A tale of two polymorphic pharmaceuticals: Pyrithyldione and propyphenazone and their 1937 co-crystal patent

Chemistry - A European Journal

Volumn 17, Issue 48, 2011, Pages 13445-13460

  Lemmerer, Andreas ^a   Bernstein, Joel ^b,c   Griesser, Ulrich J ^d   Kahlenberg, Volker ^d   Többens, Daniel M ^d   Lapidus, Saul H ^e   Stephens, Peter W ^e   Esterhuysen, Catharine ^f  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

^b BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^c NEW YORK UNIVERSITY ABU DHABI   (United Arab Emirates)

^d UNIVERSITY OF INNSBRUCK   (Austria)

^e STONY BROOK UNIVERSITY   (United States)

^f STELLENBOSCH UNIVERSITY   (South Africa)

Author keywords

co crystals; hot stage microscopy; pharmaceuticals; polymorphism; X ray diffraction

Indexed keywords

ACTIVE PHARMACEUTICAL INGREDIENTS; CO-CRYSTALS; CONTACT METHODS; CRYSTAL FORMS; CRYSTAL STRUCTURE ANALYSIS; CURRENT DRIVES; DRUG COMPOUNDS; HOT-STAGE MICROSCOPY; METASTABLE FORM; NON-STEROIDAL ANTI-INFLAMMATORY DRUGS; PHYSIOLOGICAL PROPERTIES; POLYMORPHIC FORMS; ROOM TEMPERATURE; STABLE FORM; SYNCHROTRON X RAY DIFFRACTION;

CRYSTALS; DRUG PRODUCTS; POLYMORPHISM; X RAY DIFFRACTION;

CRYSTAL STRUCTURE;

DRUG DERIVATIVE; NONSTEROID ANTIINFLAMMATORY AGENT; PHENAZONE; PROPYPHENAZONE; PYRIDONE DERIVATIVE; PYRITHYLDIONE;

ARTICLE; CHEMISTRY; CRYSTALLIZATION; TEMPERATURE; X RAY DIFFRACTION;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTIPYRINE; CRYSTALLIZATION; PYRIDONES; TEMPERATURE; X-RAY DIFFRACTION;

EID: 81755162257     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100667     Document Type: Article

References (84)

