GB1007756A - New 19-hydroxy-steroids - Google Patents

New 19-hydroxy-steroids

Info

Publication number
GB1007756A
GB1007756A GB2672062A GB2672062A GB1007756A GB 1007756 A GB1007756 A GB 1007756A GB 2672062 A GB2672062 A GB 2672062A GB 2672062 A GB2672062 A GB 2672062A GB 1007756 A GB1007756 A GB 1007756A
Authority
GB
United Kingdom
Prior art keywords
oxo
acetoxy
oxido
caproyloxy
pregnane
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
GB2672062A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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
Priority claimed from CH826961A external-priority patent/CH448074A/en
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB1007756A publication Critical patent/GB1007756A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • 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
    • 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
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • 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 D 4,6-3-oxo-19-hydroxy-steroids and their 19-esters, and their preparation in which a D 4-3-oxo-6BETA,19-oxido-steroid is treated in an anhydrous medium and in the presence of a strongly acidic catalyst with either an acylating agent to form the 19-ester or with a reactive functional derivative of a lower aliphatic, araliphatic or heterocyclic alcohol to form a 3-enol ether, any enol ether formed is split by treatment with an aqueous acid, if desired, any complex with the catalyst formed is split with an alkaline agent and/or any 2-acyl compound obtained is converted into the corresponding 2-unsubstituted compound by means of an acidic or alkaline agent and/or any D 4,6-3-oxo-19-acyloxy-steroid obtained is hydrolysed or hydrogenolysed to the corresponding 19-ol. The steroids may be of the androstane, pregnane, cholane, cholestane, spirostane or cardanolide series and may contain free, ketalized or enolized oxo groups, free, esterified or etherified hydroxyl groups, alkyl, alkenyl or alkyryl groups and halogen atoms in one or more of positions 1, 2, 7, 8, 9, 11, 12, 14, 15, 16, 17, 20 and 21. They may also contain additional double bonds. The strongly acidic catalyst may be a concentrated mineral or sulphonic acid or a Lewis acid, particularly boron trifluoride, and complexes of this last named compound with D 4,6-2-acetyl-3-oxo-19-acetoxy-pregnadi nes and androstadienes are described and claimed. Suitable acylating agents are anhydrides and halides of lower aliphatic carboxylic acids, and formic acid or mixed anhydrides thereof, and suitable enol-ether-forming reagents are alkyl esters of aliphatic ortho-carboxylic acids. Examples are given, an intermediate in the reaction of D 4-3-oxo - 6BETA,19 - oxido - 17b - acetoxy - androstene with methyl orthoformate being 3,3,5-trimethoxy - 6b ,19 - oxido - 17b - acetoxy - androstane. D 4 - 3,20 - dioxo - 17a - caproyloxy 6b ,19-oxido-pregnene is prepared by preparing D 5-3b -acetoxy - 17a - caproyloxy - 20 - oxo - pregnane from the 17a -ol, converting this to 3b -acetoxy-5a -chloro - 6b - hydroxy - 17a - caproyloxy 20 - oxo - pregnene, converting this to 3b -acetoxy-5a -chloro - 17a - caproyloxy - 20 - oxo - 6b ,19 - oxido-pregnane, hydrolysing this to the 3b -ol, and oxidizing and dehydrochlorinating this. Specifications 994,746, 994,748 and 1,007,757 are referred to.
GB2672062A 1961-07-14 1962-07-11 New 19-hydroxy-steroids Expired GB1007756A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH826961A CH448074A (en) 1961-07-14 1961-07-14 Process for the preparation of new 19-hydroxysteroids
CH1516861 1961-12-29

Publications (1)

Publication Number Publication Date
GB1007756A true GB1007756A (en) 1965-10-22

Family

ID=25703091

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2672062A Expired GB1007756A (en) 1961-07-14 1962-07-11 New 19-hydroxy-steroids

Country Status (4)

Country Link
AT (1) AT248626B (en)
DK (1) DK108858C (en)
GB (1) GB1007756A (en)
SE (1) SE306733B (en)

Also Published As

Publication number Publication date
AT248626B (en) 1966-08-10
SE306733B (en) 1968-12-09
DK108858C (en) 1968-02-19

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