GB923736A - Improvements in or relating to steroids - Google Patents

Improvements in or relating to steroids

Info

Publication number
GB923736A
GB923736A GB3482559A GB3482559A GB923736A GB 923736 A GB923736 A GB 923736A GB 3482559 A GB3482559 A GB 3482559A GB 3482559 A GB3482559 A GB 3482559A GB 923736 A GB923736 A GB 923736A
Authority
GB
United Kingdom
Prior art keywords
ethyl
hydroxy
dione
compound
androsta
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
GB3482559A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf 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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB923736A publication Critical patent/GB923736A/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 steroids of the general formula <FORM:0923736/IV(a)/1> wherein R represents a keto or b -hydroxy radical, and the corresponding 3-semicarbazones and 3-oximes, and the preparation of 17a -ethyl-17b -hydroxy-D 1,4-androstadiene-3,11-dione by treating 3a -acetoxy-5b -androsta-11, 17-dione with an alkali metal acetylide to form 17a - ethynyl - 3a ,17b -dihydroxy-5b -androstan-11-one, catalytically hydrogenating this compound to form the corresponding 17a -ethyl compound, bromoxidising the 17a -ethyl compound with an N-bromoamide to form 4b -bromo - 17a - ethyl-17b -hydroxy-5b -androsta-3,11-dione, brominating this compound to form 2b ,4b - dibromo - 17a -ethyl-17b -hydroxy-5b -androsta-3,11-dione and dehydrobrominating this compound, the preparation of 17a -ethyl - 11b ,17a - dihydroxy - D 1,4 - androstadien-3-one by converting 17a -ethyl-17b -hydroxy-D 1,4-androstadiene-3,11-dione into the corresponding 3-semicarbazone or oxime, reducing the 11-keto group to an 11b -hydroxy group with an alkali metal borohydride, and regenerating the 3-keto group by reaction with pyruvic acid. Specifications 816,909, 923,737 and 923,738 are referred to.
GB3482559A 1958-10-24 1959-10-14 Improvements in or relating to steroids Expired GB923736A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR777439A FR1261174A (en) 1958-10-24 1958-10-24 Process for the preparation of novel derivatives of delta 1-dehydro adrenosterone

Publications (1)

Publication Number Publication Date
GB923736A true GB923736A (en) 1963-04-18

Family

ID=8707820

Family Applications (3)

Application Number Title Priority Date Filing Date
GB3925162A Expired GB923737A (en) 1958-10-24 1959-10-14
GB3482559A Expired GB923736A (en) 1958-10-24 1959-10-14 Improvements in or relating to steroids
GB3825262A Expired GB923738A (en) 1958-10-24 1959-10-14 Novel steroid compounds and processes for the preparation thereof

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB3925162A Expired GB923737A (en) 1958-10-24 1959-10-14

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB3825262A Expired GB923738A (en) 1958-10-24 1959-10-14 Novel steroid compounds and processes for the preparation thereof

Country Status (5)

Country Link
BE (1) BE583959A (en)
CH (1) CH394179A (en)
ES (1) ES252828A1 (en)
FR (1) FR1261174A (en)
GB (3) GB923737A (en)

Also Published As

Publication number Publication date
BE583959A (en) 1960-04-25
CH394179A (en) 1965-06-30
GB923738A (en) 1963-04-18
FR1261174A (en) 1961-05-19
ES252828A1 (en) 1959-12-16
GB923737A (en) 1963-04-18

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