GB841243A - 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
GB841243A
GB841243A GB35633/56A GB3563356A GB841243A GB 841243 A GB841243 A GB 841243A GB 35633/56 A GB35633/56 A GB 35633/56A GB 3563356 A GB3563356 A GB 3563356A GB 841243 A GB841243 A GB 841243A
Authority
GB
United Kingdom
Prior art keywords
androstane
hydroxy
alkyl
dione
halo
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
GB35633/56A
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 GB841243A publication Critical patent/GB841243A/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 formula <FORM:0841243/IV(b)/1> wherein R is hydrogen or methyl and X is fluorine, chlorine, bromine or iodine and a process which comprises oxidizing the 11b -hydroxy group to a keto group in a 9a -halo-11b ,17b -dihydroxy - 17a - alkyl - 5a (or 5b ) androstane-3 - one or a 9a - halo - 11b ,17b - dihydroxy-17a - alkyl - 19 - nor - 5a (or 5b ) - androstane-3 - one, or a 17b - monoester thereof, with an oxidizing agent to produce the corresponding 9a - halo - 17b - hydroxy - 17a - alkyl - 5a (or 5b ) - androstane - 3,11 - dione or 9a - halo-17b - hydroxy - 17a - alkyl - 19 - nor - 5a (or 5b ) - androstane - 3,11 - dione, or 17b - monoester thereof. As oxidizing agents there may be used chromic acid, potassium permanganate, potassium dichromate, N-bromoacetamide, Nchlorosuccimide, t - butyl hypochlorite preferably in a solvent e.g. acetic acid, chloroform, or t-butyl alcohol. The alkyl group in 17-position may be ethyl, propyl, isopropyl, butyl, sec.butyl, amyl, hexyl, heptyl or octyl. The 17-acylate e.g. formate, acetate, propionate, benzoate, phenylacetate, a - or b -cyclopentylpropionate, a - or b -phenylpropionate, methylbenzoate, a - or b -furylacrylate, valerate and methacrylate, are obtained by acylation with the appropriate acid, acid anhydride or acid chloride. Examples disclose the production of 9a - fluoro - 17b - hydroxy - 17a - methyl-5a (or 5b ) - androstane - 3,11 - dione, 9a -fluoro - 17b - hydroxy - 17a - methyl - 19 - nor-5a (or b ) - androstane - 3,11 - dione, the corresponding 9a - chloro-, 9a - bromo-, and 9a -iodo-compounds and the 17-acetates thereof. Specification 841,241 is referred to.
GB35633/56A 1955-12-05 1956-11-21 Improvements in or relating to steroids and the manufacture thereof Expired GB841243A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US841243XA 1955-12-05 1955-12-05

Publications (1)

Publication Number Publication Date
GB841243A true GB841243A (en) 1960-07-13

Family

ID=22183021

Family Applications (1)

Application Number Title Priority Date Filing Date
GB35633/56A Expired GB841243A (en) 1955-12-05 1956-11-21 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB841243A (en)

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