5-AMINO-1-CYCLOPROPYL-4-OXOQUINOLINE-3-CARBOXYLIC ACID DERIVATIVE AND ITS PREPARATION

PROBLEM TO BE SOLVED: To safely prepare the subject compounds useful as a synthetic antimicrobial agent in high yield by N-acylating aminocyclopropylanilines, forming the product into an anilinomethylenemalonic ester thereof, and cyclizing and hydrolyzing the obtained ester. SOLUTION: N-cyclopropyla...

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Bibliographic Details
Main Authors UMETSU KAZUTO, HAMADA YUSUKE
Format Patent
LanguageEnglish
Published 15.06.1999
Edition6
Subjects
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
HETEROCYCLIC COMPOUNDS
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS
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Summary:PROBLEM TO BE SOLVED: To safely prepare the subject compounds useful as a synthetic antimicrobial agent in high yield by N-acylating aminocyclopropylanilines, forming the product into an anilinomethylenemalonic ester thereof, and cyclizing and hydrolyzing the obtained ester. SOLUTION: N-cyclopropylanilines of formula I (X is a halogen; R is an alkyl) are acylated to provide 5-acylamino-N-cyclopropylanilines of formula II (R is an alkyl, an alkenyl or the like). The compound of formula II is reacted with a dialkyl alkoxymethylenemalonate to provide anilinomethylenemalonic acids of formula III (R is an alkyl), and the compound of formula III is subjected to intramolecular dealcoholation reaction to provide an alkyl 5- acylamino-1-cyclopropyl-4-oxoquinoline-3-carboxylate of formula IV. Finally, the ester of formula IV is hydrolyzed under an acidic condition to provide 5-amino-1-cyclopropyl-4-oxoquinolinecarboxylic acid of formula V in the method for producing the 5-amino-1-cyclopropyl-4-oxoquinolinecarboxylic acid derivative.
Bibliography:Application Number: JP19970342094