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Copyright (c) 2014 Changyan Hu, Dongling Wang, Kunquan Chen, Xu Liu, Qichao Chen, Dequn Sun*
This work is licensed under a Creative Commons Attribution 4.0 International License.
Development and Validation of Process for Resolution of Praziquantel Amine for Preparation of Chiral Praziquantel
Corresponding Author(s) : Changyan Hu
Asian Journal of Chemistry,
Vol. 26 No. 23 (2014)
Abstract
Investigation of the viability of scale up preparation for chiral praziquantel was included in WHO/TDR business plan. Resolution is the major strategy for preparation of single enantiomer. In this study, a stable and effective resolution approach toward the important intermediate praziquantel amine for preparation of chiral praziquantel was developed and the process was optimized to afford high ee value and good yield. The suitable HPLC method was validated for the determination of ee value of chiral praziquantel amine.
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- L. Chitsulo, D. Engels, A. Montresor and L. Savioli, Acta Trop., 77, 41 (2000).
- M.J. Doenhoff, D. Cioli and J. Utzinger, Curr. Opin. Infect. Dis., 21, 659 (2008).
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- P. Roszkowski, J.K. Maurin and Z. Czarnocki, Tetrahedron Asymm., 17, 1415 (2006).
- T. Meyer, H. Sekljic, S. Fuchs, H. Bothe, D. Schollmeyer and C. Miculka, PLoS Negl. Trop., 3, e357 (2009).
- M.J. Doenhoff and L. Pica-Mattoccia, Anti Infect.Ther., 4, 199 (2006).
- C.R. Caffrey, Curr. Opin. Chem. Biol., 11, 433 (2007).
- A. Fenwick and J.P. Webster, Curr. Opin. Infect. Dis., 19, 577 (2006).
- Drug Development and Evaluation for Helminths and Other Neglected Tropical Diseases, Business Plan 2008-2013, WHO/TDR (2007).
- M. Woelfle, J.-P. Seerden, J. de Gooijer, K. Pouwer, P. Olliaro and M.H. Todd, PLoS Negl. Trop. Dis., 5, e1260 (2011).
- (a) J.H. Kim, Y.S. Lee, H. Park and C.S. Kim, Tetrahedron, 54, 7395 (1998); (b) C.H. Yang, L.Z. Zhang, Y. Zheng and D.Q. Sun, Asian J. Chem., 25, 9415 (2013).
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References
L. Chitsulo, D. Engels, A. Montresor and L. Savioli, Acta Trop., 77, 41 (2000).
M.J. Doenhoff, D. Cioli and J. Utzinger, Curr. Opin. Infect. Dis., 21, 659 (2008).
X. Shu-Hua and B.A. Catto, J. Infect. Dis., 159, 589 (1989).
M.H. Wu, C.C. Wei, Z.Y. Xu, H.C. Yuan, W.N. Lian, Q.-J. Yang, M. Chen, Q.-W. Jiang, C.-Z. Wang, S.-J. Zhang, Z.-D. Liu, R.-M. Wei, S.-J. Yuan, L.-S. Hu and Z.-S. Wu, Am. J. Trop. Med. Hyg., 45, 345 (1991).
Y.H. Liu, M.X. Qian, X.G. Wang, J. Jia, Q.N. Wang, Y.F. Jiang, R.Q. Wang, S.H. Yan, B.Y. Chen and J.S. Li, Chin. Med. J. (Engl.), 99, 935 (1986).
P. Roszkowski, J.K. Maurin and Z. Czarnocki, Tetrahedron Asymm., 17, 1415 (2006).
T. Meyer, H. Sekljic, S. Fuchs, H. Bothe, D. Schollmeyer and C. Miculka, PLoS Negl. Trop., 3, e357 (2009).
M.J. Doenhoff and L. Pica-Mattoccia, Anti Infect.Ther., 4, 199 (2006).
C.R. Caffrey, Curr. Opin. Chem. Biol., 11, 433 (2007).
A. Fenwick and J.P. Webster, Curr. Opin. Infect. Dis., 19, 577 (2006).
Drug Development and Evaluation for Helminths and Other Neglected Tropical Diseases, Business Plan 2008-2013, WHO/TDR (2007).
M. Woelfle, J.-P. Seerden, J. de Gooijer, K. Pouwer, P. Olliaro and M.H. Todd, PLoS Negl. Trop. Dis., 5, e1260 (2011).
(a) J.H. Kim, Y.S. Lee, H. Park and C.S. Kim, Tetrahedron, 54, 7395 (1998); (b) C.H. Yang, L.Z. Zhang, Y. Zheng and D.Q. Sun, Asian J. Chem., 25, 9415 (2013).
P. Andrews, H. Thomas, R. Pohlke and J. Seubert, Praziquantel. Med. Res. Rev., 3, 147 (1983).