Pharmaceutical Co-Crystals
Tóm tắt
Từ khóa
Tài liệu tham khảo
Haleblian, 1975, Characterization of habits and crystalline modification of solids and their pharmaceutical applications, J Pharm Sci, 64, 1269, 10.1002/jps.2600640805
Walsh, 2003, Crystal engineering of the composition of pharmaceutical phases, Chem Commun, 186, 10.1039/b208574g
Fleischman, 2003, Crystal engineering of the composition of pharmaceutical phases: Multiple-component crystalline solids involving carbamazepine, Cryst Growth Des, 3, 909, 10.1021/cg034035x
McMahon, 2005, Crystal engineering of the composition of pharmaceutical phases 3. Primary amide supramolecular heterosynthons and their role in the design of pharmaceutical co-crystals, Z Kristallogr, 220, 340, 10.1524/zkri.220.4.340.61624
Almarsson, 2004, Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines?, Chem Commun, 1889, 10.1039/b402150a
Vishweshwar, 2005, Crystal engineering of pharmaceutical co-crystals from polymorphic active pharmaceutical ingredients, Chem Commun, 4601, 10.1039/b501304f
Remenar, 2003, Crystal engineering of novel cocrystals of a triazole drug with 1,4-dicarboxylic acids, J Am Chem Soc, 125, 8456, 10.1021/ja035776p
Morissette, 2004, High-throughput crystallization: Polymorphs, salts, co-crystals and solvates of pharmaceutical solids, Adv Drug Del Rev, 56, 275, 10.1016/j.addr.2003.10.020
Childs, 2004, Crystal engineering approach to forming cocrystals of amine hydrochlorides with organic acids. Molecular complexes of fluoxetine hydrochloride with benzoic, succinic, and fumaric acids, J Am Chem Soc, 126, 13335, 10.1021/ja048114o
Bettinetti, 2000, Structure and solid-state chemistry of anhydrous and hydrated crystal forms of the trimethoprim-sulfamethoxypyridazine 1:1 molecular complex, J Pharm Sci, 89, 478, 10.1002/(SICI)1520-6017(200004)89:4<478::AID-JPS5>3.0.CO;2-5
Zerkowski, 1997, Polymorphic packing arrangements in a class of engineered organic crystals, Chem Mat, 9, 1933, 10.1021/cm9505660
Almarsson, 2003, High-throughput surveys of crystal form diversity of highly polymorphic pharmaceutical compounds, Cryst Growth Des, 3, 927, 10.1021/cg034058b
Datta, 2004, Crystal structure of drugs: Advances in determination, prediction and engineering, Nat Rev Drug Discov, 3, 42, 10.1038/nrd1280
Oswald, 2002, The formation of paracetamol (acetaminophen) adducts with hydrogen-bonded acceptors, Acta Crystallogr, B58, 1057, 10.1107/S0108768102015987
Trask, 2004, Solvent-drop grinding: Green polymorph control of cocrystallization, Chem Commun, 890, 10.1039/b400978a
Trask, 2005, Pharmaceutical cocrystallization: Engineering a remedy for caffeine hydration, Cryst Growth Des, 5, 1013, 10.1021/cg0496540
Ling, 1893, Halogen derivatives of quinone Part III. Derivatives of quinhydrone, J Chem Soc, 63, 1314, 10.1039/CT8936301314
Kitaigorodskii, 1984
Aakeröy, 2005, Building co-crystals with molecular sense and supramolecular sensibility, Cryst Eng Comm, 7, 439, 10.1039/b505883j
Bernstein, 2005, …And another comment on Pseudopolymorphism, Cryst Growth Des, 5, 1661, 10.1021/cg058007l
Nangia, 2005, Pseudopolymorph: Retain this widely accepted term, Cryst Growth Des, 5
Buck, 1931, Mixed benzoins VI. Further examples of reversibility. The formation of addition compounds, J Am Chem Soc, 53, 2784, 10.1021/ja01358a052
Remyga, 1969, Examples of mixed binary molecular crystal with double statistical disorder in the arrangement of molecules, Z Strukturnoi Khimii, 10, 1131
Van Niekerk, 1948, The crystal structure of the molecular complex of 4,4′-dinitrobiphenyl with biphenyl, Acta Crystallogr, 1, 44, 10.1107/S0365110X48000107
Hall, 1967, 2:1 solid-state complex of hexamethylbenzene:tetracyanoethylene, J Phys Chem, 71, 465, 10.1021/j100861a051
Pekker, 2005, Rotor-stator molecular crystals of fullerenes and cubane, Nature Mat, 4, 764, 10.1038/nmat1468
Allen, 1993, 3D Search and research using the Cambridge Structural Database, Chem Des Automat News, 8, 31
Huang, 1997, A novel class of phenol-pyridine co-crystals for second harmonic generation, J Mater Chem, 7, 713, 10.1039/a604311j
Gao, 2004, Supramolecular construction of molecular ladders in the solid state, Angew Chem Int Ed, 43, 232, 10.1002/anie.200352713
Xiao, 2000, A supramolecular solution to a long-standing problem: The 1,6-polymerization of a triacetylene, Angew Chem Int Ed, 39, 2132, 10.1002/1521-3773(20000616)39:12<2132::AID-ANIE2132>3.0.CO;2-8
Ma, 2002, Structural variation and supramolecular isomerism in the C-Methylcalix[4]resorcinarene/bipyridine system, Cryst Growth Des, 2, 7, 10.1021/cg0155595
MacGillivray, 2001, Conformational isomerism leads to supramolecular isomerism and nanoscale inclusion in 2D extended framework solids based on C-methylcalix[4]resorcinarene, Chem Commun, 1034, 10.1039/b102856c
MacGillivray, 2000, Encapsulation of two aromatics by a carcerand-like capsule of nanometer-scale dimension, Chem Commun, 359, 10.1039/a909339g
Taylor, 1994, Process and composition for use in photographic materials containing hydroquinones
Pepinsky, 1955, Crystal engineering: New concepts in crystallography, Phys Rev, 100, 971
Schmidt, 1971, Photodimerization in the solid state, Pure Appl Chem, 27, 647, 10.1351/pac197127040647
Desiraju, 1989
Lehn, 1995
Moulton, 2001, From molecules to crystal engineering: Supramolecular isomerism and polymorphism in networks, Chem Rev, 101, 1629, 10.1021/cr9900432
Zaworotko, 2001, Superstructural diversity in two dimensions: Crystal engineering of laminated solids, Chem Commun, 1, 10.1039/b007127g
Eddaoudi, 2001, Modular chemistry: Secondary building units as a basis for the design of highly porous and robust metal-organic carboxylate frameworks, Acc Chem Res, 34, 319, 10.1021/ar000034b
Kitagawa, 2004, Functional porous coordination polymers, Angew Chem Int Ed, 43, 2334, 10.1002/anie.200300610
Janiak, 2003, Engineering coordination polymers towards applications, J Chem Soc Dalton Trans, 14, 2781, 10.1039/b305705b
Oh, 2003, A novel 3D brick-wall coordination network based on nodes with square-pyramidal connectivity, Angew Chem Int Ed, 42, 2026, 10.1002/anie.200250637
Braga, 1998, Crystal engineering and organometallic architecture, Chem Rev, 98, 1375, 10.1021/cr960091b
Hosseini, 2003, Molecular tectonics: From molecular recognition of anions to molecular networks, Coord Chem Rev, 240, 157, 10.1016/S0010-8545(03)00021-3
Melendez, 1998, Hydrogen-bonded ribbons, tapes and sheets as motifs for crystal engineering, Top Curr Chem, 198, 97, 10.1007/3-540-69178-2_3
Desiraju, 1995, Supramolecular synthons in crystal engineering—A new organic synthesis, Angew Chem Int Ed, 34, 2311, 10.1002/anie.199523111
Allen, 1983, Systematic analysis of structural data as a research technique in organic chemistry, Acc Chem Res, 16, 146, 10.1021/ar00089a001
Leiserowitz, 1976, Molecular packing modes. Carboxylic acids, Acta Crystallogr Section B, 32, 775, 10.1107/S0567740876003968
Bernstein, 1994, The role of hydrogen bonding in molecular assemblies, 431
Kuduva, 1999, Cubanecarboxylic acids. Crystal engineering considerations and the role of C═H···O hydrogen bonds in determining O═H···O networks, J Am Chem Soc, 121, 1936, 10.1021/ja981967u
http://www.rxlist.com/top200.htm. 30 of the top 100 selling drugs in the U.S. in 2002 contain carboxylic acids.
