GB1268424A - Indolizine derivatives - Google Patents

Indolizine derivatives

Info

Publication number
GB1268424A
GB1268424A GB48856/69A GB4885669A GB1268424A GB 1268424 A GB1268424 A GB 1268424A GB 48856/69 A GB48856/69 A GB 48856/69A GB 4885669 A GB4885669 A GB 4885669A GB 1268424 A GB1268424 A GB 1268424A
Authority
GB
United Kingdom
Prior art keywords
esters
reacting
give
compounds
carbethoxyalkyl
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
GB48856/69A
Inventor
Allan Guildford Brown
John Herbert Charles Nayler
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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 Beecham Group PLC filed Critical Beecham Group PLC
Priority to GB48856/69A priority Critical patent/GB1268424A/en
Priority to IE1167/70A priority patent/IE34591B1/en
Priority to NL7013584A priority patent/NL7013584A/xx
Priority to AU19894/70A priority patent/AU1989470A/en
Priority to ZA706287A priority patent/ZA706287B/en
Priority to IL35289A priority patent/IL35289A0/en
Priority to DE19702046904 priority patent/DE2046904A1/en
Priority to ES383992A priority patent/ES383992A1/en
Priority to AT877170A priority patent/AT295513B/en
Priority to BE70@@@@@@@@A priority patent/BE756822A/en
Priority to FR7035477A priority patent/FR2070109B1/fr
Priority to JP45087040A priority patent/JPS4910517B1/ja
Publication of GB1268424A publication Critical patent/GB1268424A/en
Priority to US00311466A priority patent/US3806513A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,268,424. Indolizine derivatives. BEECHAM GROUP Ltd. 18 Sept., 1970 [4 Oct., 1969], No. 48856/69. Heading C2C. The invention comprises compounds of formulae the pharmaceutically acceptable salts and esters of I, and the esters and salts of II, wherein R and R<SP>2</SP> are each C 1-6 alkyl, and R<SP>3</SP> is aryl or C 1-6 alkyl. These compounds are prepared by reacting 2-formylpyridine with Ph 3 P : CRCO 2 Et to give 2-(2-carbethoxyalk-1-enyl)pyridine, hydrogenating this (H 2 /Pd-C) to 2-(2-carbethoxyalkyl)pyridine, reacting with (e.g.) BrCH 2 Ac to give 1-acetonyl-2-(2-carbethoxyalkyl)pyridinium bromide which is treated with a base to give II, esterifying the latter and reacting the ester with a reactive derivative of R<SP>3</SP>CO 2 H, and optionally hydrolysing the ester of I thus obtained. Therapeutic compositions for oral or parenteral administration comprise compounds I (above), and their pharmaceutically acceptable salts and esters, which have analgesic and anti inflammatory activity.
GB48856/69A 1969-10-04 1969-10-04 Indolizine derivatives Expired GB1268424A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
GB48856/69A GB1268424A (en) 1969-10-04 1969-10-04 Indolizine derivatives
IE1167/70A IE34591B1 (en) 1969-10-04 1970-09-09 Indolizine derivatives
NL7013584A NL7013584A (en) 1969-10-04 1970-09-14
AU19894/70A AU1989470A (en) 1969-10-04 1970-09-14 Organic compounds
ZA706287A ZA706287B (en) 1969-10-04 1970-09-14 Organic compounds
IL35289A IL35289A0 (en) 1969-10-04 1970-09-14 Alpha-substituted indolizine acetic acids and their preparation
DE19702046904 DE2046904A1 (en) 1969-10-04 1970-09-23 Indocinic acids and process for their preparation
ES383992A ES383992A1 (en) 1969-10-04 1970-09-25 Indolizine derivatives
AT877170A AT295513B (en) 1969-10-04 1970-09-29 Process for the preparation of new α-substituted indolizine acetic acids and their salts and esters
BE70@@@@@@@@A BE756822A (en) 1969-10-04 1970-09-29 ORGANIC COMPOUNDS WITH ANALGESIC AND ANTI-INFLAMMATORY ACTIVITY
FR7035477A FR2070109B1 (en) 1969-10-04 1970-10-01
JP45087040A JPS4910517B1 (en) 1969-10-04 1970-10-03
US00311466A US3806513A (en) 1969-10-04 1972-12-04 Alpha-substituted indolizine propionic acid and its salts

