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GB843901A - Improvements in or relating to cyclopentanophenanthrene compounds - Google Patents

Improvements in or relating to cyclopentanophenanthrene compounds

Info

Publication number
GB843901A
GB843901A GB38530/58A GB3853058A GB843901A GB 843901 A GB843901 A GB 843901A GB 38530/58 A GB38530/58 A GB 38530/58A GB 3853058 A GB3853058 A GB 3853058A GB 843901 A GB843901 A GB 843901A
Authority
GB
United Kingdom
Prior art keywords
androstadiene
dione
fluoro
compound
trione
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
GB38530/58A
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.)
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 GB843901A publication Critical patent/GB843901A/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 D 1,4,9(11)-ondrostatriene- -3,17-dione, 9a -bromo (and fluoro) - D 1,4 -androstadiene- -11b -ol-3,17-dione, 9a -fluoro-D 1,4-androstadiene- -3,11,17-trione and 9b , 11b -epoxy- D 1,4-androstadiene-3,17-dione, and a process comprising the treatment of 11b -hydroxy- D 1,4-androstadiene -3,17-dione with mesyl or tosyl chloride to form D 1,4,9-androstatriene-1,37-dione, this compound is brominated with N-bromosuccinimide to produce 9a -bromo- D 1,4-androstadiene-11b - ol-3,17 - dione, this compound is treated with an alkali metal hydroxide to produce 9b , 11b -epoxy- D 1,4-androstadiene-3, 17-dione and the last mentioned compound is fluorinated with hydrofluoric acid to form 9a -fluoro- D 1,4-androstadiene-11b -ol- 3,17-dione with the optional further step of oxidising this compound to form 9a -fluoro - D 1,4-androstadiene - 3,11,17 - trione e.g. with chromic acid. The treatment with mesyl or tosyl chloride may be carried out in the presence of pyridine and a catalytic amount of thionyl chloride in dimethylformamide as solvent. The bromination may be effected in dioxane and in the presence of perchloric or sulphuric acid. Detailed examples are given.
GB38530/58A 1957-12-06 1958-11-28 Improvements in or relating to cyclopentanophenanthrene compounds Expired GB843901A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR843901X 1957-12-06

Publications (1)

Publication Number Publication Date
GB843901A true GB843901A (en) 1960-08-10

Family

ID=9312137

Family Applications (1)

Application Number Title Priority Date Filing Date
GB38530/58A Expired GB843901A (en) 1957-12-06 1958-11-28 Improvements in or relating to cyclopentanophenanthrene compounds

Country Status (1)

Country Link
GB (1) GB843901A (en)

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