GB977082A - 1ª‡-methyl-steroids and a process for their manufacture - Google Patents

1ª‡-methyl-steroids and a process for their manufacture

Info

Publication number
GB977082A
GB977082A GB9933/61A GB993361A GB977082A GB 977082 A GB977082 A GB 977082A GB 9933/61 A GB9933/61 A GB 9933/61A GB 993361 A GB993361 A GB 993361A GB 977082 A GB977082 A GB 977082A
Authority
GB
United Kingdom
Prior art keywords
steroids
methyl
keto
saturated
reacting
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
GB9933/61A
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
Priority claimed from DESCH27696A external-priority patent/DE1122944B/en
Priority claimed from DESCH28196A external-priority patent/DE1131667B/en
Priority claimed from DESCH28955A external-priority patent/DE1152100B/en
Application filed by Schering AG filed Critical Schering AG
Publication of GB977082A publication Critical patent/GB977082A/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
    • 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
    • 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
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • 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
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material 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 1a -methyl-3-ketosteroids of the general formula <FORM:0977082/C1/1> wherein X is a saturated or unsaturated bond between the carbon atoms 4 and 5, Y is a bond between carbon atoms 6 and 7 which is saturated when X is saturated and when X is unsaturated Y is either saturated or unsaturated and R is <FORM:0977082/C1/2> or <FORM:0977082/C1/3> and a process for the preparation of 1a -methyl-3-keto-steroids by reacting 1a -halomethyl-3-ketosteroids with a dehalogenating agent of reducing action such as Raney nickel, by reacting 1, 2a -methylene -3- keto-steroids with catalytically activated hydrogen such as hydrogen in the presence of a platinum catalyst and glacial acetic acid and oxidising the resulting 3-hydroxy-1a -methyl-steroids, and by reacting D 1-3-keto-steroids with a methyl magnesium halide in the presence of cuprous chloride. All the above processes may be modified in that 1a -methyl-D 4,6-3 -keto-steroids obtained may be selectively hydrogenated to 1a -methyl -D 4-3-keto-steroids, for example with hydrogen in the presence of palladium-carbonate catalyst, products containing a 17-ester group may be hydrolysed to the corresponding 17-hydroxy compounds, and products containing a hydroxy group may be esterified or etherified. Specification 977,083 is referred to.
GB9933/61A 1960-04-06 1961-03-17 1ª‡-methyl-steroids and a process for their manufacture Expired GB977082A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DESCH27696A DE1122944B (en) 1960-04-06 1960-04-06 Process for the preparation of 1ª ‡ -Methyl-3-ketosteroids
DESCH28196A DE1131667B (en) 1960-07-21 1960-07-21 Process for the production of 1ª ‡ -methyl steroids of the androstane series
DESCH28955A DE1152100B (en) 1960-12-23 1960-12-23 Process for the preparation of 1ª ‡ -Methyl-3-ketosteroids

Publications (1)

Publication Number Publication Date
GB977082A true GB977082A (en) 1964-12-02

Family

ID=27212273

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9933/61A Expired GB977082A (en) 1960-04-06 1961-03-17 1ª‡-methyl-steroids and a process for their manufacture

Country Status (3)

Country Link
CH (1) CH408911A (en)
FR (1) FR1293M (en)
GB (1) GB977082A (en)

Also Published As

Publication number Publication date
CH408911A (en) 1966-03-15
FR1293M (en) 1962-05-07

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