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WO2003029251A1 - Procede de synthese de derives thiazolidinedione - Google Patents

Procede de synthese de derives thiazolidinedione Download PDF

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Publication number
WO2003029251A1
WO2003029251A1 PCT/IN2001/000163 IN0100163W WO03029251A1 WO 2003029251 A1 WO2003029251 A1 WO 2003029251A1 IN 0100163 W IN0100163 W IN 0100163W WO 03029251 A1 WO03029251 A1 WO 03029251A1
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WO
WIPO (PCT)
Prior art keywords
formula
compound
synthesis
reaction
reacting
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/IN2001/000163
Other languages
English (en)
Inventor
Sandhya Ujire
Madhavan Sridharan
Sambasivam Ganesh
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.)
Biocon Ltd
Original Assignee
Biocon Ltd
Biocon India 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 Biocon Ltd, Biocon India Ltd filed Critical Biocon Ltd
Priority to PCT/IN2001/000163 priority Critical patent/WO2003029251A1/fr
Publication of WO2003029251A1 publication Critical patent/WO2003029251A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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

Definitions

  • the present invention relates to process of preparing thiazolidinedione derivatives of formula I known for the treatment of non-insulin dependent diabetes.
  • Non-insulin-dependent diabetes mellitus is a metabolic 0 disorder leading to long-term complications and premature atherosclerosis.
  • EP 0 306 228 describes such a procedure for the synthesis of a number of thiazolidinedione derivatives.
  • US patent 5,726,055 describes a process wherein a yeast reductase, R odotorula giutinis the microbial reductase source for the reduction of the benzylidine group to the desired product.
  • WO 99/23095 describes a process using a noble metal mediated reduction for the benzylidine group while, EP 0306 228 discloses a process for the benzylidine group reduction using dissolving metal methods.
  • the present invention details a process for the preparation of compounds of formula I,
  • This invention particularly relates to a process for the preparation of thiazolidinedione derivatives of the general formula L
  • step (i) is carried out in the presence of a mixture of alumina/lithium hydroxide.
  • step (i) is carried in an organic solvent selected from dimethyl formamide, acetonitrile, toluene or xylene.
  • step (ii) is selected from sodium in methanol, magnesium in methanol, NaBH 4 -
  • step (ii) is carried in tetrahydrofuran.
  • Ar is an unsubstituted or substituted heteroaryl
  • X can be either CH or N
  • R can be either H or alkyl n is 1 when X is CH and R is H n is 2 when X is N and R is CH 3 and G is either F or OH

Landscapes

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

Abstract

L'invention concerne les composés de la formule (I) servant au traitement du diabète non insulino-dépendant, Ar étant hétéroaryl éventuellement substitué, X étant CH ou N, R étant H ou alkyl, et n étant 1 ou 2. Les composés selon l'invention sont fabriqués par réaction de composés de formule (II) avec des composés de formule (VI) dans laquelle G est OH ou F.
PCT/IN2001/000163 2001-09-28 2001-09-28 Procede de synthese de derives thiazolidinedione Ceased WO2003029251A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/IN2001/000163 WO2003029251A1 (fr) 2001-09-28 2001-09-28 Procede de synthese de derives thiazolidinedione

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2001/000163 WO2003029251A1 (fr) 2001-09-28 2001-09-28 Procede de synthese de derives thiazolidinedione

Publications (1)

Publication Number Publication Date
WO2003029251A1 true WO2003029251A1 (fr) 2003-04-10

Family

ID=11076382

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2001/000163 Ceased WO2003029251A1 (fr) 2001-09-28 2001-09-28 Procede de synthese de derives thiazolidinedione

Country Status (1)

