Crystallization from solutions containing multiple conformers: A new modeling approach for solubility and supersaturation

Chemical Engineering Science

Volumn 66, Issue 1, 2011, Pages 88-102

  Derdour, L ^a   Pack, S K ^a   Skliar, D ^a   Lai, C J ^a   Kiang, S ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

Conformation; Heating crystallization; Intrinsic solubility; Pharmaceuticals; Retrograde solubility; Total solubility

Indexed keywords

AB INITIO CALCULATIONS; CRYSTAL GROWTH INHIBITION; CRYSTAL SURFACES; CRYSTALLIZATION BEHAVIOR; CRYSTALLIZATION PARAMETER; DRIVING FORCES; ENERGY DIFFERENCES; HEATING RAMPS; HIGH ENERGY; HIGH TEMPERATURE; HIGH-ENERGY BARRIERS; INTRINSIC SOLUBILITIES; LOW LEVEL; MODELING APPROACH; MULTIPLE CONFORMATIONS; NMR DATA; ORGANIC MOLECULES; ORGANIC SUBSTANCES; PHARMACEUTICALS; POWDER PROPERTIES; RETROGRADE SOLUBILITY; ROTOMERS; TOTAL SOLUBILITY;

COALESCENCE; CONFORMATIONS; CRYSTAL GROWTH; CRYSTALLIZATION; ENERGY BARRIERS; HEATING; HIGH ENERGY PHYSICS; SEMICONDUCTING GALLIUM COMPOUNDS; SUPERSATURATION; TUNGSTEN CARBIDE;

SOLUBILITY;

EID: 78149468554     PISSN: 00092509     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ces.2010.10.023     Document Type: Article

References (54)

1. Abu Bakar M.R., Zoltan K.N., Rielly C.D. Investigation of the effect of temperature cycling on surface features of sulfathiazole crystals during seeded batch cooling crystallization. Crys. Growth Des. 2010, 10(9):3892-3900.
2. Aladko L.S., Komarov V.Y., Manakov A.Y., Ancharov L.I. Phase diagram of the hexamethylenetetramine:water system. J. Incl. Phenom. Macrocycl. Chem. 2007, 59:389-391.
3. Borissova A., Khan S., Mahmud T., Roberts K.J., Andrews J., Dallin P., Chen Z.P., Morris J. 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. 2009, 9(2):692-706.
4. Black, S.N., Jones, H., 2008. Seed cool & monitor. In: Proceedings of the 17th International Symposium on Industrial Crystallization, vol. 1, pp. 11-18.
5. Bennema P., Van Eupen J., Van Der Wolf B.M.A., Los J.H., Meekes H. Solubility of molecular crystals: polymorphism in the light of solubility theory. Int. J. Pharm. 2008, 351:74-91.
6. Byrn S.R., Weir Graber C., Midland S.L. Comparison of the solid and solution conformations of methapyriline, tripelennamine, diphenhydramine, histamine and choline. The infrared-X-ray method for determination of solution conformation. J. Org. Chem. 1976, 41(13):2283-2288.
7. Byrn S.R., McKenzie A.T., Hassan M.M., Al-Badr A.A. Conformation of glyburide in the solid state and in solution. J. Pharm. Sci. 1986, 75(6):596-600.
8. Bernstein J., Hagler A.T. Conformational polymorphism. The influence of crystal structure on molecular conformation. J. Am. Chem. Soc. 1978, 100(3):673-681.
9. Black S.N., Collier E.A., Davey R.J., Roberts R.J. Structure, solubility, screening and synthesis of molecular salts. J. Pharm. Sci. 2007, 96(5):1053-1068.
10. Bakar M.R.A., Nagy Z.K., Rielly C.D. Seeded batch cooling crystallization with temperature cycling for the control of size uniformity and polymorphic purity of sulfathiazole crystals. Org. Proc. Res. Dev. 2009, 13(6):1343-1356.
11. Becke A.D. A new mixing of Hartree-Fock and local density-functional theories. J. Chem. Phys. 1993, 98:1372-1377.
12. Chang R. Physical Chemistry for the Chemical and the Biological Sciences 2000, University Science Books, Sausalito, CA, 1018 pp. third ed.
13. Carless J.E., Foster A.A. Accelerated crystal growth of sulphathiazole by temperature cycling. J. Pharm. Pharmacol. 1966, 18:697-708.
14. Davey R.J. The effect of impurities on the kinetics of crystal growth from solution. J. Cryst. Growth 1976, 34(1):109-119.
15. Dittert L.W., Higuchi T., Reese D.R. Phase solubility technique in studying the formation of complex salts of triamterene. J. Pharm. Sci. 1964, 53(11):1325-1328.
16. Eggers J., Kempkes M., Cornel J., Mazzotti M., Koschinski I., Verdurand E. Monitoring size and shape during cooling crystallization of ascorbic acid. Chem. Eng. Sci. 2009, 64(1):163-171.
17. Eckhardt C.J., Bernstein J. Molecular conformation and electronic structure. The solid state spectrum of a planar anil. J. Am. Chem. Soc. 1972, 94(9):3247-3249.
18. Francl M.M., Petro W.J., Hehre W.J., Binkley J.S., Gordon M.S., DeFrees D.J., Pople J.A. Self-consistent molecular orbital methods. XXIII. A polarization-type basis set for second-row elements. J. Chem. Phys. 1982, 77:3654.
19. Garside J., Mersmann A., Nyvlt J. Measurement of Crystal Growth and Nucleation Rates 2002, IChemE, Rugby, UK.
20. Hagler A.T., Bernstein J. Conformational polymorphism. 2. Crystal energetics by computational substitution. Further evidence for the sensitivity of the method. J. Am. Chem. Soc. 1978, 100(20):6349-6354.
21. Higuchi T. Pharmaceutical compounding and dispensing. American Pharmacy Series III 1949, J.B. Lippincott Co., Philadelphia, PA, 179 pp.
22. Higuchi T., Gupta M., Busse L.W. Influence of electrolytes, pH and alcohol concentration on the solubility of acidic drugs. J. Pharm. Sci. 1953, 42:157-161.
23. Hariharan P.C., Pople J.A. The influence of polarization functions on molecular orbital hydrogenation energies. Theor. Chim. Acta 1973, 28:213-222.
24. Itoh M., Kuniyoshi Y., Yokota M., Doki N., Shimizu K. Seeded batch cooling crystallization of tetrahydroxybenzophenone from acetone solution. Org. Proc. Res. Dev. 2008, 12(4):655-659.
25. Jeffrey G.A., Kim H.S. Conformations of the alditols. Cabohydr. Res. 1970, 14:207-216.
26. Jinno J., Oh D.M., Crison J.R., Amidon G.L. Dissolution of ionizable water-insoluble drugs: the combined effect of pH and surfactant. J. Pharm. Sci. 2000, 89(2):268-274.
27. Jones H.P., Davey R. Crystallization of a salt of a weak organic acid and base: solubility relations, supersaturation control and polymorphic behavior. J. Phys. Chem. B 2005, 109(11):5273-5278.
