GB1191768A - 4-Oxo-19-Nor-A-Homo-Steroid Dienes and a Process for their Manufacture - Google Patents

4-Oxo-19-Nor-A-Homo-Steroid Dienes and a Process for their Manufacture

Info

Publication number
GB1191768A
GB1191768A GB5707368A GB5707368A GB1191768A GB 1191768 A GB1191768 A GB 1191768A GB 5707368 A GB5707368 A GB 5707368A GB 5707368 A GB5707368 A GB 5707368A GB 1191768 A GB1191768 A GB 1191768A
Authority
GB
United Kingdom
Prior art keywords
oxo
prepared
homo
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
GB5707368A
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 CH1686167A external-priority patent/CH505808A/en
Priority claimed from CH940568A external-priority patent/CH527809A/en
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB1191768A publication Critical patent/GB1191768A/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
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • 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
    • A—HUMAN NECESSITIES
    • A63—SPORTS; GAMES; AMUSEMENTS
    • A63F—CARD, BOARD, OR ROULETTE GAMES; INDOOR GAMES USING SMALL MOVING PLAYING BODIES; VIDEO GAMES; GAMES NOT OTHERWISE PROVIDED FOR
    • A63F7/00—Indoor games using small moving playing bodies, e.g. balls, discs or blocks
    • A63F7/06—Games simulating outdoor ball games, e.g. hockey or football
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms

Landscapes

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

Abstract

1,191,768. A-Homo-steroids. CIBA Ltd. 2 Dec., 1968 [30 Nov., 1967; 20 Dec., 1967; 25 June, 1968], No. 57073/68. Headings C2C and C2U. Novel 4-oxo-19-nor-A-homo-steroid-1,5(10)- dienes are prepared by reacting 3-oxo 10- hydroxymethyl-steroid-1,4-dienes in which the 19-hydroxy group is reactively esterified with an alkali metal in an aprotic solvent and in the presence of a polynuclear aromatic hydrocarbon and then isomerizing the 4-oxo-19-nor-A-homosteroid-2,5(10)-diene first formed. In the products, a ketalized oxo group may be liberated, an esterified or etherified OH group hydrolysed, a 17-oxo group reduced with or without introduction of a 17-aliphatic hydrocarbon substituent with, if required, protection of a 3-keto group, and/or an OH group esterified or etherified. Particularly, a 4-keto group may be enolacylated to give a 4-acyloxy-19-nor-A-homosteroid-1,3,5(10)-triene. The products, on bromination in presence of a tertiary amine, yield the known 4-oxo-19-nor-A-homo-steroid-1(10), 2,4a-trienes. 3 - Oxo - 17 - ethylenedioxy - 19 - mesyloxy - #<SP>1</SP>'<SP>4</SP>-androstadiene is prepared by ketalization of the 17-one, itself prepared by dehydrogenation of the #<SP>4</SP>-compound. 3-Oxo-17α-methyl-17#- hydroxy - 19 - chlor - #<SP>1,4</SP> - androstadiene is prepared by dehydrogenation of the #<SP>4</SP>-compound, itself prepared by hydrolysis of 3-ethoxy-17α- methyl - 17# - hydroxy - 19 - chlor - #<SP>3,5</SP>-androstadiene, prepared in turn from the 17-one. The corresponding 17α-ethynyl compounds are prepared similarly. 3-Oxo-17α-hydroxy-19-mesyloxy - 20 - ethylenedioxy - #<SP>1,4</SP> - pregnadiene is prepared by ketalization of the 20-one, prepared in turn by dehydrogenating 3,20-dioxo-17α-acetoxy-19-mesyloxy-#<SP>4</SP>-pregnene (from the 19-ol) and hydrolysing the #<SP>1,4</SP>-17-acetate. 3-Oxo-19- mesyloxy-#<SP>1,4</SP>-cholestadiene is prepared by dehydrogenation of the #<SP>4</SP>-compound, prepared in turn by hydrolysing 3#-acetoxy-19-mesyloxy-#<SP>5</SP>- cholestene (from the 19-ol) to the 3#-ol, oxidizing to the 3-one and isomerizing this. 3 - Oxo - 17α - hydroxy - 20 - ethylenedioxy - 5,19 - cyclo - #<SP>1,6</SP> - pregnadiene and 4 - oxo - 17α - hydroxy - 20 - ethylenedioxy - A - homo - #<SP>1</SP>'<SP>5</SP> - 19 - nor-pregnadiene are by-products in the preparation of the A-homo-#<SP>1</SP>'<SP>5(10)</SP>-19-nor-pregnadiene by the process of the invention. 3-Oxo-17- ethylenedioxy - 5,19 - cyclo - #<SP>1</SP> - androstene is a similarly-produced by-product. The A-homo-steroids of the invention, which are stated to possess valuable pharmacological properties, may be made up into pharmaceutical compositions with suitable carriers.
GB5707368A 1967-11-30 1968-12-02 4-Oxo-19-Nor-A-Homo-Steroid Dienes and a Process for their Manufacture Expired GB1191768A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH1686167A CH505808A (en) 1967-11-30 1967-11-30 4-oxo-19-nor-a-homosteroids intermediates
CH1788767 1967-12-20
CH940568A CH527809A (en) 1967-11-30 1968-06-25 4-oxo-19-nor-a-homosteroids intermediates

Publications (1)

Publication Number Publication Date
GB1191768A true GB1191768A (en) 1970-05-13

Family

ID=27176217

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5707368A Expired GB1191768A (en) 1967-11-30 1968-12-02 4-Oxo-19-Nor-A-Homo-Steroid Dienes and a Process for their Manufacture

Country Status (7)

Country Link
AT (1) AT294327B (en)
BE (1) BE724726A (en)
DE (1) DE1810247A1 (en)
DK (1) DK124128B (en)
FR (1) FR1593376A (en)
GB (1) GB1191768A (en)
NL (1) NL6817135A (en)

Also Published As

Publication number Publication date
DK124128B (en) 1972-09-18
FR1593376A (en) 1970-05-25
DE1810247A1 (en) 1969-07-17
NL6817135A (en) 1969-06-03
AT294327B (en) 1971-11-25
BE724726A (en) 1969-05-29

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees