GB739175A - Steroid compounds - Google Patents

Steroid compounds

Info

Publication number
GB739175A
GB739175A GB938/53A GB93853A GB739175A GB 739175 A GB739175 A GB 739175A GB 938/53 A GB938/53 A GB 938/53A GB 93853 A GB93853 A GB 93853A GB 739175 A GB739175 A GB 739175A
Authority
GB
United Kingdom
Prior art keywords
triacetoxy
oxido
acid
pregnene
pregnane
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
GB938/53A
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 GB739175A publication Critical patent/GB739175A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • 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 17(20) - oxido-3 : 11a : 20-tri-acyloxy pregnanes wherein the acyloxy groups are the same or different and are preferably derived from unsubstituted organic carboxylic acids containing from one to eight carbon atoms inclusive. The above compounds may be prepared by epoxidizing the corresponding 3 : 11a : 20-acyloxy-17(20)-pregnene using an organic per-acid or hydrogen peroxide Specified per-acids are per-acetic, perpropionic, perbutyric, perbenzoic and chlorperacetic, and the reaction is preferably effected in an organic solvent, e.g. chloroform, carbon tetrachloride, ethylene dichloride, methylene chloride, and ether-chloroform mixtures, which may contain a small quantity of an alkali metal salt, e.g. sodium acetate. In examples (1) 3a : 11a : 20 - triacetoxy - 17(20) - pregnene in chloroform below 5 DEG C. is treated with peracetic acid containing sodium acetate, the mixture diluted with methylene chloride washed with aqueous sodium hydroxide, and 17(20)-oxido-3a : 11a : 20 - triacetoxy pregnane isolated by evaporation of the solvent. (2) As in (1) using perbenzoic acid in benzene for the epoxylation. Further examples using the method of (1) or (2) describe the preparation of 3a : 11a : 20-tripropionoxy-, 3a : 11a - diacetoxy - 20 - propionoxy-and 3b : 11a : 20 - triacetoxy - 17(20) - oxido pregnane. Numerous other 17(20)-oxido-3a (or b ) : 11a : 20 - triacyloxypregnanes are listed. The necessary starting materials, 3a : 11a : 20-triacetoxy -, 3a : 11a : 20 - tripropionoxy -, 3a : 11a - diacetoxy - 20 - propionoxy - and 3b : 11a : 20 - triacetoxy - 17(20) - pregnene are prepared from the appropriate 3 : 11a : 20-hydroxypregnane - 20 - one (or an 11a or 3 : 11a -ester thereof) by treatment with p-toluene sulphonic acid and the appropriate acid anhydride. The preparation of 11a -hydroxy-pregnane - 3 : 20 - dione and its 11 - acetate; 3a : 11a - dihydroxypregnane - 20 - one and its 11a - and 3 : 11a -esters are also described. Specification 724,094 is referred to.
GB938/53A 1952-01-18 1953-01-12 Steroid compounds Expired GB739175A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US739175XA 1952-01-18 1952-01-18

Publications (1)

Publication Number Publication Date
GB739175A true GB739175A (en) 1955-10-26

Family

ID=22116569

Family Applications (1)

Application Number Title Priority Date Filing Date
GB938/53A Expired GB739175A (en) 1952-01-18 1953-01-12 Steroid compounds

Country Status (1)

Country Link
GB (1) GB739175A (en)

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