Country Link
WO (1) WO2003029251A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005073227A3 (fr) * 2004-01-28 2005-09-22 Usv Ltd Procede de preparation de maleate de 5-[4-[2-[n-methyl-n-(2-pyridyl) amino] ethoxy] phenyl methyl] thiazolidine-2, 4-dione
WO2006026934A1 (fr) * 2004-09-10 2006-03-16 Zentiva, A.S. Methode pour la preparation de rosiglitazone
WO2009148195A1 (fr) * 2008-06-02 2009-12-10 Daebong Ls, Ltd. Composé de 5(4-hydroxybenzyl)thiazolidine-2,4-dione comme produit intermédiaire dans la synthèse de composés à base de thiazolidinedione et procédé de préparation de celui-ci
WO2011133442A1 (fr) * 2010-04-19 2011-10-27 Metabolic Solutions Development Company Nouvelle synthèse de thiazolidinediones
WO2012021467A1 (fr) * 2010-08-10 2012-02-16 Metabolic Solutions Development Company, Llc Nouvelle synthèse pour des composés de thiazolidinedione
US8933240B2 (en) 2010-08-10 2015-01-13 Metabolic Solutions Development Company, Llc Synthesis for thiazolidinedione compounds

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5002953A (en) * 1987-09-04 1991-03-26 Beecham Group P.L.C. Novel compounds
GB2324089A (en) * 1997-04-08 1998-10-14 Nitto Chemical Industry Co Ltd Process for the production of a thiazolidine derivative
WO2001012628A1 (fr) * 1999-08-17 2001-02-22 Smithkline Beecham P.L.C. Compositions pharmaceutiques contenant des derives de thiazolidinedione et procede de preparation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5002953A (en) * 1987-09-04 1991-03-26 Beecham Group P.L.C. Novel compounds
GB2324089A (en) * 1997-04-08 1998-10-14 Nitto Chemical Industry Co Ltd Process for the production of a thiazolidine derivative
WO2001012628A1 (fr) * 1999-08-17 2001-02-22 Smithkline Beecham P.L.C. Compositions pharmaceutiques contenant des derives de thiazolidinedione et procede de preparation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
GILES R G ET AL: "Regiospecific reduction of 5-benzylidene-2,4-thiazolidinediones and 4-oxo-2-thiazolidinethiones using lithium borohydride in pyridine and tetrahydrofuran", TETRAHEDRON, vol. 56, no. 26, June 2000 (2000-06-01), pages 4531 - 4537, XP004202146 *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005073227A3 (fr) * 2004-01-28 2005-09-22 Usv Ltd Procede de preparation de maleate de 5-[4-[2-[n-methyl-n-(2-pyridyl) amino] ethoxy] phenyl methyl] thiazolidine-2, 4-dione
WO2006026934A1 (fr) * 2004-09-10 2006-03-16 Zentiva, A.S. Methode pour la preparation de rosiglitazone
WO2009148195A1 (fr) * 2008-06-02 2009-12-10 Daebong Ls, Ltd. Composé de 5(4-hydroxybenzyl)thiazolidine-2,4-dione comme produit intermédiaire dans la synthèse de composés à base de thiazolidinedione et procédé de préparation de celui-ci
WO2011133442A1 (fr) * 2010-04-19 2011-10-27 Metabolic Solutions Development Company Nouvelle synthèse de thiazolidinediones
CN102947269A (zh) * 2010-04-19 2013-02-27 新陈代谢解决方案开发公司 噻唑烷二酮化合物的新的合成方法
US8937182B2 (en) 2010-04-19 2015-01-20 Metabolic Solutions Development Company, Llc Synthesis for thiazolidinedione compounds
AU2011242956B2 (en) * 2010-04-19 2015-01-22 Cirius Therapeutics, Inc. Novel synthesis for thiazolidinedione compounds
CN102947269B (zh) * 2010-04-19 2015-11-25 新陈代谢解决方案开发公司 噻唑烷二酮化合物的新的合成方法
WO2012021467A1 (fr) * 2010-08-10 2012-02-16 Metabolic Solutions Development Company, Llc Nouvelle synthèse pour des composés de thiazolidinedione
US8895748B2 (en) 2010-08-10 2014-11-25 Metabolic Solutions Development Company, Llc Synthesis for thiazolidinedione compounds
US8933240B2 (en) 2010-08-10 2015-01-13 Metabolic Solutions Development Company, Llc Synthesis for thiazolidinedione compounds
US8946435B2 (en) 2010-08-10 2015-02-03 Metabolic Solutions Development Company, Llc Synthesis for thiazolidinedione compounds

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