1. F. Hoffmann-La Roche & Co, Basel (Switzerland) CH 187826, 1937.
2. G. P. Stahly, Cryst. Growth Des. 2009, 9, 4212-4229
3. S. L. Childs, M. J. Zaworotko, Cryst. Growth Des. 2009, 9, 4208-4211.
4. Ö. Almarsson, M. J. Zaworotko, Chem. Commun. 2004, 1889-1896
5. P. Vishweshwar, J. A. McMahon, J. A. Bis, M. J. Zaworotko, J. Pharm. Sci. 2006, 95, 499-516
6. N. Schultheiss, A. Newman, Cryst. Growth Des. 2009, 9, 2950-2967
7. A. M. Chen, M. E. Ellison, A. Peresypekin, R. M. Wenslow, N. Variankaval, C. G. Savarin, T. K. Natishan, D. J. Mathre, P. G. Dormer, D. H. Euler, R. G. Ball, Z. Ye, Y. Wang, I. Santos, Chem. Commun. 2007, 419-421
8. N. Shan, M. J. Zaworotko, Drug Discovery Today 2008, 13, 440-446
9. M. K. Stanton, S. Tufekcic, C. Morgan, A. Bak, Cryst. Growth Des. 2009, 9, 1344-1352
10. A. V. Yadav, A. S. Shete, A. P. Dabke, P. V. Kulkarni, S. S. Sakhare, Indian J. Pharm. Sci. 2009, 71, 359-370.
11. M. L. Peterson, M. B. Hickey, M. J. Zaworotko, Ö. Almarsson, J. Pharm. Pharm. Sci. 2006, 9, 317-326
12. F. Lara-Ochoa, G. Espinosa-Pérez, Cryst. Growth Des. 2007, 7, 1213-1215.
13. Ö. Almarsson, M. B. Hickey, M. Peterson, M. J. Zaworotko, B. Moulton, N. Rodríguez-Hornedo, (Saliwanchik Lloyd & Saliwanchik, Gainesville), US-A 0059356A1, 2007.
14. S. J. Nehm, B. Rodríguez-Spong, N. Rodríguez-Hornedo, Cryst. Growth Des. 2006, 6, 592-600
15. D. J. Good, N. Rodríguez-Hornedo, Cryst. Growth Des. 2009, 9, 2252-2264
16. N. Blagden, M. deMatas, P. T. Gavan, P. York, Adv. Drug Delivery Rev. 2007, 59, 617-630.
17. J. Lu, S. Rohani, Org. Process Res. Dev. 2009, 13, 1269-1275
18. S. Basavoju, D. Boström, S. P. Velaga, Cryst. Growth Des. 2006, 6, 2699-2708
19. S. L. Childs, L. J. Chyall, J. T. Dunlap, V. N. Smolenskaya, B. C. Stahly, G. P. Stahly, J. Am. Chem. Soc. 2004, 126, 13335-13342
20. J. F. Remenar, S. L. Morissette, M. L. Peterson, B. Moulton, J. M. MacPhee, H. R. Guzman and Ö. Almarsson, J. Am. Chem. Soc. 2003, 125, 8456-8457
21. S. Basavoju, D. Boström, S. P. Velaga, Pharm. Res. 2008, 25, 530-541.
22. M. Khan, V. Enkelmann, G. Brunklaus, J. Am. Chem. Soc. 2010, 132, 5254-5263.
23. S. G. Fleischman, S. S. Kuduva, J. A. McMahon, B. Moulton, R. D. B. Walsh, N. Rodríguez-Hornedo, M. J. Zaworotko, Cryst. Growth Des. 2003, 3, 909-919
24. N. Rodríguez-Hornedo, S. J. Nehm, K. F. Seefeldt, Y. Pagán-Torres, C. J. Falkiewicz, Mol. Pharm. 2006, 3, 362-367
25. K. Seefeldt, J. Miller, F. Alvarez-NÚñez, N. Rodríguez-Hornedo, J. Pharm. Sci. 2007, 96, 1147-1158
26. N. Chieng, M. Hubert, D. Saville, T. Rades, J. Aaltonen, Cryst. Growth Des. 2009, 9, 2377-2386
27. E. Gagniere, D. Mangin, F. Puel, C. Bebon, J.-P. Klein, O. Monnier, E. Garcia, Cryst. Growth Des. 2009, 9, 3376-3383
28. A. Y. Sheikh, S. A. Rahim, R. B. Hammond, K. J. Roberts, CrystEngComm 2009, 11, 501-509.
29. S. Aitipamula, P. S. Chow, R. B. H. Tan, CrystEngComm 2009, 11, 1823-1827.
30. J. Bernstein, Polymorphism in Molecular Crystals, Oxford University Press, Oxford, 2002
31. J. Bernstein, Cryst. Growth Des. 2011, 11, 632-650.
32. S. Wishkerman, J. Bernstein, Chem. Eur. J. 2008, 14, 197-203
33. S. Roy, R. Banerjee, A. Nangia, G. J. Kruger, Chem. Eur. J. 2006, 12, 3777-3788
34. M. R. Chierotti, L. Ferrero, N. Garino, R. Gobetto, L. Pellegrino, D. Braga, F. Grepioni, L. Maini, Chem. Eur. J. 2010, 16, 4347-4358
35. D. Braga, F. Grepioni, L. Maini, M. Polito, K. Rubini, M. R. Chierotti, R. Gobetto, Chem. Eur. J. 2009, 15, 1508-1515
36. A. Gavezzotti, G. Filippini, J. Kroon, B. P. can Eijck, P. Klewinghais, Chem. Eur. J. 1997, 3, 893-899.
37. A. Llinàs, J. M. Goodman, Drug Discovery Today 2008, 13, 198-210
38. D. E. Braun, T. Gelbrich, R. K. R. Jetti, V. Kahlenberg, S. L. Price, U. J. Griesser, Cryst. Growth Des. 2008, 8, 1977-1989
39. U. J. Griesser, R. K. R. Jetti, M. F. Haddow, T. Brehmer, D. C. Apperley, A. King, R. K. Harris, Cryst. Growth Des. 2008, 8, 44-56
40. D. E. Braun, D. M. Többens, V. Kahlenberg, J. Ludescher, U. J. Griesser, Cryst. Growth Des. 2008, 8, 4109-4119
