GB826364A - Cyclopentanopolyhydrophenanthrene compounds - Google Patents
Cyclopentanopolyhydrophenanthrene compoundsInfo
- Publication number
- GB826364A GB826364A GB867/56A GB86756A GB826364A GB 826364 A GB826364 A GB 826364A GB 867/56 A GB867/56 A GB 867/56A GB 86756 A GB86756 A GB 86756A GB 826364 A GB826364 A GB 826364A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fluoro
- hydroxy
- allopregnane
- diketo
- acetoxy
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0826364/IV (b)/1> in which R is a hydrogen atom or an acyl radical other than -COCH2C(CH3)3 and -PO(OH)2, Y is halo, and Z is keto or b -hydroxy, together with a process for their preparation (including that of compounds wherein R is -COCH2C (CH3)3) by reacting a 2,4-dibromo-9a -halo-3,20 - diketo - 11 - oxygenated - 17a - hydroxy-21-acyloxy-allopregnane with a dehydrohalogenating agent, which may be a tertiary amine, e.g. collidine, or a nitrogenous ketone reagent, in which case the 3-keto group which couples with the reagent is subsequently liberated by reaction with a compound containing a free carbonyl group in the presence of an organic acid. The 21-acyl group may be finally removed by hydrolysis. Specified products of the invention are the 9a -chloro- and 9a -fluoro- D 1,4-3,20-diketo - (11b - hydroxy - or 11 - keto -) - 17a ,21-dihydroxy pregnadienes and the corresponding 21-acetates and propionates. In examples: (1) 9a - fluoro - 3,11,20 - triketo - 17a - hydroxy-21 - acetoxy - allopregnane is brominated in chloroform, and the resulting 2,4-dibromo derivative treated with 2,4-dinitrophenylhydrazine giving D 1,4 - 3,11,20 - triketo - 9a - fluoro-17a - hydroxy - 21 - acetoxypregnadiene-(2,4 - dinitrophenylhydrazone) which with pyruvic acid in aqueous acetic acid gives the free trione; (2) as in (1), using the corresponding 11b -hydroxy compound to give D 1,4-9a -fluoro-3,20 - diketo - 11b ,17a - dihydroxy - 21 - acetoxy-pregnadiene; (3) and (4), 9a - fluoro - 3,20-diketo - 11b ,17a - dihydroxy - 21 - acetoxy-allopregnane is brominated in acetic acid containing HBr, and the 2,4-dibromo compound dehydrobrominated with collidine in dimethyl-formamide to the product of (2), which (5), is saponified to 9a -fluorohydroretrocortin; (6), 9a - fluoro - 3,11,20 - triketo - 17a - hydroxy-21-acetoxy-allopregnane treated as in (4) to (6) yields 9a -fluoro-retrocortin. Specifications 826,362, 826,365 and 826,369 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US826364XA | 1955-01-14 | 1955-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB826364A true GB826364A (en) | 1960-01-06 |
Family
ID=22172413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB867/56A Expired GB826364A (en) | 1955-01-14 | 1956-01-10 | Cyclopentanopolyhydrophenanthrene compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB826364A (en) |
-
1956
- 1956-01-10 GB GB867/56A patent/GB826364A/en not_active Expired
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