Impact of molecular flexibility on double polymorphism, solid solutions and chiral discrimination during crystallization of diprophylline enantiomers

Molecular Pharmaceutics

Volumn 10, Issue 10, 2013, Pages 3850-3861

  Brandel, Clément ^a   Amharar, Youness ^a   Rollinger, Judith M ^b   Griesser, Ulrich J ^b   Cartigny, Yohann ^a,c   Petit, Samuel ^a   Coquerel, Gérard ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITY OF INNSBRUCK   (Austria)

^c TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

Binary phase diagram; Chirality; Conformational polymorphism; Mixed crystals; Nucleation inhibitions; Preferential crystallization

Indexed keywords

DIPROPHYLLINE; SOLVENT; THEOPHYLLINE DERIVATIVE;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG CONFORMATION; DRUG STABILITY; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGEN BOND; PRIORITY JOURNAL; SOLID; THERMOSTABILITY; X RAY POWDER DIFFRACTION;

CALORIMETRY, DIFFERENTIAL SCANNING; CRYSTALLIZATION; DYPHYLLINE; MOLECULAR STRUCTURE; PROTEIN CONFORMATION; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 84888325597     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp400308u     Document Type: Article

References (66)

1. Bernstein, J. Polymorphism in Molecular Crystals; Clarendon Press: Oxford, 2002.
2. Hilfiker, R.; Blatter, F.; von Raumer, M. Relevance of Solid-state Properties for Pharmaceutical Products. In Polymorphism in the Pharmaceutical Industry; Hilfiker, R., Ed.; Wiley VCH: Weinheim, 2006; pp 1-19.
3. Grant, D. J. W. Theory and Origin of Polymorphism. In Polymorphism in Pharmaceutical Solids; Brittain, H. G., Ed.; Informa Healthcare: New York, 1999; pp 1-34.
4. Stahly, G. P. Diversity in Single-and Multiple-Component Crystals. The Search for and Prevalence of Polymorphs and Cocrystals. Cryst. Growth Des. 2007, 7, 1007-1026.
5. Sheth, A. R.; Grant, D. J. W. Relationship between the Structure and Properties of Pharmaceutical Crystals. KONA 2005, 23, 36-48.
6. Brittain, H. G. The Impact of Polymorphism on Drug Development: a Regulatory Viewpoint. Am. Pharm. Rev. 2000, 3, 67-68.
7. Burger, A.; Ramberger, R. On the Polymorphism of Pharmaceuticals and other Molecular Crystals. Mikrochim. Acta 1979, II, 259-271.
8. Mullin, J. W. Crystallization, 4th ed.; Butterworth-Heinemann: Oxford, 2001.
9. Davey, R. J.; Blagden, N.; Potts, G. D.; Docherty, R. Polymorphism in Molecular Crystals: Stabilization of a Metastable Form by Conformational Mimicry. J. Am. Chem. Soc. 1997, 119, 1767-1772.
10. Threlfall, T. Structural and Thermodynamic Explanations of Ostwald's Rule. Org. Process Res. Dev. 2003, 7, 1017-1027.
11. Dunitz, J. D.; Bernstein, J. Disappearing Polymorphs. Acc. Chem. Res. 1995, 28, 193-200.
12. Bernstein, J.; Davey, R. J.; Henck, J. O. Concomitant Polymorphs. Angew. Chem., Int. Ed. 1999, 38, 3440-3461.
13. Bernstein, J.; Hagler, T. Conformational Polymorphism. The Influence of Crystal Structure on Molecular Conformation. J. Am. Chem. Soc. 1978, 100, 673-681.
14. Bernstein, J. Conformational Polymorphism. In Organic Solid State Chemistry; Desiraju, G., Ed.; Elsevier: Amsterdam, 1987; pp 471-518.
15. Hursthouse, M. B.; Huth, L. S.; Threlfall, T. L. Why Do Organic Compounds Crystallise Well or Badly or Ever so Slowly? Why Is Crystallisation Nevertheless Such a Good Purification Technique? Org. Process Res. Dev. 2009, 13, 1231-1240.
