GB874779A - New steroid compounds and processes for their preparation - Google Patents
New steroid compounds and processes for their preparationInfo
- Publication number
- GB874779A GB874779A GB42918/59A GB4291859A GB874779A GB 874779 A GB874779 A GB 874779A GB 42918/59 A GB42918/59 A GB 42918/59A GB 4291859 A GB4291859 A GB 4291859A GB 874779 A GB874779 A GB 874779A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dione
- dihydroxy
- preparation
- ketone group
- dehydrobromination
- 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 compounds of the general formula <FORM:0874779/IV (b)/1> (wherein X represents hydrogen or bromine and Ac an acyl radical, e.g. acetyl, benzoyl, hexahydrobenzoyl, m-sulphobenzoyl or b -cyclopentylpropionyl), and the preparation thereof by protecting the 20-ketone group of 3a ,17a -dihydroxy-16a -methylpregnane-11, 20-dione (e.g. by conversion to the 20-semicarbazone), reducing the 11-ketone group and liberating the 20-ketone group to form 3a ,11a , 17a -trihydroxy-16a -methylpregnan -20- one, dehydrating this to yield 3a ,17a -dihydroxy-16a -methylpregn-9(11 -en-20-one, introducing a halogen substitutent at the 21-position and reacting the product with the appropriate acylating agent to yield a 3a ,17a -dihydroxy-16a -methyl-21-acyloxypregn-9(11)-en -20- one, oxidising this to the 3,20-dione and monoor di-brominating this product. The dehydration step may be preceded by acylation of the 3a -hydroxy group and followed by saponification. 9a -Fluoro-11b ,17a ,21-trihydroxy-16a -methylpregna-1,4-diene-3, 20-dione can be prepared from the compounds of the general formula above by subjecting them to dehydrobromination and dehydrogenation when X=H, or to di-dehydrobromination when X=Br, followed in either case by introduction of an 11b -hydroxy group and a 9a -fluorine atom.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR874779X | 1959-01-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB874779A true GB874779A (en) | 1961-08-10 |
Family
ID=9359842
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB42918/59A Expired GB874779A (en) | 1959-01-05 | 1959-12-17 | New steroid compounds and processes for their preparation |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB874779A (en) |
-
1959
- 1959-12-17 GB GB42918/59A patent/GB874779A/en not_active Expired
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