Open Access

Fast real-time monitoring of entacapone crystallization and characterization of polymorphs via Raman spectroscopy, statistics and SWAXS

1. R. Hilfiker, F. Blatter and M. von Raumer, Relevance of Solid-state Properties for Pharmaceutical Products, in Polymorphism in the Pharmaceutical Industry (Ed. R. Hilfiker), 1st ed., John Wiley & Sons Inc., Weinheim 2006, pp. 1-19.10.1002/3527607889.ch1Search in Google Scholar

2. W. P. Findlay and D. E. Bugay, Utilization of Fourier transform-Raman spectroscopy for the study of pharmaceutical crystal forms, J. Pharm. Biomed. Anal. 16 (1998) 921-930; DOI: 10.1016/ S0731-7085(97)00058-7.10.1016/S0731-7085(97)00058-7Search in Google Scholar

3. B. Yu. Shekunov and P. York, Crystallization processes in pharmaceutical technology and drug delivery design, J. Cryst. Growth 211 (2000) 122-136; DOI: 10.1016/S0022-0248(99)00819-2.10.1016/S0022-0248(99)00819-2Search in Google Scholar

4. M. C. Gamberini, C. Baraldi, A. Tinti, C. Rustichelli, V. Ferioli and G. Gamberini, Solid state characterization of chloramphenicol palmitate. Raman spectroscopy applied to pharmaceutical polymorphs, J. Mol. Str. 785 (2006) 216-224; DOI: 10.1016/j.molstruc.2005.10.012.10.1016/j.molstruc.2005.10.012Search in Google Scholar

5. W. Beckmann, Seeding the desired polymorph: background, possibilities, limitations and case studies, Org. Process Res. Dev. 4 (2000) 372-383; DOI: 10.1021/op0000778.10.1021/op0000778Search in Google Scholar

6. P. Novak, A. Ki{i}, T. Hrenar, T. Jedna~ak, S. Miljani} and G. Verbanec, In-line reaction monitoring of entacapone synthesis by Raman spectroscopy and multivariate analysis, J. Pharm. Biomed. Anal. 54 (2011) 660-666; DOI: 10.1016/j.jpba.2010.10.012.10.1016/j.jpba.2010.10.01221087836Search in Google Scholar

7. T. De Beer, A. Burggraeve, M. Fonteyne, L. Saerens, J. P. Remon and C. Vervaet, Near infrared and Raman spectroscopy for the in-process monitoring of pharmaceutical production processes, Int. J. Pharm. 417 (2011) 32-47; DOI: 10.1016/j.ijpharm.2010.12.012.10.1016/j.ijpharm.2010.12.01221167266Search in Google Scholar

8. H. Wikström, P. J. Marsac and L. S. Taylor, In-line monitoring of hydrate formation during wet granulation using Raman spectroscopy, J. Pharm. Sci. 94 (2004) 209-219; DOI: 10.1002/jps.20241.10.1002/jps.2024115761944Search in Google Scholar

9. Šašić, A. S. Palm and D. Tang, Monitoring the dissolution of active pharmaceutical ingredient and TGPS in real time via IR spectroscopy during the manufacturing of liquid dosage formulation, J. Pharm. Biomed. Anal. 70 (2012) 273-279; DOI: 10.1016/j.jpba.2012.07.010.10.1016/j.jpba.2012.07.01022871426Search in Google Scholar

10. G. Févotte, In situ Raman spectroscopy for in-line control of pharmaceutical crystallization and solids elaboration processes: A review, Chem. Eng. Res. Des. 85 (A7) (2007) 906-920; DOI: 10.1205/ cherd06229.10.1205/cherd06229Search in Google Scholar

11. L. X. Yu, R. A. Lionberger, A. S. Raw, R. D’Costa, H. Wu and A. S. Hussain, Applications of process analytical technology to crystallization processes, Adv. Drug Deliv. Rev. 56 (2003) 349-369; DOI: 10.1016/j.addr.2003.10.012.10.1016/j.addr.2003.10.012Search in Google Scholar

12. J.Aaltonen, K. C. Gordon, C. J. Strachan and T. Rades, Perspectives in the use of spectroscopy to characterise pharmaceutical solids, Int. J. Pharm. 364 (2008) 159-169; DOI: 10.1016/j.ijpharm. 2008.04.043.Search in Google Scholar

13. C. Starbuck, A. Spartalis, L. Wai, J. Wang, P. Fernandez, C. M. Lindemann, G. X. Zhou and Z. Ge, Process optimization of a complex pharmaceutical polymorphic system via in situ Raman spectroscopy, Cryst. Growth Des. 2 (2002) 515-522; DOI: 10.1021/cg025559k.10.1021/cg025559kSearch in Google Scholar

14. T. Ono, J. H. ter Horst and J. Jansens, Quantitative measurement of the polymorphic transformation of L-glutamic acid using in-situ Raman spectroscopy, Cryst. Growth Des. 4 (2004) 465-469; DOI: 10.1021/cg0342516.10.1021/cg0342516Search in Google Scholar

15. C. J. Strachan, T. Rades, K. C. Gordon and J. Rantanen, Raman spectroscopy for quantitative analysis of pharmaceutical solids, J. Pharm. Pharmacol. 59 (2010) 179-192; DOI: 10.1211/jpp.59. 2.0005.Search in Google Scholar

16. E. Kriesten, D. Mayer, F. Alsmeyer, C. B. Minnich, L. Greiner and W. Marquardt, Identification of unknown pure component spectra by indirect hard modeling, Chemom. Intell. Lab. Syst. 93 (2008) 108-119; DOI: 10.1016/j.chemolab.2008.05.002.10.1016/j.chemolab.2008.05.002Search in Google Scholar

17. J. Li and L. Dai, A hard modeling approach to determine methanol concentration in methanol gasoline by Raman spectroscopy, Sens. Actuat. B 173 (2012) 385-390; DOI: 10.1016/j.snb.2012. 07.012.Search in Google Scholar

18. N. Chieng, T. Rades and J. Aaltonen, An overview of recent studies on the analysis of pharmaceutical polymorphs, J. Pharm. Biomed. Anal. 55 (2011) 618-644; DOI: 10.1016/j.jpba.2010.12.020.10.1016/j.jpba.2010.12.020Search in Google Scholar

19. K. Kogermann, J. Aaltonen, C. J. Strachan, K. Pöllänen, P. Veski, J. Heinämäki, J. Yliruusi and J. Rantanen, Qualitative in situ analysis of multiple solid-state forms using spectroscopy and partial least squares discriminant modeling, J. Pharm. Sci. 96 (2007) 1802-1820; DOI: 10.1002/jps. 20840.Search in Google Scholar

20. A. Hodzic, M. Llusa, S. D. Fraser, O. Scheibelhofer, D. M. Koller, F. Reiter, P. Laggner and J. G. Khinast, Small and wide-angle X-ray scattering (SWAXS) for quantification of aspirin content in a binary powder mixture, Int. J. Pharm. 428 (2012) 91-95; DOI: 10.1016/j.ijpharm.2012.02.048.10.1016/j.ijpharm.2012.02.048Search in Google Scholar

21. A. Hodzic, M. Llusa, N. Heigl,W. Tritthart, S. D. Fraser, P. Laggner and J. G. Khinast, Effect of process variables on the small and wide angle X-ray scattering (SWAXS) patterns of powders, granules and pharmaceutical tablets, Powder Technol. 221 (2012) 447-452; DOI: 10.1016/j.powtec. 2012.01.043.Search in Google Scholar

22. A. Hodzic, P. Zoumpoulakis, G. Pabst, T. Mavromoustakos and M. Rappolt, Losartan’s affinity to fluid bilayers modulates lipid-cholesterol interactions, Phys. Chem. Chem. Phys. 14 (2012) 4780-4788; DOI: 10.1039/c2cp40134g.10.1039/c2cp40134gSearch in Google Scholar

23. M. Köberl, H. J. Hinz and G. Rapp, Temperature scanning simultaneous small- and wide- X-ray scattering studies on glycolipid vesicles: areas, expansion coefficients and hydration, Chem. Phys. Lipids 91 (1998) 13-37; DOI: 10.1016/S0009-3084(97)00091-1.10.1016/S0009-3084(97)00091-1Search in Google Scholar

24. P. T. Männisto and S. Kaakkola, Catechol-O-metyltransferase (COMT) biochemistry, molecular biology, pharmacology, and clinical efficiacy of the new selective COMT inhibitors, Pharmacol. Rev. 51 (1999) 593-628. Search in Google Scholar

25. J. Leppänen, E. Wegelius, T. Nevalainen, T. Järvinen, J. Gynther and J. Huuskonen, Structural studies of acyl esters of entacapone, J. Mol. Struct. 562 (2001) 129-135; DOI: 10.1016/S0022-2860 (00)00859-0.Search in Google Scholar

26. M. S. M. Jaweed, R. A. R. Khan, R. P. Yadav and Z. G. Shaikh, Stable Polymorphs of (E)-N,Ndiethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide, U.S. Pat. WO 2005/066117 A1, 21 Jul 2005.Search in Google Scholar

27. S. Mantegazza, P. Allegrini and G. Razzetti, A Process for the Preparation of Entacapone, Eur. Pat. WO 2007/135406 A1, 4 Dec. 2007.Search in Google Scholar

28. A. Kwokal, T. T. H. Nguyen and K. J. Roberts, Polymorph-directing seeding of entacapone crystallization in aqueous/acetone solution using a self-assembled molecular layer on Au (100), Cryst. Growth Des. 9 (2009) 4324-4334; DOI: 10.1021/cg900105u.10.1021/cg900105uSearch in Google Scholar

29. O. Glatter and O. Kratky, Small Angle X-ray Scattering, Academic Press, London 1982.Search in Google Scholar

30. M. Ratkaj, T. Biljan and S. Miljani}, Quantitative analysis of entacapone isomers using surface- -enhanced Raman spectroscopy and partial least squares regression, Appl. Spectrosc. 66 (2012) 1468-1474; DOI: 10.1366/12-06752. 10.1366/12-0675223231910Search in Google Scholar

eISSN:
1846-9558
ISSN:
1330-0075
Language:
English
Publication timeframe:
4 times per year
Journal Subjects:
Pharmacy, other