Approaches to Polymorphism Screening

Polymorphism: in the Pharmaceutical Industry

Volumn , Issue , 2006, Pages 287-308

  Hilfiker, Rolf ^a   De Paul, Susan M ^a   Szelagiewicz, Martin ^a  

^a SOLVIAS AG   (Switzerland)

Author keywords

Characterization; Crystallization methods; Example; High throughput methods; Pharmaceutical industry; Polymorphism; Polymorphism screening; Solvent parameters; Systematic polymorphism screening; Theoretical methods

Indexed keywords

EID: 84890776435     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/3527607889.ch11     Document Type: Chapter

References (92)

1. Bernstein, J., J. Phys. D: Appl. Phys., 26 (1993) B66-B76.
2. Brittain, H.G., Polymorphism in Pharmaceutical Solids, Marcel Dekker, Inc., New York (1999).
3. Byrn, S. R., Pfeiffer, R., Stowell, J. G., Solid State Chemistry of Drugs, 2nd edn., SSCI Inc., West Lafayette (1999).
4. Ostwald, W., Z. Phys. Chem., 22 (1897) 289-330.
5. Bernstein, J. Polymorphism in Molecular Crystals, Oxford Science Publications, Oxford (2002)
6. Threlfall, T., Org. Process Res. Dev., 4 (2000) 384-390.
7. Threlfall, T., Org. Process Res. Dev., 7 (2003) 1017-1027.
8. Etter, M. C., J. Phys. Chem., 95 (1991) 4601-4610.
9. Gavezzotti, A., Filippini, G., Chem. Commun., (1998) 287-294.
10. Rodriguez-Hornedo, N., Murphy, D., J. Pharm. Sci., 88 (1999) 651-660.
11. Datta, S., Grant, D.J.W., Crystal Growth & Design, 5 (2005) 1351-1357.
12. Davey, R. J., Allen, K., Blagden, N., Cross, W. I., Lieberman, H.F., Quayle, M.J., Righini, S., Seton, L., Tiddy, G. J.T., Cryst. Eng. Commun., 4 (2002) 257-264.
13. Gu, C.-H., Chatterjee, K., Young Jr., V., Grant, D.J.W., J. Crystal Growth, 235 (2002) 471-481.
14. Blagden, N., Davey, R., Chem. Br., 35 (1999) 44-47.
15. Beckmann, W., Otto, W., Budde, U., Org. Process Res. Dev., 5 (2001) 387-392.
16. Mukuta, T., Lee, A.Y., Kawakami, T., Myerson, A.S., Crystal Growth & Design, 5 (2005) 1429-1436.
17. Gu, C.-H., Young Jr., V., Grant, D. J.W., J. Pharm. Sci., 90 (2001) 1878-1890.
18. McCrone, W. C., Phys. Chem. Org. Solid State, 2 (1965) 725-767.
19. Griesser, U. J., Stowell, J. G. in Pharmaceutical Analysis (eds. Lee, D.C., Webb, M.L.), Blackwell Publishing Ltd., Oxford, UK (2003)
20. Newman, A.W., Stahly, G. P., Drugs Pharmaceutical Sci., 117 (2002) 1-57.
21. Guillory, J.K. in Polymorphism in Pharmaceutical Solids (ed. Brittain, H.G.), Marcel Dekker, New York (1999) pp. 125-181.
22. Kuhnert-Brandstätter, M., Thermomicroscopy in the Analysis of Pharmaceuticals, Pergamon Press, Oxford (1971).
23. Morissette, S. L., Almarsson ,O., Peterson, M.L., Remenar, J. F., Read, M.J., Lemmo, A.V., Ellis, S., Cima, M.J., Gardner, C. R., Adv. Drug Delivery Rev., 56 (2004) 275-300.
24. Price, C. P., Grzesiak, A. L., Matzger, A. J., J. Am. Chem. Soc., 127 (2005) 5512-5517.
25. Lang, M., Grzesiak, A. L., Matzger, A. J., J. Am. Chem. Soc., 124 (2002) 14834- 14835.
26. Cacciuto, A., Auer, S., Frenkel, D., Nature, 428 (2004) 404-406.
27. Trask, A.V., Motherwell, W.D. S., Jones, W., Chem. Commun., (2004) 890-891.
28. Trask, A.V., Motherwell, W.D. S., Jones, W., Crystal Growth Design, 5 (2005) 1013-1021.
29. Almarsson, ö., Zaworotko, M.J., Chem. Commun., (2004) 1889-1896.
30. Childs, S. L., WO 2004/064762 A2, Novel Cocrystallization.
31. Childs, S. L., Chyall, L. J., Dunlap, J.T., Coates, D. A., Stahly, B. C., Stahly, G. P., Cryst. Growth Design, 4 (2004) 441-449.
32. Zaccaro, J., Matic, J., Myerson, A. S., Garetz, B. A., Crystal Growth Design, 1 (2001) 5-8.
33. Beach, S., Latham, D., Sidgwick, C., Hanna, M., York, P., Org. Process Res. Dev., 3 (1999) 370-376.
34. Bonafede, S. J., Ward, M.D., J. Am. Chem. Soc., 117 (1995) 7853-7861.
35. Rodriguez-Spong, B., Price, C. P., Jayasankar, A., Matzger, A. J., Rodriguez- Hornedo, N., Adv. Drug Delivery Rev., 56 (2004) 241-274.
36. Dennehy, R. D., Org. Process Res. Dev., 7 (2003) 1002-1006.
37. Gu, C.-H., Li, H., Gandhi, R. B., Raghavan, K., Int. J. Pharmaceutics, 283 (2004) 117-125.
38. Mirmehrabi, M., Rohani, S., J. Pharm. Sci., 94 (2005) 1560-1576.
39. Snyder, L. R., J. Chromatogr. Sci., 16 (1978) 223-234.
40. Carlson, E. D., Design and Optimization in Organic Synthesis, Elsevier, Amsterdam (1992).
41. Blomsma, E., van Langevelde, A., Conference on Polymorphism and Crystallization, Barnett International, Brussels, September 29-30 (2003).
42. Singhal, D., Curatolo, W., Adv. Drug Delivery Rev., 56 (2004) 335-347.
43. Burger, A., Zur Auffindung und Herstellung neuer Kristallformen von Arzneistoffen, Vortrag zum 30. Jahrestag der Arbeitsgemeinschaft für Pharmazeutische Verfahrenstechnik e.V. (A. P.V.), Mainz (1984).
44. Griesser, U. J., PhD Thesis, Universität Innsbruck (1991).
45. Szelagiewicz, M., Marcolli, C., Cianferani, S., Hard, A. P., Vit, A., Burkhard, A., von Raumer, M., Hofmeier, U. C., Zilian, A., Francotte, E., Schenker, R., J. Therm.Anal. Cal., 57 (1999) 23-43.
46. Peterson, M.L., Morissette, S. L., McNulty, C., Goldsweig, A., Shaw, P., LeQuesne, M., Monagle, J., Encina, N., Marchionna, J., Johnson, A., Gonzalez- Zugasti, J., Lemmo, A.V., Ellis, S. J., Cima, M.J., Almarsson, O., J. Am. Chem. Soc., 124 (2002) 10 958-10 959.
47. Blatter, F., Szelagiewicz, M., von Raumer, M., WO 2005/037424 A1, Process for the Parallel Detection of Crystalline Forms of Molecular Solids.
48. Balbach, S., Korn, C., Int. J. Pharmaceutics, 275 (2004) 1-12.
49. Giron, D., Eng. Life Sci., 3 (2003) 103-112.
50. Huang, L.-F., Tong, W.-Q., Adv. Drug Delivery Rev., 56 (2004) 321-334.
51. Maier, W.-F., Klein, J., Lehmann, C., Schmidt, H.W., Offenlegungsschrift DE 198 22 077 A1, Kombinatorisches Verfahren zur Herstellung und Charakterisierung von kristallinen und amorphen Materialbibliotheken im Mikrogramm- Maßstab (1999).
52. Storey, R., Docherty, R., Higginson, P., Dallman, C., Gilmore, C., Barr, G., Dong, W., Crystallogr. Rev., 10 (2004) 45-56.
53. Carlton, D. L., Dhingra, O.P., Waters, P.W., WO 00/67872, High Throughput Crystal Form Screening Workstation and Method of Use.
54. Gardner, C. R., Walsh, C.T., Almarsson, ö., Nat. Rev., 3 (2004) 926-934.
55. Van Langevelde, A., Blomsma, E., Acta Crystallogr., Sect. A, 58 (2002) C9 (supplement).
56. Desrosiers, P., Carlson, E., Chandler, W., Chau, H., Cong, P., Doolen, R., Freitag, C., Lin, S., Masui, C., Wu, E., Crevier, T., Mullins, D., Song, L., Lou, R., Zhan, J., Tangkilisan, A., Ung, Q., Phan, K., Acta Crystallogr., Sect. A, 58 (2002) C9 (supplement).
57. Carlson, E. D., Cong, P., Chandler Jr., W. H., Chau, H.K., Crevier, T., Desrosiers, P. J., Doolen, R. D., Freitag, C., Hall, L. A., Kudla, T., Luo, R., Masui, C., Rogers, J., Song, L., Tangkilisan, A., Ung, K. Q., Wu, L., Pharmachem. (2003) 10-15.
58. Hilfiker, R., Berghausen, J., Blatter, F., Burkhard, A., De Paul, S. M., Freiermuth, B., Geoffroy, A., Hofmeier, U., Marcolli, C., Siebenhaar, B., Szelagiewicz, M., Vit, A., von Raumer, M., J. Therm. Anal. Cal., 73 (2003) 429-440.
