GB863781A - 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
GB863781A
GB863781A GB26721/57A GB2672157A GB863781A GB 863781 A GB863781 A GB 863781A GB 26721/57 A GB26721/57 A GB 26721/57A GB 2672157 A GB2672157 A GB 2672157A GB 863781 A GB863781 A GB 863781A
Authority
GB
United Kingdom
Prior art keywords
pregnadiene
dione
alkyl
fluoro
aryl
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
GB26721/57A
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 GB863781A publication Critical patent/GB863781A/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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds having the formula: <FORM:0863781/IV (b)/1> wherein R is alkyl or aryl radical, R1 is a hydroxy or keto group and X1 is fluorine, chlorine, or bromine, and R11 is a lower alkyl radical, phenyl, tolyl, or naphthyl and a process which comprises dehydrating a 6-alkyl or aryl- 11b , 17a -dihydroxy- 21- fluoro- 1, 4-pregnadiene- 3, 20- dione with for example H2SO4 to obtain the corresponding 6-alkyl or 6-aryl-17a -hydroxy-21-fluoro-1, 4, 9(11) pregnatriene- 3, 20- dione, which is treated with hypochlorous or hypobromous acid to obtain the corresponding 6-alkyl or 6-aryl 9a -halo-11b , 17a -dihydroxy-21-fluoro-1, 4-pregnadiene-3, 20-dione, treating this compound with a mild base to obtain the corresponding 6-alkyl or 6- aryl- 9b , 11b - oxido- 17a - hydroxy-21-fluoro- 1, 4- pregnadiene- 3, 20- dione, which is treated with hydrogen fluoride to obtain 6-alkyl or aryl- 9a , 21- difluoro- 11b , 17a -dihydroxy-1, 4-pregnadiene-3, 20-dione. Oxidation of this compound gives 6-alkyl or 6- aryl- 9a , 21- difluoro- 17a - hydroxy- 1, 4-pregnadiene-3, 11, 20-trione. Alternatively 1-dehydro-6-alkyl or 6-aryl-9a -fluoro-hydrocortisone is treated with an organic sulphonyl halide to obtain the corresponding 21-organic sulphonate p which on treatment with sodium iodide gives 6-alkyl or 6-aryl-9a -fluoro-11b , 17a -dihydroxy-21-iodo-1, 4-pregnadiene-3, 20-dione and treating this compound with silver fluoride to obtain 6-alkyl- or 6-aryl-9a , 21-difluoro-11b , 17a -dihydroxy-1, 4-pregnadiene-3, 20-dione. Illustrative products of the invention are 6a -methyl-17a -hydroxy-21-fluoro-1, 4, 9(11)-pregnatriene-3, 20-dione, 6a -methyl-9a -halo-11b , 17a -dihydroxy-21-fluoro-1, 4-pregnadiene-3, 20-dione, 6a -methyl-9b , 11b oxido-17a -hydroxy-21-fluoro-1, 4-pregnadiene-3, 20-dione, 6a -methyl-9a , 21-difluoro-11b , 17a -dihydroxy-1, 4-pregnadiene-3, 20-dione, 6a -methyl-9a , 21-difluoro-17a -hydroxy-1, 4-pregnadiene-3,11,20-trione, 6a -methyl-9a -fluoro-11b , 17a , 21-trihydroxy-1, 4-pregnadiene-3, 20-dione-21-methanesulphonate, and 6a -methyl-9a -fluoro-11b ,17a -dihydroxy-21-iodo-1, 4- pregnadiene-3,20-dione. Specifications 861,471 and 863,780 are referred to.ALSO:Pharmaceutical compositions comprise compounds having the formula <FORM:0863781/VI/1> wherein R is an alkyl or aryl radical, R1 is a hydroxy or keto group and X1 is fluorine, chlorine or bromine and a pharmaceutical carrier and may take the forms of oral compositions and tablets, ointments, lotions, jellies, creams, suppositories, bougies and aqueous suspensions. An example employs 6a -methyl-9a ,21-difluoro-11b ,17a - dihydroxy - 1,4 - pregnadiene - 3,20 - dione in an ointment to which may be added an antibiotic, e.g. bacitracin, circulin, polymyxin B sulphate, gramicidin, streptomycin sulphate, dihydrostreptomycin sulphate, oxytetracycline, chlorotetracycline, tetracycline and chlormphenicol, or a sulphonamide. Specifications 861,471 and 863,780 are referred to.
GB26721/57A 1956-09-10 1957-08-23 Improvements in or relating to steroids and the manufacture thereof Expired GB863781A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US863781XA 1956-09-10 1956-09-10

Publications (1)

Publication Number Publication Date
GB863781A true GB863781A (en) 1961-03-29

Family

ID=22198171

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26721/57A Expired GB863781A (en) 1956-09-10 1957-08-23 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB863781A (en)

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