GB816909A - Improvements in or relating to steroids - Google Patents
Improvements in or relating to steroidsInfo
- Publication number
- GB816909A GB816909A GB10914/56A GB1091456A GB816909A GB 816909 A GB816909 A GB 816909A GB 10914/56 A GB10914/56 A GB 10914/56A GB 1091456 A GB1091456 A GB 1091456A GB 816909 A GB816909 A GB 816909A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- compound
- pregnane
- trione
- 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)
- Steroid Compounds (AREA)
Abstract
The invention comprises laevo rotatory cyclopentanophenanthrene compounds of the general formula <FORM:0816909/IV (b)/1> wherein R1 and R2 represent hydrogen or acyl radicals, R1 and R2 being the same or different, and the preparation thereof by dibrominating in the presence of dioxane a compound of the general formula <FORM:0816909/IV (b)/2> wherein R1 and R2 have the above significance, and by monobrominating in the presence of dioxane a compound of the general formula <FORM:0816909/IV (b)/3> wherein R1 and R2 have the above significance. The latter process may be modified in that the mono-bromo reactant is obtained from a compound of the general formula <FORM:0816909/IV (b)/4> wherein R1 and R2 have the above significance, by the process described and claimed in Specification 760,362. The invention further consists in a process for the preparation of a compound having the general formula <FORM:0816909/IV (b)/5> wherein R1 and R2 have the above significance, by didehydrobrominating a dibromo compound of the general formula above, e.g. by the action of an organic tertiary base such as a collidine, or by means of 2,4-dinitrophenylhydrazine, a 2,4-dinitrophenylhydrazone being formed as an intermediate compound. Preferably R1 and R2 represent acetyl radicals, or R1 represents hydrogen and R2 represents an acetyl radical. The dibromination step is preferably carried out with bromine or N-bromo-succinamide in acetic acid and in the presence of hydrobromic acid in acetic acid, and the monobromination step is preferably carried out with bromine dissolved in acetic acid. The dibromo compound of the above general formula may be precipitated from the reaction mixture by the addition of water, and the precipitate is purified by recrystallization from aqueous acetone. In the examples laevo rotatory 2,4-dibromo-17a -hydroxy-21-acetoxy - pregnane - 3,11,20 - trione is prepared from 4 - bromo - 17a - hydroxy - 21 - acetoxy - pregnane-3,11,20-trione and from 17a -hydroxy - 21 - acetoxy - pregnane - 3,11,20 - trione (the 4-bromo-17a -hydroxy-21-acetoxypregnane-3,11,20-trione is obtained by heating 3a ,17a - dihydroxy - 21 - acetoxy - pregnane - 11,20-dione with acetic acid, dioxane, N-bromosuccimide and water), and 1-dehydrocortisone acetate is prepared from laevo-rotatory 2,4-dibromo - 17a - hydroxy - 21 - acetoxy - pregnane - 3,11,20-trione.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR816909X | 1955-04-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB816909A true GB816909A (en) | 1959-07-22 |
Family
ID=9268054
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB10914/56A Expired GB816909A (en) | 1955-04-15 | 1956-04-10 | Improvements in or relating to steroids |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB816909A (en) |
-
1956
- 1956-04-10 GB GB10914/56A patent/GB816909A/en not_active Expired
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