Synthesis and comprehensive structural and physicochemical characterization of dutasteride hydrochloride hydrate solvates

FDA prescribing information. June 2011. Retrieved 15 September 2013. Tarter, 2006, Inhibitors of 5α-reductase in the treatment of benign prostatic hyperplasia, Curr. Pharm. Des., 12, 775, 10.2174/138161206776056010 Nanubolu, 2012, Dutasteride hydrochloride solvates. Resonance-assisted amide protonation in dutasteride hydrochloride salt, Cryst. Eng. Comm., 14, 2571, 10.1039/c2ce06421a Griesser, 2011, The importance of solvates, 211 C. Vladiskovic, E. Attolino, P. Allegrini, G. Razetti, Linezolid crystalline hydrate form and linezolid salts. EP, 2033960 A2 [P]. 2009-03-11. Sidorov, 2002, Ion channel formation from a calix[4]arene amide that binds HCl, J. Am. Chem. Soc., 124, 2267, 10.1021/ja012338e Łaszcz, 2015, Phase transition studies of dutasteride crystalline forms, Cryst. Eng. Comm., 17, 2346, 10.1039/C5CE00036J M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford, CT, 2013. Agilent. CrysAlis PRO. Agilent Technologies, Yarnton, England, 2011. Sheldrick, 2008, A short history of SHELX, Acta Cryst., A64, 112, 10.1107/S0108767307043930 K.W. Bachelor, S.V. Frye, Androstenone derivative. WO, 95/07927 [P]. 1995-03-23. Dams, 2015, Opracowanie technologii wytwarzania dutasterydu o czystości farmaceutycznej (Development of the process for preparation of dutasteride of pharmaceutical-grade purity), Przem. Chem., 94, 1000 I. Dams, M. Chodyński, A. Ostaszewska, W. Szczepek, M. Krupa, E. Lipiec-Abramska, M. Kubiszewski, Sposób otrzymywania dutasterydu o czystości farmaceutycznej. Polish Patent Appl., P-413649 [P]. 2015-08-24. A. Vecchioli, D.G. Tombari, C.P. Mangone, M.B. Garcia, R.A. Labriola, Solid and crystalline dutasteride and processes for preparation thereof. WO, 2009/083258 A2 [P]. 2009-07-09. S. Katkam, S. Komati, S. Gudipati, J. Pitta, N.R. Challa, R. Bucchikondla, S.R. Mallina, A.C. Goldwyn, M.R. Kharkar, S.P. Narsapur, S.R. Maddula, R. Kasula, A.M. Lali, S.B. Kale, A.J. Bhori, Preparation of dutasteride. WO, 2007/120263 A2 [P]. 2007-10-25. M.S. Reddy, C. Nagaraju, G. Srinivasulu, M.V.N.B. Rao, B.R. Reddy, Forms of dutasteride and methods for preparation thereof. US Patent Appl., 2004/0077673 A1 [P]. 2004-04-22. Single X-ray crystal data of the mono(dutasteride) monohydrochloride monohydrate mono(acetone), -mono(ethanol) and -mono(methanol) solvates CCDC numbers 1061654, 1061655, and 1063084, respectively, have been deposited at The Cambridge Crystallographic Data Centre. The deposition numbers contain supplementary crystallographic data. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.htmL (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44-1223-336033; e-mail: [email protected]). Jiang, 2005, New approach to 3-oxo-4-aza-5α-androst-1-ene-17β-(N-tert-butylcarboxamide), Steroids, 70, 690, 10.1016/j.steroids.2005.03.009 Y.H. Moon, D.J. Kim, Ch.-H. Park,K.I. Lee, J.-Ch. Lee,G.S. Lee, Y.-K. Chang, Method for the preparation of highly pure 1-androstene derivatives. US, 7038050 B1 [P]. 2006-05-02. B. Sörös, Z. Tuba, V. Gálik, S. Mahó, L. Balogh, P. Vincze, J. Horváth, A. Kovács, Z. Béni, F. Varga, Process for the synthesis of (5β,17)-N-[(2,5-bis(trifluoromethyl)-phenyl]-3-oxo-4-aza-5-androst-1-ene-17-carboxamide. WO, 2013/001322 A1 [P]. 2013-01-03. Frelek, 2015, Comprehensive spectroscopic characterization of finasteride polymorphic forms. Does the form X exist?, J. Pharm. Sci., 104, 1650, 10.1002/jps.24369 Satyanarayana, 2008, Commercial scaleable process for the preparation of polymorphic form-II of dutasteride, Rasayan J. Chem., 1, 322 Gottlieb, 1997, NMR chemical shifts of common laboratory solvents as trace impurities, J. Org. Chem., 62, 7512, 10.1021/jo971176v