GB935611A - New cyclopentanophenanthrene derivatives and process for the production thereof - Google Patents

New cyclopentanophenanthrene derivatives and process for the production thereof

Info

Publication number
GB935611A
GB935611A GB4284459A GB4284459A GB935611A GB 935611 A GB935611 A GB 935611A GB 4284459 A GB4284459 A GB 4284459A GB 4284459 A GB4284459 A GB 4284459A GB 935611 A GB935611 A GB 935611A
Authority
GB
United Kingdom
Prior art keywords
acetate
acyloxy
hydroxy
methyl
compounds
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
GB4284459A
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.)
Syntex SA
Original Assignee
Syntex SA
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 Syntex SA filed Critical Syntex SA
Publication of GB935611A publication Critical patent/GB935611A/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
    • A61K31/573—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 substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • 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)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the general formula: <FORM:0935611/IV(a)/1> (wherein R is hydroxy or acyloxy (containing from one to twelve carbon atoms inclusive) and X is fluorine or chlorine) and their preparation from a 3b -acyloxy-D 5-spirosten-12-one by dehydrogenation at C9-C11 with selenium dioxide in t-butanol/pyridine, Wolff-Kishner reduction of the 12-oxo group, degradation to a 3b -acyloxy-D 5,9(11),16-pregna trien-20-one, conversion to 3b -hydroxy-16a -methyl-D 5,9(11)-pregnadien-20-one by means of a Grignard reaction with methyl magnesium bromide, Oppenauer oxidation to 16a -methyl-D 4,9(11)-pregnadiene-3,20-dione, addition of HOBr to yield the 9a -bromo-11b -hydroxy derivative, elimination of HBr, treatment of the resulting 9,11-epoxide with HCl or HF, and acetoxylation at C21 via the 21-iodo compound. Saponification of the 21-acetate and subsequent re-esterification yields other 21-acylates. Specified starting materials are botogenin acetate, correllogenin acetate and gentrogenin acetate or mixtures of the latter two compounds. The invention is illustrated by four detailed examples. Specification 776,858 is referred to.
GB4284459A 1958-12-20 1959-12-16 New cyclopentanophenanthrene derivatives and process for the production thereof Expired GB935611A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
MX5314358 1958-12-20

Publications (1)

Publication Number Publication Date
GB935611A true GB935611A (en) 1963-08-28

Family

ID=19742869

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4284459A Expired GB935611A (en) 1958-12-20 1959-12-16 New cyclopentanophenanthrene derivatives and process for the production thereof

Country Status (1)

Country Link
GB (1) GB935611A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3923985A (en) * 1973-07-27 1975-12-02 Roussel Uclaf Process for the preparation of 16{60 -methyl-{66 {hu 1,4,9(11){b -pregnatrien-3,20-diones and use of the same in treatment of allergies

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3923985A (en) * 1973-07-27 1975-12-02 Roussel Uclaf Process for the preparation of 16{60 -methyl-{66 {hu 1,4,9(11){b -pregnatrien-3,20-diones and use of the same in treatment of allergies

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