GB870123A - 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
GB870123A
GB870123A GB30470/59A GB3047059A GB870123A GB 870123 A GB870123 A GB 870123A GB 30470/59 A GB30470/59 A GB 30470/59A GB 3047059 A GB3047059 A GB 3047059A GB 870123 A GB870123 A GB 870123A
Authority
GB
United Kingdom
Prior art keywords
methyl
dione
dihydroxy
fluoro
pregnadiene
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
GB30470/59A
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 GB870123A publication Critical patent/GB870123A/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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 16a -methyl steroids of the formulae: <FORM:0870123/IV (b)/1> <FORM:0870123/IV (b)/2> wherein Y is the b -hydroxy-methylene or carbonyl group, X11 is hydrogen, fluorine or chlorine and X1 is hydrogen or fluorine, and the processes for the preparation thereof (a) by treating compounds of the formula: <FORM:0870123/IV (b)/3> with an organic sulphonyl halide, e.g. toluenesulphonyl chloride, to obtain the corresponding 21-sulphonate ester, treating the 21-sulphonate ester thus obtained with NaI to obtain the corresponding 21-iodo compound, treating the 21-iodo compound thus obtained with silver fluoride to obtain the corresponding 21-fluoro compound which may be oxidised to the 11-keto compound; alternatively the 21-sulphonate ester is treated with potassium fluoride to obtain the 21-fluoro compound directly; (b) by treating the 21-iodo compound obtained in (a) with a reducing agent, e.g. sodium thiosulphate or potassium bisulphite, to obtain the 21-unsubstituted compound. Illustrative products of the invention are 11b , 17a -dihydroxy-16a -methyl-21-fluoro-4-pregnene -,20-dione, 9a ,21-difluoro-11b ,17a -dihydroxy-16a -methyl-4-pregnene-3, 20-dione, 11b ,17a -dihydroxy-16a -methyl-21- fluoro-1,4-pregnadiene-3, 20-dione, 9a ,21-difluoro-11b ,17a -dihydroxy-16a -methyl-1,4-pregnadiene-3, 20-dione, 11b , 17a -dihydroxy-16a -methyl-4-pregnene-3,20-dione, 9a -fluoro-11b ,17a -dihydroxy-16a -methyl-4-pregnene-3,20-dione, 11b ,17a -dihydroxy-16a -methyl-1,4-pregnadiene-3,20-dione and 9a -fluoro-11b ,17a -dihydroxy- 16a -methyl-1,4-pregnadiene-3, 20-dione. Specification 869,511 is referred to.ALSO:Pharmaceutical compositions incorporate 11b -17a - dihydroxy - 16a - methyl - 4 - pregnene-3,20 - dione, 16a - methyl - 17a - hydroxy - 4 - pregnene - 3,11,20 - trione, 11b - 17a - dihydroxy - 16a - hydroxy - 1,4 - pregnadiene - 3,20 - dione, 16a - methyl - 17a - hydroxy - 1,4 - pregnadiene - 3,11,20 - trione, 11b ,17a - dihydroxy - 16a - methyl - 21 - fluoro-4 - pregnene - 3,20 - dione, 16a - methyl - 17a -hydroxy - 21 - fluoro - 4 - pregnene - 3,11,20-trione, 11b ,17a - dihydroxy - 16a - methyl - 21-fluoro - 1,4 - pregnadiene - 3,20 - dione, 16a -methyl - 17a - hydroxy - 21 - fluoro - 1, 4-pregnadiene-3,11,20-trione or the corresponding 9-chloro or 9-fluoro compounds. They may be in the forms of ointments, creams, solutions, suspensions, lotions and sprays. In addition penicillins, neomycin, tetracycline, chloramphenicol and novobiocin may be present. Specification 869,511 is referred to.
GB30470/59A 1958-09-08 1959-09-07 Improvements in or relating to steroids and the manufacture thereof Expired GB870123A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US870123XA 1958-09-08 1958-09-08

Publications (1)

Publication Number Publication Date
GB870123A true GB870123A (en) 1961-06-14

Family

ID=22202400

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30470/59A Expired GB870123A (en) 1958-09-08 1959-09-07 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB870123A (en)

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