Abstract
Mechanical treatment with addition of some liquid, crystallization from solutions, and heating of the mixture components preliminary subjected to mechanical treatment were the methods used for the preparation of the co-crystals of 4-hydroxy-2-methyl-N-(5-methylthiazol-2-yl)-2H-1,2-benzothiazin-3-carboxamide 1,1-dioxide (meloxicam) with carboxylic acids. It was shown that preliminary mechanical treatment plays significant role for the synthesis, whereas the addition of small amounts of solvents accelerates the process. The co-crystals were obtained for 17 mixtures of meloxicam—carboxylic acid. The use of the co-crystals of meloxicam in the compositions of improved pharmaceutical forms was found promising, which was attributable to the fact that the dissolution rate and the solubility of the co-crystals of meloxicam with the carboxylic acids under study are higher than those for meloxicam itself.
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K. Fucke, T. Shakhtshneider, S. Myz, N. Tumanov, E. Boldyreva, U. Griesser, New J. Chem., 2012, 36, 1969.
A. V. Trask, Mol. Pharm., 2007, 4, 301.
R. P. Rastogi, N. B. Singh, R. P. Singh, J. Solid State Chem., 1977, 20, 191.
T. P. Shakhtshneider, V. V. Boldyrev, in Reactivity of Molecular Solids, Eds E. Boldyreva, V. Boldyrev, John Wiley and Sons, Chichester, 1999, p. 271.
A. V. Trask, W. D. S. Motherwell, W. Jones, Chem. Commun., 2004, 890.
W. Jones, W. D. S. Motherwell, A. V. Trask, MRS Bull., 2006, 31, 875.
P. Vishweshwar, J. A. McMahon, J. A. Bis, M. J. Zaworotko, J. Pharm. Sci., 2006, 95, 499.
B. Rodriguez, A. Bruckmann, T. Rantanen, C. Bolm, Adv. Synth. Catal., 2007, 349, 2213.
R. Kuroda, T. Sato, Y. Imai, CrystEngComm, 2008, 10, 1881.
A. Bruckmann, A. Krebs, C. Bolm, Green Chem., 2008, 10, 1131.
T. Fri ic’, W. Jones, Cryst. Growth Des., 2009, 9, 1621.
W. C. Shearouse, D. C. Waddell, J. Mack, Curr. Opin. Drug Discovery and Development, 2009, 12, 772.
M. Senna, S. Nakayama, J. Alloys Comp., 2009, 483, 265.
R. Kuroda, J. Yoshida, A. Nakamura, S.-I. Nishikiori, Cryst-EngComm, 2009, 11, 427.
C. Avendaco, A. Briceco, CrystEngComm, 2009, 11, 408.
T. Fri ic’, W. Jones, Ann. Chim. — Sci. Mat., 2009, 34, 415.
W. Yuan, T. Fri ic’, D. Apperley, S. L. James, Angew. Chem., Int. Ed., 2010, 49, 3916.
W. Yuan, J. O’Connor, S. L. James, CrystEngComm, 2010, 12, 3515.
S. Marivel, D. Braga, F. Grepioni, G. I. Lampronti, Cryst-EngComm, 2010, 12, 2107.
A. Baron, J. Martinez, F. Lamaty, Tetrahedron Lett., 2010, 51, 6246.
O. I. Lomovskii, V. V. Boldyrev, Mekhanokhimiya v reshenii ekologicheskikh zadach [Mechanochemistry in Solving of En-vironmental Problems], GPNTB, Novosibirsk, 2006, 220 pp. (in Russian).
A. V. Trask, W. Jones, Top Curr. Chem., 2005, 254, 41.
V. V. Boldyrev, E. V. Boldyreva, in Experimental and Theoretical Studies in Modern Mechanochemistry, Eds F. Delogu, G. Mulas, Transworld Research Network, Kerala, 2010, p. 21.
N. Shan, F. Toda, W. Jones, Chem. Commun., 2002, 2372.
A. V. Trask, W. D. S. Motherwell, W. Jones, Chem. Commun., 2004, 890.
V. V. Boldyrev, A. Kh. Khabibullin, N. V. Kosova, E. G. Avvakumov, Inorg. Mater., 1997, 33, 1144.
J. Temuujin, K. Okada, K. J. D. MacKenzie, J. Solid State Chem., 1998, 138, 169.
V. V. Boldyrev, Powder Technol., 2002, 122, 247.
D. Braga, S. L. Giaffreda, F. Grepioni, M. R. Chierotti, R. Gobetto, G. Palladino, M. Polito, CrystEngComm., 2007, 9, 879.
