GB809493A - 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
GB809493A
GB809493A GB12748/57A GB1274857A GB809493A GB 809493 A GB809493 A GB 809493A GB 12748/57 A GB12748/57 A GB 12748/57A GB 1274857 A GB1274857 A GB 1274857A GB 809493 A GB809493 A GB 809493A
Authority
GB
United Kingdom
Prior art keywords
pregnadiene
dione
compounds
dihydroxy
iodo
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
GB12748/57A
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 GB809493A publication Critical patent/GB809493A/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 general formula <FORM:0809493/IV (b)/1> wherein R represents a b -hydroxy or keto group, and a process which comprises esterifying 11b ,17a ,21 - trihydroxy - 1,4 - pregnadiene - 3,20-dione with methane sulphonyl chloride to obtain the 21 - methane - sulphonate of 11b ,17a ,21 - trihydroxy - 1,4 - pregnadiene - 3,20-dione, treating the thus-obtained 21-methane sulphonate with alkali metal iodide in acetone to obtain 11b ,17a -dihydroxy-21-iodo-1,4-pregnadiene-3,20-dione and treating the thus obtained iodo compound with silver fluoride in acetonitrile to obtain 11b ,17a -dihydroxy-21 - fluoro - 1,4 - pregnadiene - 3,20 - dione. The invention also comprises the intermediate 21-methanesulphonates and 21-iodo compounds and their preparation. The 11b -hydroxy compounds may be oxidized to the corresponding 11-keto compounds by means of chromic acid. The iodination step may be effected with sodium or potassium iodide and the subsequent fluorination step may be effected in hexanes, heptanes, benzene or t-butyl alcohol. Examples describe the preparation of 1-dehydro-hydrocortisone 21-methanesulphonate, 11b ,17a -dihydroxy - 21 - iodo - 1,4 - pregnadiene - 3,20 - dione, 11b ,17a - dihydroxy - 21 - fluoro - 1,4 - pregnadiene - 3,20 - dione, and the corresponding 11-keto compounds.
GB12748/57A 1956-05-04 1957-04-18 Improvements in or relating to steroids and the manufacture thereof Expired GB809493A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US809493XA 1956-05-04 1956-05-04

Publications (1)

Publication Number Publication Date
GB809493A true GB809493A (en) 1959-02-25

Family

ID=22160696

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12748/57A Expired GB809493A (en) 1956-05-04 1957-04-18 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB809493A (en)

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