GB957219A - New steroid compounds and processes for their preparation - Google Patents
New steroid compounds and processes for their preparationInfo
- Publication number
- GB957219A GB957219A GB2705561A GB2705561A GB957219A GB 957219 A GB957219 A GB 957219A GB 2705561 A GB2705561 A GB 2705561A GB 2705561 A GB2705561 A GB 2705561A GB 957219 A GB957219 A GB 957219A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- epoxy
- pregnan
- group
- hydroxy
- 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
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- 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)
- Steroid Compounds (AREA)
Abstract
The invention comprises 11b , 18-epoxy-16a -methyl-20-oxygeno-pregnan-3-one derivatives having the general formula: <FORM:0957219/C2/1> in which both the X and Y are hydrogen or together constitute a 4(5) double bond and the oxygenated grouping Z at the 20-position is =H(O.CO.H), =H(OH) or =O and processes for the preparation thereof by reducing and simultaneously saponifying a 3a -acyloxy-18,20b -epoxy-16a -methyl-5b -pregnan-11-one having the general formula: <FORM:0957219/C2/2> (where Ac represent an acyl radical derived from an organic carboxylic acid) by treatment with an alkaline reducing agent so as to yield 18, 20b -epoxy-3a , 11b -dihydroxy-16a -methyl-5b -pregnane and selectively oxidizing the 3a -hydroxyl group of the latter so as to yield 18, 20b -epoxy-11b -hydroxy-16a -methyl-5b -pregnan-3-one and then treating the latter with formic acid so as to effect migration of the epoxy bridge to the 11b ,18-position and esterifying the hydroxyl group thus created at the 20-position thus yielding the desired 11b , 18-epoxy - 20b - formyloxy - 16a -methyl-5b -pregnan-3-one. A D 4 double bond may be introduced into the product by bromination in 4-position followed by dehydrobromination. The 20-formyloxy group may be hydrolysed to form a 20-hydroxy group which on oxidation gives a 20-keto group. The starting 3a -acetoxy-18, 20b -epoxy-16a -methyl-5b -pregnan-11-one is obtained by reducing at 20-position 3a -acetoxy-16a -methyl-5b -pregnane-11, 20-dione and treating the 20-hydroxy compound thus obtained with lead tetracetate. Specifications 903,808, 957,220 and 957,221 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR834359A FR1365260A (en) | 1960-07-29 | 1960-07-29 | New oxygenated steroid derivatives and method of preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB957219A true GB957219A (en) | 1964-05-06 |
Family
ID=8736474
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2705561A Expired GB957219A (en) | 1960-07-29 | 1961-07-26 | New steroid compounds and processes for their preparation |
| GB4668863A Expired GB957221A (en) | 1960-07-29 | 1961-07-26 | Novel steroid compounds and processes for their preparation |
| GB4668763A Expired GB957220A (en) | 1960-07-29 | 1961-07-26 | A novel steroid compound and processes for its preparation |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4668863A Expired GB957221A (en) | 1960-07-29 | 1961-07-26 | Novel steroid compounds and processes for their preparation |
| GB4668763A Expired GB957220A (en) | 1960-07-29 | 1961-07-26 | A novel steroid compound and processes for its preparation |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH400145A (en) |
| FR (1) | FR1365260A (en) |
| GB (3) | GB957219A (en) |
-
1960
- 1960-07-29 FR FR834359A patent/FR1365260A/en not_active Expired
-
1961
- 1961-07-11 CH CH808761A patent/CH400145A/en unknown
- 1961-07-26 GB GB2705561A patent/GB957219A/en not_active Expired
- 1961-07-26 GB GB4668863A patent/GB957221A/en not_active Expired
- 1961-07-26 GB GB4668763A patent/GB957220A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1365260A (en) | 1964-07-03 |
| GB957221A (en) | 1964-05-06 |
| GB957220A (en) | 1964-05-06 |
| CH400145A (en) | 1965-10-15 |
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