Process for resolution of optical isomers

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United States of America Patent

PATENT NO 4463176
SERIAL NO

06417794

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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 Evansville, IN 14 103
Kreighbaum, William E Evansville, IN 9 137

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Patent Info (Count) # Cites Year
 
VIA DELLA CHIMICA 9 (1)
* 4647590 Pharmaceutical compositions and their use in the treatment of glaucoma 3 1984
 
FISONS CORPORATION (3)
* 4797498 Flavonoxypropanolamines and esters of flavonoxypropanolamines as antiarrhythmic agents 6 1986
* 4889941 Synthetic flavonoids as inhibitors of leukotrienes and 5-lipoxygenase 2 1987
* 4806660 Aurone oxypropanolamines 1 1988
 
SOLVAY SA (1)
* 2004/0210,060 Process for the separation of enantiomers and enantiopure reagent 1 2004
 
Solvay (Societe Anonyme) (1)
7138538 Process for the separation of enantiomers and enantiopure reagent 1 2004
 
NEKTAR THERAPEUTICS (1)
* 2010/0227,865 Oligomer-Beta Blocker Conjugates 0 2008
 
ASTELLAS PHARMA INC. (1)
* 5616715 Dihydropyridine-3, 5-dicarboxylic acid ester derivatives 0 1995
 
Medichem, S.A. (1)
* 5426227 Enantioselective process for the preparation of leveobunolol 0 1994
 
THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES (1)
* 5039801 Thermal fragmentation of methylbenzylurea disastereomers or secondary amines and preparation of optically active secondary amines 12 1987
 
PFIZER INC. (1)
* 5082970 Process for recycling amine isomer 20 1991
* Cited By Examiner