Cocrystal production method reducing deposition risk of undesired single component crystals in anti-solvent cocrystallization

Momoko Nishimaru; Shoji Kudo; Hiroshi Takiyama

Journal of Industrial and Engineering Chemistry, Vol.36, 40-43, April, 2016

DOI10.1016/j.jiec.2016.01.027 Export Citation

Cocrystal production method reducing deposition risk of undesired single component crystals in anti-solvent cocrystallization

Momoko Nishimaru^†, Shoji Kudo, and Hiroshi Takiyama

Department of Chemical Engineering,, Tokyo University of Agriculture and Technology (TUAT), 24-16, Nakacho-2, Koganei, Tokyo 184-8588, Japan

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The cocrystallization operation has the deposition risk of undesired crystals. In this study, the strategy of cocrystal production method considering the risk reduction of undesired single component crystal deposition was investigated. The anti-solvent cocrystallization was carried out in four-component system of carbamazepine (CBZ), saccharin (SAC), methanol and water. The undesired single component crystals precipitated depending on the solution addition sequences. Considering the driving force for each component, a domain without the deposition risk of the undesired crystals was determined on the phase diagram. It is important to keep the operation point in this domain for production of desired cocrystals.

Keywords:Cocrystal;Cocrystallization;Anti-solvent crystallization;Phase diagram;CBZ-SAC (1:1)

[References]

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[1] Aitipamula S, et al., Cryst. Growth Des., 12, 2147 (2012)

[2] Shiraki K, Takata N, Takano R, Hayashi Y, Terada K, Pharm. Res., 25, 2581 (2008)

[3] Good DJ, Rodrıguez-Hornedo N, Cryst. Growth Des., 9, 2252 (2009)

[4] ter Horst JH, Cains PW, Cryst. Growth Des., 8, 2537 (2008)

[5] Gagniere E, Mangin D, Puel F, Rivoire A, Monnier O, Garcia E, Klein JR, J. Cryst. Growth, 311(9), 2689 (2009)

[6] Lee KC, Kim KJ, Chem. Eng. Technol., 34(4), 619 (2011)

[7] Childs SL, Hornedo NR, Reddy LS, Jayasankar A, Maheshwari C, McCausland L, Shipplett R, Stahly BC, Cryst. Eng. Comm., 10, 856 (2008)

[8] Chun NH, Wang IC, Lee MJ, Jung YT, Lee S, Kim WS, Choi GJ, Eur. J. Pharm. Biopharm., 85, 854 (2013)

[9] Neurohr C, Marchivie M, Lecomte S, Cartigny Y, Couvrat N, Sanselme M, Subra-Paternault P, Cryst. Growth Des., 15, 4616 (2015)

[10] Kudo S, Takiyama H, J. Cryst. Growth, 392, 87 (2014)

[11] Wang IC, Lee MJ, Sim SJ, Kim WS, Chun NH, Choi GJ, Int. J. Pharm., 450, 311 (2013)

[12] Coquerel G, Chem. Soc. Rev., 43, 2286 (2014)

[13] Fleischman SG, Kuduva SS, McMahon JA, Moulton B, Walsh RDB, Rodrı-guez-Hornedo N, Zaworotko MJ, Cryst. Growth Des., 3, 909 (2003)

[14] Harris RK, Ghi PY, Puschmann H, Apperley DC, Griesser UJ, Hammond RB, Ma C, Roberts KJ, Pearce GJ, Yates JR, Pickar CJ, Org. Process Res. Dev., 9, 902 (2005)

[15] Bart JCJ, J. Chem. Soc. B.(4), 376 (1968)

[16] Coquerel G, J. Pharm. Pharmacol., 67, 869 (2015)

[17] Tian F, Zeitler JA, Strachan CJ, Saville DJ, Gordon KC, Rades T, J. Pharm. Biomed. Anal., 40, 271 (2006)