Covalent epidermal growth factor receptor (EGFR) inhibitors in targeted therapy of drug-resistant non-small cell lung cancer

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Non-small cell lung cancer (NSCLC) is the main subtype of lung cancer and is a common cause of cancer-related mortality worldwide. Mutations in the epidermal growth factor receptor (EGFR) gene play a leading role in the pathogenesis of NSCLC, causing its pathological activity. The first generation of EGFR inhibitors, acting reversibly, effectively block the effects of EGFR with activating mutations by benefiting from competition with adenosine triphosphate for binding to the kinase. However, after several months of treatment, a secondary T790M mutation often occurs, causing resistance to subsequent therapy with these drugs. Effective inhibition of EGFR with the T790M mutation was possible due to second-generation inhibitors acting via a covalent mechanism. However, the second generation of covalent inhibitors has received limited use in therapy due to insufficient selectivity for EGFR T790M and a narrow therapeutic window. The discovery of covalent pyrimidine-based inhibitors has led to the emergence of a number of effective and safer third-generation drugs for the treatment of NSCLC with the EGFR T790M mutation. This review contains a brief description of first- and second-generation EGFR inhibitors and a detailed discussion of the main stages in the development of third-generation inhibitors. The main emphasis is placed on the identified “structure–activity” patterns. Data are provided on inhibitors that have received the status of approved drugs for the treatment of NSCLC. Promising directions for the development of novel EGFR inhibitors are indicated.

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A. Shvetsov

National Research Ogarev Mordovia State University

编辑信件的主要联系方式.
Email: shvetsov.1984@list.ru
俄罗斯联邦, ul. Bolshevistskaya 68, Saransk, 430005

A. Semenov

National Research Ogarev Mordovia State University

Email: shvetsov.1984@list.ru
俄罗斯联邦, ul. Bolshevistskaya 68, Saransk, 430005

参考

  1. Состояние онкологической помощи населению России в 2022 году / Под ред. Каприна А.Д., Старинского В.В., Шахзадовой А.О. М: МНИОИ им. П.А. Герцена, филиал ФГБУ “НМИЦ радиологии” МЗ РФ, 2022. С. 28.
  2. Злокачественные новообразования в России в 2021 году (заболеваемость и смертность) / Под ред. Каприна А.Д., Старинского В.В., Шахзадовой А.О. М: МНИОИ им. П.А. Герцена, филиал ФГБУ “НМИЦ радиологии” МЗ РФ, 2022. С. 5.
  3. Chunhacha P., Chanvorachote P. // Int. J. Physiol. Pathophysiol. Pharmacol. 2012. V. 4. P. 149–155. https://pubmed.ncbi.nlm.nih.gov/23071872/
  4. Stamos J., Sliwkowski M., Eigenbrot C. // J. Biol. Chem. 2002. V. 277. P. 46265–46272. https://doi.org/10.1074/jbc.M207135200
  5. Amelia T. // Molecules. 2022. V. 27. P. 819. https://doi.org/10.3390/molecules27030819
  6. Yun C.-H., Boggon T., Li Y., Woo M., Greulich H., Meyerson M., Eck M. // Cancer Cell. 2007. V. 11. P. 217–227. https://doi.org/10.1016/j.ccr.2006.12.017
  7. Sharma S., Bell D., Settleman J., Haber D. // Nat. Rev. Cancer. 2007. V. 7. P. 169–181. https://doi.org/10.1038/nrc2088
  8. Castellanos E.H., Horn L. // Curr. Treat. Options Oncol. 2015. V. 16. Р. 51. https://doi.org/10.1007/s11864-015-0365-1
  9. Elzahabi H., Nossier E., Alasfoury R., El-Manawaty M., Sayed S., Elkaeed E., Metwaly A., Hagras M., Eissa I. // J. Enzyme Inhib. Med. Chem. 2022. V. 37. Р. 1053– 1076. https://doi.org/10.1080/14756366.2022.2062752
  10. Karachaliou N., Fernandez-Bruno M., Bracht J., Rosell R. // Transl. Cancer Res. 2019. V. 8. P. S23–S47. https://doi.org/10.21037/tcr.2018.10.06
  11. Ko B., Paucar D., Halmos B. // Lung Cancer (Auckl). 2017. V. 8. Р. 147–159. https://doi.org/10.2147/lctt.s117944
  12. Eck M., Yun C.-H. // Biochim. Biophys. Acta. 2010. V. 1804. P. 559–566. https://doi.org/10.1016/j.bbapap.2009.12.010
  13. Yver A. // Ann. Oncol. 2016. V. 27. P. 1165–1170. https://doi.org/10.1093/annonc/mdw129
  14. Ward R., Goldberg F. // Kinase Drug Discovery. Royal Society of Chemistry, 1th ed., 2011. P. 332. https://doi.org/10.1039/9781849733557
  15. Engelman J., Zejnullahu K., Gale C., Lifshits E., Gonzales A., Shimamura T., Zhao F., Vincent P., Naumov G., Bradner J., Althaus I., Gandhi L., Shapiro G., Nelson J., Heymach J., Meyerson M., Wong K., Jänne P. // Cancer Res. 2007. V. 67. P. 11924–11932. https://doi.org/10.1158/0008-5472.can-07-1885
  16. Li D., Ambrogio L., Shimamura T., Kubo S., Takahashi M., Chirieac L., Padera R., Shapiro G., Baum A., Himmelsbach F., Rettig W., Meyerson M., Solca F., Greulich H., Wong K. // Oncogene. 2008. V. 27. P. 4702– 4711. https://doi.org/10.1038/onc.2008.109
  17. Solca F., Dahl G., Zoephel A., Bader G., Sanderson M., Klein C., Kraemer O., Himmelsbach F., Haaksma E., Adolf G. // J. Pharmacol. Exp. Ther. 2012. V. 343. P. 342–350. https://doi.org/10.1124/jpet.112.197756
  18. Katakami N., Atagi S., Goto K., Hida T., Horai T., Inoue A., Ichinose Y., Koboyashi K., Takeda K., Kiura K., Nishio K., Seki Y., Ebisawa R., Shahidi M., Yamamoto N. // J. Clin. Oncol. 2013. V. 31. P. 3335– 3341. https://doi.org/10.1200/jco.2012.45.0981
  19. Kwak E., Sordella R., Bell D., Godin-Heymann N., Okimoto R., Brannigan B., Harris P., Driscoll D., Fidias P., Lynch T., Rabindran S., McGinnis J., Wissner A., Sharma S., Isselbacher K., Settleman J., Haber D. // Proc. Natl. Acad. Sci. USA. 2005. V. 102. P. 7665–7670. https://doi.org/10.1073/pnas.0502860102
  20. Sequist L., Besse B., Lynch T., Miller V., Wong K., Gitlitz B., Eaton K., Zacharchuk C., Freyman A., Powell C., Ananthakrishnan R., Quinn S., Soria J.-C. // J. Clin. Oncol. 2010. V. 28. P. 3076–3083. https://doi.org/10.1200/jco.2009.27.9414
  21. Yun C.-H., Mengwasser K., Toms A., Woo M., Greulich H., Wong K.-K., Meyerson M., Eck M. // Proc. Natl. Acad. Sci. USA. 2008. V. 105. P. 2070–2075. https://doi.org/10.1073/pnas.0709662105
  22. Kalous O., Conklin D., Desai A., O’Brien N., Ginther C., Anderson L., Cohen D., Britten C., Taylor I., Christensen J., Slamon D., Finn R. // Mol. Cancer Ther. 2012. V. 11. P. 1978–1987. https://doi.org/10.1158/1535-7163.MCT-11-0730
  23. Yoshimura N., Kudoh S., Kimura T., Mitsuoka S., Matsuura K., Hirata K., Matsui K., Negoro S., Nakagawa K., Fukuoka M. // Lung Cancer. 2006. V. 51. P. 363–368. https://doi.org/10.1016/j.lungcan.2005.10.006
  24. Jänne P., Pawel J., Cohen R., Crino L., Butts C., Olson S., Eiseman I., Chiappori A., Yeap B., Lenehan P., Dasse K., Sheeran M., Bonomi P. // J. Clin. Oncol. 2007. V. 25. P. 3936–3944. https://doi.org/10.1200/JCO.2007.11.1336
  25. Ghosh A., Samanta I., Mondal A., Liu W. // Chem. Med. Chem. 2019. V. 14. P. 889–906. https://doi.org/10.1002/cmdc.201900107
  26. Yu H., Riely G. // J. Natl. Compr. Canc. Netw. 2013. V. 11. P. 161–169. https://doi.org/10.6004/jnccn.2013.0024
  27. Zhou W., Ercan D., Chen L., Yun C.-H., Li D., Capelletti M., Cortot A., Chirieac L., Iacob R., Padera R., Engen J., Wong K.-K., Eck M., Gray N., Jänne P. // Nature. 2009. V. 462. P. 1070–1074. https://doi.org/10.1038/nature08622
  28. Sjin R., Lee K., Walter A., Dubrovskiy A., Sheets M., Martin T., Labenski M., Zhu Z., Tester R., Karp R., Medikonda A., Chaturvedi P., Ren Y., Haringsma H., Etter J., Raponi M., Simmons A., Harding T., Niu D., Nacht M., Westlin W., Petter R., Allen A., Singh J. // Mol. Cancer Ther. 2014. V. 13. P. 1468–1479. https://doi.org/10.1158/1535-7163.mct-13-0966
  29. Walter A., Sjin R., Haringsma H., Ohashi K., Sun J., Lee K., Dubrovskiy A., Labenski M., Zhu Z., Wang Z., Sheets M., Martin T., Karp R., Kalken D., Chaturvedi P., Niu D., Nacht M., Petter R., Westlin W., Lin K., Jaw-Tsai S., Raponi M., Dyke T., Etter J., Weaver Z., Pao W., Singh J., Simmons A., Harding T., Allen A. // Cancer Discov. 2013. V. 3. P. 1404–1415. https://doi.org/10.1158/2159-8290.cd-13-0314
  30. Yan X.-E., Zhu S.-J., Liang L., Zhao P., Choi H., Yun C.-H. // Oncotarget. 2018. V. 9. P. 13652–13665. https://doi.org/10.18632%2Foncotarget.18588
  31. Van Der Steen N., Caparello C., Rolfo C., Pauwels P., Peters G., Giovannetti E. // Onco Targets Ther. 2016. V. 9. P. 6065–6074. https://doi.org/10.2147/ott.s97644
  32. Simmons A., Jaw-Tsai S., Haringsma H., Allen A., Harding T. // Cancer Res. 2015. V. 75. P. 793. https://doi.org/10.1158/1538-7445.AM2015-793
  33. Dhingra K. // Ann. Oncol. 2016. V. 27. P. 1161–1164. https://doi.org/10.1093/annonc/mdw140
  34. Finlay M.R., Anderton M., Ashton S., Ballard P., Bethel P., Box M., Bradbury R., Brown S., Butterworth S., Campbell A., Chorley C., Colclough N., Cross D., Currie G.S., Grist M., Hassall L., Hill G., James D., James M., Kemmitt P., Klinowska T., Lamont G., Lamont S., Martin N., McFarland H., Mellor M., Orme J., Perkins D., Perkins P., Richmond G., Smith P., Ward R., Waring M., Whittaker D., Wells S., Wrigley G. // J. Med. Chem. 2014. V. 57. P. 8249–8267. https://doi.org/10.1021/jm500973a
  35. Cross D., Ashton S., Ghiorghiu S., Eberlein C., Nebhan C., Spitzler P., Orme J., Finlay M.R., Ward R., Mellor M., Hughes G., Rahi A., Jacobs V., Brewer M., Ichihara E., Sun J., Jin H., Ballard P., Al-Kadhimi K., Rowlinson R., Klinowska T., Richmond G., Cantarini M., Kim D.-W., Ranson M., Pao W. // Cancer Discov. 2014. V. 4. P. 1046–1061. https://doi.org/10.1158/2159-8290.cd-14-0337
  36. Yan X.-E., Ayaz P., Zhu S.-J., Zhao P., Liang L., Zhang C., Wu Y.-C., Li J.-L., Choi H.-G., Huang X., Shan Y., Shaw D., Yun C.-H. // J. Med. Chem. 2020. V. 63. P. 8502−8511. https://doi.org/10.1021/acs.jmedchem.0c00891
  37. Mah R., Thomas J., Shafer C. // Bioorg. Med. Chem. Lett. 2014. V. 24. P. 33–39. https://doi.org/10.1016/j.bmcl.2013.10.003
  38. Jackson P., Widen J., Harki D., Brummond K. // J. Med. Chem. 2016. V. 60. P. 839–885. https://doi.org/10.1021/acs.jmedchem.6b00788
  39. Strelow J. // SLAS Discov. 2017. V. 22. P. 3–20. https://doi.org/10.1177/1087057116671509
  40. Kuzmič P. // bioRxiv. 2020. P. 171207. https://doi.org/10.1101/2020.06.25.171207
  41. Soria J.-C., Ohe Y., Vansteenkiste J., Reungwetwattana T., Chewaskulyong B., Lee K.-H., Dechaphunkul A., Imamura F., Nogami N., Kurata T., Okamoto I., Zhou C., Cho B., Cheng Y., Cho E.K., Voon P.J., Planchard D., Su W.-C., Gray J., Lee S.-M., Hodge R., Marotti M., Rukazenkov Y., Ramalingam S. // N. Engl. J. Med. 2018. V. 378. P. 113–125. https://doi.org/10.1056/nejmoa1713137
  42. Xiao Q., Qu R., Gao D., Yan Q., Tong L., Zhang W., Ding J., Xie H., Li Y. // Bioorg. Med. Chem. 2016. V. 24. Р. 2673–2680. https://doi.org/10.1016/j.bmc.2016.04.032
  43. Zhou F., Zhang L., Jin Y., Liu W., Cheng P., He X., Xie J., Shen S., Lei J., Ji H., Hu Y., Liu Y., Cui Y., Lv Q., Lan J. // Bioorg. Med. Chem. Lett. 2017. V. 28. P. 1257–1261. https://doi.org/10.1016/j.bmcl.2017.12.009
  44. Yi Y., Wang L., Zhao D., Huang S., Wang C., Liu Z., Sun H., Liu K., Ma X., Li Y. // Chem. Biol. Drug. Des. 2018. V. 92. P. 1988–1997. https://doi.org/10.1111/cbdd.13370
  45. Shao J., Liu S., Liu X., Pan Y., Chen W. // Bioorg. Med. Chem. 2020. V. 28. P. 115680. https://doi.org/10.1016/j.bmc.2020.115680
  46. Fawwaz M., Mishiro K., Nishii R., Sawazaki I., Shiba K., Kinuya S., Ogawa K. // Molecules. 2020. V. 25. P. 2914. https://doi.org/10.3390/molecules25122914
  47. Chen L., Fu W., Feng C., Qu R., Tong L., Zheng L., Fang B., Qiu Y., Hu J., Cai Y., Feng J., Xie H., Ding J., Liu Z., Liang G. // Eur. J. Med. Chem. 2017. V. 140. P. 510–527. https://doi.org/10.1016/j.ejmech.2017.08.061
  48. Gao H., Yang Z., Yang X., Rao Y. // Bioorg. Med. Chem. 2017. V. 25. P. 4553–4559. https://doi.org/10.1016/j.bmc.2017.06.004
  49. Liu Q., Luo Y., Li Z., Chen C., Fang L. // Bioorg. Med. Chem. 2021. V. 36. P. 116094. https://doi.org/10.1016/j.bmc.2021.116094
  50. Yu H., Wei M., Cui Y., Sun X., Tong Z., Sun G., Tan S., Ma J., Gao P., Liao J., Liu Z., Wang S., Xiu W. // Patent Application WO2016054987A1, published 14.04.2016.
  51. Yang C.-H., Camidge D.N., Yang C.-T., Zhou J., Guo R., Chiu C.-H., Chang G.-C., Shiah H.-S., Chen Y., Wang C.-C., Berz D., Su W.-C., Yang N., Wang Z., Fang J., Chen J., Nikolinakos P., Lu Y., Pan H., Maniam A., Bazhenova L., Shirai K., Jahanzeb M., Willis M., Masood N., Chowhan N., Hsia T.-C., Jian H., Lu S. // J. Thorac. Oncol. 2020. V. 15. P. 1907–1918. https://doi.org/10.1016/j.jtho.2020.09.001
  52. Lu S., Wang Q., Zhang G., Dong X., Yang C.-T., Song Y., Chang G.-C., Lu Y., Pan H., Chiu C.-H., Wang Z., Feng J., Zhou J., Xu X., Guo R., Chen J., Yang H., Chen Y., Yu Z., Shiah H.-S., Wang C.-C., Yang N., Fang J., Wang P., Wang K., Hu Y., He J., Wang Z., Shi J., Chen S., Wu Q., Sun C., Li C., Wei H., Cheng Y., Su W.-C., Hsia T.-C., Cui J., Sun Y., Ou S.-H., Zhu V., Yang J. // J. Thorac. Oncol. 2022. V. 17. P. 411–422. https://doi.org/10.1016/j.jtho.2021.10.024
  53. Jiang Y. // Patent CN105085489A, published 25.11.2015.
  54. Blair H. // Drugs. 2023. V. 83. P. 1433–1437. https://doi.org/10.1007/s40265-023-01946-w
  55. Peng J., Costanzo M., Greco M., Green M., Wilde V., Zhang D. // Patent Application WO2016094821A2, published 16.06.2016.
  56. Shi Y., Zhao Y., Yang S., Zhou J., Zhang L., Chen G., Fang J., Zhu B., Li X., Shu Y., Shi J., Zheng R., Wang D., Yu H., Huang J., Zhuang Z., Wu G., Zhang L., Guo Z., Greco M., Li X., Zhang Y. // J. Thorac. Oncol. 2022. V. 17. P. 708–717. https://doi.org/10.1016/j.jtho.2022.01.015
  57. Yang S., Wu S., Zhao Y., Chen G., Zhu B., Li X., Wang K., Shi J., Cang S., Yao W., Fan Y., Fang J., Zhang L., Zhou J., Wu L., Zheng R., Huang M., Pan Y., Yang Z., Sun M., Yu H., Wang D., Huang J., Wang L., Shu Y., Chen Z., Liu C., Li J., Liu J., Sun S., Guo Y., Meng Z., Liu Z., Han Z., Wu G., Lu H., Ma R., Hu S., Zhao G., Zhang L., Liu Z., Xie C., Zhong D., Zhao H., Bi M., Yi S., Guo S., Yi T., Li W., Lin Y., Chen Z., Zhuang Z., Guo Z., Greco M., Wang T., Zhou A., Shi Y. // Lung Cancer. 2023. V. 180. P. 107194. https://doi.org/10.1016/j.lungcan.2023.107194
  58. Talele T. // J. Med. Chem. 2016. V. 59. P. 8712–8756. https://doi.org/10.1021/acs.jmedchem.6b00472
  59. Li J., An B., Song X., Zhang Q., Chen C., Wei S., Fan R., Li X., Zou Y. // Eur. J. Med. Chem. 2020. V. 212. P. 113019. https://doi.org/10.1016/j.ejmech.2020.113019
  60. An B., Pan T., Hu J., Pang Y., Huang L., Chan A., Li X., Yan J. // Eur. J. Med. Chem. 2019. V. 183. P. 111709. https://doi.org/10.1016/j.ejmech.2019.111709
  61. Gant T. // J. Med. Chem. 2013. V. 57. P. 3595–3611. https://doi.org/10.1021/jm4007998
  62. Di Martino R., Maxwell B. Pirali T. // Nat. Rev. Drug Discov. 2023. V. 22. P. 562–584. https://doi.org/10.1038/s41573-023-00703-8
  63. Meng Y., Yu B., Huang H., Peng Y., Li E., Yao Y., Song C., Yu W., Zhu K., Wang K., Yi D., Du J., Chang J. // J. Med. Chem. 2021. V. 64. P. 925–937. https://doi.org/10.1021/acs.jmedchem.0c02005
  64. Zhou P., Chen G., Gao M., Wu J. // Bioorg. Med. Chem. 2018. V. 26. P. 6135–6145. https://doi.org/10.1016/j.bmc.2018.10.018
  65. Zhang H., Wu W., Feng C., Liu Z., Bai E., Wang X., Lei M., Cheng H., Feng H., Shi J., Wang J., Zhang Z., Jin T., Chen S., Hu S., Zhu Y. // Eur. J. Med. Chem. 2017. V. 135. P. 12–23. https://doi.org/10.1016/j.ejmech.2017.04.036
  66. Bouffard E., Zaro B., Dix M., Cravatt B., Wong C.-H. // Tetrahedron Lett. 2021. V. 74. P. 153178. https://doi.org/10.1016/j.tetlet.2021.153178
  67. Wang Y., Zhang X., Zhao L., Wang X., Han L., Dai X. // Patent Application WO2017088746A1, published 01.06.2017.
  68. Han L., Zhang X., Wang Z., Zhang X., Zhao L., Fu W., Liang X., Zhang Z., Wang Y. // Front. Pharmacol. 2021. V. 12. P. 665253. https://doi.org/10.3389/fphar.2021.665253
  69. Yan Q., Chen Y., Tang B., Xiao Q., Qu R., Tong L., Liu J, Ding J., Chen Y., Ding N., Tan W., Xie H., Li Y. // Eur. J. Med. Chem. 2018. V. 152. P. 298–306. https://doi.org/10.1016/j.ejmech.2018.04.052
  70. Zhang T., Qu R., Chan S., Lai M., Tong L., Feng F., Chen H., Song T., Song P., Bai G., Liu Y., Wang Y., Li Y., Su Y., Shen Y., Sun Y., Chen Y., Geng M., Ding K., Ding J., Xie H. // Mol. Cancer. 2020. V. 19. P. 90. https://doi.org/10.1186/s12943-020-01202-9
  71. Shi Y., Li B., Wu L., Pan Y., Pan Z., Liu Y., Fan Y., Ji Y., Fang J., Shi Q., Shi J., Gao H., Hu Y., Wang X., He Z., Ma R., Zhang Y., Jiang D., Bai Y., Zhang Y., Huang L., Zhou T., Liu H., Wang D., Wen Q., Chen G., Zang A., Wang X., Zhang X., Hu J., Yang R., Zhang G., Gu K., Wang L., Wang Q., Wei Z., Li Z., Lu H., Zhang H., Chen H., Song T. // J. Thorac. Oncol. 2022. V. 17. P. 1205–1215. https://doi.org/10.1016/j.jtho.2022.05.011
  72. Yang Z., Yang H., Ai Y., Zhang L., Li Z., Wan S., Xu X., Zhang H., Wu S., Zhang J., Zhang T. // Eur. J. Pharm. Sci. 2020. V. 152. P. 105463. https://doi.org/10.1016/j.ejps.2020.105463
  73. Rho J.K., Lee I.Y., Choi Y.J., Choi C.-M., Hur J.-Y., Koh J.S., Lee J., Suh B.-C., Song H.-J., Salgaonkar P., Lee J., Lee J., Jung D.S., Kim S.-Y., Woo D.-C., Baek I.-J., Lee J.-Y., Ha C.H., Sung Y.H., Kim J.K., Kim W.S., Song J.S., Kim C.H., Bivona T., Lee J.C. // Cancer Res. 2017. V. 77. P. 1200–1211. https://doi.org/10.1158/0008-5472.can-16-2432
  74. Yun J., Hong M.H., Kim S.-Y., Park S.-W., Kim S., Yun M.R., Kang H.N., Pyo K.H., Lee S.S., Koh J.S., Song H.-J., Kim D.K., Lee Y.S., Oh S.-W., Choi S., Kim H.R., Cho B.C. // Clin. Cancer Res. 2019. V. 25. Р. 2575–2587. https://doi.org/10.1158/1078-0432.ccr-18-2906
  75. Dhillon S. // Drugs. 2021. V. 81. P. 1107–1113. https://doi.org/10.1007/s40265-021-01533-x
  76. Yang H., Yan R., Jiang Y., Yang Z., Zhang X., Zhou M., Wu X., Zhang T., Zhang J. // Eur. J. Med. Chem. 2020. V. 187. P. 111966. https://doi.org/10.1016/j.ejmech.2019.111966
  77. Günther M., Lategahn J., Juchum M., Döring E., Keul M., Engel J., Tumbrink H., Rauh D., Laufer S. // J. Med. Chem. 2017. V. 60. P. 5613–5637. https://doi.org/10.1021/acs.jmedchem.7b00316
  78. Yang T., Zhang W., Cao S., Sun S., Cai X., Xu L., Li P., Zheng Z., Li S. // Eur. J. Med. Chem. 2022. V. 228. P. 113984. https://doi.org/10.1016/j.ejmech.2021.113984
  79. Luo H., Zhou H., Wang S., Wu Y. // Patent US10072002B2, published 11.09.2018.
  80. Deeks E. // Drugs. 2021. V. 81. P. 1775–1780. https://doi.org/10.1007/s40265-021-01588-w
  81. Shi Y., Zhang S., Hu X., Feng J., Ma Z., Zhou J., Yang N., Wu L., Liao W., Zhong D., Han X., Wang Z., Zhang X., Qin S., Ying K., Feng J., Fang J., Liu L., Jiang Y. // J. Thorac. Oncol. 2020. V. 15. P. 1015–1026. https://doi.org/10.1016/j.jtho.2020.01.010
  82. Li Y., Chang Y., Fu J., Ding R., Zhang L., Liang T., Liu Y., Liu Y, Hu J. // Eur. J. Med. Chem. 2021. V. 226. P. 113845. https://doi.org/10.1016/j.ejmech.2021.113845
  83. Zhao B., Xiao Z., Qi J., Luo R., Lan Z., Zhang Y., Hu X., Tang Q., Zheng P., Xu S., Zhu W. // Eur. J. Med. Chem. 2018. V. 163. P. 367–380. https://doi.org/10.1016/j.ejmech.2018.11.069
  84. Abbas A., Xing B., Loh T. // Angew. Chem. Int. Ed. 2014. V. 53. P. 7491–7494. https://doi.org/10.1002/anie.201403121
  85. Chen D., Guo D., Yan Z., Zhao Y. // Med. Chem. Comm. 2017. V. 9. P. 244–253. https://doi.org/10.1039/C7MD00571G
  86. Zhao Z., Bourne P. // Pharmaceuticals. 2022. V. 15. P. 1322. https://doi.org/10.3390/ph15111322
  87. Chen Y., Wu J., Wang A., Qi Z., Jiang T., Chen C., Zou F., Hu C., Wang W., Wu H., Hu Z., Wang W., Wang B., Wang L., Ren T., Zhang S., Liu Q., Liu J. // Eur. J. Med. Chem. 2017. V. 139. P. 674–697. https://doi.org/10.1016/j.ejmech.2017.08.035
  88. Jang J., Son J.B., To C., Bahcall M., Kim S.Y., Kang S.Y., Mushajiang M., Lee Y., Jänne P., Choi H.G., Gray N. // Eur. J. Med. Chem. 2017. V. 136. P. 497–510. https://doi.org/10.1016/j.ejmech.2017.04.079
  89. Fan Y., Li W., Nie W., Yao H., Ren Y., Wang M., Nie H., Gu C., Liu J., An B. // Molecules. 2023. V. 28. P. 2006. https://doi.org/10.3390/molecules28052006
  90. Li Z., Zou H., Zhu W., Shen C., Wang R., Liu W., Chen X., Tsui H., Yang Z., Zhang X. // Patent Application WO2019149164A1, published 08.08.2019.
  91. Dhillon S. // Drugs. 2023. V. 83. P. 1629–1634. https://doi.org/10.1007/s40265-023-01959-5
  92. Cheng H., Nair S., Murray B., Almaden C., Bailey S., Baxi S., Behenna D., Cho-Schultz S., Dalvie D., Dinh D., Edwards M., Feng J.L., Ferre R., Gajiwala K., Hemkens M., Jackson-Fisher A., Jalaie M., Johnson T., Kania R., Kephart S., Lafontaine J., Lunney B., Liu K., Liu Z., Matthews J., Nagata A., Niessen S., Ornelas M., Orr S., Pairish M., Planken S., Ren S., Richter D., Ryan K., Sach N., Shen H., Smeal T., Solowiej J., Sutton S., Tran K., Tseng E., Vernier W., Walls M., Wang S., Weinrich S., Xin S., Xu H., Yin M.-J., Zientek M., Zhou R., Kath J. // J. Med. Chem. 2016. V. 59. P. 2005–2024. https://doi.org/10.1021/acs.jmedchem.5b01633
  93. Xu X., Wang X., Mao L., Zhao L., Xi B. // Patent US9586965B2, published 07.03.2017.
  94. Xu X., Mao L., Xu W., Tang W., Zhang X., Xi B., Xu R., Fang X., Liu J., Fang C., Zhao L., Wang X., Jiang J., Hu P., Zhao H., Zhang L. // Mol. Cancer Ther. 2016. V. 15. P. 2586–2597. https://doi.org/10.1158/1535-7163.mct-16-0281
  95. Xia Z., Huang R., Zhou X., Chai Y., Chen H., Ma L., Yu Q., Li Y., Li W., He Y. // Eur. J. Med. Chem. 2021. V. 224. P. 113711. https://doi.org/10.1016/j.ejmech.2021.113711
  96. Tomassi S., Lategahn J., Engel J., Keul M., Tumbrink H., Ketzer J., Mühlenberg T., Baumann M., Schultz-Fademrecht C., Bauer S., Rauh D. // J. Med. Chem. 2017. V. 60. P. 2361–2372. https://doi.org/10.1021/acs.jmedchem.6b01626
  97. Lategahn J., Keul M., Klövekorn P., Tumbrink H., Niggenaber J., Müller M., Hodson L., Flaßhoff M., Hardick J., Grabe T., Engel J., Schultz-Fademrecht C., Baumann M., Ketzer J., Mühlenberg T., Hiller W., Günther G., Unger A., Müller H., Heimsoeth A., Golz C., Blank-Landeshammer B., Kollipara L., Zahedi R., Strohmann C., Hengstler J., Otterlo W., Bauer S., Rauh D. // Chem. Sci. 2019. V. 10. P. 10789– 10801. https://doi.org/10.1039/C9SC03445E
  98. Thress K., Paweletz C., Felip E., Cho B., Stetson D., Dougherty B., Lai Z., Markovets A., Vivancos A., Kuang Y., Ercan D., Matthews S., Cantarini M., Barrett J., Jänne P., Oxnard G. // Nat. Med. 2015. V. 21. P. 560–562. https://doi.org/10.1038/nm.3854
  99. Lategahn J., Tumbrink H., Schultz-Fademrecht C., Heimsoeth A., Werr L., Niggenaber J., Keul M., Parmaksiz F., Baumann M., Menninger S., Zent E., Landel I., Weisner J., Jeyakumar K., Heyden L., Russ N., Müller F., Lorenz C., Brägelmann J., Spille I., Grabe T., Müller M., Heuckmann J., Klebl B., Nussbaumer P., Sos M., Rauh D. // J. Med. Chem. 2022. V. 65. P. 6643–6655. https://doi.org/10.1021/acs.jmedchem.1c02080
  100. Günther M., Laux J., Laufer S. // Eur. J. Pharm. Sci. 2018. V. 128. P. 91–96. https://doi.org/10.1016/j.ejps.2018.11.021
  101. Planken S., Behenna D., Nair S., Johnson T., Nagata A., Almaden C., Bailey S., Ballard E., Bernier L., Cheng H., Cho-Schultz S., Dalvie D., Deal J., Dinh D., Edwards M., Ferre R., Gajiwala K., Hemkens M., Kania R., Kath J., Matthews J., Murray B., Niessen S., Orr S., Pairish M., Sach N., Shen H., Shi M., Solowiej J., Tran K., Tseng E., Vicini P., Wang Y., Weinrich S., Zhou R., Zientek M., Liu L., Luo Y., Xin S., Zhang C., Lafontaine J. // J. Med. Chem. 2017. V. 60. P. 3002−3019. https://doi.org/10.1021/acs.jmedchem.6b01894
  102. Hu J., Han Y., Wang J., Liu Y., Zhao Y., Liu Y., Gong P. // Bioorg. Med. Chem. 2018. V. 26. P. 1810–1822. https://doi.org/10.1016/j.bmc.2018.02.029
  103. Hu C., Wang A., Wu H., Qi Z., Li X., Yan X., Chen C., Yu K., Zou F., Wang W., Wang W., Wu J., Liu J., Wang B., Wang L., Ren T., Zhang S., Yun C., Liu J., Liu Q. // Oncotarget. 2017. V. 8. P. 18359–18372. https://doi.org/10.18632%2Foncotarget.15443
  104. Wang A., Li X., Wu H., Zou F., Yan X.-E., Chen C., Hu C., Yu K., Wang W., Zhao P., Wu J., Qi Z., Wang W., Wang B., Wang L., Ren T., Zhang S., Yun C.-H., Liu J., Liu Q. // J. Med. Chem. 2017. V. 60. P. 2944– 2962. https://doi.org/10.1021/acs.jmedchem.6b01907
  105. Cha M.-Y., Kang S.-J., Kim M.-R., Lee J.-Y., Jeon J.-Y., Jo M.-G., Kwak E.-J., Lee K.-O., Ha T.-H., Suh K.-H., Kim M.-S. // Patent Application US20130116213A1, published 09.05.2013.
  106. Kim E. // Drugs. 2016. V. 76. P. 1153–1157. https://doi.org/10.1007/s40265-016-0606-z
  107. Park K., Jӓnne P., Kim D.-W., Han J.-Y., Wu M.-F., Lee J.-S., Kang J.-H., Lee D.H., Cho B.C., Yu C.-J., Pang Y.K., Felip E., Kim H., Baek E., Noh Y.S. // Cancer. 2021. V. 127. P. 1407–1416. https://doi.org/10.1002/cncr.33385
  108. Xiao Z., Zhou Z., Chu C., Zhang Q., Zhou L., Yang Z., Li X., Yu L., Zheng P., Xu S., Zhu W. // Eur. J. Med. Chem. 2020. V. 203. P. 112511. https://doi.org/10.1016/j.ejmech.2020.112511
  109. Xiao Z., Chu C., Zhou L., Zhou Z., Zhang Q., Yang F., Yang Z., Zheng P., Xu S., Zhu W. // Bioorg. Med. Chem. 2020. V. 28. P. 115669. https://doi.org/10.1016/j.bmc.2020.115669
  110. Zhao B., Zhao C., Hu X., Xu S., Lan Z., Guo Y., Yang Z., Zhu W., Zheng P. // Eur. J. Med. Chem. 2019. V. 185. P. 111809. https://doi.org/10.1016/j.ejmech.2019.111809
  111. Coumar M.S., Chu C.Y., Lin C.W., Shiao H.Y., Ho Y.L., Reddy R., Lin W.H., Chen C.H., Peng Y.H., Leou J.S., Lien T.W., Huang C.T., Fang M.Y., Wu S.H., Wu J.S., Chittimalla S.K., Song J.S., Hsu J.T., Wu S.Y., Liao C.C., Chao Y.S., Hsieh H.P. // J. Med. Chem. 2010. V. 53. P. 4980–4988. https://doi.org/10.1021/jm1000198
  112. Peng Y.-H., Shiao H.-Y., Tu C.-H., Liu P.-M., Hsu J., Amancha P.K., Wu J.-S., Coumar M.S., Chen C.-H., Wang S.-Y., Lin W.-H., Sun H.-Y., Chao Y.-S., Lyu P.-C., Hsieh H.-P., Wu S.-Y. // J. Med. Chem. 2013. V. 56. Р. 3889–3903. https://doi.org/10.1021/jm400072p
  113. Lin S.-Y., Hsu Y.C., Peng Y.-H., Ke Y.-Y., Lin W.-H., Sun H.-Y., Shiao H.-Y., Kuo F.-M., Chen P.-Y., Lien T.-W., Chen C.-H., Chu C.-Y., Wang S.-Y., Yeh K.-C., Chen C.-P., Hsu T.-A., Wu S.-Y., Yeh T.-K., Chen C.-T., Hsieh H.-P. // J. Med. Chem. 2019. V. 62. P. 10108− 10123. https://doi.org/10.1021/acs.jmedchem.9b00722
  114. Li M.-C., Coumar M., Lin S.-Y., Lin Y.-S., Huang G.-L., Chen C.-H., Lien T.-W., Wu Y.-W., Chen Y.-T., Chen C.-P., Huang Y.-C., Yeh K.-C., Yang C.-M., Kalita B., Pan S.-L., Hsu T.-A., Yeh T.-K., Chen C.-T., Hsieh H.-P. // J. Med. Chem. 2023. V. 66. P. 2566−2588. https://doi.org/10.1021/acs.jmedchem.2c01434
  115. Das D., Xie L., Wang J., Xu X., Zhang Z., Shi J., Le X., Hong J. // Bioorg. Med. Chem. Lett. 2018. V. 29. P. 591–596. https://doi.org/10.1016/j.bmcl.2018.12.056
  116. Das D., Hong, J. // Eur. J. Med. Chem. 2019. V. 170. P. 55–72. https://doi.org/10.1016/j.ejmech.2019.03.004
  117. Das D., Xie L., Wang J., Shi J., Hong J. // Bioorg. Chem. 2020. V. 99. P. 103790. https://doi.org/10.1016/j.bioorg.2020.103790
  118. Liu Z., Wang L., Feng M., Yi Y., Zhang W., Liu W., Li L., Liu Z., Li Y., Ma X. // Bioorg. Chem. 2018. V. 77. P. 593–599. https://doi.org/10.1016/j.bioorg.2018.01.035
  119. Xu T., Peng T., Ren X., Zhang L., Yu L., Luo J., Zhang Z., Tu Z., Tong L., Huang Z., Lu X., Geng M., Xie H., Ding J., Ding K. // MedChemComm. 2015. V. 6. P. 1693–1697. https://doi.org/10.1039/C5MD00208G
  120. Yu L., Huang M., Xu T., Tong L., Yan X., Zhang Z., Xu Y., Yun C., Xie H., Ding K., Lu X. // Eur. J. Med. Chem. 2017. V. 126. P. 1107–1117. https://doi.org/10.1016/j.ejmech.2016.12.006
  121. Zhang Z., Zou J., Yu L., Luo J., Li Y., Tu Z., Ren X., Wei H., Song L., Lu X., Ding K. // Cancer Med. 2018. V. 7. P. 1430–1439. https://doi.org/10.1002/cam4.1392
  122. Hao Y., Lyu J., Qu R., Tong Y., Sun D., Feng F., Tong L., Yang T., Zhao Z., Zhu L., Ding J., Xu Y., Xie H., Li H. // J. Med. Chem. 2018. V. 61. P. 5609–5622. https://doi.org/10.1021/acs.jmedchem.8b00346
  123. Hao Y., Wang X., Zhang T., Sun D., Tong Y., Xu Y., Chen H., Tong L., Zhu L., Zhao Z., Chen Z., Ding J., Xie H., Xu Y., Li H. // J. Med. Chem. 2016. V. 59. P. 7111–7124. https://doi.org/10.1021/acs.jmedchem.6b00403
  124. Hao Y., Lyu J., Qu R., Sun D., Zhao Z., Chen Z., Ding J., Xie H., Xu Y. Li H. // Sci. Rep. 2017. V. 7. P. 3830. https://doi.org/10.1038/s41598-017-04184-9
  125. Wurz R., Pettus L., Ashton K., Brown J., Chen J.J., Herberich B., Hong F.-T, Hu-Harrington E., Nguyen T., St. Jean, D., Jr., Tadesse S., Bauer D., Kubryk M., Zhan J., Cooke K., Mitchell P., Andrews K., Hsieh F., Hickman D., Kalyanaraman N., Wu T., Reid D., Lobenhofer E., Andrews D., Everds N., Guzman R., Parsons A., Hedley S., Tedrow J., Thiel O., Potter M., Radinsky R., Beltran P., Tasker A. // ACS Med. Chem. Lett. 2015. V. 6. P. 987–992. https://doi.org/10.1021/acsmedchemlett.5b00193
  126. Pawara R., Ahmad I., Nayak D., Wagh S., Wadkar A., Ansari A., Belamkar S., Surana S., Kundu C., Patil C., Patel H. // Bioorg. Chem. 2021. V. 115. P. 105234. https://doi.org/10.1016/j.bioorg.2021.105234
  127. Amaral D., Lategahn J., Fokoue H., Silva E., Sant’Anna C., Rauh D., Barreiro E., Laufer S., Lima L. // Sci. Rep. 2019. V. 9. P. 14. https://doi.org/10.1038/s41598-018-36846-7
  128. Zhang H., Wang J., Zhao H.-Y., Yang X.-Y., Lei H., Xin M., Cao Y.-X., Zhang S.-Q. // Bioorg. Med. Chem. 2018. V. 26. P. 3619–3633. https://doi.org/10.1016/j.bmc.2018.05.039

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2. Fig. 1. (a) – First-generation EGFR inhibitors; (b) – structure of the ATP-binding site of EGFR [9]; (c) – mode of binding of erlotinib to EGFR [9].

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3. Fig. 2. Second-generation EGFR inhibitors.

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4. Fig. 3. (a) – First third-generation EGFR inhibitors; (b) – mode of WZ4002 binding to EGFR; (c) – superposition of WZ4002 and rociletinib superpositions in EGFR T790M [30].

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5. Fig. 4. Limertinib and pyridine analogs of osimertinib.

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6. Fig. 5. Pyrazole- and triazole-containing analogs of osimertinib.

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7. Fig. 6. Dual-action inhibitors of EGFR DM/ALK and EGFR DM/BTK.

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8. Fig. 7. Pyrrole-, pyrazole-pyrimidine and purine EGFR DM inhibitors.

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9. Fig. 8. Thiopheno- and thiopyranopyrimidine EGFR inhibitors DM.

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10. Fig. 9. EGFR DM inhibitors with quinazoline and modified quinazoline scaffolds.

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11. Scheme 1. Osimertinib precursors and its major metabolites.

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12. Scheme 2. 5-Methylthio analogues of WZ4002.

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13. Scheme 3. Analogues of WZ4002 with urea as a linker insert.

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14. Scheme 4. Rociletinib analogues.

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15. Scheme 5. Rociletinib analogues.

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16. Scheme 6. 2,4-Diaminopyrimidine analogs of osimertinib.

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17. Scheme 7. N-Oxide and fluorinated analogs of osimertinib.

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18. Scheme 8. Osimertinib analogues.

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19. Scheme 9. Cyclopropyl analogs of osimertinib.

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20. Scheme 10. Dosimertinib and its precursors.

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21. Scheme 11. Osimertinib analogues.

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22. Scheme 12. Osimertinib analogues.

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23. Scheme 13. Pyrazole- and triazole-containing 2,4-diaminopyrimidines.

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24. Scheme 14. Modifications of the “head” and amine parts of osimertinib.

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25. Scheme 15. Osimertinib analogs with a pyridine linker.

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26. Scheme 16. Tetrahydrothienopyridine analogs of osimertinib.

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27. Scheme 17. Modifications of acrylamide and pyrimidine backbone.

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28. Scheme 18. Allenamide analogs of osimertinib.

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29. Scheme 19. Furanopyrimidine EGFR inhibitors DM.

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