WO2004024059A3 - Improved process for preparation of thiazolidinedione derivatives - Google Patents

Improved process for preparation of thiazolidinedione derivatives Download PDF

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Publication number
WO2004024059A3
WO2004024059A3 PCT/IB2003/003858 IB0303858W WO2004024059A3 WO 2004024059 A3 WO2004024059 A3 WO 2004024059A3 IB 0303858 W IB0303858 W IB 0303858W WO 2004024059 A3 WO2004024059 A3 WO 2004024059A3
Authority
WO
WIPO (PCT)
Prior art keywords
general formula
formula
halopropionate
derivative
preparation
Prior art date
Application number
PCT/IB2003/003858
Other languages
French (fr)
Other versions
WO2004024059A2 (en
Inventor
Rajendra Ghanshamlal Lala
Parag Narayan Gadkari
Maya Janak Shah
Janak Ramanlal Shah
Original Assignee
Themis Lab Private Ltd
Rajendra Ghanshamlal Lala
Parag Narayan Gadkari
Maya Janak Shah
Janak Ramanlal Shah
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 Themis Lab Private Ltd, Rajendra Ghanshamlal Lala, Parag Narayan Gadkari, Maya Janak Shah, Janak Ramanlal Shah filed Critical Themis Lab Private Ltd
Priority to AU2003260813A priority Critical patent/AU2003260813A1/en
Publication of WO2004024059A2 publication Critical patent/WO2004024059A2/en
Publication of WO2004024059A3 publication Critical patent/WO2004024059A3/en

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Classifications

    • 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

Abstract

Method of obtaining anti diabetic agent of formula (7A) where in R=alkyl, aryl, heteroaryl, or trifluoromethyl as per the reaction scheme wherein the corresponding pyridine base of general formula (8A), where in Z is a leaving group other than halogen with p-nitro phenol (9) under basic conditions, followed by (a) catalytically reducing the nitro group in compound of general formula (10A) with hydrogen (b) diazotizing the amino group present in the organic residue (11A) (c) converting the diazotized residue into a derivative of 2-halopropionate of general formula (12A) following Meerwein arylation using acrylate ester (d) cyclizing the derivative of 2-halopropionate of formula (12A), with thiouriea (e) hydrolizing the resulting imine (13A), thus giving thiazolidinedione of general formula (7A) as an antidiabetic agent, in particular pioglitazone where R=ethyl in (7A).
PCT/IB2003/003858 2002-09-12 2003-08-29 Improved process for preparation of thiazolidinedione derivatives WO2004024059A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003260813A AU2003260813A1 (en) 2002-09-12 2003-08-29 Improved process for preparation of thiazolidinedione derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN823/MUM/2002 2002-09-12
IN823MU2002 2002-09-12

Publications (2)

Publication Number Publication Date
WO2004024059A2 WO2004024059A2 (en) 2004-03-25
WO2004024059A3 true WO2004024059A3 (en) 2004-11-04

Family

ID=31986002

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2003/003858 WO2004024059A2 (en) 2002-09-12 2003-08-29 Improved process for preparation of thiazolidinedione derivatives

Country Status (2)

Country Link
AU (1) AU2003260813A1 (en)
WO (1) WO2004024059A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006035459A1 (en) * 2004-09-28 2006-04-06 Morepen Laboratories Limited An improved process for the production of derivatives of thiozolidinediones and their precursors
WO2006117654A1 (en) * 2005-05-03 2006-11-09 Ranbaxy Laboratories Limited Processes for the preparation of pioglitazone or salts thereof
JP5334422B2 (en) * 2008-02-13 2013-11-06 株式会社トクヤマ Process for producing 5- {4- [2- (5-ethyl-2-pyridyl) ethoxy] benzyl} -2-imino-4-thiazolidinone
JP5197063B2 (en) * 2008-02-21 2013-05-15 株式会社トクヤマ Process for producing methyl 2-bromo-3- {4- [2- (5-ethyl-2-pyridyl) ethoxy] phenyl} propionate
JP5383123B2 (en) * 2008-09-02 2014-01-08 株式会社トクヤマ Method for producing pioglitazone hydrochloride
JP2010208957A (en) * 2009-03-06 2010-09-24 Tokuyama Corp 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2-imino-4-thiazolidinone having crystal structure and method for producing the same
WO2012153312A1 (en) 2011-05-11 2012-11-15 Ranbaxy Laboratories Limited Process for the purification of pioglitazone
CN111875598B (en) * 2020-05-23 2023-10-10 白银京宇新药业有限公司 Preparation method of pioglitazone

Citations (3)

* 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
US5585495A (en) * 1991-12-20 1996-12-17 The Upjohn Company Reduction method for substituted 5-methylene-thiazolidinediones
US6100403A (en) * 1996-06-27 2000-08-08 Takeda Chemical Industries, Ltd. Production of benzaldehyde compounds

Patent Citations (3)

* 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
US5585495A (en) * 1991-12-20 1996-12-17 The Upjohn Company Reduction method for substituted 5-methylene-thiazolidinediones
US6100403A (en) * 1996-06-27 2000-08-08 Takeda Chemical Industries, Ltd. Production of benzaldehyde compounds

Also Published As

Publication number Publication date
AU2003260813A8 (en) 2004-04-30
WO2004024059A2 (en) 2004-03-25
AU2003260813A1 (en) 2004-04-30

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