Allen, 1999, Systematic analysis of the probabilities of formation of bimolecular hydrogen-bonded ring motifs in organic crystal structures, New J Chem, 23, 25, 10.1039/a807212d
Steiner, 2001, Competition of hydrogen-bonded acceptors for the strong carboxyl donors, Acta Crystallogr, B57, 103, 10.1107/S0108768100014348
Sharma, 1996, X-ray structure of C6H3(CO2H)3-1,3,5·1.5(4,4′-bipy): A ‘super trimesic acid’ chicken-wire grid, Chem Commun, 2655, 10.1039/CC9960002655
Vishweshwar, 2002, Recurrence of carboxylic acid-pyridine supramolecular synthon in the crystal structures of some pyrazinecarboxylic acids, J Org Chem, 67, 556, 10.1021/jo0162484
Vishweshwar, 2003, Molecular complexes of homologous alkanedicarboxylic acids with isonicotinamide: X-ray crystal structures, hydrogen bond synthons, and melting point alternation, Cryst Growth Des, 3, 783, 10.1021/cg034037h
Bhogala, 2002, Fourfold inclined interpenetrated and threefold parallel interpenetrated hydrogen bonds networks in 1,3,5-cyclohexane tricarboxylic acid hydrate and its molecular complex with 4,4′-bipyridine, Cryst Growth Des, 2, 325, 10.1021/cg025537y
Aakeröy, 2002, A high-yielding supramolecular reaction, J Am Chem Soc, 124, 14425, 10.1021/ja027845q
Aakeröy, 2001, “Total synthesis” supramolecular style: Design and hydrogen-bond-directed assembly of ternary supermolecules, Angew Chem Int Ed, 40, 3240, 10.1002/1521-3773(20010903)40:17<3240::AID-ANIE3240>3.0.CO;2-X
Bhogala, 2003, Co-crystals of 1,3,5-cyclohexanetricarboxylic acid with 4,4′-bipyridine homologues: Acid···Pyridine hydrogen bonding in neutral and ionic complexes, Cryst Growth Des, 3, 547, 10.1021/cg034047i
Bond, 2003, In situ co-crystallization as a tool for low-temperature crystal engineering, Chem Commun, 250, 10.1039/b208904a
Ma, 2003, Formation of pyrene nano-rods within a supramolecular framework, Chem Commun, 2290, 10.1039/b306965f
Harkema, 1972, The crystal structure of urea oxalic acid (2:1), Acta Crystallogr B, 28, 1646, 10.1107/S0567740872004789
Leiserowitz, 1977, The molecule packing modes and the hydrogen-bonding properties of amide-dicarboxylic acid complexes, Acta Crystallogr, B33, 2719, 10.1107/S0567740877009376
Reddy, 2004, Phenyl-perfluorophenyl synthon mediated cocrystallization of carboxylic acids and amides, Cryst Growth Des, 4, 89, 10.1021/cg034106s
Aakeröy, 2003, Do polymorphic compounds make good cocrystallizing agents? A structural case study that demonstrates the importance of synthon flexibility, Cryst Growth Des, 3, 159, 10.1021/cg025593z
Ermer, 1994, Molecular recognition among alcohols and amines: Super-tetrahedral crystal architectures of linear diphenol–diamine complexes and aminophenols, J Chem Soc Perkin Trans, 2, 925, 10.1039/P29940000925
Hanessian, 2003, Crystal design: Structure and function, 77
Vangala, 2003, Correspondence between molecular functionality and crystal structures. Supramolecular chemistry of a family of homologated aminophenols, J Am Chem Soc, 125, 14495, 10.1021/ja037227p
Vishweshwar, 2003, Supramolecular synthons in phenol-isonicotinamide adducts, Cryst Eng Comm, 5, 164, 10.1039/B304078J
