,17alpha-epoxy-delta4-pregnene- 3,20-dioneInfo
- Publication number
- GB1425267A GB1425267A GB934073A GB934073A GB1425267A GB 1425267 A GB1425267 A GB 1425267A GB 934073 A GB934073 A GB 934073A GB 934073 A GB934073 A GB 934073A GB 1425267 A GB1425267 A GB 1425267A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dione
- pregnene
- give
- dihydroxy
- epoxy
- 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
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
Abstract
1425267 6#,11α - Dihydroxy - 16α,17α - epoxy- #<SP>4</SP>-pregnene-3,20-dione SCHERING AG 26 Feb 1973 [25 Feb 1972] 9340/73 Heading C2U The novel title compound is prepared by fermenting 16α,17α - epoxy - #<SP>4</SP> - pregnene - 3,20- dione with a fungal culture of the genus Aspergillus, e.g. A. ochraceus. It may subsequently be converted to 9α - fluoro - 11#,17α - dihydroxy- 6α,16α - dimethyl - #<SP>1,4</SP> - pregnadiene - 3,20- dione by ketalization to give 11α-hydroxy-3,3- ethylenedioxy - 16α,17α - epoxy - pregnane - 3,20- dione, treatment of this with a Cr (II)-salt to give 11α - hydroxy - 3,3 - ethylenedioxy - #<SP>16</SP>- pregnene - 6,20 - dione, reaction of this with CH 3 MgI in the presence of cuprous chloride, decomposition of the Grignard complex with acetyl chloride, epoxidization with a per-acid and saponification to give 6#,11α,17α-trihydroxy- 3,3 -ethylenedioxy - 6#,16α - dimethyl - pregnan- 20-one, acid hydrolysis and dehydration of this to give 11α,17α - dihydroxy - 6α,16α - dimethyl- #<SP>4</SP> - pregnene - 3,20 - dione, microbiological dehydrogenation of this using Bacillus lentus to the corresponding #<SP>1,4</SP>-compound, reaction of this with mesyl chloride in pyridine followed by treatment with calcium carbonate in DMF to give 17α - hydroxy - 6α,16α - dimethyl - #<SP>1,4,9(11)</SP>- pregnatriene-3,20-dione and conversion of this via the corresponding 9α - bromo - 11# - ol and 9#,11#-epoxide to the required product.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722209746 DE2209746A1 (en) | 1972-02-25 | 1972-02-25 | 6 BETA, 11 ALPHA-DIHYDROXY-16 ALPHA, 17 ALPHA-EPOXY-4-PREGNEN-3,20-DIONE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1425267A true GB1425267A (en) | 1976-02-18 |
Family
ID=5837541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB934073A Expired GB1425267A (en) | 1972-02-25 | 1973-02-26 | 6beta,11alpha-dihydroxy-16alpha,17alpha-epoxy-delta4-pregnene- 3,20-dione |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5535117B2 (en) |
| CH (1) | CH576490A5 (en) |
| DE (1) | DE2209746A1 (en) |
| DK (1) | DK129790B (en) |
| FR (1) | FR2173310B1 (en) |
| GB (1) | GB1425267A (en) |
| NL (1) | NL7302526A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL238288B1 (en) * | 2017-08-09 | 2021-08-02 | Wrocław University Of Environmental And Life Sciences | 6β,11α-dihydroxy-16α,17α-epoxyprogesterone and method for producing 6β,11α-dihydroksy-16α,17α-epoxyprogesterone |
-
1972
- 1972-02-25 DE DE19722209746 patent/DE2209746A1/en active Pending
-
1973
- 1973-02-22 DK DK95073A patent/DK129790B/en unknown
- 1973-02-23 CH CH268473A patent/CH576490A5/xx not_active IP Right Cessation
- 1973-02-23 NL NL7302526A patent/NL7302526A/xx not_active Application Discontinuation
- 1973-02-26 FR FR7306700A patent/FR2173310B1/fr not_active Expired
- 1973-02-26 GB GB934073A patent/GB1425267A/en not_active Expired
- 1973-02-26 JP JP2305573A patent/JPS5535117B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK129790C (en) | 1975-04-28 |
| JPS4930591A (en) | 1974-03-19 |
| NL7302526A (en) | 1973-08-28 |
| DK129790B (en) | 1974-11-18 |
| FR2173310A1 (en) | 1973-10-05 |
| DE2209746A1 (en) | 1973-08-30 |
| CH576490A5 (en) | 1976-06-15 |
| JPS5535117B2 (en) | 1980-09-11 |
| FR2173310B1 (en) | 1976-06-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |