Flow chemistry; Active pharmaceuticals; Green Chemistry; Continuous manufacturing
Abstract :
[en] Intensified production of smart drug modafinil under continuous flow and sustainable conditions.
Research center :
MolSys - Molecular Systems - ULiège
Disciplines :
Chemistry
Author, co-author :
Silva-Brenes, Diana V. ; Center for Integrated Technology and Organic Synthesis, MolSys Research Unit, University of Liège, B-4000 Liège (Sart Tilman), Belgium ; Crystallization Design Institute, Molecular Sciences Research Center, University of Puerto Rico, San Juan, Puerto Rico 00926, USA
Emmanuel, Noémie ; Université de Liège - ULiège > Département de chimie (sciences) > Center for Integrated Technology and Organic Synthesis
López Mejías, Vilmalí ; Crystallization Design Institute, Molecular Sciences Research Center, University of Puerto Rico, San Juan, Puerto Rico 00926, USA ; Department of Chemistry, University of Puerto Rico, Río Piedras Campus, San Juan, Puerto Rico 00931, USA
Duconge, Jorge; Department of Pharmaceutical Sciences, University of Puerto Rico, Medical Sciences Campus, San Juan, Puerto Rico 00936, USA
Vlaar, Cornelis ; Department of Pharmaceutical Sciences, University of Puerto Rico, Medical Sciences Campus, San Juan, Puerto Rico 00936, USA
Stelzer, Torsten ; Crystallization Design Institute, Molecular Sciences Research Center, University of Puerto Rico, San Juan, Puerto Rico 00926, USA ; Department of Pharmaceutical Sciences, University of Puerto Rico, Medical Sciences Campus, San Juan, Puerto Rico 00936, USA
Monbaliu, Jean-Christophe ; Université de Liège - ULiège > Département de chimie (sciences) > Center for Integrated Technology and Organic Synthesis
Language :
English
Title :
Out-smarting smart drug modafinil through flow chemistry
NASA - National Aeronautics and Space Administration [US-DC] [US-DC] UPR - Universidad de Puerto Rico [PR] ULiège - Université de Liège [BE] F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]
Wang S.-M. Han C. Lee S.-J. Jun T.-Y. Patkar A. A. Masand P. S. Pae C.-U. J. Psychiatr. Res. 2017 84 292 300 10.1016/j.jpsychires.2016.09.034 27810669
Conley C. C. Kamen C. S. Heckler C. E. Janelsins M. C. Morrow G. R. Peppone L. J. Scalzo A. J. Gross H. Dakhil S. Mustian K. M. Palesh O. G. J. Clin. Psychopharmacol. 2016 36 82 85 10.1097/JCP.0000000000000442 26658264
Goss A. J. Kaser M. Costafreda S. G. Sahakian B. J. Fu C. H. J. Clin. Psychiatry 2013 74 1101 1107 10.4088/JCP.13r08560 24330897
Hilton-Jones D. Bowler M. Lochmueller H. Longman C. Petty R. Roberts M. Rogers M. Turner C. Wilcox D. Neuromuscular Disord. 2012 22 597 603 10.1016/j.nmd.2012.02.005 22425060
Kredlow M. A. Keshishian A. Oppenheimer S. Otto M. W. J. Clin. Psychopharmacol. 2019 39 455 461 10.1097/JCP.0000000000001085 31433334
Teodorini R. D. Rycroft N. Smith-Spark J. H. PLoS One 2020 15 e0227818 10.1371/journal.pone.0227818 32023288
Franke A. G. Bagusat C. Dietz P. Hoffmann I. Simon P. Ulrich R. Lieb K. BMC Med. 2013 11 102 10.1186/1741-7015-11-102 23570256
Maher B. Nature 2008 452 674 675 10.1038/452674a 18401370
Estrada A. Kelley A. M. Webb C. M. Athy J. R. Crowley J. S. Aviat., Space Environ. Med. 2012 83 556 564 10.3357/ASEM.3129.2012 22764609
Air Force Special Operations Command/Division, Aerospace Medicine, AFSOCI48-101, 2012
United States Air Force, Modafinil and Management of Aircrew Fatigue, Washington, DC, 2003
National Aeronautics and Space Administration/Division, Medical Kit- Contents and Reference, MED CL/SpX-6 - ALL/FIN/T, 2015
Šonka K., Šóš P. and Susta M., in Drug Treatment of Sleep Disorders, ed. A. Guglietta, Springer International Publishing, Switerland, 2015, ch. Modafinil and Armodafinil, pp. 211-230, https://dx.doi.org/10.1007/978-3-319-11514-6
Lafon L., US Pat, US4,177,290, 1979
Lafon L., France Pat, FR2385693, 1978
Kleemann A., Engel J., Kutscher B. and Reichert D., Pharmaceutical Substances: Syntheses, Patents and Applications of the most relevant APIs, Georg Thieme Verlag, Stuttgart, 5th edn, completely revised edn., 2009
Chatterjie N. Stables J. P. Wang H. Alexander G. J. Neurochem. Res. 2004 29 1481 1486 10.1023/B:NERE.0000029559.20581.1a 15260124
Jung J.-C. Lee Y. Son J.-Y. Lim E. Jung M. Oh S. Molecules 2012 17 10446 10458 10.3390/molecules170910446 22945025
Bhatt S. B., Patel J. R., Panchasara D., Shah H. R., Deo K. and Kansal V. K., US Pat, US2006/0128812A1, 2006
Liang S., International Pat, WO2004/075841A2, 2004
Fornaroli M., Velardi F., Colli C. and Baima R., US Pat, US2004/0106829A1, 2004
Bogolubsky A. V. Moroz Y. S. Mykhailiuk P. K. Ostapchuk E. N. Rudnichenko A. V. Dmytriv Y. V. Bondar A. N. Zaporozhets O. A. Pipko S. E. Doroschuk R. A. Babichenko L. N. Konovets A. I. Tolmachev A. ACS Comb. Sci. 2015 17 348 354 10.1021/acscombsci.5b00024 25932994
Singer C., Gershon N., Ceausu A., Lieberman A. and Aronhime J., International Pat, WO02/10125A1, 2002
Ceausu A., Lieberman A. and Aronhime J., US Pat, US 8,048,222 B2, 2011
Prisinzano T. Podobinski J. Tidgewell K. Luo M. Swenson D. Tetrahedron: Asymmetry 2004 15 1053 1058 10.1016/j.tetasy.2004.01.039
Zhang J. and Cue Jr. B. W., Green Techniques for Organic Synthesis and Medicinal Chemistry, 2012, pp. 631-658, https://dx.doi.org/10.1002/9780470711828.ch24
Held F. E. Stingl K. A. Tsogoeva S. B. Symmetry 2017 9 88 10.3390/sym9060088
Cao J. Prisinzano T. E. Okunola O. M. Kopajtic T. Shook M. Katz J. L. Newman A. H. ACS Med. Chem. Lett. 2011 2 48 52 10.1021/ml1002025 21344069
Olivo H. F. Osorio-Lozada A. Peeples T. L. Tetrahedron: Asymmetry 2005 16 3507 3511 10.1016/j.tetasy.2005.07.028
Maurya S. Yadav D. Pratap K. Kumar A. Green Chem. 2017 19 629 633 10.1039/C6GC02623K
Bicherov A. V. Akopova A. R. Spiglazov V. I. Morkovnik A. S. Russ. Chem. Bull. 2010 59 91 101 10.1007/s11172-010-0049-8
Castaldi G., Lucchini V. and Tarquini A., EP Pat, WO2003/095423, 2007
Mauritz K. A. Moore R. B. Chem. Rev. 2004 104 4535 4586 10.1021/cr0207123 15669162
Hayden S. Glasnov T. Kappe C. O. Chem. Eng. Technol. 2015 38 1743 1748 10.1002/ceat.201400581
Kassin V.-E. H. Gérardy R. Toupy T. Collin D. Salvadeo E. Toussaint F. Van Hecke K. Monbaliu J.-C. M. Green Chem. 2019 21 2952 2966 10.1039/C9GC00336C
Kassin V.-E. H. Morodo R. Toupy T. Jacquemin I. Van Hecke K. Robiette R. Monbaliu J.-C. M. Green Chem. 2021 23 2336 2351 10.1039/D0GC04395H
Morodo R. Gérardy R. Petit G. Monbaliu J.-C. M. Green Chem. 2019 21 4422 4433 10.1039/C9GC01819K
Rogers L. Jensen K. F. Green Chem. 2019 21 3481 3498 10.1039/C9GC00773C
Gérardy R. Emmanuel N. Toupy T. Kassin V.-E. Tshibalonza N. N. Schmitz M. Monbaliu J.-C. M. Eur. J. Org. Chem. 2018 2301 2351 10.1002/ejoc.201800149
Cole K. P. Johnson M. D. Expert Rev. Clin. Pharmacol. 2018 11 5 13 10.1080/17512433.2018.1413936 29206489
Dong Z. Wen Z. Zhao F. Kuhn S. Noël T. Chem. Eng. Sci.: X 2021 10 100097
Adamo A. Beingessner R. L. Behnam M. Chen J. Jamison T. F. Jensen K. F. Monbaliu J.-C. M. Myerson A. S. Revalor E. M. Snead D. R. Stelzer T. Weeranoppanant N. Wong S. Y. Zhang P. Science 2016 352 61 10.1126/science.aaf1337 27034366
Mascia S. Heider P. L. Zhang H. Lakerveld R. Benyahia B. Barton P. I. Braatz R. D. Cooney C. L. Evans J. M. B. Jamison T. F. Jensen K. F. Myerson A. S. Trout B. L. Angew. Chem., Int. Ed. 2013 52 12359 12363 10.1002/anie.201305429 24115355
Zhang P. Weeranoppanant N. Thomas D. A. Tahara K. Stelzer T. Russell M. G. O'Mahony M. Myerson A. S. Lin H. Kelly L. P. Jensen K. F. Jamison T. F. Dai C. Cui Y. Briggs N. Beingessner R. L. Adamo A. Chem. - Eur. J. 2018 24 2776 2784 10.1002/chem.201706004 29385292
Yalkowsky S. H., He Y. and Jain P., Handbook of Aqueous Solubility Data, CRC Press, Boca Raton, 2nd edn, 2010
Gavriilidis A. Constantinou A. Hellgardt K. Hii K. K. Hutchings G. J. Brett G. L. Kuhn S. Marsden S. P. React. Chem. Eng. 2016 1 595 612 10.1039/C6RE00155F
Gemoets H. P. L. Su Y. Shang M. Hessel V. Luque R. Noël T. Chem. Soc. Rev. 2016 45 83 117 10.1039/C5CS00447K 26203551
F. a. D. Administration, Q3C—Tables and List Guidance for Industry, https://www.fda.gov/regulatory-information/search-fda-guidance-documents/q3c-tables-and-list-rev-4
Sato K. Aoki M. Ogawa M. Hashimoto T. Noyori R. J. Org. Chem. 1996 61 8310 8311 10.1021/jo961287e 11667823
Sato K. Hyodo M. Aoki M. Zheng X.-Q. Noyori R. Tetrahedron 2001 57 2469 2476 10.1016/S0040-4020(01)00068-0
Noyori R. Aoki M. Sato K. Chem. Commun. 2003 1977 1986 https://dx.doi.org/10.1039/B303160H 10.1039/B303160H 12934880
Bishopp S. D. Scott J. L. Torrente-Murciano L. Green Chem. 2014 16 3281 3285 10.1039/C4GC00598H
Tykodi R. J. J. Chem. Educ. 1990 67 146 10.1021/ed067p146
Chivilikhin M. Kuandykov L. Cerato-Noyerie C. Woehl P. Lavric E. D. Chem. Eng. Trans. 2011 25 791 796
Anastas P. Eghbali N. Chem. Soc. Rev. 2010 39 301 312 10.1039/B918763B 20023854
Rippey J. C. R. Stallwood M. I. Emerg. Med. J. 2005 22 878 879 10.1136/emj.2004.015800 16299199
Slater C. S. Savelski M. J. Hitchcock D. Cavanagh E. J. J. Environ. Sci. Health, Part A: Toxic/Hazard. Subst. Environ. Eng. 2016 51 487 494 10.1080/10934529.2015.1128719 26889729
Van Aken K. Strekowski L. Patiny L. Beilstein J. Org. Chem. 2006 2 3
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