GB1016955A - 6,16-dimethyl 15-dehydrosteroids and processes for their production - Google Patents
6,16-dimethyl 15-dehydrosteroids and processes for their productionInfo
- Publication number
- GB1016955A GB1016955A GB4440162A GB4440162A GB1016955A GB 1016955 A GB1016955 A GB 1016955A GB 4440162 A GB4440162 A GB 4440162A GB 4440162 A GB4440162 A GB 4440162A GB 1016955 A GB1016955 A GB 1016955A
- Authority
- GB
- United Kingdom
- Prior art keywords
- give
- oxido
- steroids
- alkali metal
- compound
- 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
- C07J75/00—Processes for the preparation of steroids in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises compounds of the formula <FORM:1016955/C2/1> (wherein X is H or F; Y is a -H, b -OH or =O; and Z is a free or esterified hydroxyl group) and their D 1-, D 6-, and D 1,6-analogues; and their preparation by reacting 6,16-dimethyl-16a , 17a oxido-progesteron in any sequence with an acid in the presence of water and a watermiscible solvent to split the 16a ,17a -epoxide ring, with an 11-hydroxylating micro-organism, and with an alkaline iodine solution and then an alkali metal acylate to introduce a 21-ester group which may subsequently be saponified and, if desired, re-esterified, to give a product wherein Y is b -OH and X is hydrogen. The 11-hydroxy steroid may then be dehydrated to the corresponding D 9(11)-compound, this reacted with HOBr and an alkali metal acylate to form the corresponding 9b ,11b -oxido-compound, and this treated with HF to give the corresponding 9a -fluoro-11b -hydroxy-steroid. The 11-hydroxysteroids may be oxidized with mild oxidizing agents to give the 11-keto-steroids. Double bonds may be introduced at the 1- and/or 6-positions by treatment with chemical or microbiological dehydrogenating agents. Examples are given. The steroids of the invention, which are stated to have anti-inflammatory properties, may be made up into pharmaceutical or veterinary compositions with suitable carriers. Oily and aqueous solutions, suspensions, emulsions, tablets, dragees, ointments and creams are referred to. They may also contain preserving, stabilizing or wetting agents, or salts to influence the osmotic pressure, or buffers.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM0050979 | 1961-11-24 | ||
| DEM51015A DE1211187B (en) | 1961-11-29 | 1961-11-29 | Process for the production of delta 1,4- or delta 1,4,6-6, 16-dimethyl-15-dehydro-steroids |
| DEM51048A DE1211188B (en) | 1961-12-02 | 1961-12-02 | Process for the preparation of 6, 16-dimethyl-15-dehydro-steroids |
| DEM51103A DE1211189B (en) | 1961-12-07 | 1961-12-07 | Process for the preparation of 6, 16-dimethyl-15-dehydro-steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1016955A true GB1016955A (en) | 1966-01-12 |
Family
ID=27437223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4440162A Expired GB1016955A (en) | 1961-11-24 | 1962-11-23 | 6,16-dimethyl 15-dehydrosteroids and processes for their production |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1016955A (en) |
-
1962
- 1962-11-23 GB GB4440162A patent/GB1016955A/en not_active Expired
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