16. Bernstein, J.; Dunitz, J. D.; Gavezzotti, A. Polymorphic Perversity: Crystal Structures with Many Symmetry-Independent Molecules in the Unit Cell. Cryst. Growth Des. 2008, 8, 2011-2018.
17. Grant, D. J. W.; Gu, C. G. Effects of Crystal Structure and Physical Properties on the Release of Chiral Drugs. In Chirality in Drug Design and Development; Reddy, I. K., Mehvar, R., Eds.; Marcel Dekker: 2004; pp 1-33.
18. Saigo, K.; Sakai, K. Resolution of Chiral Drugs and Drug Intermediates by Crystallisation. In Chirality in Drug Research; Francotte, E., Lindner, W., Eds.; Wiley-VCH: Weinheim, 2006; pp 127-154.
19. Jacques, J.; Collet, A.; Wilen, S. Enantiomers, Racemates and Resolutions; Krieger Publishing Company: Malabar, FL, 1994.
20. Coquerel, G. Review on the Heterogeneous Equilibria between Condensed Phases in Binary Systems of Enantiomers. Enantiomer 2000, 5, 481-498.
21. Esteves de Castro, R. A.; Canotilho, J.; Barbosa, R. M.; Silva, M. R.; Beja, A. M.; Paixáo, J. A.; Redinha, J. S. Conformational Isomorphism of Organic Crystals: Racemic and Homochiral Atenolol. Cryst. Growth Des. 2007, 7, 496-500.
22. Huang, J.; Chen, S.; Guzei, I. A.; Yu, L. Discovery of a Solid Solution of Enantiomers in a Racemate-Forming System by Seeding. J. Am. Chem. Soc. 2006, 128, 11985-11992.
23. Marthi, K.; Larsen, S.; Acs, M.; Balint, J.; Fogassy, E. Structures with Identical Packing; Racemic and Partially Optically Pure 3-(2'-chloro-2'- phenylethyl)-2-thiazolidiniminium p-Toluenesulfonate and a Comparison of the Packing in Corresponding Racemic and Optically Active Compounds. Acta Crystallogr. 1994, B50, 762-771.
24. de Diego, H. L.; Bond, A. D.; Dancer, R. J. Formation of Solid Solutions between Racemic and Enantiomeric Citalopram Oxalate. Chirality 2011, 23, 408-416.
25. Bredikhin, A. A.; Bredikhina, Z. A.; Zakharychev, D. V.; Gubaidullin, A. T.; Fayzullin, R. R. Chiral Drug Timolol Maleate as a Continuous Solid Solution: Thermochemical and Single Crystal X-ray Evidence. CrystEngComm 2011, 14, 648-655.
26. Vogt, F. G.; Copley, R. C. B.; Mueller, R. L.; Spoors, G. P.; Cacchio, T. N.; Carlton, R. A.; Katrincic, L. M.; Kennady, J. M.; Parsons, S.; Chetina, O. V. Isomorphism, Disorder, and Hydration in the Crystal Structures of Racemic and Single-Enantiomer Carvedilol Phosphate. Cryst. Growth Des. 2010, 10, 2713-2733.
27. Corvis, Y.; Négrier, P.; Massip, S.; Leger, J.-M.; Espeau, P. Insights into the Crystal Structure, Polymorphism and Thermal Behavior of Menthol Optical Isomers and Racemates. CrystEngComm 2012, 14, 7055-7064.
28. Oonk, H. A. J.; Kroon, J. The Carvoxime System. I. X-ray Study of dl-Carvoxime (m.p. 92°C). Acta Crystallogr. 1976, B32, 500-504.
29. Chen, S.; Xi, H.; Henry, R. F.; Marsden, I.; Zhang, G. G. Z. Chiral Co-Crystal Solid Solution: Structures, Melting Point Phase Diagram, and Chiral Enrichment of (ibuprofen)2(4, 4-dipyridyl). CrystEngComm 2010, 12, 1485-1493.
30. Baert, F.; Fogret, R.; Oonk, H. A. J.; Kroon, J. The Carvoxime System. V. X-ray Study of a Mixed Crystal of Carvoxime. Acta Crystallogr. 1978, B34, 222-226.
31. Gallis, H. E.; van Ekeren, P. J.; van Miltenburg, J. C.; Oonk, H. A. J. Mixtures of d-and l-Carvone IV. Transformation from a Solid Solution to a Racemic Compound. Thermochim. Acta 1999, 326, 83-90.
32. Rollinger, J. M.; Burger, A. Polymorphism of Racemic Felodipine and the Unusual Series of Solid Solutions in the Binary System of its Enantiomers. J. Pharm. Sci. 2001, 90, 949-959.
