GB872484A - 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
GB872484A
GB872484A GB37878/58A GB3787858A GB872484A GB 872484 A GB872484 A GB 872484A GB 37878/58 A GB37878/58 A GB 37878/58A GB 3787858 A GB3787858 A GB 3787858A GB 872484 A GB872484 A GB 872484A
Authority
GB
United Kingdom
Prior art keywords
pregnene
fluoro
dione
hydroxy
dihydroxy
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
GB37878/58A
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 GB872484A publication Critical patent/GB872484A/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 6-fluoro-11b ,17a -dihydroxy-4-pregnene-3,20-dione, 6-fluoro-17a -hydroxy-4-pregnene-3,11,20-trione, 6 - fluro21-iodo-11b ,17a -dihydroxy-4-pregnene - 3,20-dione, 6 - fluoro-21-iodo-17a -hydroxy-4-pregnene-3,11,20-trione, and a compound of the formula: <FORM:0872484/IV (b)/1> wherein R is a hydrocarbon radical containing 1-10 carbon atoms inclusive and R1 is hydroxy or keto and a process of treating 6-fluoro-11b ,17a ,21-trihdroxy -4- pregnene-3, 20-dione with an organic sulphonyl halide to obtain the corresponding 21-alkyl or aryl sulphonate of 6-fluoro-11b ,17a ,21 - trihydroxy-4-pregnene,3,20-dione, treating the thus-produced 21-ester with an iodinating agent to obtain 6-fluoro-11b ,17a -dihydroxy-21-iodo4-pregnene-3,20-dione, which is reduced, e.g. with zinc dust, sodium thiosulphate, sodium bisulphite and potassium bisulphite to obtain 6-fluoro-11b ,17a -dihydroxy-4-pregnene - 3,20-dione. If desired the 11-hydroxy group may be oxidised to obtain 6-fluoro-17a -hydroxy-4-pregnene-3,11,20-trione. The process is applicable to both the 6a and 6b epimers, the 6b compound being epimerised to the 6a compound by means of a mineral acid, e.g. hydrochloric acid. Illustrative products of the invention are 6a -fluoro-11b ,17a -dihydroxy-4-pregnene-3-20-dione, 6a -fluoro-17a -hydroxy-4-pregnene-3,11,20-trione, 6a -fluoro-11b ,17a ,21-trihydroxy-4-pregnene-3,20-dione 21-methanesulphonate and 6a -fluoro-21-iodo-11b ,17a -hydroxy-4-pregnene-3,20-dione. Specification 872,483 is referred to.ALSO:Pharmaceutical compositions incorporating 6 - fluoro - 11b ,17a - dihydroxy - 4 - pregnene-3,20-dione or 6-fluoro-17a -hydroxy-4-pregnene-3,11,20-trione as active ingredients are administered orally as pills, tablets, capsules, syrups and elixers, in liquid forms which are adaptable to the natural and synthetic cortical steroid hormones for injectable products, or topically in the form of ointments, creams and lotions with or without coacting antibiotics or germicides. Specification 872,483 is referred to.
GB37878/58A 1957-11-29 1958-11-25 Improvements in or relating to steroids and the manufacture thereof Expired GB872484A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US872484XA 1957-11-29 1957-11-29

Publications (1)

Publication Number Publication Date
GB872484A true GB872484A (en) 1961-07-12

Family

ID=22204011

Family Applications (1)

Application Number Title Priority Date Filing Date
GB37878/58A Expired GB872484A (en) 1957-11-29 1958-11-25 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB872484A (en)

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