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, IN84

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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