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Synthesis of the Polymorphic Forms of Clopidogrel Hydrogen Sulfate Through Reactive Crystallization and Transformation
Corresponding Author(s) : J. Lu
Asian Journal of Chemistry,
Vol. 25 No. 4 (2013): Vol 25 Issue 4
Abstract
This work reports the preparation, solid state characterization and solvent-mediated transformation of the amorphous, I and II forms of clopidogrel hydrogen sulfate. In particular, labile precipitate and oiling out occurring in the reactive crystallization of clopidogrel hydrogen sulfate are firstly reported and analyzed. The occurrence domains of three forms are also schematically outlined as well. These results will contribute to a better understanding about the polymorphic nature of clopidogrel hydrogen sulfate, together with the approaches to synthesizing its pure forms.
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- S.L. Morissette, Ö. Almarsson, M.L. Peterson, J.F. Remenar, M.J. Read, A.V. Lemmo, S. Ellis, M.J. Cima and C.R. Gardner, Adv. Drug Deliv. Rev., 56, 275 (2004).
- S.R. Byrn, R.R. Pfeiffer and J.G. Stowell, Solid State Chemistry of Drugs, SSCI Inc., West Lafayette, p. 16 (1999).
- J.K. Haleblian and W.J. McCrone, J. Pharm. Sci., 58, 911 (1969).
- J. Lu and S. Rohani, Org. Proc. Res. Dev., 13, 1262 (2009).
- A.H. Mangood, M.M. Seif and S.M. Hamza, Asian J. Chem., 22, 7257 (2010).
- W. Yue and G. Nie, Asian J. Chem., 21, 6295 (2009).
- M.V. Krishna, J.R. Babu, P.V.M. Latha and D.G. Sankar, Asian J. Chem., 19, 1369 (2007).
- J. Ahmad, Asian J. Chem., 14, 223 (2002).
- J.S. Dickie and L.J. Scott, Am. J. Cardiovasc. Drug, 6, 407 (2006).
- H.J. Kim and K.J. Kim, Ind. Eng. Chem. Res., 48, 11133 (2009).
- J. Lu and S. Rohani, Curr. Med. Chem., 16, 884 (2009).
- J. Bernstein, R.J. Davey and J.O. Henck, Angew. Chem. Int. Ed., 38, 3440 (1999).
- L. Codan, M.U. Bäbler and M. Mazzotti, Cryst. Growth Des., 10, 4005 (2010).
- P.J. Skrdla, V. Antonucci, L.S. Crocker, R.M. Wenslow, L. Wright and G. Zhou, J. Pharm. Biomed. Anal., 25, 731 (2001).
- L.E. O'Brien, P. Timmins,A.C. Williams and P. York, J. Pharm. Biomed. Anal., 36, 335 (2004).
References
S.L. Morissette, Ö. Almarsson, M.L. Peterson, J.F. Remenar, M.J. Read, A.V. Lemmo, S. Ellis, M.J. Cima and C.R. Gardner, Adv. Drug Deliv. Rev., 56, 275 (2004).
S.R. Byrn, R.R. Pfeiffer and J.G. Stowell, Solid State Chemistry of Drugs, SSCI Inc., West Lafayette, p. 16 (1999).
J.K. Haleblian and W.J. McCrone, J. Pharm. Sci., 58, 911 (1969).
J. Lu and S. Rohani, Org. Proc. Res. Dev., 13, 1262 (2009).
A.H. Mangood, M.M. Seif and S.M. Hamza, Asian J. Chem., 22, 7257 (2010).
W. Yue and G. Nie, Asian J. Chem., 21, 6295 (2009).
M.V. Krishna, J.R. Babu, P.V.M. Latha and D.G. Sankar, Asian J. Chem., 19, 1369 (2007).
J. Ahmad, Asian J. Chem., 14, 223 (2002).
J.S. Dickie and L.J. Scott, Am. J. Cardiovasc. Drug, 6, 407 (2006).
H.J. Kim and K.J. Kim, Ind. Eng. Chem. Res., 48, 11133 (2009).
J. Lu and S. Rohani, Curr. Med. Chem., 16, 884 (2009).
J. Bernstein, R.J. Davey and J.O. Henck, Angew. Chem. Int. Ed., 38, 3440 (1999).
L. Codan, M.U. Bäbler and M. Mazzotti, Cryst. Growth Des., 10, 4005 (2010).
P.J. Skrdla, V. Antonucci, L.S. Crocker, R.M. Wenslow, L. Wright and G. Zhou, J. Pharm. Biomed. Anal., 25, 731 (2001).
L.E. O'Brien, P. Timmins,A.C. Williams and P. York, J. Pharm. Biomed. Anal., 36, 335 (2004).