1-Ethyl-7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4- dihydro-4-oxo-3-quinoline-carboxylic acid. New quinolone antibacterial with potent gram-positive activity.
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Animals↗
Biomedical subjects
J M Domagala
Publications and source records attributed to J M Domagala.
In vitro activity of CI-934, a quinolone carboxylic acid active against gram-positive and -negative bacteria.
CI-934 is a totally synthetic difluorinated quinolinecarboxylic acid with an ethyl-amino-methyl pyrrolidine side chain, which has broad-spectrum antibacterial activity, including particular potency directed against streptococci and staphylococci. The CI-934 MIC (micrograms per milliliter) for 90% of the strains tested was 0.4 (range, 0.2 to 0.8) for a group of streptococci (pneumococci, viridans streptococci, Streptococcus faecalis, and Lancefield groups A, B, and C), 0.2 (0.05 to 0.2) for staphylococci (including methicillin-resistant Staphylococcus aureus), 0.025 (less than or equal to 0.003 to 0.025) for Haemophilus influenzae and Neisseria gonorrhoeae, 1.6 (0.1 to 25) for Enterobacteriaceae, 25 (3.1 to 25) for Pseudomonas aeruginosa, and 1.6 (0.05 to 3.1) for non-Bacteroides anaerobe species. CI-934 was equally active in vitro against multi-drug-resistant and -sensitive isolates, and cross-resistance was not apparent. Potency increased with alkalinity and was somewhat lower in urine. CI-934 was bactericidal. Inhibitory activity was generally unaffected by anaerobiosis, light, changes in inoculum size or cation concentration, or addition of human serum or sodium cholate.
Anaerobiosis↗
Semisynthetic penicillins and cephalosporins containing the substituted 6-vinyl-1,2-dihydro-2-oxo- and 1,4-dihydro-4-oxo-3-pyridinecarboxylic acid side chains. Synthesis and structure-activity relationships.
A series of penicillins and cephalosporins containing the substituted 6-vinyl-1,2-dihydro-2-oxo- and 1,4-dihydro-4-oxo-3-pyridinecarboxylic acid side chains has been prepared and compared to piperacillin and cefoperazone. The compounds show good activity when tested in vitro against an array of Gram-negative bacteria. In vitro activity was also demonstrated against several species of Gram-positive bacteria. Two compounds, 14 and 21, show good in vivo activity when tested against Klebsiella pneumoniae, Enterobacter cloacae, and two strains of Pseudomonas aeruginosa.
Animals↗
Semisynthetic cephalosporins with alpha-oximino acid side chains. The preparation and coupling of 4-acylamino-alpha-oximinobenzeneacetic acids and 1,2-dihydro-6-methyl-alpha-oximino-2-oxo-3-pyridineacetic acid to 7-aminocephalosporanic acid.
A series of 4-acylamino-alpha-oximinobenzeneacetic acids, and 1,2-dihydro-6-methyl-alpha-oximino-2-oxo-3-pyridineacetic acid were prepared and coupled to 7-aminocephalosporanic acid and its 3'-(1-methyltetrazol-5-yl)thiolo analogue. Several coupling methods and oxime protecting groups were thoroughly examined. The best coupling procedure employed dimethylchloroformiminium chloride, and the tetrahydropyranyl (THP) group was selected for oxime protection. The cephalosporins prepared were tested and compared to cefuroxime and cefotaxime. The corresponding alpha-keto acids, and O-methyl oximes were also examined.
Anilides↗