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
Application number
PCT/IN2001/000163
Other languages
English (en)
Inventor
Sandhya Ujire
Madhavan Sridharan
Sambasivam Ganesh
Original Assignee
Biocon Limited
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 Limited filed Critical Biocon Limited
Priority to PCT/IN2001/000163 priority Critical patent/WO2003029251A1/fr
Publication of WO2003029251A1 publication Critical patent/WO2003029251A1/fr

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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)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic 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 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 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
WO2005073227A2 (fr) * 2004-01-28 2005-08-11 Usv Limited 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 (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005073227A2 (fr) * 2004-01-28 2005-08-11 Usv Limited Procede de preparation de maleate de 5-[4-[2-[n-methyl-n-(2-pyridyl) amino] ethoxy] phenyl methyl] thiazolidine-2, 4-dione
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
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
WO2011133442A1 (fr) * 2010-04-19 2011-10-27 Metabolic Solutions Development Company Nouvelle synthèse de thiazolidinediones
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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