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Vol. 34 No. 12 (2022): Vol 34 Issue 12, 2022

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An Efficient, Novel Synthetic Route to (R)-Salmeterol Xinafoate and Facile Synthetic Protocols for Preparation of its Process Related Potential Impurities

https://doi.org/10.14233/ajchem.2022.26887
Sathyanarayana Boodida
Department of Chemistry, JNTUH University College of Engineering Jagtial, Jagtial-505501, India
Parandhama Gudla
Department of Chemistry, JNTUH University College of Engineering Jagtial, Jagtial-505501, India ; Chemical Research and Development Division, Prajna Generics Pvt. Ltd., Pragathinagar, Hyderabad-500090, India
Srinivasula Reddy Maddula
Chemical Research and Development Division, Prajna Generics Pvt. Ltd., Pragathinagar, Hyderabad-500090, India

Corresponding Author(s) : Sathyanarayana Boodida

bs14@jntuh.ac.in

Asian Journal of Chemistry, Vol. 34 No. 12 (2022): Vol 34 Issue 12, 2022

Abstract

In present work, an effective, innovative enantioselective synthetic strategy for the synthesis of salmeterol xinafoate and its probable process-related impurities was reported. Seven pharmacopeia specified impurities were synthesized and confirmed by FT-IR, mass, 1H & 13C NMR spectroscopy. With respect to the corresponding retention factors, these contaminants were validated using the available RP-HPLC method. These compounds can be used as a reference standard for the active pharmaceutical ingredient manufactures and research organizations.

