An improved and scalable process for the synthesis of ezetimibe: An antihypercholesterolemia drug

Organic Process Research and Development

Volumn 13, Issue 5, 2009, Pages 907-910

  Sasikala, C H V A ^a   Padi, Pratap Reddy ^a   Sunkara, Vishnuvardhan ^a   Ramayya, Pattabhi ^a   Dubey, P K ^b   Uppala, Venkata Bhaskar Rao ^a   Praveen, Cherukupally ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

^b JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 70449411413     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900039z     Document Type: Article

References (41)

1. For recent reviews on the biological activity of β-lactam, see: (a) Singh, G. S. Mini-Rev. Med. Chem. 2004, 4, 69.
2. (b) Singh, G. S. Mini-Rev. Med. Chem. 2004, 4, 93.
3. (c) Veinberg, G.; Vorona, M.; Shestakova, I.; Kanepe, I.; Lukevics, E. Curr. Med. Chem. 2003, 10, 1741.
4. (d) Kidwai, M.; Sapra, P.; Bhushan, K. R. Curr. Med. Chem. 1999, 6, 195.
5. Bays, H. Expert Opin. Investig. Drugs 2002, 11, 1587-1604.
6. (a) Turley, S. D.; Dietschy, J. M. Curr. Opin. Lipidol. 2003, 14, 233-240.
7. Van Heek, M.; Davis, H. Eur. Heart. J. 2002, 4, J5 (Suppl.).
8. (a) Knopp, R. H.; Gitter, H.; Truitt, T.; Bays, H.; Manion, C. V.; Lipka, L. J.; LeBeaut, A. P.; Suresh, R.; Yang, B.; Veltri, E. P. Eur. Heart J. 2003, 24, 729-741.
9. (b) Bays, H. E.; Moore, P. B.; Drehobl, M. A.; Rosenblatt, S.; Toth, P. D.; Dujovne, C. A.; Knopp, R. H.; Lipka, L. J.; LeBeaut, A. P.; Yang, B.; Mellars, L. E.; Cuffie-Jackson, C.; Veltri, E. P. Clin. Ther. 2001, 23, 1209-1230.
10. (c) Gagne, C.; Bays, H. E.; Weiss, S. R.; Mata, P.; Quinto, K.; Melino, M.; Cho, M.; Musliner, T. A.; Gumbiner, B. Am. J. Cardiol. 2002, 90, 1084-1091.
11. Altmann, S. W.; Davis, H. R.; Zhu, L. J.; Yao, X. R.; Hoos, L. M.; Tetzloff, G.; Iyer, S. P. N.; Maguire, M.; Golovko, A.; Zeng, M.; Wang, L. Q.; Murgolo, N.; Graziano, M. P. Science 2004, 303, 1201-1204.
12. Clader, J. W. J. Med. Chem. 2004, 47, 1-9.
13. Rosenblum, S. B.; Huynh, T.; Afonso, A.; Davis, H. R.; Yumibe, N.; Clader, J. W.; Burnett, D. J. Med. Chem. 1998, 41, 973-980.
14. Van Heek, M.; Farley, C.; Compton, D. S.; Hoos, L.; Alton, K. B.; Sybertz, E. J.; Davis, H. R. Br. J. Pharmacol. 2000, 129, 1748-1754.
15. (a) N. Pandya, N.; Santani, D.; Jain, S. Indian J. Pharmacol. 2006, 38, 205-206
16. (b) Nutescu, E. A.; Shapiro, N. L. Pharmacotherapy 2003, 23, 1463-1474.
17. Earl, J.; Kirkpatrick, P. Ezetimibe. Nat. Rev. Drug Discovery 2003, 2, 97-98.
18. Bruckert, E. Cardiology 2002, 97, 59-66, and references cited therein.
19. Euroaspire. Eur. Heart J. 2001, 22, 554-572.
20. Earl, J.; Kirkpatrick, P. Nat. Rev. Drug Discovery 2003, 2 (2), 97-98.
21. (a) Homann, M. J.; Previte, E. U.S. Patent 6,133,001, 2000.
22. (b) Thiruvengadam, T. K.; Fu, X.; Tann, C.-H.; Mcallister, T. L.; Chiu, J. S.; Colon, C. Patent WO0034240, 2000.
23. (c) Wu, G.; Wong, Y.; Chen, X.; Ding, Z. J. Org. Chem. 1999, 64, 3714-3718.
24. (d) Wu, G.-Z.; Chen, X.; Wong, Y.-S.; Schumacher, D. P.; Steinman, M. U.S. Patent 5,886,171, 1999.
25. (e) Shankar, B. B. U.S. Patent 5,856,473,1999.
26. (f) Wu, G.-Z.; Chen, X.; Wong, Y.-S.; Schumacher, D. P.; Steinman, M. Patent WO9745406, 1997.
27. (g) Shankar, B. B.; Kirkup, M. P.; McCombie, S. W.; Clader, J. W.; Ganguly, A. K. Tetrahedron Lett. 1996, 37, 4095-11098
28. (h) Burnett, D. A. Tetrahedon Lett. 1994, 35, 7339-7342.
29. (a) Castaner, R. M.; Sorbera, L. A.; Castañer, J. Drugs Future 2000, 25, 679-685.
30. (b) Rosenblum, S. B.; Huynh, T.; Afonso, A. J. Med. Chem. 1998, 47, 973-980.
31. Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 727, 5653-5660.
32. Mahrwald, R. J. Prakt. Chem. 1999, 347, 595-599.
33. Hendrickson, J. B.; Wang, J. Org. Lett. 2004, 6, 3-5.
34. (a) Negishi, E. J. Org. Chem. 1977, 42, 1821.
35. (b) Negishi, E.; Anastasia, L. Chem. Rev. 2003, 703, 1979.
36. (c) Zhou, J.; Fu, G. J. Am. Chem. Soc. 2003, 725, 12527.
37. (d) Negishi, E.; Anastasia, L. J Organomet. Chem. 2002, 653, 34.
38. (e) Hassner, A.; Stumer, C. Organic Syntheses Based on Name Reactions; Pergamon Press: Amsterdam, Boston, 2002; Vol.2, p 260.
39. (f) Manley, P.; Acemoglu, M.; Martere, W.; Pachinger, W. Org. Process Res. Dev. 2003, 7, 436.
40. (a) Quallich, G. J.; Woodall, T. M. Tetrahedron Lett. 1993, 34, 785-788.
41. (b) Kawanami, Y.; Murao, S.; Ohga, T.; Kobayashi, N. Tetrahedron. 2003, 59, 8411-8414.