N-substituted cycloserines and process

Details N-substituted cycloserines and process N-substituted cycloserines and process

C - Chemistry, Metallurgy

07

D

260/311.9

C07D 261/04 (2006.01)

Patent

CA 1039292

ABSTRACT OF THE DISCLOSURE Novel stabilized cycloserine compositions, having enhanced stability, and effective in releasing cycloserine compounds in vivo, are prepared by reacting D-4-amino-3-isoxazolidinone or its 5-methyl derivative with 2,4-pentanedione or alkyl-substituted-2,4-pentane- dione to form the corresponding N-substituted-cycloserine compound in which one of the hydrogens attached to the primary amino group is replaced by 1-methyl-3-oxo-1- butenyl or an alkyl substituted-1-methyl-3-oxo-1-butenyl grouping. These novel D-4-(1'-methyl-3'-oxo-1'-butenyl or alkyl-substituted-1'-methyl-3'-oxo-1'-butenyl)amino- 3-isoxazolidinones or 5-methyl derivative thereof, which may also be referred to as N-(1-methyl-3-oxo-1-butenyl or alkyl-substituted-1-methyl-3-oxo-1-butenyl)-derivative of cycloserine or methyl-cycloserine, as well as their pharmacologically acceptable salts, are remarkably stable on storage as well as upon oral administration, and are extremely effective in releasing in vivo the cycloserine compound containing the free primary amino grouping. - 1 -

205980

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