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Volumn 2, Issue , 2011, Pages 259-280

Crystal polymorphism in chemical process development

Author keywords

crystal growth; crystallization process development; nucleation; phase transformation; polymorph screening; structure property relationship

Indexed keywords

CHEMICAL DEVELOPMENT; CHEMICAL PROCESS DEVELOPMENT; CRYSTAL POLYMORPHISM; CRYSTALLIZATION PROCESS DEVELOPMENT; DRUG SUBSTANCES; PHASE TRANSFORMATION; POLYMORPH SCREENING; QUALITY ATTRIBUTES; SELECTION PROCESS; SOLID FORMS; SOLID-PHASE; STRUCTURE PROPERTY RELATIONSHIPS;

EID: 79959385956     PISSN: 19475438     EISSN: None     Source Type: Journal    
DOI: 10.1146/annurev-chembioeng-061010-114224     Document Type: Review
Times cited : (354)

References (132)
  • 3
    • 0000110278 scopus 로고
    • On the relationship between crystalline form and chemical composition. I. Note on arsenates and phosphates
    • Mitscherlich E. 1822. On the relationship between crystalline form and chemical composition. I. Note on arsenates and phosphates. Ann. Chim. Phys. 19:350-419
    • (1822) Ann. Chim. Phys. , vol.19 , pp. 350-419
    • Mitscherlich, E.1
  • 4
    • 0034345205 scopus 로고    scopus 로고
    • Crystallization and polymorphism of conformationally flexible molecules: Problems, patterns, and strategies
    • Yu L, Reutzel-Edens SM, Mitchell CA. 2000. Crystallization and polymorphism of conformationally flexible molecules: Problems, patterns, and strategies. Org. Process Res. Dev. 4:396-402
    • (2000) Org. Process Res. Dev. , vol.4 , pp. 396-402
    • Yu, L.1    Reutzel-Edens, S.M.2    Mitchell, C.A.3
  • 5
    • 27744459901 scopus 로고    scopus 로고
    • Thermochemical analysis of venlafaxine hydrochloride polymorphs 1-5
    • DOI 10.1021/cg0580096
    • Roy S,Aitipamula S,NangiaA. 2005. Thermochemical analysis of venlafaxine hydrochloride polymorphs 1-5. Cryst. Growth Des. 5:2268-76 (Pubitemid 41619321)
    • (2005) Crystal Growth and Design , vol.5 , Issue.6 , pp. 2268-2276
    • Roy, S.1    Aitipamula, S.2    Nangia, A.3
  • 6
    • 0344583871 scopus 로고    scopus 로고
    • Anhydrates and Hydrates of Olanzapine: Crystallization, Solid-State Characterization, and Structural Relationships
    • DOI 10.1021/cg034055z
    • Reutzel-Edens SM, Bush JK, Magee PA, Stephenson GA, Byrn SR. 2003. Anhydrates and hydrates of olanzapine: Crystallization, solid-state characterization, and structural relationships. Cryst. Growth Des. 3:897-907 (Pubitemid 37467740)
    • (2003) Crystal Growth and Design , vol.3 , Issue.6 , pp. 897-907
    • Reutzel-Edens, S.M.1    Bush, J.K.2    Magee, P.A.3    Stephenson, G.A.4    Byrn, S.R.5
  • 8
    • 34250723366 scopus 로고    scopus 로고
    • Tautomeric polymorphism in omeprazole
    • DOI 10.1039/b700506g
    • Bhatt PM, Desiraju GR. 2007. Tautomeric polymorphism in omeprazole. Chem. Commun. 2007:2057-59 (Pubitemid 46959487)
    • (2007) Chemical Communications , Issue.20 , pp. 2057-2059
    • Bhatt, P.M.1    Desiraju, G.R.2
  • 10
    • 0036396046 scopus 로고    scopus 로고
    • Polymorphism vs. desmotropy: The cases of 3-phenyl- and 5-phenyl-1H-pyrazoles and 3-phenyl-1H-indazole
    • DOI 10.1002/1522-2675(200209)85: 9<2763::AID-HLCA2763>3.0.CO;2-R
    • Garcia MA, Lopez C, Claramunt RM, Kenz A, PierrotM, et al. 2002. Polymorphism versus desmotropy: The cases of 3-phenyl- and 5-phenyl-1H-pyrazoles and 3-phenyl-1H-indazole. Helv. Chim. Acta 85:2763-76 (Pubitemid 35177799)
    • (2002) Helvetica Chimica Acta , vol.85 , Issue.9 , pp. 2763-2776
    • Garcia, M.A.1    Lopez, C.2    Claramunt, R.M.3    Kenz, A.4    Pierrot, M.5    Elguero, J.6
  • 12
    • 0000776859 scopus 로고
    • Polymorphism
    • ed. D Fox, MM Labes, AWeissberger, New York: Wiley Intersci.
    • McCroneWC. 1965. Polymorphism. In Physics and Chemistry of the Organic Solid State, ed. D Fox, MM Labes, AWeissberger, 2:725-67. New York: Wiley Intersci.
    • (1965) Physics and Chemistry of the Organic Solid State , vol.2 , pp. 725-767
    • McCrone, W.C.1
  • 14
    • 19744382415 scopus 로고    scopus 로고
    • Pseudopolymorph: A polemic
    • DOI 10.1021/cg030084y, Polymorphins in Crystals
    • Seddon KR. 2004. Pseudopolymorph: A polemic. Cryst. Growth Des. 4:1087 (Pubitemid 39531983)
    • (2004) Crystal Growth and Design , vol.4 , Issue.6 , pp. 1087
    • Seddon, K.R.1
  • 15
    • 8844247861 scopus 로고    scopus 로고
    • Counterpoint: What's in a name?
    • DOI 10.1021/cg030085q, Polymorphins in Crystals
    • Desiraju GR. 2004. Counterpoint: What's in a name? Cryst. Growth Des. 4:1089-90 (Pubitemid 39531984)
    • (2004) Crystal Growth and Design , vol.4 , Issue.6 , pp. 1089-1090
    • Desiraju, G.R.1
  • 16
    • 25444489017 scopus 로고    scopus 로고
    • And another comment on pseudopolymorphism
    • Bernstein J. 2005. ⋯ And another comment on pseudopolymorphism. Cryst. Growth Des. 5:1661-62
    • (2005) Cryst. Growth Des. , vol.5 , pp. 1661-1662
    • Bernstein, J.1
  • 17
    • 31144469641 scopus 로고    scopus 로고
    • Pseudopolymorph: Retain this widely accepted term
    • DOI 10.1021/cg050343e
    • Nangia A. 2006. Pseudopolymorph: Retain this widely accepted term. Cryst. Growth Des. 6:2-4 (Pubitemid 43130513)
    • (2006) Crystal Growth and Design , vol.6 , Issue.1 , pp. 2-4
    • Nangia, A.1
  • 19
    • 84890662885 scopus 로고    scopus 로고
    • The importance of solvates
    • ed. R Hilfiker, Weinheim: Wiley-VCH
    • Griesser UJ. 2006. The importance of solvates. In Polymorphism in the Pharmaceutical Industry, ed. R Hilfiker, pp. 211-33. Weinheim:Wiley-VCH
    • (2006) Polymorphism in the Pharmaceutical Industry , pp. 211-233
    • Griesser, U.J.1
  • 20
    • 0035897596 scopus 로고    scopus 로고
    • Chemical reactivity in solid-state pharmaceuticals: Formulation implications
    • DOI 10.1016/S0169-409X(01)00102-8, PII S0169409X01001028
    • Byrn SR, Xu W, Newman AW. 2001. Chemical reactivity in solid-state pharmaceuticals: Formulation implications. Adv. Drug Deliv. Rev. 48:115-36 (Pubitemid 32452294)
    • (2001) Advanced Drug Delivery Reviews , vol.48 , Issue.1 , pp. 115-136
    • Byrn, S.R.1    Xu, W.2    Newman, A.W.3
  • 21
    • 0141822419 scopus 로고
    • Polymorphs of nitrofurantoin. I. Preparation and X-ray crystal structures of two monohydrated forms of nitrofurantoin
    • Pienaar EW, CairaMR, Lotter AP. 1993. Polymorphs of nitrofurantoin. I. Preparation and X-ray crystal structures of two monohydrated forms of nitrofurantoin. J. Crystallogr. Spectrosc. 23:739-44
    • (1993) J. Crystallogr. Spectrosc. , vol.23 , pp. 739-744
    • Pienaar, E.W.1    Caira, M.R.2    Lotter, A.P.3
  • 23
    • 3042686291 scopus 로고    scopus 로고
    • Improving the filterability and solid density of ranitidine hydrochloride Form 1
    • DOI 10.1002/jps.20074
    • Mirmehrabi M, Rohani S, Murthy KSK, Radatus B. 2004. Improving the filterability and solid density of ranitidine hydrochloride form 1. J. Pharm. Sci. 93:1692-700 (Pubitemid 38823698)
    • (2004) Journal of Pharmaceutical Sciences , vol.93 , Issue.7 , pp. 1692-1700
    • Mirmehrabi, M.1    Rohani, S.2    Murthy, K.S.K.3    Radatus, B.4
  • 25
    • 0031484244 scopus 로고    scopus 로고
    • Purification of dirithromycin. Impurity reduction and polymorph manipulation
    • Wirth DD, Stephenson GA. 1997. Purification of dirithromycin. Impurity reduction and polymorph manipulation. Org. Process Res. Dev. 1:55-60
    • (1997) Org. Process Res. Dev. , vol.1 , pp. 55-60
    • Wirth, D.D.1    Stephenson, G.A.2
  • 26
    • 0036857517 scopus 로고    scopus 로고
    • Taking advantage of polymorphism to effect an impurity removal: Development of a thermodynamic crystal form of (R,R)-formoterol tartrate
    • Tanoury GJ, Hett R, Kessler DW,Wald SA, Senanayake CH. 2002. Taking advantage of polymorphism to effect an impurity removal: Development of a thermodynamic crystal form of (R,R)-formoterol tartrate. Org. Process Res. Dev. 6:855-62
    • (2002) Org. Process Res. Dev. , vol.6 , pp. 855-862
    • Tanoury, G.J.1    Hett, R.2    Kessler, D.W.3    Wald, S.A.4    Senanayake, C.H.5
  • 28
    • 34247478122 scopus 로고    scopus 로고
    • Polymorphism and solvatomorphism 2005
    • DOI 10.1002/jps.20772
    • Brittain HG. 2007. Polymorphism and solvatomorphism 2005. J. Pharm. Sci. 96:705-28 (Pubitemid 46657863)
    • (2007) Journal of Pharmaceutical Sciences , vol.96 , Issue.4 , pp. 705-728
    • Brittain, H.G.1
  • 29
    • 53549119401 scopus 로고    scopus 로고
    • Polymorphism and solvatomorphism 2006
    • Brittain HG. 2008. Polymorphism and solvatomorphism 2006. J. Pharm. Sci. 97:3611-36
    • (2008) J. Pharm. Sci. , vol.97 , pp. 3611-3636
    • Brittain, H.G.1
  • 30
    • 65949088359 scopus 로고    scopus 로고
    • Polymorphism and solvatomorphism 2007
    • Brittain HG. 2009. Polymorphism and solvatomorphism 2007. J. Pharm. Sci. 98:1617-42
    • (2009) J. Pharm. Sci. , vol.98 , pp. 1617-1642
    • Brittain, H.G.1
  • 31
    • 77956356726 scopus 로고    scopus 로고
    • Polymorphism and solvatomorphism 2008
    • Brittain HG. 2010. Polymorphism and solvatomorphism 2008. J. Pharm. Sci. 99:3648-64
    • (2010) J. Pharm. Sci. , vol.99 , pp. 3648-3664
    • Brittain, H.G.1
  • 44
    • 34347245300 scopus 로고    scopus 로고
    • Diversity in single- and multiple-component crystals. The search for and prevalence of polymorphs and cocrystals
    • Stahly GP. 2007. Diversity in single- and multiple-component crystals. The search for and prevalence of polymorphs and cocrystals. Cryst. Growth Des. 7:1007-26
    • (2007) Cryst. Growth Des. , vol.7 , pp. 1007-1026
    • Stahly, G.P.1
  • 45
    • 0030730571 scopus 로고    scopus 로고
    • POLYMORPHIE UND THERMISCHE ANALYSE PHARMAZEUTISCHER WIRKSTOFFE
    • Grunenberg A. 1997. Polymorphie und thermische analyse pharmazeutischer wirkstoffe. Pharmazie 26:224-31 (Pubitemid 27514542)
    • (1997) Pharmazie in Unserer Zeit , vol.26 , Issue.5 , pp. 224-231
    • Grunenberg, A.1
  • 46
    • 33847016492 scopus 로고    scopus 로고
    • Organic crystal hydrates: What are the important factors for formation
    • Infantes L, Fabian L, Motherwell WDS. 2007. Organic crystal hydrates: What are the important factors for formation. CrystEngComm 9:65-71
    • (2007) CrystEngComm , vol.9 , pp. 65-71
    • Infantes, L.1    Fabian, L.2    Motherwell, W.D.S.3
  • 47
    • 27944487022 scopus 로고    scopus 로고
    • Occurrence of pharmaceutically acceptable anions and cations in the Cambridge Structural Database
    • DOI 10.1002/jps.20441
    • Haynes DA, JonesW, Motherwell WDS. 2005. Occurrence of pharmaceutically acceptable anions and cations in the Cambridge Structural Database. J. Pharm. Sci. 94:2111-20 (Pubitemid 41665273)
    • (2005) Journal of Pharmaceutical Sciences , vol.94 , Issue.10 , pp. 2111-2120
    • Haynes, D.A.1    Jones, W.2    Motherwell, W.D.S.3
  • 48
    • 0033531678 scopus 로고    scopus 로고
    • Pseudopolymorphism: Occurrences of hydrogen bonding organic solvents in molecular crystals
    • Nangia A, Desiraju GR. 1999. Pseudopolymorphism: Occurrences of hydrogen bonding organic solvents in molecular crystals. Chem. Commun. 1999:605-6 (Pubitemid 29158703)
    • (1999) Chemical Communications , Issue.7 , pp. 605-606
    • Nangia, A.1    Desiraju, G.R.2
  • 50
    • 77956948010 scopus 로고    scopus 로고
    • Polymorphism in molecular solids: An extraordinary system of red, orange, and yellow crystals
    • Yu L. 2010. Polymorphism in molecular solids: An extraordinary system of red, orange, and yellow crystals. Acc. Chem. Res. 43:1257-66
    • (2010) Acc. Chem. Res. , vol.43 , pp. 1257-1266
    • Yu, L.1
  • 51
    • 0037165441 scopus 로고    scopus 로고
    • Color changes caused by conformational polymorphism: Optical- crystallography, single-crystal spectroscopy, and computational chemistry
    • DOI 10.1021/jp013019c
    • Yu L. 2002. Color changes by conformational polymorphism: Optical-crystallography, single-crystal spectroscopy, and computational chemistry. J. Phys. Chem. A 106:544-50 (Pubitemid 35264052)
    • (2002) Journal of Physical Chemistry A , vol.106 , Issue.3 , pp. 544-550
    • Yu, L.1
  • 53
    • 0034345221 scopus 로고    scopus 로고
    • Dealing with the impact of ritonavir polymorphs on the late stages of bulk drug process development
    • Chemburkar SR, Bauer J,Deming K, SpiwekH, Patel K, et al. 2000. Dealing with the impact of ritonavir polymorphs on the late stages of bulk drug process development. Org. Process Res. Dev. 4:413-17
    • (2000) Org. Process Res. Dev. , vol.4 , pp. 413-417
    • Chemburkar, S.R.1    Bauer, J.2    Deming, K.3    Spiwek, H.4    Patel, K.5
  • 54
    • 0026618802 scopus 로고
    • Kinetic study of the solid-state photolytic degradation of two polymorphic forms of furosemide
    • DOI 10.1016/0378-5173(92)90325-V
    • DeVilliersMM,van der Watt JG, LotterAP. 1992. Kinetic study of the solid-state photolytic degradation of two polymorphic forms of furosemide. Int. J. Pharm. 88:275-83 (Pubitemid 23000430)
    • (1992) International Journal of Pharmaceutics , vol.88 , Issue.1-3 , pp. 275-283
    • De Villiers, M.M.1    Van Der Watt, J.G.2    Lotter, A.P.3
  • 56
    • 0028273709 scopus 로고
    • Dehydration of theophylline monohydrate powder - Effects of particle size and sample weight
    • DOI 10.1016/0378-5173(94)90273-9
    • Agbada CO, York P. 1994. Dehydration of theophylline monohydrate powder: Effects of particle size and sample weight. Int. J. Pharm. 106:33-40 (Pubitemid 24110062)
    • (1994) International Journal of Pharmaceutics , vol.106 , Issue.1 , pp. 33-40
    • Agbada, C.O.1    York, P.2
  • 57
    • 77952394664 scopus 로고    scopus 로고
    • Polymorphism in acesulfame sweetener: Structureproperty and stability relationships of bending and brittle crystals
    • Velaga SP, Vangala VR,Basavoju S,Bostrom D. 2010. Polymorphism in acesulfame sweetener: Structureproperty and stability relationships of bending and brittle crystals. Chem. Commun. 2010:3562-64
    • (2010) Chem. Commun. , vol.2010 , pp. 3562-3564
    • Velaga, S.P.1    Vangala, V.R.2    Basavoju, S.3    Bostrom, D.4
  • 59
    • 33847721941 scopus 로고    scopus 로고
    • Polymorphisms and patent, market, and legal battles: Cefdinir case study
    • Cabri W,Ghett P, Giovanni P, AlpegianiM. 2007. Polymorphisms and patent, market, and legal battles: Cefdinir case study. Org. Process Res. Dev. 11:64-72
    • (2007) Org. Process Res. Dev. , vol.11 , pp. 64-72
    • Cabri, W.1    Ghett, P.2    Giovanni, P.3    Alpegiani, M.4
  • 60
    • 56249122895 scopus 로고    scopus 로고
    • Crystal polymorphism in antioxidant-metal deactivator 1,2-bis(3,5-di-tertbutyl- 4-hydroxyhydrocinnamoyl)hydrazine
    • Cogen JM, Hilmer AJ. 2008. Crystal polymorphism in antioxidant-metal deactivator 1,2-bis(3,5-di-tertbutyl- 4-hydroxyhydrocinnamoyl)hydrazine. Polym. Degrad. Stab. 93:2193-98
    • (2008) Polym. Degrad. Stab. , vol.93 , pp. 2193-2198
    • Cogen, J.M.1    Hilmer, A.J.2
  • 61
    • 77954533123 scopus 로고    scopus 로고
    • Polymorphism of Irganox 1076: Discovery of new forms and direct characterization of the polymorphs on a medical device by Raman microspectroscopy
    • Saunier J, Mazel V, Paris C, Yagoubi N. 2010. Polymorphism of Irganox 1076: Discovery of new forms and direct characterization of the polymorphs on a medical device by Raman microspectroscopy. Eur. J. Pharm. Biopharm. 75:443-50
    • (2010) Eur. J. Pharm. Biopharm. , vol.75 , pp. 443-450
    • Saunier, J.1    Mazel, V.2    Paris, C.3    Yagoubi, N.4
  • 62
    • 0009350760 scopus 로고
    • Pseudo-polymorphism and crystalline transition of magnesium stearate
    • Wada Y, Matsubara T. 1992. Pseudo-polymorphism and crystalline transition of magnesium stearate. Thermochim. Acta 196:63-84
    • (1992) Thermochim. Acta , vol.196 , pp. 63-84
    • Wada, Y.1    Matsubara, T.2
  • 63
    • 52149086340 scopus 로고    scopus 로고
    • The influence of lactose pseudopolymorphic form on salbutamol sulfate-lactose interactions in DPI formulations
    • TrainiD, Young PM, Thielmann F, Acharya M. 2008. The influence of lactose pseudopolymorphic form on salbutamol sulfate-lactose interactions in DPI formulations. Drug Dev. Ind. Pharm. 34:992-1001
