GB878705A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB878705A GB878705A GB37861/58A GB3786158A GB878705A GB 878705 A GB878705 A GB 878705A GB 37861/58 A GB37861/58 A GB 37861/58A GB 3786158 A GB3786158 A GB 3786158A GB 878705 A GB878705 A GB 878705A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dione
- fluoro
- pregnene
- acylates
- dihydroxy
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds having the formulae <FORM:0878705/IV (b)/1> <FORM:0878705/IV (b)/2> <FORM:0878705/IV (b)/3> wherein the 1,2-carbon atom linkage is a single or a double bond linkage, R is hydrogen or the acyl group of an organic carboxylic acid, X is the carbonyl radical or the b -hydroxymethylene radical and Z is halogen, and a process which comprises treating 6-fluoro-11b ,21- dihydroxy- 4-pregnene- 3,20-dione (and the 21-acylates thereof) with a dehydration agent to obtain 6-fluro-21-hydroxy-4,9(11)-pregnadiene-3,20-dione (and the 21-acylates thereof), which on treatment with hypohalous acid in which the halogen is bromine chlorine or iodine gives 6-fluoro-9a -halo- 11b ,21- dihydroxy-4- pregnene-3,20-dione (and the 21-acylates thereof), said 9a -halo-compound is treated with a mild base to give 6-fluoro-9b ,11b -oxido-21-hydroxy-4-pregnene-3,20-dione (and the 21-acylates thereof) which on treatment with hydrogen halide, e.g. HF, HCl and HBr gives the corresponding 6-fluoro-9a -halo-11b ,21-dihydroxy-4-pregnene-3,20-dione (and the 21-acylates thereof) which can be oxidised to produce 6-fluro-9a -halo-21-hydroxy-4-pregnene- 3,11,20-trione (and the 21-acylates thereof). The 6-fluoro9a -halo-11-oxygenated-4-pregnene-3,20-diones and their 21-esters may then be dehydrogenated using microorganisms, e.g. Septomyxa, Corynebacterium, Didymella, Calonectria, Alternaria etc. to obtain 6-fluoro-9a -halo-11b ,21-dihydroxy-1,4- pregnadiene-3-20-dione (and the 21-acylates thereof) and 6-fluoro-9a -halo- 1,4-pregnadiene- 3,11,20-trione (and the 21-acylates thereof). The dehydrogenation may also be effected chemically by means of selenium dioxide. Alternatively the D 1,4-pregnadienes are obtained by a similar series of reactions starting with 6-fluoro-11b -hydroxy-1,4-pregnadiene-3,20-dione (and the 21-acylates thereof) which is obtained by dehydrogenating 6-fluoro-11b ,21- dihydroxy-4-pregnene-3,20-dione (and the 21-acylates thereof). The process of the present invention is applicable to both 6a and 6b -fluoro compounds. The 6b compounds are converted to 6a compounds by treatment with hydrogen halide, e.g. gaseous HCl. Alternatively epimerisation of the 6b ,9a -difluoro compounds may be effected with alkali. Specific compounds claimed are 6a ,9a -difluoro- 11b ,21- dihydroxy-4- pregnene- 3,20-dione, 6a ,9a -difluoro- 21-hydroxy-4-pregnene-3,11,20-trione, the corresponding 1,4-pregnadienes and the 21-acetate, 21-hemisuccinates thereof, 6a -fluoro-9a -bromo-11b ,21-dihydroxy-4-pregnene-3,20-dione, the 21-acetate thereof and the corresponding 1,4-pregnadienes, 6a -fluoro-9b ,11b -oxido-21-hydroxy- 4-pregnene-3,20-dione, the 21-acetate thereof and the corresponding 1,4-pregnadienes, 6a -fluoro-21-hydroxy-4,9(11)- pregnadiene-3,20-dione, the 21-acetate thereof and the corresponding 1,4,9(11)-pregnatrienes. Specification 871,764 is referred to.ALSO:Pharmaceutical compositions comprise compounds of the formula <FORM:0878705/VI/1> wherein the 1,2-carbon linkage is a single bond or a double bond linkage, R represents hydrogen or the acyl radical of an organic carboxylic acid, preferably containing 1-12 carbon atoms, inclusive, X is the carbonyl radical or the b 1-hydroxymethylene radical and Z is halogen, and a pharmaceutical diluent. They may be administered orally as pills, tablets, capsules, solutions, syrups and elixirs, in liquid forms for injectable products, and topically as ointments, creams and lotions with or without coacting antibiotics and germicides. Specification 871,764 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US878705XA | 1957-11-29 | 1957-11-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB878705A true GB878705A (en) | 1961-10-04 |
Family
ID=22207734
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB37861/58A Expired GB878705A (en) | 1957-11-29 | 1958-11-25 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB878705A (en) |
-
1958
- 1958-11-25 GB GB37861/58A patent/GB878705A/en not_active Expired
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