167888-38-2Relevant academic research and scientific papers
Substituted aminocycloalkylpyrrolidine derivatives and cis-substituted aminocycloalkylpyrrolidine derivatives
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, (2008/06/13)
An antimicrobial drug having excellent antimicrobial activity and high safety is disclosed, which comprises as an active ingredient, a quinolone-derivative having a substituted aminocycloalkylpyrrolidine as a substituent and which is further substituted w
Studies on quinolone antibacterials. IV. Structure-activity relationships of antibacterial activity and side effects for 5- or 8-substituted and 5,8- disubstituted-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-1,4-dihydro-4- oxoquinoline-3-carboxylic acids
Yoshida,Yamamoto,Orita,Kakiuchi,Takahashi,Itakura,Kado,Mitani,Yasuda,Kato,Itoh
, p. 1074 - 1085 (2007/10/03)
A series of 7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-1,4-dihydro-4- oxoquinoline-3-carboxylic acids bearing various substituents (H, F, Cl, Me, OH, OMe, OEt, OCH2F, OCHF2, OCF3, SMe) at the C-8 position was prepared and evaluated for in vitro antibacterial activity against both standard laboratory strains and bacteria resistant to quinolones such as ciprofloxacin (CPFX, 1) and ofloxacin (OFLX, 2) from clinical isolates. The 8-methyl (8a), 8-fluoro (9a), 8-chloro (10a) and 8-methoxy (12a) compounds were 4 times more potent than CPFX (1) against both gram-positive and gram-negative bacteria. But these four compounds caused injury to the chromosomes of mammalian cells at a concentration of 100 μg/ml. Next, a series of quinolones having various substituents (H, Cl, Me, NH2, NHMe, NMe2) at the C-5 position was prepared and evaluated for antibacterial activity and injurious effect on the chromosome. We found that the 5-amino-8-methyl compound (8d) showed strong antibacterial activity (in vitro antibacterial activity of 8d is 4 times more potent than that of CPFX (1) against both gram-positive and gram-negative bacteria), reduced injury to the chromosome, and reduced quinolone-type toxicity (free from both phototoxicity at a dosage of 30 mg/kg in guinea pigs (i.v.) and convulsion-inducing activity when coadministered with fenbufen at a dosage of 100 mg/kg in mice (i.p.)).
5-amino-8-methyl-7-pyrrolidinylquinoline-3-carboxylic acid derivative
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, (2008/06/13)
A 5-amino-8-methyl-7-pyrrolidinylquinoline-3-carboxylic acid derivative represented by the general formula: STR1 wherein R1 is a hydrogen atom or a lower alkyl group; R2 is a hydrogen atom, a lower alkyl group, a lower alkanoyl group, a halogenated lower alkanoyl group or a residue of carboxylic acid ester; R3 is a hydrogen atom or a lower alkyl group; R4, R5 or R6 are each independently a hydrogen atom or a lower alkyl group; or two of R4, R5 and R6 may be taken together to form a --(CH2)n -group wherein n is 1 or 2, a stereoisomer thereof, or a pharmacologically acceptable salt thereof, the process for preparing these compounds, a pharmaceutical composition comprising an effective amount of these compounds and methods for the treatment of infectious diseases through the administration to patients of an effective amount of these compounds, and intermediates of these compounds are disclosed. These compounds are effective as antibacterial agents.