33. Gallis, H. E.; Cees van Miltenburg, J.; Oonk, H. A. J. Polymorphism of Mixtures of Enantiomers: A Thermodynamic Study of Mixtures of D-and L-Limonene. Phys. Chem. Chem. Phys. 2000, 2, 5619-5623.
34. Chion, B.; Lajzerowicz, J.; Bordeaux, D.; Collet, A.; Jacques, J. Structural Aspects of Solid Solutions of Enantiomers. The 3-Hydroxymethyl-and 3-Carboxy-2, 2, 5, 5-tetramethylpyrrolidinyl 1-Oxyl Systems as Examples. J. Phys. Chem. B 1978, 82, 2682-2688.
35. Burger, A.; Rollinger, J. M.; Brüggeller, P. Binary System of (R)-and (S)-Nitrendipine-Polymorphism and Structure. J. Pharm. Sci. 1997, 86, 674-679.
36. Kaemmerer, H.; Lorenz, H.; Black, S. N.; Seidel-Morgenstern, A. Study of System Thermodynamics and the Feasibility of Chiral Resolution of the Polymorphic System of Malic Acid Enantiomers and Its Partial Solid Solutions. Cryst. Growth Des. 2009, 9, 1851-1862.
37. Lorenz, H.; Langermann, von, J.; Sadiq, G.; Seaton, C. C.; Davey, R. J.; Seidel-Morgenstern, A. The Phase Behavior and Crystallization of 2-Chloromandelic Acid: The Crystal Structure of the Pure Enantiomer and the Behavior of Its Metastable Conglomerate. Cryst. Growth Des. 2011, 11, 1549-1556.
38. Zhang, G. G. Z.; Paspal, S. Y. L.; Suryanarayanan, R.; Grant, D. J. W. Racemic Species of Sodium Ibuprofen: Characterization and Polymorphic Relationships. J. Pharm. Sci. 2003, 92, 1356-1366.
39. Matell, M. On the Conditions for the Formation of Quasiracemic Compounds II Alkylsuccinic Acids and S-Alkylmercapto-3-succinic Acids. Ark. Kemi 1952, 5, 17-37.
40. Linol, J.; Morelli, T.; Petit, M.-N.; Coquerel, G. Inversion of the Relative Stability between Two Polymorphic Forms of Modafinil under Dry High-Energy Milling: Comparisons with Results Obtained under Wet High-Energy Milling. Cryst. Growth Des. 2007, 7, 1608. 1611.
41. Neckebrock, O.; Courvoisier, L.; Graf, S.; Serrure, G.; Coquerel, G.; Rose, S.; Besselievre, C.; Mallet, F.; Van Langevelde, A. J. 2006, US patent 20060241320 A1.
42. Rietveld, I. B.; Barrio, M.; Do, B.; Tamarit, J.-L.; Céolin, R. Overall Stability for the Ibuprofen Racemate: Experimental and Topological Results Leading to the Pressure.Temperature Phase Relationships between its Racemate and Conglomerate. J. Phys. Chem. B 2012, 116, 5568-5574.
43. Weissbuch, I.; Lahav, M.; Leiserowitz, L. Toward Stereochemical Control, Monitoring, and Understanding of Crystal Nucleation. Cryst. Growth Des. 2003, 3, 125-150.
44. Tamura, R.; Fujimoto, D.; Lepp, Z.; Misaki, K.; Miura, H.; Takahashi, H.; Ushio, T.; Nakai, T.; Ken, H. Mechanism of Preferential Enrichment, an Unusual Enantiomeric Resolution Phenomenon Caused by Polymorphic Transition during Crystallization of Mixed Crystals Composed of Two Enantiomers. J. Am. Chem. Soc. 2002, 124, 13139-13153.
45. Seton, L.; Khamar, D.; Bradshaw, I. J.; Hutcheon, G. A. Solid State Forms of Theophylline: Presenting a New Anhydrous Polymorph. Cryst. Growth Des. 2010, 10, 3879-3886.
46. Griesser, U. J.; Burger, A. The Polymorphic Drug Substances of the European Pharmacopoeia, Part 8: Thermal Analytical and FTIRMicroscopic Investigations of Etophylline Crystal Forms. Sci. Pharm. 1993, 61, 133-143.
47. Griesser, U. J.; Auer, M. E.; Burger, A. Micro-thermal analysis, FTIR-and Raman-Microscopy of (R, S)-Proxyphylline Crystal Forms. Microchem. J. 2000, 65, 283-292.
48. Griesser, U. J.; Auer, M. E.; Burger, A. The Polymorphic Drug Substances of the European Pharmacopoeia, Part 10: Diprophylline. Sci. Pharm. 1999, 67, 319-330.
