GB894642A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB894642A GB894642A GB30471/59A GB3047159A GB894642A GB 894642 A GB894642 A GB 894642A GB 30471/59 A GB30471/59 A GB 30471/59A GB 3047159 A GB3047159 A GB 3047159A GB 894642 A GB894642 A GB 894642A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- fluoro
- pregnadiene
- dione
- difluoro
- 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
Abstract
The invention comprises a compound of the general formula <FORM:0894642/IV (b)/1> wherein X111 is a hydrogen or a halogen atom and R11 is b -hydroxy or keto, 21-esters thereof with hydrocarbon carboxylic acids containing 1-12 carbon atoms, a compound of the general formula <FORM:0894642/IV (b)/2> wherein X11 is a chlorine, fluorine or hydrogen atom, a compound of the general formula <FORM:0894642/IV (b)/3> wherein Ac is the acyl radical of a hydrocarbon carboxylic acid containing 1-12 carbon atoms inclusive, a compound of the general formula <FORM:0894642/IV (b)/4> a compound of the formula <FORM:0894642/IV (b)/5> wherein R1 is an alkyl or aryl sulphonyl radical and processes for the preparation thereof by treating 11b ,21-dihydroxy-4,17(20)-[cis]-pregnadiene-3-one with a dialkyl oxalate to form an alkali-metal enolate of the corresponding p 2-alkoxyoxalyl compound II, treating II with perchloryl fluoride to produce a 2-fluoro-2-alkoxyoxalyl compound III, treating III with a base to form 2-fluoro-11b ,21-dihydroxy-4,17(20)-[cis]-pregnadien-3-one IV, esterifying IV to obtain a 21-ester V, oxidatively hydroxylating V to obtain 2 - fluoro - 11b , 17a , 21 - trihydroxy - 4 - pregnene - 3,20-dione 21-acylate VI, dehydrogenating VI with chloranil to obtain 2-fluoro-11b ,17a ,21-trihydroxy-4,6-pregnadiene-3,20-dione 21- acylate VII which may be hydrolysed to form a 21-hydroxy compound or oxidised to form 2-fluoro-17a ,21 - dihydroxy - 4, 6 - pregnadiene - 3, 11, 20 - trione VIII. Compound VII is dehydrated to form the corresponding D 9(11)-compound IX, IX is treated with hypohalous acid to form the 9a -halo-11b -hydroxy compound X, X is treated with a base to form a 9(11)-epoxy compound, which is treated with hydrogen fluoride to obtain 2, 9a - difluoro - 11b , 17a , 21 - trihydroxy - 4, 6 - pregnadiene - 3, 20 - dione 21 - acylate XII. XII XII is oxidised to the corresponding 11-keto compound XIII. 2,21-difluoro compounds are obtained by treating 2-fluoro-11b ,17a ,21-trihydroxy - 4, 6 - pregnadiene - 3, 20 - dione or the corresponding 11-keto compound or their 9a -chloro or fluoro analogues with an organic sulphonyl halide to obtain the corresponding 21-sulphonate ester XVI, treating XVI with sodium iodide to obtain the corresponding 21-iodo compound XVII, and treating XVII with silver fluoride to obtain 2,21-difluoro-11b ,17a -dihydroxy-4,6-pregnadiene-3,20-dione XIX. Alternatively, the 21-sulphonate ester XVI can be treated with potassium fluoride to obtain the 2,21-difluoro compound directly. Illustrative products of the invention are 2-fluoro-11b ,17a ,21-trihydroxy-4,6-pregnadiene-3,20-dione, 2-fluoro-17a ,21-dihydroxy-4,6-pregnadiene-3,11,20-trione, 21-esters thereof and the 2,9a -difluoro and 2,21-difluoro analogues thereof. Specifications 771,344 and 781,712 are referred to.ALSO:Pharmaceutical compositions having anti-inflammatory activity comprise a compound of the formula <FORM:0894642/VI/1> wherein X111 is a halogen or hydrogen atom and R11 is b -hydroxy or keto, or 21-esters thereof with hydrocarbon carboxylic acids containing 1-12 carbon atoms, and a pharmaceutical diluent. They are employed orally as tablets, or topically as ointments, lotions, jellies, creams, suppositories, bougies and acqueous suspensions, with or without coacting antibiotics, e.g. novobiocin, bacitracin, circulin, polymyxin B sulphate gramicidin, streptomycin sulphate, dihydrostreptomycin sulphate, oxytetracycline, chlortetracycline, tetracycline and chloramphenicol, or the sulphonamides. Specifications 771,344 and 781,712 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US894642XA | 1958-09-08 | 1958-09-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB894642A true GB894642A (en) | 1962-04-26 |
Family
ID=22217789
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB30471/59A Expired GB894642A (en) | 1958-09-08 | 1959-09-07 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB894642A (en) |
-
1959
- 1959-09-07 GB GB30471/59A patent/GB894642A/en not_active Expired
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