REVIEW

Emerging Applications of Precise Chemistry in Drug Discovery

  • Rong Liu ,
  • Yinglin Zuo ,
  • Yingjun Zhang ,
  • Ji Zhang
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  • aSunshine Lake Pharma Co.,Ltd, Dongguan 523871
    bState Key Laboratory of Anti-Infective Drug Development, Sunshine Lake Pharma Co.,Ltd, Dongguan 523871
    cEnterprise Key Laboratory of Anti-viral Drug Development for Guangdong Province, Dongguan 523871

Received date: 2025-05-30

  Revised date: 2025-08-06

  Online published: 2025-09-12

Supported by

State Key Laboratory of Anti-Infective Drug Development (NO.2015DQ780357) and Enterprise Key Laboratory of Anti-viral Drug Development for Guangdong Province (Grant No.2020B1212070003) and Enterprise Key Laboratory of Anti-viral Drug Development for Guangdong Province (Grant No.2023B1212070004).

Abstract

To enhance the efficiency of drug research and synthesis, the implementation of "Precision Chemistry" characterized by molecular-level precise design and control of drug molecules to achieve highly efficient, selective, and predictable chemical reactions has become imperative. While "Precision Chemistry" aligns with existing goals of "Green Chemistry" such as atom economy and waste minimization, its core emphasis lies in precision and efficiency. These two concepts intersect rather than being subordinate to each other. This review demonstrates the philosophy of "Precision Chemistry" through practical examples of drug discovery and synthesis of anti-cancer drugs, anti-infection drugs, targeted protein degradation drugs、cardiovascular/metabolic drugs, anti-inflammatory drugs, aiming to better understanding the "Precision Chemistry" concept to serve pharmaceutical research and process well.

Cite this article

Rong Liu , Yinglin Zuo , Yingjun Zhang , Ji Zhang . Emerging Applications of Precise Chemistry in Drug Discovery[J]. Chinese Journal of Organic Chemistry, 0 : 202505031 . DOI: 10.6023/cjoc202505031

References

[1] (a) Bartfai, T.; Lees, G. V. Drug discovery: from bedside to Wall Street 1st Ed, Elsvier Science, London Wall, 2006, pp. 3~12.
(b) Blass, B. E. Basic Principles of Drug Discovery and Development 2nd Ed, Elsvier Science, 2021, pp. 1~44.
(c) Brown D. G.; Wobst H. J.; J. Med. Chem.2021, 64, 2312.
[2] (a) Ji S.-F.; Jun C.; Chen Y.-J.; Wang, D. S. Precis. Chem.2023, 1, 199.
(b) Gao, F.; Li, J.; Ahmad, T.; Luo, Y.-C.; Zhang, Z.-F.; Yuan, Q.-J.; Huo, X.-H.; Song, T.; Zhang, W. B.Sci. China Chem. 2022, 65, 1968.
(c) Li J.; Gao F.; Ahmad T.; Luo Y.-C.; Zhang Z.-F.; Yuan Q.-J.; Zhang, W. B. Chin. J. Chem.2023, 41, 1319.
(d) Lehn, J. M. Angew. Chem. Int. Ed.1988, 27, 89.
(e) Yao, J. N. Bulletin of Chinese Academy of Sciences,2011, 26, 11 (in Chinese).
(姚建年, 中国科学院院刊, 2011, 26, 11.)
(f) Stoddart, J. F. Angew. Chem. Int. Ed.2017, 56, 11094.
(g) Sharpless K. B.; Finn M. G.; Kolb, H. C. Angew. Chem. Int. Ed.2025, 64, e202501229.
[3] (a) Zhang J.; Nie B.; Zhang, Y. J. Chin. J. Org. Chem.2015, 35, 337 (in Chinese).
(张霁, 聂飚, 张英俊, 有机化学, 2015, 35, 337.)
(b) Campos K. R.; Coleman P. J.; Alvarez J. C.; Dreher S.D.; Garbaccio R. M.; Terrett N. K.; Tillyer R. D.; Truppo M. D.; Parmee E. R. Science.2019, 363, 6424.
(c) Lasso J. D.; Castillo-Pazos D. J.; Li, C. J. Chem. Soc. Rev.2021, 50, 10955.
(d) Li E.-Q.; Lindsley C.W.; Chang J.-B.; Yu, B. J. Med. Chem.2024, 67, 13509.
[4] (a) Leach A. R.; Gillet V. J.; Lewis R. A.; Taylor, R. J. Med. Chem.2010, 53, 539.
(b) Zhang W.-L.; Pei J.-F.; Lai, L. H. J. Chem. Inf. Model.2017, 57, 403.
(c) Ren Q.-Y.; Nie B.; Zhang Y.-J.; Zhang, J. Chin. J. Org. Chem.2018, 38, 2465 (in Chinese).
(任青云, 聂飚, 张英俊, 张霁, 有机化学, 2018, 38, 2465.)
(d) Blakemore D. C.; Castro L.; Churcher I.; Rees D. C.; Thomas A. W.; Wilson D. M.; Wood A. Nat. Chem.2018, 10, 383.
(e) Li X.-Q.; Li X.-W.; Liu F.; Li S.; Shi, D. Y. J. Med. Chem.2021, 64, 10581.
(f) Nangia, A. K. Cryst. Growth Des.2024, 24, 6888.
[5] (a) Siegel R. L.; Kratzer T. B.; Giaquinto A. N.; Sung H.; Jemal, A. CA Cancer. J. Clin.2025, 75, 10.
(b) Han B.-F.; Zheng R.-S.; Zeng H.-M.; Wang S.-M.; Sun K.-X.; Chen R.; Li L.; Wei W. Q.; He. J. J. Natl. Cancer. Cent.2024, 4, 47.
[6] (a) Pommier, Y. Nat. Rev. Cancer.2006, 6, 789.
(b) Martino E.; Volpe S. D.; Terribile E.; Benetti E.; Sakaj M.; Centamore A.; Sala A.; Collina, S. Bioorg. Med. Chem. Lett.2017, 27, 701.
[7] Sawada S.; Okajima S.; Aiyama R.; Nokata K.; Furuta T.; Yokokura T.; Sugino E.; Yamaguchi K.; Miyasaka, T. Chem. Pharm. Bull.1991, 39, 1446.
