Crystal Polymorphism: Challenges at the Crossroads of Science and Technology

Making Crystals by Design: Methods, Techniques and Applications

Volumn , Issue , 2007, Pages 293-314

  Braga, Dario ^a   Bernstein, Joel ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

Author keywords

Crystal polymorphism; Multiple crystal forms

Indexed keywords

EID: 84889630353     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527610112.ch11     Document Type: Chapter

References (71)

1. M.H. Klaproth Bergmannische J. I, 1798, 294.
2. E. Mitscherlich, Abhl. Akad. Berlin, 1823, 43.
3. W. C. McCrone, in Polymorphism in Physics and Chemistry of the Organic Solid State, D. Fox, M. M. Labes, A. Weissenberg (Eds.), Interscience, New York, 1965, vol. II, p. 726
4. J. Bernstein, Polymorphism in Molecular Crystals, Oxford University Press, Oxford, 2002
5. D. Braga, Chem. Commun., 2003, 2751.
6. G. R. Desiraju, Crystal Engineering: The Design of Organic Solids, Elsevier, Amsterdam, 1989
7. D. Braga, F. Grepioni, A. G. Orpen (Eds.), Crystal Engineering: from Molecules and Crystals to Materials, Kluwer Academic Publishers, Dordrecht, 1999
8. D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev., 1998, 98, 1375
9. A. J. Blake, N. R. Champness, P. Hubberstey, W. S. Li, M. A. Withersby and M. Schroder, Coord. Chem. Rev., 1999, 183, 117
10. B. Moul-ton, M. J. Zaworotko, Chem. Rev., 2001, 101, 1629.
11. A. Burger, Topics in Pharmaceutical Sciences, D. D. Breimer, P. Speiser, Elsevier, Amsterdam, 1983, p. 347
12. T. L. Threlfall, Analyst, 1995, 120, 2435.
13. S. Chen, I. Guzei, L. Yu, J. Am. Chem. Soc., 2005, 127, 9881
14. L. Yu, G. A. Stephenson, C. A. Mitchell, C. A. Bunnell, S. V. Snorek, J. J. Bowyer, T. B. Borchardt, J. G. Stowell, S. R. Byrn, J. Am. Chem. Soc., 2000, 122, 585.
15. R. K. Merton, E. Barber, The Travels and Adventures of Serendipity, Princeton University Press, Princeton, 2004.
16. J. A. Ibers, Acta Crystalogr., Sect. C, 2001, 57, 641.
17. J. Bernstein, Chem. Commun., 2005, 5007.
18. A. Grunenberg, J.-O. Henck, H. W. Siesler, Int. J. Pharm. 1996, 129, 147
19. J.-O. Henck, M. Kuhnert-Brandstatter, J. Pharm. Sci. 1999, 88, 103.
20. C. J. Brown, M. Ehrenberg Acta Crystallogr., Sect. C 1985, 41, 441
21. G. E. Hardy, W. C. Kaska, B. P. Chandra, J. I. Zink J. Am. Chem. Soc. 1981, 103, 1074
22. H. Takazawa, S. Ohba, Y. Saito Acta Crystallogr., Sect. C. 1986, 42, 1880
23. Tian-Huey Lu, P. Chattopadhyay, Fen-Liang Liao, Jem-Mau Lo, Anal. Sci. 2001, 17, 905.
24. T. C. Lewis, D. A. Tocher, S. L. Price, Cryst. Grow. Des., 2004, 4, 979.
25. W. Bolton, Acta Crystallogr., 1963, 16, 166
26. G. A. Jeffrey, S. Ghose, J. O. Warwicker, Acta Crystallogr., 1961, 14, 881
27. A. R. Al-Karaghouli, B. Abdul-Wahab, E. Ajaj, S. Al-Asaff, Acta Crystallogr., Sect. B 1977, 33, 1655
28. G. S. Nichol, W. Clegg, Acta Crystallogr., Sect. B 2005, 61, 464.
29. S. L. Morissette, S. Soukasenem, D. Levinson, M. J. Cima, Ö. Almarsson, Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 2180.
30. G. R. Desiraju (Ed.), Crystal Design: Structure and Function, Wiley, Chichester, 2003
31. D. Braga, F. Grepioni, Angew. Chem. Int. Ed., 2004, 43, 4002.
32. J. Bauer, S. Spanton, R. Henry, J. Quick, W. Dziki, W. Porter, J. Morris, Pharm. Res., 2001, 18, 859.
33. W. I. F. David, K. Shankland, C. R. Pulham, N. Blagden, R. Davey, M. Song, Angew. Chem., Int. Ed. 2005, 44, 7032
34. N. Blagden, R. Davey, G. Dent, M. Song, W. I. F. David, C. R. Pulham, K. Shankland, Cryst. Growth Des. 2005, 5, 2218.
35. Ö. Almarsson, M. J. Zaworotko, Chem. Commun., 2004, 1889
