NL960029I2 - Esters of an androstane-17-beta-carbothioic acid, process for the preparation of these esters, and pharmaceutical preparations containing these esters. - Google Patents

Esters of an androstane-17-beta-carbothioic acid, process for the preparation of these esters, and pharmaceutical preparations containing these esters.

Info

Publication number
NL960029I2
NL960029I2 NL960029C NL960029C NL960029I2 NL 960029 I2 NL960029 I2 NL 960029I2 NL 960029 C NL960029 C NL 960029C NL 960029 C NL960029 C NL 960029C NL 960029 I2 NL960029 I2 NL 960029I2
Authority
NL
Netherlands
Prior art keywords
esters
group
alpha
compounds
androstane
Prior art date
Application number
NL960029C
Other languages
Dutch (nl)
Other versions
NL960029I1 (en
Original Assignee
Glaxo Group 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 Group Ltd filed Critical Glaxo Group Ltd
Publication of NL960029I1 publication Critical patent/NL960029I1/en
Publication of NL960029I2 publication Critical patent/NL960029I2/en

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
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/0026—Oxygen-containing hetero ring cyclic ketals
    • C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0038—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an androstane skeleton, including 18- or 19-substituted derivatives, 18-nor derivatives and also derivatives where position 17-beta is substituted by a carbon atom not directly bonded to a further carbon atom and not being part of an amide group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes
    • C07J71/0015—Oxiranes at position 9(11)
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Compounds of the formula <IMAGE> in which R<1> is a fluoro-, chloro- or bromomethyl group or a 2'-fluoroethyl group, R<2> is a group COR<6> in which R<6> is a C1-3-alkyl group, or OR<2> and R<3> together form a 16 alpha ,17 alpha -isopropylidenedioxy group; R<3> is a hydrogen atom, a methyl group (which can be present in either the alpha or the ss configuration) or a methylene group; R<4> is a hydrogen, chlorine or fluorine atom; R<5> is a hydrogen or fluorine atom, and the symbol ..... is a single or double bond. The compounds have good anti-inflammatory activity, in particular on topical application. The compounds of the formula I are prepared by esterification, halogenation, reduction, elimination of protective groups and reaction at a 9,11 double bond to form a 9 alpha -halo-11ss-hydroxy group.
NL960029C 1980-02-15 1996-10-29 Esters of an androstane-17-beta-carbothioic acid, process for the preparation of these esters, and pharmaceutical preparations containing these esters. NL960029I2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8005174 1980-02-15
GB8013339 1980-04-23

Publications (2)

Publication Number Publication Date
NL960029I1 NL960029I1 (en) 1997-02-03
NL960029I2 true NL960029I2 (en) 1997-04-01

Family

ID=26274505

Family Applications (2)

Application Number Title Priority Date Filing Date
NL8100707A NL191792C (en) 1980-02-15 1981-02-13 Esters of an androstane-17beta-carbothioic acid, process for the preparation of these esters, and pharmaceutical preparations containing these esters.
NL960029C NL960029I2 (en) 1980-02-15 1996-10-29 Esters of an androstane-17-beta-carbothioic acid, process for the preparation of these esters, and pharmaceutical preparations containing these esters.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
NL8100707A NL191792C (en) 1980-02-15 1981-02-13 Esters of an androstane-17beta-carbothioic acid, process for the preparation of these esters, and pharmaceutical preparations containing these esters.

Country Status (23)

Country Link
KR (1) KR850000969B1 (en)
AT (1) AT395427B (en)
AU (1) AU544517B2 (en)
BG (1) BG60700B2 (en)
CH (2) CH644615A5 (en)
CZ (1) CZ281275B6 (en)
DE (2) DE3105307A1 (en)
DK (1) DK147022C (en)
ES (5) ES499394A0 (en)
FI (1) FI70904C (en)
FR (2) FR2477156A1 (en)
HK (1) HK58385A (en)
IE (1) IE51394B1 (en)
IT (1) IT1170717B (en)
KE (1) KE3526A (en)
MX (1) MX9202717A (en)
MY (1) MY8500757A (en)
NL (2) NL191792C (en)
NZ (1) NZ196260A (en)
PT (1) PT72502B (en)
SE (1) SE452468B (en)
SG (1) SG36885G (en)
SK (1) SK403491A3 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA817929B (en) * 1980-12-22 1982-10-27 Upjohn Co 5alpha-and 5beta-androstane-17beta-carboxylates

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1436549A (en) * 1972-06-15 1976-05-19 Glaxo Lab Ltd 17beta-mercaptocarbonyl-3alpha-hydroxy-steroids and their esters
GB1438940A (en) * 1972-07-19 1976-06-09 Glaxo Lab Ltd 17beta-haloalkoxycarbonyl-17alpha-oxysteroids
GB1514476A (en) * 1974-08-30 1978-06-14 Glaxo Lab Ltd Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates
US4188385A (en) * 1978-04-05 1980-02-12 Syntex (U.S.A.) Inc. Thioetianic acid derivatives
GB1580517A (en) * 1978-04-06 1980-12-03 Fowler I Crutches

Also Published As

Publication number Publication date
SG36885G (en) 1985-11-15
NZ196260A (en) 1983-11-30
MY8500757A (en) 1985-12-31
ATA67481A (en) 1992-05-15
NL191792B (en) 1996-04-01
SK278140B6 (en) 1996-02-07
CZ281275B6 (en) 1996-08-14
DK147022B (en) 1984-03-19
NL191792C (en) 1996-08-02
ES524985A0 (en) 1985-01-01
KE3526A (en) 1985-06-07
DE3105307C2 (en) 1988-09-29
CH644615A5 (en) 1984-08-15
DE3153379C2 (en) 1992-11-19
CZ403491A3 (en) 1994-03-16
PT72502A (en) 1981-03-01
KR830005262A (en) 1983-08-03
MX9202717A (en) 1992-06-30
IE810282L (en) 1981-08-15
FR2485542A1 (en) 1981-12-31
ES8305379A1 (en) 1983-04-01
DK62381A (en) 1981-08-16
IT8147792A0 (en) 1981-02-13
FI70904B (en) 1986-07-18
FI70904C (en) 1986-10-27
ES518161A0 (en) 1984-01-16
SK403491A3 (en) 1996-02-07
ES8207194A1 (en) 1982-09-01
ES8600936A1 (en) 1985-10-16
ES532055A0 (en) 1985-10-16
PT72502B (en) 1982-02-05
AU6729881A (en) 1981-08-20
IE51394B1 (en) 1986-12-24
ES509539A0 (en) 1983-04-01
NL960029I1 (en) 1997-02-03
ES8502447A1 (en) 1985-01-01
CH651307A5 (en) 1985-09-13
AU544517B2 (en) 1985-06-06
ES499394A0 (en) 1982-09-01
NL8100707A (en) 1981-09-16
FR2477156A1 (en) 1981-09-04
KR850000969B1 (en) 1985-07-02
SE452468B (en) 1987-11-30
DK147022C (en) 1984-08-27
BG60700B2 (en) 1995-12-29
ES8402317A1 (en) 1984-01-16
DE3105307A1 (en) 1981-12-10
IT1170717B (en) 1987-06-03
FR2477156B1 (en) 1984-11-16
HK58385A (en) 1985-08-16
SE8101010L (en) 1981-08-16
FR2485542B1 (en) 1983-06-10
AT395427B (en) 1992-12-28
FI810444L (en) 1981-08-16

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