[8] Sawada S.; Okajima S.; Aiyama R.; Nokata K.; Furuta T.; Yokokura T.; Sugino E.; Yamaguchi K.; Miyasaka, T. Chem. Pharm. Bull.1991, 39, 2574.
[9] Ahn S.-K.; Choi N.-S.; Jeong B.-S.; Kim K.-K.; Journ D.-J.; Kim J.-K.; Lee S.-J.; Kim J.-W.; Hong C.; Jew, S. S. J. Heterocyelic. Chem.2000, 37, 1141.
[10] (a) Wang X.-Z.; Zhuang Y.-M.; Wang Y.-K.; Jiang M.-K.; Yao, L. Eur. J. Med. Chem.2023, 260, 115710.
(b) Khaiwa N.; Maarouf N. R.; Darwish M. H.; Alhamad D. W.; Sebastian A.; Hamad M.; Omar H. A.; Orive G.; Altel, T. H. Eur. J. Med. Chem.2021, 223, 113639.
[11] (a) Wang Z.-J.; Li H.-X.; Gou L.-T.; Li W.; Wang, Y. X. Acta. Pharm. Sin. B.2023, 13, 4025.
(b) Govindan S.V.; Goldenberg D. M.; Moon. J. S. Camptothecin-binding moiety conjugates[P]. USA: US7591994B2,2008-02-06.
(c) Govindan S.V.; Goldenberg D. M. Combining radioimmunotherapy and antibody-drug conjugates for improved cancer therapy[P]. USA: US8435529B2,2010-12-01.
[12] (a) Xue T.-T.; Wang J.; Xiao L.; Song H.-M.; Liu D.-N.; Zhang Q.; Yuan X.-X.; Liu L.-P.; Yang Q.-Y.; Guo D.-T.; Wang L.-C.; Wang, J. Y. Antibody-drug conjugate and preparation method and application thereof[P]. PCT: WO2018036438A1,2017-08-18.
(b) Cai J-Q.; Song S.; Xue T.-T.; Xiao L.; Deng H.-W.; Tian Q.; Wang J.; Liu D.-N.; Yuan H.-M.; Yang Z.-N.; Cao X.; Zhong G.-Q.; Wang L.-C.; Wang, J. Y. Bioactive conjugate, preparation method therefor and use thereof[P]. PCT: WO2019114666A1,2018-12-10.
[13] Fu., Z.-W; Li S.-J.; Han S.-F.; Shi C.; Zhang, Y. Signal. Transduct. Target. Ther.2022, 7, 93.
[14] (a) Melchert M.; List, A. Int. J. Biochem. Cell. Biol.2007, 39, 1489.
(b) Saha D.; Kharbanda A.; Yan W.; Lakkaniga N. R.; Frett B.; Li, H. Y. J. Med. Chem.2020, 63, 441.
(c) McVicker R. U.; O'Boyle, N. M. J. Med. Chem.2024, 67, 2305.
[15] Bartlett J. B.; Dredge K.; Dalgleish, A. G. Nat. Rev. Cancer.2004, 4, 314.
[16] (a) Kroenke J.; Udeshi N. D.; Narla A.; Grauman P.; Hurst S. N.; McConkey M.; Svinkina T.; Heckl D.; Comer E.; Li X.-Y.; Ciarlo C.; Hartman E.; Munshi N.; Schenone M.; Schreiber S. L.; Carr S. A.; Ebert B. L. Science.2014, 343, 301.
(b) Lu G.; Middleton R. E.; Sun H.-H.; Naniong M.V.; Ott C. J.; Mitsiades C. S.; Wong K.-K.; Bradner J. E.; Kaelin-Jr W. G. Science.2014, 343, 305.
(c) Fischer E. S.; Boehm K.; Lydeard J. R.; Yang H.-D.; Stadler M. B.; Cavadini S.; Nagel J.; Serluca F.; Acker V.; Lingaraju G. M.; Tichkule R. B.; Schebesta M.; Forrester W. C.; Schirle M.; Hassiepen U.; Ottl J.; Hild M.; Beckwith R. E-J.; Harper J. W.; Jenkins J. L.; Thomas N. H. Nature.2014, 512, 49.
(d) Chamberlain P. P.; Lopez-Girona A.; Miller K.; Carmel G.; Pagarigan B.; Chie-Leon B.A.; Rychak E.; Corral L. G.; Ren Y.-J.; Wang M.; Riley M.; Delker S. L.; Ito T.; Ando H.; Mori T.; Hirano Y.; Handa H.; Hakoshima T.; Daniel T. O.; Cathers, B. E. Nat. Struct. Mol. Biol.2014, 21, 803.
(e) Sievers Q. L.; Petzold G.; Bunker R. D.; Renneville A.; Słabicki M.; Liddicoat B. J.; Abdulrahman W.; Mikkelsen T.; Ebert B. L.; Thomas N. H. Science.2018, 362, 6414.
(f) Maniaci C.; Ciulli, A. Curr. Opin. Chem. Biol.2019, 52, 145.
(g) Dong G.-Q.; Ding Y.; He S.-P.; Sheng, C. Q. J. Med. Chem.2021, 64, 10606.
[17] Mullard, A. Nat. Rev. Drug. Discov.2024, 23, 799.
[18] Salami J.; Crews C. M. Science.2017, 355, 1163.
[19] Sun X.-Y.; Gao H.-Y.; Yang Y.-Q.; He M.; Wu Y.; Song Y.-G.; Tong Y.; Rao, Y. Signal. Transduct. Target. Ther.2019, 4, 64.
[20] Bekes M.; Langley D. R.; Crews, C. M. Nat. Rev. Drug. Discov.2022, 21, 181.
[21] Schreiber, S. L. Cell.2021, 184, 3
[22] Costacurta M.; He J.; Thompson P. E.; Shortt, J. J. Pers. Med.2021, 11, 1185.
[23] Dragovich, P. S. Chem. Soc. Rev.2022, 51, 3886.
[24] Chuang S.-S.; Liao C.-B.; Sum W.-T.; Liang C.-H.; Lin W.-H.; Lai C.-L.; Lin H.-S.; Antibody PROTAC conjugates[P]. PCT: WO2019140003A1,2019-01-09.
[25] Poudel Y. B.; Thakore R. R.; Chekler, E. P. J. Med. Chem.2024, 67, 15996.
[26] Tong Y.-Z.; Xue T.-T.; Song S.; Xiao L.; Cai, J. Q. Antibody-drug conjugate containing MYC protein degradation agent bioactive compound, preparation method therefor, and use thereof[P]. PCT: WO2024027795A1,2023-08-03.
[27] Aguilera C. C.; Valero T.; Macias A. L.; Baillache D. J.; Croke S.; Broceta, A. U. J. Med. Chem.2022, 65, 1047.
[28] (a) Honigber L.; Verner E.; Pan, Z. Y. Inhibitors of bruton's tyrosine kinase[P]. PCT: WO2008039218A2,2006-12-28.
(b) Honigber L.; Verner E.; Buggy J.; Loury D.; Chen. W. Inhibitors of bruton's tyrosine kinase[P]. PCT: WO2008121742A2,2008-03-27.
(c) Honigber L.; Verner E.; Buggy J.; Loury D.; Chen. W. Inhibitors of bruton's tyrosine kinase for the treatment of solid tumors[P]. PCT: WO2010009342A2,2009-07-16.
[29] Bender A. T.; Gardberg A.; Pereira A.; Johnson T.; Wu Y.; Grenningloh R.; Head J.; Morandi F.; Haselmayer P.; Bujalski, L. L. Mol. Pharmacol.2017, 91, 208.
[30] Wen T.-Y.; Wang J.-S.; Shi Y.-K.; Qian H.-L.; Liu P. Leukemia.2021, 35, 312.
[31] (a) Beck P. A.; Cesario C.; Cox M.; Dong H.-Q.; Foreman K.; MulviHill M. J.; Nigro A. I.; Saroglou L.; Steining A. G.; Sun Y.-C.; Weng Q.-H.; Wener D.; Wikes R.; Williams, J. Imidazopyrazine tyrosine kinase inhibitors[P]. PCT: WO2005037836A2,2004-10-14.
(b) Barf T. A.; Jans C. M.; Man. D. A.; Oubrie A. A.; Raaijmakers H. C-A.; Rewinkel J. B-R.; Sterrenburg J. G.; Wijkmans J. C-M.; 4-Imidazopyridazin- 1 -yl-benzamides and 4 - imidazotriazin- 1 - yl - benzamides as BTK- inhibitors[P]. PCT: WO2013010868A1,2012-07-11.
(c) Izumi R.; Salva F.; Ahmed, H. BTK inhibitors for hematopoietic mobilization[P]. PCT: WO2015057992A1,2014-10-16.
(d) Ahmed H.; Rothbaum W.; Izumi R.; Lannutti B.; Covey T.; Ulrich R.; Johnson D.; Braf T.; Kaptein A. Methods of Treating Chronic Lymphocytic Leukemia and Small Lymphocytic Leukemia Using a BTK Inhibitor[P]. USA: US20170095471A1,2025-01-21.
(e) Izumi R.; Salva F.; Hamdy, A. Methods of blocking the CXCR-4/SDF-1 signaling pathway with inhibitors of bone marrow x kinase[P]. PCT: WO2015185998A2,2015-04-10.
(f) Izumi R.; Salva F.; Hamdy, A. Methods of blocking the CXCR/SDF-1 signaling pathway with inhibitors of bruton's tyrosine kinase[P]. PCT: WO2015181633A2,2015-04-10.
[32] Moraru R.; Argos B. V.; Minton A.; Buermann L.; Pan S.-Y.; Wales T. E.; Joseph R. E.; Andreotti A. H.; Strefford J. C.; Packham G.; Baud, M. G-J. J. Med. Chem.2024, 67, 13572.
[33] (a) Guo Y.-H.; Wang, Z. W. Fused heterocyclic compounds as protein kinase inhibitors[P]. PCT: WO2014173289A1,2014-04-22.
(b) Gourlay, S. Treatment of pemphigus[P]. PCT: WO2016100914A1, 2015-12-18.
(c) Weiss. M. S.; Miskin H. P.; Sportelli, P. Combination of anti-CD20 antibody, PI3 kinase-delta selective inhibitor, and BTK inhibitor to treat B-cell proliferative disorders[P]. PCT: WO2017205843A1,2017-05-26.
(d)Wang Z.-W.; Gup Y.-H.; Shi G. Y. Crystalline form of (S)-7-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetra-hydropyrazolo[1,5-a] pyrimidine-3-carboxamide preparation, and uses thereof[P]. PCT: WO2018033853A2,2017-08-15.
(e) Hu N.; Wang L.; Song J.; Zhang T.; Li K.; Luo L.-S.; Wei M.; Wang Z.-W.; Guo, Y. H. Use of a combination comprising a BTK inhibitor for treating cancers[P]. PCT: WO2018033135A1,2017-08-18.
[34] Caldwell R. D.; Qiu H.; Askew B. C.; Bender A. T.; Brugger N.; Camps M.; Dhanabal M.; Dutt V.; Eichhorn T.; Gardberg A. S.; Goutopoulos A.; Grenningloh R.; Head J.; Healey B.; Hodous B. L.; Huck B. R.; Johnson T. L.; Jones C.; Jones R. C.; Mochalkin I.; Morandi F.; Nguyen N.; Meyring M.; Potnick J. R.; Santos D. C.; Schmidt R.; Sherer B.; Shutes A.; Urbahns K.; Follis A. V.; Wegener A. A.; Zimmerli S. C.; Bujalski, L. L. J. Med. Chem.2019, 62, 7643.
[35] (a) Sun. Y.-H.; Zhao X.-W.; Ding N.; Gao H.-Y.; Wu Y.; Yang Y.-Q.; Zhao M.; Hwang J.; Song Y.-Q.; Liu W.-L.; Rao Y. Cell. Res.2018, 28, 779.
(b) Sun, Y.-H.; Ding, N.; Song, Y.-Q.; Yang, Z.-M.; Liu, W.-L.; Zhu, J.; Rao, Y.Leukemia. 2019, 33, 2105.
(c) Zhu C.; Yang Z.-M.; Zhang Y.-X.; Li Z.-J.; Li G.-C.; Yang B.; Kang N.; Wang J.-W.; Sun Y.-H.; Ding N.; Rao Y.; Liu, W. L. Cell. Discov.2024, 10, 82.
[36] (a) Alu A.; Lei H.; Han X.-J.; Wei. Y.-Q.; Wei. X. W. J. Hematol. Oncol.2022, 15, 138.
