Improving the solubility of agomelatine via cocrystals

Crystal Growth and Design

Volumn 12, Issue 5, 2012, Pages 2226-2233

  Yan, Yan ^a   Chen, Jia Mei ^a   Geng, Na ^a   Lu, Tong Bu ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CO-CRYSTALS; CRYSTALLINE FORM; GLYCOLIC ACIDS; ISONICOTINAMIDE; ONE-DIMENSIONAL CHAINS; PHOSPHATE BUFFERS; SINGLE CRYSTAL X-RAY DIFFRACTION; SOLUBILITY VALUE; SYNTHONS;

DIFFERENTIAL SCANNING CALORIMETRY; HYDROGEN; MELTING POINT; STOICHIOMETRY; UREA; X RAY DIFFRACTION;

SOLUBILITY;

EID: 84860464645     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg201423q     Document Type: Article

References (40)

1. Yoshinari, Y.; Forbes, R. T.; York, P.; Kawashima, Y. Int. J. Pharm. 2002, 247, 69-77
2. Almarsson, ö.; Zaworotko, M. J. Chem. Commun. 2004, 1889-1896
3. Aakeröy, C. B.; Salmon, D. J. CrystEngComm 2005, 7, 439-448
4. Walsh, R. D. B.; Bradner, M. W.; Fleischman, S.; Morales, L. A.; Moulton, B.; Rodríguez-Hornedo, N.; Zaworotko, M. J. Chem. Commun. 2003, 186-187
5. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386-395
6. Orola, L.; Veidis, M. V.; Mutikainen, I.; Sarcevica, I. Cryst. Growth Des. 2011, 11, 4009-4016
7. Nguyen, H. L.; Horton, P. N.; Hursthouse, M. B.; Legon, A. C.; Bruce, D. W. J. Am. Chem. Soc. 2004, 126, 16-17
8. Aakeröy, C. B.; Schultheiss, N. C.; Rajbanshi, A.; Desper, J.; Moore, C. Cryst. Growth Des. 2009, 9, 432-441
9. Coates, G. W.; Dunn, A. R.; Henling, L. M.; Dougherty, D. A.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 248-251
10. Collings, J. C.; Roscoe, K. P.; Thomas, R. L.; Batsanov, A. S.; Stimson, L. M.; Howard, J. A. K.; Marder, T. B. New J. Chem. 2001, 25, 1410-1417
11. Vangala, V. R.; Nangia, A.; Lynch, V. M. Chem. Commun. 2002, 1304-1305
12. Aakeröy, C. B.; Salmon, D. J. CrystEngComm 2005, 7, 439-448
13. Musumeci, D.; Hunter, C. A.; Prohens, R.; Scuderi, S.; McCabe, J. F. Chem. Sci 2011, 2, 883-890
14. Kirchner, M. T.; Blaser, D.; Boese, R. Chem.-Eur. J. 2010, 16, 2131-2146
15. McNamara, D. P.; Childs, S. L.; Giordano, J.; Iarriccio, A.; Cassidy, J.; Shet, M. S.; Mannion, R.; ÓDonnell, E.; Park, A. Pharm. Res. 2006, 23, 1888-1897
16. Trask, A. V.; Motherwell, W.; Jones, W. Cryst. Growth Des. 2005, 5, 1013-1021
17. Aakeröy, C. B.; Forbes, S.; Desper, J. J. Am. Chem. Soc. 2009, 131, 17048-17049
18. Clarke, H. D.; Arora, K. K.; Bass, H.; Kavuru, P.; Ong, T. T.; Pujari, T.; Wojtas, L.; Zaworotko, M. J. Cryst. Growth Des. 2010, 10, 2154-2167
19. Andre, V.; Fernandes, A.; Santos, P. P.; Duarte, M. T. Cryst. Growth Des. 2011, 11, 2325-2334
20. Trask, A. V. Mol. Pharmaceutics 2007, 4, 301-309
21. Kennedy, S. H.; Rizvi, S. J. Clin. Psychopharm. 2009, 29, 157-164
22. Montejo, A. J.; Prieto, N.; Terleira, A.; Matias, J.; Alonso, S.; Paniagua, G.; Naval, S.; Parra, D. G.; Gabriel, C.; Mocaer, E.; Portoles, A. J. Psychopharmacol. 2010, 24, 111-120
23. Serfaty, M.; Osborne, D.; Buszewicz, M. J.; Blizard, R.; Raven, P. W. Int. Clin. Psychopharm. 2010, 25, 132-142
24. Zhang, P.; Shan, H. B.; Yuan, Z. D.; Jiang, X. D.; Huang, Y.; Wang, H. B.; Cao, X. F.; Cheng, X. D.; Pan, H. J.; Yu, X. CN Patent, 101481321A, 2009.
25. Yous, S.; Andrieux, J.; Howell, H. E.; Morgan, P. J.; Renard, P.; Pfeiffer, B.; Lesieur, D.; Guardiola-Lemaitre, B. J. Med. Chem. 1992, 35, 1484-1486
26. Souvie, J.-C.; Gonzalez-Blanco, I.; Thominot, G.; Chapuis, G.; Horvath, S.; Damien, G. US Patent, 7544839, 2009
27. Souvie, J.-C.; Gonzalez-Blanco, I.; Thominot, G.; Chapuis, G.; Horvath, S.; Damien, G. CN Patent, 1680284, 2005.
28. Cockrell, G.; Linol, J.; Souvie, J.-C. CN Patent, 1907959, 2006.
29. Coquerel, G.; Linol, J.; Souvie, J.-C. U.S. Patent, 20060270875, 2006.
30. Coquerel, G.; Linol, J.; Souvie, J.-C. U.S. Patent, 7358395, 2008
31. Martins, D.; Coquerel, G.; Linol, J.; Langlois, P. U.S. Patent, 2010036165, 2010.
32. Dan, H. B.; Zhang, P.; Yuan, Z. D.; Jiang, X. D.; Huang, Y.; Wang, H. B.; Cao, X. F.; Cheng, X. D.; Yu, X. CN Patent, 101585779, 2009.
33. Zheng, S. L.; Chen, J. M.; Zhang, W. X.; Lu, T. B. Cryst. Growth Des. 2011, 11, 466-471
34. http://www.drugbank.ca/drugs?type=small-molecule
35. Kye, C. H.; Sung, O. K.; Seung, W. K. Bull. Korean Chem. Soc. 1999, 20, 953-956
36. Stahl, P. H.; Wermuth, C. G. In Handbook of Pharmaceutical Salts; VHCA and Wiley-VCH: Zürich and Weinheim, 2002.
37. Dorn, T.; Fromm, M. K.; Janiak, C. Aust. J. Chem. 2006, 59, 22-25
38. Breese, K.; Fuchs, G. Eur. J. Biochem. 1998, 251, 916-923
39. http://www.cfsan.fda.gov/∼dms/opa-appa.html.
40. Sheldrick, G. M. SHELXTL-97, Program for Crystal Structure Solution and Refinement; University of Gottingen: Gottingen, Germany, 1997.