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GB1260392A - 17-substituted estratrienes - Google Patents

17-substituted estratrienes

Info

Publication number
GB1260392A
GB1260392A GB8113/69A GB811369A GB1260392A GB 1260392 A GB1260392 A GB 1260392A GB 8113/69 A GB8113/69 A GB 8113/69A GB 811369 A GB811369 A GB 811369A GB 1260392 A GB1260392 A GB 1260392A
Authority
GB
United Kingdom
Prior art keywords
compounds
alkali metal
alkyl
prepared
tetrahydropyran
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
GB8113/69A
Inventor
Sandor Barcza
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.)
Sandoz AG
Original Assignee
Sandoz 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
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB1260392A publication Critical patent/GB1260392A/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
    • C07J1/0051—Estrane derivatives
    • C07J1/0081—Substituted in position 17 alfa and 17 beta
    • C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
    • C07J1/0096—Alkynyl derivatives
    • 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
    • C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
    • C07J7/0095—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 carbon in position 21 is part of carboxylic group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0044—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an estrane or gonane skeleton, including 18-substituted derivatives and derivatives where position 17-beta is substituted by a carbon atom not directly bonded to another carbon atom and not being part of an amide group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

1,260,392. 17α-Substituted estratrienes. SANDOZ Ltd. 14 Feb., 1969 [26 Feb., 1968; 17 June, 1968], No. 8113/69. Heading C2U. The invention comprises compounds of Formulµ I and II wherein R 1 is C 1-3 alkyl; R 2 is H, C 1-4 alkyl, C 2-4 alkanoyl, benzoyl, cyclopentyl or cyclohexyl; R 2 b<SP>1</SP> is C 1-4 alkyl, cyclopentyl, cyclohexyl, alkali metal, Mg or tetrahydropyran-2-yl ; R 3 is H, C 2-4 alkanoyl or benzoyl; R 4 is wherein R 5 , R 6 and R 7 are each C 1-4 alkyl; and n is 4 or 5; and X is H, alkali metal or Mg; with the provisos that (i) when R 4 is (b) or (c) then R 2 is H or C 1-4 alkyl and R 3 is H; (ii) when R 3 is not H then R 2 also is not H; (iii) when X is H then R 2 b<SP>1</SP> is tetrahydropyran-2-yl. Compounds I wherein R 4 is (a) are prepared either by acid hydrolysis of compounds II or analogues thereof wherein R 2 b<SP>1</SP> is any acidhydrolysable protecting group; or by esterification of the corresponding free 17α-carboxyethynyl compounds using a diazoalkane; and, when required acylation of the 3- and/or 17- hydroxy groups in the thus-obtained products. Compounds I wherein R 4 is (b) are prepared by reaction of the corresponding 17α-(esterified carboxyethynyl) compounds with a compound of formula HN(CH 2 ) n . Compounds I wherein R 4 is (c) are prepared by reaction of the corresponding 17α-(alkoxycarbonylethynyl) compounds with alkanethiols. Compounds II (wherein X and possibly also R 2 b<SP>1</SP> is alkali metal or Mg) are prepared from the corresponding 17-oxo compounds (wherein R 2 b<SP>1</SP> is other than alkali metal or Mg but may be H) by reaction with M<SP>+</SP>(-C#C-CO 2 R 5 )- wherein M is alkali metal or magnesium. Compounds II (wherein X is H and R 2 b<SP>1</SP> is tetrahydropyran-2-yl) are prepared by selective hydrolysis of the corresponding compounds, wherein X is alkali metal or Mg. Compounds I are stated to possess estrogenic, progestational and ovulation-inhibiting activities, and may be made up with carriers into pharmaceutical compositions for oral and parenteral administration. All examples relate to compounds of the estrane series (R 1 =Me).
GB8113/69A 1968-02-26 1969-02-14 17-substituted estratrienes Expired GB1260392A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US70799168A 1968-02-26 1968-02-26
US73733968A 1968-06-17 1968-06-17

Publications (1)

Publication Number Publication Date
GB1260392A true GB1260392A (en) 1972-01-19

Family

ID=27107998

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8113/69A Expired GB1260392A (en) 1968-02-26 1969-02-14 17-substituted estratrienes

Country Status (7)

Country Link
BE (1) BE728870A (en)
CH (1) CH515228A (en)
DE (1) DE1909089A1 (en)
ES (1) ES364004A1 (en)
FR (1) FR2002599A1 (en)
GB (1) GB1260392A (en)
SE (1) SE350490B (en)

Also Published As

Publication number Publication date
BE728870A (en) 1969-08-25
FR2002599A1 (en) 1969-10-31
ES364004A1 (en) 1971-02-16
CH515228A (en) 1971-11-15
SE350490B (en) 1972-10-30
DE1909089A1 (en) 1969-09-11

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees