Polymorphism in molecular crystals: Stabilization of a metastable form by conformational mimicry

Journal of the American Chemical Society

Volumn 119, Issue 7, 1997, Pages 1767-1772

  Davey, R J ^a   Blagden, N ^a   Potts, G D ^a   Docherty, R ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

GLUTAMIC ACID;

ARTICLE; CRYSTALLOGRAPHY; DRUG STABILITY; DRUG STRUCTURE; PROTEIN POLYMORPHISM;

EID: 0030944392     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9626345     Document Type: Article

References (28)

1. Desiraju, G. R. Crystal Engineering; Materials Science Monographs, 54. Elsevier: Amsterdam, 1989.
2. Gavezzotti, A. Acc. Chem. Res. 1994, 27, 309-314.
3. Gavezzotti, A.; Filippini, G. J. Am. Chem. Soc. 1996, 118, 7153-7157.
4. Karfunkel, H.; Gdanitz, R. J. J. Comput. Chem. 1992, 13, 1171-1183.
5. Ostwald, W. Grundriss der Allgemeinen Chemie, Leipzig, 1899.
6. Cardew, P. T.; Davey, R. J. Tailoring of Crystal Growth; Institution of Chemical Engineers, UK (North West Branch), 1982; pp 1-7. Cardew, P. T.; Davey, R. J. Faraday Discussions 1993, No. 95, 160-162.
7. Cardew, P. T.; Davey, R. J. Tailoring of Crystal Growth; Institution of Chemical Engineers, UK (North West Branch), 1982; pp 1-7. Cardew, P. T.; Davey, R. J. Faraday Discussions 1993, No. 95, 160-162.
8. Davey, R. J. Separation Technology The Next Ten Years; Garside, J., Ed.; Institution of Chemical Engineers: UK, 1994; pp 73-95.
9. Davey, R. J. Manufacturing Chemist 1990, Nov, 25-29.
10. Ranitidine hydrochloride, marketed by Glaxo pic under the tradename "Zantac" is known to be polymorphic. In a recent patent litigation (Glaxo Inc. (1993), Plaintiff V. Novopharm Ltd., Defendant, No. 91-759-CTV-% BO United States District Court for the Eastern District of California, Raleigh Division 1993 U. S. Dist. LEWIS 13928) Glaxo's patent protection based on this polymorphism has been challenged.
11. Dunitz, J. D.; Bernstein, J. Acc Chem Res. 1995, 28, 193-200.
12. Davey, R. J.; Maginn, S. J.; Andrews, S. J.; Buckley, A. M.; Cottier, D.; Dempsey, P.; Rout, J. E.; Stanley, D. R.; Taylor, A. Nature 1993, 366, 248-250.
13. Staab, E.; Addadi, L.; Leiserowitz, L.; Lahav, M. Adv. Mater. 1990, 2, 40-43.
14. Weissbuch, I.; Leiserowitz, L.; Lahav, M. Adv. Mater. 1994, 6, 952 -956.
15. Bernstein, J.; Hagler, A. T. J. Am. Chem. Soc. 1978, 100, 673-681.
16. Lehmann, M. S.; Nunes, A. C. Acta Crystallogr. 1980, B36, 1621-1625.
17. Lehmann, M. S.; Koetzle, T. F.; Hamilton, W. C. J. Cryst. Mol. Struct. 1972, 2, 225-233.
18. Bernstein, J. Acta Crystallogr. 1991, B47, 1004-1010.
19. Kitamura, M. J Cryst. Growth 1989, 96, 541-546.
20. Kitamura, M.; Funahara, H. J. Chem. Eng. Jpn. 1994, 27, 124-126.
21. Cardew, P. T.; Davey, R. J. Proc. Roy. Soc. (London) 1985, A393, 415-428.
22. Mayo, S. L.; Olafson, B.; Goddard, W. A. J. Phys. Chem. 1990, 94, 8897-8909.
23. Clark, M.; Crammer, R. D.; Van Opdenbosch, N. J. Comput. Chem. 1989, 10, 982-1012.
24. Stewart, J. J. P. MOPAC 6.0, QCPE No. 445, 1990.
25. Allinger, N. L.; Burkit, U. ACS Monograph No. 177; American Chemical Society: Washington DC, 1982.
26. Hirayama, N.; Shirahata, K.; Ohashi, Y.; Sasada, Y. Bull. Chem. Soc. Jpn. 1980, 53, 30-35.
27. Duchamp, D. J.; Marsh, R. E. Acta Crystallogr. 1969, B25, 5-19.
28. All packing diagrams were visualized using CERIUS, molecular modeling software, MSI/Biosym Inc., Cambridge, UK.