Citation: Jingrui He, Ziyi Li, Gagan Dhawan, Wei Zhang, Alexander E. Sorochinsky, Greg Butler, Vadim A. Soloshonok, Jianlin Han. Fluorine-containing drugs approved by the FDA in 2021[J]. Chinese Chemical Letters, ;2023, 34(1): 107578. doi: 10.1016/j.cclet.2022.06.001 shu

Fluorine-containing drugs approved by the FDA in 2021

Jingrui He ^a ,
Ziyi Li ^a ,
Gagan Dhawan ^{b, *,} ,
Wei Zhang ^{c, *,} ,
Alexander E. Sorochinsky ^d ,
Greg Butler ^e ,
Vadim A. Soloshonok ^{f, g, **,} ,
Jianlin Han ^{a, *,}

a.
Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
b.
Department of Biomedical Science, Acharya Narendra Dev College, University of Delhi, New Delhi 110019, India
c.
Department of Chemistry, University of Massachusetts Boston, Boston, MA 02125, United States
d.
V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, The National Academy of Sciences of Ukraine, Kyiv 02094, Ukraine
e.
Oakwood Chemical, Inc., Estill, SC 29918, United States
f.
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, 20018 San Sebastián, Spain
g.
IKERBASQUE, Basque Foundation for Science, Plaza Bizkaia, 48013 Bilbao, Spain

^**

gagandhawan@andc.du.ac.in

wei2.zhang@umb.edu

vadym.soloshonok@ehu.es

hanjl@njfu.edu.cn

Received Date: 30 March 2022
Revised Date: 29 May 2022
Accepted Date: 1 June 2022
Available Online: 3 June 2022

Figures(19)

Nine new fluorine-containing drugs have been approved by the US Food and Drug Administration (FDA) in 2021, which are presented in this review article. These small molecular drugs feature aromatic fluorine, trifluoromethyl and chlorodifluoro groups. The therapeutic areas of these fluorine-containing drugs include multiple myeloma, lymphoma, HIV, chronic heart failure, chronic myeloid leukemia, (ANCA)-associated vasculitis, migraines, von Hippel-Lindau disease, and non-small cell lung cancer. The brief biological activities and the synthetic methods have been discussed in this review for each of these nine drugs.
- Fluorine-containing compounds,
- Blockbuster drugs,
- Pharmaceuticals,
- Anti-cancer,
- Drug design and development,
- Asymmetric synthesis
1. [1]
  R.E. Banks, V. Murtagh, H.M. Marsden, R.G. Syvret, J. Fluorine Chem. 122 (2001) 271–275. doi: 10.1016/S0022-1139(01)00510-3
2. [2]
  X.Y. Yang, T. Wu, R.J. Phipps, F.D. Toste, Chem. Rev. 115 (2015) 826–870. doi: 10.1021/cr500277b
3. [3]
  R.G. Syvret, K.M. Butt, T.P. Nguyen, V.L. Bulleck, R.D. Rieth, J. Org. Chem. 67 (2002) 4487–4493. doi: 10.1021/jo020053u
4. [4]
  M. Reichel, K. Karaghiosoff, Angew. Chem. Int. Ed. 59 (2020) 12268–12281. doi: 10.1002/anie.201913175
5. [5]
  P. Bravo, M. Guidetti, F. Viani, et al., Tetrahedron 54 (1998) 12789–12806. doi: 10.1016/S0040-4020(98)00779-0
6. [6]
  X. Xu, K. Matsuzaki, N. Shibata, Chem. Rev. 115 (2015) 731–764. doi: 10.1021/cr500193b
7. [7]
  H. Ohkura, D.O. Berbasov, V.A. Soloshonok, Tetrahedron 59 (2003) 1647–1656. doi: 10.1016/S0040-4020(03)00138-8
8. [8]
  K. Gondo, T. Kitamura, Molecules 17 (2012) 6625–6632. doi: 10.3390/molecules17066625
9. [9]
  J. Han, A.E. Sorochinsky, T. Ono, V.A. Soloshonok, Curr. Org. Synth. 8 (2011) 281–294. doi: 10.2174/157017911794697277
10. [10]
  R.G. Syvret, W.J. Casteel, G.S. Lal, J.S. Goudar, J. Fluorine Chem. 125 (2004) 33–35. doi: 10.1016/j.jfluchem.2003.09.002
11. [11]
  G.V. Röschenthaler, V.P. Kukhar, I.B. Kulik, et al., Tetrahedron Lett. 53 (2012) 539–542. doi: 10.1016/j.tetlet.2011.11.096
12. [12]
  M.S. Wiehn, E.V. Vinogradova, A. Togni, J. Fluorine Chem. 131 (2010) 951–957. doi: 10.1016/j.jfluchem.2010.06.020
13. [13]
  M. Shevchuk, Q. Wang, R. Pajkert, et al., Adv. Synth. Catal. 363 (2021) 2912–2968. doi: 10.1002/adsc.202001464
14. [14]
  E. Merino, C. Nevado, Chem. Soc. Rev. 43 (2014) 6598–6608. doi: 10.1039/C4CS00025K
15. [15]
  J.A. Ma, D. Cahard, J. Fluorine Chem. 128 (2007) 975–996. doi: 10.1016/j.jfluchem.2007.04.026
16. [16]
  S.S. Li, J. Wang, Acta Chim. Sin. 76 (2018) 913–924. doi: 10.6023/a18070306
17. [17]
  J. Hu, K. Ding, Acta Chim. Sin. 76 (2018) 905–906. doi: 10.6023/a1812e001
18. [18]
  E.P. Gillis, K.J. Eastman, M.D. Hill, D.J. Donnelly, N.A. Meanwell, J. Med. Chem. 58 (2015) 8315–8359. doi: 10.1021/acs.jmedchem.5b00258
19. [19]
  I. Ojima, J. Fluorine Chem. 198 (2017) 10–23. doi: 10.1016/j.jfluchem.2016.12.016
20. [20]
  J. Wang, M. Sánchez-Roselló, J.L. Aceña, et al., Chem. Rev. 114 (2014) 2432–2506. doi: 10.1021/cr4002879
21. [21]
  Y. Zhou, J. Wang, Z. Gu, et al., Chem. Rev. 116 (2016) 422–518. doi: 10.1021/acs.chemrev.5b00392
22. [22]
  Y. Zhu, J. Han, J. Wang, et al., Chem. Rev. 118 (2018) 3887–3964. doi: 10.1021/acs.chemrev.7b00778
23. [23]
  J. Han, L. Kiss, H. Mei, et al., Chem. Rev. 121 (2021) 4678–4742. doi: 10.1021/acs.chemrev.0c01263
24. [24]
  H. Mei, J. Han, K.D. Klika, et al., Eur. J. Med. Chem. 186 (2020) 111826. doi: 10.1016/j.ejmech.2019.111826
25. [25]
  H. Mei, J. Han, S. White, et al., Chem. Eur. J. 26 (2020) 11349–11390. doi: 10.1002/chem.202000617
26. [26]
  H. Mei, J. Han, S. Fustero, et al., Chem. Eur. J. 25 (2019) 11797–11819. doi: 10.1002/chem.201901840
27. [27]
  H. Mei, A.M. Remete, Y. Zou, et al., Chin. Chem. Lett. 31 (2020) 2401–2413. doi: 10.1016/j.cclet.2020.03.050
28. [28]
  Y. Yu, A. Liu, G. Dhawan, et al., Chin. Chem. Lett. 32 (2021) 3342–3354. doi: 10.1016/j.cclet.2021.05.042
