GB874779A - New steroid compounds and processes for their preparation - Google Patents

New steroid compounds and processes for their preparation

Info

Publication number
GB874779A
GB874779A GB42918/59A GB4291859A GB874779A GB 874779 A GB874779 A GB 874779A GB 42918/59 A GB42918/59 A GB 42918/59A GB 4291859 A GB4291859 A GB 4291859A GB 874779 A GB874779 A GB 874779A
Authority
GB
United Kingdom
Prior art keywords
dione
dihydroxy
preparation
ketone group
dehydrobromination
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
GB42918/59A
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 GB874779A publication Critical patent/GB874779A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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 compounds of the general formula <FORM:0874779/IV (b)/1> (wherein X represents hydrogen or bromine and Ac an acyl radical, e.g. acetyl, benzoyl, hexahydrobenzoyl, m-sulphobenzoyl or b -cyclopentylpropionyl), and the preparation thereof by protecting the 20-ketone group of 3a ,17a -dihydroxy-16a -methylpregnane-11, 20-dione (e.g. by conversion to the 20-semicarbazone), reducing the 11-ketone group and liberating the 20-ketone group to form 3a ,11a , 17a -trihydroxy-16a -methylpregnan -20- one, dehydrating this to yield 3a ,17a -dihydroxy-16a -methylpregn-9(11 -en-20-one, introducing a halogen substitutent at the 21-position and reacting the product with the appropriate acylating agent to yield a 3a ,17a -dihydroxy-16a -methyl-21-acyloxypregn-9(11)-en -20- one, oxidising this to the 3,20-dione and monoor di-brominating this product. The dehydration step may be preceded by acylation of the 3a -hydroxy group and followed by saponification. 9a -Fluoro-11b ,17a ,21-trihydroxy-16a -methylpregna-1,4-diene-3, 20-dione can be prepared from the compounds of the general formula above by subjecting them to dehydrobromination and dehydrogenation when X=H, or to di-dehydrobromination when X=Br, followed in either case by introduction of an 11b -hydroxy group and a 9a -fluorine atom.
GB42918/59A 1959-01-05 1959-12-17 New steroid compounds and processes for their preparation Expired GB874779A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR874779X 1959-01-05

Publications (1)

Publication Number Publication Date
GB874779A true GB874779A (en) 1961-08-10

Family

ID=9359842

Family Applications (1)

Application Number Title Priority Date Filing Date
GB42918/59A Expired GB874779A (en) 1959-01-05 1959-12-17 New steroid compounds and processes for their preparation

Country Status (1)

Country Link
GB (1) GB874779A (en)

Similar Documents

Publication Publication Date Title
GB1040554A (en) The manufacture of 3-keto-19-alkyl-steroids
GB874779A (en) New steroid compounds and processes for their preparation
GB950390A (en) 3ª‡,9ª‡-epoxy steroids of the androstane and pregnane series
GB881501A (en) Substituted pregnenes
GB967006A (en) Improvements in or relating to steroids
GB996079A (en) 17ª‡,21-substituted methylenedioxy steroids and methods therefor
GB931783A (en) New steroid compounds, and processes for their preparation
GB931221A (en) Steroid compounds
GB955613A (en) New steroid compounds and processes
GB965292A (en) Halogenated steroid derivatives
GB1101116A (en) Steroidal 2ª‡-carboxylic acids and esters
GB929258A (en) Steroids and process for preparation
GB1057337A (en) Novel 3-substituted-androst-11-ones and processes for their preparation
ES254385A1 (en) Procedure for the preparation of delta 9.11-pregneno-halogenated dionas (Machine-translation by Google Translate, not legally binding)
GB970487A (en) Novel steroids compounds and processes for the preparation thereof
GB965324A (en) Steroid compounds
GB918408A (en) Esters of 21-hydroxy steroids and process for preparation
GB970484A (en) New 17-desoxy corticosteroids and processes for their preparation
GB951060A (en) Cyclopentanophenanthrene compounds and process for their preparation
GB951474A (en) Improvements in or relating to the bromination of steroid derivatives
GB991475A (en) Novel steroid compounds and processes for their production
GB943951A (en) New steroid compounds, and processes for their preparation
GB1117406A (en) Process for dehydrohalogenating organic compounds
GB896980A (en) Process for the production of 6-methyl-3-keto-í~-steroid compounds
GB904123A (en) New cyclopentanophenanthrene compounds and process for the production thereof