Papaefstathiou, 2001, Discrete versus infinite molecular self-assembly: Control in crystalline hydrogen-bonded assemblies based on resorcinol, Org Lett, 3, 3835, 10.1021/ol0165948
Biradha, 1998, A supramolecular analogue of cyclohexane sustained by aromatic C═H···π interactions: Complexes of 1,3,5-trihydroxybenzene with substituted pyridines, J Am Chem Soc, 120, 6431, 10.1021/ja974105m
Trask, 2005, Crystal engineering of organic cocrystals by the solid-state grinding approach, Top Curr Chem, 254, 41, 10.1007/b100995
Shan, 2002, Mechanochemistry and co-crystal formation: Effect of solvent on reaction kinetics, Chem Commun, 2372, 10.1039/b207369m
Trask, 2005, Selective polymorph transformation via solvent-drop grinding, Chem Commun, 880, 10.1039/b416980h
Stahl, 2002, Pharmaceutical aspects of the drug salt form
Remenar, 2003, Salt selection and simultaneous polymorphism assessment via high-throughput crystallization: The case sertraline, Org Process Res Dev, 7, 990, 10.1021/op034115+
Bhogala, 2005, Three-component carboxylic acid-bipyridine lattice inclusion host. Supramolecular synthesis of ternary cocrystals, Cryst Growth Des, 5, 1683, 10.1021/cg058012p
McCrone, 1965, Physics and chemistry of the solid state, 725
These statistics are solely based on the structures deposited in the CSD. There are also other hydrate and polymorphic single component and co-crystals that are not characterized through X-ray diffraction or not deposited in the CSD.
Bernstein, 2002
Bernsein, 1999, Concomitant polymorphs, Angew Chem Int Ed, 38, 3440, 10.1002/(SICI)1521-3773(19991203)38:23<3440::AID-ANIE3440>3.0.CO;2-#
Byrn, 1999
Vishweshwar, 2006, Crystal engineering of pharmaceutical co-crystals, 25
Guttman, 1955, Study of possible complex formation between macromolecules and certain pharmaceuticals IX. Formation of iodine-iodide complexes with polyethylene glycol, J Am Pharm Asso, 44, 668, 10.1002/jps.3030441108
Guttman, 1956, Possible complex formation between macromolecules and certain pharmaceuticals X. The interaction of some phenolic compounds with polyethylene glycols, polypropylene glycols, and polyvinylpyrrolidone, J Am Pharm Asso, 45, 659, 10.1002/jps.3030451002
Zerkowski, 1990, Design of organic structures in the solid state: Hydrogen-bonded molecular “Tapes”, J Am Chem Soc, 112, 9025, 10.1021/ja00180a083
Zerkowski, 1992, Solid-state structures of “Rosette” and “Crinkled Tape” motifs derived from the cyanuric acid-melamine lattice, J Am Chem Soc, 114, 5473, 10.1021/ja00039a096
Zerkowski, 1994, Steric control of secondary, solid-state architecture in 1:1 complexes of melamines and barbiturates that crystallize as crinckled tapes, J Am Chem Soc, 116, 4298, 10.1021/ja00089a019
Zerkowski, 1994, Design of organic structures in the solid state: Molecular tapes based on the network of hydrogen bonds present in the cyanuric acid·melamine complex, J Am Chem Soc, 116, 2382, 10.1021/ja00085a018
Zerkowski, 1994, New varities of crystlline archeticture produced by small changes in molecular structure in tape complexes of melamines and barbiturates, J Am Chem Soc, 116, 4305, 10.1021/ja00089a020
