GB868374A - 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
GB868374A
GB868374A GB1481/58A GB148158A GB868374A GB 868374 A GB868374 A GB 868374A GB 1481/58 A GB1481/58 A GB 1481/58A GB 148158 A GB148158 A GB 148158A GB 868374 A GB868374 A GB 868374A
Authority
GB
United Kingdom
Prior art keywords
androstene
trihydroxy
dihydroxy
diacylate
acylate
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
GB1481/58A
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 GB868374A publication Critical patent/GB868374A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • 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 a compound selected from the group consisting of 3b , 11b , 17b -trihydroxy-5-androstene, 3b , 11b , 17b -trihydroxy-5-androstene-11b -acylate, 3b , 11b , 17b -trihydroxy-5-androstene-3b , 17b -diacylate, 3b , 11b , 17b -trihydroxy-5-androstene-3b , 11b , 17b -triacylate, 3b , 17b -dihydroxy-5-androsten11-one and 3b , 17b -dihydroxy-5-androsten-11-one-diacylate wherein the acyl group of the acylate is of a hydrocarbon carboxylic acid containing from 1-9 carbon atoms inclusive and a process for the production of 3b , 11b , 17b -trihydroxy-5-androstene by treating a 3, 11b -dihydroxy-3,5-androstadien-17-one 3,11-diacylate wherein the acyl group is of a hydrocarbon carboxylic acid containing 1-9 carbon atoms inclusive with an alkali metal borohydride to obtain the corresponding 3, 11b , 17b -trihydroxy-5-androstene-11b -acylate and hydrolysing the thus-obtained 11b -acylate with lithium aluminium hydride to obtain 3b , 11b , 17b -trihydroxy-5-androstene. Subsequently the 3b , 11b , 17b -trihydroxy-5-androsten-3-one may be esterified to produce a 3, 17b -diester which is oxidised to the corresponding 3b , 17b -dihydroxy-5-androsten-11-one 3b , 17b -diacylate. As alkali metal borohydrides there may be used sodium potassium or lithium borohydrides. As acylating agents there may be used anhydrides, chlorides or bromides of organic carboxylic acids. Examples describe the production of the compounds listed above.ALSO:A pharmaceutical composition comprises 3b , 11b , 17b - trihydroxy - 5 - androstene, the 11b -acylate, the 3b , 17b -diacylate, and the triacylate thereof, or 3b , 17b -dihydroxy-5-androsten-11-one and its diesters and a pharmaceutical diluent. They can be used orally as anaesthetics together with hexobarbitol sodium. They can be given as injectables in oil suspensions, as water-soluble sodium salts or amine salts of dibasic acid acylates, e.g. hemisuccinates. Other compounds useful for intramuscular injection are the di- and tri-esters of 3b , 11b , 17b - trihydroxy - 5 - androstene and diesters of 3b , 17b - dihydroxy - 5 - androstene - 11-one, e.g. acetates, propionates, cyclopentyl-propionates, benzoates, phenylacetates and di-methylglutarates.
GB1481/58A 1957-02-14 1958-01-15 Improvements in or relating to steroids and the manufacture thereof Expired GB868374A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US868374XA 1957-02-14 1957-02-14

Publications (1)

Publication Number Publication Date
GB868374A true GB868374A (en) 1961-05-17

Family

ID=22201236

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1481/58A Expired GB868374A (en) 1957-02-14 1958-01-15 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB868374A (en)

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