WO2004108721A1 - Procede servant a preparer 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione - Google Patents

Procede servant a preparer 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione Download PDF

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Publication number
WO2004108721A1
WO2004108721A1 PCT/IN2004/000087 IN2004000087W WO2004108721A1 WO 2004108721 A1 WO2004108721 A1 WO 2004108721A1 IN 2004000087 W IN2004000087 W IN 2004000087W WO 2004108721 A1 WO2004108721 A1 WO 2004108721A1
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WO
WIPO (PCT)
Prior art keywords
formula
compound
ethyl
ethoxy
pyridyl
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.)
Ceased
Application number
PCT/IN2004/000087
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English (en)
Inventor
Vijay Chhangamal Chhabada
Rashminkumar Rameshchandra Pandya
Rajeev Budhdev Rehani
Rajamannar Thennati
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.)
Sun Pharmaceutical Industries Ltd
Original Assignee
Sun Pharmaceutical Industries 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 Sun Pharmaceutical Industries Ltd filed Critical Sun Pharmaceutical Industries Ltd
Publication of WO2004108721A1 publication Critical patent/WO2004108721A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the process of the present invention uses environmentally friendly reaction conditions like usage of acrylamide instead of methylacrylate. Further, the process of the present invention uses the sodium salt of p-nitrophenol which is a cheaper alternative to 4-fluoronitrobenzene and sodium hydride as used herein.
  • United States patent No. 5952509 (Assignee : Takeda ; Indian Reference not available) This invention claims a reduction process for the preparation of compound of formula 1 wherein the substrate is the unsaturated precursor of compound of formula 1 viz. 5-[[4- [2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methylidene]-2,4-thiazolidinedione and the ' reducing agent is borohydride. ⁇
  • United States patent application No. 20030153765 (Inventor : Ben-Zion Dolitzky ; Indian Reference not available) carries out catalytic hydrogenation of the precursor 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methylidene]-2,4- thiazolidinedione to yield compound of formula 1.
  • the process of the present invention uses a different route to prepare compound of formula 1.
  • An object of the present invention is to provide a novel process for the preparation of 5- [[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione, compound of formula 1.
  • Another object of the present invention is to provide novel compound of formula 3 and its process of preparation.
  • the process for the preparation of compound of formula 3 comprises reacting diazonium salt of 4-[2-(5-Ethyl-2-pyridyl) ethoxy] aminobenzene, compound of formula 2, with acrylamide, aqueous HX (wherein X is Br or CI), under meerwein arylation conditions.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

Procédé servant à préparer 5-[[4-[2-(5-éthyl-2-pyridinyl)éthoxy]phényl]méthyl]-2,4-thiazolidinedione (formule 1), ce qui consiste à : a) effectuer la réaction d'un sel diazoïque d'un composé de 4-[2-(5-éthyl-2-pyridyl)éthoxy] amino-benzène, représenté par la formule (2) avec acrylamide, HX aqueux (dans laquelle X représente Br ou Cl), dans des conditions d'arylation de Meerwein, afin d'obtenir un composé représenté par la formule (3), formule (2), formule (3) (dans laquelle X représente Cl ou Br) b) effectuer la condensation du composé représenté par la formule (3) avec thiourée afin d'obtenir un composé représenté par la formule (4) ; c) convertir ce composé en un composé de la formule (1).
PCT/IN2004/000087 2003-04-01 2004-04-01 Procede servant a preparer 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione Ceased WO2004108721A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN326MU2003 2003-04-01
IN326/MUM/2003 2003-04-01

Publications (1)

Publication Number Publication Date
WO2004108721A1 true WO2004108721A1 (fr) 2004-12-16

Family

ID=33495853

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2004/000087 Ceased WO2004108721A1 (fr) 2003-04-01 2004-04-01 Procede servant a preparer 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione

Country Status (1)

Country Link
WO (1) WO2004108721A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005049532A3 (fr) * 2003-09-30 2006-04-06 Sun Pharmaceutical Ind Ltd Procede de purification
JP2010059068A (ja) * 2008-09-02 2010-03-18 Tokuyama Corp ピオグリタゾンの製造方法
JP2010208957A (ja) * 2009-03-06 2010-09-24 Tokuyama Corp 結晶構造を有する５−｛４−［２−（５−エチル−２−ピリジル）エトキシ］ベンジル｝−２−イミノ−４−チアゾリジノン及びその製造方法
EP2752428A1 (fr) 2008-06-25 2014-07-09 ESBATech, an Alcon Biomedical Research Unit LLC Humanisation d'anticorps de lapins au moyen d'une région charpente d'anticorps universelle

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4687777A (en) * 1985-01-19 1987-08-18 Takeda Chemical Industries, Ltd. Thiazolidinedione derivatives, useful as antidiabetic agents
WO2002088120A1 (fr) * 2001-04-26 2002-11-07 Léciva, a.s. Procede de production d'un antidiabetique

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4687777A (en) * 1985-01-19 1987-08-18 Takeda Chemical Industries, Ltd. Thiazolidinedione derivatives, useful as antidiabetic agents
WO2002088120A1 (fr) * 2001-04-26 2002-11-07 Léciva, a.s. Procede de production d'un antidiabetique

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005049532A3 (fr) * 2003-09-30 2006-04-06 Sun Pharmaceutical Ind Ltd Procede de purification
EP2752428A1 (fr) 2008-06-25 2014-07-09 ESBATech, an Alcon Biomedical Research Unit LLC Humanisation d'anticorps de lapins au moyen d'une région charpente d'anticorps universelle
JP2010059068A (ja) * 2008-09-02 2010-03-18 Tokuyama Corp ピオグリタゾンの製造方法
JP2010208957A (ja) * 2009-03-06 2010-09-24 Tokuyama Corp 結晶構造を有する５−｛４−［２−（５−エチル−２−ピリジル）エトキシ］ベンジル｝−２−イミノ−４−チアゾリジノン及びその製造方法

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