Vishweshwar, 2002, Supramolecular synthons based on N═H···N and C═H···O hydrogen bonds. Crystal engineering of a helical structure with 5,5-diethylbarbituric acid, Chem Commun, 1830, 10.1039/B204388B
Himes, 1981, Structure of carbamazepine: 5H-dibenz[b,f]azepine-5-carboxamide, Acta Crystallogr, B37, 2242, 10.1107/S0567740881008522
Reboul, 1981, 5H-dibenz[b,f]axepine-5-carboxamide (carbamazepine), Acta Crystallogr, B37, 844
Lowes, 1987, Physicochemical properties and X-ray structural studies of the trigonal polymorph of carbamazepine, J Pharm Sci, 76, 744, 10.1002/jps.2600760914
Lisgarten, 1989, Crystal and molecular structure of 5-carbamyl-5H-dibenz[b,f]azepine, J Crystallogr Spectrosc Res, 19, 641, 10.1007/BF01179836
Rustichelli, 2000, Solid-state study of polymorphic drugs: Carbamazepine, J Pharm Biomed Anal, 23, 41, 10.1016/S0731-7085(00)00262-4
Ceolin, 1997, X-ray characterization of the triclinic polymorph of carbamazepine, J Pharm Sci, 86, 1062, 10.1021/js960338k
Grzesiak, 2003, Comparison of the four anhydrous polymorphs of carbamazepine and crystal structure of form 1, J Pharm Sci, 92, 2260, 10.1002/jps.10455
Reck, 1986, The order-disorder structure of carbamazepine dihydrate: 5H-dibenz[b,f]azepine-5-carboxamide dihydrate, C15H12N2O·2H2O, Cryst Res Technol, 21, 1463, 10.1002/crat.2170211118
Reck, 1991, Crystal structures of the adducts carbamazepine-ammonium chloride and carbamazepine-ammonium bromide and their transformation to carbamazepine dihydrate, Pharmazie, 46, 509
Kobayashi, 2000, Physicochemical properties and bioavailability of carbamazepine polymorphs and dihydrate, Int J Pharm, 193, 137, 10.1016/S0378-5173(99)00315-4
Leiserowitz, 1969, Molecular packing modes III. Primary amides, J Chem Soc, A16, 2372, 10.1039/j19690002372
MacDonald, 2000, The role of amides in the non-covalent synthesis of supramolecular structures in solution, at interfaces and in solids, 291
Meléndez, 1998, Hydrogen-bonded ribbons, tapes and sheets as motifs for crystal engineering, 97
Rodriguez-Spong, 2003, Enhancing the pharmaceutical behavior of carbamazepine through the formation of cocrystals, AAPS Pharm Sci, 5
Rodriguez-Spong, 2005
Scheuer, 1999, Piracetam improves cognitive performance by restoring neurochemical deficits of the aged rat brain, Pharmacopsychiatry, 32, 10, 10.1055/s-2007-979231
Gouliaev, 1994, Piracetam and other structurally related nootropics, Brain Res Rev, 19, 180, 10.1016/0165-0173(94)90011-6
Tacconi, 1986, Piracetam: Physiological disposition and mechanism of action, 675
Giurgea, 1967, A GABA-related hypothesis on the mechanism of action of the antimotion sickness drugs, Arch Int Pharmacodyn, 166, 238
Admiraal, 1982, Structures of the triclinic and monoclinic modifications of (2-oxo-1-pyrrolidinyl)acetamide, Acta Crystallogr, B38, 2600, 10.1107/S0567740882009431
Louer, 1995, Structure of metastable phase of piracetam from X-ray powder diffraction using the atom-atom potential method, Acta Crystallogr, B51, 182, 10.1107/S0108768194008840
Fabbiani, 2005, An exploration of the polymorphism of piracetam using high pressure, Cryst Eng Comm, 7, 179, 10.1039/b418976k
Kuhnert-Brandstaetter, 1994, Stability behavior of piracetam polymorphs, Scientia Pharm, 62, 307
Lorico, 1986, Gentisic acid: An aspirin metabolite with multiple effects on human blood polymorphonuclear leukocytes, Biochem Pharma, 35, 2443, 10.1016/0006-2952(86)90474-0
Ohsako, 1995, Effect of aspirin metabolites on pharmacokinetics of aspirin in human blood, Yakuzai, 55, 261
Cunha, 2001, The mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: The role of potassium channels and vasoactive intestinal peptide receptors, Brazilian J Med Bio Res, 34, 381, 10.1590/S0100-879X2001000300013
Haisa, 1982, The structures of 2-hydroxy-5-methylbenzoic acid and dimorphs of 2,5-dihydroxybenzoic acid, Acta Crystallogr, B38, 1480, 10.1107/S0567740882006189
Luo, 2002, Engineering crystalline architecture with supramolecular tapes: Studies on secondary donor–acceptor interactions in cocrystals of the cyclic dipeptide of glycine, Cryst Growth Des, 2, 337, 10.1021/cg025535d
Aäkeroy, 1995, L-proline 2,5-dihydroxybenzoic acid (1/1):a zwitterion co-crystal, Acta Chem Scand, 49, 762, 10.3891/acta.chem.scand.49-0762
Mele, 2000, Noncovalent association phenomena of 2,5-dihydroxybenzoic acid with cyclic and liner oligosaccharides. A matrix-assisted laster desorption/ionization time-of-flight mass spectrometric and X-ray crystallographic study, J Am Soc Mass Spectrum, 11, 228, 10.1016/S1044-0305(99)00143-9
Refcodes: AJALAY, FURAOX, NEMTEE, RAHGEM, UNEZIW, UNEZOC, UNEZUI, UROXAM, XEWTIC and ZODWIY.
Hickey MB,Peterson ML,Scoppettuolo L,Vetter A,Guzmán H,Remenar JF,McMahon JA,Tawa MD,Almarsson Ö.Performance comparison of a novel co-crystal of carbamazepine with polymorphs and dihydrate forms. Private communication.
Giuseppetti, 1994, 1:1 Molecular complex of trimethoprim and sulfametrole, Acta Crystallogr, C50, 1289
Ishida, 1989, Structural study of histamine H2-receptor antagonists. Five 3-[2-(diaminomethyleneamino)-4-thiazolylmethylthio] propionamidine and amide derivatives, Acta Crystallogr, B45, 505, 10.1107/S0108768189006634
Caira, 1998, Structure of a 1:1 complex between the anthelmintic drug mebendazole and propionic acid, J Chem Crystallogr, 28, 11, 10.1023/A:1021766300133
Ladányi, 1999, Stereochemistry and enantiomeric purity of a novel anxiolytic agent, deramciclane fumarate, Chirality, 11, :689, 10.1002/(SICI)1520-636X(1999)11:9<689::AID-CHIR4>3.0.CO;2-X
Ota, 1993, Conformational studies of semotiadil (Sd-3211), A Novel Ca2+ Antagonist, Chem Pharm Bull, 41, 1681, 10.1248/cpb.41.1681
Marubayashi, 1999, Crystal structure of 1-{2-[(p-chloro-alpha-phenylbenzyl)oxy]ethyl}piperidine fendizoate (Cloperastine fendizoate), Anal Sci, 15, 813, 10.2116/analsci.15.813
Hogberg, 1987, Crystallographic, theoretical and molecular modeling studies on the conformations of the salicylamide, raclopride, a selective dopamine-D2 antagonist, J Pharm Pharmacol, 39, 787, 10.1111/j.2042-7158.1987.tb05120.x