參考文獻 |
Chapter 1
Preston, E.; William, L. G. (Koppers Co., USA) Method for Recovering and Refining Cyclopentadiene. US Patent 2,349,418, May 23, 1944.
Claus, M.; Claus, E.; Claus, P.; Hönicke, D.; Födisch, R.; Olson, M. Cyclopentadiene and Cyclopentene. Ullmann′s Encyclopedia of Industrial Chemistry. Wiley-VCH. 2002. p. 61-73.
Schleyer, P. von R. A Simple Preparation of Adamantane. J. Am. Chem. Soc. 1957, 79 (12), 3292-3292.
Schleyer, P. von R.; Donaldson, M. M.; Nicholas, R. D.; Cupas, C. Adamantane. Org. Synth. 1962, 42, 8
Sasaki, T.; Eguchi, S.; Toru, T. Synthesis of Adamantane Derivatives. I. Application of the Ritter Reaction to 1-Bromoadamantane. Bull. Chem. Soc. Jpn. 1968, 41 (1), 236-238.
Smith, G. W.; Williams, H. D. Some Reactions of Adamantane and Adamantane Derivatives. J. Org. Chem. 1961, 26 (7), 2207-2212.
He, J. X.; Wang H. B.; Zhou, H. Y. Synthesis of Amantadine Hydrochloride. Chinese J. Pharm. 2013, 44 (1), 1-3.
Singh, M. S.; Chowdhury, S. Recent Developments in Solvent-Free Multicomponent Reactions: A Perfect Synergy for Eco-Compatible Organic Synthesis. RSC Adv. 2012, 2 (11), 4547-4592.
Bose, D. S.; Fatima, L.; Mereyala, H. B. Green Chemistry Approaches to the Synthesis of 5-Alkoxycarbonyl-4-Aryl-3, 4-Dihydropyrimidin-2 (1 H)-Ones by a Three-Component Coupling of One-Pot Condensation Reaction: Comparison of Ethanol, Water, and Solvent-Free Conditions. J. Org. Chem. 2003, 68 (2), 587-590.
Sheldon, R. A. Green Solvents for Sustainable Organic Synthesis: State of the Art. Green Chem. 2005, 7 (5), 267-278.
Trost, B. M. On Inventing Reactions for Atom Economy. Acc. Chem. Res. 2002, 35 (9), 695-705.
Paulekuhn, G. S.; Dressman, J. B.; Saal, C. Trends in Active Pharmaceutical Ingredient Salt Selection Based on Analysis of the Orange Book Database. J. Med. Chem. 2007, 50 (26), 6665-6672.
Saal, C.; Becker, A. Pharmaceutical Salts: A Summary on Doses of Salt Formers from the Orange Book. Eur. J. Pharmacol. 2013, 49 (4), 614-623.
Williams, H.D.; Trevaskis, N.L.; Charman, S.A.; Shanker, R.M.; Charman, W.N.; Pouton, W.C.; Porter, C.J.H. Strategies to Address Low Drug Solubility in Discovery and Development. Pharmacol. Rev. 2013, 65 (1), 315–499.
Cotton, M. L.; Lamarche, P.; Motola, S.; Vadas, E.B. L-649,923—The Selection of an Appropriate Salt Form Andpreparation of a Stable Oral Formulation. Int. J. Pharm. 1994, 109 (3), 237–249.
Liu, R. Water-Insoluble Drug Formulation. CRC Press. 2008. p. 543-545
Blagden, N.; De Matas, M.; Gavan, P. T.; York, P. Crystal Engineering of Active Pharmaceutical Ingredients to Improve Solubility and Dissolution Rates. Adv. Drug Deliv. Rev. 2007, 59 (7), 617-630.
Avdeef, A. Solubility of Sparingly-Soluble Ionizable Drugs. Adv. Drug Deliv. Rev. 2007, 59 (7), 568-590.
Serajuddin, A. T. Salt Formation to Improve Drug Solubility. Adv. Drug Deliv. Rev. 2007, 59 (7), 603-616.
Gould, P. L. Salt selection for basic drugs. Int. J. Pharm. 1986, 33 (1-3), 201-217.
David, S. Improving The Solubility and Dissolution of Poorly Soluble Drugs by Salt Formation and the Consequent Effect on Mechanical Properties. Ph.D. Dissertation, Aston University, 2005.
Stahl P. H.; Wermuth G. Handbook of Pharmaceutical Salts: Properties, Selection, and Use. Wiley-VCH. Zurich. 2002.
Bastin, R. J.; Bowker, M. J.; Slater, B. J. Salt Selection and Optimisation Procedures for Pharmaceutical New Chemical Entities. Org. Process Res. Dev. 2000, 4 (5), 427-435.
Khadka, P.; Ro, J.; Kim, H.; Kim, I.; Kim, J. T.; Kim, H.; Lee, J. Pharmaceutical Particle Technologies: An Approach to Improve Drug Solubility, Dissolution and Bioavailability. Asian J. Pharm. Sci. 2014, 9 (6), 304-316.
Hart, A. Effect of Particle Size on Detergent Powders Flowability and Tabletability. J. Chem. Eng. Process Technol. 2015, 6 (1), 215-218.
Kim, S.; Wei, C.; Kiang, S. Crystallization Process Development of an Active Pharmaceutical Ingredient and Particle Engineering via the Use of Ultrasonics and Temperature Cycling. Org. Process Res. Dev. 2003, 7 (6), 997-1001.
Kolocouris, N.; Foscolos, G. B.; Kolocouris, A.; Marakos, P.; Pouli, N.; Fytas, G.; De Clercq, E. Synthesis and Antiviral Activity Evaluation of Some Aminoadamantane Derivatives. J. Med. Chem. 1994, 37 (18), 2896-2902.
Schwab, R. S.; England, A. C.; Poskanzer, D. C.; Young, R. R. Amantadine in the Treatment of Parkinson′s Disease. JAMA 1969, 208(7), 1168-1170.
Thomas, A.; Bonanni, L.; Gambi, F.; Di Iorio, A.; Onofrj, M. Pathological Gambling in Parkinson Disease is Reduced by Amantadine. Ann. Neurol. 2010, 68 (3), 400-404.
Caumont, A. S.; Octave, J. N.; Hermans, E. Amantadine and Memantine Induce the Expression of the Glial Cell Line-Derived Neurotrophic Factor in C6 Glioma Cells. Neurosci. Lett. 2006, 394 (3), 196-201.
Davies, W. L.; Grunert, R. R.; Haff, R. F.; McGahen, J. W.; Neumayer, E. M.; Paulshock, M.; Hoffmann, C. E. Antiviral Activity of 1-Adamantanamine (Amantadine). Science 1964, 144 (3620), 862-863.
Staničová, J.; Miškovský, P.; Šutiak, V. Amantadine: An Antiviral and Antiparkinsonian Agent. Vet. Med. Czech 2001, 46 (9), 244-256.
Feigin, V. Global, Regional, and National Life Expectancy, All-Cause Mortality, and Cause-Specific Mortality for 249 Causes of Death, 1980-2015: A Systematic Analysis for the Global Burden of Disease Study 2015. The Lancet 2016, 388(10053), 1459-1544.
Vos, T. et al. Global, Regional, and National Incidence, Prevalence, and Years Lived with Disability for 310 Diseases and Injuries, 1990-2015: A Systematic Analysis for the Global Burden of Disease Study 2015. The Lancet 2016, 388(10053), 1545-1602
Foltynie, T.; Brayne, C. E.; Robbins, T. W.; Barker, R. A. The Cognitive Ability of an Incident Cohort of Parkinson′s Patients in the UK. The CamPaIGN Study. Brain. 2004, 127 (3), 550-560.
Lungare, S.; Bowen, J.; Badhan, R. Development and Evaluation of a Novel Intranasal Spray for the Delivery of Amantadine. J. Pharm. Sci. 2016, 105 (3), 1209-1220.
Centers for Disease Control and Prevention. https://www.cdc.gov/flu/professionals/antivirals/summary-clinicians.htm (accessed March 8, 2017).
Bose, A.; Das, J. K.; Das, N. Pore Modification of Deca-Dodecasil-Rhombohedral Zeolite Membrane by Carbon Loading from in Situ Decomposition of 1-Adamantanamine for Improved Gas Separation. RSC Adv. 2015, 5 (82), 67195-67205.
Sun, T.; Wong, M. S.; Ying, J. Y. Synthesis of Amorphous, Microporous Silica with Adamantanamine as a Templating Agent. Chem. Commun. 2000, (20), 2057-2058.
Bélanger-Gariépy, F.; Brisse, F.; Harvey, P. D.; Butler, I. S.; Gilson, D. F. R. Structure of Adamantanamine Hydrochloride at 143 K. Acta. Cryst. 1987, 43 (4), 756-759.
Chapter 2
Lee, T.; Kuo, C. S.; Chen, Y. H. Solubility, Polymorphism, Crystallinity, and Crystal Habit of Acetaminophen and Ibuprofen by Initial Solvent Screening. Pharm. Technol. 2006, 30 (10), 72-92.
Lee, T.; Su, Y. C.; Hou, H. J.; Hsieh, H. Y. Initial Solvent Screening of Carbamazepine, Cimetidine, and Phenylbutazone: Part 1 of 2. Pharm. Technol. 2009, 33 (5), 62-72.
He, J. X.; Wang H. B.; Zhou, H. Y. Synthesis of Amantadine Hydrochloride. Chinese J. Pharm. 2013, 44 (1), 1-3.
Kim, S.; Wei, C.; Kiang, S. Crystallization Process Development of an Active Pharmaceutical Ingredient and Particle Engineering via the Use of Ultrasonics and Temperature Cycling. Org. Process Res. Dev. 2003, 7 (6), 997-1001.
Chapter 3
Lee, T.; Kuo, C. S.; Chen, Y. H. Solubility, Polymorphism, Crystallinity, and Crystal Habit of Acetaminophen and Ibuprofen by Initial Solvent Screening. Pharm. Technol. 2006, 30 (10), 72-92.
Buckley, J.; Cebe, P.; Cherdack, D.; Crawford, J.; Ince, B. S.; Jenkins, M.; Pan, J.; Reveley, M.; Washington , N.; Wolchover, N. Nanocomposites of Poly (Vinylidene Fluoride) with Organically Modified Silicate. Polymer 2006, 47 (7), 2411-2422.
Jang, J.; Oh, J. H. Novel Crystalline Supramolecular Assemblies of Amorphous Polypyrrole Nanoparticles Through Surfactant Templating. Chem. Comm. 2002, 19, 2200-2201.
Lee, T.; Lee, Y.; Lee, H. L.; Syue, Y. R.; Chiu, Y. H.; Liou, J. Y.; Sun, Y. S. Bio-Inspired Phase Change Materials Designed for High Specific Heat of Solid Phase. Thermochim. Acta. 2014, 591, 61-67.
Bhattacharya, S.; Saha, B. K. Polymorphism Through Desolvation of the Solvates of a van der Waals Host. Cryst. Growth Des. 2013, 13 (2), 606-613.
Sridevi, N.; Yusuff, K. K. Synthesis, Characterization and Kinetic Studies on Complex Formed between Amantadine Hydrochloride and Sodium Molybdate at Physiological pH. Indian J. Chem., Sect A 2008, 47 (6), 836-842.
Colthup, N. B.; Daly, L. H.; Wiberley S. E. Introduction to Infrared and Raman Spectroscopy, 3rd ed.; Harcourt Brace Jovanovich : San Diego, 1990; pp 261-263.
Burra, S.; Reddy, P. S. Investigation of Solid-State Diversity of Amantadine Hydrochloride: Investigation of Amantadine HCl. LAP LAMBERT Acadamic, Germany, 2012, p. 42-46.
Takieddin, K.; Khimyak, Y. Z.; Fábián, L. Prediction of Hydrate and Solvate Formation Using Statistical Models. Cryst. Growth Des. 2015, 16 (1), 70-81.
Bazyleva, A. B.; Blokhin, A. V.; Kabo, A. G.; Kabo, G. J.; Emel’yanenko, V. N.; Verevkin, S. P. Thermodynamic Properties of 1-Aminoadamantane. J. Chem. Thermodynamics. 2008, 40 (3), 509-522.
Boyland, E.; Solomon, J. B. Metabolism of Polycyclic Compounds. 8 Acid-Labile Precursors of Naphthalene Produced as Metabolites of Naphthalene. Biochem. J. 1955, 59 (3), 518.
Masango, P. Cleaner Production of Essential Oils by Steam Distillation. J. Clean. Prod. 2005, 13 (8), 833-839.
Theodorou, V.; Paraskevopoulos, G.; Skobridis, K. A Mild Alkaline Hydrolysis of N-and N, N-Substituted Amides and Nitriles. ARKIVOC: Online J. Org. Chem. 2015, 2015 (vii), 101-112
Gobble, C.; Rath, N.; Chickos, J. The Vaporization Enthalpies and Vapor Pressures of Some Primary Amines of Pharmaceutical Importance by Correlation Gas Chromatography. J. Chem. Eng. Data 2013, 58 (9), 2600-2609.
Chickos, J. S.; Acree Jr, W. E. Enthalpies of Sublimation of Organic and Organometallic Compounds. 1910–2001. J. Phys. Chem. Ref. Data, 2002, 31 (2), 537-698.
He, J. X.; Wang H. B.; Zhou, H. Y. Synthesis of Amantadine Hydrochloride. Chinese J. Pharm. 2013, 44 (1), 1-3.
Derdour, L.; Reckamp, J. M.; Pink, C. Development of a Reactive Slurry Salt Crystallization to Improve Solid Properties and Process Performance and Scalability. Chem. Eng. Res. Des. 2017, 121, 207-218.
Hu, J.; Cheng, Y.; Wu, Q.; Zhao, L.; Xu, T. Host− Guest Chemistry of Dendrimer-Drug Complexes. 2. Effects of Molecular Properties of Guests and Surface Functionalities of Dendrimers. J. Phys. Chem. B 2009, 113 (31), 10650-10659.
Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities. J. Org. Chem. 1997, 62 (21), 7512-7515.
Hu, J.; Cheng, Y.; Wu, Q.; Zhao, L.; Xu, T. Host− Guest Chemistry of Dendrimer-Drug Complexes. 2. Effects of Molecular Properties of Guests and Surface Functionalities of Dendrimers. J. Phys. Chem. B 2009, 113 (31), 10650-10659.
Chapter 4
Childs, S. L.; Chyall, L. J.; Dunlap, J. T.; Smolenskaya, V. N.; Stahly, B. C.; Stahly, G. P. 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. 2004, 126 (41), 13335-13342.
Schultheiss, N.; Newman, A. Pharmaceutical Cocrystals and Their Physicochemical Properties. Cryst. Growth Des. 2009, 9 (6), 2950-2967.
Sarcevica, I.; Orola, L.; Veidis, M. V.; Podjava, A.; Belyakov, S. Crystal and Molecular Structure and Stability of Isoniazid Cocrystals with Selected Carboxylic Acids. Cryst. Growth Des. 2013, 13 (3), 1082-1090.
Lu, J.; Rohani, S. Preparation and Characterization of Theophylline− Nicotinamide Cocrystal. Org. Process Res. Dev. 2009, 13 (6), 1269-1275.
Qiao, N.; Li, M.; Schlindwein, W.; Malek, N.; Davies, A.; Trappitt, G. Pharmaceutical Cocrystals: An Overview. Int. J. Pharm. 2011, 419 (1), 1-11.
Sanphui, P.; Mishra, M. K.; Ramamurty, U.; Desiraju, G. R. Tuning Mechanical Properties of Pharmaceutical Crystals with Multicomponent Crystals: Voriconazole as a Case Study. Mol. Pharmacol. 2015, 12 (3), 889-897.
Lee, T.; Chen, J. W.; Lee, H. L.; Lin, T. Y.; Tsai, Y. C.; Cheng, S.L.; Lee, S. W.; Hu, J. C.; Chen, L. T. Stabilization and Spheroidization of Ammonium Nitrate: Co-Crystallization with Crown Ethers and Spherical Crystallization by Solvent Screening. Chem. Eng. J. 2013, 225 (1), 809-817.
Parmar, V. K.; Shah, S. A. Hydrochloride Salt Co-Crystals: Preparation, Characterization and Physicochemical Studies. Pharm. Dev. Technol. 2013, 18(2), 443-453.
Appendix
Buchiglas USA Corp. https://www.buchiglas-usa.com/en/products/glass-reactors-plants-pilo-t-plants.html
I. Addae-Mensah et al. WHO Expert Committee on Specifications for Pharmaceutical Preparations; WHO Technical Report Series — 929; WHO: Singapore, 2005 |