GB1279489A - 09-norprogesterones - Google Patents

09-norprogesterones

Info

Publication number
GB1279489A
GB1279489A GB44788/69A GB4478869A GB1279489A GB 1279489 A GB1279489 A GB 1279489A GB 44788/69 A GB44788/69 A GB 44788/69A GB 4478869 A GB4478869 A GB 4478869A GB 1279489 A GB1279489 A GB 1279489A
Authority
GB
United Kingdom
Prior art keywords
compounds
prepared
derivatives
tetraenes
dehydro
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
GB44788/69A
Inventor
Arthur Friedrich Marx
Hermanus Jacobus Kooreman
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.)
KONINK NEDELANDSCHE GIST EN SP
Original Assignee
KONINK NEDELANDSCHE GIST EN SP
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 KONINK NEDELANDSCHE GIST EN SP filed Critical KONINK NEDELANDSCHE GIST EN SP
Priority to GB44788/69A priority Critical patent/GB1279489A/en
Publication of GB1279489A publication Critical patent/GB1279489A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1279489 19 - Norprogesterone derivatives KONINKLIJKE NEDERLANDSCHE GISTEN SPIRITUSFABRIEK NV 10 Sept 1969 [11 Sept 1968] 44788/69 Divided out of 1277886 Heading C2U The invention comprises compounds of Formulµ I and VI: wherein R is C 1-5 aliphatic hydrocarbyl or phenyl and R<SP>1</SP> is C 1-4 alkyl. Compounds I are prepared by hydrolysis of compounds VI or analogous compounds having other 20-protecting groups. Compounds VI are prepared by Na/NH 3 reduction of the corresponding 1,3,5(10)-trienes. When R = phenyl, the 14α,17α- benzylidenedioxy group is cleaved during the reduction and the resulting 14α,17α-diol must consequently be reacted with benzaldehyde to re-insert it. Compounds of Formulae III, IV and V: are prepared by reduction of the corresponding 1,3,5(10),9(11)-tetraenes. Compounds V (and the corresponding 1,3,5(10),9(11)-tetraenes) are also prepared from compounds III (and the corresponding 1,3,5(10),9(11) - tetraenes) via compounds IV (and the corresponding 1,3,5(10), 9(11)-tetraenes). Compounds III are also prepared from 14α,17α-dihydroxyprogesterone via 11(α or #),- 14α,17α-trihydroxyprogesterone; the 11α-methanesulphonate of the said 11α-ol (optionally); 14α,17α - dihydroxy - 9(11) - dehydroprogesterone; 14α,17α - dihydrozy . 1,9(11) - bisdehydroprogesterone; 3,14α,17α - trihydroxy - 19 - norpregna - 1,3,5(10),9(11) - tetraen - 20 - one; and 3,14α,17α - trihydroxy - 19 - norpregna - 1,3,5(10)- trien-20-one or the 9#-epimer thereof. The 9(11 )-dehydro derivatives of compounds III are prepared from compounds of formula via the 11 -hydroxy, 11-hydroxy-1-dehydro and 1,9(11)-bisdehydro derivatives of the latter. The said 11-hydroxy derivatives are also prepared by acetalization of 11#, 14α, 17α-trihydroxyprogesterone. Compounds V are also prepared from compounds VII via the 1-dehydro and 1-dehydro-20- ketal derivatives of the latter and the 3-hydroxy parents of the former. Compounds VII are prepared by acetalization of 14α,17α-dihydroxyprogesterone. Compounds I are stated to possess progestational and contraceptive activity and may be made up with carriers into pharmaceutical compositions for oral and parenteral administration.
GB44788/69A 1968-09-11 1968-09-11 09-norprogesterones Expired GB1279489A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB44788/69A GB1279489A (en) 1968-09-11 1968-09-11 09-norprogesterones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB44788/69A GB1279489A (en) 1968-09-11 1968-09-11 09-norprogesterones

Publications (1)

Publication Number Publication Date
GB1279489A true GB1279489A (en) 1972-06-28

Family

ID=10434745

Family Applications (1)

Application Number Title Priority Date Filing Date
GB44788/69A Expired GB1279489A (en) 1968-09-11 1968-09-11 09-norprogesterones

Country Status (1)

Country Link
GB (1) GB1279489A (en)

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Legal Events

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