Synthesis and Characterization of Potential Pharmacopeial Impurities of Oseltamivir: An Antiviral Drug

Rajasekhar Ponduri; Pramod Kumar; Lakshmana Rao Vadali; Komaraiah Aelugu; Kishore Matcha

doi:10.14233/ajchem.2018.21376

Issue

Vol. 30 No. 9 (2018): Vol 30 Issue 9

Issue Published : July 31, 2018

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Characterization of Potential Pharmacopeial Impurities of Oseltamivir: An Antiviral Drug

https://doi.org/10.14233/ajchem.2018.21376

Rajasekhar Ponduri

Mylan Laboratories Limited, Bollaram, Jinnaram (Mandal), Medak-502 325, India; Jawaharlal Nehru Technological University-Hyderabad, College of Engineering, Centre for Chemical Sciences & Technology, Institute of Science and Technology, Kukatpally, Hyderabad-500 085, India

Pramod Kumar

Jawaharlal Nehru Technological University-Hyderabad, College of Engineering, Centre for Chemical Sciences & Technology, Institute of Science and Technology, Kukatpally, Hyderabad-500 085, India

Lakshmana Rao Vadali

Mylan Laboratories Limited, Bollaram, Jinnaram (Mandal), Medak-502 325, India

Komaraiah Aelugu

Mylan Laboratories Limited, Bollaram, Jinnaram (Mandal), Medak-502 325, India

Kishore Matcha

Mylan Laboratories Limited, Bollaram, Jinnaram (Mandal), Medak-502 325, India

Corresponding Author(s) : Rajasekhar Ponduri

rajasekharponduri123@gmail.com

Asian Journal of Chemistry, Vol. 30 No. 9 (2018): Vol 30 Issue 9
Article Published : July 31, 2018

Abstract

Impurities of oseltamivir phosphate were synthesized from chiral epoxide (1) in a simpler and much feasible synthetic approach in seven steps accounting to 8.2 % overall yield. The nucleophilic addition of N₃ (highly regioselective and stereoselective) in the first and third stage of the synthesis has been tailored and the reaction conditions were optimized.

Keywords

Oseltamivir Impurities Antiviral Aziridine

Ponduri, R., Kumar, P., Vadali, L. R., Aelugu, K., & Matcha, K. (2018). Synthesis and Characterization of Potential Pharmacopeial Impurities of Oseltamivir: An Antiviral Drug. Asian Journal of Chemistry, 30(9), 2003–2007. https://doi.org/10.14233/ajchem.2018.21376

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References

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K. Ungchusak, P. Auewarakul, S.F. Dowell, R. Kitphati, W. Auwanit, P. Puthavathana, M. Uiprasertkul, K. Boonnak, C. Pittayawonganon, N.J. Cox, S.R. Zaki, P. Thawatsupha, M. Chittaganpitch, R. Khontong, J.M. Simmerman and S.N. Chunsutthiwat, Engl. J. Med., 352, 333 (2005); https://doi.org/10.1056/NEJMoa044021.

A.N. Moscona, Engl. J. Med., 353, 1363 (2005); https://doi.org/10.1056/NEJMra050740.

E.D. Clercq, Nat. Rev. Drug Discov., 5, 1015 (2006); https://doi.org/10.1038/nrd2175.

E.D. Clercq, Nat. Rev. Microbiol., 2, 704 (2004); https://doi.org/10.1038/nrmicro975.

H.J. Schünemann, S.R. Hill, M. Kakad, R. Bellamy, T.M. Uyeki, F.G. Hayden, Y. Yazdanpanah, J. Beigel, T. Chotpitayasunondh, C. Del Mar, J. Farrar, T.T. Hien, B. Özbay, N. Sugaya, K. Fukuda, N. Shindo, L. Stockman, G.E. Vist, A. Croisier, A. Nagjdaliyev, C. Roth, G. Thomson, H. Zucker and A.D. Oxman, Lancet Infect. Dis., 7, 21 (2007); https://doi.org/10.1016/S1473-3099(06)70684-3.

J. Kongkamnerd, L. Cappelletti, A. Prandi, P. Seneci, T. Rungrotmongkol, N. Jongaroonngamsang, P. Rojsitthisak, V. Frecer, A. Milani, G. Cattoli, C. Terregino, I. Capua, L. Beneduce, A. Gallotta, P. Pengo, G. Fassina, S. Miertus and W. De-Eknamkul, Bioorg. Med. Chem., 20, 2152 (2012); https://doi.org/10.1016/j.bmc.2012.01.026.

L.-D. Nie, X.-X. Shi, K.H. Ko and W.-D. Lu, J. Org. Chem., 74, 3970 (2009); https://doi.org/10.1021/jo900218k.

