A facile total synthesis for large-scale production of imatinib base

Organic Process Research and Development

Volumn 16, Issue 11, 2012, Pages 1794-1804

  Kompella, Amala ^a   Adibhatla, Bhujanga Rao Kalisatya ^a   Muddasani, Pulla Reddy ^a   Rachakonda, Sreenivas ^a   Gampa, Venugopala Krishna ^a   Dubey, Pramod Kumar ^b  

^a NATCO   (India)

^b JNTUH COLLEGE OF ENGINEERING   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOYL CHLORIDES; IMATINIB; ISOPROPYL ALCOHOLS; LARGE-SCALE PRODUCTION; TOTAL SYNTHESIS;

CHLORINE COMPOUNDS;

POTASSIUM;

EID: 84869387120     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op300212u     Document Type: Article

References (27)

1. Li, X. Q.; Yang, J.; Chen, X. J.; Liu, J.; Li, H. R.; Li, J.; Zheng, J.; He, Y.; Chen, Z.; Huang, S. Cancer Genet. Cytogenet. 2007, 176, 166
2. El Hajj Dib, I.; Gallet, M.; Mentaverri, R.; Sévenet, N.; Brazier, M.; Kamel, S. Eur. J. Pharmacol. 2006, 551, 27
3. Van Oosterom, A. T.; Judson, J.; Verweij, E.; Stroobants, S.; Donato, D. P. E.; Dimitrijevic, S.; Martens, M.; Webb, A.; Sciot, R.; Van Glabbeke, M.; Silberman, S.; Nielsen, O. S. Lancet 2001, 358, 1421
4. Buchdunger, E.; Cioffi, C. L.; Law, N.; Stover, D.; Ohno-Jones, S.; Druker, B. J.; Lydon, N. B. J. Pharmacol. Exp. Ther. 2000, 295, 139
5. Krystal, G. W.; Honsawek, S.; Litz, J.; Litz Buchdunger. Clin. Cancer Res. 2000, 6, 3319
6. Weisberg, E.; Griffin, J. D. Blood 2000, 95, 34981
7. Druker, B. J.; Lydon, N. B. J. Clin. Invest. 2000, 105, 3
8. Zimmermann, J. CAS no. 120:107056, EP Patent 564,409, 1993.
9. Zimmermann, J. CAS no. 125:4681, U.S. Patent 5,521,184, 1996.
10. Zimmermann, J.; Buchdunger, E.; Mett, H.; Meyer, T.; Lydon, N. B.; Traxler, P. Bioorg. Med. Chem. Lett. 1996, 1221
11. Loiseleur, O.; Kaufmann, D.; Abel, S.; Buerger, H. M.; Meisenbach, M.; Schmitz, B.; Sedelmeier, G. CAS no. 139:180080, WO/2003/066,613, 2003.
12. Amala, K.; Bhujanga Rao, A. K. S.; Venkaiah Chowdary, N. CAS no. 142:56339, WO/2004/108699, 2004.
13. Zakacs, S.; Beni, Z.; Varga, S.; Orfi, Z.; Keri, L.; Noszal, G, B. J. Med. Chem. 2005, 249
14. Szczepek, W.; Luniewski, W.; Kaczmare, L.; Zagrodzki, B.; Samson-Lazinska, D.; Szelejewski, M.; Skarzynski, W. CAS no. 145:103728, U.S. Patent 7,674,901, 2010.
15. Ivanov, A. S.; Shishkov, S. V. Monatsh. Chem. 2009, 619
16. Liu, H.; Xia, W.; Luo, Y.; Lu, W. Monatsh. Chem. 2010, 907
17. Application no. NDA 21-335 Gleevec-pharm- P2. Center for Drug Evaluation and Research, U.S. Food and Drug Administration: Silver Spring, MD; http://www.accessdata.fda.gov/drugsatfda-docs/nda/2001/21-335-Gleevec-pharmr-P2. pdf.
18. ICH Topic S2B; Note for guidance. Genotoxicity: A Standard Battery for Genotoxicity Testing of Pharmaceuticals, CPMP/ICH/174/95, EMEA; Committee for Proprietary Medicinal Products (CPMP), European Medicines Agency (EMEA): London, 1998; http://www.ema.europa.eu/docs/en-GB/document-library/Scientific- guideline/2009/09/WC500003147.pdf.
19. Lambardino, J. G. CAS no. 106:50232, U.S. Patent 4,623,486, 1996.
20. Batchelor, M. J.; Moffat, D. F. C.; Davis, J. M.; Hutchings, M. C. CAS no. 106:50232, U.S. Patent 6,57,9983, 2003.
21. Takezaki, H.; Kitagawa, T.; Matsuoka, S. CAS no. 138321295, JP/2003/119184, 2003.
22. Takezaki, H.; Kitagawa, T.; Matsuoka, S. CAS no. 138:321296, JP/2003/119185, 2003.
23. Umetsu, K. CAS no. 137:370111, JP/2002/338558, 2002.
24. Sairam, P.; Puranik, R.; Keller, A. S.; Sasikiran, S.; Veerenderm, M.; Parvathi, A. Synth. Commun. 2003, 3597
25. Ziegler, K.; Spath, A.; Scoof, E.; Schumann, W.; Winkelmann, E. Justus Liebigs Ann. Chem. 1952, 80
26. Offermann, W.; Vogtle, F. Synthesis 1977, 272-273
27. Shaw, H.; Perlmutter, H. D.; Gu, C. J. Org. Chem. 1997, 236-237