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Chapter 13 - Crystallization in the Pharmaceutical Industry

Published online by Cambridge University Press:  14 June 2019

By
Simon N. Black
Edited by
Allan S. Myerson ,
Deniz Erdemir  and
Alfred Y. Lee
Allan S. Myerson
Affiliation:
Massachusetts Institute of Technology
Deniz Erdemir
Affiliation:
Bristol-Myers Squibb, USA
Alfred Y. Lee
Affiliation:
Merck & Co., Inc
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Summary

Most crystallizations in the pharmaceutical industry are not carried out by crystallization scientists. The Cambridge Structure Database (CSD) contains over 850,000 crystal structures, and the number of organic molecules that have been isolated as solids is much larger. In many cases these isolations have not been repeated or scaled up. Yet this task, namely the development of robust, reproducible crystallization processes, is the main topic of this chapter. By way of introduction, meet the types of molecules, the types of people, and the nature of the industry.

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Chapter
Information
Handbook of Industrial Crystallization , pp. 380 - 413
Publisher: Cambridge University Press
Print publication year: 2019

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References

Adlington, N. K., Black, S. N., and Adshead, D. L. (2013). Organic Process Res. Dev. 17(3):557–67.Google Scholar
Atkins, P., and de Paula, J. (2002). Physical Chemistry (7th edn). Oxford: Oxford University Press, p. 178.Google Scholar
Barrett, P., and Glennon, B. (2002). Chem. Eng. Res. Des. 80(A7): 799–805.CrossRefGoogle Scholar
Bauer, J., Spanton, S., Henry, J., et al. (2001). Pharm. Res. 18(6):859–66.CrossRefGoogle Scholar
Beckmann, W. (2000). Organic Process Res. Dev. 4:372–83.CrossRefGoogle Scholar
Bernstein, J. (2002). Polymorphism in Molecular Crystals. Oxford: Clarendon Press, pp. 298–99.Google Scholar
Black, S. (2007). Proc. R. Soc. A 463:2799–811.Google Scholar
Black, S., and Muller, F. L. (2010). Organic Process Res. Dev. 14:661–65.Google Scholar
Black, S. N., Phillips, A., and Scott, C. (2009). Organic Process Res. Dev. 13(1):78–83.Google Scholar
Black, S. N., Quigley, K., and Parker, A. (2006). Organic Process Res. Dev. 10(2):241–44.Google Scholar
Black, S. N., Collier, E. A., Davey, R. J., and Roberts, R. J. (2007). J. Pharm. Sci. 96(5):1053–68.Google Scholar
Black, S. N., Cuthbert, M. W., Roberts, R. J., and Stensland, B. (2004). Crystal Growth Des. 4(3):539–44.Google Scholar
Black, S., Dang, L., Liu, C., and Wei, H. (2013). Organic Process Res. Dev. 17(3):486–92.Google Scholar
Bohlin, M., Jones, H., and Black, S. (2009). Am. Pharm. Rev., November/December:52–57.Google Scholar
Bonnett, P. E., Carpenter, K. J., Dawson, S., and Davey, R. J. (2003). Chem. Commun. 2003:698–699.Google Scholar
Brittain, H. (2009). Polymorphism in Pharmaceutical Solids (2nd edn). New York, NY: Informa Healthcare.Google Scholar
Burcham, C. L., and Jarmer, D. J. (2013). Pharm. Outsourc. 14(5), available at www.pharmoutsourcing.com/Featured-Articles/146653-Industrial-Crystallization-of-Pharmaceuticals-Capability-Requirements-to-Support-an-Outsourcing-Paradigm/.Google Scholar
Byrn, S. R., Pfeiffer, R. R., and Stowell, J. G. (1999). Solid State Chemistry of Drugs (2nd edn). West Lafayette, IN: SSCI, Inc.Google Scholar
Cardew, P. T., and Davey, R. J. (1985). Proc. R. Soc. Lond. A 398(1815):415–28.Google Scholar
Chan, L. C., Cox, B. G., and Sinclair, R. S. (2008). Organic Process Res. Dev. 12(2):213–17.Google Scholar
Chemburkar, S. J., Bauer, J., Deming, K., et al. (2000). Organic Process Res. Dev. 4:413–17.Google Scholar
Chew, J. W., Black, S. N., Chow, P. S., Tan, R. B. H., and Carpenter, K. J. (2007). Crystal Eng. Commun. 9(2):128–30.Google Scholar
Chiarella, R. A., Davey, R. J., and Peterson, M. L. (2007). Crystal Growth Des. 7(7):1223–26.Google Scholar