36. C. B. Aakeröy, A. M. Beatty, B. A. Helfrich, Angew. Chem., Int. Ed., 2001, 40, 3240.
37. C. P. Price, A. L. Grzesiak, A. J. Matzger, J. Am. Chem. Soc., 2005, 127, 5512.
38. D. Braga, F. Grepioni, Chem. Commun., 2005, 3635.
39. A. V. Trask, N. Shan, W. D. S. Motherwell, W. Jones, S. Feng, R. B. H. Tan, K. J. Carpenter, Chem. Commun., 2005, 880.
40. E. Y. Cheung, S. J. Kitchin, K. D. M. Harris, Y. Imai, N. Tajima, R. Kuroda, J. Am. Chem. Soc., 2003, 125, 14658.
41. A. Burger, U. J. Griesser, Eur. J. Pharm. Biopharm., 1991, 37, 118.
42. P. York, Chem. World, 2005, 2, 50
43. B. Yu. Shekunov, P. York, J. Cryst. Growth, 2001, 211, 122.
44. M. Rafilovich, J. Bernstein, R. Harris, D. Apperley, P. Panagiotopolis, S. L. Price Cryst. Growth Des. 2005, 5, 2197.
45. R. Hiremath, J. A. Basile, S. W. Varney, J. A. Swift, J. Am. Chem. Soc. 2005, 127, 18321.
46. A. Offret, H. Vittenet, Bull. Soc. Chim. Fr., 1899, 21, 152
47. A. Offret, H. Vittenet, Bull. Soc. Chim. Fr., 1899, 21, 788
48. A. Offret, H. Vittenet, Bull. Soc. Chim. Fr. 1899, 22, 627.
49. P. H. R. Groth, An Introduction to Chemical Crystallography (trans. H. Marshall), Gurnery & Jackson, London, 1906, pp. 28-31.
50. M. C. Etter, Z. Urbañczyk-Lipkowska, M. Zia-Ebrahimi, T. W. M. Panunto, J. Am. Chem. Soc. 1990, 112, 8415.
51. K.-S.Huang, D. Britton, M. C. Etter, S. R. Byrn, J. Mater. Chem. 1995, 5, 379.
52. J. Bernstein, in Organic Solid State Chemistry, G. R. Desiraju (Ed.), Elsevier, Amsterdam, 1987, p. 471.
53. A. Grunenberg, J.-O. Henck, H. W. Siesler, Int. J. Pharm. 1995, 129, 147.
54. J. P. M. Lommerse, W. D. S. Motherwell, H. L. Ammon, J. D. Dunitz, A. Gavezzotti, D. W. M. Hofmann, F. J. J. Leusen, W. T. M. Mooij, S. L. Price, B. Schweizer, M. U. Schmidt, B. P. van Eijck, P. Verwer, D. E. Williams, Acta Crystallogr. B, 2000, 56, 697
55. W. D. S. Motherwell, H. L. Ammon, J. D. Dunitz, A. Dzyabchenko, P. Erk, A. Gavezzotti, D. W. M. Hofmann, F. J. J. Leusen, J. P. M. Lommerse, W. T. M. Mooij, S. L. Price, H. Scheraga, B. Schweizer, Acta Crystallogr. B, 2002, 58, 647.
56. J. Bauer, S. Spanton, R. Henry. J. Quick, W. Dziki, W. Porter, J. Morris, J. Pharm. Res. 2001, 6, 59.
57. A. F. Findlay, The Phase Rule and Its Applications, A.N. Campbell, N. O. Smith (Eds.), Dover Publications, New York, 9th edn., 1951, pp. 7-16.
58. M. J. Buerger, M. C. Bloom, Z. Kristallogr. 1937, 96, 182.
59. N. N. Sirota, Cryst. Res. Technol. 1982, 17, 661.
60. M. Kuhnert-Brandstatter, Pure Appl. Chem. 1965, 10, 133.
61. M. Kuhnert-Brandstatter, Thermomicroscopy in the Analysis of Pharmaceuticals, International Series of Monographs in Analytical Chemistry, R. Belcher, M. Freiser, (Eds.), Pergamon, Oxford, 1971, Vol. 445.
62. S. R. Byrn, R. R. Pfeiffer, J. G. Stowell, Solid State Chemistry of Drugs, SSCI, Inc., West Lafayette, 2nd edn., 1999.
63. S. R. Byrn, personal communication
64. J. A. R. P. Sarma, G. R. Desiraju, Crystal Engineering. The Design and Application of Functional Solids, Kluwer, 1999, p. 325
65. U. Griesser, Acta Crystallogr., Sect. A 2002, 58 (Supplement), C241
66. U. Griesser, A. Burger, IUCr Congress, Glasgow, Abstract P09.013, p. 533
67. C. H. Gorbitz, H. P. Hersleth, Acta Crystallogr., Sect. B 2000, 56, 526.
68. http://www.fda.gov/cder/guidance/ 6154dft.htm
69. http://www.european-patent-office.org
70. J. Bernstein, Polymorphism in Pharmaceutical Technology, R. Hilfiker (Ed.), Elsevier, Amsterdam, 2006.
71. SmithKline Beecham et al. vs. Apotex Corp. et al., United States District Court, Northern District of Illinois 98C3952.