(b) Wang H.-X.; Lei B.-L.; Huo C.-X.; Sun D.-Q.; Chen J.; Wang Z.-W.; Wang, Y. C. Degradation of bruton's tyrosine kinase (BTK) by conjugation of BTK inhibitors with E3 ligase ligand and methods of use[P]. PCT: WO2021219070A1,2021-04-29.
(c) Robbins D. W.; Noviski M. A.; Tan Y.-S.; Konst Z. A.; Kelly A.; Auger P.; Brathaban N.; Cass R.; Chan M.-L.; Cherala G.; Clifton M. C.; Gajewski S.; Ingallinera T. G.; Karr D.; Kato D.; Ma J.; McKinnell J.; McIntosh J.; Mihalic J.; Murphy B.; Panga J. R.; Peng G.; Powers J.; Perez L.; Rountree R.; McClellan A. T.; Sands A. T.; Weiss D. R.; Wu J.; Ye J.; Guiducci C.; Hansen G.; Cohen, F. J. Med. Chem.2024, 67, 2321.
(d) Sands. A.; Kelly, A. Bifunctional compounds for degrading BTK via ubiquitin proteosome pathway[P]. PCT: WO2021113557A1,2020-12-03; Guiducci, C.; Noviski, M.; Powers, J.; Rounttree, R.; Tan, Y. S. Bifunctional compounds for degrading BTK with diminished imid activity[P]. PCT: WO2023287928A1, 2022-07-13.; Brown, R. J.; Sands, A. Piperidinylpyrazine-carboxamide compounds for treating and preventing cancer and for degrading BTK[P]. PCT: WO2023076303A1, 2022-10-25.
(e) Zhang C.; Liao Y.-T.; Wang J.-M.; Zhu G.-Z.; Ye F.; Tang P.-M.; Chen X.-G.; Huang Z.-G.; Wu S.-T.; Li Y.; Yan, P. K. BTK inhibitor ring derivative, preparation method therefor and pharmaceutical application thereof[P]. PCT: WO2020239103A1,2020-05-29; Zhang, C.; Liao, Y.-T.; Wang, J.-M.; Chen, X.-F.; Chen, X.-G.; Zou, S.-J.; Yuan, S.; Ye, F.; Tang, P.-M.; Zhu, G.-Z.; Huang, Z.-G.; Wu, S.-T.; Li, Y.; Ni, J.; Yan. P. Compound having BTK kinase degrading activity, and preparation method and pharmaceutical use therefor[P]. PCT: WO2022007824A1, 2021-07-07; Zhang, C.; Liao, Y.-T.; Wang, J.-M.; Huang, L.-B.; Zhu, G.-Z.; Li, Y.; Yan, P. K. Salt of compound for degrading BTK, crystal form thereof, and use thereof in medicine[P]. PCT: WO2022052950A1, 2021-09-08; Zhang, C.; Liao, Y.-T.; Xu, J.-X.; Lu, X.-L.; Li, S.-C.; Tang, P.-M.; Tang, D.-C.; Cheng, X.-F.; Li, Y.; Yan, P. K. Polycyclic fused-ring BTK degradation agent and use thereof in medicine[P]. PCT: WO2025026455A1, 2024-08-05.
(f) Zhou X.-L.; Li J.; Liu X.-G.; Zhou Y.-B.; Hu M.; Luo X.-M.; Xie J.-F.; Kan W.-J.; Su M.-B.; Wu, Y. Z. Bruton's tyrosine kinase and mutant degrader composition and application thereof[P]. PCT: WO2023274390A1,2022-06-30; Zhou, X.-L.; Li, J.; Liu, X.-G.; Zhou, Y.-B.; Hu, M.; Luo, X.-M.; Xie, J.-F.; Kan, W.-J.; Wu, Y.-Z.; Hu, X.-B.; Su, M. B. Multifunctional compound capable of degrading BTK kinase, and composition and use[P]. PCT: WO2023088477A1, 2022-11-22.
(g) Kim P.-H.; Cho S.-Y.; Ha J.-D.; Park C.-H.; Hwang J.-Y.; Kim H.-J.; Lee S.-H.; Lim Y.-S.; Kim H.-W.; Yoo S.-M.; Suh B.-S.; Park J.-Y.; Ryu J.-H.; Ahn J.-M.; Moon L.-J.; Lee, H. H. Novel bifunctional heterocyclic compound having BTK degradation function via ubiquitin proteasome pathway, and use thereof[P]. PCT: WO2022270994A1,2022-06-24; Lee, S.-H.; Ryu, J.-H.; Ahn, J.-M.; Moon, H.-J.; Lee, H.-H.; Jang, M.-Y.; Yun, W.-S.; Kim, Y.-E.; Yoo, S.-M.; Lim, Y.-S.; Jeong, N.-R.; Kim, S.-H.; Choi, A.-R.; Kim, H. W. Compound having BTK protein degradation activity, and medical uses thereof[P]. PCT: WO2023080732A1, 2022-11-04
[37] 《Global report on infection prevention and control: executive summary》, WHO, 2024, ISBN:9789240049741
[38] Goethe O.; Heuer A.; Ma X.-S.; Wang Z.-X.; Herzon, S. B. Nat. Prod. Rep.2019, 36, 220.
[39] Heidtmann C. V.; Voukia F.; Hansen L. N.; Sorensen S. H.; Urlund B.; Nielsen S.; Pedersen M.; Kelawi N.; Andersen B. N.; Pedersen M.; Reinholdt P.; Kongsted J.; Nielsen C. U.; Klitgaard J. K.; Nielsen, P. J. Med. Chem.2020, 63, 15693.
[40] (a) Zeng M.-S.; Murphy S. K.; Herzon, S. B. J. Am. Chem. Soc.2017, 139, 16377.
(b) Ma X.-S.; Kucera R.; Goethe O. F.; Murphy S. K.; Herzon, S. B. J. Org. Chem.2018, 83, 6843.
(c) Goethe O.; DiBello M.; Herzon, S. B. Nat. Chem.2022, 14, 1270.
[41] Berner H.; Vyplel H.; Schulz G.; Schneider H. Monatsh. Chem.1986, 117, 1073.
[42] Liang J.-H.; Han, X. Curr. Top. Med. Chem.2013, 13, 3131.
[43] Svetlov M. S.; Syroegin E. A.; Aleksandrova E. V.; Atkinson G. C.; Gregory S. T.; Mankin A. S.; Polikanov, Y. S. Nat. Chem. Biol.2021, 17, 412.
[44] (a) Agouridas C.; Chantot J. F.; Denis A.; D-Ambrieres S. G.; Martret, O. L. Erythromycin compounds[P]. USA: US5635485A,1995-04-21.
(b) Agouridas C.; Bonnefoy A.; Chantot J. F.; Denis A.; Le-Martret, O. Erythromycin derivatives[P]. USA: US5527780A,1993-11-01.
(c) Becourt P.; Boltri L.; Cioloca N.; De-Luigi B. S.; Mapelli L. G.; Rabaglia L.; Schwabe, D. Taste masked oral composition of telithromycin[P]. PCT: WO2004009059A1,2002-07-19.
(d) Deshpande P. B.; Luthra P. K.; Patel M. K.; Davadra, M. P. Novel polymorphs of erythromycin compound[P]. PCT: WO2007039914A2,2006-07-10.
[45] (a) Liang C.-S.; Duffield J.; Romero A.; Chiu Y.-H.; Rabuka D.; Yao S.-L.; Sucheck S.; Marby K.; Kong, Shue Y.-K.; Ichikawa Y.; Hwang, C. K. Antibacterial agents[P]. USA: US7601695B2,2005-09-09.
(b) Pereira D. E.; Fernandes, P. Parenteral formulations of macrolide antibiotics[P]. USA: US20130045937A1,2011-03-10.
(c) Duffield J.; Hwang C.-K.; Ichikawa Y.; Shue, Y. K. Antibacterial agents[P]. USA: US8012943B2,2009-04-27.
[46] Graham, D. J. N. Engl. J. Med.2006, 355, 2260.
[47] Woodhead J. L.; Yang K.; Oldach D.; MacLauchlin C.; Fernandes P.; Watkins P. B.; Siler S. Q.; Howell, B. A. Pharm. Res.2019, 36, 48.
[48] Meanwell N. A.; Georg G. I.; Wang, S. M. J. Med. Chem.2020, 63, 13197.
[49] (a) Schweitzer C. J.; Liang, T. J. ACS. Infect. Dis.2015, 1, 416.
(b) Chowdhary S.; Deka R.; Panda K.; Kumar R.; Solomon A. D.; Das J. L.; Kanoujiya. S.; Gupta A. K.; Sinha S.; Ruokolainen J.; Kesari K. K.; Gupta, P. K. Mol. Pharm.2023, 20, 3698.
[50] Belema M.; Lopez O. D.; Bender J. A.; Romine J. L.; St-Laurent D. R.; Langley D. R.; Lemm J. A.; O'BoyleII D. R.; Sun J.-H.; Wang. C.-F.; Fridell R. A.; Meanwell, N. A. J. Med. Chem.2014, 57, 1643
[51] (a) Bachand C.; Belema M.; Deon D. H.; Good A. C.; Goodrich J.; James C. A.; Lavoie R.; Lopez O. D.; Martel A.; Meanwell N. A.; Nguyen V. N.; Lee R.-J.; Ruediger E. H.; Snyder L. B.; St-Laurent D. R.; Yang F.-K.; Langley D. R.; Wang G.; Hamann, L. G. Hepatitis C Virus Inhibitors[P]. USA: US20080050336A1,2007-08-08.
(b) Bachand C.; Belema M.; Deon D. H.; Good A. C.; Goodrich J.; James C. A.; Lavoie R.; Lopez O. D.; Martel A.; Meanwell N. A.; Nguyen V. N.; Lee R.-J.; Ruediger E. H.; Snyder L. B.; St-Laurent D. R.; Yang F.-K.; Langley D. R.; Wang G.; Hamann, L. G. Hepatitis C Virus Inhibitors[P]. China: CN101558059B,2007-08-09.
(c) Pack S. K.; Tymonko S.; Patel B. P.; Natalie-JR K. J.; Belema, M. Hepatitis C Virus Inhibitors[P]. PCT: WO2011059850A1,2010-11-02.
[52] (a) Belema, M.; Nguyen, V. N.; Bachand, C.; Deon, D. H.; Goodrich, J. T.; James, C. A.; Lavoie, R.; Lopez, O. D.; Martel, A.; Romine, J. L.; Ruediger, E. H.; Snyder, L. B.; St-Laurent, D. R.; Yang, F.-K.; Zhu, J.-L.; Wong, H.-S.; Langley, D. R.; Adams, S. P.; Cantor, G. H.; Chimalakonda, A.; Fura, A.; Johnson, B. M.; Knipe, J. O.; Parker, D. D.; Santone, K. S.; Fridell, R. A.; Lemm, J. A.; O'BoyleII, D. R.; Colonno, R. J.; Gao, M.; Meanwell, N. A.; Hamann, L. G.J. Med. Chem. 2014, 57, 2013.
(b) Belema M.; Meanwell, N. A. J. Med. Chem.2014, 57, 5057.
[53] Nettles J. H.; Stanton R. A.; Broyde J.; Amblard F.; Zhang H.-W.; Zhou L.-H.; Shi. J.-X.; McBrayer T. R.; Whitaker T.; Coats S. J.; Kohler J. J.; Schinazi, R. F. J. Med. Chem.2014, 57, 10031.
[54] Link, J. O.; Taylor, J. G.; Xu, L.-H.; Mitchell, M.; Guo, H.-Y.; Liu, H.-T.; Kato, D.; Kirschberg, T.; Sun, J.-Y.; Squires, N.; Parrish, J.; Kellar, T.; Yang, Z.-Y.; Yang, C.; Matles, M.; Wang, Y. J.; Wang, K.; Cheng, G.-F.; Tian, Y.; Mogalian, E.; Mondou, E.A.; Cornpropst, M.; Perry, J.; Desai, M. C.J. Med. Chem. 2014, 57, 2033.
[55] (a) Guo H.-Y.; Kato D.; Kirschberg T. A.; Liu H.-T.; Link J. O.; Mitchell M. L.; Parrish J. P.; Squires N.; Sun J.-Y.; Taylor J.; Bacon E. M.; Canales E.; Cho A.; Cottell J. J.; Desai M. C.; Halcomb R. L.; Krygowski E. S.; Lazerwith S. E.; Liu Q.; Mackman R.; Pyun H.-J.; Saugier J. H.; Trenkle J. D.; Tse W. C.; Vivian R. W.; Schroeder S. D.; Watkins W. J.; Xu L.-H.; Yang Z.-Y.; Kellar T.; Sheng X.-N.; Clarke, M-O H.; Chou C.-H.; Graupe M.; Jin H.-L.; Mcfadden R.; Mish M. R.; Metobo S. E.; Phillips B. W.; Venkataramani, C. Antiviral compounds[P]. PCT: WO2010132601A1,2010-05-12.
