GB1012493A - New methyl-oestrenes and process for their manufacture - Google Patents

New methyl-oestrenes and process for their manufacture

Info

Publication number
GB1012493A
GB1012493A GB4349263A GB4349263A GB1012493A GB 1012493 A GB1012493 A GB 1012493A GB 4349263 A GB4349263 A GB 4349263A GB 4349263 A GB4349263 A GB 4349263A GB 1012493 A GB1012493 A GB 1012493A
Authority
GB
United Kingdom
Prior art keywords
compound
oxo
oestrene
hydroxy
group
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
GB4349263A
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.)
BASF Schweiz AG
Original Assignee
Ciba 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
Priority claimed from CH1377562A external-priority patent/CH451930A/en
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB1012493A publication Critical patent/GB1012493A/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
    • A61K31/568—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
    • 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
    • C07J11/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises compounds of the formula <FORM:1012493/C2/1> where R1 represents a free or esterified hydroxyl group and R2 represents a hydrogen atom or a saturated or unsaturated aliphatic hydrocarbon group of up to 7 carbon atoms, or R1 and R2 together represent an oxo group, and a process for the preparation thereof wherein in a compound of the formula <FORM:1012493/C2/2> when R3 represents a thioketal group, the thioketal group is eliminated by a known method and, if desired, a resulting 17a -unsubstituted 17b -hydroxy compound is oxidized to a 17-oxo compound, a 17-oxo compound is reduced by a complex light metal hydride or reacted with a metal derivative of a lower saturated or unsaturated aliphatic hydrocarbon to form a 17b -hydroxy compound, in a resulting compound any unsaturated hydrocarbon radical in the 17a -position is hydrogenated and/or at any stage a resulting 17b -hydroxy compound is converted into an ester or vice-versa. D 4 - 3,3 - Ethylenedithio - 7a - methyl - 17b -acetoxy-oestrene is prepared by reacting ethylene dithiol with D 4 - 3 - oxo - 7a - methyl - 17b -acetoxy-oestrene in the presence of boron trifluoride etherate. D 4 - 3,3 - Ethylenedithio - 7a ,17a - dimethyl-17b -hydroxy-oestrene is prepared by reacting ethylene dithiol with D 4-3-oxo-7a ,17a -dimethyl -17b -hydroxy-oestrene in the presence of boron trifluoride etherate. Therapeutic compositions with anabolic, anti-hypercholesterolenic and ovulation-inhibiting properties, in the form of tablets, dragees, capsules, solutions, suspensions or emulsions for enteral or parenteral application, comprise compounds of the Formula (I) together with a suitable pharmaceutical carrier.
GB4349263A 1962-11-23 1963-11-04 New methyl-oestrenes and process for their manufacture Expired GB1012493A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH1377562A CH451930A (en) 1962-11-23 1962-11-23 Process for the preparation of new methylostrenes
CH172663 1963-02-12
CH695663 1963-06-04
CH792363 1963-06-26

Publications (1)

Publication Number Publication Date
GB1012493A true GB1012493A (en) 1965-12-08

Family

ID=27428267

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4349263A Expired GB1012493A (en) 1962-11-23 1963-11-04 New methyl-oestrenes and process for their manufacture

Country Status (5)

Country Link
AT (1) AT271744B (en)
DE (1) DE1443619A1 (en)
DK (1) DK109866C (en)
GB (1) GB1012493A (en)
SE (1) SE320662B (en)

Also Published As

Publication number Publication date
DE1443619A1 (en) 1969-10-23
SE320662B (en) 1970-02-16
DK109866C (en) 1968-07-22
AT271744B (en) 1969-06-10

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