US Patent No: 4,463,176

Number of patents in Portfolio can not be more than 2000

Process for resolution of optical isomers

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Abstract

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A process for resolving a racemic modification of .beta.-adrenergic aryl-or hetaryl-oxypropanolamines such as (.+-.)-2-[2-hydroxy-3-[[2-(1H-indol-3-yl)-1,1-dimethylethyl]amino]propoxy]benzonitrile into its individual enantiomers is described. The process comprises converting the racemic modification into a pair of diastereomeric urea derivatives by reaction with a chiral aralkylisocyanate; separation into the individual diastereomers; and facile regeneration of the starting amine by cleavage of the intermediate urea compound using hydrazine. This final step is improved by the addition of an .alpha.-keto carboxylic acid, such as pyruvic acid, which functions as a scavenger of nucleophilic by-products.

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Patent Owner(s)

Patent OwnerAddressTotal Patents
MEAD JOHNSON & COMPANYEVANSVILLE, IN3

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Inventor(s)

Inventor Name Address # of filed Patents Total Citations
Dennis, Ronald D Evansville, IN 4 12
Dolak, Terence M 27 Mountain View Dr., Andover, NJ 07821 14 98
Kreighbaum, William E Evansville, IN 9 126

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Patent Info (Count) # Cites Year
 
FISONS CORPORATION (3)
* 4,797,498 Flavonoxypropanolamines and esters of flavonoxypropanolamines as antiarrhythmic agents 6 1986
* 4,889,941 Synthetic flavonoids as inhibitors of leukotrienes and 5-lipoxygenase 2 1987
* 4,806,660 Aurone oxypropanolamines 1 1988
 
ASTELLAS PHARMA INC. (1)
* 5,616,715 Dihydropyridine-3, 5-dicarboxylic acid ester derivatives 0 1995
 
MEDICHEM, S.A. (1)
* 5,426,227 Enantioselective process for the preparation of leveobunolol 0 1994
 
NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT (1)
* 5,039,801 Thermal fragmentation of methylbenzylurea disastereomers or secondary amines and preparation of optically active secondary amines 11 1987
 
PFIZER INC. (1)
* 5,082,970 Process for recycling amine isomer 20 1991
 
SOLVAY (SOCIETE ANONYME) (1)
7,138,538 Process for the separation of enantiomers and enantiopure reagent 1 2004
 
VIA DELLA CHIMICA 9 (1)
* 4,647,590 Pharmaceutical compositions and their use in the treatment of glaucoma 3 1984
* Cited By Examiner