Keywords

Salmeterol xinafoate Potential impurities Impurities Long-acting β2-adrenergic agonist (LABA)
Boodida, S., Gudla, P., & Reddy Maddula, S. (2022). An Efficient, Novel Synthetic Route to (R)-Salmeterol Xinafoate and Facile Synthetic Protocols for Preparation of its Process Related Potential Impurities. Asian Journal of Chemistry, 34(12), 3333–3352. https://doi.org/10.14233/ajchem.2022.26887
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References
  1. R.N. Brogden and D. Faulds, Drugs, 42, 895 (1991); https://doi.org/10.2165/00003495-199142050-00010
  2. D.I. Ball, R.T. Brittain, R.A. Coleman, L.H. Denyer, D. Jack, M. Johnson, L.H.C. Lunts, A.T. Nials, K.E. Sheldrick and I.F. Skidmore, Br. J. Pharmacol., 104, 665 (1991); https://doi.org/10.1111/j.1476-5381.1991.tb12486.x
  3. M. Johnson, P.R. Butchers, R.A. Coleman, A.T. Nials, P. Strong, M.J. Summer, C.J. Vardey and C.J. Whelan, Life Sci., 52, 2131 (1993); https://doi.org/10.1016/0024-3205(93)90728-L
  4. M. Johnson, Paediatr. Respir. Rev., 2, 57 (2001); https://doi.org/10.1053/prrv.2000.0102
  5. C.W. Bierman, J.P. Kemp and M.J. Sharpe, J. Allergy Clin. Immunol., 85, 198 (1990).
  6. A.A. Verberne, W.C. Hop, A.B. Bos and K.F. Kerrebijn, J. Allergy Clin. Immunol., 91, 127 (1993); https://doi.org/10.1016/0091-6749(93)90305-Y
  7. B. Lundback, D.W. Rawlinson and J.B. Palmer, Thorax, 48, 148 (1993).
  8. P. Wilding, J. Thompson-Coon J and M. Clark, Thorax, 50, A39 (1995).
  9. G.G. Meijer, D.S. Postma, P.G. Mulder and W.M. Van Aalderen, Am. J. Respir. Crit. Care Med., 152, 1887 (1995); https://doi.org/10.1164/ajrccm.152.6.8520751
  10. S.P. Newman, G. Woodman, S.W. Clarke and M.A. Sackner, Am. Rev. Respir. Dis., 131, A96 (1985).
  11. N.A. Hanania, P. Darken, D. Horstman, C. Reisner, B. Lee, S. Davis and T. Shah, Chest, 124, 834 (2003); https://doi.org/10.1378/chest.124.3.834
  12. N. Svedmyr and C.G. Lofdahl, Pharmacol. Toxicol., 78, 3 (1996); https://doi.org/10.1111/j.1600-0773.1996.tb00172.x
  13. G. Shapiro, W. Lumry, J. Wolfe, J. Given, M. White, A. Woodring, L. Baitinger, K. House, B. Prillaman and T. Shah, Am. J. Respir. Crit. Care Med., 161, 527 (2000); https://doi.org/10.1164/ajrccm.161.2.9905091
  14. J.J. Condemi, S. Goldstein, C. Kalberg, S. Yancey, A. Emmett and K. Rickard, Ann. Allergy Asthma Immunol., 82, 383 (1999); https://doi.org/10.1016/S1081-1206(10)63288-7
  15. W. Busse, S.M. Koenig, J. Oppenheimer, S.A. Sahn, S.W. Yancey, D. Reilly, L.D. Edwards and P.M. Dorinsky, J. Allergy Clin. Immunol., 111, 57 (2003); https://doi.org/10.1067/mai.2003.38
  16. N. Ringdal, A. Eliraz, R. Pruzinec, H.-H. Weber, P.G.H. Mulder, M. Akveld and E.D. Bateman, Respir. Med., 97, 234 (2003); https://doi.org/10.1053/rmed.2003.1436
  17. B. Davies, G. Brooks and M. Devoy, Respir. Med., 92, 256 (1998); https://doi.org/10.1016/S0954-6111(98)90105-6
  18. ICH Harmonized Tripartite Guideline, Impurities in New Drug Substances Q3A (R2), edn. 4 (2006).
  19. ICH Harmonized Tripartite Guideline, Impurities in New Drug Products Q3B (R2), edn. 4 (2006).
  20. USP Pharmacopeias Forum. Volume No. 35(2), Page 307. 21. S. Lemaire, I.N. Houpis, T. Xiao, J. Li, E. Digard, C. Gozlan, R. Liu, A. Gavryushin, C. Diène, Y. Wang, V. Farina and P. Knochel, Org. Lett., 14, 1480 (2012); https://doi.org/10.1021/ol300220p
  21. ICH Harmonized Triplicate Guideline: Impurities in New Drug Substances Q3A (R2), ICH Steering Committee, Step 4 of ICH process (2006).
  22. I.F. Skidmore, L.H.C. Lunts, H. Finch and A. Naylor, GB Patent 2140800 (1993).
  23. B.V. Bhaskar, E.R.C. Sekhar, B.S. Reddy, V.S.N.V. Lakshmi Varaprasad, P. Rajagopal, S.S. Reddy, C.P. Arulnathan, D. Surya and S. Reddy, Preparation of Salmeterol and salts there of, Swiss Patent, 2560/CHE/2008A (2008).
  24. S.D. Dwivedi, N. Shah and Shyamlal, Process for the Preparation of Salmeterol and its Intermediates, WO2012/032546 A2 (2012).
  25. R. Hett, R. Stare and P. Helquist, Tetrahedron Lett., 35, 9375 (1994); https://doi.org/10.1016/S0040-4039(00)78546-7
  26. Y. Rong and A.E. Ruoho, Synth. Commun., 29(12a), 2155 (1999); https://doi.org/10.1080/00397919908086211
  27. J. Liu, D. Zhou, X. Jia, L. Huang, X. Li and A.S.C. Chan, Tetrahedron Asymm., 19, 1824 (2008); https://doi.org/10.1016/j.tetasy.2008.07.021
  28. S. Hbaïeb, Z. Latin and H. Amri, Synth. Commun., 29, 981 (1999); https://doi.org/10.1080/00397919908086061
  29. G.W. Gribble, Chem. Soc. Rev., 27, 395 (1998); https://doi.org/10.1039/a827395z
  30. P.A. Procopiou, G.E. Morton, M. Todd and G. Webb, Tetrahedron Asymm., 12, 2005 (2001); https://doi.org/10.1016/S0957-4166(01)00350-0
  31. C.E. Clark, A.D. Ferguson and J.A. Siddorn, Respir. Med., 87, 227 (1993); https://doi.org/10.1016/0954-6111(93)90098-K
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