108260-04-4Relevant academic research and scientific papers
Preparation method of cefalexin
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Paragraph 0048-0051, (2020/05/05)
The invention belongs to the field of medicine synthesis, in particular to an improved method of a beta-lactam antibiotic cefalexin synthesis process. According to the method, 7-ADCA is used as a rawmaterial and is protected by carboxyl silane; after activation with alpha-aminophenylacetic acid hydrochloride and trifluoroacetic acid succinimide, condensation reaction is carried out; cefalexin isobtained through hydrolysis after-treatment, the proper pH value is controlled through hydrochloric acid after organic solvent and alkali adjustment treatment, and cefalexin crystals with extremely high purity are obtained. The method has the advantages of being easy and convenient to operate, mild in reaction condition, not prone to causing side reaction and capable of effectively removing impurities and preparing high-purity cefalexin.
PROCESS FOR THE PRODUCTION OF CEPHALOSPORINS
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Page/Page column 12, (2012/03/27)
The present invention relates to a composition comprising ≥85 wt% of an N-deacylated cephalosporin, a process for making the same and the use of said N-deacylated cephalosporin in the preparation of highly pure semi synthetic cephalosporins.
MANUFACTURING METHOD AND APPARATUS OF ULTRAFINE PARTICLES HAVING UNIFORM PARTICLE SIZE DISTRIBUTION
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, (2011/09/14)
The present invention relates to a novel technology for forming fine particles with a size of 0.02?3 microns from a solid that can be dissolved in a liquid solvent and is not decomposed by heat. The particle preparation technology according to the present invention may be applicable to the fields of food, cosmetics, biopolymer, polymer compositions, and pharmaceuticals.
Amino ester hydrolase from Xanthomonas campestris pv. campestris, ATCC 33913 for enzymatic synthesis of ampicillin
Blum, Janna K.,Bommarius, Andreas S.
experimental part, p. 21 - 28 (2010/12/19)
α-Amino ester hydrolases (AEH) are a small class of proteins, which are highly specific for hydrolysis or synthesis of α-amino containing amides and esters including β-lactam antibiotics such as ampicillin, amoxicillin, and cephalexin. A BLAST search revealed the sequence of a putative glutaryl 7-aminocephalosporanic acid (GL-7-ACA) acylase 93% identical to a known AEH from Xanthomonas citri. The gene, termed gaa, was cloned from the genomic DNA of Xanthomonas campestris pv. campestris sp. strain ATCC 33913 and the corresponding protein was expressed into Escherichia coli. The purified protein was able to perform both hydrolysis and synthesis of a variety of α-amino β-lactam antibiotics including (R)-ampicillin and cephalexin, with optimal ampicillin hydrolytic activity at 25 °C and pH 6.8, with kinetic parameters of kcat of 72.5 s-1 and KM of 1.1 mM. The synthesis parameters α, βo, and γ for ampicillin, determined here first for this class of proteins, are α = 0.25, βo = 42.8 M-1, and γ = 0.23, and demonstrate the excellent synthetic potential of these enzymes. An extensive study of site-directed mutations around the binding pocket of X. campestris pv. campestris AEH strongly suggests that mutation of almost any first-shell amino acid residues around the active site leads to inactive enzyme, including Y82, Y175, D207, D208, W209, Y222, and E309, in addition to those residues forming the catalytic triad, S174, H340, and D307.
Synthesis of cephalosporin-type antibiotics by coupling of their β-lactam nucleus and racemic amino acid side chains using a clathration-induced asymmetric transformation
Kemperman, Gerardus J.,Zhu, Jie,Klunder, Antonius J. H.,Zwanenburg, Binne
, p. 1817 - 1820 (2007/10/03)
The cephalosporin-type antibiotics Cephalexin, Cephradine and Cefadroxil have been prepared by coupling of their β-lactam nucleus and racemic amino acid side chain precursors. The initially obtained mixture of cephalosporin epimers is subjected to a clathration-induced asymmetric transformation which results in the epimerization of the epi-cephalosporin into the cephalosporin with the correct diastereomeric configuration.
Process and device for producing liquid dosage formulations of medicinal compounds on demand from tablets and capsules
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, (2008/06/13)
The present invention provides a process for preparing liquid pharmaceutical formulations on demand from tablets and capsules.
Complexes of cephalosporins and carbacephalosporins with parabens
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, (2008/06/13)
The invention provides complexes of the formula: STR1 wherein X is chloro, hydrogen, vinyl, or --CH3, Z is CH2 or S; n is 0-5; Y is phenyl or 1,4-cyclohexadien-1-yl; R1 and R2 are hydrogen or hydroxy, with the proviso that R1 and R2 are not both hydrogen and R3 is --COO-, --COO(C1 -C4 alkyl), --NO2 or STR2 wherein R4 is C1 -C4 alkyl.
Penicillin acylase in the industrial production of β-lactam antibiotics
Brugging, Alle,Roos, Eric C.,De Vroom, Erik
, p. 128 - 133 (2013/09/08)
Immobilized penicillin acylase is a biocatalyst suitable for the kinetically controlled industrial synthesis of semi-synthetic antibiotics in aqueous environments. Amoxiciliin and ampicillin are obtained by condensing 6-aminopenicillanic acid with the amide or ester of D-( - )-4-hydroxyphenyIglycine and D-( - )phenylglycine, respectively. Similarly, the cephalosporin antibiotics cefadroxil and cephalexin can be obtained from 7-aminodesacetoxycephalosporanic acid.
Synthesis of potential impurities of cefalexin and cefradine
Hendrix,Roets,Bervoets,Thomas,Pijcke,Busson,Janssen,Hoogmartens
, p. 215 - 219 (2007/10/02)
The synthesis of some impurities of the cephalosporin antibiotics cefalexin and cefradine is described. These impurities which may be present in commercial samples are formed during the semi-synthetic preparation of these antibiotics or upon their degradation. The preparation of these compounds enables the validation of selective quantitative analytical methods, such as column liquid chromatography and thin layer chromatography.
Prodrug derivatives of carboxylic acid drugs
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, (2008/06/13)
Novel ester derivatives of carboxylic acid medicaments of formula (I), wherein R--COO--represents the acyloxy residue of a carboxylic acid drug or medicament, n is an integrer from 1 to 3, and R1 and R2 are the same or different and are selected from a group consisting of an alkyl, an alkenyl, an aryl, an aralkyl, a cycloalkyl and which group may be unsubstituted or substituted, or R1 and R2 together with the N forms a 4-, 5-, 6- or 7-membered heterocyclic ring, which in addition to the nitrogen atom may contain one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and which heterocyclic group may be substituted. These compounds are highly biolabile prodrug forms of the corresponding carboxylic acid compounds and are highly susceptible to undergoing enzymatic hydrolysis in vivo whereas they are highly stable in aqueous solution. The novel derivatives are less irritating to mucosa than the parent carboxylic acids and may provide an improved bio-availability of the drugs.
