GB913052A - A new steroid compound and its preparation - Google Patents

A new steroid compound and its preparation

Info

Publication number
GB913052A
GB913052A GB39800/60A GB3980060A GB913052A GB 913052 A GB913052 A GB 913052A GB 39800/60 A GB39800/60 A GB 39800/60A GB 3980060 A GB3980060 A GB 3980060A GB 913052 A GB913052 A GB 913052A
Authority
GB
United Kingdom
Prior art keywords
methyl
dihydroxy
androsta
dien
androst
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
GB39800/60A
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
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB913052A publication Critical patent/GB913052A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • 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)
  • 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 2-methyl-11b ,17b dihydroxy - 17a - ethynyl - androsta-1,4-dien-3-one and processes for the preparation thereof in which 11b -hydroxy-testosterone is reacted with a lower alkyl oxalate in an inert solvent medium in the presence of alkali metal alcoholate so as to effect the introduction of an alkoxy-oxalyl substituent at the 2-position thereof yielding a 2-alkoxy-oxalyl-11b ,17b dihydroxy-androst-4-en-3-one, which is then methylated to yield the corresponding 2#x-methyl - 2#x - alkoxy-oxalyl-11b ,17b -dihydroxy-androst-4-en-3-one, which is then reacted with an alcoholic alkali metal lower alkyl compound to yield 2a -methyl-11b ,17b -dihydroxy-androst-4-en-3-one whose hydroxyl group at the 17-position is esterified so as to form a 2a -methyl - 11b - hydroxy-17b -acyloxy-androst-4-en-3-one, into which a double bond is introduced at the 1-position by reaction with alcoholic selenium dioxide to obtain the corresponding 2-methyl-11b -hydroxy-17b -acyloxy-androsta-1,4-dien-3-one which is then saponified to form 2-methyl-11b ,17b -dihydroxy-androsta-1,4-dien-3-one, oxidation of which yields 2-methyl-11b -hydroxy-androsta-1,4-dien-3,17-dione, and the latter is subjected to ethynylation selectively by reaction with acetylene in an organic solvent at the 17-position so as to yield the desired compound 2 - methyl - 11b ,17b - dihydroxy-17a -ethynyl-androsta - 1,4 - dien-3-one. Alternatively the ethynylation may be effected with a Grignard reagent.
GB39800/60A 1959-11-20 1960-11-18 A new steroid compound and its preparation Expired GB913052A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR810809A FR1359605A (en) 1959-11-20 1959-11-20 2-methylated cyclopentanophenanthrenic derivatives and process for their preparation

Publications (1)

Publication Number Publication Date
GB913052A true GB913052A (en) 1962-12-19

Family

ID=8721585

Family Applications (1)

Application Number Title Priority Date Filing Date
GB39800/60A Expired GB913052A (en) 1959-11-20 1960-11-18 A new steroid compound and its preparation

Country Status (5)

Country Link
BE (1) BE597232A (en)
CH (1) CH406201A (en)
ES (1) ES262354A1 (en)
FR (2) FR1359605A (en)
GB (1) GB913052A (en)

Also Published As

Publication number Publication date
ES262354A1 (en) 1961-01-16
FR36M (en) 1960-11-28
BE597232A (en) 1961-05-18
FR1359605A (en) 1964-04-30
CH406201A (en) 1966-01-31

Similar Documents

Publication Publication Date Title
GB913052A (en) A new steroid compound and its preparation
GB959798A (en) Angular carboxylic acid derivatives and their preparation
GB967080A (en) Novel steroid compounds and process for the preparation thereof
US2779774A (en) 3beta-oxy-delta16-allopregnenedione-11, 20 and process
GB996079A (en) 17ª‡,21-substituted methylenedioxy steroids and methods therefor
GB1176229A (en) Preparation of Ethynyl Hydroxy Steroids
ES361100A1 (en) 01beta-METHYL-19-NORPREGNENE COMPOUNDS
GB843517A (en) Improvements in or relating to steroid compounds
GB933277A (en) New steroid compounds and processes for their preparation
GB908284A (en) Steroid alkyl ethers and a process for their manufacture
GB952492A (en) New steroid compounds and processes for their preparation
GB966100A (en) Novel cyclopentanophenanthrene compounds and a process for the production thereof
GB934708A (en) New steroid compounds and their production
GB934801A (en) Steroid compounds
GB904067A (en) Steroids
GB957221A (en) Novel steroid compounds and processes for their preparation
GB745636A (en) Cyclopentanophenanthrene derivatives and process for their manufacture
ES264737A1 (en) New steroid compounds, and processes for the preparation thereof
GB948207A (en) Process for the preparation of unsaturated keto-steroids
GB1003471A (en) Novel steroids and methods for their production
GB936894A (en) Novel steroid compounds and processes for the preparation thereof
GB884412A (en) New 6-methyl-19-nor-steroids and process for the preparation thereof
GB991475A (en) Novel steroid compounds and processes for their production
GB1024912A (en) 9,11-ethylenic steroids having an aromatic ring a
GB956271A (en) Improvements in or relating to the preparation of steroid compounds