29. [29]
  J. Han, A.M. Remete, L.S. Dobson, et al., J. Fluorine Chem. 239 (2020) 109639. doi: 10.1016/j.jfluchem.2020.109639
30. [30]
  S. Purser, P.R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 37 (2008) 320–330. doi: 10.1039/B610213C
31. [31]
  C. Isanbor, D. O'Hagan, J. Fluorine Chem. 127 (2006) 303–319. doi: 10.1016/j.jfluchem.2006.01.011
32. [32]
  Q. Wang, H. Song, Q. Wang, Chin. Chem. Lett. 33 (2022) 626–642. doi: 10.1016/j.cclet.2021.07.064
33. [33]
  Y. Ogawa, E. Tokunaga, O. Kobayashi, K. Hirai, N. Shibata, iScience 23 (2020) 101467. doi: 10.1016/j.isci.2020.101467
34. [34]
  T. Fujiwara, D. O'Hagan, J. Fluorine Chem. 167 (2014) 16–29. doi: 10.1016/j.jfluchem.2014.06.014
35. [35]
  C. Qin, W. Liu, Y. Nie, et al., Chin. J. Org. Chem. 40 (2020) 2232–2253. doi: 10.6023/cjoc202003051
36. [36]
  P. Chen, W. Bai, Y. Bao, J. Mater. Chem. C 7 (2019) 11731–11746. doi: 10.1039/c9tc04567h
37. [37]
  S. Dhillon, Drugs 81 (2021) 963–969. doi: 10.1007/s40265-021-01522-0
38. [38]
  M. Wickström, P. Nygren, R. Larsson, et al., Oncotarget 8 (2017) 66641–66655. doi: 10.18632/oncotarget.18420
39. [39]
  M. Fortunato, T. Giovanni, A.M. Enrica, et al., Drug Des. Dev. Ther. 15 (2021) 2969–2978. doi: 10.2147/DDDT.S295215
40. [40]
  F. Lehmann, J. Wennerberg, Melflufen: a journey from discovery to multi-kilogram production, in J.A. Pesti, A.F. Abdel-Magid, R. Vaidyanathan, Eds., Complete Accounts of Integrated Drug Discovery and Development: Recent Examples from the Pharmaceutical Industry, Volume 3, ACS Symposium Series, 1369; American Chemical Society: Washington DC, USA, (2020), Chapter 5; pp. 157–177.
41. [41]
  F. Schjesvold, M. Dimopoulos, S. Delimpasi, et al., Lancet Haematol. 9 (2022) e98–e110. doi: 10.1016/S2352-3026(21)00381-1
42. [42]
  J. Gullbo, M. Tullberg, J. Våbenø, et al., Oncol. Res. 14 (2003) 113–132. doi: 10.3727/000000003771013071
43. [43]
  H. Cotton, B. Bäckström, I. Fritzson, et al., Org. Process Res. Dev. 23 (2019) 1191–1196. doi: 10.1021/acs.oprd.9b00116
44. [44]
  D. Sohita, J.K. Susan, Drugs 81 (2021) 857–866. doi: 10.1007/s40265-021-01504-2
45. [45]
  H.A. Burris III, I.W. Flinn, M.R. Patel, et al., Lancet Oncol. 19 (2018) 486–496. doi: 10.1016/S1470-2045(18)30082-2
46. [46]
  N.H. Fowler, F. Samaniego, W. Jurczak, et al., J. Clin. Oncol. 39 (2021) 1609–1618. doi: 10.1200/jco.20.03433
47. [47]
  M. Muthuppalaniappan, S. Viswanadha, G. Babu, S.K.V.S. Vakkalanka, PT US20110118257 A1, 2011.
48. [48]
  M.S. Weiss, H.P. Miskin, P. Sportelli, S.K.V.S. Vakkalanka, PT US 20150290317 A1, 2015.
49. [49]
  S.K.V.S. Vakkalanka, M. Muthuppa-Laniappan, D. Nagarathnam, PT WO2014006572 A1, 2014.
50. [50]
  A.D. Zelenetz, L.I. Gordon, J.E. Chang, et al., J. Natl. Compr. Canc. Netw. 19 (2021) 1218–1230. doi: 10.6004/jnccn.2021.0054
51. [51]
  A. Markham, Drugs 80 (2020) 915–822. doi: 10.1007/s40265-020-01326-8
52. [52]
  D.A. Margolis, J. Gonzalez-Garcia, H.J. Stellbrink, et al., Lancet 390 (2017) 1499–1510. doi: 10.1016/S0140-6736(17)31917-7
53. [53]
  T. Zhou, H. Su, P. Dash, et al., Biomaterials 151 (2018) 53–65. doi: 10.1016/j.biomaterials.2017.10.023
54. [54]
  C. Trezza, S.L. Ford, W. Spreen, R. Pan, S. Piscitelli, Curr. Opin. HIV AIDS 10 (2015) 239–245. doi: 10.1097/COH.0000000000000168
55. [55]
  S.A. Hassounah, A. Alikhani, M. Oliveira, et al., Antimicrob. Agents Chemother. 61 (2017) 1–9. doi: 10.1128/AAC.01695-17
56. [56]
  A.J. Brian, K. Takashi, G.W. Jason, et al., J. Med. Chem. 56 (2013) 5901–5916. doi: 10.1021/jm400645w
57. [57]
  H. Wang, M.D. Kowalski, A.S. Lakdawala, F.G. Vogt, L. Wu, Org. Lett. 17 (2015) 564–567. doi: 10.1021/ol503580t
58. [58]
  L.H. David, Org. Process Res. Dev. 23 (2019) 716–729. doi: 10.1021/acs.oprd.9b00031
59. [59]
  M. Sanford, Drugs 72 (2012) 525–541. doi: 10.2165/11208590-000000000-00000
60. [60]
  M. Sharma, L. Saravolatz, J. Antimicrob. Chemoth. 68 (2013) 250–256. doi: 10.1093/jac/dks404
61. [61]
  X.Q. Feng, Y.H. Liang, Z.S. Zeng, et al., ChemMedChem 4 (2009) 219–224. doi: 10.1002/cmdc.200800334
62. [62]
  J. Guillemont, E. Pasquier, P. Palandjian, et al., J. Med. Chem. 48 (2005) 2072–2079. doi: 10.1021/jm040838n
63. [63]
  M. Anthony, D. Sean, Drugs 81 (2021) 721–726. doi: 10.1007/s40265-021-01496-z
64. [64]
  B. Michael, G. Michael, L. Maximilian, et al., Clin. Pharmacokinet. 59 (2020) 1407–1418. doi: 10.1007/s40262-020-00895-x
65. [65]
  L. Nguyen, D.E. Baker, Hosp. Pharm. (2021), doi:10.1177/00185787211016338. doi: 10.1177/00185787211016338
66. [66]
  M. Follmann, J. Ackerstaff, G. Redlich, et al., J. Med. Chem. 60 (2017) 5146–5161. doi: 10.1021/acs.jmedchem.7b00449
67. [67]
  C. Hirth-Dietrich, P. Sandner, J.P. Stasch, et al., PT WO2011147810 A1, 2011.
68. [68]
  A. Alsumali, D. Lautsch, R. Liu, et al., Adv. Ther. 38 (2021) 2631–2643. doi: 10.1007/s12325-021-01681-2
69. [69]
  E.D. Deeks, Drugs 82 (2022) 219–226. doi: 10.1007/s40265-021-01662-3
70. [70]
  M. Breccia, G. Colafigli, E. Scalzulli, M. Martelli, Expert Opin. Investig. Drugs 30 (2021) 803–811. doi: 10.1080/13543784.2021.1941863
71. [71]
  R. Kurzrock, J.U. Gutterman, M. Talpaz, N. Engl. J. Med. 319 (1988) 990–998. doi: 10.1056/NEJM198810133191506
72. [72]
  A.A. Wylie, J. Schoepfer, W. Jahnke, et al., Nature 543 (2017) 733–737. doi: 10.1038/nature21702
73. [73]
  T.P. Hughes, M.D. Michael, J. Mauro, et al., N. Engl. J. Med. 381 (2019) 2315–2326. doi: 10.1056/nejmoa1902328
74. [74]
  S.K. Dodd, P. Furet, R.M. Grotzfeld, et al., PT WO2013171639A1, 2013.
75. [75]
  J. Zhang, F.J. Adrian, W. Jahnke, et al., Nature 463 (2010) 501–506. doi: 10.1038/nature08675
76. [76]
  J. Schoepfer, W. Jahnke, G. Berellini, et al., J. Med. Chem. 61 (2018) 8120–8135. doi: 10.1021/acs.jmedchem.8b01040
77. [77]
  P.J. Goadsby, L. Edvinsson, R. Ekman, Ann. Neurol. 28 (1990) 183–187. doi: 10.1002/ana.410280213
78. [78]
  J.L. Bellamy, R.K. Cady, P.L. Durham, Headache 46 (2006) 24–33. doi: 10.1111/j.1526-4610.2006.00294.x
79. [79]
  L.H. Lassen, P.A. Haderslev, V.B. Jacobsen, H.K. Iversen, B. Sperling, J. Olesen, Cephalalgia 22 (2002) 54–61. doi: 10.1046/j.1468-2982.2002.00310.x
80. [80]
  J. Olesen, H.C. Diener, I.W. Husstedt, et al., N. Engl. J. Med. 350 (2004) 1104–1110. doi: 10.1056/NEJMoa030505
81. [81]
  K.A. Petersen, L.H. Lassen, S. Birk, L. Lesko, J. Olesen, Clin. Pharmacol. Ther. 77 (2005) 202–213. doi: 10.1016/j.clpt.2004.10.001
82. [82]
  H. Doods, G. Hallermayer, D. Wu, et al., Br. J. Pharmacol. 129 (2000) 420–423. doi: 10.1038/sj.bjp.0703110
83. [83]
  L. Edvinsson, P.J. Goadsby, Cephalalgia 14 (1994) 320–327. doi: 10.1046/j.1468-2982.1994.1405320.x
84. [84]
  M. Ashina, L. Bendtsen, R. Jensen, et al., Neurology 55 (2000) 1335–1340. doi: 10.1212/WNL.55.9.1335
85. [85]
  P. Holzer, Neuroscience 24 (1998) 739–768.
86. [86]
  A.M. Salmon, M.I. Damaj, L.M. Marubio, et al., Nat. Neurosci. 4 (2001) 357–358. doi: 10.1038/86001
87. [87]
  A. May, M.A. Gamulescu, U. Bogdahn, C.P. Lohmann, Cephalalgia 22 (2002) 195–196. doi: 10.1046/j.1468-2982.2002.00342.x
88. [88]
  F. Chen, C. Molinaro, W.P. Wuelfing, et al., PTWO2013169348, 2013.
89. [89]
  I.M. Bell, M.E. Fraley, S.N. Gallicchio, et al., PTWO2012064910A1, 2012.
90. [90]
  P.F. Kohler, H.J. Müller-Eberhard, J. Immunol. 99 (1967) 1211–1216. doi: 10.4049/jimmunol.99.6.1211
91. [91]
  R. Schindler, J.A. Gelfand, C.A. Dinarello, Blood 76 (1990) 1631–1638. doi: 10.1182/blood.V76.8.1631.1631
92. [92]
  N. Haeffner-Cavaillon, J.M. Cavaillon, M. Laude, M.D. Kazatchkine, J. Immunol. 139 (1987) 794–799. doi: 10.4049/jimmunol.139.3.794
93. [93]
  J.M. Cavaillon, C. Fitting, N. Haeffner-Cavaillon, Eur. J. Immunol. 20 (1990) 253–257. doi: 10.1002/eji.1830200204
94. [94]
  D.E. van Epps, D.E. Chenoweth, J. Immunol. 132 (1984) 2862–2867. doi: 10.4049/jimmunol.132.6.2862
95. [95]
  D.L. Haviland, R.L. McCoy, W.T. Whitehead, et al., J. Immunol. 154 (1995) 1861–1869. doi: 10.4049/jimmunol.154.4.1861
96. [96]
  R.A. Wetsel, Immunol. Lett. 44 (1995) 183–187. doi: 10.1016/0165-2478(94)00212-A
97. [97]
  R.R. Buchner, T.E. Hugli, J.A. Ember, E.L. Morgan, J. Immunol. 155 (1995) 308–315. doi: 10.4049/jimmunol.155.1.308
98. [98]
  D.E. Chenoweth, T.E. Hugli, Proc. Natl. Acad. Sci. USA 75 (1978) 3943–3947. doi: 10.1073/pnas.75.8.3943
99. [99]
  J. Zwirner, A. Fayyazi, O. Götze, Mol. Immunol. 36 (1999) 877–884. doi: 10.1016/S0161-5890(99)00109-1
100. [100]
  H. Sumichika, K. Sakata, N. Sato, et al., J. Biol. Chem. 277 (2002) 49403–49407. doi: 10.1074/jbc.M209672200
101. [101]
  A.J. Strachan, T.M. Woodruff, G. Haaima, D.P. Fairlie, S.M. Taylor, J. Immunol. 164 (2000) 6560–6565. doi: 10.4049/jimmunol.164.12.6560
102. [102]
  D.R.W. Jayne, P.A. Merkel, T.J. Schall, P. Bekker, N. Engl. J. Med. 384 (2021) 599–609. doi: 10.1056/nejmoa2023386
103. [103]
  D.R.W. Jayne, A.N. Bruchfeld, L. Harper, et al., J. Am. Soc. Nephrol. 28 (2017) 2756–2767. doi: 10.1681/ASN.2016111179
104. [104]
  K.J. Warrington, N. Engl. J. Med. 384 (2021) 664–665. doi: 10.1056/nejme2033621
105. [105]
  A. Lee, Drug 82 (2022) 79–85. doi: 10.1007/s40265-021-01643-6
106. [106]
  P. Fan, K.L. Greenman, M.R. Leleti, et al., PT WO 2011163640 A1, 2011.
107. [107]
  P. Fan, J. Kalisiak, A. Krasinski, et al., PT US 9745268 B2, 2017.
108. [108]
  E.D. Deeks, Drugs 81 (2021) 1921–1927. doi: 10.1007/s40265-021-01606-x
109. [109]
  T.K. Choueiri, T.M. Bauer, K.P. Papadopoulos, et al., Nat. Med. 27 (2021) 802–805. doi: 10.1038/s41591-021-01324-7
110. [110]
  P. Jaakkola, D.R. Mole, Y.M. Tian, et al., Science 292 (2001) 468–472. doi: 10.1126/science.1059796
111. [111]
  R.K. Bruick, S.L. McKnight, Science 294 (2001) 1337–1340. doi: 10.1126/science.1066373
112. [112]
  T.H. Scheuermann, D.R. Tomchick, M. Machius, et al., Proc. Natl. Acad. Sci. USA 106 (2009) 450–455. doi: 10.1073/pnas.0808092106
113. [113]
  T.H. Scheuermann, Q. Li, H.W. Ma, et al., Nat. Chem. Biol. 9 (2013) 271–276. doi: 10.1038/nchembio.1185
114. [114]
  J.L. Rogers, L. Bayeh, T.H. Scheuermann, et al., J. Med. Chem. 56 (2013) 1739–1747. doi: 10.1021/jm301847z
115. [115]
  T.H. Scheuermann, D. Stroud, C.E. Sleet, et al., J. Med. Chem. 58 (2015) 5930–5941. doi: 10.1021/acs.jmedchem.5b00529
116. [116]
  P.W. Wehn, J.P. Rizzi, D.D. Dixon, et al., J. Med. Chem. 61 (2018) 9691–9721. doi: 10.1021/acs.jmedchem.8b01196
117. [117]
  E.M. Wallace, J.P. Rizzi, G. Han, et al., Cancer Res. 76 (2016) 5491–5500. doi: 10.1158/0008-5472.CAN-16-0473
118. [118]
  H. Cho, X. Du, J.P. Rizzi, et al., Nature 539 (2016) 107–111. doi: 10.1038/nature19795
119. [119]
  W. Chen, H. Hill, A. Christie, et al., Nature 539 (2016) 112–117. doi: 10.1038/nature19796
120. [120]
  R. Xu, K. Wang, J.P. Rizzi, et al., J. Med. Chem. 62 (2019) 6876–6893. doi: 10.1021/acs.jmedchem.9b00719
121. [121]
  T.K. Choueiri, R.J. Motzer, N. Engl. J. Med. 376 (2017) 354–366. doi: 10.1056/NEJMra1601333
122. [122]
  J.A. Josey, R. Shrimali, E.M. Wallace, T. Wong, PT WO2019191227, 2019.
123. [123]
  A.D. Cox, S.W. Fesik, A.C. Kimmelman, J. Luo, C.J. Der, Nat. Rev. Drug Discov. 13 (2014) 828–851. doi: 10.1038/nrd4389
124. [124]
  G.A. Hobbs, C.J. Der, K.L. Rossman, J. Cell Sci. 129 (2016) 1287–1292. doi: 10.1242/jcs.182873
125. [125]
  I.A. Prior, P.D. Lewis, C. Mattos, Cancer Res. 72 (2012) 2457–2467. doi: 10.1158/0008-5472.CAN-11-2612
126. [126]
  J. Canon, K. Rex, A.Y. Saiki, et al., Nature 575 (2019) 217–223. doi: 10.1038/s41586-019-1694-1
127. [127]
  J.M. Ostrem, U. Peters, M.L. Sos, J.A. Wells, K.M. Shokat, Nature 503 (2013) 548–551. doi: 10.1038/nature12796
128. [128]
  T. Pantsar, Sci. Rep. 10 (2020) 11992. doi: 10.1038/s41598-020-68950-y
129. [129]
  X. Xiao, M. Lai, Z.H. Xie, et al., Eur. J. Med. Chem. 213 (2021) 113082. doi: 10.1016/j.ejmech.2020.113082
130. [130]
  B.A. Lanman, J.R. Allen, J.G. Allen, et al., J. Med. Chem. 63 (2020) 52–65. doi: 10.1021/acs.jmedchem.9b01180
131. [131]
  H.A. Blair, Drugs 81 (2021) 1573–1579. doi: 10.1007/s40265-021-01574-2
132. [132]
  A.T. Parsons, M. Beaver, PT WO 2021097212, 2021.
133. [133]
  A.E. Sorochinsky, T. Katagiri, T. Ono, et al., Chirality 25 (2013) 365–368. doi: 10.1002/chir.22180
134. [134]
  J. Han, D.J. Nelson, A.E. Sorochinsky, V.A. Soloshonok, Curr. Org. Synth. 8 (2011) 310–317. doi: 10.2174/157017911794697303
135. [135]
  A.E. Sorochinsky, J.L. Aceña, V.A. Soloshonok, Synthesis (Mass) 45 (2013) 141–152.
136. [136]
  J. Han, O. Kitagawa, A. Wzorek, K.D. Klika, V.A. Soloshonok, Chem. Sci. 9 (2018) 1718–1739. doi: 10.1039/c7sc05138g
137. [137]
  J. Han, A. Wzorek, K.D. Klika, V.A. Soloshonok, Molecules 26 (2021) 2757. doi: 10.3390/molecules26092757
138. [138]
  J. Han, R. Dembinski, V.A. Soloshonok, K.D. Klika, Molecules 26 (2021) 3994. doi: 10.3390/molecules26133994
1. [1]
  Qian Wang , Yeping Bian , Gagan Dhawan , Wei Zhang , Alexander E. Sorochinsky , Ata Makarem , Vadim A. Soloshonok , Jianlin Han . FDA approved fluorine-containing drugs in 2023. Chinese Chemical Letters, 2024, 35(11): 109780-. doi: 10.1016/j.cclet.2024.109780
2. [2]
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3. [3]
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4. [4]
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5. [5]
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6. [6]
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7. [7]
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8. [8]
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9. [9]
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10. [10]
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11. [11]
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12. [12]
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13. [13]
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14. [14]
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15. [15]
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16. [16]
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17. [17]
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18. [18]
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19. [19]
  Jingqi Ma , Huangjie Lu , Junpu Yang , Liangwei Yang , Jian-Qiang Wang , Xianlong Du , Jian Lin . Rational design and synthesis of a uranyl-organic hybrid for X-ray scintillation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100275-100275. doi: 10.1016/j.cjsc.2024.100275
20. [20]
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沈阳化工大学材料科学与工程学院沈阳 110142