GB833183A - Improvements in or relating to cyclopentanophenanthrene compounds - Google Patents

Improvements in or relating to cyclopentanophenanthrene compounds

Info

Publication number
GB833183A
GB833183A GB24756/56A GB2475656A GB833183A GB 833183 A GB833183 A GB 833183A GB 24756/56 A GB24756/56 A GB 24756/56A GB 2475656 A GB2475656 A GB 2475656A GB 833183 A GB833183 A GB 833183A
Authority
GB
United Kingdom
Prior art keywords
androstadiene
nortestosterone
diacetoxy
diol
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
GB24756/56A
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.)
Laboratoires Francais de Chimiotherapie SA
Original Assignee
Laboratoires Francais de Chimiotherapie 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 Laboratoires Francais de Chimiotherapie SA filed Critical Laboratoires Francais de Chimiotherapie SA
Publication of GB833183A publication Critical patent/GB833183A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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 19-nor- D 5,7-androstadiene-3b ,17b -diol and the 3b ,17b -diesters thereof derived from carboxylic acids, 3b ,17b -diacetoxy - 19 - nor - D 3,5,7 - androstatriene, 17b - acetoxy - 19 - nor - D 4,6 - androstadiene-3-one and the acetate of 6-bromo-19-nortestosterone, and a process for the preparation of 19 - nor - D 5,7 - androstadiene - 3b ,17b - diol which may commence at any stage in the following synthesis: 19 - nortestosterone is acetylated to form 3b ,17b -diacetoxy-19-nor-D 3,5-androstadiene, this compound is brominated with a mixture of bromine, acetic acid and collidine to form the acetate of 6-bromo-19-nortestosterone, this compound is dehydrobrominated with a mixture of lithium bromide and lithium carbonate in dimethyl formamide to form 17b -acetoxy-19-nor- D 4,6 - androstadiene-3-one, this compound is acetylated to give 3b ,17b - diacetoxy - 19 - nor - D 3,5,7 androstadiene which is then reduced with an alkali metal borohydride. The 3b ,17b -diesters such as the diacetate, dibenzoate, and the bis(3,5-dinitrobenzoate), are formed from 19-norD 5,7 - androstadiene - 3b ,17b - diol by normal esterification methods. Detailed examples are given.
GB24756/56A 1957-08-07 1958-07-31 Improvements in or relating to cyclopentanophenanthrene compounds Expired GB833183A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR833183X 1957-08-07

Publications (1)

Publication Number Publication Date
GB833183A true GB833183A (en) 1960-04-21

Family

ID=9296400

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24756/56A Expired GB833183A (en) 1957-08-07 1958-07-31 Improvements in or relating to cyclopentanophenanthrene compounds

Country Status (1)

Country Link
GB (1) GB833183A (en)

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