Separation of racemic bicalutamide by an optimized combination of continuous chromatography and selective crystallization

Organic Process Research and Development

Volumn 16, Issue 2, 2012, Pages 331-342

  Kaemmerer, Henning ^a,b   Horvath, Zoltan ^b   Lee, Ju Weon ^b   Kaspereit, Malte ^b,d   Arnell, Robert ^c   Hedberg, Martin ^c   Herschend, Björn ^c   Jones, Matthew J ^c   Larson, Kerstin ^c   Lorenz, Heike ^b   Seidel Morgensten, Andreas ^b  

^a EVONIK INDUSTRIES AG   (Germany)

^b MAX PLANCK INSTITUTE FOR DYNAMICS OF COMPLEX TECHNICAL SYSTEMS   (Germany)

^c ASTRAZENECA R AND D   (Sweden)

^d UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BICALUTAMIDE; COUPLING CONDITION; CRYSTALLIZATION PROCESS; DRUG SUBSTANCES; EUTECTIC COMPOSITION; PROCESS STEPS; PROSTATE CANCERS; RACEMIC MIXTURES; SELECTIVE CRYSTALLIZATION; SIMULATED MOVING BED CHROMATOGRAPHY; STATE OF THE ART;

OPTIMIZATION; SEPARATION;

CHROMATOGRAPHY;

EID: 84863122831     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op200136z     Document Type: Article

References (35)

1. Wirth, M. J. Urol. 2004, 172
2. Thijs, L. U.S. Pat. Appl. 2003/0073742, 2003.
3. Tucker, H.; Chesterson, G. J. J. Med. Chem. 1988, 31, 885
4. Zazhi, Z. Y. G. Chin. J. Pharm. 2006, 37, 73.
5. Sörös, B. WO 01/00608, 2006.
6. Ekwuribe, N. N. WO 01/28990, 1999.
7. James, K. D.; Ekwuribe, N. N. Tetrahedron 2002, 58, 5905
8. MDL ISIS, 2.5; Available Chemicals Directory (ACD) commercial catalogue database.
9. Fujino, A. Tetrahedron Lett. 2007, 48, 979
10. Sugai, T.; Ikunaka, M. JP 2008007492, 2008.
11. See: www.intenant.eu.
12. Guiochon, G.; Felinger, A.; Shirazi, D. G.; Katti, A. M. Fundamentals of Preparative and Nonlinear Chromatography, 2 nd ed.; Academic Press: Boston, 2006.
13. Chung, S. F.; Wen, C. Y. AICHhE J. 1968, 14, 857-866
14. Einstein, A. Ann. Phys. 1905, 17, 549-560
15. Antos, D. Doctoral Thesis, Oficyna Wydawnicza Politechniki Rzszowskiej, Rzeszöw, Poland, 2003.
16. Storti, G.; Mazzotti, M.; Morbidelli, M.; Carra, S. AIChE J. 1993, 39, 471-492
17. Lee, J. W.; Wankat, P. C. J. Chromatogr., A 2010, 1217, 3418-3426
18. Tan, K. K.; Wang, G.-G.; Hang, C. C.; Hagglund, T. Advances in PID Control. Springer Verlag: London, 1999.
19. Kaspereit, M., Doctoral Thesis, Otto-von-Guericke-University, Magdeburg, Germany, 2006.
20. Kaspereit, M.; Gedicke, K.; Zahn, V.; Mahoney, A. W.; Seidel-Morgenstern, A. J. Chromatogr., A 2005, 1092, 43-54
21. Gedicke, K.; Kaspereit, M.; Beckmann, W.; Budde, U.; Lorenz, H.; Seidel-Morgenstern, A. Chem. Eng. Res. Des. 2007, 85, 928-936
22. Amanullah, M.; Abel, S.; Mazzotti, M. Adsorption 2005, 11, 893-897
23. Amanullah, M.; Mazzotti, M. J. Chromatogr. A 2006, 1107, 36-45
24. Kaemmerer, H.; Jones, M. J.; Lorenz, H.; Seidel-Morgenstern, A. Fluid Phase Equilib. 2010, 296, 192-205
25. Lorenz, H.; Kaemmerer, H.; Polenske, D.; Seidel-Morgenstern, A. EP08163733.2, 2008.
26. Lorenz, H.; Kaemmerer, H.; Polenske, D.; Seidel-Morgenstern, A. WO 2010/025968 A2, 2008.
27. Wang, Y.; LoBrutto, R.; Wenslow, R. W.; Santos, I. Org. Process Res. Dev. 2005, 9, 670-676
28. Klussmann, M.; White, A. J. R.; Armstrong, A.; Blackmond, D. G. Angew. Chem., Int. Ed. 2006, 45, 7985-7989
29. Mullin, J. W. Crystallization; Butterworth-Heinemann: Oxford, 1997.
30. Tulashie, S. K.; Kaemmerer, H.; Lorenz, H.; Seidel-Morgenstern, A. J. Chem. Eng. Data 2010, 55, 333-340
31. Prigogine, I.; Defay, R. Chemical Thermodynamics; Longmann: London, UK, 1973.
32. Polenske, D.; Lorenz, H. J. Chem. Eng. Data 2009, 54, 2277-2280
33. Kaemmerer, H.; Lorenz, H.; Seidel-Morgenstern, A. Chem. Ing. Tech. 2009, 81, 1955-1965
34. Zhang, Y.; Ray, A.; Rohani, S. Chem. Eng. Sci. 2009, 64, 192-197
35. Worlitschek, J.; Bosco, M.; Huber, M.; Gramlich, V.; Mazzotti, M. Helv. Chim. Acta 2004, 87, 279-291