Layered structure and swelling behavior of a multiple hydrate-forming pharmaceutical compound

Crystal Growth and Design

Volumn 9, Issue 4, 2009, Pages 1833-1843

  Kiang, Y H ^a,c   Xu, Wei ^a   Stephens, Peter W ^b   Ball, Richard G ^a   Yasuda, Nobuyoshi ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b STONY BROOK UNIVERSITY   (United States)

^c AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 65249143835     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg801004a     Document Type: Article

References (45)

1. Zielke, R. C: Pinnavania, T. J.; Mortland, M. M. Adsorption and Reactions of Selected Organic Molecules on Clay Mineral Surfaces; Soil Science Society of America: Madison, 1989; pp 81-97.
2. Mallouk, T. E.; Gavin, J. A. Molecular recognition in lamellar solids and thin films. Ace. Chem. Res. 1998, 31, 209-217.
3. O'hare, D. Organic and organometallic guests intercalated in layered lattices. New J. Chem. 1994, 18, 989-998.
4. Newman, S. P.; William, J. Synthesis, characterization and application of layered double hydroxides containing organic guests. New J. Chem. 1998', 22. 1 OS-115
5. Sposito, G. The Chemistry of Soils; Oxford University Press: New York, 1989.
6. Liebau. F. Structural Chemistry of Silicates; Springer-Verlag: Berlin, 1985.
7. Biradha, K.; Dennis, D.; MacKinnon, V.; Sharma, C.; Zaworotko, M. Supramolecular synthesis of organic laminates with affinity for aromatic guests: a new class of clay mimics. J. Am. Chem. Soc. 1998, 120, 11894-11903.
8. Coleman, A. W.; Bott, S. G.; Morley, S. D.; Means, C. M.; Robinson, K. D.; Zhang, Ft.; Atwood, J. L. Sodium calix[4] arenesulfonate with a layered structure. An organic clay? Angew. Chem., Int. Ed. Engl. 1988, 27, 1361-1362.
9. Matsumoto. A.; Oshita, S.; Fujioka, D. A novel organic intercalation system with layered polymer crystals as die host compounds derived from 1,3-diene carboxylic acids. J. Am. Chem. Soc. 2002, 124 (46), 13749-56.
10. Brouwer, E. B.; Udachin, K. A.; Enright, G. D.; Ripmeester, J. A.; Ooms, K. J.; Halchuk, P. A. Self-inclusion and paraffin intercalation of the p-ter-butylcalix[4]arene host: a neutral organic clay mimic. Chem. Commun. 2001, 565-566.
11. Higgos, J. J. W. Clay as a barrier to radionuclide migration. Prog. Nucl. Energy 1987, 19, 173-207.
12. Pusch, R. Use of bentonite for isolation of radioactive waste products. Clay Minerals 1992, 27, 353-361.
13. Karaborni, S.; Smit, B.; Heidug, W.; Urai, J.; van Oort, E. The swelling of clays: molecular simulations of the hydration of montmorillonite. Science 1996, 271, 1102-1104.
14. Young, D. A.; Smith, D. E. Simulation of clay mineral swelling and hydration: dependence upon interlayer ion size and charge. J. Phys. Chem. B 2000, 104, 9163-9170.
15. Mooney, R. W.; Keenan, A. G.; Wood, L. A. Adsorption of water vapor by montmorillonite. II. Effect of exchangeable ions and lattice swelling as measured by X-ray diffraction. J. Am. Soc. Chem. 1952. 74, 1371-1374.
16. Hensen, E. J.; Smit, B. Why clays swell.J. Phys. Chem. B 2002, 106, 12664-12667.
17. Morris, K. R.; Fakes, M. G.; Thakur, A. B.; Newman, A. W.; Singh, A. K.; Venit, J. J.; Spagnuolo, C. J.; Serajuddin, A. T. M. An integrated approach to the selection of optimal salt form for a new drug candidate. Int. J. Pharm. 1994, 105, 209-217.
18. Morris, K. R. Structural aspects of hydrates and solvates. In Polymorphism in Pharmaceutical Solids: Brittain, H. G., Ed.; Marcel Dekkerlnc: New York, 1999; pp 125-181.
19. Stahl, P. H. The problems of drag interaction with excipients. In Towards Better Safety of Drugs and Pharmaceutical Products; Draimar, D. D., Ed.; Elsevier: Amsterdam, 1980; pp 265-280.
20. Kuhnert-Brandstatter, M.; Gasser, P. Solvates and polymorphic modifications of steroid hormones. IIL Microchem. J. 1971, 16, 590-601.
21. Kuhnert-Brandstatter, M. Thermomicroscopy in the Analysis of Pharmaceuticals; Pergamon Press: New York, 1971.
