GB886390A - 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
GB886390A
GB886390A GB36633/59A GB3663359A GB886390A GB 886390 A GB886390 A GB 886390A GB 36633/59 A GB36633/59 A GB 36633/59A GB 3663359 A GB3663359 A GB 3663359A GB 886390 A GB886390 A GB 886390A
Authority
GB
United Kingdom
Prior art keywords
pregnene
dione
dimethyl
dihydroxy
compounds
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
GB36633/59A
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 GB886390A publication Critical patent/GB886390A/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:0886390/IV (b)/1> wherein X is the b -hydroxymethylene radical <FORM:0886390/IV (b)/2> or the carbonyl radical <FORM:0886390/IV (b)/3> Y is hydrogen or halogen and the 1,2-carbon atom linkage is a single bond or a double bond linkage and a process for the preparation thereof which comprises treating 2a ,6a -dimethylhydrocortisone with an alkyl or aryl sulphonyl halide to obtain the corresponding 21-ester, reacting the thus obtained 21-alkyl or aryl sulphonate with an iodinating agent to obtain the corresponding 21-iodo steroid, dehalogenating this compound to obtain 2a ,6a -dimethyl-11b , 17a -dihydroxy-4-pregnene-3,20-dione (1) dehydrating (1) to obtain the corresponding 4,9(11)-pregnadiene reacting the thus obtained 4,9(11)-pregnadiene with hyphohalous acid to obtain a 9a -halo compound (2), treating (2) with a mild base to obtain 2a ,6a -dimethyl-9b ,11b -oxido-17a -hydroxy-4-pregnene-3,20-dione, hydrohalogenating this compound to obtain 2a ,6a -dimethyl-9a -halo - 11b , 17a - dihydroxy - 4 - pregnene - 3, 20 - dione (3). Compounds (1), (2) and (3) may be oxidised to obtain the corresponding 11-keto compounds or dehydrogenated by chemical or biological methods to obtain the corresponding 1,4-pregnadienes. Illustrative products of the invention are 2a ,6a -dimethyl-11b ,17a -dihydroxy-4-pregnene-3,20-dione, 2a ,6a -dimethyl-9a -fluoro-11b , 17a - dihydroxy - 4 - pregnene - 3, 20 - dione, 2a , 6a , - dimethyl - 9a - chloro - 11b , 17a - di - hydroxy-4-pregnene-3,20-dione, 2a , 6a -dimethyl-7a - bromo - 11b , 17a - dihydroxy - 4 - pregnene - 3,20-dione, the corresponding 11-keto compounds and the corresponding 1,4-pregnadienes. Specifications 724,094 and 872,210 are referred to.ALSO:Pharmaceutical compositions comprise compounds having the formula <FORM:0886390/VI/1> wherein X is the b -hydroxymethylene radical or the carbonyl radical, Y is hydrogen or halogen and the 1,2 carbon linkage is a single or a double-bond linkage, and a pharmaceutical diluent. These compounds are administered orally as tablets, powders, capsules or pills, in liquid forms as solutions, emulsions, suspensions, syrups or elixirs, and topically as ointments, creams, lotions, and liquids with or without coacting antibiotics and germicides. Specifications 724,094 and 872,210 are referred to.
GB36633/59A 1958-12-22 1959-10-28 Improvements in or relating to steroids and the manufacture thereof Expired GB886390A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US886390XA 1958-12-22 1958-12-22

Publications (1)

Publication Number Publication Date
GB886390A true GB886390A (en) 1962-01-03

Family

ID=22212535

Family Applications (1)

Application Number Title Priority Date Filing Date
GB36633/59A Expired GB886390A (en) 1958-12-22 1959-10-28 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB886390A (en)

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