49. Bruker SMART (5.059) and SAINT (6.01); Bruker AXS Inc.: Madison, WI, 1997.
50. Sheldrick, G. M. SHELXS97 and SHELXL97; Institüt für Anorganische Chemie der Universität: Gottingen, Germany, 1997.
51. Sun, C.; Zhou, D.; Grant, D. J. W.; Young, V. G. Theophylline Monohydrate. Acta Crystallogr. 2002, E58, o368-o370.
52. Ebisuzaki, Y.; Boyle, P. D.; Smith, J. A. Methylxanthines. I. Anhydrous Theophylline. Acta Crystallogr. 1997, C53, 777-779.
53. Khamar, D.; Pritchard, R. G.; Bradshaw, I. J.; Hutcheon, G. A.; Seton, L. Polymorphs of Anhydrous Theophylline: Stable Form IV Consists of Dimer Pairs and Metastable Form I consists of Hydrogen Bonded Chains. Acta Crystallogr. 2011, C67, 496-499.
54. Coquerel, G. The "Structural Purity" of Molecular Solids-An Elusive Concept? Chem. Eng. Process. 2006, 45, 857-862.
55. Ricci, J. E. The Phase Rule and Heterogeneous Equilibrium; Dover Publications: 1966.
56. Roozeboom, H. W. B. Löslichkeit und Schmelzpunkt als Kriterien fu.r Racemische Verbindungen, Pseudoracemische Mischkrystalle und Inaktive Konglomerate. Z. Phys. Chem. 1899, 28, 494-517.
57. Coquerel, G. Preferential Crystallization. In Novel Optical Resolution Technologies, Series: Topics in Current Chemistry, Vol. 269; Sakai, K., Hirayama, N., Tamura, R., Eds.; Springer-Verlag: Berlin, Heidelberg, 2007; pp 1-51.
58. Galland, A.; Dupray, V.; Lafontaine, A.; Berton, B.; Sanselme, M.; Atmani, H.; Coquerel, G. Preparative Resolution of (±)-trans-1, 2-diaminocyclohexane by means of Preferential Crystallization of its Citrate Monohydrate. Tetrahedron: Asymmetry 2010, 21, 2212-2217.
59. Dufour, F.; Gervais, C.; Petit, M. N.; Perez, G.; Coquerel, G. Investigations on the Reciprocal Ternary System (±)-2-Phenylpropionic Acid.(±)-α-Methylbenzylamine. Impact of an Unstable Racemic Compound on the Simultaneous Resolution of Chiral Acids and Bases by Preferential Crystallisation. J. Chem. Soc., Perkin Trans. 2 2001, 2022-2036.
60. Houllemare-Druot, S.; Coquerel, G. How far can an Unstable Racemic Compound affect the Performances of Preferential Crystallization? Example with (R) and (S)-α-Methylbenzylamine Chloroacetate. J. Chem. Phys., Perkin Trans. 2 1998, 2211-2220.
61. Beilles, S.; Cardinael, P.; Ndzié, E.; Petit, S.; Coquerel, G. Preferential Crystallisation and Comparative Crystal Growth study between Pure Enantiomer and Racemic Mixture of a Chiral Molecule: 5-ethyl-5-methylhydantoin. Chem. Eng. Sci. 2001, 56, 2282-2294.
62. Gervais, C.; Beilles, S.; Cardinaél, P.; Petit, S.; Coquerel, G. Oscillating Crystallization in Solution between (+)-and (.)-5-Ethyl-5- methylhydantoin under the Influence of Stirring. J. Phys. Chem. B 2002, 106, 646-652.
63. Renou, L.; Morelli, T.; Coste, S.; Petit, M.-N.; Berton, B.; Malandain, J.-J.; Coquerel, G. Chiral Discrimination at the Solid State of methyl 2-(diphenylmethylsulfinyl)acetate. Cryst. Growth Des. 2007, 7, 1599-1607.
64. Wermester, N.; Aubin, E.; Pauchet, M.; Coste, S.; Coquerel, G. Preferential Crystallization in an Unusual Case of Conglomerate with Partial Solid Solutions. Tetrahedron: Asymmetry 2007, 18, 821-831.
65. Levilain, G.; Coquerel, G. Pitfalls and Rewards of Preferential Crystallization. CrystEngComm 2010, 12, 1983-1992.
66. Davey, R. J.; Schroeder, S. L. M.; ter Horst, J. H. Nucleation of Organic Crystals-A Molecular Perspective. Angew. Chem., Int. Ed. 2013, 52, 2-16.