Polymorphism in cocrystals: a review and assessment of its significance

被引:255
作者
Aitipamula, Srinivasulu [1 ]
Chow, Pui Shan [1 ]
Tan, Reginald B. H. [1 ,2 ]
机构
[1] ASTAR, Inst Chem & Engn Sci, Singapore 627833, Singapore
[2] Natl Univ Singapore, Dept Chem & Biomol Engn, Singapore 117576, Singapore
关键词
DISSOLVING EUTECTIC COMPOSITIONS; CRYSTAL-STRUCTURE PREDICTION; MULTIPLE-COMPONENT CRYSTALS; ACID CO-CRYSTALS; PHARMACEUTICAL COCRYSTALS; CONFORMATIONAL POLYMORPHISM; PHYSICOCHEMICAL PROPERTIES; TAUTOMERIC POLYMORPHISM; CONCOMITANT POLYMORPHS; 4-HYDROXYBENZOIC ACID;
D O I
10.1039/c3ce42008f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cocrystals have gained much interest in recent years owing to their potential to improve the physicochemical properties of the parent compounds. It was once thought that cocrystals could be a means to prevent polymorphism but many recent examples of cocrystal polymorphism have been discovered and reported. Similar to single component crystals, polymorphs of cocrystals can display significantly different properties. In this contribution, we present a survey of polymorphic cocrystals. The different types of polymorphs, namely synthon, conformational, packing, and tautomeric, are identified and discussed with representative examples. In addition, polymorphs of cocrystals that showed distinct physicochemical properties are highlighted.
引用
收藏
页码:3451 / 3465
页数:15
相关论文
共 154 条
[31]  
Blagden N., 1998, J CHEM SOC FARADAY T, P94
[32]   The imide tautomer of sulfasalazine [J].
Blake, AJ ;
Lin, X ;
Schröder, M ;
Wilson, C ;
Yuan, RX .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2004, 60 :O226-O228
[33]   Celecoxib cocrystal polymorphs with cyclic amides: synthons of a sulfonamide drug with carboxamide coformers [J].
Bolla, Geetha ;
Mittapalli, Sudhir ;
Nangia, Ashwini .
CRYSTENGCOMM, 2014, 16 (01) :24-27
[34]   What is a co-crystal? [J].
Bond, Andrew D. .
CRYSTENGCOMM, 2007, 9 (09) :833-834
[35]   The 1:1 adduct of triphenylsilanol and 4,4′-bipyridyl, and three pairwise-concomitant triclinic polymorphs of the 4:1 adduct having Z′ = 0.5, 1 and 4 [J].
Bowes, KF ;
Ferguson, G ;
Lough, AJ ;
Glidewell, C .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2003, 59 (02) :277-286
[36]   Three Polymorphic Forms of the Co-Crystal 4,4′-Bipyridine/Pimelic Acid and their Structural, Thermal, and Spectroscopic Characterization [J].
Braga, Dario ;
Palladino, Giuseppe ;
Polito, Marco ;
Rubini, Katia ;
Grepioni, Fabrizia ;
Chierotti, Michele R. ;
Gobetto, Roberto .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (32) :10149-10159
[37]  
Brittain H. G., 1999, POLYMORPHISM PHARM S
[38]   Cocrystal Systems of Pharmaceutical Interest: 2011 [J].
Brittain, Harry G. .
CRYSTAL GROWTH & DESIGN, 2012, 12 (11) :5823-5832
[39]   THE STRUCTURES OF POLYMORPH-I AT 181-K AND POLYMORPH-II AT 297-K OF THE BIS(WATER-DICHLOROPICRIC ACID)-1,4,7,10,13,16-HEXAOXACYCLOOCTADECANE COMPLEX, 2[H2O.C6(NO2)3CL2(OH)].(CH2CH2O)6 [J].
BRITTON, D ;
CHANTOONI, MK ;
KOLTHOFF, IM .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1988, 44 :303-306
[40]   Polymorphism in co-crystals: a metastable form of the ionic co-crystal 2 HBz•1 NaBz crystallised by flash evaporation [J].
Butterhof, Christian ;
Baerwinkel, Kilian ;
Senker, Juergen ;
Breu, Josef .
CRYSTENGCOMM, 2012, 14 (20) :6744-6749