Synthetic method and intermediates of Rosuvastatin calcium...

Details Synthetic method and intermediates of Rosuvastatin calcium... Synthetic method and intermediates of Rosuvastatin calcium...

2005-11-18

2011-11-01

Balasubramanian, Venkataraman (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C544S249000, C544S332000

Reexamination Certificate

active

08049010

ABSTRACT:
The present invention publicly discloses a synthetic method and intermediates of rosuvastatin calcium and synthetic methods of the intermediates. The synthetic method uses 4-4′-fluorophenyl-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyridine-5-formaldehyde as the raw material, includes 4-4′-fluorophenyl-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyridine-5-acrylonitrile (intermediate I) from a nitrilized reaction, and 4-4′-fluorophenyl-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyridine-5-acraldehyde (intermediate II) from an aldehydized reaction of the intermediate I, and further goes through such unit processes as side-chain extension, ketone-group reduction, ethyl-group hydrolysis and neutralization reaction or decomposition reaction to obtain rosuvastatin calcium. The nitrilized reagent can be phosphate diethylacetonitrile, acetonitrile, etc.; the aldehyde reductant can be diisobutyl aluminum hydride, red aluminum, etc.; and the ketone-group reductant can be diethylmethoxyborane, NaBH4, KBH4, etc.

REFERENCES:
patent: 5260440 (1993-11-01), Hirai et al.
patent: 2009/0124803 (2009-05-01), Deshpande
patent: WO 0049014 (2000-08-01), None
patent: WO 03009714 (2003-11-01), None
patent: WO 2004103977 (2004-12-01), None
patent: WO 2005063728 (2005-07-01), None

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