Field
     Production method, Nonsteroidal anti-inflammatory drugs (NSAIDs)

Keywords
     Racemic Carboxylic Acid, Phenol Derivative, Enantiomer, Benzoic Anhydride

Advantages
     Nonsteroidal anti-inflammatory drugs, usually abbreviated to NSAIDs are marketed as
     therapeutic drugs for peptic ulcer, preventive drugs for ulcer, and ulcer suppressing drugs. 
     The market leader of this field is CELEBREX (celecoxib capsules), manufactured by Pfizer Inc.
     and its sales in 2007 were 2,290m dollars.
     The present invention features an efficient method for producing only S type of enantiomers
     that occur as active ingredients through reaction using an artificial catalyst. It concerns a
     method for separating S type from R type of racemic mixtures that constitute NSAIDs, by
     adding to which an artificial asymmetric catalyst to change the rate of esterification and to
     esterify preferentially the S type as well.

Abstract
Disclosed is a method for producing an optically active ester by highly selectively esterifying one enantiomer of a racemic carboxylic acid, while producing an optically active carboxylic acid which is the other enantiomer. An optically active ester is produced while producing an optically active carboxylic acid at the same time by reacting a racemic carboxylic acid with a specific alcohol or phenol derivative in the presence of benzoic anhydride or a derivative thereof and a catalyst such as tetramisole or benzotetramisole, thereby selectively esterifying one enantiomer of the racemic carboxylic acid.


Inventor
     Prof. Isamu Shiina, Dr. Kenya Nakata　(Tokyo University of Science)


Patent Publication No
     (APPLICATION NUMBER, FILING DATE)
     WO2009054012 (Mar. 4, 2009), US12/675326 (Mar. 4, 2009), EP09719934.3 (Mar. 4, 2009),
     JP2010-502778 ( Mar. 4, 2009)
     (PUBLICATION NUMBER,  PUBLICATION DATE)
     WO2009113428 (Sep. 17, 2009), US2010/0234610（Sep. 16, 2010）,  EP2251316（Nov. 17, 2010）


Publication
J.AM. CHEM. SOC. VOL. 132, NO.33, 2010,  11629-11641

Internal file number
     LSP:94
     G2008-020, T2009-093 (T2007-127, T2007-147, T2008-066 )

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