Development of a targeted polymorph screening approach for a complex polymorphic and highly solvating API

Journal of Pharmaceutical Sciences

Volumn 99, Issue 9, 2010, Pages 3874-3886

  Campeta, Anthony M ^a   Chekal, Brian P ^a   Abramov, Yuriy A ^a   Meenan, Paul A ^a   Henson, Mark J ^a,b   Shi, Bing ^a   Singer, Robert A ^a   Horspool, Keith R ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^b Molecular Biometrics Inc   (United States)

Author keywords

Axitinib; Computational chemistry; Crystal structure; Crystallization; Desolvation; Polymorph screen; Polymorphism

Indexed keywords

ALCOHOL; AXITINIB;

ARTICLE; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG SCREENING; DRUG SOLUBILITY; HIGH TEMPERATURE; HYDROGEN BOND; SOLVATION; THERMOSTABILITY;

EID: 77956378312     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22230     Document Type: Article

References (31)

1. Bernstein J. 2002. Polymorphismin molecular crystals. Oxford: Oxford University Press.
2. (a) Hilfiker R. 2006. Polymorphism in the pharmaceutical industry. New York: Wiley-VCH;
3. (b) Brittain H. 2009, 2nd ed. Polymorphism in pharmaceutical solids. New York: Marcel Dekker, Inc.;
4. (c) Byrn S. 1999. Solid state-chemistry of drugs. West Lafayette, IN: SSCI, Inc.
5. Quallich G. 2006. In: Fundamentals of early clinical drug development: From synthesis design to formulation. Abdel-Magid A, Caron S, editors. New York: John Wiley and Sons. pp 238.
6. Bauer J, Spanton S, Henry R, Quick J, Dziki W, Porter W, Morris J. 2001. Ritonavir: An extraordinary example of conformational polymorphism. Pharm Res 18:859-866.
7. Desikan S, Parsons R, Jr., Davis WP, Ward JE, Marshall WJ, Toma PH. 2005. Process development challenges to accommodate a late-appearing stable polymorph: A case study on the polymorphism and crystallization of a fast-track drug development compound. Org Process Res Dev 9:933-942. (Pubitemid 41784117)
8. Ostwald W. 1897. Studienüber die Bildung und Umwandlung fester Kocombining double acute accentrper. Z Phys Chem 22:289-330.
9. (a) Kania RS, Bender SL, Borchardt AJ, Cripps SJ, Palmer CL, Tempczyk-Russell AM, Varney MD, Collins RC. 2003. Indazole compounds and pharmaceutical compositions for inhibiting protein kinases, and methods for their use. US Patent 6531491;
10. (b) Kania RS, Bender SL, Borchardt AJ, Cripps SJ, Hua Y, Johnson MD, Johnson Jr. TO, Luu HT, Palmer CL, Reich SH, Tempczyk-Russell AM, Teng M, Thomas C, Varney MD, Wallace MB, Collins RC. 2003. Indazole compounds and pharmaceutical compositions for inhibiting protein kinases, and methods for their use. US Patent 6534524.
11. Hu-Lowe DD, Zou HY, Grazzini ML, Hallin ME, Wickman GR, Amundson K, Chen JH, Rewolinski DA, Yamazaki S, Wu EY, McTigue MA, Murray BW, Kania RS, O'Connor P, Shalinsky DR, Bender SL. 2008. Nonclinical antiangiogenesis and antitumor activities of axitinib (AG-013736), an oral, potent, and selective inhibitor of vascular endothelial growth factor receptor tyrosine kinases 1, 2, 3. Clin Cancer Res 14:7272-7283.
12. Chekal BP, Campeta AM, Abramov YA, Feeder N, Glynn PP, McLaughlin RW, Meenan PA, Singer RA. 2009. The challenges of developing an API crystallization process for a complex polymorphic and highly solvating system. Part I. Org Process Res Dev 13:1327-1337.
13. Mullin JW. 2001. Crystallization. 4th edition. Oxford, UK: Butterworth-Heinemann. pp 16-18.
14. Ye Q, Hart RM, Kania R, Ouellette M, Wu ZP, Zook SE. 2006. Polymorphic forms of 6-[(2-methylcarbomoyl)phenylsulfanyl]-3-E-[(2-pyridin-2-yl)ethenyl] indazole. US Patent 0094763.
15. Campeta AM, Chekal BP, McLaughlin RW, Singer RA. 2008. Novel crystalline forms of a vegf-r inhibitor. PCT Int Appl WO 2008122858.
16. Accelrys. DMol3, Materials Studio version 4.4. http://www.accelrys.com/ products/mstudio/.
17. Perdew JP, Burke K, Ernzerhof M. 1996. Generalized gradient approximation made simple. Phys Rev Lett 77:3865-3868.
18. Andzelm J, Kolmel C, Klamt A. 1995. Incorporation of solvent effects into density functional calculations of molecular energies and geometries. J Chem Phys 103:9312-9320.
19. Klamt A. 2005. COSMO-RS: From quantum chemistry to fluid-phase thermodynamics and drug design. Amsterdam: Elsevier.
20. COSMOLogic GmbH. COSMOTherm Version C21-0108. Leverkusen, Germany: COSMOLogic GmbH.
21. Burger A, Ramberger R. 1979. On the polymorphism of pharmaceuticals and other molecular crystals II. Applicability of thermodynamic rules. Mikrochim Acta II 273-313.
22. Abramov YA, Mustakis J, am Ende D. 2009. COSMO-RS applications in pharmaceutical science. COSMO-RS-Symposium 2009, Leverkusen, Germany.
23. Abramov YA, to be published. In preparation.
24. (a) Becke AD. 1988. Density functional exchange-energy approximation with correct asymptotic behaviour. Phys Rev A 38:3098-3100;
25. (b) Perdew JP. 1986. Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Phys Rev B 33:8822-8824.
26. Nicolai B, Espeau P, Céolin R, Perrin M-A, Zaske L, Giovannini J, Leveiller F. 2007. Polymorph formation from solvate desolvation. Spironolactone forms I and II and the spironolactoneethanol solvate. J Therm Anal Cal 90:337-339.
27. Mallet F, Petit S, Lafont S, Billot P, Lemarchand D, Coquerel G. 2003. Solvent exchanges among molecular compounds. Two extreme cases of pharmaceutical interest. J Therm Anal Cal 73:459-471.
28. Stephenson GA, Groleau EG, Kleemann RL, Xu W, Rigsbee DR. 1998. Formation of isomorphic desolvates: Creating a molecular vacuum. J Pharm Sci 87:536-542.
29. Caira MR, Bettinetti G, Sorrenti M, Catenacci L. 2007. Relationships between structural and thermal properties of anhydrous and solvated crystalline forms of brodimoprim. J Pharm Sci 96:996-1007. (Pubitemid 46797471)
30. Garnier S, Petit S, Coquerel G. 2002. Dehydration mechanism and crystallization behaviour of lactose. J Therm Anal Cal 68:489-502.
31. Gu CH, Young V, Jr., Grant DJW. 2001. Polymorph screening: Influence of solvents on the rate of solvent-mediated polymorphic transformation. J Pharm Sci 90:1878-1890.