GB1074493A - Novel estrane derivatives and processes for preparing them - Google Patents

Novel estrane derivatives and processes for preparing them

Info

Publication number
GB1074493A
GB1074493A GB2461664A GB2461664A GB1074493A GB 1074493 A GB1074493 A GB 1074493A GB 2461664 A GB2461664 A GB 2461664A GB 2461664 A GB2461664 A GB 2461664A GB 1074493 A GB1074493 A GB 1074493A
Authority
GB
United Kingdom
Prior art keywords
estra
triene
ethynyl
dihydroxy
compounds
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
GB2461664A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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
Priority claimed from FR937897A external-priority patent/FR3187M/en
Priority claimed from FR941004A external-priority patent/FR1375078A/en
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB1074493A publication Critical patent/GB1074493A/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
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/567—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in position 17 alpha, e.g. mestranol, norethandrolone
    • 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
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • 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
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/566—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol having an oxo group in position 17, e.g. estrone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Abstract

The invention comprises 11b ,17b -dihydroxy-estra-1,3,5(10) -triene derivatives of the formula <FORM:1074493/C2/1> wherein R represents a hydrogen atom, an acyl group being the residue of a carboxylic organic acid, or an alkyl radical and a process for the preparation thereof in which 3,11b -dihydroxy-estra-1,3,5(10) -triene-17-one is subjected to the action of an ethynylating agent, e.g. ethynyl magnesium chloride or potassium acetylide, so as to form 17a -ethynyl-3,11b ,17b -trihydroxy-estra-1,3,5(10) - triene. Alternatively 11b ,17b - dihydroxy - 17a - ethynyl - androsta - 1,4 - dien - 3-one is submitted to heating at a temperature above 450 DEG C. so as to form 3,11b ,17b -tri-hydroxy - 17a - ethynyl - estra - 1,3,5(10) - triene. The 3-hydroxy compounds so obtained may be alkylated or acylated to form the corresponding 3-alkoxy or 3-acyloxy compounds. Pharmaceutical compositions having estrogenic activity and containing the above compounds are administered orally as tablets, pills, sublingual tablets, capsules, cachets, powders, syrups, and elixirs, by injection in solution or suspension or rectally as a suppository.
GB2461664A 1963-06-12 1964-06-12 Novel estrane derivatives and processes for preparing them Expired GB1074493A (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
FR937897A FR3187M (en) 1963-06-12 1963-06-12 New drug in particular for the treatment of irregularities and ovarian insufficiencies.
FR941004A FR1375078A (en) 1963-07-10 1963-07-10 Process for introducing an oxygen function in position 11 of certain 19-norsteroids and resulting products
FR941005A FR1453216A (en) 1963-06-12 1963-07-10 New estradiol derivatives and method of preparation
FR951379A FR1468639A (en) 1963-07-10 1963-10-22 Novel 11-oxygenated diene steroid and method of preparation
FR960726A FR5089M (en) 1963-07-10 1964-01-17
FR971005A FR3845M (en) 1963-07-10 1964-04-15 New drug in particular for the treatment of hypercholesterolemia and the resulting disorders.

Publications (1)

Publication Number Publication Date
GB1074493A true GB1074493A (en) 1967-07-05

Family

ID=27546226

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2461664A Expired GB1074493A (en) 1963-06-12 1964-06-12 Novel estrane derivatives and processes for preparing them

Country Status (1)

Country Link
GB (1) GB1074493A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4859370A (en) * 1985-06-25 1989-08-22 Sri International 9 alpha, 11 beta-substituted and 11 beta-substituted estranes
US5554603A (en) * 1993-09-17 1996-09-10 The United States Of America As Represented By The Department Of Health And Human Services Orally active derivatives of 1,3,5(10)-estratriene

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4859370A (en) * 1985-06-25 1989-08-22 Sri International 9 alpha, 11 beta-substituted and 11 beta-substituted estranes
US5554603A (en) * 1993-09-17 1996-09-10 The United States Of America As Represented By The Department Of Health And Human Services Orally active derivatives of 1,3,5(10)-estratriene

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