GB881334A - Steroid compounds, preparation thereof and compositions thereof - Google Patents
Steroid compounds, preparation thereof and compositions thereofInfo
- Publication number
- GB881334A GB881334A GB40360/59A GB4036059A GB881334A GB 881334 A GB881334 A GB 881334A GB 40360/59 A GB40360/59 A GB 40360/59A GB 4036059 A GB4036059 A GB 4036059A GB 881334 A GB881334 A GB 881334A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- fluoro
- compound
- acetate
- pregnene
- 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
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises compounds having the formula <FORM:0881334/IV (b)/1> and the D 1,4 analogues thereof, wherein X is hydrogen, halogen, methoxyl or ethoxyl; B is acarbonyl or b -hydroxymethylene radical; R is hydrogen or an acyl radical of a hydrocarbon carboxylic acid containing 1-8 carbon atoms, inclusive, and the 6-fluoro is a 6a - or 6b -epimer, and processes for the preparation thereof by subjecting a 16-methylated sapogenin e.g. 16-methyl diosgenin to degradation to obtain 16b - methyl - D 5,16 - pregnadiene - 3 - ol - 20 - one-3-acetate II, reducing II to obtain the corresponding 16b -methyl-D 5-pregnene derivative III which on enol acetylation yields the corresponding 16b -methyl-D 5,17(20)-pregnadiene-3,20-diacetate diacetate IV; treating IV with H2O2 or an organic peracid to obtain the corresponding 5a ,6a -17a ,20a -dioxido derivative V which upon alkaline hydrolysis gives 5a ,6a -oxido-16b -methyl-allopregnane-3b ,17a -diol-20-one VI; converting VI by means of bromine, potassium acetate and potassium iodide into 5a ,6a -oxido-16b -methyl-allo-pregnane-3b , 17a ,21-triol-20-one 21-acetate VII; treating VII with HF to obtain 6b -fluoro-16b -methyl-allo-pregnane-3b ,5a ,17a ,21-tetrol-20-one 21-acetate VIII; oxidising VIII to obtain the 3-keto compound IX, which on dehydration gives the 6b -fluoro-16b -methyl-D 4-pregnene-17a , 21-diol-3,20-dione-21-acetate X; epimerising X to obtain the 6a -fluoro compound XI; hydroxylating to obtain an 11-hydroxy compound XII followed by dehydration to obtain 6 - fluoro - 16b - methyl - D 4,9(11) - pregnadiene - 17a ,21-diol-3,20-dione-21-acetate XIII; treating XIII with a hypohalogenating agent to obtain the corresponding 9a -halo compound XIV, which with potassium acetate gives 6-fluoro-9b ,11b -oxido-16b -methyl compound; treating the 9b ,11b -oxido compound with hydrogen halide or an alcohol gives the 9a -halo or 9a -alkoxy compounds respectively. Treatment with selenium dioxide gives the analogous D 1,4-compounds. Oxidation of the 11b -hydroxy compounds gives the corresponding 11-keto compounds. Illustrative products of the invention are 6a -fluoro-16b -methyl - D 4 - pregnene - 17a ,21 - diol - 3,11,20 - trione, 6a ,9a - difluoro - 16b - methyl - D 4 - pregnene - 17a ,21 - diol - 3,11,20 - trione, 6a -fluoro - 16b - methyl - D 4 - pregnene - 11b ,17a ,21 - triol - 3,20 - dione, 6a ,9a - difluoro - 16b - methyl - D 4 - pregnene - 11b ,17a ,21 - triol - 3,20 - dione, the 21-acetates thereof and the corresponding D 1,4 compounds. Specifications 769,998 and 770,000 are referred to.ALSO:A pharmaceutical composition comprises a compound of the formula <FORM:0881334/VI/1> or the D 1,4 analogues thereof, wherein X is hydrogen, halogen, methoxyl or ethoxyl; B is a carbonyl or b -hydroxymethylene radical; R is hydrogen or an acyl radical of a hydrocarbon carboxylic acid containing 1-8 carbon atoms inclusive; and the 6-fluoro atom is the 6a - or 6b -epimer. Such compositions may be employed orally as pills, tablets, capsules, solutions, syrups and elixirs, in liquid forms for injectable products, or topically as ointments or creams. Specifications 769,998 and 770,000 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US881334XA | 1958-12-05 | 1958-12-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB881334A true GB881334A (en) | 1961-11-01 |
Family
ID=22209545
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB40360/59A Expired GB881334A (en) | 1958-12-05 | 1959-11-27 | Steroid compounds, preparation thereof and compositions thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB881334A (en) |
-
1959
- 1959-11-27 GB GB40360/59A patent/GB881334A/en not_active Expired
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