- CEPHEM COMPOUNDS WITH LATENT REACTIVE GROUPS AND METHODS OF USING AND MAKING SAME
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The present application provides novel cephem, penem, and monobactam compounds that exhibit antibiotic activity against both Gram-negative and Gram-positive bacteria, as well as compositions comprising these compounds and methods of using these compounds and compositions to treat bacterial infections.
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Paragraph 0330; 0334-0335
(2020/10/19)
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- A method for preparing cephalosporin lorraine ester
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The invention relates to a synthetic method for ceftaroline fosamil. According to the synthetic method, 7-phenylacetamide-3-hydroxy-3-cephalosporin-4-carboxylate-diphenylmethyl is selected as a raw material to be chloridized and reacts with 4-(4-pyridyl)-1,3-thiazole-2-thiol sodium salt at a C-3 site to obtain a thioether compound, p-cresol and immobilized penicillinase are adopted for removing carboxyl and amino protecting groups respectively, the thioether compound and the acylated AE-active ester are subjected to C-7 site condensation reaction, and crystallization in acetic acid is performed after hydrolyzation to prepare the ceftaroline fosamil successfully. The preparation method has the advantages that use of toxic and harmful substances such as trifluoroacetic acid and phosphorus pentachloride is avoided, reaction conditions are moderate, side reactions are few, technology is simple, yield and product purity are high, cost is low, raw materials are cheap and easy to obtain, and the preparation method is applicable to industrial production.
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Paragraph 0036; 0037; 0038; 0049; 0050; 0051
(2017/08/25)
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- Cephalosporin-derived inhibitors of beta-lactamase. Part 4: The C3 substituent.
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New C3-substituted beta-lactamase inhibitors were prepared and evaluated against representative class A and class C enzymes. It was possible to improve simultaneous inhibitory activity of both classes of serine hydrolase. Other inhibitors showed high selectivity for either the class C cephalosporinases or the class A penicillinases. This represents the first time that cephalosporin-derived inhibitors have demonstrated selectivity for the class A beta-lactamases.
- Buynak, John D,Vogeti, Lakshminarayana,Doppalapudi, Venkata Ramana,Solomon, George Martin,Chen, Hansong
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p. 1663 - 1666
(2007/10/03)
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- Process for preparing allenyl beta-lactam derivatives
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An allenyl β -lactam compound is prepared by reacting the hydroxyl group of a starting β-lactam compound with a reactive functional group derivative of sulfonic acid and reacting the resulting β -lactam compound with a tertiary organic base to obtain an a
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- Process for preparing halogenated cephem derivatives
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A 3-halogenated cephem derivative is prepared by causing a halogenating reagent to act on an allenyl β -lactam compound in the presence of a sulfinate ion or thiolate ion capturing agent to obtain the 3-halogenated cephem derivative.
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- Reductive cross-coupling of 3-substituted Δ3-cephems with alkenyl halides in an Al/PbBr2/NiBr2(bpy) triplemetal redox system. Synthesis of 3-alkenyl-Δ3-cephems
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Synthesis of 3-alkenyl-Δ3-cephems was performed successfully by cross-coupling 3-(trifluoromethylsulfonyloxy or chloro)-Δ3-cephem with alkenyl halides, e.g., vihyl bromide, trans-1-bromo-1-propene, and trans-β-bromostyrene in an Al/cat·PbBr2/cat·NiBr2(bpy)/NMP (or DMF) system. Reduction of 3-(trifluoromethylsulfonyloxy)-Δ3-cephem into norcephalosporin was also achieved by a similar reaction in the presence of 5 molar equiv of water. Scope and a plausible mechanism of the Al/Pb/Ni triplemetal-redox promoted reactions are discussed.
- Tanaka,Zhao,Kumase
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p. 570 - 577
(2007/10/03)
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- Discovery of RWJ-54428 (MC-02,479), a new cephalosporin active against resistant gram-positive bacteria
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The discovery of RWJ-54428 (MC-02,479), a new cephalosporin displaying promising activity against sensitive and resistant Gram-positive bacteria, is described. Progressive structural modification from the previously reported 3-phenylthiocephem MC-02,331 afforded an overall increase in potency against MRSA while retaining other key properties such as acceptable solubility and serum binding. Evaluation of the in vitro potency and in vivo efficacy of a series of closely related compounds resulted in selection of RWJ-54428 (MC-02,479) for further studies.
- Hecker,Glinka,Cho,Zhang,Price,Chamberland,Griffith,Lee
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p. 1272 - 1281
(2007/10/03)
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- Synthesis and antibacterial activities of new (α-hydrazinobenzyl)cephalosporins
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Some (α-hydrazinobenzyl)cephalosporins, structurally related to cephalexin, cephaloglycin, and cefaclor have been prepared and evaluated in vitro for their antimicrobial activity. The synthesis involves the condensation of the chloride hydrochloride with
- Balsamo, A.,Macchia, B.,Macchia, F.,Rossello, A.,Giani, R.,et al.
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p. 1648 - 1650
(2007/10/02)
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- 7-(Substituted methyl)-3-(substituted thio)-cephalosporins, derivatives and pharmaceutical compositions containing them
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Disclosed are antibiotic 3-(substituted thio)-7-(substituted methyl) cephalosporins, derivatives and analogues thereof; wherein the methyl substituent is, inter alia, hydroxyl, ketonic oxygen, imino nitrogen, amino or mercapto. Also disclosed are processes for the preparation of such compounds and their pharmaceutically acceptable salt, ester and amide derivatives; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
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- 3-(Substituted thio) cephalosporins, derivatives and nuclear analogues thereof
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Disclosed is a class of cephalosporins including the carba, aza and oxa nuclear analogues thereof which bear at the 3-position a substituted thio substituent; such compounds are useful as antibiotics. Also disclosed are processes for the preparation of su
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