Citation: Yingjie Yu, Aiyao Liu, Gagan Dhawan, Haibo Mei, Wei Zhang, Kunisuke Izawa, Vadim A. Soloshonok, Jianlin Han. Fluorine-containing pharmaceuticals approved by the FDA in 2020: Synthesis and biological activity[J]. Chinese Chemical Letters, ;2021, 32(11): 3342-3354. doi: 10.1016/j.cclet.2021.05.042 shu

Fluorine-containing pharmaceuticals approved by the FDA in 2020: Synthesis and biological activity

Yingjie Yu ^a ,
Aiyao Liu ^a ,
Gagan Dhawan ^{b, *,} ,
Haibo Mei ^a ,
Wei Zhang ^{c, *,} ,
Kunisuke Izawa ^d ,
Vadim A. Soloshonok ^{e, f, *,} ,
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, India
c.
Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, United States
d.
Hamari Chemical Ltd., 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka 533-0024, Japan
e.
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain
f.
IKERBASQUE, Basque Foundation for Science, María Díaz de Haro 3, Plaza Bizkaia, 48013 Bilbao, Spain

gagandhawan@andc.du.ac.in

wei2.zhang@umb.edu

vadym.soloshonok@ehu.es

hanjl@njfu.edu.cn

Received Date: 19 March 2021
Revised Date: 21 May 2021
Accepted Date: 21 May 2021
Available Online: 27 May 2021

Figures(22)

Thirteen new fluorine-containing drugs, which have been granted approval by the US Food and Drug Administration (FDA) in 2020, are profiled in this review. Therapeutic areas of these new fluorinated pharmaceuticals include medicines and diagnostic agents for Cushing's disease, neurofibromatosis, migraine, Alzheimer's disease, myelodysplastic syndromes, hereditary angioedema attacks, and various cancers. Molecules of these approved drugs feature aromatic fluorine (Ar-F) (11 compounds), aromatic Ar-CF₃ (1), aliphatic CHF (1) and CF₂ (1) groups. For each compound, we provide a spectrum of biological activity, medicinal chemistry discovery, and synthetic approaches.
- Fluorine and compounds,
- Blockbuster drugs,
- Modern pharmaceuticals,
- Synthesis,
- Drug design and development,
- Asymmetric synthesis
1. [1]
  (a) N. Aspern, S. Roser, B.R. Rad, et al., J. Fluorine Chem. 198 (2017) 24-33;
  (b) F. Gschwind, G. Rodriguez-Garcia, D.J.S. Sandbeck, et al., J. Fluorine Chem. 182 (2016) 76-90;
  (c) N. von Aspern, G.V. Roeschenthaler, M. Winter, I. Cekic-Laskovic, Angew. Chem. Int. Ed. 58 (2019) 15978-16000;
  (d) Y. Wang, W.H. Zhang, ChemElectroChem 2 (2015) 22-36;
  (e) T. Wang, X. Zang, X. Wang, et al., Energy Stor. Mater. 30 (2020) 367-384;
  (f) G.G. Amatucci, N. Pereira, J. Fluorine Chem. 128 (2007) 243-262;
  (g) W. Zhu, J.M. Alzola, T.J. Aldrich, et al., ACS Energy Lett. 4 (2019) 2695-2702;
  (h) T. Nakajima, J. Fluorine Chem. 105 (2000) 229-238;
  (i) Y. Che, X. Yuan, L. Sun, et al., J. Mater. Chem. C 8 (2020) 15839-15851;
  (j) X.B. Cheng, R. Zhang, C.Z. Zhao, et al., Adv. Sci. 3 (2016) 1500213.
2. [2]
  (a) T. Fujiwara, D. O'Hagan, J. Fluorine Chem. 167 (2014) 16-29;
  (b) M.G. Cagetti, G. Campus, E. Milia, P. Lingström, Acta Odontol. Scand. 71 (2013) 381-387;
  (c) Y. Lu, W.F. Guo, X.Q. Yang, J. Agric. Food Chem. 52 (2004) 4472-4476;
  (d) N.I. Sarker, M.S. Ahmad, S. Islam, N.H. Memon, Fluoride 53 (2020) 1-22;
  (e) L.A. Schaider, S.A. Balan, A. Blum, et al., Environ. Sci. Technol. Lett. 4 (2017) 105-111;
  (f) J. Cholak, J. Occup. Environ. Med. 1 (1959) 501-511;
  (g) Y. Ogawa, E. Tokunaga, O. Kobayashi, K. Hirai, N. Shibata, iScience 23 (2020) 101467.
3. [3]
  (a) T. Fujiwara, D. O'Hagan, J. Fluorine Chem. 167 (2014) 16-29;
  (b) D. O'Hagan, J. Fluorine Chem. 131 (2010) 1071-1081;
  (c) W. Zhu, J. Wang, S. Wang, et al., J. Fluorine Chem. 167 (2014) 37-54;
  (d) J. Wang, M. Sanchez-Rosello, J.L. Acena, et al., Chem. Rev. 114 (2014) 2432-2506;
  (e) Y. Zhou, J. Wang, Z. Gu, et al., Chem. Rev. 116 (2016) 422-518;
  (f) J. Han, L. Kiss, H. Mei, et al., Chem. Rev. 121 (2021) 4678-4742;
  (g) M.A. Miller, E.M. Sletten, ChemBioChem 21 (2020) 3451-3462;
  (h) S.J. Fomon, J. Ekstrand, E.E. Ziegler, J. Public. Health Dent. 60 (2000) 131-139;
  (i) A. Strunecká, J. Patočka, P. Connett, J. Appl. Biomed. 2 (2004) 141-150;
  (j) D. Kanduti, P. Sterbenk, B. Artnik, Mater. Sociomed. 28 (2016) 133-137;
  (k) P.T. Lowe, D. O'Hagan, J. Fluorine Chem. 230 (2020) 109420.
4. [4]
  (a) L. Wang, T. Kitamura, Y. Zhou, et al., J. Fluorine Chem. 240 (2020) 109670;
  (b) J. Han, G. Butler, H. Moriwaki, et al., Molecules 25 (2020) 2116;
  (c) H. Mei, J. Han, S. White, G. Butler, V.A. Soloshonok, J. Fluorine Chem. 227 (2019) 109370;
  (d) 2019 A. Sato, M.V. Ponomarenko, T. Ono, G.V. Röschenthaler, V.A. Soloshonok, Eur. J. Org. Chem. (2019) 4417-4421. 2019;
  (e) W. Zhang, Chem. Rev. 104 (2004) 2531-2556;
  (f) W.B. Yi, J.J. Ma, L.Q. Jiang, C. Cai, W. Zhang, J. Fluorine Chem. 157 (2014) 84-105;
  (g) A.J. Cresswell, S.G. Davies, P.M. Roberts, J.E. Thomson, Chem. Rev. 115 (2015) 566-611;
  (h) J. Charpentier, N. Früh, A. Togni, Chem. Rev. 115 (2015) 650-682;
  (i) X. Liu, C. Xu, M. Wang, Q. Liu, Chem. Rev. 115 (2015) 683-730;
  (j) X.H. Xu, K. Matsuzaki, N. Shibata, Chem. Rev. 115 (2015) 731-764;
  (k) V.G. Nenajdenko, V.M. Muzalevskiy, A.V. Shastin, Chem. Rev. 115 (2015) 973-1050.
5. [5]
  (a) M.G. Campbell, T. Ritter, Chem. Rev. 115 (2015) 612-633;
  (b) L. Wang, Z. Li, J. Liu, et al., Curr. Org. Chem. 24 (2020) 2181-2191;
  (c) J. Liu, Z. Li, H. Mei, V.A. Soloshonok, J. Han, ACS Omega 4 (2019) 19505-19512;
  (d) H. Mei, J. Liu, S. Fustero, et al., Org. Biomol. Chem. 17 (2019) 762-775;
  (e) H. Mei, J. Han, S. Fustero, et al., J. Fluorine Chem. 216 (2018) 57-70;
  (f) Y. Zhu, J.L. Han, J. Wang, et al., Chem. Rev. 118 (2018) 3887-3964;
  (g) L. Zhang, W. Zhang, W. Sha, et al., J. Fluorine Chem. 198 (2017) 2-9;
  (h) J. Han, A.E. Sorochinsky, T. Ono, V.A. Soloshonok, Curr. Org. Synth. 8 (2011) 281-294;
  (i) J.L. Aceña, A.E. Sorochinsky, H. Moriwaki, T. Sato, V.A. Soloshonok, J. Fluorine Chem. 155 (2013) 21-38.
6. [6]
  (a) E. Tokunaga, H. Akiyama, V.A. Soloshonok, et al., PLoS ONE 12 (2017) e0182152;
  (b) A.E. Sorochinsky, T. Katagiri, T. Ono, et al., Chirality 25 (2013) 365-368;
  (c) A.E. Sorochinsky, J.L. Aceña, V.A. Soloshonok, Synthesis 45 (2013) 141-152;
  (d) D. O'Hagan, H. Deng, Chem. Rev. 115 (2015) 634-649;
  (e) I. Tirotta, V. Dichiarante, C. Pigliacelli, et al., Chem. Rev. 115 (2015) 1106-1129;
  (f) R. Hoque, A.L. Chesson, J. Clin. Sleep Med. 5 (2009) 471-476;
  (g) P. Venkateswarlu, Adv. Dent. Res. 8 (1994) 80-86;
  (h) X.G. Li, M. Haaparanta, O. Solin, J. Fluorine Chem. 143 (2012) 49-56;
  (i) M. Houde, J.W. Martin, R.J. Letcher, K.R. Solomon, D.C.G. Muir, Environ. Sci. Technol. 40 (2006) 3463-3473;
  (j) J. Yang, R. Zhang, Y. Zhao, et al., Spectrochim. Acta A 248 (2021) 119199.
7. [7]
  (a) H. Mei, J. Han, S. White, et al., Chem. Eur. J. 26 (2020) 11349-11390;
  (b) H. Mei, J. Han, K.D. Klika, et al., Eur. J. Med. Chem. 186 (2020) 111826;
  (c) J. Han, A.M. Remete, L.S. Dobson, L. Kiss, K. Izawa, H. Moriwaki, V.A. Soloshonok, D. O'Hagan, J. Fluorine Chem. 239 (2020) 109639;
  (d) K.L. Kirk, J. Fluorine Chem. 127 (2006) 1013-1029;
  (e) E.P. Gillis, K.J. Eastman, M.D. Hill, D.J. Donnelly, N.A. Meanwell, J. Med. Chem. 58 (2015) 8315-8359;
  (f) W.K. Hagmann, J. Med. Chem. 51 (2008) 4359-4369;
  (g) M. Inoue, Y. Sumii, N. Shibata, ACS Omega 5 (2020) 10633-10640;
  (h) R. Hevey, Chem. Eur. J. 27 (2021) 2240-2253;
  (i) M. Shevchuk, Q. Wang, R. Pajkert, et al., Adv. Synth. Catal. (2021), doi: 10.1002/adsc.202001464.
8. [8]
  H. Mei, J. Han, S. Fustero, et al., Chem. Eur. J. 25 (2019) 11797-11819. doi: 10.1002/chem.201901840
9. [9]
  H. Mei, A.M. Remete, Y. Zou, et al., Chin. Chem. Lett. 31 (2020) 2401-2413. doi: 10.1016/j.cclet.2020.03.050
10. [10]
  B.L. Hodous, J.L. Kim, K.J. Wilson, D. Wilson, WO2015057873 A1, 2015.
11. [11]
  (a) E.K. Evans, A.K. Gardino, J.L. Kim, et al., Sci. Transl. Med. 9 (2017) 1690 eaao;
  (b) E.K. Evans, A. Gardino, B. Hodous, et al., Blood 126 (2015) 568.
12. [12]
  S. Dhillon, Drugs 80 (2020) 433-439. doi: 10.1007/s40265-020-01275-2
13. [13]
  X. Xu, CN111454217 A, 2020.
14. [14]
  R. Shintani, M. Takeda, T. Tsuji, T. Hayashi, J. Am. Chem. Soc. 132 (2010) 13168-13169. doi: 10.1021/ja106114q
15. [15]
  Y. Xu, Y. Yu, Z. Fan, L. Chen, CN110950872 A, 2020.
16. [16]
  B.L. Hodous, US2016/0031892 A1, 2016.
17. [17]
  K.L. Meredith, G. Ksander, L.G. Monovich, et al., ACS Med. Chem. Lett. 4 (2013) 1203-1207. doi: 10.1021/ml400324c
18. [18]
  J. Ménard, L. Pascoe, J. Hypertens. 24 (2006) 993-997. doi: 10.1097/01.hjh.0000226183.98439.b3
19. [19]
  S. Duggan, Drugs 80 (2020) 495-500. doi: 10.1007/s40265-020-01277-0
20. [20]
  C. Zhang, J. Chakma, WO2016/109361 A2, 2016.
21. [21]
  (a) A.E. Sorochinsky, J.L. Aceña, V.A. Soloshonok, Synthesis 45 (2013) 141-152;
  (b) J. Han, O. Kitagawa, A. Wzorek, K.D. Klika, V.A. Soloshonok, Chem. Sci. 9 (2018) 1718-1739;
  (c) V.A. Soloshonok, D.O. Berbasov, Chim. Oggi. Chem. Today 24 (2006) 44-47.
22. [22]
  (a) A.E. Sorochinsky, T. Katagiri, T. Ono, et al., Chirality 25 (2013) 365-368;
  (b) T. Nakamura, K. Tateishi, S. Tsukagoshi, et al., Tetrahedron 68 (2012) 4013-4017;
  (c) Y. Suzukia, J. Han, O. Kitagawa, J.L. Aceñac, K.D. Klika, V.A. Soloshonok, RSC Adv. 5 (2015) 2988-2993.
23. [23]
  J.L. Aceña, A.E. Sorochinsky, T. Katagiri, V.A. Soloshonok, Chem. Commun. 49 (2013) 373-375. doi: 10.1039/C2CC37491A
24. [24]
  T. Katagiri, S. Takahashi, A. Tsuboi, M. Suzaki, K. Uneyama, J. Fluorine Chem. 131 (2010) 517-520. doi: 10.1016/j.jfluchem.2009.12.007
25. [25]
  (a) H. Ueki, M. Yasumoto, V.A. Soloshonok, Tetrahedron 21 (2010) 1396-1400;
  (b) M. Yasumoto, H. Ueki, T. Ono, T. Katagiri, V.A. Soloshonok, J. Fluorine Chem. 131 (2010) 535-539;
  (c) M. Yasumoto, H. Ueki, V.A. Soloshonok, J. Fluorine Chem. 131 (2010) 266-269;
  (d) M. Yasumoto, H. Ueki, V.A. Soloshonok, J. Fluorine Chem. 131 (2010) 540-544;
  (e) J. Han, D.J. Nelson, A.E. Sorochinsky, V.A. Soloshonok, Curr. Org. Synth. 8 (2011) 310-317;
  (f) V.A. Soloshonok, A. Wzorek, K.D. Klika, Tetrahedron 28 (2017) 1430-1434.
26. [26]
  A. Markham, Keam S.J., Drugs 80 (2020) 931-937. doi: 10.1007/s40265-020-01331-x
27. [27]
  E.L. Wallace, J.P. Lyssikatos, B.T. Hurley, A.L. Marlow, WO03077914, A1, 2003.
28. [28]
  B.R. Davies, A. Logie, J.S. McKay, et al., Mol. Cancer Ther. 6 (2007) 2209-2219. doi: 10.1158/1535-7163.MCT-07-0231
29. [29]
  C.J. Squire, J. Demattei, R.J. Boberts, WO2007076245 A2, 2007.
30. [30]
  P.C.C. Liu, K. Holly, L. Wu, et al., PLoS ONE 15 (2020) e0231877. doi: 10.1371/journal.pone.0231877
31. [31]
  L. Wu, C. Zhang, C. He, et al., WO2014007951 A2 (2014).
32. [32]
  S.M. Hoy, Drugs 80 (2020) 923-929. doi: 10.1007/s40265-020-01330-y
33. [33]
  T.C. Burn, P.C. Liu, W. Frietze, et al., WO2019/213544 A2, 2019.
34. [34]
  U. Glaenzel, Y. Jin, R. Hansen, et al., Drug Metab. Dispos. 48 (2020) 873-885. doi: 10.1124/dmd.119.090324
35. [35]
  M. Xu, C. He, C. Zhang, WO2008/64157 A1, 2008.
36. [36]
  J. Zhuo, C. He, W. Yao, US US2011/212967 A1, 2011.
37. [37]
  S. Dhillon, Drugs 80 (2020) 1125-1131. doi: 10.1007/s40265-020-01347-3
38. [38]
  D.L. Flynn, M.D. Kaufman, WO 2013/184119 A1, 2013.
39. [39]
  D.L. Flynn, M.D. Kaufman, P.A. Petillo, US 8461179 B1, 2013.
40. [40]
  S. Dhillon, Drugs 80 (2020) 1133-1138. doi: 10.1007/s40265-020-01348-2
41. [41]
  G. Luo, L. Chen, C.M. Conway, et al., J. Med. Chem. 55 (2012) 10644-10651. doi: 10.1021/jm3013147
42. [42]
  (a) J. Liu, J. Han, K. Izawa, et al., Eur. J. Med. Chem. 208 (2020) 112736;
  (b) Z. Yin, W. Hu, W. Zhang, et al., Amino Acids 52 (2020) 1227-1261.
43. [43]
  G. Luo, L. Chen, C.M. Conway, et al., ACS Med. Chem. Lett. 3 (2012) 337-341. doi: 10.1021/ml300021s
44. [44]
  L.J. Scott, Drugs 80 (2020) 741-746. doi: 10.1007/s40265-020-01301-3
45. [45]
  G. Luo, GM. Bubowchik, J.E. Macor, WO 2011046997 A1, 2011.
46. [46]
  D.K. Leahy, Y. Fan, L.V. Desai, et al., Org. Lett. 14 (2012) 4938-4941. doi: 10.1021/ol302262q
47. [47]
  (a) B.K. Park, N.R. Kitteringham, P.M. O'Neill, Annu. Rev. Pharmacol. Toxicol. 41 (2001) 443-470;
  (b) G.J. Liao, A.S. Clark, E.K. Schubert, D.A. Mankoff, J. Nucl. Med. 57 (2016) 1269-1275.
48. [48]
  (a) W. Li, Int. Congr. Ser. 1264 (2004) 53-76;
  (b) R.M. Glasspool, T.R.J. Evans, Eur. J. Cancer 36 (2000) 1661-1670;
  (c) L. Varagnolo, M.P.M. Stokkel, U. Mazzi, E.K.J. Pauwels, Nucl. Med. Biol. 27 (2000) 103-112;
  (d) M.J. Adam, D.S. Wilbur, Chem. Soc. Rev. 34 (2004) 153-163.
49. [49]
  (a) L.M. Peterson, D.A. Mankoff, T. Lawton, et al., J. Nucl. Med. 49 (2008) 367-374;
  (b) M. Paquette, É. Lavallée, S. Phoenix, et al., J. Nucl. Med. 59 (2018) 197-203.
50. [50]
  S.Y. Chae, S.H. Ahn, S.B. Kim, et al., Lancet Oncol 20 (2019) 546-555. doi: 10.1016/S1470-2045(18)30936-7
51. [51]
  L.M. Peterson, B.F. Kurland, E.K. Schubert, et al., Mol. Imaging Biol. 16 (2014) 431-440. doi: 10.1007/s11307-013-0699-7
52. [52]
  D.O. Kiesewetter, M.R. Kilbourn, S.W. Landvatter, et al., J. Nucl. Med. 25 (1984) 1212-1221.
53. [53]
  (a) P. Kumar, P.J. Mercer, C. Doerkson, K. Tonkin, A.J. McEwan, J. Pharm. Pharm. Sci. 10 (2007) 256s-265s;
  (b) J.L. Lim, L. Zheng, M.S. Berridge, T.J. Tewson, Nucl. Med. Biol. 23 (1996) 911-915.
54. [54]
  M. Dixit, J. Shi, L. Wei, G. Afari, S. Bhattacharyya, Int. J. Mol. Imaging (2013) 2786072013.
55. [55]
  M. Schöll, A. Maass, N. Mattsson, et al., Mol. Cell. Neurosci. 97 (2019) 18-33. doi: 10.1016/j.mcn.2018.12.001
56. [56]
  V.L. Villemagne, M.T. Fodero-Tavoletti, C.L. Masters, C.C. Rowe, Lancet Neurol. 14 (2015) 114-124. doi: 10.1016/S1474-4422(14)70252-2
57. [57]
  B. Hall, E. Mak, S. Cervenka, et al., Ageing Res. Rev. 36 (2017) 50-63. doi: 10.1016/j.arr.2017.03.002
58. [58]
  A. Leuzy, K. Chiotis, L. Lemoine, et al., Mol. Psychiatry 24 (2019) 1112-1134. doi: 10.1038/s41380-018-0342-8
59. [59]
  (a) G.J. Liao, A.S. Clark, E.K. Schubert, D.A. Mankoff, J. Nucl. Med. 57 (2016) 1269-1275;
  (b) Y.T. Wang, P. Edison, Curr. Neurol. Neurosci. Rep. 19 (2019) 45.
60. [60]
  D.P. Holt, H.T. Ravert, R.F. Dannals, J. Label. Compd. Radiopharm. 59 (2016) 411-415. doi: 10.1002/jlcr.3425
61. [61]
  A.V. Mossine, A.F. Brooks, B.D. Henderson, et al., EJNMMI Radiopharm. Chem. 2 (2017) 7. doi: 10.1186/s41181-017-0027-7
62. [62]
  (a) E. Jabbour, J.P. Issa, G. Garcia-Manero, H. Kantarjian, Cancer 112 (2008) 2341-2351;
  (b) K. Ueda, A. Masuda, M. Fukuda, et al., Drug Metab. Pharmacokinet. 32 (2017) 301-310;
  (c) M. Duchmann, R. Itzykson, Int. J. Hematol. 110 (2019) 161-169.
63. [63]
  S. Belyakov, G.S. Hamilton, B. Duvall, D. Ferraris, M. Vaal, AU2016213880B2, 2016.
64. [64]
  (a) G.W. Camiener, Biochem. Pharmacol. 61 (1967) 1691-1702;
  (b) H. Hosono, S. Kuno, J. Biochem. 74 (1973) 797-803.
65. [65]
  A.H. Teh, M. Kimura, M. Yamamoto, et al., Biochemistry 45 (2006) 7825-7833. doi: 10.1021/bi060345f
66. [66]
  S. Costanzi, S. Vilar, D. Micozzi, et al., ChemMedChem 6 (2011) 1452-1458. doi: 10.1002/cmdc.201100139
67. [67]
  D. Ferraris, B. Duvall, G. Delahanty, et al., J. Med. Chem. 57 (2014) 2582-2588. doi: 10.1021/jm401856k
68. [68]
  (a) A. Oganesian, S. Redkar, P. Taverna, G. Choy, R. Joshi-Hangal, M. Azab, Blood 122 (2013) 2526;
  (b) M.R. Savona, O. Odenike, P.C. Amrein, et al., Lancet Haematol. 6 (2019) e194-e203;
  (c) G. Garcia-Manero, E.A. Griffiths, D.P. Steensma, et al., Blood 136 (2020) 674-683.
69. [69]
  S. Dhillon, S. Drugs 80 (2020) 1373-1378. doi: 10.1007/s40265-020-01389-7
70. [70]
  (a) J. Norton, H. Matsuo, S.J. Sturla, J. Org. Chem. 74 (2009) 2221-2223;
  (b) M.S. Kim, Y.J. Kim, J.H. Choi, H.G. Lim, D.W. Cha, WO2007/069838A1 (2007).
71. [71]
  (a) Jr G.Y. Ku, B.A. Haaland, G. de Lima Lopes, Lung Cancer 74 (2011) 469-473;
  (b) S.G. O'Brien, F. Guilhot, R.A. Larson, et al., New Engl. J. Med. 348 (2003) 994-1004;
  (c) A.T. Shaw, D.W. Kim, K. Nakagawa, et al., New Engl. J. Med. 368 (2013) 2385-2394;
  (d) C. Zhou, Y.L. Wu, G. Chen, et al., Lancet Oncol. 12 (2011) 735-742.
72. [72]
  (a) J.C. Soria, Y. Ohe, J. Vansteenkiste, et al., New Engl. J. Med. 378 (2018) 113-125;
  (b) J.J. Lin, A.T. Shaw, Trends Cancer 2 (2016) 350-364;
  (c) J.F. Gaino, A.T. Shaw, J. Clin. Oncol. 31 (2013) 3987-3996;
  (d) S. Peters, D.R. Camidg, A.T. Shaw, et al., New Engl. J. Med. 377 (2017) 829-838;
  (e) E. Jabbour, H. Kantarjian, J. Cortes Clin, Lymphoma Myeloma Leuk 15 (2015) 323-334.
73. [73]
  (a) J.F. Gainor, J.F. Shaw, Genome. Res. 3 (2013) 604-606;
  (b) Y.S. Ju, W.C. Lee, J.Y. Shin, et al., Genome. Res. 22 (2012) 436-445;
  (c) T. Kohno, H. Ichikawa, Y. Totoki, et al., Nat. Med. 18 (2012) 375-377;
  (d) N. Stransky, E. Cerami, S. Schalm, J.L. Kim, C. Lengauer, Nat. Commun. 5 (2014) 4846-4856;
  (e) P. Ballerini, S. Struski, C. Cresson, et al., Leukemia 26 (2012) 2384-2389;
  (f) A.F. Le Rolle, S.J. Klempner, C.R. Garrett, et al., Oncotarget 6 (2015) 28929-28937;
  (g) A. Skalova, G. Stenman, R.H.W. Simpson, et al., Am. J. Surg. Pathol. 42 (2018) e11-e27.
74. [74]
  M. Takahashi, J. Ritz, G.M. Cooper, Cell 42 (1985) 581-588. doi: 10.1016/0092-8674(85)90115-1
75. [75]
  S.M. Jhiang, Oncogene 19 (2000) 5590-5597. doi: 10.1038/sj.onc.1203857
76. [76]
  A. Russo, A.R. Lopes, M.G. McCusker, et al., Curr. Oncol. Rep. 22 (2020) 48. doi: 10.1007/s11912-020-00909-8
77. [77]
  V. Subbiah, J.F. Gainor, R. Rahal, et al., Cancer Discov. 8 (2018) 836-849. doi: 10.1158/2159-8290.CD-18-0338
78. [78]
  V. Subbiah, D. Yang, V. Velcheti, A. Drilon, F. Meric-Bernstam, J. Clin. Oncol. 38 (2020) 1209-1221. doi: 10.1200/JCO.19.02551
79. [79]
  J.D. Brubaker, J.L. Kim, K.J. Wilson, D. Wilson, L.V. Dipietro, WO2017079140, 2017.
80. [80]
  J.H. Levy, D.J. Freiberger, J. Roback, Anesth. Analg. 110 (2010) 1271-1280. doi: 10.1213/ANE.0b013e3181d7ac98
81. [81]
  (a) J.W. Bryant, Z. Shariat-Madar, Cardiovasc. Hematol. Agents Med. Chem. 3(3) (2009) 234-250;
  (b) A.P. Kaplan, World Allergy Organ J. 4 (2011) 73-75;
  (c) A.H. Schmaier, Front. Med. (Lausanne) 5 (2018) 3.
82. [82]
  (a) Z. Xie, Z. Li, Y. Shao, C. Liao, Eur. J. Med. Chem. 190 (2020) 112137;
  (b) Z. Li, J. Partridge, A. Silva-Garcia, et al., ACS Med. Chem. Lett. 8 (2016) 185-190.
83. [83]
  E. Aygören-Pürsün, M. Magerl, J. Graff, et al., J. Allergy Clin. Immunol. 138 (2016) e5934-936.
84. [84]
  T. Brandl, S. Flohr, S. Kopec, et al., WO2012017020A1 (2012).
85. [85]
  (a) J.R. Hwang, G. Hwang, A. Johri, T. Craig, Immunotherapy 17 (2019) 1439-1444;
  (b) E. Aygören-Pürsün, A. Bygum, V. Grivcheva-Panovska, et al., N. Engl. J Med. 379 (2018) 352-362.
86. [86]
  Y. El-Kattan, Y.S. Babu, WO2020092898A1, 2019.
87. [87]
  N. Das, T.R. Kumar, J. Mol. Endocrinol. 60 (2018) R131-R155. doi: 10.1530/JME-17-0308
88. [88]
  (a) T.D. Fitapatrick, J. Green, F. Haviv, C.A. Palabrica, US5140009, 1992;
  (b) T. Janaky, A. Juhasz, A.V. Schally, US5171835A, 1992.
89. [89]
  K. Kato, Y. Sugiura, K. Kato, US5633248, 1997.
90. [90]
  R.J. Bienstock, J. Rizo, S.C. Koerber, et al., J. Med. Chem. 36 (1993) 3265-3273. doi: 10.1021/jm00074a006
91. [91]
  (a) P. Limonta, M. Montagnani M. Marelli, S. Mai, et al., Endocr. Rev. 33 (2012) 784-811;
  (b) P. Limonta, M. Manea, Cancer Treat. Rev. 39 (2013) 647-663.
92. [92]
  (a) S. Furuya, N. Choh, K. Kato, S. Hinuma, WO95/28405, 1995;
  (b) S. Furuya, N. Choh, K. Kato, S. Hinuma, WO96/24597, 1996;
  (c) S. Furuya, N. Choh, S. Sasaki, WO97/14682, 1997;
  (d) S. Furuya, N. Choh, M. Harada, S. Sasaki, WO97/14697, 1997;
  (e) S. Furuya, T. Imaeda, S. Sasaki, WO99/33831, 1999;
  (f) S. Furuya, N. Choh, N. Suzuki, T. Imada, WO00/00493, 2000;
  (g) S. Furuya, N. Suzuki, N. Choh, Y. Nara, WO00/56739, 2000.
93. [93]
  B. De, J.J. Plattner, E.N. Bush, et al., J. Med. Chem. 32 (1989) 2036-2038. doi: 10.1021/jm00129a003
94. [94]
  N. Cho, T. Imada, T. Hitaka, et al., US7300935B2, 2007.
95. [95]
  K. Miwa, T. Hitaka, T. Imada, et al., J. Med. Chem. 54 (2011) 4998-5012. doi: 10.1021/jm200216q
96. [96]
  F.L. Tukun, D.E. Olberg, P.J. Riss, I. Haraldsen, A. Kaass, J. Klaveness, Mol. 22 (2017) 2188. doi: 10.3390/molecules22122188
97. [97]
  A. Markham, Drugs 79 (2019) 675-679. doi: 10.1007/s40265-019-01105-0
98. [98]
  (a) Y.N. Lamb, Drugs 78 (2018) 1501-1508;
  (b) "Elagolix-Abbvie/Neurocrine Biosciences-AdisInsight" (https://adisinsight.springer.com/drugs/800020238).
99. [99]
  T. Hara, H. Araki, M. Kusaka, et al., J. Clin. Endocrinol. Metab. 88 (2003) 1697-1704. doi: 10.1210/jc.2002-021065
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