Clegg, I. M., Everall, N. J., King, B., Melvin, H., and Norton, C. (2001). Appl. Spectrosc. 55(9):1138–50.CrossRefGoogle Scholar
Cooke, C. L., Davey, R. J., Black, S., Muryn, C., and Pritchard, R. G. (2010). Crystal Growth Des. 10:5270–78.CrossRefGoogle Scholar
Cox, B. G. (2013). Acids and Bases: Solvent Effects on Acid-base Strength. Oxford: Oxford University Press.Google Scholar
Dang., L., Du, W., Black, S., and Wei, H. (2009). J. Chem. Eng. Data 54(11):3112–13.Google Scholar
Dang, L., Yang, H., Black, S., and Wei, H. (2009). Organic Process Res. Dev. 13:1301–06.Google Scholar
Davey, R. J., and Garside, J. (2000). From Molecules to Crystallisers: An Introduction to Crystallisation (Oxford Chemistry Primers No. 86). Oxford: Oxford University Press.Google Scholar
Davey, R. J., Black, S. N., Buckley, A. M., et al. (1994). J. Chem. Soc. Faraday Trans. 90(7):1003–9.Google Scholar
De Anda, J. C., Wang, X. Z., Lai, X., and Roberts, K. J. (2005). J. Process Control 15(7):785–97.Google Scholar
Deneau, E., and Steele, G. (2005). Organic Process Res. Dev. 9(6):943–50.Google Scholar
Docherty, R., Clydesdale, G., Roberts, K. J., and Bennema, P. (1991). J. Phys. D Appl. Phys. 24:89–99.Google Scholar
Docherty, R., Roberts, K. J., Saunders, V., Black, S., and Davey, R. J. (1993). Faraday Disc. 95:11–25.Google Scholar
Etter, M. C. (1991). Accounts Chem. Res. 23:120–26.Google Scholar
Feth, M. P., Nagel, N., Baumgartner, B., et al. (2011). Eur. J. Pharm. Sci. 42:116–29.Google Scholar
Foltz, M. F., Coon, C. L., Garcia, F., and Nichols, A. L. (1994). Propell. Explos. Pyrotech. 19(3):33–44.Google Scholar
Getsoain, A., Lodaya, R. M., and Blackburn, A. C. (2008). Int. J. Pharm. 348:3–9.Google Scholar
Gu, C.-H., Young, V., Jr., and Grant, D. J. W. (2001). J. Pharm. Sci. 90(11):1878–89.Google Scholar
Gu, C.-H., Chaterjee, K., Young, V., Jr., and Grant, D. J. W. (2002). J. Crystal Growth 235:471–81.Google Scholar
He, G., Jacob, C., Guo, L., Chow, P. S., and Tan, R. B. H. (2008). J. Phys. Chem. B 112(32):9890–95.Google Scholar
Hilfiker, R. (2006). Polymorphism in the Pharmaceutical Indsutry. Weinheim: Wiley-VCH.Google Scholar
Hu, Y., Liang, J. K., Myerson, A. S., and Taylor, L. S. (2005). Ind. Eng. Chem. Res. 44:1233–40.Google Scholar
Iacocca, R. G., Burcham, C. L., and Hilden, L. R. (2010). J. Pharm. Sci. 99(1):51–75.Google Scholar
International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use (ICH) (2011). Impurities: Guideline for Residual Solvents (Q3C[R5]), available at www.ich.org.Google Scholar
International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use (ICH) (1999). Specifications: Test Procedures and Acceptance Criteria for New Drug Substances and New Drug Products: Chemical Substances (Q6A), available at www.ich.org.Google Scholar
Jacques, J., Collet, A., and Wilen, S. H. (1994). Enantiomers, Racemates and Resolutions. Malabar, FL: Krieger.Google Scholar
Jarring, K., Larsson, T., Stensland, B., and Ymén, I. (2006). J. Pharm. Sci. 95(5):1144–61.CrossRefGoogle Scholar
Katta, J., and Rasmuson, A. C. (2007). Int. J. Pharm. 348:61–69.Google Scholar
Kiesow, K., Tumakaka, F., and Sadowski, G. (2008). J. Crystal Growth 310(18):4163–68.Google Scholar
Kim, S., Wei, C., and Kaing, S. (2003). Organic Process Res. Dev. 7:997–1001.Google Scholar
Kim, S., Lotz, B., Lindrud, M., et al. (2005). Organic Process Res. Dev. 9:894–901.CrossRefGoogle Scholar
Klussmann, M., White, A. J. P., Armstrong, A., and Blackmond, D. G. (2006). Angewandte Chem. Int. Ed. 45:7985–89.Google Scholar
Kobayashi, R., Fujimaki, Y., Ukita, T., and Hiayama, Y. (2006). Organic Process Res. Dev. 10(6):1219–26.CrossRefGoogle Scholar
Lee, I., Variankaval, N., Lindemannn, C., and Starbuck, C. (2004). Am. Pharm. Rev. 7(5):120–28.Google Scholar
Leonard, J., Lygo, B., and Procter, G. (2013). Advanced Practical Organic Chemistry (3rd. edn). Boca Raton, FL: CRC Press, p. 210.Google Scholar
Li, Y., Chow, P. S., Tan, R. B. H., and Black, S. N. (2008). Organic Process Res. Dev. 12(2):264–70.Google Scholar
