Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines?

The evolution of crystal engineering into a form of supramolecular synthesis is discussed in the context of problems and opportunities in the pharmaceutical industry. Specifically, it has become clear that a wide array of multiple component pharmaceutical phases, so called pharmaceutical co-crystals, can be rationally designed using crystal engineering, and the strategy affords new intellectual property and enhanced properties for pharmaceutical substances.

[1]  Michael J Cima,et al.  High-throughput crystallization: polymorphs, salts, co-crystals and solvates of pharmaceutical solids. , 2004, Advanced drug delivery reviews.

[2]  A. Matzger,et al.  Comparison of the four anhydrous polymorphs of carbamazepine and the crystal structure of form I. , 2003, Journal of pharmaceutical sciences.

[3]  Orn Almarsson,et al.  Crystal engineering of novel cocrystals of a triazole drug with 1,4-dicarboxylic acids. , 2003, Journal of the American Chemical Society.

[4]  A. Beatty,et al.  A high-yielding supramolecular reaction. , 2002, Journal of the American Chemical Society.

[5]  V. Lynch,et al.  Recurrence of carboxylic acid-pyridine supramolecular synthon in the crystal structures of some pyrazinecarboxylic acids. , 2002, The Journal of organic chemistry.

[6]  T. Steiner The hydrogen bond in the solid state. , 2002, Angewandte Chemie.

[7]  A. Beatty,et al.  "Total Synthesis" Supramolecular Style: Design and Hydrogen-Bond-Directed Assembly of Ternary Supermolecules. , 2001, Angewandte Chemie.

[8]  Y. Yamashita,et al.  Crystal engineering using anilic acids and dipyridyl compounds through a new supramolecular synthon. , 2001, The Journal of organic chemistry.

[9]  Y. Ito,et al.  In situ X-ray observation of pedal-like conformational change and dimerization of trans-cinnamamide in cocrystals with phthalic acid. , 2001, Journal of the American Chemical Society.

[10]  S. Byrn,et al.  Chemical reactivity in solid-state pharmaceuticals: formulation implications. , 2001, Advanced drug delivery reviews.

[11]  M. Zaworotko,et al.  From molecules to crystal engineering: supramolecular isomerism and polymorphism in network solids. , 2001, Chemical reviews.

[12]  Graham Smith,et al.  Molecular Cocrystals of Aromatic Carboxylic Acids with Unsymmetrically Substituted Ureas. The Structures of Phenylurea and the 1 : 1 Adducts of Phenylurea with a Series of Nitro-Substituted Acids , 2000 .

[13]  S. Ohba,et al.  Compelled Orientational Control of the Solid-State Photodimerization of trans-Cinnamamides: Dicarboxylic Acid as a Non-covalent Linker , 2000 .

[14]  J. White,et al.  Molecular Cocrystals of Aromatic Carboxylic Acids with 1,1-Diethylurea: Synthesis and the Crystal Structures of a Series of Nitro-Substituted Analogues , 2000 .

[15]  Bruno C. Hancock,et al.  What is the True Solubility Advantage for Amorphous Pharmaceuticals? , 2000, Pharmaceutical Research.

[16]  B. Shekunov,et al.  CRYSTALLIZATION PROCESSES IN PHARMACEUTICAL TECHNOLOGY AND DRUG DELIVERY DESIGN , 2000 .

[17]  M. Caira,et al.  Structure and solid-state chemistry of anhydrous and hydrated crystal forms of the trimethoprim-sulfamethoxypyridazine 1:1 molecular complex. , 2000, Journal of pharmaceutical sciences.

[18]  S. Itai,et al.  Physicochemical properties and bioavailability of carbamazepine polymorphs and dihydrate. , 2000, International journal of pharmaceutics.

[19]  D. Braga,et al.  Crystal Engineering and Organometallic Architecture. , 1998, Chemical reviews.

[20]  C. Rao,et al.  Unexpected isomerization of maleic acid to fumaric acid on co-crystallization with 4,4′-bipyridine , 1998 .

[21]  George Zografi,et al.  Assessment of the physical stability of lyophilized MK-0591 by differential scanning calorimetry , 1996 .

[22]  F. W. Fowler,et al.  PREPARATION OF LAYERED DIACETYLENES AS A DEMONSTRATION OF STRATEGIES FOR SUPRAMOLECULAR SYNTHESIS , 1995 .

[23]  M. C. Etter,et al.  Urea-glutaric acid (2∶1) structural aggregates as building blocks for crystal engineering , 1995 .

[24]  Gautam R. Desiraju,et al.  Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis , 1995 .

[25]  D. Tsiourvas,et al.  THERMOTROPIC LIQUID CRYSTALS FORMED BY INTERMOLECULAR HYDROGEN BONDING INTERACTIONS , 1995 .

[26]  Hiroyuki Nakazumi,et al.  Near-infrared absorbing dyes , 1992 .

[27]  M. C. Etter Encoding and decoding hydrogen-bond patterns of organic compounds , 1990 .

[28]  P. L. Gould,et al.  Salt selection for basic drugs , 1986 .

[29]  J. Finley,et al.  Technological necessity of antioxidants in the food industry. , 1986, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[30]  T. Taga,et al.  Structure redetermination and packing analysis of aspirin crystal. , 1985, Chemical & pharmaceutical bulletin.

[31]  A. Hagler,et al.  Conformational polymorphism. The influence of crystal structure on molecular conformation , 1978 .

[32]  J. Haleblian,et al.  Characterization of habits and crystalline modification of solids and their pharmaceutical applications. , 1975, Journal of pharmaceutical sciences.

[33]  J. Flippen,et al.  (+)‐2‐(2‐Fluoro‐4‐biphenyl)propionic acid (flurbiprofen) , 1975 .

[34]  L. Leiserowitz,et al.  syn-planare Konformation der Oxalsure: Kristallstruktur des Oxalsure-Acetamid-Komplexes , 1972 .

[35]  Gerhard M. J. Schmidt,et al.  Photodimerization in the solid state , 1971 .

[36]  C. Kennard,et al.  Molecular Cocrystals of Carboxylic Acids. XXV The Utility of Urea in Structure Making with Carboxylic Acids and the Crystal Structures of a Set of Six Adducts with Aromatic Acids , 1997 .

[37]  J. Kleinjans,et al.  Butylated hydroxyanisole in perspective. , 1991, Chemico-biological interactions.

[38]  F. Krahn,et al.  Relations between several polymorphic forms and the dihydrate of carbamazepine. , 1987, Pharmaceutica acta Helvetiae.

[39]  S. Byrn Solid state chemistry of drugs , 1982 .

[40]  L. Pauling The Nature Of The Chemical Bond , 1939 .