Title:
OPTICALLY ACTIVE SUBSTITUTED PYRIDINYLMETHYL-SULPHINYL-BENZIMIDAZOLE AND SALTS
Document Type and Number:
WIPO Patent Application WO2003089408
Kind Code:
A3
Abstract:
The present invention relates to an enantioselective catalytic oxidation process for preparation of an optically active enantiomer or an enantiomerically enriched form of substituted pyridinylmethyl-sulphinyl-benzimidazole comprising enantioselective catalytic oxidation of a substituted pyridinylmethyl prochiral sulphide derivative of benzimidazole with an oxidizing agent in an organic solvent in the presence of a base and a catalyst comprising titanium or vanadium complexed with a chiral monodentate ligand. The present invention also relates to alkali or alkaline earth metal salts of S-enantiomer of 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinylmethyl)sulfinyl]-1H-benzimidazole substantially free of sulfone impurity. The present invention also relates to a process for purification of alkali or alkaline earth metal salts of S-enantiomer of 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinylmethyl)sulfinyl]-1H-benzimidazole comprising treatment of the said alkali or alkaline earth metal salt having a sulfone impurity with a solvent system comprising an organic solvent selected from ketone and nitrile, and isolating the alkali or alkaline earth metal salt of S-enantiomer of 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinylmethyl)sulfinyl]-1H-benzimidazole which is substantially free of sulfone impurity.
Inventors:
THENNATI RAJAMANNAR (IN)
REHANI RAJEEV BUDHDEV (IN)
SONI ROHIT RAVIKANT (IN)
CHHABADA VIJAY CHHANGAMAL (IN)
PATEL VIJAYKUMAR MULJIBHAI (IN)
REHANI RAJEEV BUDHDEV (IN)
SONI ROHIT RAVIKANT (IN)
CHHABADA VIJAY CHHANGAMAL (IN)
PATEL VIJAYKUMAR MULJIBHAI (IN)
Application Number:
PCT/IN2003/000164
Publication Date:
February 05, 2004
Filing Date:
April 21, 2003
Export Citation:
Assignee:
SUN PHARMACEUTICAL IND LTD (IN)
THENNATI RAJAMANNAR (IN)
REHANI RAJEEV BUDHDEV (IN)
SONI ROHIT RAVIKANT (IN)
CHHABADA VIJAY CHHANGAMAL (IN)
PATEL VIJAYKUMAR MULJIBHAI (IN)
THENNATI RAJAMANNAR (IN)
REHANI RAJEEV BUDHDEV (IN)
SONI ROHIT RAVIKANT (IN)
CHHABADA VIJAY CHHANGAMAL (IN)
PATEL VIJAYKUMAR MULJIBHAI (IN)
International Classes:
C07D401/12; (IPC1-7): C07D401/12; A61K31/415; A61K31/44; B01J21/06; B01J31/22
Domestic Patent References:
| WO1998054171A1 | 1998-12-03 |
Foreign References:
| US5948789A | 1999-09-07 | |||
| EP1277752A1 | 2003-01-22 |
Other References:
COTTON H., ET AL.: "Asymmetric synthesis of esomeprazole", TETRAHEDRON ASYMMETRY, vol. 11, 2000, pages 3819 - 3825, XP004224163, DOI: doi:10.1016/S0957-4166(00)00352-9
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