22. Giron, D.; Goldbronn, C; Mutz, M.; Pfeffer, S.; Piechon, P.; Schwab, P. Solid State Characterizations of Pharmaceutical Hydrates. J, Therm. Anal. Calorim. 2002, 68 (2), 453-465.
23. Cox, J. S. G.; Woodard, G. D.; McCrone, W. C. Solid-state chemistry of cromolyn sodium (disodium cromoglycate). J. Pharm. Sci. 1971, 60, 1458-1465.
24. Stephenson, G. A.; Diseroad, B. A. Structural relationship and desolvation behavior of cromolyn, cefazolin and fenoprofen sodium hydrates. M. J. Pharm. 2000, 198 (2), 167-77.
25. Karle, I. L.; Ranganathan, D.; Haridas, V. A persistent preference for layer motifs in self-assemblies of squarates and hydrogen squarates by hydrogen bonding [X-H⋯O; X = N, O, or C]: A crystallographic study of five organic salts. J. Am. Chem. Soc. 1996, 118, 7128-7133.
26. Gong, B.; Zheng, C; Skrzypczak-Jankun, E.; Zhu, J. Two-dimensional molecular layers: interplay of H-bonding and van der waals interactions in the self-assembly of N,N -dialkylsulfamides. Ore. Lett. 2000 2, (21), 3273-3275.
27. Chang, Y. L.; West, M. A.; Howler, F. W.; Lauher, J. W. An approach to the design of molecular solids. Strategies for conttolling the assembly of molecules into two-dimensional layerd structures. J. Am. Chem. Soc. 1993, 115, 5991-6000.
28. Visser, J. A fully automatic program for finding the unit cell from powder data. J. Awl. Crystallogr. 1969, 2, 89-95.
29. Bruker AXS TOPAS V3: General Profile and Structure Analysis Software for Powder Diffraction Data, User's Manual; Bruker AXS: Karlsruhe, Germany, 2005.
30. Material Studio: Accelrys Inc: San Diego, 2001.
31. Ceriusl; Accelrys Inc: San Diego, 2001.
32. Venkataraman, D.; Lee, S.; Zhang, J.; Moore, J. S. An organic solid with wide channels based on hydrogen bonding between macrocycles. Nature 1994, 371, 591-593.
33. Gardner, G. B.; Venkataraman, D.; Moore, J. S.; Lee, S. Spontaneous assembly of a hinged coordination network. Nature 1995, 374, 792-795.
34. Kiang, Y. H.; Gardner, G. B.; Lee, S.; Xu, Z.; Lobkovsky, E. B. Variable pore size, variable chemical functionality, and an example of reactivity within porous phenylacetylene silver salts. J. Am. Chem. Soc. 1999, 121, 8204-8215.
35. Engle, G. E.; Wilke, S.; Konig, O.; Harris, K. D. M.; Leusen, F. J. J. PowderSolve: A Complete Package for Crystal Structure Solution from Powder Diffraction Patterns. J. Appl. Cryst. 1999, 32, 1169-1179.
36. Kiang, Y. H.; Huq, A.; Stephens, P. W.; Xu, W. Structure determination of enalapril maleate form II from high-resolution X-ray powder diffraction data. LPharm. Sci. 2003. 92 (9). 1844-1853.
37. Coelho, A. A. Whole-profile structure solution from powder diffraction data using simulated annealing. J. Ann. Crystallogr. 2000, 33, 899- 908.
38. Spek. A. L. PLATON, A multipurpose crystallographic tool. J. Appl. Crystallogr. 2003, 36. 7-13.
39. Pawley, G. S. Unit-cell refinement from powder diffraction scans. J. Appl. Crystallogr. 1981, 14, 357-361.
40. Connolly, M. L. Analytical molecular surface calculation. J. Appl. Crystallogr. 1983, 16, 548-558.
41. van de Streek, J. All series of multiple solvates (including hydrates) from the Cambridge Structural Database, Cryty Eng. Comm. 2007, 9, 350-352.
42. Dunitz, J. D.; Seiler, P. 1,4,7,10,13,16-Hexaoxacyclootadecane. Acta Crystallogr. B 1974, B30 (11), 2739-1741.
43. Mootz, D.; Albert, A.; Schaefgen, S.; Staeben, D. Hydrates of weak and strong bases. 12. 18-Crown-6 and water: crystal structure of a binary hydrate. J. Am. Soc. Chem. 1994, 116 (26), 12045-12046.
44. Albert, A.; Mootz, D. Hydrates of weak and strong bases. Part 17. Formation and crystal structures of the hydrates of 18-crown-6. Z. Naturforsch. 11 1997. 52 (5), 615-619.
45. Reutzel-Edens, S. M.; Bush, J. K.; Magee, P. A.; Stephenson, G. A.; Byrn, S. R. Anhydrates and hydrates of olanzapine: crystallization, solid-state characterization, and structural relationships. Cryst. Growth. Des. 2003, 3, 897-907.