參考文獻 |
1. Hannah Ritchie, Max Roser and Pablo Rosado (2020) - "Energy". Published online at OurWorldInData.org. Retrieved from: ′https://ourworldindata.org/energy′ [Online Resource] (accessed April 19, 2022)
2. Hannah Ritchie, Max Roser and Pablo Rosado (2020) - "CO₂ and Greenhouse Gas Emissions". Published online at OurWorldInData.org. Retrieved from: ′https://ourworldindata.org/co2-and-other-greenhouse-gas-emissions′ [Online Resource] (accessed April 19, 2022)
3. Ludomier, G. W.; Elliott, P. Method for Recovering and Refining Cyclopentadiene. US Patent 2,349,418, May. 23, 1944.
4. 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.
5. Schleyer, P. von R. A Simple Preparation of Adamantane. J. Am. Chem. Soc. 1957, 79 (12), 3292-3292.
6. Schleyer, P. von R.; Donaldson, M. M.; Nicholas, R. D.; Cupas, C. Adamantane. Org. Synth. 1962, 42, 8.
7. 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.
8. SarmaPathy, K. Recent Advances in Process Development of Antiviral Agents Targeting the Influenza Virus: Amantadine-Remantadine-Derived Pharmaceutical Agents. Timely Top Clin Vaccines Res. 2018, 2 (2), 11-15.
9. Moiseev, I. K.; Doroshenko, R. I.; Ivanova, V. I. Synthesis of Amantadine via the Nitrate of 1-Adamantanol. Khim. -Farm. Zh. 1976, 10 (4), 32−33.
10. Smith, G. W.; Williams, H. D. Some Reactions of Adamantane and Adamantane Derivatives. J. Org. Chem. 1961, 26 (7), 2207-2212.
11. He, J. X.; Wang H. B.; Zhou, H. Y. Synthesis of Amantadine Hydrochloride. Chinese J. Pharm. 2013, 44 (1), 1-3.
12. Sönnichsen, N. Primary Energy Consumption Worldwide from 2000 to 2020 https://www.statista.com/statistics/265598/consumption-of-primary-energy-worldwide/ (accessed April 19, 2022)
13. Welton, T. Solvents and Sustainable Chemistry. Proc. R. Soc. A: Math. Phys. Eng. Sci. 2015, 471(2183).
14. Sheldon, R. A. The E Factor: Fifteen Years On. Green Chem. 2007, 9(12), 1273-1283.
15. Sheldon, R. A. The E Factor 25 Years on: The Rise of Green Chemistry and Sustainability. Green Chem. 2017, 19(1), 18-43.
16. Manahan, S. E. The E-Factor in Green Chemistry https://chem.libretexts.org/ (accessed May 5, 2022)
17. Amantadine: MedlinePlus Drug Information
https://medlineplus.gov/druginfo/meds/a682064.html (accessed May 5, 2022)
18. Indurkhya, A.; Patel, M.; Sharma, P.; Abed, S. N.; Shnoudeh, A.; Maheshwari, R.; Deb, P. K.; Tekade, R. K. Influence of Drug Properties and Routes of Drug Administration on the Design of Controlled Release System. Dosage form design considerations. Academic Press, 2018, p. 179-223.
19. Türeli, N. G., & Türeli, A. E. Industrial Perspectives and Future of Oral Drug Delivery. Nanotechnol. for Oral Drug Deliv. Academic Press, 2020, p. 483-502.
20. Gupta, D.; Bhatia, D.; Dave, V.; Sutariya, V.; Varghese Gupta, S. Salts of Therapeutic Agents: Chemical, Physicochemical, and Biological Considerations. Molecules 2018, 23(7), 1719.
21. Savjani, K. T.; Gajjar, A. K.; Savjani, J. K. Drug Solubility: Importance and Enhancement Techniques. Int. Sch. Res. Notices 2012.
22. Serajuddin, A. T. Salt formation to Improve Drug Solubility. Adv. Drug Deliv. Rev. 2007, 59(7), 603-616.
23. Fasinu, P.; Pillay, V.; Ndesendo, V. M.; du Toit, L. C.; Choonara, Y. E. Diverse Approaches for the Enhancement of Oral Drug Bioavailability. Biopharm. drug dispos. 2011, 32(4), 185-209.
24. Bharate, S. S. Recent Developments in Pharmaceutical Salts: FDA Approvals from 2015 to 2019. Drug Discov. Today 2021, 26(2), 384-398.
25. Nisar, T.; Sutherland-Foggio, H.; Husar, W. Antiviral Amantadine. Lancet Neurol. 2019, 18(12), 1080.
26. Suzuki, H.; Saito, R.; Masuda, H.; Oshitani, H.; Sato, M.; Sato, I. Emergence of Amantadine-Resistant Influenza A Viruses: Epidemiological Study. J. Infect. Chemother. 2003, 9(3), 195-200.
27. Vardanyan, R.; Hruby, V. Synthesis of essential drugs. Elsevier, 2006.
28. N. Maserejian, L.; Vinikoor-Imler, A. Dilley. Estimation of the 2020 Global Population of Parkinson’s Disease (PD). Mov Disord. 2020; 35
29. Tong, Y. Y.; Wang, J. China Production: Year to Date: Amantadine Hydrochloride ‘https://www.ceicdata.com/’ (accessed July 21, 2022)
30. Strides Pharma arm gets USFDA nod to market Amantadine Hydrochloride Softgel Capsules in America https://economictimes.indiatimes.com/industry/healthcare/biotech/pharmaceuticals/strides-pharma-arm-gets-usfda-nod-to-market-amantadine-hydrochloride-softgel-capsules-in-america/articleshow/89720391.cms (accessed July 21, 2022)
31. Stetter, H.; Mayer, J.; Schwarz, M.; Wulff, K. Beiträge zur Chemie der Adamantyl-(1)-Derivate. Chem Ber, 1960, 93(1), 226-230.
32. Wolfgang, H. Process for the Production of N-tert. Alkyl Amides and, if Desired, N-tert. Alkyl Amines. US Patent 3,152,180. Oct. 6, 1964.
33. Leonova, M. V.; Skomorokhov, M. Y.; Moiseev, I. K.; Klimochkin, Y. N. One-Pot Amination of Cage Hydrocarbons. Russ. J. Org. Chem. 2015, 51(12), 1703-1709.
34. Van Nguyen, T.; Van Pham, H.; Vu, D. B.; Dang, A. T.; Tran, V. K.; Phan, C. D. Microwave Method for the Synthesis of Amantadine Hydrochloride. Chiang Mai J. Sci. 2018, 45(6), 2454-2458.
35. Vu, D. B.; Nguyen, T. V.; Le, S. T.; Phan, C. D. An Improved Synthesis of Amantadine Hydrochloride. Org. Process Res. Dev. 2017, 21(11), 1758-1760.
36. Brown, R. L.; Snyder, J. A. 1-Aminoadamantane and Process for Purifying Same. US Patent 3,283,001, Nov. 1, 1966.
37. Marvin, P.; Watts, J. C. Pharmaceutical Compositions and Methods Utilizing 1-Aminoadamantane and Its Derivatives. US Patent 3,310,469. Mar. 21, 1967.
38. Kraus, G. A. Method for the Synthesis of Adamantane Amines. US Patent 5,599,998. Feb. 4, 1997.
39. Jack, M.; Eriks, K. Adamantyl Secondary Amines. US Patent 3,391,142. Jul. 2, 1968.
40. Phan, D. C.; Nguyen, H. T. A Simple and Economical Procedure for Synthesis of Amantadine Hydrochloride. Int. J. Pharm. Sci. Res. 2019, 10(9) 4359-4366.
41. Pham, V. H.; Tran, T. H.; Vu, B. D.; Le, H. B.; Nguyen, H. T.; Phan, D. C. A Simple Process for the Synthesis of 1-Aminoadamantane Hydrochloride. Org. Prep. Proced. Int. 2020, 52(1), 77-80.
42. Phan Thi, P. D.; Dang, T. A.; Vu, B. D.; Phan, D. C. Simple and Economical Process for Producing Amantadine Hydrochloride. ACS omega 2022, 7(6), 4787-4790.
43. Vincent, C. W.; Bruce, A. R. Method of Preparing 1-Adamantanamine. US Patent 3,388,164. Jun. 11, 1968.
44. Jirgensons, A.; Kauss, V.; Kalvinsh, I.; Gold, M. R. A Practical Synthesis of Tert-alkyl Amines via the Ritter Reaction with Chloroacetonitrile. Synthesis 2000, 2000(12), 1709-1712.
45. Schickaneder, C. P. Process for the Preparation of Adamantanamines. US Patent 2009/0082596 A1. Mar. 26, 2009.
46. Tsutsui, H.; Ichikawa, T.; Narasaka, K. Preparation of Primary Amines by the Alkylation of O-sulfonyloximes of Benzophenone Derivatives with Grignard Reagents. Bull. Chem. Soc. Jpn. 1999, 72(8), 1869-1878.
47. Kitamura, M.; Chiba, S.; Narasaka, K. Synthesis of Primary Amines and N-methylamines by the Electrophilic Amination of Grignard Reagents with 2-Imidazolidinone O-sulfonyloxime. Bull. Chem. Soc. Jpn. 2003, 76(5), 1063-1070.
48. Kitamura, M.; Suga, T.; Chiba, S.; Narasaka, K. Synthesis of Primary Amines by the Electrophilic Amination of Grignard Reagents with 1,3-dioxolan-2-one O-sulfonyloxime. Org. Lett. 2004, 6(24), 4619-4621.
49. Zhang, Z. Chinese Patent 102050744B, Jan. 23, 2011.
50. Hudson, A. E.; Herold, K. F.; Hemmings Jr, H. C. Pharmacology of Inhaled Anesthetics. Pharmacology and physiology for anesthesia, Elsevier, 2019, p. 217-240.
51. Lee, T.; Kuo, C. S. Solubility, Polymorphism, Crystallinity, and Crystal Habit of Acetaminophen and Ibuprofen. Pharm. Technol. 2006, 30(10), 72-87.
52. Khanna, R. K.; Moore, M. H. Carbamic Acid: Molecular Structure and IR Spectra. Spectrochim. Acta, Part A 1999, 55(5), 961-967.
53. Schaden, S.; Haberkorn, M.; Frank, J.; Baena, J. R.; Lendl, B. Direct Determination of Carbon Dioxide in Aqueous Solution Using Mid-infrared Quantum Cascade Lasers. Appl. Spectrosc. 2004, 58(6), 667-670.
54. Colthup, N. B.; Daly, L. H.; Wiberley S. E. Introduction to Infrared and Raman Spectroscopy, 3rd ed.; Harcourt Brace Jovanovich: San Diego, 1990
55. Wu, J. K.; Yin, M. J.; Han, W.; Wang, N.; An, Q. F. Development of High-performance Polyelectrolyte-complex-nanoparticle-based Pervaporation Membranes via Convenient Tailoring of Charged Groups. J. Mater. Sci. 2020, 55(26), 12607-12620.
56. Le Pevelen, D. D. Small Molecule X-Ray Crystallography, Theory and Workflow. 2010, p.2559-2576.
57. 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.
58. Plançon, A. New Modeling of X-ray Diffraction by Disordered Lamellar Structures, Such as Phyllosilicates. Am. Mineral. 2002, 87(11-12), 1672-1677.
59. Weeks, J. J. Melting Temperature and Change of Lamellar Thickness with Time for Bulk Polyethylene. J. Res. Natl. Inst. Stand. Technol. 1963, 67(5), 441.
60. Lee, H. L.; Cheng, Y. S.; Yeh, K. L.; Lee, T. A Novel Hydrate Form of Sodium Dodecyl Sulfate and Its Crystallization Process. ACS omega 2021, 6(24), 15770-15781.
61. Noeres, C.; Kenig, E. Y.; Górak, A. Modelling of Reactive Separation Processes: Reactive Absorption and Reactive Distillation. Chem. Eng. Process. Process Intensif. 2003, 42(3), 157-178.
62. Stankiewicz, A. Reactive Separations for Process Intensification: An Industrial Perspective. Chem. Eng. Process. Process Intensif. 2003, 42(3), 137-144.
63. Nowakowska, M.; Gamble, C.; Levendis, D. C. Bis (adamantan-1-aminium) Carbonate. Acta Crystallogr. E 2012, 68(4), 1159-1159.
64. Curzons, A. D.; Constable, D. C.; Cunningham, V. L. Solvent Selection Guide: A Guide to the Integration of Environmental, Health and Safety Criteria into the Selection of Solvents. Clean Products and Processes 1999, 1(2), 82-90.
65. Podrebarac, G. G.; Ng, F. T. T.; Rempel, G. L. A Kinetic Study of the Aldol Condensation of Acetone Using an Anion Exchange Resin Catalyst. Chem. Eng. Sci. 1997, 52(17), 2991-3002.
66. Wang, Z.; Richter, S. M.; Rozema, M. J.; Schellinger, A.; Smith, K.; Napolitano, J. G. Potential Safety Hazards Associated with Using Acetonitrile and A Strong Aqueous Base. Org. Process Res. Dev. 2017, 21(10), 1501-1508.
67. Damayanti, J. D.; Pratama, D. E.; Lee, T. Green Technology for Salt Formation: Slurry Reactive Crystallization Studies for Papaverine HCl and 1:1 Haloperidol-Maleic Acid Salt. Cryst. Growth Des. 2019, 19 (5), 2881-2891.
68. Konieczny, M.; Sosnovsky, G. Novel Aspects in the Preparation of Phorone. Z. Naturforsch. B 1978, 33(4), 454-460.
69. Wang, L. Y.; Yu, Y. M.; Yu, M. C.; Li, Y. T.; Wu, Z. Y.; Yan, C. W. A Crystalline Solid Adduct of Sulfathiazole–Amantadine: the First Dual-Drug Molecular Salt Containing Both Antiviral and Antibacterial Ingredients. CrystEngComm. 2020, 22(22), 3804-3813.
70. Wang, L. Y.; Bu, F. Z.; Li, Y. T.; Wu, Z. Y.; Yan, C. W. A Sulfathiazole–Amantadine Hydrochloride Cocrystal: the First Codrug Simultaneously Comprising Antiviral and Antibacterial Components. Cryst. Growth Des. 2020, 20(5), 3236-3246.
71. Wang, L. Y.; Zhao, M. Y.; Bu, F. Z.; Niu, Y. Y.; Yu, Y. M.; Li, Y. T.; Wu, Z. Y. Cocrystallization of Amantadine Hydrochloride with Resveratrol: the First Drug–Nutraceutical Cocrystal Displaying Synergistic Antiviral Activity. Cryst. Growth Des. 2021, 21(5), 2763-2776. |