GB1008274A - Process for the manufacture of steroid-dienes - Google Patents

Process for the manufacture of steroid-dienes

Info

Publication number
GB1008274A
GB1008274A GB4273862A GB4273862A GB1008274A GB 1008274 A GB1008274 A GB 1008274A GB 4273862 A GB4273862 A GB 4273862A GB 4273862 A GB4273862 A GB 4273862A GB 1008274 A GB1008274 A GB 1008274A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
oxo
dioxo
pregnene
chloro
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
GB4273862A
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 CH1309261A external-priority patent/CH454841A/en
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB1008274A publication Critical patent/GB1008274A/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
    • 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
    • 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
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

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

Abstract

The invention comprises (1) a process for preparing 19 - oxygenated - D 4,6 - 3 - oxo - steroids of the androstane, pregnane, cholane, cholestane, spirostane or cardanolide series by treating corresponding 19 - oxygenated - D 4 - 3 - oxo-steroids with a dehydrogenating agent such as manganese dioxide or a quinone; and (2) D 4,6 - 3 - oxo - 6 - halogeno - 19 - hydroxy -pregnadienes. The 19-group in the starting materials for process (1) may be a free, esterified or etherified 19-hydroxyl group or a free or protected 19-oxo group or an esterified steroid 19-acid, and the starting material may also contain free, ketalized or enolized oxo groups, esterified or etherified hydroxy groups, alkyl groups or halogen atoms in other positions of the steroid nucleus and 17-side chain, particularly 6-halo or 6-methyl groups. The new steroids (2) are particularly D 4,6 - 3,20 - dioxo - 6 - chloro - 19 -hydroxy-pregnadiene and the 17a -hydroxy and -acetoxy analogues thereof. Examples are given. D 4 - 3,20 - dioxo - 6a - chloro - 17a - acetoxy - 19 -hydroxy-pregnene is prepared by acetylating D 4 - 3,20 - dioxo - 17a - acetoxy - 19 - hydroxy-pregnene to give D 4-3,20-dioxo-17a ,19-diacetoxy-pregnene, converting this to the D 3,5-3-ethyl enol ether, treating this with N-chloro-succinimide to give D 4 - 3,20 - dioxo - 6a - chloro - 17a , 19 - diacetoxy-pregnene and selectively hydrolysing this. Other 19-oxygenated-6-halogenated-D 4-3-oxo-steroids are prepared similarly via enol ethers or esters. Specifications 994,749, 1,007,256 and 1,007,257 are referred to.
GB4273862A 1961-11-10 1962-11-12 Process for the manufacture of steroid-dienes Expired GB1008274A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1309261A CH454841A (en) 1961-11-10 1961-11-10 Method of making steroid dienes
CH1517061 1961-12-29

Publications (1)

Publication Number Publication Date
GB1008274A true GB1008274A (en) 1965-10-27

Family

ID=25711533

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4273862A Expired GB1008274A (en) 1961-11-10 1962-11-12 Process for the manufacture of steroid-dienes

Country Status (1)

Country Link
GB (1) GB1008274A (en)

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