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GB1070329A - Improvements in or relating to 6,6-ethylenetestosterones - Google Patents

Improvements in or relating to 6,6-ethylenetestosterones

Info

Publication number
GB1070329A
GB1070329A GB17967/65A GB1796765A GB1070329A GB 1070329 A GB1070329 A GB 1070329A GB 17967/65 A GB17967/65 A GB 17967/65A GB 1796765 A GB1796765 A GB 1796765A GB 1070329 A GB1070329 A GB 1070329A
Authority
GB
United Kingdom
Prior art keywords
group
compound
vinyl
treating
hydrogen atom
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
GB17967/65A
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.)
Tufts University
Original Assignee
Tufts University
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 Tufts University filed Critical Tufts University
Publication of GB1070329A publication Critical patent/GB1070329A/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
    • C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
    • 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)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of formula <FORM:1070329/C2/1> wherein Y is a single or double bond, R is a hydrogen atom, a C2- 10 acyl group or a cyclopent-1-enyl group, and R1 is a hydrogen atom or a methyl, ethyl, vinyl, ethynyl chloroethynyl, bromoethynyl, 2-propynyl or 1,1,1-trifluoro-2-propynyl group, and their preparation by formation of a testosterone methyl enol ether of formula <FORM:1070329/C2/2> wherein Ac is an acetyl group, treating this with phosgene and dimethylformamide to give the corresponding 6-formyl compound, reducing this to the corresponding 6-hydroxymethyl compound, dehydrating this to the corresponding 6-methylene compound, and treating this with dimethylsulphoxonium methylide, CH3S(=CH2)=O, prepared by reaction of trimethylsulphoxonium iodide with a strong base, followed, if desired, by (a) hydrolysis of the 17-acetoxy group, (b) 17-acylation, (c) 17-etherification by reaction with a mixture of the diethyl acetal and enolic ether of cyclopentanone, (d) 1-dehydrogenation using dichlorodicyanoquinone, and (e) hydrogenation of a 17a -ethynyl group to form a 17a -vinyl or 17a -ethyl group. The compounds of the invention have anabolic and androgenic activity and may be used in pharmaceutical compositions in combination with a carrier.
GB17967/65A 1964-05-11 1965-04-28 Improvements in or relating to 6,6-ethylenetestosterones Expired GB1070329A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US36660464A 1964-05-11 1964-05-11

Publications (1)

Publication Number Publication Date
GB1070329A true GB1070329A (en) 1967-06-01

Family

ID=23443705

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17967/65A Expired GB1070329A (en) 1964-05-11 1965-04-28 Improvements in or relating to 6,6-ethylenetestosterones

Country Status (9)

Country Link
BE (1) BE663708A (en)
CH (1) CH435263A (en)
DE (1) DE1493258A1 (en)
DK (1) DK117349B (en)
FR (2) FR4753M (en)
GB (1) GB1070329A (en)
IL (1) IL23451A (en)
NL (1) NL6505879A (en)
SE (1) SE310176B (en)

Also Published As

Publication number Publication date
NL6505879A (en) 1965-11-12
BE663708A (en) 1965-11-10
CH435263A (en) 1967-05-15
FR4753M (en) 1967-01-16
IL23451A (en) 1969-01-29
DE1493258A1 (en) 1969-11-20
DK117349B (en) 1970-04-20
FR1455109A (en) 1966-04-01
SE310176B (en) 1969-04-21

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