Tamiflu - Oseltamivir phosphate

Figure 4.18 The structure of Tamiflu (oseltamivir phosphate), an antiviral agent active against type A influenza, and a molecular model of its minimum-energy conformation, as calculated by molecular mechanics.

Tamiflu (Oseltamivir phosphate). Roche Pharmaceuticals. US Prescribing information, July 2007,... 

A highly useful and important regioselective reduction of substrate 84 leads to a mixture of 3-hydroxy ethers 85 and 86 in a 32 1 ratio (Eq. 306). Compound 85 is further converted to the anti-influenza drug oseltamivir phosphate, better known as Tamiflu .498... 

The neuramidase inhibitor oseltamivir phosphate was discovered by Gilead Sciences and developed by Roche Pharmaceuticals under the name of Tamiflu (Scheme 5.13) to be used as an orally active antiviral compound for prevention and treatment of influenza infections. Because of the recent emergence of the avian flu, the demand for Tamiflu has gained momentum. Two industrially feasible syntheses are known, starting from (—)-shikimic acid and (—)-quinic acid, respectively (Scheme 5.13) [45]. 

NEURAMINIDASE INHIBITORS FOR INFLUENZA OSELTAMIVIR PHOSPHATE (TAMIFLU ) AND ZANAMIVIR (RELENZA )... 

Ghosh, G.C., Nakada, N., Yamashita, N. and Tanaka, H. (2010) Oseltamivir carboxylate, the active metabolite of oseltamivir phosphate (Tamiflu), detected in sewage discharge and river water in Japan. Environ. Health Perspect., 118 (1), 103-107. 

S. Abrecht, P. Harrington, H. Iding, M. Karpf, R. Trussardi, B. Wirz, and U. Zutter, The synthetic development of the anti-influenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu) A challenge for synthesis process research, Chimia, 58 (2004) 621-929. 

Karpf, M. et al. New, Azide-Free Transformation of Epoxides into 1,2-Diamino Compounds Synthesis of the Anti-Influenza Neuraminidase Inhibitor Oseltamivir Phosphate (Tamiflu). 3.4.4 2001 [135]... 

Oseltamivir phosphate http //www.tamiflu.com/Roche also recommends Tamiflu for treating patients over one year old. See also www.fda.gov/cder/drug/infopage/tamiflu/default.htm... 

Oseltamivir came on the market in 2000 under the name of Tamiflu 36, which is the phosphate salt of the ethyl ester prodrug [86]. Oseltamivir phosphate is well absorbed in the G1 tract and can therefore be administered orally. Approximately 80% of an oral dose reaches... 

Oseltamivir phosphate (Tamiflu ) was developed for the treatment and prevention of influenza virus infections. The key starting material of one commercial route is... 

In pursuit of a rapid and cost-effective synthesis of the anti-influenza drug (—)-oseltamivir (83) (Tamiflu , as phosphate), Hayashi and coworkers have developed an innovative synthesis involving three one-pot processes (Scheme 7.15) [56]. A large-scale synthesis of Tamiflu is considered so profoundly important today with... 

Influenza A viruses cause severe infections in the respiratory system and are responsible for seasonal epidemics and sporadic pandemics. The primary method for prevention is through vaccination but vaccine production by current methods cannot be carried out in time to stop the progress of a new strain of the influenza virus. Therefore, effective antiviral agents are used for prophylactic and therapeutic treatments. Among several viral molecular targets for anti-influenza drugs, the surface glycoprotein neuraminidase appears particularly attractive. Selective inhibitors of this enzyme have been developed and two of which, oseltamivir phosphate 18 (Tamiflu ) " and zanamivir 19 (Relenza ), have been approved for human use (Scheme 6). 

Scheme 6 Structure of the potent neuraminidase inhibitors oseltamivir phosphate 18 (Tamiflu ) and zanamivir 19 (Relenza ).

Oseltamivir phosphate (24, Tamiflu ), a neuraminidase inhibitor, is administered orally for the treatment and prevention of influenza A and B virus infections, and stockpiling of this drug has been proposed to counter the threat of a pandemic such as avian flu [63,64]. One synthesis... 

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