GB817382A - 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
GB817382A
GB817382A GB33400/56A GB3340056A GB817382A GB 817382 A GB817382 A GB 817382A GB 33400/56 A GB33400/56 A GB 33400/56A GB 3340056 A GB3340056 A GB 3340056A GB 817382 A GB817382 A GB 817382A
Authority
GB
United Kingdom
Prior art keywords
methyl
compounds
trihydroxy
alkyl
pregnen
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
GB33400/56A
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.)
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 GB817382A publication Critical patent/GB817382A/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 compounds having the general formula <FORM:0817382/IV (b)/1> wherein the lower alkyl group contains from 1-8 carbon atoms inclusive, and the preparation thereof either by subjecting a 2-lower alkyl - 11b ,17a ,20a - trihydroxy - 21 - acyloxy-4-pregnen-3-one to oxidation to split off the 17-side chain and produce a 17-keto group by treatment with periodic acid, lead tetracetate, phenyliodoacetate or sodium bismuthate, or by oxidizing the corresponding 2-lower-alkyl-11b , 17a ,21 - trihydroxy - 4 - pregnene - 3,20 - dione 11b -acylates with chromic acid in acetic acid solution and then hydrolysing. Treatment of the 17-keto compounds with Me Mg Br in ether solution produces the corresponding 11-oxygenated 17a -methyl-testosterones. Examples describe the preparation of 2-methyl- and 2-ethyl - 11b - hydroxy - 4 - androstene - 3,17-dione, and alternative 2-alkyl starting compounds are mentioned. 2 - Methyl - 11b ,17a ,20a - trihydroxy - 21 - acetoxy - 4 - pregnen - 3 - one is obtained by oxidatively hydroxylating 2 - methyl - 11b - hydroxy - 21 - acetoxy - 4,17(20) - pregnadien-3-one. In a similar manner the corresponding 2-ethyl, propyl, butyl, pentyl, hexyl, heptyl and octyl compounds are obtained.
GB33400/56A 1955-11-16 1956-11-01 Improvements in or relating to steroids and the manufacture thereof Expired GB817382A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US817382XA 1955-11-16 1955-11-16

Publications (1)

Publication Number Publication Date
GB817382A true GB817382A (en) 1959-07-29

Family

ID=22166064

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33400/56A Expired GB817382A (en) 1955-11-16 1956-11-01 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB817382A (en)

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