A. Jayasankar, D. J. Good, N. Rodriguez-Hornedo, Mol. Pharm., 2007, 4, 360.
E. V. Boldyreva, in Frontiers in Mechanochemsitry and Mechanical Alloying, Eds R. Kumar, S. Srikanth, S. P. Mehrotra, National Metallurgical Laboratory, Jamshedpur, 2011, 17.
P. Luger, K. Daneck, W. Engel, G. Trummlitz, K. Wagner, Eur. J. Pharm. Sci., 1996, 4, 175.
S. A. Myz, T. P. Shakhtshneider, K. Fucke, A. P. Fedotov, E. V. Boldyreva, V. V. Boldyrev, N. I. Kuleshova, Mendeleev Commun., 2009, 19, 272.
S. A. Myz, T. P. Shakhtshneider, N. A. Tumanov, E. V. Boldyreva, Materialy Vseross. nauch. molodezh. shkoly-konf. Khimiya pod znakom SIGMA: issledovaniya, innovatsii, tekhnologii [Abstr. All-Russian Scientific Youth School-Conf. “Chemistry under the “SIGMA” sign: Investigations, Innovations, Technologies”] (Omsk, May 16–24, 2010), Novosibirsk, 2010, p. 209 (in Russian).
S. A. Myz, T. P. Shakhtshneider, N. A. Tumanov, E. V. Boldyreva, Abstr. Twelfth Annual Conf. YUCOMAT 2010 (Herceg Novi, Montenegro, September 6–10, 2010), Belgrade, 2010, 83.
M. L. Cheney, D. R. Weyna, N. Shan, M. Hanna, L. Wojtas, M. J. Zaworotko, Cryst. Growth Des., 2010, 10, 4401.
S. A. Myz, T. P. Shakhtshneider, N. A. Tumanov, E. V. Boldyreva, Mater. X mezhdunar. nauch. konf. Khimiya tverdogo tela: nanomaterialy, nanotekhnologii [Abstr. X Intern. Sci. Conf. “Chemistry of Solid State: Nanomaterials, Nanotechnologies”] (Stavropol’, October 17–22, 2010), Stavropol’, 2010, 351 (in Russian).
N. A. Tumanov, S. A. Myz, T. P. Shakhtshneider, E. V. Boldyreva, CrystEngComm, 2012, 14, 305.
S. A. Myz, T. P. Shakhtshneider, N. A. Tumanov, E. V. Boldyreva, Tez. dokl. Mezhdunar. nauch.-tekh. konf. Nanotekhnologii funktsional’nykh materialov [Abstr. Intern. Sci.-Tech. Conf. “Nanotechnologies of Functional Materials”] (St.-Petersburg, September 22–24, 2010), St.-Petersburg, 2010, 116 (in Russian).
A. Alhalaweh, S. George, D. Boström, S. P. Velaga, Cryst. Growth Des., 2010, 10, 4847.
Pr Sathesh Babu, C. V. S. Subrahmanyam, J. Thimmasetty, R. Manavalan, K. Valliappan, Pak. J. Pharm. Sci., 2007, 20, 311.
N. A. Tumanov, E. V. Boldyreva, N. E. Shikina, Acta Crystallogr., 2010, C66, 279.
I. A. Tumanov, A. F. Achkasov, E. V. Boldyreva, V. V. Boldyrev, CrystEngComm, 2011, 13, 2213.
Gosudarstvennaya farmakopeya Rossiiskoi Federatsii [State Pharmacopoeia of the Russian Federation], Nauchnyi tsentr ekspertizy sredstv meditsinskogo primeneniya [Scientific Center of Expertise of Medicinal Agents], Moscow, 2008, 704 pp. (in Russian).
S. Defazio, R. Cini, Polyhedron, 2003, 22, 1355.
S. L. Childs, K. Hardcastle, Cryst. Growth Des., 2007, 7, 1291.
Stoe & Cie, WinXPOW, Stoe & Cie GmbH, Darmstadt (Germany), 2002.
G. M. Sheldrick, Acta Crystallogr., Sect. A, 2008, 64, 112.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1782–1793, September, 2012.
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Myz, S.A., Shakhtshneider, T.P., Tumanov, N.A. et al. Preparation and studies of the co-crystals of meloxicam with carboxylic acids. Russ Chem Bull 61, 1798–1809 (2012). https://doi.org/10.1007/s11172-012-0248-6
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DOI: https://doi.org/10.1007/s11172-012-0248-6