GB1196476A - 21-Fluoro-Delta<4,6>-Pregnadienes and process for their manufacture - Google Patents
21-Fluoro-Delta<4,6>-Pregnadienes and process for their manufactureInfo
- Publication number
- GB1196476A GB1196476A GB3531267A GB3531267A GB1196476A GB 1196476 A GB1196476 A GB 1196476A GB 3531267 A GB3531267 A GB 3531267A GB 3531267 A GB3531267 A GB 3531267A GB 1196476 A GB1196476 A GB 1196476A
- Authority
- GB
- United Kingdom
- Prior art keywords
- converting
- methylene
- fluoro
- compound
- acid
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Abstract
1,196,476. 1,2 - Methylene - 21 - fluoro - #<SP>4</SP>'<SP>6-</SP> pregnadienes. SCHERING A.G. 1 Aug., 1967 [11 Aug., 1966; 13 May, 1967], No. 35312/67. Heading C2U. Novel steroids of the formula (in which X is F or Cl and R is organic or inorganic acyl) are prepared (1) by esterification of the free 17α-ols, or (2) by treatment of the corresponding 6,7-epoxides with an acid HX and elimination of water from the resulting compounds by means of a strong acid and, if the 1α,2α-methylene ring has been opened, reformation of this by means of an organic base or of aluminium oxide. In (2) acid treatment and water elimination can be effected in one step with hydrochloric acid in acetic acid. The novel 6-chloro-21-fluoro-1α,2α-methylene- #<SP>4,6</SP> - pregnadien - 17α - ol - 3,20 - dione is prepared by converting the corresponding 21- unsubstituted steroid to the 21-iodo compound and converting this to the required product via the 21-acetoxy compound, the free 21-ol and the 21-mesyloxy compound. The 6,7-epoxy starting materials are prepared by converting 1α,2α-methylene-#<SP>4,6</SP>-pregnadiene-17α-ol-3,20-dione to the 21-fluoro compound via the 21-iodo, 21-acetoxy, 21-hydroxy and 21- mesyloxy compounds, esterifying to give the 17- acylates and converting to the required epoxides directly or via the 7α-bromo-6#-ols. The steroids of the invention, which are stated to possess strong gestagenic activity without anti-androgenic activity, may be made up into pharmaceutical compositions with suitable carriers.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DESC039385 | 1966-08-11 | ||
DESC040710 | 1967-05-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1196476A true GB1196476A (en) | 1970-06-24 |
Family
ID=25993399
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3531267A Expired GB1196476A (en) | 1966-08-11 | 1967-08-01 | 21-Fluoro-Delta<4,6>-Pregnadienes and process for their manufacture |
Country Status (12)
Country | Link |
---|---|
BE (1) | BE702583A (en) |
CH (1) | CH515227A (en) |
DE (2) | DE1593515C3 (en) |
DK (1) | DK117227B (en) |
ES (1) | ES343859A1 (en) |
FI (1) | FI45172C (en) |
FR (1) | FR1561096A (en) |
GB (1) | GB1196476A (en) |
IL (1) | IL28465A (en) |
NL (1) | NL152267B (en) |
NO (1) | NO126525B (en) |
SE (1) | SE320067B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19908762A1 (en) * | 1999-02-18 | 2000-08-31 | Jenapharm Gmbh | Use of dienogest in high doses |
-
1966
- 1966-08-11 DE DE19661593515 patent/DE1593515C3/en not_active Expired
-
1967
- 1967-05-13 DE DE19671643021 patent/DE1643021A1/en active Pending
- 1967-06-28 SE SE9525/67*A patent/SE320067B/xx unknown
- 1967-07-11 FI FI191467A patent/FI45172C/en active
- 1967-08-01 GB GB3531267A patent/GB1196476A/en not_active Expired
- 1967-08-02 DK DK394967A patent/DK117227B/en unknown
- 1967-08-04 CH CH1100967A patent/CH515227A/en not_active IP Right Cessation
- 1967-08-05 ES ES343859A patent/ES343859A1/en not_active Expired
- 1967-08-07 IL IL2846567A patent/IL28465A/en unknown
- 1967-08-10 FR FR1561096D patent/FR1561096A/fr not_active Expired
- 1967-08-10 NO NO16932167A patent/NO126525B/no unknown
- 1967-08-10 NL NL6711020A patent/NL152267B/en unknown
- 1967-08-11 BE BE702583D patent/BE702583A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
ES343859A1 (en) | 1968-10-01 |
DE1593515C3 (en) | 1975-08-14 |
FR1561096A (en) | 1969-03-28 |
DE1593515B2 (en) | 1975-01-09 |
BE702583A (en) | 1968-02-12 |
FI45172B (en) | 1971-12-31 |
SE320067B (en) | 1970-02-02 |
DK117227B (en) | 1970-03-31 |
CH515227A (en) | 1971-11-15 |
FI45172C (en) | 1972-04-10 |
NL152267B (en) | 1977-02-15 |
IL28465A (en) | 1972-01-27 |
DE1643021A1 (en) | 1971-03-11 |
NO126525B (en) | 1973-02-19 |
DE1593515A1 (en) | 1970-08-13 |
NL6711020A (en) | 1968-02-12 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |