Enhancing crystalline properties of a cardiovascular active pharmaceutical ingredient using a process analytical technology based crystallization feedback control strategy

International Journal of Pharmaceutics

Volumn 430, Issue 1-2, 2012, Pages 56-64

  Saleemi, Ali N ^a   Steele, Gerry ^a   Pedge, Nicholas I ^b   Freeman, Anthony ^a   Nagy, Zoltan K ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Automated direct nucleation control; Pharmaceutical crystallization; Solvent inclusion

Indexed keywords

INAKALANT;

ARTICLE; AUTOMATED DIRECT NUCLEATION CONTROL; CHEMICAL PHENOMENA; COOLING; CRYSTALLIZATION; DRUG MANUFACTURE; DRUG STRUCTURE; FOCUSED BEAM REFLECTANCE MEASUREMENT; HEATING; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; REFLECTOMETRY; TEMPERATURE; ULTRAVIOLET SPECTROSCOPY;

2-PROPANOL; ANTI-ARRHYTHMIA AGENTS; AUTOMATION; CALIBRATION; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; DELAYED-ACTION PREPARATIONS; ETHERS; FEEDBACK; ORGANIC CHEMICALS; PARTICLE SIZE; SOLVENTS; SPECTROPHOTOMETRY, ULTRAVIOLET; TECHNOLOGY, PHARMACEUTICAL; TEMPERATURE;

EID: 84860708861     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2012.03.029     Document Type: Article

References (58)

1. E. Aamir, Z.K. Nagy, and C.D. Rielly Optimal seed recipe design for crystal size distribution control for batch cooling crystallisation processes Chem. Eng. Sci. 65 2010 3602 3614
2. E. Aamir, Z.K. Nagy, and C.D. Rielly Evaluation of the effect of seed preparation method on the product crystal size distribution for batch cooling crystallization processes Cryst. Growth Des. 10 2010 4728 4740
3. M.R. Abu Bakar, Z.K. Nagy, and C.D. Rielly Seeded batch cooling crystallization with temperature cycling for the control of size uniformity and polymorphic purity of sulfathiazole crystals Org. Process Res. Dev. 13 2009 1343 1356
4. M.R. Abu Bakar, Z.K. Nagy, A.N. Saleemi, and C.D. Rielly The impact of direct nucleation control on crystal size distribution in pharmaceutical crystallization processes Cryst. Growth Des. 9 2009 1378 1384
5. M.R. Abu Bakar, Z.K. Nagy, and C.D. Rielly Investigation of the effect of temperature cycling on surface features of sulfathiazole crystals during seeded batch cooling crystallization Cryst. Growth Des. 10 2010 3892 3900
6. M.R. Abu Bakar, Z.K. Nagy, C.D. Rielly, and S.E. Dann Investigation of the riddle of sulfathiazole polymorphism Int. J. Pharm. 414 2011 86 103
7. P. Barrett, B. Smith, J. Worlitschek, V. Bracken, B. O'Sullivan, and D. O'Grady A review of the use of process analytical technology for the understanding and optimization of production batch crystallization processes Org. Process Res. Dev. 9 2005 348 355 (Pubitemid 40814316)
8. S. Barthe, and R.W. Rousseau Utilization of focused beam reflectance measurement in the control of crystal size distribution in a batch cooled crystallizer Chem. Eng. Technol. 29 2006 206 211 (Pubitemid 43230560)
9. J. Billeter, Y. Neuhold, L. Simon, G. Puxty, and K. Hungerbühler Uncertainties and error propagation in kinetic hard-modelling of spectroscopic data Chemom. Intell. Lab. Syst. 93 2008 120 131
10. P. Billot, M. Couty, and P. Hosek Application of ATR-UV spectroscopy for monitoring the crystallisation of UV absorbing and nonabsorbing molecules Org. Process Res. Dev. 14 2010 511 523
11. A. Borissova, S. Khan, T. Mahmud, K.J. Roberts, J. Andrews, P. Dallin, Z. Chen, and J. Morris In situ measurement of solution concentration during the batch cooling crystallization of l-glutamic acid using ATR-FTIR spectroscopy coupled with chemometrics Cryst. Growth Des. 9 2009 692 706
12. R.G. Brereton Chemometrics: Data Analysis for the Laboratory and Chemical Plant 2003 John Wiley & Sons Chichester, England
13. M. Brunsteiner, A.G. Jones, F. Pratola, S.L. Price, and S.J.R. Simons Toward a molecular understanding of crystal agglomeration Cryst. Growth Des. 5 2005 3 16 (Pubitemid 40169707)
14. C. Camarasu, C. Madichie, and R. Williams Recent progress in the determination of volatile impurities in pharmaceuticals TrAC Trends Anal. Chem. 25 2006 768 777 (Pubitemid 44382677)
15. E. Deneau, and G. Steele An in-line study of oiling out and crystallization Org. Process Res. Dev. 9 2005 943 950 (Pubitemid 41784118)
16. N. Doki, H. Seki, K. Takano, H. Asatani, M. Yokota, and N. Kubota Process control of seeded batch cooling crystallization of the metastable-form glycine using an in situ ATR-FTIR spectrometer and an in situ FBRM particle counter Cryst. Growth Des. 4 2004 949 953 (Pubitemid 39248750)
17. M. Dumas, P. Carvin, and B. Biscans Characterization of liquid inclusions formed in industrial organic crystal Chem. Eng. Trans. 2 2002 713 718
18. M. Fujiwara, P.S. Chow, D.L. Ma, and R.D. Braatz Paracetamol crystallization using laser backscattering and ATR-FTIR spectroscopy: metastability, agglomeration, and control Cryst. Growth Des. 2 2002 363 370
19. R.N. Goldstein, C. Khrestian, L. Carlsson, and A.L. Waldo A new antiarrhythmic drug with predominant effects on the atria effectively terminates and prevents reinduction of atrial fibrillation and flutter in the sterile pericarditis model J. Cardiovasc. Electrophysiol. 15 2004 1444 1450 (Pubitemid 40013678)
20. A. Hagsten, C. Casper Larsen, J. Moller Sonnergaard, J. Rantanen, and L. Hovgaard Identifying sources of batch to batch variation in processability Powder Technol. 183 2008 213 219 (Pubitemid 351381728)
21. M.W. Hermanto, P.S. Chow, and R.B.H. Tan Implementation of focused beam reflectance measurement (FBRM) in antisolvent crystallization to achieve consistent product quality Cryst. Growth Des. 10 2010 3668 3674
22. E. Hishamuddin, A.G.F. Stapley, and Z.K. Nagy Application of laser backscattering for monitoring of palm oil crystallisation from melt J. Cryst. Growth 335 2011 172 180
23. K.S. Howard, Z.K. Nagy, B. Saha, A.L. Robertson, and G. Steele Combined PAT-solid state analytical approach for the detection and study of sodium benzoate hydrate Org. Process Res. Dev. 13 3 2009 590 597
24. K.S. Howard, Z.K. Nagy, B. Saha, A.L. Robertson, G. Steele, and D. Martin A process analytical technology based investigation of the polymorphic transformations during the anti-solvent crystallization of sodium benzoate from IPA/water mixture Cryst. Growth Des. 9 2009 3964 3975
25. W. Hunter, and J. Downing The peroxidation of diethyl ether and di-iso propyl ether J. Soc. Chem. Ind. 68 1949 362 364
26. C. Jia, Q. Yin, M. Zhang, J. Wang, and Z. Shen Polymorphic transformation of pravastatin sodium monitored using combined online FBRM and PVM Org. Process Res. Dev. 12 2008 1223 1228
27. Juppo, A.; Steele, G.; 2006. Preparation of crystalline N,N'-disubstituted oxabispidines and their use as cardiovascular agents. PCT Int. Appl. WO 2006/137772 A1.
28. N. Kail, W. Marquardt, and H. Briesen Process analysis by means of focused beam reflectance measurements Ind. Eng. Chem. Res. 48 2009 2936 2946
29. R.B. Keithley, R. Mark Wightman, and M.L. Heien Multivariate concentration determination using principal component regression with residual analysis TrAC Trends Anal. Chem. 28 2009 1127 1136
30. S. Kim, C. Wei, and S. Kiang Crystallization process development of an active pharmaceutical ingredient and particle engineering via the use of ultrasonics and temperature cycling Org. Process Res. Dev. 7 2003 997 1001 (Pubitemid 37543829)
31. J. Kim, J. Kim, H. Kim, and K. Koo Application of internal seeding and temperature cycling for reduction of liquid inclusion in the crystallization of RDX Org. Process Res. Dev. 15 2011 602 609
32. A. Lekhal, K.P. Girard, M.A. Brown, S. Kiang, J.G. Khinast, and B.J. Glasser The effect of agitated drying on the morphology of l-threonine (needle-like) crystals Int. J. Pharm. 270 2004 263 277 (Pubitemid 38077106)
33. R.F. Li, R. Penchev, V. Ramachandran, K.J. Roberts, X.Z. Wang, R.J. Tweedie, A. Prior, J.W. Gerritsen, and F.M. Hugen Particle shape characterisation via image analysis: from laboratory studies to in-process measurements using an in situ particle viewer system Org. Process Res. Dev. 12 2008 837 849
34. D.L. Massart, B.G.M. Vandeginste, L.M.C. Buydens, S.D. Jong, P.J. Lewi, and J. Smeyers-Verbeke Handbook of Chemometrics and Qualimetrics 1998 Elsevier Science B.V Amsterdam, The Netherlands
35. A. Mersmann Design of crystallizers Chem. Eng. Process. 23 1988 213 228
36. J.W. Mullin Crystallization fourth ed. 2001 Butterworth-Heinemann Oxford, UK
37. T. Næs, T. Isaksson, T. Fearn, and T. Davies A User-Friendly Guide to Multivariate Calibration and Classification 2002 NIR Publications Chichester, England
38. Z.K. Nagy Model based robust control approach for batch crystallization product design Comput. Chem. Eng. 33 2009 1685 1691
39. Z.K. Nagy, J.W. Chew, M. Fujiwara, and R.D. Braatz Comparative performance of concentration and temperature controlled crystallizations J. Process Contr. 18 3-4 2008 399 407 (Pubitemid 351391780)
40. Z.K. Nagy, M. Fujiwara, and R.D. Braatz Modelling and control of combined cooling and anti-solvent crystallization processes J. Process Contr. 18 2008 856 864
41. Z.K. Nagy, E. Aamir, and C.D. Rielly Internal fines removal using a population balance model based control of crystal size distribution under dissolution, growth and nucleation mechanisms Cryst. Growth Des. 11 2011 2205 2219
42. G. Nichols, S. Byard, M.J. Bloxham, J. Botterill, N.J. Dawson, A. Dennis, V. Diart, N.C. North, and J.D. Sherwood A review of the terms agglomerate and aggregate with a recommendation for nomenclature used in powder and particle characterization J. Pharm. Sci. 91 2002 2103 2109
43. H. Qu, M. Louhi-Kultanen, J. Rantanen, and J. Kallas Solvent-mediated phase transformation kinetics of an anhydrate/hydrate system Cryst. Growth Des. 6 2006 2053 2060 (Pubitemid 44450336)
44. R. Ressler Batch crystallization - a good solution to tough solids problems Pharmaceutical Engineering 17 1997 43 46
45. N. Saito, M. Yokota, T. Fujiwara, and N. Kubota A note of the purity of crystals produced in batch suspension crystallization Chem. Eng. J. 84 2001 573 575 (Pubitemid 34057341)
46. A. Saleemi, C. Rielly, and Z.K. Nagy Automated direct nucleation control for in situ dynamic fines removal in batch cooling crystallization CrystEngComm. 14 2012 2196 2203
47. A.N. Saleemi, C.D. Rielly, and Z.K. Nagy Comparative investigation of supersaturation and automated direct nucleation control of crystal size distributions using ATR-UV/Vis spectroscopy and FBRM Cryst. Growth Des. 2012 10.1021/cg201269c
48. A.N. Saleemi, C.D. Rielly, and Z.K. Nagy Monitoring of the combined cooling and antisolvent crystallization of mixtures of aminobenzoic acid isomers using ATR-UV/Vis spectroscopy and FBRM Chem. Eng. Sci. 2012 10.1016/j.ces.2012.02.005
49. L.L. Simon, and A.S. Myerson Continuous antisolvent plug-flow crystallization of a fast growing API Proceedings of the 18th International Symposium on Industrial Crystallization (ISIC 18), September 13-16 Zurich, Switzerland 2011
50. L.L. Simon, Z.K. Nagy, and K. Hungerbuhler Endoscopy-based in situ bulk video imaging of batch crystallization processes Org. Process Res. Dev. 13 2009 1254 1261
51. L.L. Simon, Z.K. Nagy, and K. Hungerbuhler Comparison of external bulk video imaging with focused beam reflectance measurement and ultra-violet visible spectroscopy for metastable zone identification in food and pharmaceutical crystallization processes Chem. Eng. Sci. 64 2009 3344 3351
52. L.L. Simon, K.A. Oucherif, Z.K. Nagy, and K. Hungerbuhler Bulk video imaging based multivariate image analysis, process control chart and acoustic signal assisted nucleation detection Chem. Eng. Sci. 65 2010 4983 4995
53. L.L. Simon, K.A. Oucherif, Z.K. Nagy, and K. Hungerbuhler Histogram matching, hypothesis testing, and statistical control-chart-assisted nucleation detection using bulk video imaging for optimal switching between nucleation and seed conditioning steps Ind. Eng. Chem. Res. 49 2010 9932 9944
54. S.J.R. Simons, F. Pratola, A. Jones, G. Brunsteiner, and M.S.L. Price Towards a fundamental understanding of the mechanics of crystal agglomeration: a microscopic and molecular approach Part. Part. Syst. Char. 21 2004 276 283
55. I.M.N. Smallwood Solvent Recovery Handbook 2002 Blackwell Science Ltd. Oxford, UK
56. N. Variankaval, A.S. Cote, and M.F. Doherty From form to function: crystallization of active pharmaceutical ingredients AIChE J. 54 2008 1682 1688 (Pubitemid 352006859)
57. 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 2004 349 369 (Pubitemid 38201430)
58. G.G.Z. Zhang, and D.J.W. Grant Formation of liquid inclusions in adipic acid crystals during recrystallization from aqueous solutions Cryst. Growth Des. 5 2005 319 324 (Pubitemid 40169758)