356789-91-8Relevant academic research and scientific papers
The synthetic development of the anti-influenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu): A challenge for synthesis & process research
Abrecht, Stefan,Harrington, Peter,Iding, Hans,Karpf, Martin,Trussardi, Rene,Wirz, Beat,Zutter, Ulrich
, p. 621 - 629 (2007/10/03)
The evolution of the synthesis of oseltamivir phosphate (Tamiflu), used for the oral treatment and prevention of influenza virus infections (viral flu) is described. Oseltamivir phosphate is the ethyl ester prodrug of the corresponding acid, a potent and selective inhibitor of influenza neuraminidase. The discovery chemistry route and scalable routes used for kilo laboratory production as well as the technical access to oseltamivir phosphate from (-)-shikimic acid proceeding via a synthetically well-developed epoxide building block followed by azide transformations are reviewed. Synthesis and process research investigations towards azide-free conversions of the key epoxide building block to oseltamivir phosphate are discussed. The search for new routes to oseltamivir phosphate independent of shikimic acid including Diels-Alder approaches and transformations of aromatic rings employing a desymmetrization concept are presented in view of large-scale production requirements.
Process for the preparation fo 4,5-diamino shikimic acid derivatives
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, (2008/06/13)
The invention provides a multistep synthesis for the preparation of 4,5-diamino shikimic acid derivatives of formula wherein R1, R2, R3 and R4 are defined in the specification, starting from furan. 4,5-Diamino s
