GB795452A - Pregnadiene derivatives - Google Patents
Pregnadiene derivativesInfo
- Publication number
- GB795452A GB795452A GB16497/55A GB1649755A GB795452A GB 795452 A GB795452 A GB 795452A GB 16497/55 A GB16497/55 A GB 16497/55A GB 1649755 A GB1649755 A GB 1649755A GB 795452 A GB795452 A GB 795452A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pregnadiene
- ethylenedioxy
- diketo
- acid
- prepared
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises esters of 3-ethylenedioxy - 11,20 - diketo - 21 - hydroxy - D 5,16-pregnadiene of the general formula: <FORM:0795452/IV (b)/1> wherein R represents an acyloxy group, and the preparation thereof by reacting 3-ethylenedioxy - 11,20 - diketo - D 5,16 - pregnadiene - 21-oxalyl acid with iodine in the presence of a base and reacting the iodoketone thus formed with a salt of an organic carboxylic acid, e.g. sodium or potassium acetate, sodium propionate or sodium benzoate. The treatment with iodine may be carried out in two stages, first by reaction in a solution of a weak base, e.g. aqueous disodium hydrogen phosphate, and the reaction is then completed by the addition of a strong base such as potassium hydroxide. A suitable reaction temperature range is approximately 0 DEG to 25 DEG C. The treatment with the salt of a carboxylic acid may be carried out in a refluxing solvent such as acetone. The above process may be modified in that the 3-ethylenedioxy-11,20-diketo - D 5,16 - pregnadiene - 21 - oxalyl acid is prepared by hydrolysing an ester of 3-ethylenedioxy - 11,20 - diketo - D 5,16 - pregnadiene - 21-oxalyl acid, and the ester of 3-ethylenedioxy-11,20-diketo - D 5,16 - pregnadiene - 21 - oxalyl acid may be prepared by reacting 3-ethylenedioxy-11,20 - diketo - pregnadiene with an organic oxalate, e.g. dimethyl or diethyl oxalate, in the presence of a basic substance such as an alkali-metal hydroxide, hydride, or alkoxide-particularly sodium and potassium methoxide and ethoxide, a suitable reaction temperature being from 0 DEG to 100 DEG C., e.g. room temperature. The above process may be further modified in that the 3 - ethylenedioxy - D 5,16 - pregnadiene-11,20-dione is prepared by a method claimed in Specification 792,410. The group R is preferably derived from an alkanoic acid, e.g. an acid containing 2 to 10 carbon atoms. In the examples, 3-ethylenedioxy- D 5,16-pregnadiene - 11,20 - dione - 21 - ol - 21 - acetate is prepared. Specification 795,454 also is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US795452XA | 1954-06-30 | 1954-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB795452A true GB795452A (en) | 1958-05-21 |
Family
ID=22151225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16497/55A Expired GB795452A (en) | 1954-06-30 | 1955-06-08 | Pregnadiene derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB795452A (en) |
-
1955
- 1955-06-08 GB GB16497/55A patent/GB795452A/en not_active Expired
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