(b) Delaney W. E.; Link J. O.; Mo H.-M.; Oldach D. W.; Ray A. S.; Watkins W. J.; Yang C.-Y.; Zhong, W. D. Combinations for treating HCV[P]. PCT: WO2012087596A1,2011-12-08.
(c) Ray A. S.; Watkins W. J.; Link J. O.; Oldach D. W.; Delaney- IV, W. E. Methods for treating HCV[P].PCT: WO2013040492A2,2012-09-14.
[56] DeGoey, D. A.; Randolph, J. T.; Liu. D.-C.; Pratt, J.; Hutchins, C.; Donner, P.; Krueger, A. C.; Matulenko, M.; Patel, S.; Motter, C. E.; Nelson, L.; Keddy, R.; Tufano, M.; Caspi, D. D.; Krishnan, P.; Mistry, N.; Koev, G.; Reisch, T. J.; Mondal, R.; Matias, T. P.; Gao, Y.; Beno, D. W-A.; Maring, C. J.; Molla, A.; Dumas, E.; Campbell, A.; Williams, L.; Collins, C.; Wagner, R.; Kati, W. M.J. Med. Chem. 2014, 57, 2047.
[57] (a) Degoey D. A.; Kati W. M.; Hutchins C. W.; Donner P. L.; Krueger A. C.; Randolph J. T.; Motter C. E.; Nelson L. T.; Patel S. V.; Matulenko M. A.; Keddy R. G.; Jinkerson T. K.; Soltwedel T. N.; Liu D.-C.; Pratt J. K.; Rockway T. W.; Maring C. J.; Hutchinson D. K.; Flentge C. A.; Wagner R.; Tufano MI. D.; Betebenner D. A.; Lavin M. J.; Sarris K.; Woller K. R.; Wagaw S. H.; Califano J. C.; Li W.-K.; Caspi D. D.; Bellizzi, M. E. Anti-Viral Compounds[P]. USA: US20100317568A1,2010-06-10.
(b) Pilot-Matias T. J.; Krishnan P.; Kati W. M.; Collins C. A.; Mistry N. C.; Maring C. J.; Degoey D. A.; Pratt J. K.; Liu D.-C.; Wagner, R. Methods for treating Hepatitis C[P]. PCT: WO2014047048A1,2013-09-17.
(c) Collins C. A.; Cohen D. E.; Koev G.; Krishnan P.; Pilot-Matias T. J. Compositions and methods for treating HCV[P]. USA: US10201584B1,2014-04-08.
(d) Zhu D.-H.; Nordstroem L.; Garrett, C. Anti-viral compound[P]. PCT: WO2015171162A1,2014-05-09.
(e) Chen H.-J.; Degoey D. A.; Kalthod V.; Krueger A. C.; Wagner, R. Combinations useful to treat Hepatitis C Virus[P]. PCT: WO2016134058A1,2016-02-17.
[58] (a) Coburn, C. A.; Meinke, P. T.; Chang, W.; Fandozzi, C. M.; Graham, D. J.; Hu, B.; Huang, Q.; Kargman, S.; Kozlowski, J.; Liu, R.; McCauley, J. A.; Nomeir, A. A.; Soll, R. M.; Vacca, J. P.; Wang, D.-H.; Wu, H.; Zhong, B.; Olsen, D. B.; Ludmerer, S. W.Chem. Med. Chem. 2013, 8, 1930.
(b) Yu W.-S.; Tong L.; Hu B.; Zhong B.; Hao J. L.; Ji T.; Zan S.; Coburn C. A.; Selyutin O.; Chen L.; Rokosz L.; Agrawal S.; Liu R.; Curry S.; McMonagle P.; Ingravallo P.; Appiah E. A.; Chen S.-Y.; Kozlowski, J. A. J. Med. Chem.2016, 59, 10228.
(c) Tong L.; Yu W. S.; Chen L.; Selyutin O.; Dwyer M. P.; Nair A. G.; Mazzol R.; Kim J. H.; Sha D.-Y.; Yin J.-J.; Ruck R.T.; Davies I. W.; Hu B.; Zhong B.; Ha J. L.; Ji T.; Zan S.; Liu R.; Agrawal S.; Xia E.; Curry S.; McMonagle P.; Bystol K.; Lahser F.; Carr D.; Rokosz L.; Ingravallo P.; Chen S.-Y.; Feng K.-I.; Cartwright M.; Appiah E. A.; Kozlowski, J. A. J. Med. Chem.2017, 60, 290.
[59] (a) Coburn C. A.; Mccauley J. A.; Ludmerer S. W.; Liu K.; Vacca J. P.; Wu H.; Hu B.; Soll R.; Sun F.; Wang X.-H.; Yan M.; Zhang C.-R.; Zheng M.-W.; Zhong B.; Zhu, J. Inhibitors of Hepatitis C Virus replication[P]. PCT: WO2010111483A1,2010-03-25.
(b) Kozlowski J. A.; Rosenblum S. B.; Coburn C. A.; Shankar B. B.; Anilkumar G. N.; Chen L.; Dwyer M. P.; Jiang Y.-H.; Keertikar K. M.; Lavey B. J.; Selyutin O. B.; Tong L.; Wong M.; Yang D.-Y.; Yu W.-S.; Zhou G.-W.; Wu H.; Hu B.; Zhong B.; Sun F.; Ji T.; Shen C. M. Ttracyclic indole derivatives and methods of use thereof for the treatment of viral diseases[P]. PCT: WO2012040923A1,2010-09-29.
(c) Kozlowski J. A.; Rosenblum S. B.; Coburn C. A.; Shankar B. B.; Anilkumar G. N.; Chen L.; Dwyer M. P.; Jiang Y.-H.; Keertikar K. M.; Lavey B. J.; Selyutin O. B.; Tong L.; Wong M.; Yang D.-Y.; Yu W.-S.; Zhou G.-W.; Wu H.; Hu B.; Zhong B.; Sun F.; Ji T.; Shen C.-M.; Rizvi R.; Zeng, Q. B. Tetracyclic indole derivatives for treating Hepatitis C Virus infection[P]. PCT: WO2012041014A1,2010-09-28.
