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Latamoxef sodium

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Latamoxef sodium Basic information
Latamoxef sodium Chemical Properties
  • alpha D22 -45° (water)
  • storage temp. Inert atmosphere,2-8°C
  • Merck 13,6311
  • InChIKeyGRIXGZQULWMCLU-GDUWRUPCSA-L
Safety Information
  • Hazard Codes Xn
  • Risk Statements 42/43
  • Safety Statements 22-36/37-45
  • WGK Germany 2
  • RTECS RN6824000
MSDS
Latamoxef sodium Usage And Synthesis
  • OriginatorMoxam,Lilly,US,1981
  • UsesMoxalactam Sodium is an oxacephem antibiotic. Moxalactam Sodium is more effective against Escherichia coli and Pseudomonas aeruginosa than cephalosporins.
  • UsesAntibacterial;Bacterial transpeptidase inhibitor
  • Manufacturing ProcessTo a stirred suspension of p-(p-methoxybenzyloxy)-phenylmalonic acid (125 mg) in methylene chloride (3 ml) are added triethylamine (55 l) and oxalyl chloride (26 l) at -15°C, and the suspension is stirred for 40 minutes at 0°C. The mixture is added to a solution of diphenylmethyl 7β-amino-7α-methoxy-3- (1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylate (100 mg) in methylene chloride (3 ml) and pyridine (63 l), and the mixture is stirred for 30 minutes at 0°C. The reaction mixture is diluted with ethyl acetate, washed with aqueous 2N-hydrochloric acid and water, dried over sodium sulfate, and concentrated to give crude product (212 mg), which is chromatographed on silica gel (20 g) and eluted with a mixture of ethyl acetate and acetic acid (99:1) to give diphenylmethyl-7β-[α-p-(pmethoxybenzyloxy)phenyl-α-carboxyacetamido]-7α-methoxy-3-(1- methyltetrazol-5yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylate as foam (71 mg). Yield: 45%.
    To a solution of diphenylmethyl-7β-[α-p-(p-methoxybenzyl)-oxy-phenyl-α-pmethoxybenzyl-oxycarbonil-acetamido]-7α-methoxy-3-(1-methyltetrazol-5- yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylate (1.20 g) in methylene chloride (24 ml) are added anisole (2.4 ml) and a solution of aluminum chloride (2.58 g) in nitromethane (12 ml) at 0°C under nitrogen. After stirring for 15 minutes at 0°C, the mixture is poured into cold 5% sodium hydrogen carbonate aqueous solution (100 ml) and filtered to remove the formed precipitate. The filtate is washed twice with methylene chloride (2 x 100 ml), acidified with 2N-hydrochloric acid to pH 2.60, and poured in a column of high porous polymer HP-20 (60 ml) sold by Mitsubishi Chemical Industries Ltd. The column is washed with water (300 ml) and eluted with methanol. The eluate is concentrated under reduced pressure at room temperature. The residue is dissolved in methanol, treated with active carbon, and concentrated under reduced pressure to give 7β(α-p-hydroxyphenyl-α-carboxyacetamido)-7β- methoxy-3-(1-methyl-tetrazol-5-yl)thiomethyl1-oxadethia-3-cephem-4- carboxylic acid as powder (595 mg) decomposing at 125°C to 132°C. Yield: 88.5%.
    To a solution of 7β(α-p-hydroxyphenyl-α-carboxyacetamido)-7α-methoxy-3-(1- methyl-tetrazol-5-yl)thiomethyl1-oxadethia-3-cephem-4-carboxylic acid (359 mg) in methanol (7 ml) is added a solution of sodium 2-ethylhexanoate in methanol (2 mols/liter; 1.73 ml) at room temperature. After stirring for 10 minutes, the reaction mixture is diluted with ethyl acetate, stirred for 5 minutes, and filtered to collect separated solid, which is washed with ethyl acetate, and dried to give disodium salt of 7β(α-p-hydroxyphenyl-α- carboxyacetamido)-7α-methoxy-3-(1-methyl-tetrazol-5-yl)thiomethyl1- oxadethia-3-cephem-4-carboxylic acid (342 mg). Yield: 888%. Colorless powder. MP decomposition from 170°C.
  • brand nameMoxam (Lilly).
  • Therapeutic Function Antiinfective
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