GB823940A - Steroid compounds - Google Patents
Steroid compoundsInfo
- Publication number
- GB823940A GB823940A GB869/56A GB86956A GB823940A GB 823940 A GB823940 A GB 823940A GB 869/56 A GB869/56 A GB 869/56A GB 86956 A GB86956 A GB 86956A GB 823940 A GB823940 A GB 823940A
- Authority
- GB
- United Kingdom
- Prior art keywords
- triketo
- hydroxy
- acetoxy
- acetoxyallopregnane
- collidine
- 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
- 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
-
- 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 D 1: 4-3,11-diketosteroids of the pregnane series having the general formula <FORM:0823940/IV (b)/1> in which R is a hydrogen atom or an acyl radical, and processes for the preparation of D 1:4-3,11-diketo steroids by treating the corresponding 2,4 - dihalo -, 2 - halo - D 4-, 2,2,4 - trihalo - or 4 - halo - D 1 - 3,11 - diketo - steroids with a dehydrohalogenating agent, particularly a tertiary amine, e.g. collidine, or a nitrogenous carbonyl reagent, e.g. 2,4 - dinitrophenylhydrazine or semicarbazide, followed by hydrolysis, e.g. with pyruvic acid, or in the case of 2,2,4-trihalo steroids, by means of an alkali metal iodide. Preferred D 1: 4-compounds obtainable by the process include D 1: 4 - 3,11,20 - triketo - 17 a -hydroxy - 21 - acyloxy pregnadienes, especially the 21-acetate, propionate and benzoate. In examples: (1) D 1 - 4 - bromo - 3,11,20 - triketo - 17a - hydroxy - 21 - acetoxy - pregnene is refluxed with collidine, the mixture acidified and D 1: 4 - 3,11,20 - triketo - 17a - hydroxy-21-acetoxypregnadiene extracted with chloroform and purified by chromatography on alumina; subsequent hydrolysis in benzene with methanolic KOH gives the free 17,21-diol; (2) 3,11,20 - triketo - 17a - hydroxy - 21 - acetoxyallopregnane (prepared by hydrogenation of cortisone acetate over palladium oxide) is treated with bromine in chloroform yielding 2,4-dibromo - 3,11,20 - triketo - 17a - hydroxy - 21-acetoxyallopregnane, which with 2,4-dinitrophenylhydrazine under nitrogen yields the corresponding 3 - hydrazone of D 1: 4 - 3,11,20-triketo - 17a - hydroxy - 21 - acetoxy - pregnadiene; subsequent warming with pyruvic acid in acetic acid yields the free trione; (3) 3,11,20-triketo - 17a - hydroxy - 21 - acetoxy - allopregnane is brominated in the presence of HBr, yielding 2,2,4-tribromo-allodihydrocortisone acetate, which is refluxed with sodium iodide in acetone and the product refluxed with g - collidine to give D 1: 4 - 3,11,20 - triketo-17a - hydroxy - 21 - acetoxy - pregnadiene; (4) 3,11,20 - triketo - 17a - hydroxy - 21 - acetoxyallopregnane is brominated in chloroform and then dehydrohalogenated using semicarbazide and then pyruvic acid to yield a mixture of D 1 - 3,11,20 - triketo - 17a - hydroxy - 21 - actoxypregnene and the corresponding D 1: 4-pregnadiene, separable by recrystallization; (5) 3,11,20 - triketo - 17a - hydroxy - 21 - acetoxyallopregnane 3 - semi - carbazone is brominated in acetic acid containing a trace of HBr, and the mixture hydrolysed as in (1) to give D 1: 4 - 3,11,20 - triketo - 17a ,21 - dihydroxypregnadiene. D 1 - 4 - Bromo - 3,11,20 - triketo - 17a - hydroxy - 21 - acetoxy pregnane is prepared by brominating 3,11,20 - triketo - 17a - hydroxy-21-acetoxypregnane, separating the 2-bromo derivative from the 4-bromo derivative, refluxing it with collidine and brominating the resulting D 1 - 3,11,20 - triketo - 17a - hydroxy - 21 - acetoxypregnane.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US823940XA | 1955-01-14 | 1955-01-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB823940A true GB823940A (en) | 1959-11-18 |
Family
ID=22170912
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB869/56A Expired GB823940A (en) | 1955-01-14 | 1956-01-10 | Steroid compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB823940A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114130369A (en) * | 2021-12-06 | 2022-03-04 | 武汉汇研生物科技股份有限公司 | Virus exclusion composite chromatographic medium and preparation method thereof |
-
1956
- 1956-01-10 GB GB869/56A patent/GB823940A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114130369A (en) * | 2021-12-06 | 2022-03-04 | 武汉汇研生物科技股份有限公司 | Virus exclusion composite chromatographic medium and preparation method thereof |
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