GB1003304A - A process for the preparation of novel steroid compounds - Google Patents

A process for the preparation of novel steroid compounds

Info

Publication number
GB1003304A
GB1003304A GB1808862A GB1808862A GB1003304A GB 1003304 A GB1003304 A GB 1003304A GB 1808862 A GB1808862 A GB 1808862A GB 1808862 A GB1808862 A GB 1808862A GB 1003304 A GB1003304 A GB 1003304A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
group
introduce
product
ethynyl
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
GB1808862A
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 FR861446A external-priority patent/FR1376454A/en
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB1003304A publication Critical patent/GB1003304A/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
    • A61K31/568—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 positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
    • A61K31/569—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 positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone substituted in position 17 alpha, e.g. ethisterone
    • 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
    • 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
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 17a -ethynyl-17b -hydroxy - 13b - n - propyl - gon - 4 - en - 3-one, 3-cyclic ketals thereof, pharmaceutical compositions thereof and a process in which a 17b - acyloxy or 17b - hydroxy - 13b - alkylgon-4-en-3-one is subjected to ketalisation to introduce a 3-cyclic ketal group of the general formula <FORM:1003304/C2/1> (in which R and R1, which may be the same or different, each represents a hydrogen atom or an alkyl group having from 1-8 carbon atoms and n is either 0 or 1), a 17b -acyloxy product is saponified at the 17-position, the 17b -hydroxy product is oxidized selectively to introduce a 17-Keto group, the 17-Keto product is reacted with an ethylynation agent to introduce a 17a -ethynyl - 17b - hydroxy group and the 3-cyclic Ketal group is subjected to deketalization. The Ketalization may be effected by a glycol or a dioxolan, oxidation by cyclohexanone in the presence of aluminium isopropylate, and alkynylation with alkali metal acetylides or a Grignard reagent. Said compositions having progestomitic activity are administered orally in tablets sublingual tablets, syrups or elixirs, by injection in sterile liquid medium or rectally as a suppository. Specifications 979,892 and 1,003,305 are referred to.
GB1808862A 1961-05-10 1962-05-10 A process for the preparation of novel steroid compounds Expired GB1003304A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR861446A FR1376454A (en) 1961-05-10 1961-05-10 19-nor testosterone derivative and method of preparation
FR870347A FR1456M (en) 1961-05-10 1961-08-08 New drug in particular for the treatment of deficiencies of the corpus luteum.

Publications (1)

Publication Number Publication Date
GB1003304A true GB1003304A (en) 1965-09-02

Family

ID=26190476

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1808862A Expired GB1003304A (en) 1961-05-10 1962-05-10 A process for the preparation of novel steroid compounds

Country Status (5)

Country Link
BE (1) BE617484A (en)
CH (1) CH411854A (en)
DE (1) DE1290139B (en)
ES (1) ES277176A1 (en)
GB (1) GB1003304A (en)

Also Published As

Publication number Publication date
BE617484A (en) 1962-11-12
ES277176A1 (en) 1962-08-01
CH411854A (en) 1966-04-30
DE1290139B (en) 1969-03-06

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