Concomitant polymorphs of the antihyperlipoproteinemic bezafibrate

Crystal Growth and Design

Volumn 9, Issue 6, 2009, Pages 2646-2655

  Lemmerer, Andreas ^a   Báthori, Nikoletta B ^a   Esterhuysen, Catharine ^b   Bourne, Susan A ^a   Caira, Mino R ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

^b STELLENBOSCH UNIVERSITY   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 66849087208     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg8011298     Document Type: Article

References (62)

1. (a) Bernstein, J. Polymorphism in Molecular Crystals; IUCr Monographs on Crystallography; Oxford Science Publications: Oxford, U.K., 2002; Vol. 14.
2. (b) Vishweshar, P.; McMahon, J. A.; Bis, J. A.; Zaworotko, M. J. J. Pharm. Sci. 2006, 95, 499-516.
3. (c) Shan, N.; Zaworotko, M. J. Drue Discovery Today 2008, 13, 440-446.
4. (d) Benghiat, V.; Leiserowitz, L. J. Chem. Soc. 1972, 1763-1768.
5. (e) Ahn, S.; Kariuki, B. M.; Harris, K. D. M. Cryst. Growth Des. 2001, 1, 107-111.
6. (f) Pal, T.; Kar, T.; Bocelli, G.; Rigi, L. Cryst. Growth Des. 2003, 3, 13-16.
7. (g) Timofeeva, T. V.; Kuhn, G. H.; Nesterov, V. V.; Nsterov, V. N.; Frazier, D. O.; Penn, B. G.; Antipin, M. Y. Cryst Growth Des. 2003, 3, 383-391.
8. (h) Munshi, P.; Venugopala, K. N.; Jayashree, B. S.; Row, T. N. G. Cryst. Growth Des. 2004, 4, 1104-1107.
9. (i) Timofeeva, T. V.; Kinnibrugh, T.; Borbulevych, O. Y.; Averkiev, B. B.; Nesterov, V. N.; Sloan, A.; Antipin, M. Y. Cryst. Growth Des. 2004, 4, 1265-1276.
10. (j) Rafilovich, M.; Bernstein, J.; Harris, R. K.; Apperley, D. C.; Karamertzanis, P. G.; Price, S. L. Cryst. Growth Des. 2005, 5, 2197-2209.
11. (k) Blagden, N.; Davey, R.; Dent, G.; Song, M.; David, W. I. F.; Pulham, C. R.; Shankland, K. Cryst. Growth Des. 2005, 5, 2218-2224.
12. Munshi, P.; Row, T. N. G. Cryst. Growth Des. 2006, 6, 708-718.
13. (m) Wishkerman, S.; Bernstein, J.; Stephens, P. W. Cryst. Growth Des. 2006, 6, 1366-1373.
14. (n) Porter, W. W., III.; Elie, S. C.; Matzger, A. J. Cryst. Growth Des. 2008, 8, 14-16.
15. (o) Griesser, U. J.; Jetti, R. K. R.; Haddow, M. F.; Brehmer, T.; Apperley, D. C.; King, A.; Harris, R. K. Cryst. Growth Des. 2008, 8, 44-56.
16. (p) Barsky, I.; Bernstein, J.; Stephens, P. W.; Stone, K. H.; Cheung, E.; Hickey, M. B.; Henck, J.-O. Cryst. Growth Des. 2008, 8, 63-70.
17. (a) Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem. Int. Ed. 1999, 38, 3440-3461.
18. (b) Munshi, P.; Venugopala, K. N.; Jayashree, B. S.; Row, T. N. G. Cryst. Growth Des. 2004, 4, 1105-1107.
19. (c) Munshi, P.; Row, T. N. G. Cryst. Growth Des. 2006, 6, 708-718.
20. (d) Rafilovich, M.; Bernstein, J.; Harris, R. K.; Apperley, D. C.; Karamertzanis, P. G.; Price, S. L. Cryst. Growth Des. 2005, 5, 2197-2209.
21. (e) ter Horst, J. H.; Kramer, H. J. M.; Jansens, P. J. Cryst. Growth Des. 2002, 2, 351-356.
22. Witte, E. C.; Stach, K.; Thiel, M.; Schmidt, F.; Stork, H. 1973.
23. Bourgogne, J.-P.; Sornay, R. 1988.
24. Beyer, P. 1979.
25. Djinović, K.; Globokar, M.; Zupet, P. Acta Crystallogr. 1989, C45, 772-775.
26. Morsdorf, P.; Maier, P.; Schmitt, J.; Ahrens, K.-H. 1994.
27. No labelling of the previously known needle-like form is given. This is often the case for the first reported structure of a system not known to be polymorphic. This is thus assumed to be the a form of bezafibrate.
28. The measured PXRD trace of form β is compared to the calculated (from the single crystal structure reported by Djinović et al.) trace of form a. However, no measured IR spectrum of form α was reported or referred to in the patent.
