GB1317185A - Acyloxy-3alpha-hydroxy-pregnones - Google Patents

Acyloxy-3alpha-hydroxy-pregnones

Info

Publication number
GB1317185A
GB1317185A GB3316272A GB1317185DA GB1317185A GB 1317185 A GB1317185 A GB 1317185A GB 3316272 A GB3316272 A GB 3316272A GB 1317185D A GB1317185D A GB 1317185DA GB 1317185 A GB1317185 A GB 1317185A
Authority
GB
United Kingdom
Prior art keywords
dione
pregnane
pregnan
hydroxy
acyloxy
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
GB3316272A
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.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo Laboratories Ltd
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 Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Publication of GB1317185A publication Critical patent/GB1317185A/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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

1317185 21 - Acyloxy - 3α - hydroxy - 5α- pregnane-11,20-diones GLAXO LABORATORIES Ltd 11 June 1970 [20 June 1969] 33162/72 Divided out of 1317184 Heading C2U [Also in Division C3] Novel steroids of the formula (wherein R is optionally substituted alkanoyl, aroyl or aralkanoyl) are prepared (i) by reacting lead tetraacylates with 3α-hydroxy-5α-pregnane-11,20-dione in which the OH group may be protected; (ii) by reduction of a 21-acyloxy- 5α - pregnane - 3,11,20 - trione, e.g. using Saccharomyces cerevisiae; (iii) by reacting 21- halo - 5α - pregnan - 3α - ol - 11,20 - diones (prepared by halogenation of the 21-unsubstituted compound) with a salt of the appropriate acid; or (iv) by hydrolysing a product of (i) above containing a protected 3-hydroxy group to the corresponding 21 -ol, acylating this and removing the protecting group. 3α - Trimethylsilyloxy - 5α - pregnane - 11,20- dione and 3α - (2,2,2 - trichloroethoxycarbonyloxy)-5α-pregnane-11,20-dione are prepared from the 3a-ol and trimethylchlorosilane and 2,2,2- trichloroethyl chloroformate respectively. They are subsequently converted to their 21-acetoxy derivatives as described in (i) above. 17a - Bromo - 5α - pregnan - 3α - ol - 11,20- dione is a by-product in the 21-bromination of 5α-pregnan-3α-ol-11,20-dione. Specified intermediates in process (iv) are 21 - acetoxy - 5α - pregnan - 3α - ol - 11,20 - dione 3-nitrate and the corresponding 21-isobutyryloxy and hemisuccinoyloxy compounds and 5α-pregnane - 3α, 21 - diol - 11,20 - dione 3 - nitrate.
GB3316272A 1969-06-20 1969-06-20 Acyloxy-3alpha-hydroxy-pregnones Expired GB1317185A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3316272 1969-06-20

Publications (1)

Publication Number Publication Date
GB1317185A true GB1317185A (en) 1973-05-16

Family

ID=10349353

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3316272A Expired GB1317185A (en) 1969-06-20 1969-06-20 Acyloxy-3alpha-hydroxy-pregnones

Country Status (1)

Country Link
GB (1) GB1317185A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997007807A1 (en) * 1995-08-23 1997-03-06 Colin Stanley Goodchild New use of pregnane-diones as analgesic agents
EP0827505A1 (en) * 1995-04-05 1998-03-11 Cephalon, Inc. Selected soluble esters of hydroxyl-containing indolocarbazoles
US6787530B1 (en) 1996-08-23 2004-09-07 Monash University Use of pregnane-diones as analgesic agents

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0827505A1 (en) * 1995-04-05 1998-03-11 Cephalon, Inc. Selected soluble esters of hydroxyl-containing indolocarbazoles
EP0827505A4 (en) * 1995-04-05 1998-08-12 Cephalon Inc Selected soluble esters of hydroxyl-containing indolocarbazoles
WO1997007807A1 (en) * 1995-08-23 1997-03-06 Colin Stanley Goodchild New use of pregnane-diones as analgesic agents
US6787530B1 (en) 1996-08-23 2004-09-07 Monash University Use of pregnane-diones as analgesic agents

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Legal Events

Date Code Title Description
PS Patent sealed
429A Application made for amendment of specification (sect. 29/1949)
429H Application (made) for amendment of specification now open to opposition (sect. 29/1949)
429D Case decided by the comptroller ** specification amended (sect. 29/1949)
PCNP Patent ceased through non-payment of renewal fee