OPTICALLY ACTIVE THIAZETOQUINOLINE-3-CARBOXYLIC ACID DERIVATIVE, ITS PRODUCTION AND USE

• Main Authors: ITO YASUO, YASUDA SHINGO, YAMAMOTO YOICHI, YOSHIDA TOSHIHIKO, KATO HIDEO
• Format: Patent
• Language: English
• Published: 09.09.1992
• Subjects: 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

PURPOSE:To provide the subject compound having remarkably increased antibacterial activity especially against clinical isolate, free from convulsion-inducing action caused by the combined use with anti-inflammatory agent and useful as an antibacterial agent, anti-tumor agent and therapeutic agent for AIDS. CONSTITUTION:The compound of formula I (R is H or lower alkyl; R is H, carboxylic acid ester residue, etc.; C atom labeled with * is asymmetric C atom having absolute configuration of R or S) and its salt, e.g. (1S,3'S)-7-(3- amino-1-pyrrolidinyl)-6-fluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2- a]quinoline-3- carboxylic acid. The compound can be produced by reducing and dehalogenating an optically active 8-halogenothiazetoquinoline-3-carboxylic acid derivative of formula II (X is halogen) and, as necessary, hydrolyzing the product. The compound of formula II is also a new compound, which can be produced e.g. by reacting a compound of formula III (Y is X) with a compound of formula IV and halogenating the reaction product.