GB965658A - Cyclopentanophenanthrene derivatives - Google Patents
Cyclopentanophenanthrene derivativesInfo
- Publication number
- GB965658A GB965658A GB3020860A GB3020860A GB965658A GB 965658 A GB965658 A GB 965658A GB 3020860 A GB3020860 A GB 3020860A GB 3020860 A GB3020860 A GB 3020860A GB 965658 A GB965658 A GB 965658A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fluoro
- acetate
- dione
- water
- reacting
- 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
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- 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 16, 21-diacetate of 6a -fluoro-D 4-pregnene-16a , 17a , 21-triol-3, 20-dione is prepared by reacting the 21-acetate of 6b -fluoro-5a -bromo-16a , 17a -oxido-pregnan-21-ol-3, 20-dione with (a) hydrogen bromide or hydrogen chloride in the presence of acetic acid at a temperature between -5 DEG C. and +15 DEG C., or (b) with sodium acetate in acetone and then reacting the resultant 21-acetate of 6b -fluoro-16a , 17a -oxido-D 4-pregnen-21-ol-3, 20-dione with hydrogen chloride in the presence of acetic acid to yield in each case the 21-acetate of a 6a -fluoro-16b -halo-D 4-pregnene-17a , 21-diol-3, 20-dione, acetylating the 17a -hydroxy group with acetic anhydride and reacting the resultant diacetate with a reagent selected from potassium acetate in acetic acid, dimethylformamide and water, dimethylacetamide and water, dimethylformamide, water and pyridine, and dimethylacetamide, water and pyridine. The process is illustrated by detailed examples. The product of the invention may be saponified and the free triol oxygenated at C11, e.g. with Cunninghamella Blakesleena spp. to give 6a -fluoro-16a -hydroxy hydrocortisone which may then be modified by standard procedures to yield the cortisone, prednisone and prednisolone analogues, and the corresponding 9a -halo derivatives. Specification 957,891 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MX5580159 | 1959-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB965658A true GB965658A (en) | 1964-08-06 |
Family
ID=19742888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3020860A Expired GB965658A (en) | 1959-09-07 | 1960-09-01 | Cyclopentanophenanthrene derivatives |
Country Status (2)
| Country | Link |
|---|---|
| CH (2) | CH432511A (en) |
| GB (1) | GB965658A (en) |
-
1960
- 1960-09-01 GB GB3020860A patent/GB965658A/en not_active Expired
- 1960-09-05 CH CH1002060A patent/CH432511A/en unknown
- 1960-09-05 CH CH1059866A patent/CH466275A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH466275A (en) | 1968-12-15 |
| CH432511A (en) | 1967-03-31 |
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