GB1196476A - 21-Fluoro-Delta<4,6>-Pregnadienes and process for their manufacture - Google Patents

21-Fluoro-Delta<4,6>-Pregnadienes and process for their manufacture

Info

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
Application number
GB3531267A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Pharma AG
Original Assignee
Schering AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Schering AG filed Critical Schering AG
Publication of GB1196476A publication Critical patent/GB1196476A/en
Expired legal-status Critical Current

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.
GB3531267A 1966-08-11 1967-08-01 21-Fluoro-Delta<4,6>-Pregnadienes and process for their manufacture Expired GB1196476A (en)

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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19908762A1 (en) * 1999-02-18 2000-08-31 Jenapharm Gmbh Use of dienogest in high doses

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