GB872112A - 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
GB872112A
GB872112A GB37877/58A GB3787758A GB872112A GB 872112 A GB872112 A GB 872112A GB 37877/58 A GB37877/58 A GB 37877/58A GB 3787758 A GB3787758 A GB 3787758A GB 872112 A GB872112 A GB 872112A
Authority
GB
United Kingdom
Prior art keywords
halo
difluoro
desoxyhydrocortisone
desoxycortisone
pregnene
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
GB37877/58A
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 GB872112A publication Critical patent/GB872112A/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 formulae: <FORM:0872112/IV (b)/1> wherein R1 is a keto or hydroxy group, R is an alkyl or aryl hydrocarbon radical of 1-10 carbon atoms inclusive and X is fluorine, chlorine or bromine, 6,21-difluoro-9a -halo-21-desoxyhydrocortisone and 6,21 - difluoro - 9a - halo-21-desoxycortisone wherein the 9a -halogen is fluorine, chlorine or bromine and a process which comprises treating 6-fluoro-9a -halo-11b , 17a ,21-trihydroxy-4-pregnene-3,20-dione with an alkyl or aryl sulphonyl halide to obtain the corresponding 21-ester, a 21-alkyl or aryl sulphonate of 6-fluoro-9a -halo-11b ,17a ,21- trihydroxy-4-pregnene-3,20-dione, which on treatment with a metal fluoride gives the corresponding 6,21 - difluoro - 9a - halo - 11b ,17a - dihydroxy-4-pregnene-3,20-dione. Alternatively the 6-fluoro-9-halo-11b ,17a ,21-trihydroxy-4-pregnene-3, 20-dione 21-alkyl or aryl sulphonate can be reacted with an alkali metal iodide to produce the corresponding 21-iodo steroid which can be fluorinated to yield the 21-fluoro steroid. If desired the 11b -hydroxy compound can be oxidised to obtain 6,21-difluoro-9a -halo-17a -hydroxy-4-pregnene-3,11, 20-trione. In a variation of the process fluorination at carbon atom 21 may be effected on 6-fluorohydrocortisone followed by halogenation at carbon atom 9. The processes of the invention are applicable to both the 6a and 6b -epimers, the 6b -compound being convertible to the 6a -compound by treatment with acid e.g. HCl. Illustrative products of the invention are 6a 9a ,21-trifluoro21 - desoxyhydrocortisone, 6a 21 - difluoro - 9a - chloro-21-desoxyhydrocortisone, 6a ,21-difluoro9a -bromo-21-desoxyhydrocortisone, 6a 9a ,21-trifluoro-21-desoxycortisone, 6a ,21-difluoro-9a -chloro-21-desoxycortisone, and 6a ,21-difluoro9a -bromo-21-desoxycortisone, and the corresponding 6b -epimers. Specification 850,833 is referred to.ALSO:Pharmaceutical compositions comprise 6,21-difluoro - 9a - halo - 21 - desoxyhydrocortisone or 6,21 - difluoro - 9a - halo - 21 - desoxycortisone and a pharmaceutical diluent. They may be administered orally as pills, tablets, capsules, syrups and elixirs, in liquid forms for injectable products, and topically as ointments, creams or lotions. Specification 850,833 is referred to.
GB37877/58A 1957-11-29 1958-11-25 Improvements in or relating to steroids and the manufacture thereof Expired GB872112A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US872112XA 1957-11-29 1957-11-29

Publications (1)

Publication Number Publication Date
GB872112A true GB872112A (en) 1961-07-05

Family

ID=22203756

Family Applications (1)

Application Number Title Priority Date Filing Date
GB37877/58A Expired GB872112A (en) 1957-11-29 1958-11-25 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB872112A (en)

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