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1. WO2006094468 - METHOD OF RACEMIZATION OF THE R(-) ISOMER OF THE (2-CHLOROPHENYL)-6,7- DIHYDROTHIENO[3,2-c]PYRIDINE-5(4H)-ACETIC ACID METHYL ESTER

Publication Number WO/2006/094468
Publication Date 14.09.2006
International Application No. PCT/CZ2006/000010
International Filing Date 03.03.2006
Chapter 2 Demand Filed 26.10.2006
IPC
C07D 495/04 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
495Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
CPC
C07D 495/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
495Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
Applicants
  • ZENTIVA, A.S. [CZ]/[CZ] (AllExceptUS)
  • HAJICEK, Josef [CZ]/[CZ] (UsOnly)
  • STEPANKOVA, Hana [CZ]/[CZ] (UsOnly)
  • KALIDOVA, Jan [CZ]/[CZ] (UsOnly)
Inventors
  • HAJICEK, Josef
  • STEPANKOVA, Hana
  • KALIDOVA, Jan
Agents
  • JIROTKOVA, Ivana
Priority Data
PV 2005-15008.03.2005CZ
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) METHOD OF RACEMIZATION OF THE R(-) ISOMER OF THE (2-CHLOROPHENYL)-6,7- DIHYDROTHIENO[3,2-c]PYRIDINE-5(4H)-ACETIC ACID METHYL ESTER
(FR) PROCEDE DE RACEMISATION DE L’ISOMERE R(-) DE L’ESTER DE METHYLE DE L’ACIDE (2-CHLOROPHENYL)-6,7-DIHYDROTHIENO[3,2-c]PYRIDINE-5(4H)-ACETIQUE
Abstract
(EN)
Racemization of the R(-) isomer of the (2-chlorophenyl) -6, 7-dihydrothieno [3, 2-c]pyridine- 5 (4H) -acetic acid methyl ester (Formula II) (also called R clopidogrel) is performed via conversion of a portion thereof to the S (+) isomer and it takes place in an organic solvent selected from alcohols , esters, ketones or ethers, or in their mixtures, in the presence of a base selected from substances of formula R1R2R3R4N+OH' wherein R1, R2, R3 and R4 are identical or different substituents selected from C1-C5 alkyls or C5, C6 cycloalkyls or aryls, C7-C9 alkyl-cycloalkyls or alkyl-aryls, the molar ratio of the base to the starting substance being 1: 1 to 1: 10. ,OMe Cl I Cl <VOMe II
(FR)
La racémisation selon l’invention de l’isomère R(-) de l’ester de méthyle de l’acide (2-chlorophényl)-6,7-dihydrothiéno[3,2-c]pyridine-5(4H)-acétique (Formule II) (également appelé (R)-clopidogrel) est réalisée par transformation d'une partie de celui-ci en l’isomère S(+) et elle a lieu dans un solvant organique choisi parmi des alcools, des esters, des cétones ou des éthers, ou dans leurs mélanges, en présence d'une base choisie parmi des substances répondant à la formule R1R2R3R4N+OH-, dans laquelle R1, R2, R3 et R4 sont des substituants identiques ou différents choisis parmi des groupes alkyle en C1 à C5 ou des groupes cycloalkyle ou aryle en C5 ou C6, des groupes alkyl-cycloalkyle ou alkyl-aryle en C7 à C9, le rapport molaire de la base sur le produit de départ étant de 1/1 à 1/10, OMe Cl I Cl < VOMe II.
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