Disappearing Polymorphs Revisited

被引:319
作者
Bucar, Dejan-Kresimir [1 ]
Lancaster, Robert W. [1 ]
Bernstein, Joel [2 ,3 ,4 ]
机构
[1] UCL, Dept Chem, London WC1H 0AJ, England
[2] New York Univ Abu Dhabi, Fac Nat Sci, Abu Dhabi, U Arab Emirates
[3] New York Univ Shanghai, Pudong New Area, Shanghai 200122, Peoples R China
[4] Ben Gurion Univ Negev, Dept Chem, IL-84120 Beer Sheva, Israel
关键词
crystallization; drug formulation; nucleation; polymorphism; solid-state chemistry; CRYSTAL-STRUCTURE PREDICTION; SMALL ORGANIC-MOLECULES; SOLID-STATE; PHARMACEUTICAL COCRYSTALS; LUMINESCENT PROPERTIES; CO-CRYSTALS; RANITIDINE HYDROCHLORIDE; ELECTRONIC-STRUCTURE; BLIND TEST; ACID;
D O I
10.1002/anie.201410356
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Nearly twenty years ago, Dunitz and Bernstein described a selection of intriguing cases of polymorphs that disappear. The inability to obtain a crystal form that has previously been prepared is indeed a frustrating and potentially serious problem for solid-state scientists. This Review discusses recent occurrences and examples of disappearing polymorphs (as well as the emergence of elusive crystal forms) to demonstrate the enduring relevance of this troublesome, but always captivating, phenomenon in solid-state research. A number of these instances have been central issues in patent litigations. This Review, therefore, also highlights the complex relationship between crystal chemistry and the law.
引用
收藏
页码:6972 / 6993
页数:22
相关论文
共 141 条
[1]   Investigation of the riddle of sulfathiazole polymorphism [J].
Abu Bakar, Mohd R. ;
Nagy, Zoltan K. ;
Rielly, Chris D. ;
Dann, Sandy E. .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2011, 414 (1-2) :86-103
[2]  
Almarsson Ö, 2012, PHARM PAT ANAL, V1, P313, DOI [10.4155/ppa.12.29, 10.4155/PPA.12.29]
[3]  
[Anonymous], ANGEW CHEM
[4]  
[Anonymous], ANGEW CHEM
[5]  
[Anonymous], 2008, Angewandte Chemie
[6]  
[Anonymous], 1995, ANGEW CHEM
[7]  
BABILEV FV, 1987, KHIM FARM ZH+, V21, P1275
[8]   MOLECULAR-CONFORMATION AND ELECTRONIC-STRUCTURE .6. THE STRUCTURE OF P-METHYL-N-(P-METHYLBENZYLIDENE)ANILINE (FORM-I) [J].
BAR, I ;
BERNSTEIN, J .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1982, 38 (JAN) :121-125
[9]   Towards crystal structure prediction of complex organic compounds - a report on the fifth blind test [J].
Bardwell, David A. ;
Adjiman, Claire S. ;
Arnautova, Yelena A. ;
Bartashevich, Ekaterina ;
Boerrigter, Stephan X. M. ;
Braun, Doris E. ;
Cruz-Cabeza, Aurora J. ;
Day, Graeme M. ;
Della Valle, Raffaele G. ;
Desiraju, Gautam R. ;
van Eijck, Bouke P. ;
Facelli, Julio C. ;
Ferraro, Marta B. ;
Grillo, Damian ;
Habgood, Matthew ;
Hofmann, Detlef W. M. ;
Hofmann, Fridolin ;
Jose, K. V. Jovan ;
Karamertzanis, Panagiotis G. ;
Kazantsev, Andrei V. ;
Kendrick, John ;
Kuleshova, Liudmila N. ;
Leusen, Frank J. J. ;
Maleev, Andrey V. ;
Misquitta, Alston J. ;
Mohamed, Sharmarke ;
Needs, Richard J. ;
Neumann, Marcus A. ;
Nikylov, Denis ;
Orendt, Anita M. ;
Pal, Rumpa ;
Pantelides, Constantinos C. ;
Pickard, Chris J. ;
Price, Louise S. ;
Price, Sarah L. ;
Scheraga, Harold A. ;
van de Streek, Jacco ;
Thakur, Tejender S. ;
Tiwari, Siddharth ;
Venuti, Elisabetta ;
Zhitkov, Ilia K. .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2011, 67 :535-551
[10]  
Barnes R. D., 1988, Anti-depressant crystalline paroxetine hydrochloride hemihydrate, Patent No. [US4721723A, 4721723]