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GB829476A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Improvements in or relating to steroids and the manufacture thereof

Info

Publication number
GB829476A
GB829476A GB16017/58A GB1601758A GB829476A GB 829476 A GB829476 A GB 829476A GB 16017/58 A GB16017/58 A GB 16017/58A GB 1601758 A GB1601758 A GB 1601758A GB 829476 A GB829476 A GB 829476A
Authority
GB
United Kingdom
Prior art keywords
pregnane
hydroxy
dione
methyl
compound
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
GB16017/58A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB829476A publication Critical patent/GB829476A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J5/00Normal 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J75/00Processes 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 4-halo-11b -hydroxy-11-lower alkyl-5b -pregnane-3,20-dione represented by the formula <FORM:0829476/IV (b)/1> wherein X is a halogen substituent, wherein the lower alkyl radical contains from 1-8 carbon atoms inclusive and a process for the preparation thereof by halogenating 11b -hydroxy - 11a - lower alkyl - 5b - pregnane - 3,20-dione. Halogenation may be effected by chlorine or bromine. The 4-fluoro compound may be obtained by treating the 4-bromo compound with sodium, potassium or silver fluoride and the 4-iodo compound by treating the 4-bromo compound with sodium iodide in acetone. Examples describe the preparation of 4-chloro-11b - hydroxy - 11a - methyl - 5b - pregnane - 3,20-dione, the corresponding 4-bromo compound and 11a -propyl and 11a -amyl compounds. 11b - hydroxy - 11a - methyl - 5b - pregnane-3,20-dione is obtained by converting 5b -pregnane-3,11,20-trione to a 3,20-bis-(ethylene acetal), reacting this with methyl lithium to form 11b - hydroxy - 11a - methyl - 5b - pregnane - 3,20 - dione - 3,20 - bis - (ethylene acetal) and removing the acetal groups with acid. Specification 743,484 is referred to.
GB16017/58A 1957-05-23 1958-05-19 Improvements in or relating to steroids and the manufacture thereof Expired GB829476A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US829476XA 1957-05-23 1957-05-23

Publications (1)

Publication Number Publication Date
GB829476A true GB829476A (en) 1960-03-02

Family

ID=22174468

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16017/58A Expired GB829476A (en) 1957-05-23 1958-05-19 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB829476A (en)

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