59. Barr, G., Dong, W., Gilmore, C. J., J. Appl. Crystallogr., 37 (2004) 658-664.
60. Gilmore, C. J., Barr, G., Paisley, J., J. Appl. Crystallogr., 37 (2004) 231-242.
61. Kala, H., Haack, U., Pollandt, P., Brezesinski, G., Acta Pharm. Technol., 32 (1986) 72-77.
62. Krahn, F. U., Mielck, J. B., Pharm. Acta Helv., 62 (1987) 247-254.
63. Lowes, M.M.J., Caira, M.R., Lötter, A. P., van der Watt, J. G., J. Pharm. Sci., 76 (1987) 744-752.
64. Edwards, A. D., Shekunov, B.Y., Forbes, R.T., Grossmann, J. G., York, P., J. Pharm. Sci., 90 (2001) 1106-1114.
65. Rustichelli, C., Gamberini, G., Ferioli, V., Gamberini, M.C., Ficarra, R., Tommasini, S., J. Pharm. Biomed. Anal., 23 (2000) 41-54.
66. Lang, M., Kampf, J.W., Matzger, A. J., J. Pharm. Sci., 91 (2002) 1186-1190.
67. Grzesiak, A. L., Lang, M., Kim, K., Matzger, A. J., J. Pharm. Sci., 92 (2003) 2260-2271.
68. Fleischmann, S. G., Kuduva, S. S., Mc- Mahon, J. A., Moulton, B., Bailey Walsh, R. D., Rodriguez-Hornedo, N., Zaworotko, M.J., Crystal Growth Design, 3 (2003) 909-919.
69. Johnston, A., Florence, A. J., Kennedy, A. R., Acta Crystallogr., Sect. E, 61 (2005) o1777-o1779.
70. Johnston, A., Florence, A. J., Kennedy, A. R., Acta Crystallogr., Sect. E, 61 (2005) o1509-o1511.
71. Lohani, S., Zhang, Y., Chyall, L. J., Mougin-Andres, P., Muller, F. X., Grant, D.J.W., Acta Crystallogr., Sect. E, 61 (2005) o1310-o1312.
72. Behme, R. J., Brooke, D., J. Pharm. Sci., 80 (1991) 986-990.
73. Ceolin, R., Toscani, S., Gardette, M.-F., Agafonov, V. N., Dzyabchenko, A.V., Bachet, B., J. Pharm. Sci., 86 (1997) 1062-1065.
74. Griesser, U. J., Szelagiewicz, M., Hofmeier, U. C., Pitt, C., Cianferani, S., J. Therm. Anal. Cal., 57 (1999) 45-60.
75. Anquetil, P. A., Brenan, C. J. H., Marcolli, C., Hunter, I.W., J. Pharm. Sci., 92 (2003) 149-160.
76. Blatter, F., Cron-Eckhardt, B., Hofmeier, U.C., Koller, P., Marcolli, C., Szelagiewicz, M., WO 03/026797 A2, Sealing System with Flow Channels.
77. Szelagiewicz, M., Marcolli, C., Berghausen, J., Cron-Eckhardt, B., Hofmeier, U.C., Blatter, F., WO 2004/045769 A1, Multiple Sealing System for Screening Studies.
78. Bernstein, J., Davey, R. J., Henck, J.-O., Angew. Chem. Int. Ed., 38 (1999) 3441- 3461.
79. Grunenberg, A., Henck, J.-O., Siesler, H.W., Int. J. Pharmaceutics, 129 (1996) 147-158.
80. Marti, E., J. Therm. Anal. Cal., 33 (1998) 37-45.
81. Gu, C.-H., Grant, D. J.W., J. Pharm. Sci., 90 (2001) 1277-1287.
82. Yu, L., Reutzel, S. M., Stephenson, G. A., Pharmaceutical Sci. Technol. Today, 1 (1998) 118-127.
83. Gavezzotti, A., Acc. Chem. Res., 27 (1994) 309-314.
84. Dunitz, J. D., Chem. Commun., (2003) 545-548.
85. Karfunkel, H.R., Gdanitz, R. J., J. Comput. Chem., 13 (1992) 1171-1183.
86. Gavezzotti, A., Fillipini, G., J. Am. Chem. Soc., 117 (1995) 12299-12305.
87. Price, S. L., Wibley, K. S., J. Phys. Chem. A, 101 (1997) 2198-2206.
88. Beyer, T., Day, G. M., Price, S. L., J. Am. Chem. Soc., 123 (2001) 5086-5094.
89. Verwer, P., Leusen, F. J. J. in Reviews in Computational Chemistry (eds. Lipowitz, K. B., Boyd, D.B.), Wiley-VCH, New York (1998), Vol. 12, Chapter 7, p. 327.
90. Accelrys Inc., Cerius2 Modelling Environment, Accelrys Inc., San Diego (1999).
91. Price, S. L., Adv. Drug Delivery Rev., 56 (2004) 301-319.
92. Lommerse, J.P. M., Motherwell, W. D.S., Ammon, H.L., Dunitz, J. D., Gavezzotti, A., Hofmann, D.W. M., Leusen, F. J. J., Mooij, W.T. M., Price, S. L., Schweizer, B., Schmidt, M.U., van Eijck, B. P., Verwer, P., Williams, D.E., Acta Crystallogr., Sect. B, 56 (2000) 697-714.