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Impurities in Finasteride: Identification, Synthesis, Characterization and Control of Potential Carry-Over Impurities from Reagents Used for the Process
Corresponding Author(s) : Sandeep Mohanty
Asian Journal of Chemistry,
Vol. 26 No. 14 (2014): Vol 26 Issue 14
Abstract
An assessment of the impurity profile of finasteride and possible carry-over related substances likely to arise during the synthesis of finasteride is described in this article. Impurities in reaction mass were monitored by HPLC, potential impurities isolated with preparative HPLC and structures were substantiated by 1H NMR, MS and MS-MS. Impurities RRT's were established by HPLC co-injection. Based on the spectral data structure of impurity I and impurity II were characterized as cyclohexyl and phenyl analog of finasteride.
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- G.H. Rasmusson and G.F. Reynolds, Enzyme Inhibitor, US Patent 4760071 (1988).
- G.N. Collin, BMJ, 315, 317 (1997).
- J. Leyden, F. Dunlap, B. Miller, P. Winters, M. Lebwohl, D. Hecker, S. Kraus, H. Baldwin, A. Shalita, Z. Draelos, M. Markou, D. Thiboutot, M. Rapaport, S. Kang, T. Kelly, D. Pariser, G. Webster, M. Hordinsky, R. Rietschel, H.I. Katz, L. Terranella, S. Best, E. Round and J. Waldstreicher, J. Am. Acad. Dermatol., 40, 930 (1999); doi:10.1016/S0190-9622(99)70081-2.
- ICH Guideline, Impurities in New Drug Substances Q3A (R2), October 25, 2006.
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- European Pharmacopoeia 7, 01-2011, 2018.
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References
G.H. Rasmusson and G.F. Reynolds, Enzyme Inhibitor, US Patent 4760071 (1988).
G.N. Collin, BMJ, 315, 317 (1997).
J. Leyden, F. Dunlap, B. Miller, P. Winters, M. Lebwohl, D. Hecker, S. Kraus, H. Baldwin, A. Shalita, Z. Draelos, M. Markou, D. Thiboutot, M. Rapaport, S. Kang, T. Kelly, D. Pariser, G. Webster, M. Hordinsky, R. Rietschel, H.I. Katz, L. Terranella, S. Best, E. Round and J. Waldstreicher, J. Am. Acad. Dermatol., 40, 930 (1999); doi:10.1016/S0190-9622(99)70081-2.
ICH Guideline, Impurities in New Drug Substances Q3A (R2), October 25, 2006.
A. Bhattacharya, L.M. DiMichele, U.H. Dolling, A.W. Douglas and E.J.J. Grabowski, J. Am. Chem. Soc., 110, 3318 (1988); doi:10.1021/ja00218a062.
European Pharmacopoeia 7, 01-2011, 2018.
A. Bhattacharya, J.M. Williams, J.S. Amato, U.-H. Dolling and E.J.J. Grabowski, Syn. Commun., 20, 2683 (1990); doi:10.1080/00397919008051477.
(a) R.K. Bakshi, G.H. Rasmusson, G.F. Patel, R.T. Mosley, B. Chang, K. Ellsworth, G.S. Harris and R.L. Tolman, J. Med. Chem., 39, 1192 (1996); doi:10.1021/jm950927n.; (b) R.K. Bakshi, G.H. Rasmusson, G.F. Patel, R.T. Mosley, B. Chang, K. Ellsworth, G.S. Harris and R.L. Tolman, J. Med. Chem., 38, 3189 (1995); doi:10.1021/jm00017a001.
(a) D. Lilstein, PCT 2012052996; (b) J. Pasek and M. Petrisko, A Method for the Catalytic Reduction of Nitrobenzene to Aniline in the Liquid Phase, EP2471768 (2012); (c) M. Chatterjee, M. Sato, H. Kawanami, T. Ishizaka, T. Yokoyama and T. Suzuki, Appl. Catal., 396, 186 (2011); doi:10.1016/j.apcata.2011.02.016.
F. Saliu, B. Putomatti and B. Rindone, Tetrahedron Lett., 53, 3590 (2012); doi:10.1016/j.tetlet.2012.05.015.
P. Hussenet, P. Le Goff and G. Sennyey, Process for the Synthesis of Substituted Carbodiimides, US Patent 5648537 (1997)..