A method for the synthesis of an oseltamivir PET tracer

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 2, 2008, Pages 600-602

  Morita, Masataka ^a   Sone, Toshihiko ^a   Yamatsugu, Kenzo ^a   Sohtome, Yoshihiro ^a   Matsunaga, Shigeki ^a   Kanai, Motomu ^a   Watanabe, Yasuyoshi ^b   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b RIKEN   (Japan)

Author keywords

Acetylation; Influenza; Neuroexcitatory effects; Oseltamivir; Positron emission tomography (PET)

Indexed keywords

ACETIC ACID DERIVATIVE; AMINE; OSELTAMIVIR; TRACER;

ACETYLATION; ANALYTIC METHOD; ARTICLE; DEPROTECTION REACTION; DRUG SYNTHESIS; POSITRON EMISSION TOMOGRAPHY;

ANIMALS; ANTIVIRAL AGENTS; OSELTAMIVIR; POSITRON-EMISSION TOMOGRAPHY; RADIOISOTOPES;

EID: 38149121471     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.11.079     Document Type: Article

References (27)

1. Kim C.U., Lew W., Williams M.A., Liu H., Zhang L., Swaminathan S., Bischofberger N., Chen M.S., Mendel D.B., Tai C.Y., Laver W.G., and Stevens R.C. J. Am. Chem. Soc. 119 (1997) 681
2. Ward P., Small I., Smith J., Suter P., and Dutkowski R.J. Antimicrob. Chemother. 55 (2005) 5
3. Abrecht S., Harrington P., Iding H., Karpf M., Trussardi R., Wirz B., and Zutter U. Chimia 58 (2004) 621
4. For a recent review of oseltamivir syntheses, see:. Farina V., and Brown J.D. Angew. Chem., Int. Ed. 45 (2006) 7330
5. Yeung Y.-Y., Hong S., and Corey E.J. J. Am. Chem. Soc. 128 (2006) 6310
6. Fukuta Y., Mita T., Fukuda N., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 128 (2006) 6312
7. Mita T., Fukuda N., Roca F.X., Kanai M., and Shibasaki M. Org. Lett. 9 (2007) 259
8. Yamatsugu K., Kamijyo S., Suto Y., Kanai M., and Shibasaki M. Tetrahedron Lett. 48 (2007) 1403
9. Sato N., Akiba T., Yokoshima S., and Fukuyama T. Angew. Chem., Int. Ed. 46 (2007) 5734
10. Bromfield K.M., Graden H., Hagberg D.P., Olsson T., and Kann N. Chem. Commun. (2007) 3183
11. Shie J., Fang J., Wang S., Tsai K., Cheng Y., Yang A., Hsiao S., Su C., and Wong C. J. Am. Chem. Soc. 129 (2007) 11892
12. Izumi Y., Tokuda K., O'Dell K.A., Zorumski C.F., and Narahashi T. Neurosci. Lett. 426 (2007) 54
13. Ishii, K.; Hamamoto, H.; Sasaki, T.; Ikegaya, Y.; Yamatsugu, K.; Kanai, M.; Shibasaki, M.; Sekimizu, K. Drug Discov. Ther., in press.
14. According to the Ministry of Health, Labor, and Welfare of Japan, however, based on animal experiments performed by the Chugai Pharmaceutical Company, which sells Tamiflu in Japan, there is no relationship between Tamiflu administration and abnormal behavior (stated as a tentative conclusion on October 24, 2007).
15. Morimoto K., Nakakariya M., Shirasaka Y., Kakinuma C., Fujita T., Tamai I., and Ogihara T. Drug Metab. Dispos. 35 (2007) 10.1124/dmd.107.017699
16. Ose A., Kusuhara H., Yamatsugu K., Kanai M., Shibasaki M., Fujita T., Yamamoto A., and Sugiyama Y. Drug Metab. Dispos. 35 (2007) 10.1124/dmd.107.018556
17. For recent reviews, see:. Wood K.A., Hoskin P.J., and Saunders M.I. Clin. Oncol. 19 (2007) 237
18. Welsh J.S. Am. J. Clin. Oncol. 30 (2007) 437
19. 11COCl in PET studies, see:. Le Bars D., Luthra S.K., Pike V.W., and Duc C.Luu. Appl. Rad. Isotop. 38 (1987) 1073
20. Courtyn J., Cornelissen B., Oltenfreiter R., Vandecapelle M., Slegers G., and Strijckmans K. Nucl. Med. Biol. 31 (2004) 649
21. Chen J.J., Fiehn-Schulze B., Brough P.A., Snieckus V., and Firnau G. Appl. Rad. Isotop. 49 (1998) 1573
22. Sasaki T., Furukata K., Ishii S., Iimori T., Ikegami S., Nozaki T., and Senda M. J. Labelled Compd. Radiopharm. 38 (1996) 337
23. Bonnot-Lours S., Crouzel C., Prenant C., and Hinnen F. J. Labelled Compd. Radiopharm. 33 (1993) 277
24. Oberdorfer F., Siegel T., Guhlmann A., Keppler D., and Maier-Borst W. J. Labelled Compd. Radiopharm. 31 (1992) 903
25. Banks W.R., Tewson T.J., and Digenis G.A. Appl. Rad. Isotop. 41 (1990) 719
26. 3COCl was used in this study.
27. 2/MeOH = 7:1) to afford 4 (13.8 mg, 82%) as a colorless oil.