A new antipseudomonal cephalosporin CP6162 and its congeners.

The synthesis and biological activity of a series of 3-[2-(5-hydroxy-4-pyridon-2-yl)ethenyl]cephalosporin derivatives are described. They showed very potent activity against Gram-negative bacteria, especially Pseudomonas aeruginosa. (6R, 7R)-7-[(Z)-2-(2-Aminothiazol-4-yl)-2 -(1-carboxy-1-methyl)-ethoxyiminoacetamido]-3-[(Z)-2-(1,5-dihydrox y-4- pyridon-2-yl)ethenyl]ceph-3-em-4-carboxylic acid, CP6162 (8e), was selected for further evaluation as antipseudomonal chemotherapeutic agent.

[1]  T. Matsumoto,et al.  In-vitro and in-vivo antimicrobial activities of a novel cephalosporin derivative, CP6162, possessing a dihydroxypyridone moiety at the C-3 side chain. , 1991, The Journal of antimicrobial chemotherapy.

[2]  S. Inouye,et al.  Synthesis and biological activity of (cyclopentenopyridinium) thiomethylcephalosporins. , 1990, The Journal of antibiotics.

[3]  T. Yoshida,et al.  Synthesis and oral activity of ME1207, a new orally active cephalosporin. , 1990, The Journal of antibiotics.

[4]  S. Inouye,et al.  New aminothiazolylglycylcephalosporins with a 1,5-dihydroxy-4-pyridone-2-carbonyl group. I. Synthesis and biological activity of cephalosporin derivatives leading to MT0703. , 1990, Journal of antibiotics (Tokyo. 1968).

[5]  S. Inouye,et al.  New aminothiazolylglycylcephalosporins with a 1,5-dihydroxy-4-pyridone-2-carbonyl group. II. Synthesis and antibacterial activity of MT0703 and its diastereomers. , 1990, The Journal of antibiotics.

[6]  T. Kudo,et al.  A new aminothiazolylcephalosporin having 1-carboxyethoxyimino group, ME1228. , 1990, The Journal of antibiotics.

[7]  N. Tanaka,et al.  In vitro and in vivo antibacterial activities of BO-1341, a new antipseudomonal cephalosporin , 1989, Antimicrobial Agents and Chemotherapy.

[8]  R. Fromtling,et al.  L-658,310, a new injectable cephalosporin. I. In vitro antibacterial properties. , 1989, The Journal of antibiotics.

[9]  H. Kawaguchi,et al.  Synthesis and structure-activity relationships of a new oral cephalosporin, BMY-28100 and related compounds. , 1987, The Journal of antibiotics.

[10]  R. Hara,et al.  Studies on beta-lactam antibiotics. I. Synthesis and in vitro anti-pseudomonal activity of 3-isothiazole-cephalosporin derivatives. , 1987, The Journal of antibiotics.

[11]  H. Ishitobi,et al.  Highly stereoselective methoxylation at the seven position of cephalosporins , 1987 .

[12]  H. Yamanaka,et al.  STUDIES ON β-LACTAM ANTIBIOTICS , 1985 .

[13]  J. Nokami,et al.  Penicillin-cephalosporin conversion III. A Novel route to 3-chloromethyl-Δ3-cephems , 1982 .

[14]  J. Verhaegen,et al.  GR-20263: a new aminothiazolyl cephalosporin with high activity against Pseudomonas and Enterobacteriaceae , 1980, Antimicrobial Agents and Chemotherapy.

[15]  D. M. Ryan,et al.  GR 20263, a new broad-spectrum cephalosporin with anti-pseudomonal activity , 1980, Antimicrobial Agents and Chemotherapy.

[16]  H. Bickel,et al.  Modifikationen von Antibiotika. 2. Mitteilung [1]. Über die Darstellung von 7‐Amino‐cephalosporansäure , 1968 .

[17]  M. Zaoral,et al.  A novel peptide synthesis , 1960 .

[18]  D. Turner Oxidation of Aromatic Alcohols with Manganese Dioxide , 1954 .

[19]  K. Heyns,et al.  Über γ‐Pyrone und γ‐Pyridone, II. Mitteil.): Darstellung und Eigenschaften einiger substituierter γ‐Pyridone , 1954 .