M. Federspiel, R. Fischer, M. Hennig, H.-J. Mair, T. Oberhauser, G. Rimmler, T. Albiez, J. Bruhin, H. Estermann, C. Gandert, V. Göckel, S. Götzö, U. Hoffmann, G. Huber, G. Janatsch, S. Lauper, O. Röckel-Stäbler, R. Trussardi and A.G. Zwahlen, Org. Process Res. Dev., 3, 266 (1999); https://doi.org/10.1021/op9900176.

S. Abrecht, P. Harrington, H. Iding, M. Karpf, R. Trussardi, B. Wirz and U. Zutter, Chimia, 58, 621 (2004); https://doi.org/10.2533/000942904777677605.

L.D. Nie, X.X. Shi, N. Quan, F.F. Wang and X. Lu, Tetrahedron Asymm., 22, 1692 (2011); https://doi.org/10.1016/j.tetasy.2011.09.014.

S. Raghavan and V.S. Babu, Tetrahedron, 67, 2044 (2011); https://doi.org/10.1016/j.tet.2011.01.064.

L.D. Nie, W. Ding, X.X. Shi, N. Quan and X. Lu, Tetrahedron Asymm., 23, 742 (2012); https://doi.org/10.1016/j.tetasy.2012.05.014.

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A.I. Kalashnikov, S.V. Sysolyatin, G.V. Sakovich, E.G. Sonina and I.A. Shchurova, Russ. Chem. Bull., 62, 163 (2013); https://doi.org/10.1007/s11172-013-0024-2.

N.-G. Li, Z.-H. Shi, Y.-P. Tang, Q.-P. Shi, W. Zhang, P.-X. Zhang, Z.-X. Dong, W. Li, J.-A. Duan, K. Pratsch, R. Wellhausen and H. Seitz, Curr. Org. Chem., 18, 16 (2014); https://doi.org/10.1016/j.cbpa.2013.10.024.

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P. Laborda, S.-Y. Wang and J. Voglmeir, Molecules, 21, 1513 (2016); https://doi.org/10.3390/molecules21111513.

Y. Xie, D. Xu, B. Huang, X. Ma, W. Qi, F. Shi, X. Liu, Y. Zhang and W. Xu, J. Med. Chem., 57, 8445 (2014); https://doi.org/10.1021/jm500892k.

R.M. Neri-Bazán, J. García-Machorro, D. Méndez-Luna, L.E. TolentinoLópez, F. Martínez-Ramos, I.I. Padilla-Martínez, L. Aguilar-Faisal, M.A. Soriano-Ursúa, J.G. Trujillo-Ferrara, M.J. Fragoso-Vázquez, B.L. Barrón and J. Correa-Basurto, Eur. J. Med. Chem., 128, 154 (2017); https://doi.org/10.1016/j.ejmech.2017.01.039.

Z. Wang, L.P. Cheng, X.H. Zhang, W. Pang, L. Li and J.L. Zhao, Bioorg. Med. Chem. Lett., 27, 5429 (2017); https://doi.org/10.1016/j.bmcl.2017.11.003.

S.Q. Wang, X.C. Cheng, W.L. Dong, R.L. Wang and K.C. Chou, Biochem. Biophys. Res. Commun., 401, 188 (2010 https://doi.org/10.1016/j.bbrc.2010.09.020.

International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use, ICH Harmonised Guideline for Elemental Impurities Q3D; Current Step 4 version, 16 December (2014).

H. Osato, I.L. Jones, A. Chen and C.L.L. Chai, Org. Lett., 12, 60 (2010); https://doi.org/10.1021/ol9024716.

J.C. Rohloff, K.M. Kent, M.J. Postich, M.W. Becker, H.H. Chapman, D.E. Kelly, W. Lew, M.S. Louie, L.R. McGee, E.J. Prisbe, L.M. Schultze, R.H. Yu and L. Zhang, J. Org. Chem., 63, 4545 (1998); https://doi.org/10.1021/jo980330q.

R. Oliyai, L.C. Yuan, T.C. Dahl, K.Y. Swaminathan, K.-Y. Wang and W.A. Lee, Pharm. Res., 15, 1300 (1998); https://doi.org/10.1023/A:1011964529805.

M. Junwal, A. Sahu, T. Handa, R.P. Shah and S. Singh, J. Pharm. Biomed. Anal., 62, 48 (2012); https://doi.org/10.1016/j.jpba.2012.01.001.

Issue

Vol. 30 No. 9 (2018): Vol 30 Issue 9

Synthesis and Characterization of Potential Pharmacopeial Impurities of Oseltamivir: An Antiviral Drug

Corresponding Author(s) : Rajasekhar Ponduri

Abstract

Keywords

Full Article

Download Citation

References

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