(d) Mangion I.; Chen C.-Y.; Jeon I.; Chen Y.-G.; Li H.-M.; Nguyen H. N.; Maligres P. E.; Klapars A.; Zavialov I.; Yasuda, N. Process for preparing tetracyclic heterocycle compounds[P]. PCT: WO2015065821A1,2014-10-24.
(e) Lee Y.-C.; Harris D.; Moser J. D.; Mcnevin M.; Broadbent A.; Hall R.; Ericson, A. Methods for making pharmaceutical solid dosage forms of spray-dried dispersions[P]. PCT: WO2017023713A1,2016-07-29.
[60] Link J. O.; Taylor J. G.; Martin A. T.; Kato D.; Katana A. A.; Krygowski E. S.; Yang Z. Y.; Zipfel S.; Cottell J. J.; Bacon E. M.; Tran C. V.; Yang C.-Y.; Wang Y.-J.; Wang K.-W.; Zhao G.-Y.; Cheng G.-F.; Tian Y.; Gong R.-Y.; Lee Y.-J.; Yu M.; Gorman E.; Mogalian E.; Perry, J. K. Bioorg. Med. Chem. Lett.2019, 29, 2415.
[61] (a) Bacon E. M.; Cottell J. J.; Katana A. A.; Kato D.; Krygowski E. S.; Link J. O.; Taylor J.; Tran C. V.; Trejo-Martin T. A.; Yang Z.-Y.; Zipfel, S. Antiviral compounds[P]. PCT: WO2012068234A2,2011-11-16.
(b) Bacon E. M.; Cottell J. J.; Katana A. A.; Kato D.; Krygowski E. S.; Link J. O.; Taylor J.; Tran C. V.; Trejo-Martin T. A.; Yang Z.-Y.; Zipfel, S. Condensed imidazolylimidazoles as antiviral compounds[P]. PCT: WO2013075029A1,2012-11-16.
(c) Gorman E.; Mogalian E.; Oliyai R.; Stefanidis D.; Wiser L.; Zia, V. Combination formulation of two antiviral compounds[P]. USA: US20170095499A1,2016-09-30.
[62] (a) Wagner R.; Randolph J. T.; Patel S. V.; Nelson L.; Matulenko M. A.; Keddy R.; Pratt J. K.; Liu D.-C.; Krueger A. C.; Donner P. L.; Hutchinson D. K.; Flentge C.; Betebenner D.; Rockway T.; Maring C. J.; Ng T. I.; Krishnan P.; Matias T. P.; Collins. C.; Panchal N.; Reisch T.; Dekhtyar T.; Mondal R.; Stolarik D. F.; Gao Y.; Gao W.-Q.; Beno D. A.; Kati, W. M. J. Med. Chem.2018, 61, 4052.
(b) Randolph J. T.; Voight E. A.; Greszler S. N.; Uno B. E.; Newton J. N.; Gleason K. M.; Stolarik D.; Handel C. V.; Bow D. A-J.; DeGoey, D. A. J. Med. Chem.2020, 63, 11034.
[63] (a) Degoey D. A.; Kati W. M.; Hutchins C. W.; Donner P. L.; Krueger A.C.; Randolph, J T.; Motter C. E.; Nelson L. T.; Patel S. V.; Matulenko M. A.; Keddy R. G.; Jinkerson T. K.; Gao Y.; Liu D.-C.; Pratt J. K.; Rockway T. W.; Maring C. J.; Hutchinson D. K.; Flentge C. A.; Wagner R.; Tufano M. D.; Betebenner D. A.; Sarris K.; Woller K. R.; Wagaw S. H.; Califano J. C.; Li W.-K.; Caspi D. D.; Bellizzi M. E.; Carroll, W. A. Anti-viral compounds[P]. PCT: WO2012051361A1,2011-10-12
(b) Degoey D. A.; Kati W. M.; Hutchins C. W.; Donner P. L.; Krueger A. C.; Randolph J. T.; Patel S. V.; Matulenko M. A.; Keddy R. G.; Jinkerson T. K.; Liu D.-C.; Pratt J. K.; Rockway, T W.; Maring, C J.; Hutchinson D. H.; Flentge C. A.; Wagner R.; Betebenner D. A.; Sarris K.; Woller K. R.; Carroll W. A.; Gao, Y. Anti-viral compounds[P]. PCT: WO2012116257A1,2012-02-24
(c) NG-Teresa L-C.; Pilot-Matias T. J.; Kati W. M.; Krishnan P.; Maring C. J.; Mistry N. C.; Reisch T. J.; Wagner R.; Liu D.-C.; Pratt J. K.; Matulenko M. A.; Keddy. R. G. Methods for treating Hepatitis C[P]. PCT: WO2014047039A1,2013-07-19.
(d) Chen H.-J.; Degoey D. A.; Kalthod V.; Krueger A. C.; Wagner, R. Combinations useful to treat Hepatitis C Virus[P]. PCT: WO2016134058A1,2016-02-17.
[64] Zhang H.-Y.; Rao H.-Y.; Chen, H. S. J. Clin. Hepatol.2024, 40, 649 (in Chinese).
(张海莹, 饶慧瑛, 陈红松, 临床肝胆病杂志, 2024, 40, 649.)
[64] Zhang H.-Y.; Rao H.-Y.; Chen, H. S.J. Clin. Hepatol.2024,40, 649 (in Chinese).
(张海莹, 饶慧瑛, 陈红松,临床肝胆病杂志, 2024,40, 649.)
[65] (a) Zhang J.-C.; Zhang Y.-J.; Xie H.-M.; Ren Q.-Y.; Luo H.-C.; Yu T.-Z.; Tan, Y.-M. Spiro ring compound as Hepatitis C Virus (HCV) inhibitor and pharmaceutical applications thereof[P]. PCT: WO2013007106A1,2012-07-09 (in Chinese).
(张健存, 张英俊, 谢洪明, 任青云, 罗慧超, 余天柱, 谭玉梅, 作为丙型肝炎病毒抑制剂的螺环化合物[P]. PCT: WO2013007106A1, 2012-07-09.)
(b) Zhang Y.-J.; Zhang J.-C.; Xie H.-M.; Ren Q.-Y.; Tan Y.-M.; Luo H. C. Bridged ring compounds as Hepatitis C Virus (HCV) inhibitors and pharmaceutical applications thereof[P]. PCT: WO2014019344A1,2013-08-05.
