Description
Cefpirome sulfate is a new injectable cephalosporin indicated for the treatment of
severe urinary and respiratory tract infections, including septicemia and nosocomial
infections. Cefpirome sulfate is reported to be the first true fourth-generation
cephalosporin due to its similar activities to third-generation antibiotics against
Gram-positive bacteria and to first-generation antibiotics against Gram-negative
bacteria. Its efficacy against P.aeruginosa is comparable to ceftazidime. The broad
spectrum of activity includes Klebsiella, methicillin-sensitive staphylococci,
penicillin-resistant pneumococci, E.coli which generates extended-spectrum
beta-lactamases and multi-resistant organisms such as Citrobacter, Enterobacter and
Serratia.
Chemical Properties
White Crystalline Powder
Originator
Hoechst AG (Germany)
Uses
A fourth generation cephalosporin antibiotic
Definition
ChEBI: Cefpirome sulfate is an azaheterocycle sulfate salt. It is functionally related to a cefpirome.
brand name
Cefrom (Hoechst-Roussel).
Synthesis
The present invention employs a microwave-assisted synthesis method to synthesize cefpirome hydrogensulfate in the following steps: (1) 7-aminocephalosporanic acid (2.72 g, 0.01 mol, Compound I) was mixed homogeneously with (Z)-S-2-benzothiazolyl-2-amino-alpha-(methoxyimino)-4-thiazole thioacetate (AEMA, 3.85 g, 0.011 mol, Compound VII) was homogeneously mixed and ground, followed by the addition of 2,3-cyclopentenopyridine (2.3 g, 0.011 mol, Compound IV) and concentrated sulfuric acid (10.88 g, 98 wt%). (2) The microwave reaction was carried out sequentially: 300 W for 1 min, 450 W for 1 min and 750 W for 2 min. (3) After completion of the reaction, deionized water (29.92 g) was added to the residue, mixed and filtered, the filtrate was collected and the solvent was removed to obtain a white solid. The resulting solid was dried under vacuum at 50 °C for 4 h. Cefpirome hydrogen sulfate (5.09 g, yield 99.0%, purity ≥99.9%) was finally obtained.
References
[1] Patent: CN105646542, 2016, A. Location in patent: Paragraph 0027; 0040; 0041; 0042; 0043; 0044; 0045
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