    • (2008) Drug Dev. Ind. Pharm. , vol.34 , pp. 992-1001
    • Traini, D.1    Young, P.M.2    Thielmann, F.3    Acharya, M.4
  • 64
    • 77955915185 scopus 로고    scopus 로고
    • Strategies at the interface of drug discovery and development: Early optimization of the solid state phase and preclinical toxicology formulation for potential drug candidates
    • Palucki M, Higgins JD, Kwong E, Templeton AC. 2010. Strategies at the interface of drug discovery and development: Early optimization of the solid state phase and preclinical toxicology formulation for potential drug candidates. J. Med. Chem. 53:5897-905
    • (2010) J. Med. Chem. , vol.53 , pp. 5897-5905
    • Palucki, M.1    Higgins, J.D.2    Kwong, E.3    Templeton, A.C.4
  • 68
    • 77955364202 scopus 로고    scopus 로고
    • Process research and development of a MTP inhibitor: Another case of disappearing polymorph upon scale-up
    • Prashad M, Sutton P, Wu R, Hu B, Vivelo J, et al. 2010. Process research and development of a MTP inhibitor: Another case of disappearing polymorph upon scale-up. Org. Process. Res. Dev. 14:878-82
    • (2010) Org. Process. Res. Dev. , vol.14 , pp. 878-882
    • Prashad, M.1    Sutton, P.2    Wu, R.3    Hu, B.4    Vivelo, J.5
  • 69
    • 20444426340 scopus 로고    scopus 로고
    • A valuable technique for polymorph screening
    • Anderton C. 2004. A valuable technique for polymorph screening. Eur. Pharm. Rev. 9:68-74
    • (2004) Eur. Pharm. Rev. , vol.9 , pp. 68-74
    • Anderton, C.1
  • 71
    • 37949002445 scopus 로고    scopus 로고
    • Examining the range of methods available to derive numerous polymorphic forms
    • Maiwald M. 2006. Examining the range of methods available to derive numerous polymorphic forms. Am. Pharm. Rev. 9:95-99
    • (2006) Am. Pharm. Rev. , vol.9 , pp. 95-99
    • Maiwald, M.1
  • 76
    • 52449091248 scopus 로고    scopus 로고
    • Evaluation of hydrate screening methods
    • Cui Y, Yao E. 2008. Evaluation of hydrate screening methods. J. Pharm. Sci. 97:2730-44
    • (2008) J. Pharm. Sci. , vol.97 , pp. 2730-2744
    • Cui, Y.1    Yao, E.2
  • 78
    • 55549084893 scopus 로고    scopus 로고
    • Experimental methods in the study of thermodynamic polymorph stability relationships
    • Carlton RA. 2006. Experimental methods in the study of thermodynamic polymorph stability relationships. Am. Pharm. Rev. 9:88-93
    • (2006) Am. Pharm. Rev. , vol.9 , pp. 88-93
    • Carlton, R.A.1
  • 79
    • 0037168237 scopus 로고    scopus 로고
    • Application of slurry bridging experiments at controlled water activities to predict the solid-state conversion between anhydrous and hydrated forms using theophylline as a model drug
    • DOI 10.1016/S0378-5173(02)00277-6, PII S0378517302002776
    • Ticehurst MD, StoreyRA, Watt C. 2002. Application of slurry bridging experiments at controlled water activities to predict the solid-state conversion between anhydrous and hydrated forms using theophylline as a model compound. Int. J. Pharm. 247:1-10 (Pubitemid 35341134)
    • (2002) International Journal of Pharmaceutics , vol.247 , Issue.1-2 , pp. 1-10
    • Ticehurst, M.D.1    Storey, R.A.2    Watt, C.3
  • 80
    • 40649102167 scopus 로고    scopus 로고
    • Polymorph control: Past, present and future
    • Llinas A, Goodman JM. 2008. Polymorph control: Past, present and future. Drug Discov. Today 13:198-210
    • (2008) Drug Discov. Today , vol.13 , pp. 198-210
    • Llinas, A.1    Goodman, J.M.2
  • 81
    • 1042287180 scopus 로고    scopus 로고
    • Drug polymorphism and dosage form design: A practical perspective
    • DOI 10.1016/j.addr.2003.10.008
    • SinghalD, Curatolo W. 2004. Drug polymorphism and dosage form design: A practical perspective. Adv. Drug Deliv. Rev. 56:335-47 (Pubitemid 38201429)
    • (2004) Advanced Drug Delivery Reviews , vol.56 , Issue.3 , pp. 335-347
    • Singhal, D.1    Curatolo, W.2
  • 82
    • 85123271519 scopus 로고    scopus 로고
    • Alteration of the solid state of the drug substances: Polymorphs, solvates, and amorphous forms
    • ed. R Liu, Boca Raton, FL: CRC Press. 2nd ed.
