GB926372A - 1.2-methylene and 1.2-diazomethylene-3-ketosteroids and a process for their manufacture - Google Patents

1.2-methylene and 1.2-diazomethylene-3-ketosteroids and a process for their manufacture

Info

Publication number
GB926372A
GB926372A GB3272459A GB3272459A GB926372A GB 926372 A GB926372 A GB 926372A GB 3272459 A GB3272459 A GB 3272459A GB 3272459 A GB3272459 A GB 3272459A GB 926372 A GB926372 A GB 926372A
Authority
GB
United Kingdom
Prior art keywords
steroids
keto
methylene
esters
diazomethylene
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
GB3272459A
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.)
Bayer Pharma AG
Original Assignee
Schering 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 DESCH26339A external-priority patent/DE1096353B/en
Application filed by Schering AG filed Critical Schering AG
Publication of GB926372A publication Critical patent/GB926372A/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
    • 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
    • A61K31/57—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
    • 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
    • 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
    • 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
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • 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

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)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 1.2-methylene-D 4-and D 4,6-3-keto-steroids and 1,2-diazomethylene-D 4,6-3-keto-steroids, and processes for the preparation of 1,2-diazomethylene-D 4,6-3-keto-steroids by reacting diazomethane and D 1,4,6-3-keto-steroidspreferably in an inert organic solvent, of 1,2-methylene-D 4,6-3-keto-steroids by eliminating nitrogen from 1,2-diazomethylene-D 4,6-3-keto-steroids by heating or by treating the diazo compounds with an acid catalyst such as perchloric acid, at room temperature, and of 1,2-methylene-D 4-3-keto-steroids by selectively hydrogenating 1,2-methylene- D 4,6-3- ketosteroids. The steroids referred to above may contain various substituents especially at the 17-positionparticularly a hydroxy group in a free or functionally converted form such as an ester group derived from a lower aliphatic acid, and/or side chains such as an alkyl, acetyl or hydroxyacetyl group. Thus the above steroids may be derived from D 4,6-androstadiene-17b -ol-3-one or esters thereof, D 4,6-pregnadiene-17a -ol-3,20-dione and esters thereof, D 4,6-pregnadiene-17a ,21-diols and 21-esters thereof, D 4,6-pregnadiene- 11b ,17a ,21-triol-3,20-dione and 21-esters thereof, and D 4-androsten-17b -ol-3-one and esters thereof.
GB3272459A 1958-10-25 1959-09-25 1.2-methylene and 1.2-diazomethylene-3-ketosteroids and a process for their manufacture Expired GB926372A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DESC024917 1958-10-25
DESCH26339A DE1096353B (en) 1959-07-11 1959-07-11 Process for the preparation of 1,2-methylene-3-ketosteroids

Publications (1)

Publication Number Publication Date
GB926372A true GB926372A (en) 1963-05-15

Family

ID=25992757

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3272459A Expired GB926372A (en) 1958-10-25 1959-09-25 1.2-methylene and 1.2-diazomethylene-3-ketosteroids and a process for their manufacture

Country Status (4)

Country Link
BE (1) BE583960A (en)
CH (1) CH376905A (en)
DK (1) DK110082C (en)
GB (1) GB926372A (en)

Also Published As

Publication number Publication date
CH376905A (en) 1964-04-30
DK110082C (en) 1968-09-23
BE583960A (en) 1960-04-25

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