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB48856/69A GB1268424A (en) 1969-10-04 1969-10-04 Indolizine derivatives

Publications (1)

Publication Number Publication Date
GB1268424A true GB1268424A (en) 1972-03-29

Family

ID=10450175

Family Applications (1)

Application Number Title Priority Date Filing Date
GB48856/69A Expired GB1268424A (en) 1969-10-04 1969-10-04 Indolizine derivatives

Country Status (12)

Country Link
JP (1) JPS4910517B1 (en)
AT (1) AT295513B (en)
AU (1) AU1989470A (en)
BE (1) BE756822A (en)
DE (1) DE2046904A1 (en)
ES (1) ES383992A1 (en)
FR (1) FR2070109B1 (en)
GB (1) GB1268424A (en)
IE (1) IE34591B1 (en)
IL (1) IL35289A0 (en)
NL (1) NL7013584A (en)
ZA (1) ZA706287B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0519353A2 (en) * 1991-06-17 1992-12-23 Fujisawa Pharmaceutical Co., Ltd. Indolizin derivatives, process for their preparation and pharmaceutical composition containing them
RU2120942C1 (en) * 1991-06-17 1998-10-27 Фудзисава Фармасьютикал Ко., Лтд. INDOLIZINE DERIVATIVES, METHOD OF THEIR SYNTHESIS, PHARMACEUTICAL COMPOSITION, METHOD OF INHIBITION OF ACTIVITY OF TESTOSTERONE-5α-REDUCTASE
WO2006136859A3 (en) * 2005-06-24 2007-04-05 Argenta Discovery Ltd Indoli zine derivatives and their use as crth2 antagonists
WO2008074966A1 (en) * 2006-12-21 2008-06-26 Argenta Discovery Limited Crth2 antagonists

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT376677B (en) * 1979-12-06 1984-12-27 Labaz Sanofi Nv METHOD FOR PRODUCING NEW INDOLICINE DERIVATIVES AND THEIR PHARMACEUTICALLY PERMITTED ACID ADDITION SALTS
AT376676B (en) * 1979-12-06 1984-12-27 Labaz Sanofi Nv METHOD FOR PRODUCING NEW INDOLICINE DERIVATIVES AND THEIR PHARMACEUTICALLY PERMITTED ACID ADDITION SALTS

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0519353A2 (en) * 1991-06-17 1992-12-23 Fujisawa Pharmaceutical Co., Ltd. Indolizin derivatives, process for their preparation and pharmaceutical composition containing them
EP0519353A3 (en) * 1991-06-17 1993-04-14 Fujisawa Pharmaceutical Co., Ltd. Indolizin derivatives, process for their preparation and pharmaceutical composition containing them
US5334716A (en) * 1991-06-17 1994-08-02 Fujisawa Pharmaceutical Co., Ltd. Heterocyclic derivatives
RU2120942C1 (en) * 1991-06-17 1998-10-27 Фудзисава Фармасьютикал Ко., Лтд. INDOLIZINE DERIVATIVES, METHOD OF THEIR SYNTHESIS, PHARMACEUTICAL COMPOSITION, METHOD OF INHIBITION OF ACTIVITY OF TESTOSTERONE-5α-REDUCTASE
WO2006136859A3 (en) * 2005-06-24 2007-04-05 Argenta Discovery Ltd Indoli zine derivatives and their use as crth2 antagonists
WO2008074966A1 (en) * 2006-12-21 2008-06-26 Argenta Discovery Limited Crth2 antagonists

Also Published As

Publication number Publication date
ES383992A1 (en) 1973-09-01
FR2070109A1 (en) 1971-09-10
AT295513B (en) 1972-01-10
BE756822A (en) 1971-03-29
AU1989470A (en) 1972-03-16
IE34591L (en) 1971-04-04
DE2046904A1 (en) 1971-04-22
IE34591B1 (en) 1975-06-25
ZA706287B (en) 1971-06-30
IL35289A0 (en) 1970-11-30
NL7013584A (en) 1971-04-06
JPS4910517B1 (en) 1974-03-11
FR2070109B1 (en) 1974-02-01

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