GB863782A - 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
GB863782A
GB863782A GB26722/57A GB2672257A GB863782A GB 863782 A GB863782 A GB 863782A GB 26722/57 A GB26722/57 A GB 26722/57A GB 2672257 A GB2672257 A GB 2672257A GB 863782 A GB863782 A GB 863782A
Authority
GB
United Kingdom
Prior art keywords
dione
pregnene
alkyl
aryl
fluoro
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
GB26722/57A
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 GB863782A publication Critical patent/GB863782A/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)

Abstract

The invention comprises compounds having the formula: <FORM:0863782/IV (b)/1> <FORM:0863782/IV (b)/2> wherein R is an 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, a 6a -alkyl or 6a -aryl-17a -hydroxy-21-fluoro-4, 9(11)-pregnadiene-3, 20-dione, a 6a -alkyl or 6a -aryl-9b , 11b -oxido-17a -hydroxy-21-fluoro-4-pregnene-3, 20-dione and a 6a -alkyl or 6a -aryl-9a -fluoro-11b , 17a -dihydroxy-21-iodo-4-pregnene-3, 20-dione and a process which comprises dehydrating the corresponding 6-alkyl or 6-aryl-11b , 17a -dihydroxy-21-fluoro-4-pregnene-3, 20-dione to obtain the corresponding 6-alkyl or 6-aryl-17a -hydroxy-21-fluoro-4 9(11) -pregnadiene-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-4-pregnene-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-4-pregnene-3, 20-dione, which is treated with hydrogen fluoride to obtain 6-alkyl to 6-aryl-9a , 12-difluoro-11b , 17a -dihydroxy-4-pregnene-3, 20-dione. Oxidation of this compound gives 6-alkyl or 6-aryl-9a , 21-difluoro-11b , 17a -dihydroxy-4-pregnene-3, 20-dione. Alternatively 6-alkyl or 6-aryl-9a -fluorohydrocortisone is treated with an organic sulphonyl halide to obtain the corresponding 21-organic sulphonate which on treatment with sodium iodide gives 6-alkyl or 6-aryl-9a -fluoro-11b , 17a -dihydroxy-21-iodo-4-pregnene-3, 20-dione and treating this compound with silver fluoride to obtain 6-alkyl or 6-aryl-9a , 21,difluoro-11b , 17a -dihydroxy-4-pregnene-3, 20-dione. Illustrative products of the invention are 6a -methyl-17a -hydroxy-21-fluoro-4, 9(11)-pregnadiene-3, 20-dione, 6a -methyl-9a -halo-11b , 17a -dihydroxy-21-fluoro-4-pregnene-3, 20-dione, 6a -methyl-9b , 11b -oxido-17a -hydroxy-21-fluoro-4-pregnene-3, 20-dione, 6a -methyl-9a , 21-difluoro-11b , 17a -dihydroxy-4-pregnene-3, 20-dione, 6a -methyl-9a , 21-difluoro-17a -hydroxy-4-pregnene-3, 11, 20-trione, and 6a -methyl-9a -fluoro-11b , 17a , 21-trihydroxy-21-iodo-4-pregnene-3, 20-dione. Specifications 861,471 and 863,779 are referred to.ALSO:Pharmaceutical compositions comprise compounds having the formula <FORM:0863782/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 or tablets, ointments, lotions, jellies, creams, suppositories, bougies and aqueous suspensions. An example employs 6a -methyl-9a ,21 - difluoro - 11b ,17a - dihydroxy - 4 - pregnene-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 chloramphenicol, or a sulphonamide. Specifications 861,471 and 863,779 are referred to.
GB26722/57A 1956-09-10 1957-08-23 Improvements in or relating to steroids and the manufacture thereof Expired GB863782A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US863782XA 1956-09-10 1956-09-10

Publications (1)

Publication Number Publication Date
GB863782A true GB863782A (en) 1961-03-29

Family

ID=22198172

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26722/57A Expired GB863782A (en) 1956-09-10 1957-08-23 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB863782A (en)

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