36923-21-4Relevant articles and documents
Ceftibuten: Development of a commercial process based on cephalosporin C. Part III. Process for the conversion of 3-exomethylene-7(R)-glutaroylaminocepham-4-carboxylic acid 1(S)-oxide to Ceftibuten
Bernasconi, Ermanno,Lee, Junning,Sogli, Loris,Walker, Derek
, p. 169 - 177 (2002)
The foregoing papers (Bernasconi, E.; Lee, J.; Roletto, J.; Sogli, L.; Walker, D. Org. Process Res. Dev. 2002, 6, 152 and Bernasconi, E.; Genders, D.; Lee, J.; Longoni, D.; Martin, C. R.; Menon, V.; Roletto, J.; Sogli, L.; Walker, D.; Zappi, G.; Zelenay, P.; Zhang, H. Org. Process Res. Dev. 2002, 6, 158) describe a high-yielding, all-aqueous process for the preparation of 3-exomethylene-7(R)-glutaroylaminocepham-4-carboxylic acid 1(S)-oxide (3) from fermented cephalosporin C broth via enzyme transformations and electrochemical reduction without isolation of any precursors. In this paper we describe the efficient recovery of 3 from aqueous solution, by extractive esterification employing diphenyldiazomethane, and the conversion of the obtained bis(diphenylmethyl) ester (4) into intermediates both for Ceftibuten (1) and cefaclor (8). Several routes to the key Ceftibuten building block, diphenylmethyl 7(R)-aminoceph-3-em-4-carboxylate (6) are described. This key building block is acylated, deblocked, and purified using chemistry described by Shionogi workers to give Ceftibuten.
Synthesis and in Vitro Evaluation of New Cephalosporins Exhibiting Antimicrobial Activity Against Gram-Positive Bacteria, in Particular Methicillin-Resistant Staphylococci
Lin, Ho-Shen,Rampersaud, Ashraff A.,Flokowitsch, Jane E.,Alborn, William E.,Wu, Ernie C. Y.,Preston, David A.
, p. 833 - 846 (2007/10/03)
The preparation and biological evaluation of 7β-acetamido>cephalosporins and 7β-acetamido>cephalosporins, 9a-o, substituted at the 3-position with acetyloxymethyl, chlorine, hydrogen, and methyl are described.Hantzsch's thiazole synthesis is employed to provide thiazoleacetic acids 5a-e, subsequently followed by Morpho CDI-assisted amidation to complete the synthesis of target cephalosporins 9a-o.These compounds display activity selectively against Gram-positive bacteria, but are inactive against most Gram-negative bacteria tested.Those with acetyloxymethyl at the 3-position, i.e., 9a, 9e, 9i, 9m, and 9o, exhibit activity with minimal inhibitory concentrations of 16 μg/mL or lower against four strains of methicillin-resistant staphylococci, namely Staphylococcus aureus X400 and S13E and Staphylococcus epidermidis 270 and 222.Notably, 9a displays an activity profile similar to that of vancomycin regarding its spectrum and potency.Key Words: Gram-positive bacteria; Methicillin-resistant staphylococci; Cephalosporin; Thiazole synthesis; Amidation.
Production of 3-allyl- and 3-butenyl-3-cephems
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, (2008/06/13)
There is disclosed a process for the production of certain 2-allyl- and 3-butenyl-3-cephem derivatives by coupling a 3-chloromethyl-3-cephem with a hydrocarbyltributystannane in the presence of bis(dibenzylideneacetonyl)-palladium and a phosphine. The 3-allyl- and 3-butenyl-3-cephem derivatives so-produced are useful as broad-spectrum antibacterial agents.
7β-Amino-cepham-3-ol-4-carboxylic acid compounds
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, (2008/06/13)
The invention concerns 7β-amino-cepham-3-ol-4-carboxylic acid compounds, particularly esters thereof, and the N-substituted, especially N-acylated derivatives of such compounds, as well as the 3-O-esters of these compounds. They can be used as intermediates, for example, for the manufacture of the corresponding 3-unsubstituted 7β-amino-3-cephem-4-carboxylic acid compounds, which show outstanding pharmacological effects.
