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Synthesis of Main Impurity of Vildagliptin
Corresponding Author(s) : Xiangnan Hu
Asian Journal of Chemistry,
Vol. 26 No. 12 (2014): Vol 26 Issue 12
Abstract
A four-step synthesis of the main impurity of vildagliptin has been easily accomplished with high-yielding starting from L-proline. This compound can be used as a reference marker in an analytical method to determine the chemical purity of the vildagliptin.
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- D.K. Arulmozhi and B. Portha, Eur. J. Pharm. Sci., 28, 96 (2006); doi:10.1016/j.ejps.2006.01.003.
- J.J. Holst, Exp. Opin. Investig. Drugs, 8, 1409 (1999); doi:10.1517/13543784.8.9.1409.
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- E.J. Verspohl, Pharmacol. Rev., 64, 188 (2012); doi:10.1124/pr.110.003319.
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- N.A. Thornberry and A.E. Weber, Curr. Topics Med. Chem., 7, 557 (2007); doi:10.2174/156802607780091028.
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References
D.K. Arulmozhi and B. Portha, Eur. J. Pharm. Sci., 28, 96 (2006); doi:10.1016/j.ejps.2006.01.003.
J.J. Holst, Exp. Opin. Investig. Drugs, 8, 1409 (1999); doi:10.1517/13543784.8.9.1409.
C.F. Deacon, M.A. Nauck, M. Toft-Nielsen, L. Pridal, B. Willms and J.J. Holst, Diabetes, 44, 1126 (1995); doi:10.2337/diab.44.9.1126.
B.D. Green, P.R. Flatt and C.J. Bailey, Diab. Vasc. Dis. Res., 3, 159 (2006); doi:10.3132/dvdr.2006.024.
E.J. Verspohl, Pharmacol. Rev., 64, 188 (2012); doi:10.1124/pr.110.003319.
S. Dhillon, Drugs, 70, 489 (2010).
N.A. Thornberry and A.E. Weber, Curr. Topics Med. Chem., 7, 557 (2007); doi:10.2174/156802607780091028.
B. Ahren, A. Schweizer, S. Dejager, E.B. Villhauer, B.E. Dunning and J.E. Foley, Diabetes Obes. Metab, 13, 775 (2011); doi:10.1111/j.1463-1326.2011.01414.x.
G. Stamataros and S.H. Schneider, Expert Opin. Pharmacother., 12, 1967 (2011); doi:10.1517/14656566.2011.593508.
M. Banerjee, N. Younis and H. Soran, Expert Opin. Pharmacother., 10, 2745 (2009); doi:10.1517/14656560903302265.
D.S. Kania, J.D. Gonzalvo and Z.A. Weber, Clin. Ther., 33, 1005 (2011); doi:10.1016/j.clinthera.2011.06.016.
J.J. Neumiller and R.K. Campbell, Am. J. Health Syst. Pharm., 67, 1515 (2010); doi:10.2146/ajhp090555.
R.E. Pratley, Expert Opin. Pharmacother., 10, 503 (2009); doi:10.1517/14656560802694713.
R.A. DeFronzo, C.F. Burant, P. Fleck, C. Wilson, Q. Mekki and R.E. Pratley, J. Clin. Endocrinol. Metab., 97, 1615 (2012); doi:10.1210/jc.2011-2243.
T. Rauch, U. Graefe-Mody, C.F. Deacon, A. Ring, J.J. Holst, H.-J. Woerle, K.A. Dugi and T. Heise, Diabetes Ther., 3, 10 (2012); doi:10.1007/s13300-012-0010-y.
A.H. Barnett, Adv. Ther., 28, 447 (2011); doi:10.1007/s12325-011-0028-y.
S. Winter, J. Bosch and J.P. Serrano, US Patent 972329 (2008).
A. Halama, K. Bozena and T. Chvojka, WO Patent 022690 (2010).
A.E. Fedorov, A.M. Shestopalov and P.A. Belyakov, Russ. Chem. Bull., 52, 2197 (2003); doi:10.1023/B:RUCB.0000011878.52263.c4.
H. Fukushima, A. Hiratate, M. Takahashi, M. Saito, E. Munetomo, K. Kitano, H. Saito, Y. Takaoka and K. Yamamoto, Bioorg. Med. Chem., 12, 6053 (2004); doi:10.1016/j.bmc.2004.09.010.
S.K. Singh, N. Manne and M. Pal, Beilstein J. Org. Chem., 4, No. 20 (2008); doi:10.3762/bjoc.4.20.
V. Aureggi and V. Franckevicius, Org. Synth., 85, 72 (2008); doi:10.15227/orgsyn.085.0072.
A. Bubendorf, O. Grassmann and D. Hunziker, US Patent 638752 (2006).