Liotta, V., and Sabesan, V. (2004). Organic Process Res. Dev. 8:488–94.Google Scholar
Lorenz, H., Sheehan, P., and Seidel-Morgenstern, A. (2001). J. Chromatogr. A 908:201–14.Google Scholar
Masui, Y., Kitaura, Y., Kobayashi, T., et al. (2003). Organic Process Res. Dev. 7(3):334–38.Google Scholar
McBride, M., and Tully, J. C. (2008). Nature 452:161–62.Google Scholar
McCabe, J. F. (2010). Crystal Eng. Commun. 12:1110–19.Google Scholar
McKie, D., and McKie, C. (1992). Essentials of Crystallography. Oxford: Blackwell Scientific.Google Scholar
McNamara, D. P., Childs, S. L., Giordano, J., et al. (2006). Pharm. Res. 23(8):1888–97.Google Scholar
Muller, F. L. (2009). Chem. Eng. Res. Des. 87(4):627–32.Google Scholar
Muller, F. L., Fielding, M., and Black, S. N. (2009). Organic Process Res. Dev. 13:1315–21.Google Scholar
Mullin, J. W, (2001). Crystallization (4th edn). Oxford: Butterworth-Heinemann, p. 355.Google Scholar
Nehm, S. J., Rodriguez-Spong, B., and Rodriguez-Hornedo, N. (2006). Crystal Growth Des. 6:592–600.Google Scholar
O’Sullivan, B., Barrett, P., Hsiao, G., Carr, A., and Glennon, B. (2003). Organic Process Res. Dev. 7:977–82.Google Scholar
Parsons, A. R., Black, S. N., and Colling, R. (2003). Trans. Inst. Chem. Eng. 81:700–4.Google Scholar
Poornachary, S. K., Lau, G., Chow, P. S., Tan, R. B. H., and George, N. (2011). Crystal Growth Des. 11(2):492–500.Google Scholar
Pudipeddi, M., and Serajuddin, A. T. M. (2005). J. Pharm. Sci. 94(5):929–39.CrossRefGoogle Scholar
Reichardt, C. (2004). Solvents and Solvent Effects in Organic Chemistry (3rd. edn). Meinheim: Wiley-VCH.Google Scholar
Remenar, J. F., Morisette, S. L., Peterson, M. L., et al. (2003). J. Am. Chem. Soc. 125:8456–57.Google Scholar
Reutzel-Edens, S. M., Bush, J. K., Magee, P. A., Mcphenson, G. A., and Byrn, S. R. (2003). Crystal Growth Des. 3(6):897–907.CrossRefGoogle Scholar
Ricci, J. E. (1966). The Phase Rule and Heterogeneous Equilibrium. New York, NY: Dover.Google Scholar
Rived, F., Roses, M., and Bosch, E. (1998). Anal. Chim. Acta 374:309–24.Google Scholar
Sathyamoorty, S., Moggridge, G. D., and Hounslow, M. J. (2004). AIChE J. 47(9):2012–24.Google Scholar
Scott, C., and Black, S. (2005). Organic Process Res. Dev. 9:890–93.Google Scholar
Stahl, P. H., and Wermuth, C. G., eds. (2002). Handbook of Pharmaceutical Salts: Properties, Selection and Use. Weinheim: Wiley-VCH.Google Scholar
Starbuck, C., Spartalis, A., Wai, L., et al. (2002). Crystal Growth Des. 2(6):315–522.Google Scholar
Steele, G., Morgan, M., Huang, Z., et al. (2010). In AIChE Annual Meeting Conference Proceedings (Paper 88g), Salt Lake City, UT, available at www.worldcat.org/title/2010-aiche-annual-meeting-conference-proceedings-salt-palace-convention-center-salt-lake-city-ut-november-7-12-2010/oclc/837880418?referer=di&ht=edition.Google Scholar
Svard, M., Nordström, F. L., Jasnobulk, T., and Rasmuson, A. C. (2010). Crystal Growth Des. 10:195–204.Google Scholar
Tennant, S. (1797). Philos. Trans. R. Soc. Lond. 87:123–27.Google Scholar
Towler, C. S., Davey, R. J., Lancaster, R. W., and Price, C. J. (2004). J. Am. Chem. Soc. 126:13347–53.Google Scholar
Viedma, C. (2005). Phys. Rev. Lett. 94:065504.Google Scholar
Wang, Y., LoBrutto, R., Wenslow, R. W., and Santos, I. (2005). Organic Process Res. Dev. 9:670–76.Google Scholar
Wood, W. M. L. (2001). Powder Technol. 121(1):53–59.Google Scholar
Yu., L. (1995). J. Pharm. Sci. 84(8):966–74.Google Scholar
Yu, Q., Black, S., and Wei, H (2009). J. Chem. Eng. Data 54(7):2123–25.Google Scholar
Yu, Z. Q., Chow, P. S., and Tan, R. B. H. (2006). Organic Process Res. Dev. 10(4):717–22.Google Scholar
Yu, Z. Q., Chew, J. W., Chow, P. S., and Tan, R. B. H. (2007). Chem. Eng. Res. Des. 85(A7):893–905.Google Scholar
Zhu, H., and Grant, D. J. W. (1996). Int. J. Pharm. 135:151–60.Google Scholar
Zhu, H., Yuen, C., and Grant, D. J. W. (1996). Int. J. Pharm. 139:33–43.Google Scholar

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