29. Form β of bezafibrate was obtained serendipitously as part of our program to obtain co-crystals of a number of APIs (containing carboxylic acid functional groups) with nicotinamide and iso-nicoti-namide. Form β of bezafibrate was crystallized from an unsuccessful attempt to co-crystallize bezafibrate with iso-nicotinamide from a solution of 2-butanone.
30. COLLECT; Nonius BV: Delft, The Netherlands, 1998.
31. Otwinowski, Z.; Minor, W. In International Tables for Crystallography; Rossman, M. G., Arnold, E.; Kluwer: Dordrecht, 2000; Vol. F.
32. XPREP2, Version 6.14; Bruker AXS Inc.: Madison, Wisconsin, USA, 2003.
33. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565; WinGX.
34. Sheldrick, G. M. SHELXS-97, Program for the Solution of Crystal Structure; University of Gottingen: Germany, 1997.
35. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structure; University of Gottingen: Germany, 1997.
36. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13.
37. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838; WinGX.
38. Brandenburg, K. Diamond, Version 2.1e.; Crystal Impact GbR: Bonn, Germany.
39. Frisch, M. J. Gaussian 03, Revision B.05; Gaussian, Inc.: Pittsburgh PA, 2003.
40. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
41. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785-789.
42. (a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261.
43. (b) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta. 1973, 28, 213-222.
44. Hamprecht, F. A.; Cohen, A. J.; Tozer, D. J.; Handy, N. C. J. Chem. Phys. 1998, 109, 6264-6271.
45. (a) Simon, S.; M. Duran, M.; Dannenberg, J. J. J. Chem. Phys. 1996, 105, 11024-11031.
46. (b) Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566.
47. The peaks in the calculated trace are shifted to higher 2θ values due to the temperature difference of the calculated (-100 °C) and measured patterns for form α (163 °C) and form β (138°C).
48. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew. Chem. Intl. Ed. Engl. 1995, 34, 1555-1573.
49. (a) Leiserowitz, L. Acta Crystallogr. 1976, B32, 775-802.
50. (b) Dinabandhu, D.; Desiraju, G. R. Chem. Asian J. 2006, 1-2, 231-244.
51. (c) Dinabandhu, D.; Desiraju, G. R. Cryst Eng Comm 2006, 8, 674-679.
52. (a) McKinnon, J. J.; Spackman, M. A.; Mitchell, A. S. Chem.-Eur. J. 1998, 4, 2136-2141.
53. (b) McKinnon, J. J.; Mitchell, A. S.; Spackman, M. A. Chem. Commun. 1998, 2071-2072.
54. (c) Spackman, M. A.; McKinnon, J. J. Cryst Eng Comm 2002, 4, 378-392.
55. (d) McKinnon, J. J.; Spackman, M. A.; Mitchell, A. S. Acta Crystallogr. Sect. B 2004, 60, 627-668.
56. (e) McKinnon, J. J.; Fabbiani, F. P. A.; Spackman, M. A. Cryst. Growth Des. 2007, 7, 755-769.
57. Wolff, S. K.; Grimwood, D. J.; McKinnon, J. J.; Jayatilaka, D.; Grimwood, D. J. Crystal Explorer, Version 2.1 (381); University of Western Australia, Australia.
58. (a) Leiserowitz, L. Acta Crystallogr. Sect. B 1976, 32, 775-802.
59. (b) Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1989, 111, 405-4507.
60. (c) Montzka, T. A.; Swaminathan, S.; Firestone, R. A. J. Phys. Chem. 1994, 98, 13171-13176.
61. Cambridge Structural Database, Feb. 2009 update. Search criteria: Fragments containing a COOH group where the O=C-O-H torsion angle had a value between-40 and 40 deg, corresponding to a syn conformation. Allen, F. H. Acta Crystallogr. Sect. B 2002, 58, 380-388.
62. Sato, H.; Hirata, F. J. Mol. Struct: Theochem 1999, 461-462, 113-120.