GB1514476A - Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates - Google Patents

Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates

Info

Publication number
GB1514476A
GB1514476A GB38090/74A GB3809074A GB1514476A GB 1514476 A GB1514476 A GB 1514476A GB 38090/74 A GB38090/74 A GB 38090/74A GB 3809074 A GB3809074 A GB 3809074A GB 1514476 A GB1514476 A GB 1514476A
Authority
GB
United Kingdom
Prior art keywords
compounds
formula
steroids
radical
alpha
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
GB38090/74A
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
Priority to GB38090/74A priority Critical patent/GB1514476A/en
Priority to SE7509651A priority patent/SE405976B/en
Priority to FR7526651A priority patent/FR2282899A1/en
Priority to IE1904/75A priority patent/IE41663B1/en
Priority to ZA00755553A priority patent/ZA755553B/en
Priority to BE159583A priority patent/BE832889A/en
Priority to JP50104825A priority patent/JPS5148649A/ja
Priority to DK389175AA priority patent/DK136074B/en
Priority to CH1120375A priority patent/CH612686A5/en
Priority to AU84404/75A priority patent/AU492497B2/en
Priority to NL7510226A priority patent/NL7510226A/en
Priority to DE19752538595 priority patent/DE2538595A1/en
Priority to US05/757,325 priority patent/US4093721A/en
Publication of GB1514476A publication Critical patent/GB1514476A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
    • C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

Steroids with antiinflammatory activity and the formula I in which R' is methyl, ethyl, n-propyl or isopropyl; R'' is methyl, chloromethyl, fluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl or 2-iodoethyl; X is hydrogen or fluorine; and @ is a single or double bond are prepared by esterifying or transesterifying, respectively, with an agent supplying the radical R'' or the radical R', respectively, a corresponding 17 alpha -acyloxy-17ss-carboxylic acid or a functional derivative thereof or a 17 alpha -hydroxy-17ss-carboxylate. Resulting DELTA <1>-steroids of the formula I can subsequently be reduced to the corresponding saturated compounds or resulting 1,2-saturated compounds can be dehydrogenated to the corresponding DELTA <1> compounds. In addition, halogen substituents present in the group R'' can be replaced by other halogens; thus, for example, compounds of the formula I in which R'' is an alkyl group substituted by chlorine, bromine or iodine can be converted by this exchange reaction to the corresponding fluoroalkyl compounds. The compounds of the formula I are distinguished by very good antiinflammatory activity and can be converted into pharmaceuticals for topical or internal administration. <IMAGE>
GB38090/74A 1974-08-30 1974-08-30 Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates Expired GB1514476A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
GB38090/74A GB1514476A (en) 1974-08-30 1974-08-30 Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates
SE7509651A SE405976B (en) 1974-08-30 1975-08-29 PROCEDURE FOR THE PRODUCTION OF ANTI-INFLAMMATORY STEROIDS BELONGING TO THE ANDROSTAN SERIES
FR7526651A FR2282899A1 (en) 1974-08-30 1975-08-29 ANDROSTANE SERIES STEROIDS, THEIR PREPARATION AND THEIR APPLICATIONS
IE1904/75A IE41663B1 (en) 1974-08-30 1975-08-29 Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene17-carboxylates
ZA00755553A ZA755553B (en) 1974-08-30 1975-08-29 Anti-inflammatory steroids of the androstane series
BE159583A BE832889A (en) 1974-08-30 1975-08-29 ANDROSTANE SERIES STEROIDS AND THEIR PREPARATION
JP50104825A JPS5148649A (en) 1974-08-30 1975-08-29
DK389175AA DK136074B (en) 1974-08-30 1975-08-29 Analogous process for the preparation of 6alpha-fluoro-11beta-hydroxy-16-methyl-3-oxo-17alpha-acyloxyandrost-4-ene-17beta-carboxylic acid esters.
CH1120375A CH612686A5 (en) 1974-08-30 1975-08-29 Process for the preparation of steroids of the androstane series
AU84404/75A AU492497B2 (en) 1975-08-29 Alkyl and haloalkyl androst-4-ene and androsta-1, 4-diene-17-carboxylates
NL7510226A NL7510226A (en) 1974-08-30 1975-08-29 PROCESS FOR THE PREPARATION OF ANDROSTA DERIVATIVES.
DE19752538595 DE2538595A1 (en) 1974-08-30 1975-08-29 STEROID CONNECTIONS
US05/757,325 US4093721A (en) 1974-08-30 1977-01-06 Pharmaceutical compositions of 6α,9α-difluoro-androst-4-ene-17β-carboxylates and derivatives thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB38090/74A GB1514476A (en) 1974-08-30 1974-08-30 Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates

Publications (1)

Publication Number Publication Date
GB1514476A true GB1514476A (en) 1978-06-14

Family

ID=10401112

Family Applications (1)

Application Number Title Priority Date Filing Date
GB38090/74A Expired GB1514476A (en) 1974-08-30 1974-08-30 Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates

Country Status (11)

Country Link
JP (1) JPS5148649A (en)
BE (1) BE832889A (en)
CH (1) CH612686A5 (en)
DE (1) DE2538595A1 (en)
DK (1) DK136074B (en)
FR (1) FR2282899A1 (en)
GB (1) GB1514476A (en)
IE (1) IE41663B1 (en)
NL (1) NL7510226A (en)
SE (1) SE405976B (en)
ZA (1) ZA755553B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003062259A2 (en) * 2002-01-21 2003-07-31 Glaxo Group Limited Non-aromatic 17.alpha.-esters of androstane-17.beta.-carboxylate esters as anti-inflammatory agents
WO2003072592A1 (en) * 2002-01-15 2003-09-04 Glaxo Group Limited 17.alpha-cycloalkyl/cycloylkenyl esters of alkyl-or haloalkyl-androst-4-en-3-on-11.beta.,17.alpha.-diol 17.beta.-carboxylates as anti-inflammatory agents
WO2003082896A2 (en) * 2002-03-29 2003-10-09 Farmabios S.P.A. A PROCESS FOR THE PREPARATION OF 6α-FLUORO STEROIDS BY ISOMERISATION OF 6β-FLUOROSTEROIDS
WO2005005451A1 (en) 2003-07-11 2005-01-20 Glaxo Group Limited Specific glucocorticosteroid compound having anti- inflammatory activity
US7579335B2 (en) 2005-01-10 2009-08-25 Glaxo Group Limited Androstane 17α-carbonate derivatives for use in the treatment of allergic and inflammatory conditions

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH628355A5 (en) * 1976-02-24 1982-02-26 Ciba Geigy Ag METHOD FOR PRODUCING NEW ANDROSTADIEN-17BETA-CARBONIC ACIDS AND THEIR ESTERS AND SALTS.
CH614960A5 (en) * 1976-04-15 1979-12-28 Ciba Geigy Ag
DE2809491A1 (en) * 1977-03-09 1978-09-14 Ciba Geigy Ag ANTICOCCIDIELLE AND OVO-LARVICIDE MEDIUM
SE452468B (en) * 1980-02-15 1987-11-30 Glaxo Group Ltd ANDROSTAN CARBATIOTS, PROCEDURE FOR PREPARING THESE AND COMPOSITIONS
SE449106B (en) * 1980-07-10 1987-04-06 Otsuka Pharma Co Ltd STEROID WITH ANTI-INFLAMMATORY EFFECT AND COMPOSITION CONTAINING THIS
US4607028A (en) * 1983-08-18 1986-08-19 Ciba-Geigy Corporation Novel carboxylic acid esters

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3636010A (en) * 1968-12-23 1972-01-18 Ciba Geigy Corp Esters of steroid-17-carboxylic acids
GB1384372A (en) * 1971-01-20 1975-02-19 Glaxo Lab Ltd Dereivatives of 17alpha-hydroxyandrost-4-ene-17beta-carboxylic acids
GB1438940A (en) * 1972-07-19 1976-06-09 Glaxo Lab Ltd 17beta-haloalkoxycarbonyl-17alpha-oxysteroids