28. Kadam S.S., van der Windt E., Daudey P.J., Kramer H.J.M. A comparative study of ATR-FTIR and FT-NIR spectroscopy for in-situ concentration monitoring during batch cooling crystallization processes. Cryst. Growth Des. 2010, 10(6):2629-2640.
29. Kovács T., Párkányi L., Pelczer I., Cervantes-Lee F., Pannell K.H., Torrence P.F. Solid state and solution conformation of 3'-amino-3'-deoxythymidine, precursor to a noncompetitive inhibitor of HIV-1 reverse transcriptase. J. Med., Chem. 1991, 34(8):2595-2600.
30. Kubota N. Effect of impurities on the growth kinetics of crystals. Crys. Res. Technol. 2001, 36(8-10):749-769.
31. Kessler H., Zimmermann G., Forster H., Engel J., Oepen G., Sheldrick S.W. Does a molecule have the same conformation in the crystalline state and in solution? Comparison of NMR results for the solid state and solution with those of the X-ray structural determination. Angew. Chem. Int. Ed., Engl. 1981, 20(12):1053-1055.
32. Lowe J.P. Barriers to internal rotation about single bonds. Prog. Phys. Org. Chem. 1968, 6:1-80.
33. Lee C., Yang W., Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 1988, 37:785-789.
34. Lapple C.E., Shepherd C.B. Calculation of particle trajectories. Ind. Eng. Chem. 1940, 32(5):605-617.
35. Muller F.L., Fielding M., Black S.N. A practical approach for using solubility to design cooling crystallizations. Org. Proc. Res. Dev. 2009, 10.1021/op9001438.
36. Mullin J.W. Crystallization 2001, Butterworth Heinemann, Oxford, UK. fourth ed.
37. Migliaccio G.P., Byrn S.R. Comparisons of rotamer populations of nialamide, azaperone and chloroquine in solid state and in solution. J. Pharm. Sci. 1981, 70(3):284-287.
38. Mc Pherson A. Crystallization of Biological Macromolecules 1999, CSHL Press, New York.
39. March J. Advanced Organic Chemistry 1992, Wiley Interscience.
40. Ono T., Kramer H.J.M., Ter Horst J.H., Jansens P.J. Process modeling of the polymorphic transformation of l-glutamic acid. Crys. Growth Des. 2004, 4(6):1161-1167.
41. Prausnitz J.M., Lichtenthaler R.N., Gomes de Azevedo E. Molecular Thermodynamics of Fluid-Phase Equilibria 1999, Prentice-Hall, Upper Saddle River, NJ. third ed.
42. Parker G.R., Korp J.D. Comparison of solid and solution conformations of hydroxyurea and 3-ethyl-1-hydroxyurea. J. Pharm. Sci. 1978, 67(2):239-243.
43. Pudipeddi M., Serajuddin A.T.M., Grant D.J.W., Stahl P.H. Solubility and dissolution of weak acides, bases and salts. Handbook of Pharmaceutical Salts: Properties, Selection and Use 2002, 19-39. VHCA, Verlag Helvetica Chimica Acta, Zürich, (and Wiley-VCH, Weinheim). P.H. Stahl, C.G. Wermuth (Eds.).
44. Quadrifoglio F., Crescenzi V., Cesaro A., Delben F. Thermodynamic data for the water-hexamethylenetetramine system. J. Phys. Chem. 1971, 75(23):3633-3635.
45. Rippie E.G., Lang D.J., Romig P.W. Solubilization of weakly acidic and basic drugs by aqueous solutions of polysorbate 80. J. Pharm. Sci. 1964, 53(11):1346-1348.
46. Rossolov V., Pople J.A., Ratner M., Windus T.L. 6-31G* basis set for atoms K through Zn. J. Chem. Phys. 1998, 109:1223.
47. Svang-Ariyaskul A., William J., Rousseau R.W. Chiral separation using a novel combination of cooling crystallization and a membrane barrier: resolution of dl-glutamic acid. Chem. Eng. Sci. 2009, 64(9):1980-1984.
48. Sangwal K. Effect of impurities on the processes of crystal growth. J. Cryst. Growth 1993, 128(1-4, Part 2):1236-1244.
49. Siniti M., Jabrane S., Létoffé J.M. Study of the respective binary phase diagrams of sorbitol with mannitol, maltitol and water. Thermochim. Acta 1999, 325:171-180.
50. Serajuddin A.T.M., Pudipeddi M. Salt selection strategies. Handbook of Pharmaceutical Salts: Properties, Selection and Use 2002, 135-160. VHCA, Verlag Helvetica Chimica Acta, Zürich, (and Wiley-VCH, Weinheim). P.H. Stahl, C.G. Wermuth (Eds.).
51. Sheng J.J., Kasima N.A., Chandrasekharan R., Amidon G.L. Solubilization and dissolution of insoluble weak acid, ketoprofen: effects of pH combined with surfactant. Eur. J. Pharm. Sci. 2006, 29(3-4):306-314.
52. Yu L., Stephenson G.A., Mitchell C.A., Bunnell C.A., Snorek S.V., Bowyer J.J., Borchardt T.B., Stowell G.S., Byrn S. Thermochemistry and conformational polymorphism of a hexamorphic crystal system. J. Am. Chem. Soc. 2000, 122:585-591.
53. Yu L., Reutzel-Edens S.M., Mitchell C.A. Crystallization and polymorphism of conformationally flexible molecules: problems, patterns and strategies. Org. Proc. Res. Dev. 2000, 4:396-402.
54. Zanotti G., Falcigno L., Saviano M., D'Auria G., Bruno B.M., Campanile T., Paolillo L. Solid state and solution conformation of [Ala7]-Phalloidin. Chem. Eur. J. 2001, 7(7):1479-1485.