41. J. Lu, S. Rohani, Curr. Med. Chem. 2009, 16, 884-905.
42. P. Vishweshwar, J. A. McMahon, M. L. Peterson, M. B. Hickey, T. R. Shattock, M. J. Zaworotko, Chem. Commun. 2005, 4601-4603.
43. "With respect to the issue that co-crystalline materials might be less prone to polymorphism, we think that this is not so, at least not in co-crystals containing strong hydrogen-bonded units.", D. Braga, G. Palladino, M. Polito, K. Rubini, F. Grepioni, M. R. Chierotti, R. Gobetto, Chem. Eur. J. 2008, 14, 10149-10159.
44. W. Lang, Arzneim.-Forsch. 1951, 1, 314.
45. A. Burger, R. Ramberger, Mikrochim. Acta 1981, 75, 217-225.
46. M. Kuhnert-Brandstätter, A. Burger, Pharm. Ind. 1972, 34, 496- 501.
47. B. W. Müller, Y. Beer, Acta Pharm. Technol. 1982, 28, 97-102.
48. S. AŽalac, M. Z. I. Khan, V. Gabelica, M. Tudja, E. Meštrović, M. Romih, Chem. Pharm. Bull. 1999, 47, 302-307.
49. G. Dörler, PhD Thesis, University of Innsbruck (Austria), 1982.
50. A. Burger, R. Ramberger, Mikrochim. Acta II 1979, 72, 259-271.
51. E. F. Westrum, J. P. McCullogh, in Physics and Chemistry in the Organic Solid State, Vol.1 (Eds.:, D. Fox, M.M. Labes, A. Weissenberger,), Interscience, New York, London, Sydney, 1963, pp. 1-178.
52. A. Lemmerer, N. B. Báthori, C. Esterhuysen, S. A. Bourne, M. R. Caira, Cryst. Growth Des. 2009, 9, 2646-2655
53. R. J. Davey, Chem. Commun. 2003, 1463-1467
54. B. Lou, D. Boström, S. P. Velaga, Cryst. Growth Des. 2009, 9, 1254-1257
55. I. Weissbuch, M. Lahav, L. Leiserowitz, Cryst. Growth Des. 2003, 3, 125-150
56. E. H. Lee, S. X. M. Boerrigter, A. C. F. Rumondor, S. P. Chamarthy, S. R. Byrn, Cryst. Growth Des. 2008, 8, 91-97.
57. J. Bernstein, R. E. Davis, L. Shimoni and N.-L. Chang, Angew. Chem. 1995, 107, 1689-1708
58. Angew. Chem. Int. Ed. Engl. 1995, 34, 1555-1573.
59. D. E. Braun, T. Gelbrich, V. Kahlenberg, R. Tessadri, J. Wieser, U. J. Griesser, J. Pharm. Sci. 2009, 98, 2010-2026
60. U. J. Griesser, D. Weigand, J. Rollinger, M. Haddow, E. Gstrein, Therm. Anal. Cal. 2004, 77, 511-522.
61. J.-F. Bérar, P. Lelann, J. Appl. Crystallogr. 1991, 24, 1-5.
62. D. J. Berry, C. C. Seaton, W. Clegg, R. W. Harrington, S. J. Coles, P. N. Horton, M. B. Hursthouse, R. Storey, W. Jones, T. Friščić, N. Blagden, Cryst. Growth Des. 2008, 8, 1697-1712
63. A. Lemmerer, C. Esterhuysen, J. Bernstein, J. Pharm. Sci. 2010, 99, 4054-4071.
64. D. R. Weyna, T. Shattock, P. Vishweshwar, M. J. Zawortko, Cryst. Growth Des. 2009, 9, 1106-1123
65. G. Kaupp, CrystEngComm 2009, 11, 388-403
66. T. Friščić, W. Jones, Cryst. Growth Des. 2009, 9, 1621-1637.
67. Gaussian09, RevisionA.02, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian, Inc., Wallingford CT, 2009.
68. Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215-241.
69. W. J. Hehre, R. Ditchfield, J. A. Pople, J. Chem. Phys. 1972, 56, 2257-2261
70. P. C. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213-222.
71. B. J. Ransil, J. Chem. Phys. 1961, 34, 2109-2118.
72. S. F. Boys, F. Bernardi, Mol. Phys. 1970, 19, 553-566.
73. CrysAlisPro, Version 1.171.33.34d, Oxford Diffraction, Oxford (released: 27 Feb., 2009).
74. XPREP2, Version 6.14, Bruker AXS, Madison, 2003.
75. L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837-838.
76. G. M. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112-121.
77. L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
78. A. L. Spek, J. Appl. Crystallogr. 2003, 36, 7-13.
79. W. T. Pennington, J. Appl. Crystallogr. 1999, 32, 1028-1029
80. A. A. Coelho, J. Appl. Crystallogr. 2003, 36, 86-95
81. V. Favre-Nicolin, R. ČernÝ, Z. Kristallogr. 2004, 219, 847-856.
82. M. S. Gordon, M. W. Schmidt, in Theory and Applications of Computational Chemistry: The First Forty Years, (Eds.:, C.E. Dykstra, G. Frenking, K.S. Kim, G.E. Scuseria,), Elsevier, Amsterdam, 2005.
83. J. Rodríguez-Carvajal, FullProf.2k, Version4.30, LLB JRC, Saclay, 2008.
84. L. W. Finger, D. E. Cox, A. P. Jephcoat, J. Appl. Crystallogr. 1994, 27, 892-900.