GB885092A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB885092A GB885092A GB13211/59A GB1321159A GB885092A GB 885092 A GB885092 A GB 885092A GB 13211/59 A GB13211/59 A GB 13211/59A GB 1321159 A GB1321159 A GB 1321159A GB 885092 A GB885092 A GB 885092A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dione
- fluoro
- treating
- compounds
- diacylates
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 hydrocarbon carboxylic acid Chemical class 0.000 abstract 2
- DJGMDJDFMCMJBU-OBQKJFGGSA-N (8r,9s,10r,13s,14s,17r)-17-(2-fluoroacetyl)-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CF)[C@@H]4[C@@H]3CCC2=C1 DJGMDJDFMCMJBU-OBQKJFGGSA-N 0.000 abstract 1
- QQCBOIWDENXRLP-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCC=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 QQCBOIWDENXRLP-BYZMTCBYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 229940096017 silver fluoride Drugs 0.000 abstract 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
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 having the formulae <FORM:0885092/IV (b)/1> <FORM:0885092/IV (b)/2> wherein R is hydrogen or Ac and Ac is the acyl radical of a hydrocarbon carboxylic acid containing 1-12 carbon atoms, the corresponding 9(11)-dehydro compounds and processes for the preparation thereof by treating a 17a ,21-dihydroxy-4-pregnene-3,20-dione (I) or the corresponding 1,4-pregnadiene with an organic sulphonyl halide to form a 21-sulphonic acid ester (II), treating (II) with an alkali metal iodide to form a 21-iodo compound (III), and treating (III) with silver fluoride to obtain 21-fluoro-17a -hydroxy-4-pregnene-3,20-dione or 21-fluro-17a -hydroxy-1,4-pregnadiene-3,20-dione. These compounds may be esterified to produce the 17a -acylates, or 3,17a -diacylates.ALSO:Pharmaceutical compositions comprise 21-fluoro - 17a - hydroxyprogesterone, 9 (11)-21-fluoro - 17a - hydroxyprogesterone, 17a -acylates thereof or 3,17a -diacylates thereof, and a pharmaceutical diluent. They are employed orally as pills, tablets, capsules, solutions, syrups and elixirs, or in liquid forms for injection.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US885092XA | 1958-05-15 | 1958-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB885092A true GB885092A (en) | 1961-12-20 |
Family
ID=22211783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13211/59A Expired GB885092A (en) | 1958-05-15 | 1959-04-17 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB885092A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4377575A (en) | 1978-04-25 | 1983-03-22 | Hoechst Aktiengesellschaft | Corticoid-17-(alkyl carbonates) and process for their manufacture |
-
1959
- 1959-04-17 GB GB13211/59A patent/GB885092A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4377575A (en) | 1978-04-25 | 1983-03-22 | Hoechst Aktiengesellschaft | Corticoid-17-(alkyl carbonates) and process for their manufacture |
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