GB806045A - Steroids - Google Patents
SteroidsInfo
- Publication number
- GB806045A GB806045A GB5197/56A GB519756A GB806045A GB 806045 A GB806045 A GB 806045A GB 5197/56 A GB5197/56 A GB 5197/56A GB 519756 A GB519756 A GB 519756A GB 806045 A GB806045 A GB 806045A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- keto
- methyl
- acyloxy
- carbon atoms
- 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
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- 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 9a -halo-17-alkyl-testosterones represented by the formula <FORM:0806045/IV (b)/1> wherein R1 is hydrogen or the acyl radical of a hydrocarbon carboxylic acid containing 1-12 carbon atoms inclusive, R11 is a hydroxyl or keto group, R is methyl or ethyl, R111 is hydrogen or methyl, and X is bromine, chlorine, fluorine or iodine, and the preparation thereof. D 4-3-Keto - 9a - fluoro (or 9a -chloro) - 11b - hydroxy - 17b - hydroxy (or 17b - acyloxy) - 17a - alkyl compounds of the androstane series are obtained by reacting a D 4 - 3 - keto - 9,11b - epoxy - 17b - hydroxy (or 17b - acyloxy) - 17a - alkyl compound of the androstane series wherein the 17a -alkyl group contains less than 3 carbon atoms and the 17-acyloxy group contains 1-12 carbon atoms inclusive, with hydrogen halide in which the halogen is chlorine or fluorine. D 4 - 3 - Keto - 9a - bromo - (or 9a - iodo) - 11b - hydroxy - 17 - hydroxy (or 17 - acyloxy wherein the acyl radical contains 1-12 carbon atoms)-17a -alkyl compounds of the androstane series wherein the 17a -alkyl group contains less than 3 carbon atoms, are obtained by reacting a D 4,9(11) - 3 - keto - 17b - hydroxy or 17b - acyloxy - 17a - alkyl compound of the androstane series with hypobromous or hypoiodous acid. The 11b -hydroxy compounds may be converted to the corresponding 11-keto compounds with chromium trioxide. In examples there is described the preparation of (1) 9a -bromo- and 9a - iodo - 11b - hydroxy - 17 - methyl - testosterone using N-bromacetamide and sodium iodide respectively and the corresponding 17-esters thereof; (2) 9a -fluoro-11b -hydroxy-17-methyltestosterone and the corresponding 17-ethyltestosterone; (3) 9a -fluoro-11b - hydroxy-17 - methyltestosterone - 17 - acetate and other esters; (4) 9a -chloro-11b -hydroxy-17-methyl (and 17-ethyl)-testosterone and 17-esters thereof; (5) 9a -fluoro (and 9a -chloro)-11-keto-17-methyl (and 17-ethyl) testosterone and esters thereof. Specifications 724,149, 806,046 and 806,047 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US806045XA | 1955-08-08 | 1955-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB806045A true GB806045A (en) | 1958-12-17 |
Family
ID=22158421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5197/56A Expired GB806045A (en) | 1955-08-08 | 1956-02-20 | Steroids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB806045A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3336341A (en) * | 1964-03-10 | 1967-08-15 | Smith Kline French Lab | 11-oxygenated b-nortestosterone derivatives |
-
1956
- 1956-02-20 GB GB5197/56A patent/GB806045A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3336341A (en) * | 1964-03-10 | 1967-08-15 | Smith Kline French Lab | 11-oxygenated b-nortestosterone derivatives |
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