    • Myrdal PB, Jozwiakowski MJ. 2008. Alteration of the solid state of the drug substances: Polymorphs, solvates, and amorphous forms. In Water-Insoluble Drug Formulation, ed. R Liu, pp. 531-66. Boca Raton, FL: CRC Press. 2nd ed.
    • (2008) Water-Insoluble Drug Formulation , pp. 531-566
    • Myrdal, P.B.1    Jozwiakowski, M.J.2
  • 83
    • 72449149140 scopus 로고    scopus 로고
    • A novel crystallization methodology to ensure isolation of the most stable crystal form
    • Cote A, Zhou G, Stanik M. 2009. A novel crystallization methodology to ensure isolation of the most stable crystal form. Org. Process Res. Dev. 13:1276-83
    • (2009) Org. Process Res. Dev. , vol.13 , pp. 1276-1283
    • Cote, A.1    Zhou, G.2    Stanik, M.3
  • 84
    • 0042520984 scopus 로고    scopus 로고
    • Automated measurement of metastable zones for pharmaceutical compounds
    • DOI 10.1205/026387603322150552
    • Parsons AR, Black SN,CollingR. 2003. Automatedmeasurement of metastable zones for pharmaceutical compounds. Chem. Eng. Res. Dev. 81:700-4 (Pubitemid 37002472)
    • (2003) Chemical Engineering Research and Design , vol.81 , Issue.6 , pp. 700-704
    • Parsons, A.R.1    Black, S.N.2    Colling, R.3
  • 85
    • 72449141474 scopus 로고    scopus 로고
    • A practical approach for using solubility to design cooling crystallizations
    • Muller FL, Fielding M, Black S. 2009. A practical approach for using solubility to design cooling crystallizations. Org. Process Res. Dev. 13:1315-21
    • (2009) Org. Process Res. Dev. , vol.13 , pp. 1315-1321
    • Muller, F.L.1    Fielding, M.2    Black, S.3
  • 86
    • 0034345203 scopus 로고    scopus 로고
    • Seeding the desired polymorph: Background, possibilities, limitations, and case studies
    • Beckmann W. 2000. Seeding the desired polymorph: Background, possibilities, limitations, and case studies. Org. Process Res. Dev. 4:372-83
    • (2000) Org. Process Res. Dev. , vol.4 , pp. 372-383
    • Beckmann, W.1
  • 87
    • 78649641378 scopus 로고    scopus 로고
    • Development of drug substances as mixture of polymorphs: Studies to control Form 3 in casopitant mesylate
    • Cimarosti Z, Castagnoli C, Rossetti M, Scarati M, Day C, et al. 2010. Development of drug substances as mixture of polymorphs: Studies to control Form 3 in casopitant mesylate. Org. Process. Res. Dev. 14:1337-46
    • (2010) Org. Process. Res. Dev. , vol.14 , pp. 1337-1346
    • Cimarosti, Z.1    Castagnoli, C.2    Rossetti, M.3    Scarati, M.4    Day, C.5
  • 88
    • 0032392648 scopus 로고    scopus 로고
    • Development of a seeding technique for the crystallization of the metastable A modification of abecarnil
    • Beckmann W, Nickisch K, Budde U. 1998. Development of a seeding technique for the crystallization of the metastable A modification of abecarnil. Org. Process Res. Dev. 2:298-304
    • (1998) Org. Process Res. Dev. , vol.2 , pp. 298-304
    • Beckmann, W.1    Nickisch, K.2    Budde, U.3
  • 90
    • 0038175334 scopus 로고    scopus 로고
    • Nucleation of one polymorph by another
    • DOI 10.1021/ja0351544
    • Yu L. 2003. Nucleation of one polymorph by another. J. Am. Chem. Soc. 125:6380-81 (Pubitemid 36605402)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.21 , pp. 6380-6381
    • Yu, L.1
  • 91
  • 92
    • 61449141154 scopus 로고    scopus 로고
    • Crystallization design space: Avoiding a hydrate in a water-based process
    • Black SN, Phillips A, Scott CI. 2009. Crystallization design space: Avoiding a hydrate in a water-based process. Org. Process Res. Dev. 13:78-83
    • (2009) Org. Process Res. Dev. , vol.13 , pp. 78-83
    • Black, S.N.1    Phillips, A.2    Scott, C.I.3
  • 94
    • 0001266165 scopus 로고
    • The kinetics of solvent-mediated phase transformation
    • Cardew PT, Davey RJ. 1985. The kinetics of solvent-mediated phase transformation. Proc. R. Soc. Lond. A 398:415-28
    • (1985) Proc. R. Soc. Lond. A , vol.398 , pp. 415-428
    • Cardew, P.T.1    Davey, R.J.2
  • 95
    • 79959482237 scopus 로고    scopus 로고
    • Wei C, Yang BS. 2006. U.S. Publication No. 2006/0160841
    • Wei C, Yang BS. 2006. U.S. Publication No. 2006/0160841
  • 96
    • 0030944392 scopus 로고    scopus 로고
    • Polymorphism in molecular crystals: Stabilization of a metastable form by conformational mimicry
    • DOI 10.1021/ja9626345, PII S0002786396026340
    • Davey RJ, Blagden N, Potts GD, Docherty R. 1997. Polymorphism in molecular crystals: Stabilization of a metastable form by conformational mimicry. J. Am. Chem. Soc. 119:1767-72 (Pubitemid 27145524)
    • (1997) Journal of the American Chemical Society , vol.119 , Issue.7 , pp. 1767-1772
    • Davey, R.J.1    Blagden, N.2    Potts, G.D.3    Docherty, R.4
  • 97
    • 0344583876 scopus 로고    scopus 로고
    • Inclusion of the Stable Form of a Polymorph within Crystals of Its Metastable Form
    • DOI 10.1021/cg034094a
    • Cashell C, SuttonD,CorcoranD,Hodnett BK. 2003. Inclusion of the stable form of a polymorph within crystals of its metastable form. Cryst. Growth Des. 3:869-72 (Pubitemid 37467737)
    • (2003) Crystal Growth and Design , vol.3 , Issue.6 , pp. 869-872
    • Cashell, C.1    Sutton, D.2    Corcoran, D.3    Hodnett, B.K.4
  • 100
    • 72449157428 scopus 로고    scopus 로고
    • Polymorphism in processes of crystallization in solution: A practical review
    • Mangin D, Puel F, Veesler S. 2009. Polymorphism in processes of crystallization in solution: A practical review. Org. Process Res. Dev. 13:1241-53
    • (2009) Org. Process Res. Dev. , vol.13 , pp. 1241-1253
    • Mangin, D.1    Puel, F.2    Veesler, S.3
  • 101
    • 77953151955 scopus 로고    scopus 로고
    • Mechanistic features of polymorphic transformations: The role of surfaces
    • Croker D, Hodnett BK. 2010. Mechanistic features of polymorphic transformations: The role of surfaces. Cryst. Growth Des. 10:2806-16
    • (2010) Cryst. Growth Des. , vol.10 , pp. 2806-2816
    • Croker, D.1    Hodnett, B.K.2
  • 102
    • 77956378312 scopus 로고    scopus 로고
    • Development of a targeted polymorph screening approach for a complex polymorphic and highly solvating API
    • Campeta AM, Chekal BP, Abramov YA, Meenan PA, Henson MJ, et al. 2010. Development of a targeted polymorph screening approach for a complex polymorphic and highly solvating API. J. Pharm. Sci. 99:3874-86
    • (2010) J. Pharm. Sci. , vol.99 , pp. 3874-3886
    • Campeta, A.M.1    Chekal, B.P.2    Abramov, Y.A.3    Meenan, P.A.4    Henson, M.J.5
  • 103
    • 78650038479 scopus 로고    scopus 로고
    • A thermodynamic-based approach to analyzing a highly solvating polymorphic system: The desolvation window method
    • Samas B, Seadeek C, Campeta AM, Chekal BP. 2011. A thermodynamic-based approach to analyzing a highly solvating polymorphic system: The desolvation window method. J. Pharm. Sci. 100:186-94
    • (2011) J. Pharm. Sci. , vol.100 , pp. 186-194
    • Samas, B.1    Seadeek, C.2    Campeta, A.M.3    Chekal, B.P.4
  • 106
    • 77956364064 scopus 로고    scopus 로고
    • Physical characterization of TRK-720 hydrate, the very late antigen-4 (VLA-4) inhibitor, as a solid form for inhalation: Preparation of the hydrate by solvent exchange among its solvates and mechanistical considerations
    • Shiraki M. 2010. Physical characterization of TRK-720 hydrate, the very late antigen-4 (VLA-4) inhibitor, as a solid form for inhalation: Preparation of the hydrate by solvent exchange among its solvates and mechanistical considerations. J. Pharm. Sci. 99:3986-4004
    • (2010) J. Pharm. Sci. , vol.99 , pp. 3986-4004
    • Shiraki, M.1
  • 107
    • 0035998944 scopus 로고    scopus 로고
    • Effects of mechanical processing on phase composition
    • DOI 10.1002/jps.10115
    • Brittain HG. 2002. Effects of mechanical processing on phase composition. J. Pharm. Sci. 91:1573-80 (Pubitemid 34680220)
    • (2002) Journal of Pharmaceutical Sciences , vol.91 , Issue.7 , pp. 1573-1580
    • Brittain, H.G.1
  • 109
    • 39149089987 scopus 로고    scopus 로고
    • Development and metrological characterization of quantitative X-ray diffraction phase analysis for the mixtures of clopidogrel bisulfate polymorphs
    • Uvarov V, Popov I. 2008. Development and metrological characterization of quantitative X-ray diffraction phase analysis for the mixtures of clopidogrel bisulfate polymorphs. J. Pharm. Bio. Anal. 46:676-82
    • (2008) J. Pharm. Bio. Anal. , vol.46 , pp. 676-682
    • Uvarov, V.1    Popov, I.2
  • 111
    • 51649125345 scopus 로고    scopus 로고
    • Crystallization and crystallinity of fluticasone propionate
    • Murnane D, Marriott C, Martin GP. 2008. Crystallization and crystallinity of fluticasone propionate. Cryst. Growth Des. 8:2753-64
    • (2008) Cryst. Growth Des. , vol.8 , pp. 2753-2764
    • Murnane, D.1    Marriott, C.2    Martin, G.P.3
  • 112
    • 47949124171 scopus 로고    scopus 로고
    • Polymorphic control of inhalation microparticles prepared by crystallization
    • Murnane D, Marriott C, Martin GP. 2008. Polymorphic control of inhalation microparticles prepared by crystallization. Int. J. Pharm. 361:141-49
    • (2008) Int. J. Pharm. , vol.361 , pp. 141-149
    • Murnane, D.1    Marriott, C.2    Martin, G.P.3
  • 114
    • 61749089521 scopus 로고    scopus 로고
    • Stability of solvates and packing systematics of nine crystal forms of the antipsychotic drug aripiprazole
    • BraunDE, Gelbrich T, Kahlenberg V, Tessadri R,Wieser J, et al. 2009. Stability of solvates and packing systematics of nine crystal forms of the antipsychotic drug aripiprazole. Cryst. Growth Des. 9:1054-65
    • (2009) Cryst. Growth Des. , vol.9 , pp. 1054-1065
    • Braun, D.E.1    Gelbrich, T.2    Kahlenberg, V.3    Tessadri, R.4    Wieser, J.5
  • 115
    • 79959455900 scopus 로고    scopus 로고
    • Casar R. 2010. U.S. Publication No. 2010/0016370
    • Casar R. 2010. U.S. Publication No. 2010/0016370
  • 122
    • 33846505562 scopus 로고    scopus 로고
    • On the polymorphism of aspirin: Crystalline aspirin as intergrowths of two "polymorphic" domains
    • DOI 10.1002/anie.200603373
    • Bond AD, Boese R, Desiraju GR. 2007. On the polymorphism of aspirin: Crystalline aspirin as intergrowths of two "polymorphic" domains. Angew. Chem. Int. Ed. 46:618-22 (Pubitemid 46159212)
    • (2007) Angewandte Chemie - International Edition , vol.46 , Issue.4 , pp. 618-622
    • Bond, A.D.1    Boese, R.2    Desiraju, G.R.3
  • 126
    • 57149141549 scopus 로고    scopus 로고
    • Evidence for a new crystalline phase of racemic ibuprofen
    • Dudognon E, Danede F, Descamps M, Correia NT. 2008. Evidence for a new crystalline phase of racemic ibuprofen. Pharm. Res. 25:2853-58
    • (2008) Pharm. Res. , vol.25 , pp. 2853-2858
    • Dudognon, E.1    Danede, F.2    Descamps, M.3    Correia, N.T.4
  • 128
    • 0010119028 scopus 로고
    • Hydration of drug molecules: Cavity inclusion of water in crystals of loperamide hydrochloride tetrahydrate
    • CairaMR, Gerber JJ, Lotter AP. 1995. Hydration of drug molecules: Cavity inclusion of water in crystals of loperamide hydrochloride tetrahydrate. Supramol. Chem. 5:225-30
    • (1995) Supramol. Chem. , vol.5 , pp. 225-230
    • Caira, M.R.1    Gerber, J.J.2    Lotter, A.P.3
  • 130
    • 8844256152 scopus 로고    scopus 로고
    • Characterization and solid-state transformations of the pseudopolymorphic forms of sodium naproxen
    • DOI 10.1021/cg049917q, Polymorphins in Crystals
    • Kim YS, Rousseau RW. 2004. Characterization and solid-state transformations of the pseudopolymorphic forms of sodium naproxen. Cryst. Growth Des. 4:1211-16 (Pubitemid 39532000)
    • (2004) Crystal Growth and Design , vol.4 , Issue.6 , pp. 1211-1216
    • Kim, Y.-S.1    Rousseau, R.W.2
  • 131
    • 77955329345 scopus 로고    scopus 로고
    • Characterization of solvates formed by sodium naproxen and an homologous series of alcohols
    • Chavez KJ, Guevara M, Rousseau RW. 2010. Characterization of solvates formed by sodium naproxen and an homologous series of alcohols. Cryst. Growth Des. 10:3372-77
    • (2010) Cryst. Growth Des. , vol.10 , pp. 3372-3377
    • Chavez, K.J.1    Guevara, M.2    Rousseau, R.W.3
  • 132
    • 33847705408 scopus 로고    scopus 로고
    • Polymorphic generation through solvent selection: Ranitidine hydrochloride
    • Trifkovic M, Rohani S. 2007. Polymorphic generation through solvent selection: Ranitidine hydrochloride. Org. Process Res. Dev. 11:138-43
    • (2007) Org. Process Res. Dev. , vol.11 , pp. 138-143
    • Trifkovic, M.1    Rohani, S.2


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