GB863489A - 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
GB863489A
GB863489A GB22821/57A GB2282157A GB863489A GB 863489 A GB863489 A GB 863489A GB 22821/57 A GB22821/57 A GB 22821/57A GB 2282157 A GB2282157 A GB 2282157A GB 863489 A GB863489 A GB 863489A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
tetrahydroxy
etherified
glycol
containing less
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
GB22821/57A
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 GB863489A publication Critical patent/GB863489A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J5/00Normal 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J75/00Processes 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: (a) compounds of the general formula: <FORM:0863489/IV (b)/1> wherein R1O. AcO and -O-R2-O- represent respectively hydrocarbonoxy, hydrocarboyloxy and hydrocarbon a , b -glycol radicals, each containing less than 12 carbon atoms; (b) a process for producing 19-norhydrocortisone comprising reducing a 3-etherified 3, 11b , 17a , 21-tetrahydroxy-19-nor- 1, 3, 5(10)-pregnatiren-20-one 20-cyclic ketal (II, wherein R1O represents any ether radical containing less than 12 carbon atoms and -O-R2-O- the radical of any glycol having less than 2 carbon atoms between the carbinol groups and containing less than 12 carbon atoms) by means of lithium, an alcohol and liquid ammonia, to produce a 3-etherified 3-, 11b , 17a , 21-tetrahydroxy-19-nor-2, 5(10)- pregnadien-20-one 20-cyclic ketal (III, wherein R1O and -O-R2-O- have the meanings given immediately above), and heating the latter compound with an acid hydrolysing agent; (c) the combination of process (b) with the preparation of the starting materials by heating an appropriate 3-etherified 3, 11b , 17a , 21-tetrahydroxy-19-nor-1, 3, 5(10)-pregnatrien-20-one (I) or an 11b -acyl derivative thereof (Ia) with an appropriate glycol and an acid catalyst, followed, in the case of the 11b -acyloxy compound, by reductive hydrolysis with a metal hydride. Specification 863,313 is referred to.
GB22821/57A 1956-08-21 1957-07-18 Improvements in or relating to steroids and the manufacture thereof Expired GB863489A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US863489XA 1956-08-21 1956-08-21

Publications (1)

Publication Number Publication Date
GB863489A true GB863489A (en) 1961-03-22

Family

ID=22197997

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22821/57A Expired GB863489A (en) 1956-08-21 1957-07-18 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB863489A (en)

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