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003072592A1 (en) * 2002-01-15 2003-09-04 Glaxo Group Limited 17.alpha-cycloalkyl/cycloylkenyl esters of alkyl-or haloalkyl-androst-4-en-3-on-11.beta.,17.alpha.-diol 17.beta.-carboxylates as anti-inflammatory agents
WO2003062259A2 (en) * 2002-01-21 2003-07-31 Glaxo Group Limited Non-aromatic 17.alpha.-esters of androstane-17.beta.-carboxylate esters as anti-inflammatory agents
WO2003062259A3 (en) * 2002-01-21 2003-08-28 Glaxo Group Ltd Non-aromatic 17.alpha.-esters of androstane-17.beta.-carboxylate esters as anti-inflammatory agents
WO2003082896A2 (en) * 2002-03-29 2003-10-09 Farmabios S.P.A. A PROCESS FOR THE PREPARATION OF 6α-FLUORO STEROIDS BY ISOMERISATION OF 6β-FLUOROSTEROIDS
WO2003082896A3 (en) * 2002-03-29 2003-11-20 Farmabios Srl A PROCESS FOR THE PREPARATION OF 6α-FLUORO STEROIDS BY ISOMERISATION OF 6β-FLUOROSTEROIDS
US7291609B2 (en) 2003-07-11 2007-11-06 Glaxo Group Limited Specific glucocorticosteroid compound having anti-inflammatory activity
WO2005005452A1 (en) 2003-07-11 2005-01-20 Glaxo Group Limited Specific glucocorticosteroid compound having anti- inflammatory activity
US7288536B2 (en) 2003-07-11 2007-10-30 Glaxo Group Limited Specific glucocorticosteroid compound having anti-inflammatory activity
WO2005005451A1 (en) 2003-07-11 2005-01-20 Glaxo Group Limited Specific glucocorticosteroid compound having anti- inflammatory activity
JP2009513533A (en) * 2003-07-11 2009-04-02 グラクソ グループ リミテッド Certain glucocorticosteroid compounds with anti-inflammatory activity
JP2009514781A (en) * 2003-07-11 2009-04-09 グラクソ グループ リミテッド Certain glucocorticosteroid compounds with anti-inflammatory activity
US7524970B2 (en) 2003-07-11 2009-04-28 Glaxo Group Limited Compounds
AU2004255855B2 (en) * 2003-07-11 2009-07-30 Glaxo Group Limited Specific glucocorticosteroid compound having anti- inflammatory activity
AU2004255854B2 (en) * 2003-07-11 2009-10-22 Glaxo Group Limited Specific glucocorticosteroid compound having anti- inflammatory activity
US7638508B2 (en) 2003-07-11 2009-12-29 Glaxo Group Limited Glucocorticosteroid compound having anti-inflammatory activity
KR101029207B1 (en) 2003-07-11 2011-04-12 글락소 그룹 리미티드 Specific glucocorticosteroid compound having anti-inflammatory activity
KR101075324B1 (en) 2003-07-11 2011-10-19 글락소 그룹 리미티드 Specific glucocorticosteroid compound having anti-inflammatory activity
US7579335B2 (en) 2005-01-10 2009-08-25 Glaxo Group Limited Androstane 17α-carbonate derivatives for use in the treatment of allergic and inflammatory conditions

Also Published As

Publication number Publication date
JPS5148649A (en) 1976-04-26
AU8440475A (en) 1977-03-03
DK136074C (en) 1978-01-16
FR2282899B1 (en) 1978-11-10
IE41663B1 (en) 1980-02-27
NL7510226A (en) 1976-03-02
BE832889A (en) 1976-03-01
DK389175A (en) 1976-03-01
IE41663L (en) 1976-02-29
ZA755553B (en) 1976-09-29
CH612686A5 (en) 1979-08-15
FR2282899A1 (en) 1976-03-26
DK136074B (en) 1977-08-08
DE2538595A1 (en) 1976-03-11
SE7509651L (en) 1976-03-01
SE405976B (en) 1979-01-15

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee