GB889779A - 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
GB889779A
GB889779A GB27117/59A GB2711759A GB889779A GB 889779 A GB889779 A GB 889779A GB 27117/59 A GB27117/59 A GB 27117/59A GB 2711759 A GB2711759 A GB 2711759A GB 889779 A GB889779 A GB 889779A
Authority
GB
United Kingdom
Prior art keywords
dione
dimethyl
pregnene
dihydroxy
fluoro
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
GB27117/59A
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.)
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 GB889779A publication Critical patent/GB889779A/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 having the formula <FORM:0889779/IV (b)/1> wherein R is b -hydroxy or keto and X is hydrogen or a halogen atom and the 1,2 carbon atom linkage represents a single or double bond, 2a , 6a - dimethyl - 21 - iodo - 11 - oxygenated - 17a - hydroxy - 4 - pregnene - 3, 20 - dione, 2a , 6a - dimethyl - 21 - fluoro - 4, 9(11) - pregna - diene-3,20-dione and processes for the preparation thereof which comprise treating a 2a ,6a -dimethyl - 11 - oxygenated - 17a , 21 - dihydroxy - 4-pregnene-3,20-dione with a organic acid sulphonyl chloride to form the corresponding 21-organic acid sulphonate, heating said sulphonate with an alkali metal iodide to form the corresponding 21-iodo compound, reacting said 21-iodo compound with a metal fluoride to yield 2a , 6a - dimethyl - 21 - fluoro - 11 - oxygenated - 17a - hydroxy - 4 - pregnene - 3, 20 - dione. Dehydration of 2a , 6a - dimethyl - 11b , 17a - dihydroxy - 21 - fluoro - 4 - pregnene - 3, 20 - dione gives the corresponding 4,9(11)-pregnadiene, which with N-bromoacetamide gives the corresponding 9a -bromo compound. Treatment of 2a , 6a - dimethyl - 9a - bromo - 11b , 17a - dihydroxy - 21 - fluoro - 4 - pregnene - 3, 20 - dione with potassium acetate gives a 9(11)-oxido compoound which results in a 9a -halo compound with hydrohalic acid. Illustrative products of the invention are 2,6a -dimethyl-9a , 21 - difluoro - 11b , 17a - dihydroxy - 4 - pregnene-3, 20 - dione, 2, 6a - dimethyl - 9a , 21 - difluoro - 17a - hydroxy - 4 - pregnene - 3, 11, 20 - trione, 2, 6a - 11b , 17a - dihydroxy - 21 - fluoro - 1, 4 - pregnadiene - 3, 20 - dione and 2, 6a - dimethyl - 11b , 17a - dihydroxy - 9a , 21 - difluoro - 1, 4 - pregnadiene-3,20-dione. Specifications 829,903 872,210 are referred to.ALSO:Pharmaceutical compositions comprise a compound having the formula <FORM:0889779/VI/1> wherein R is b -hydroxy or keto and X is hydrogen or a halogen atom and the 1,2-carbon linkage represents a single or double bond and a pharmaceutical carrier. They are employed orally, in liquid forms for injection, or topically as ointments, creams and lotions. Specifications 872,210 and 829,903 are referred to.
GB27117/59A 1958-08-03 1959-08-07 Improvements in or relating to steroids and the manufacture thereof Expired GB889779A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US889779XA 1958-08-03 1958-08-03

Publications (1)

Publication Number Publication Date
GB889779A true GB889779A (en) 1962-02-21

Family

ID=22214621

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27117/59A Expired GB889779A (en) 1958-08-03 1959-08-07 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB889779A (en)

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