(c) Zhang Y.-J.; Zhang J.-C.; Xie H.-M.; Ren Q.-Y.; Wu Xi.-W.; Luo H. C.; Fu C.-P.; Hu B.-L.; Tang C-H.; Lei Y.; Yu Q.-X.; Famg Q.-H.; Wang C. L. Spiro ring compounds as Hepatitis C Virus (HCV) inhibitors[P]. PCT: WO2014048072A1,2013-09-29.
(d) Zhang J.-C.; Zhang Y.-J.; Xie H.-M.; Ren Q.-Y.; Hu B.-L.; Fu C.-P.; Wu Xi.-W.; Li S.-F.; Wang C.-L.; Zhang Z. K. Spiro ring compound as Hepatitis C Virus (HCV) inhibitor and uses thereof field of the invention[P]. PCT: WO2014082379A1,2013-11-28.
(e) Zhang Y.-J.; Zhang J.-C.; Xie H.-M.; Ren Q.-Y.; Li S.-F.; Fu C.-P.; Hu B.-L.; Wu X.-W.; Tang, C. H. Fused ring compounds as Hepatitis C Virus inhibitors, pharmaceutical compositions and uses thereof[P]. PCT: WO2014082380A1,2013-11-28.
(f) Zhang Y.-J.; Zhang J.-C.; Xie H.-M.; Ren Q.-Y.; Wu Xi.-W.; Fu C.-P.; Hu B.-L.; Li S.-F.; Fang Q.-H.; Lei Y.; Luo, F. Spiro ring compounds as Hepatitis C Virus inhibitors, pharmaceutical compositions and uses thereof[P]. PCT: WO2014082381A1,2013-11-28.
(g) Zhang Y.-J.; Zhang J.-C.; Xie H.-M.; Ren Q.-Y.; Hu B.-L.; Li S.-F.; Wu Xi.-W.; Tang C.-H.; Wang C.-L.; Fang Q.-H.; Yu Q.-X.; Zhang, Z.-K. Bridged ring compounds as Hepatitis C Virus inhibitors, pharmaceutical compositions and uses thereof[P]. PCT: WO2014131315A1,2014-02-26.
(h) Zhang Y.-J.; Xie H.-M.; Zhang J.-C.; Hu B.-L.; Fang Q.-H.; Ren, Q. Y. Bridged ring compounds as Hepatitis C Virus inhibitors, pharmaceutical compositions and uses thereof[P]. PCT: WO2015110048A1,2015-01-22.
[66] (a) Xie H.-M.; Liu H.-W.; Zhang Y.-J.; Huang E.-H.; Feng Y.-H.; Xiang X.-W.; Fang Q.-H.; Peng Z.-H.; Dong W.-R.; An, D. L.Org. Process. Res. Dev.2021,25, 838.
(b) Rao H.-H.; Yang X.-X.; Tan Y.-W.; Ning Q.; Yang D.-K.; Wang J.-F.; Yang Y.-F.; Zheng S.-J.; Yang D.-L.; Hou J.-L.; Xie Q.; Zhao C.-Y.; Zhang L.-L.; Mao X.-R.; Sun. T.; Bai L.; Zhang F.-C.; Jin J.-L.; Zhao Y.-R.; Wang M.-R.; Xie W.; Ma Y.-J.; Quan J.; Yan X.-B.; An P.; Lin F.; Jia J.-D.; Hu X.-X.; Gong Z.-J.; Wu J.; Chen Y.-P.; Jia Z.-S.; Lin M.-H.; Wang G.-Q.; Zhu Y.-Y.; Zhang, Y.-J., ; Xie, H.-M.; Luo L.; Ren. Q.-Y.; Huang R.; Wei, L.J. Clin. Transl. Hepatol.2020,8, 255.
[67] (a) Zhang Y.-J.; Xie H.-M.; Fang Q.-H.; Liu Z.-Q.; Hu B.-L.; Zhang J. C. Compounds as Hepatitis C Virus inhibitors and pharmaceutical uses thereof[P].PCT: WO2016141890A1,2016-03-11.
(b) Zhang Y.-J.; Xie H.-M.; Fang Q.-H.; Liu Z.-Q.; Hu B.-L.; Zhang J. C. Compounds as Hepatitis C Virus inhibitors and pharmaceutical uses thereof[P]. China: CN105968101A.2016-03-11 (in Chinese).
(张英俊, 谢洪明, 方清洪, 刘志强, 胡柏林, 张健存, 作为丙型肝炎抑制剂的化合物及其在药物中的应用[P].中国专利: CN105968101A.2016-03-11.)
(c) Zhang Y.-J.; Xie H.-M.; Fang Q.-H.; Liu Z.-Q.; Hu B.-L.; Zhang J. C. Compounds as Hepatitis C Virus inhibitors and pharmaceutical uses thereof[P]. China: CN105968101B,2016-03-11 (in Chinese).
(张英俊, 谢洪明, 方清洪, 刘志强, 胡柏林, 张健存, 作为丙型肝炎抑制剂的化合物及其在药物中的应用[P].中国专利: CN105968101B, 2016-03-11.)
[68] Guillemard L.; Kaplaneris N.; Ackermann L.; Johansson, M. J.Nat. Rev. Chem.2021,5, 522.
[69] (a) Kim M.-K.; Han K.; Kim H.-S.; Park Y.-M.; Kwon H.-S.; Yoon. K.-H.; Lee, S. H.Eur. Heart. J.2017,38, 3560.
(b) Domanski M. J.; Tian X.; Wu C.-O.; Reis J. P.; Dey A. K.; Gu Y.; Zhao L.-H.; Bae S.; Liu K.; Hasan A. A.; Zimrin D.; Farkouh M. E.; Hong C.-C.; Lloyd-Jones D. M.; Fuster, V.J. Am. Coll. Cardiol.2020,76, 1507.
[70] Cerqueira N. M.; Oliveira E. F.; Gesto D. S.; Martins D. S.; Moreira C.; Moorthy H. N.; Ramos M. J.; Fernandes P. A.Biochemistry.2016,55, 5483.
[71] (a) Endo A.; Kuroda M.; Tsujita Y.J. Antibiot.1976,29, 1346.
(b) Endo A.; Tsujita Y.; Kuroda M.; Tanzawa, K.Biochim. Biophys. Acta.1979,575, 266.
(c) Endo, A.Nat.Med.2008,14, 1050.
[72] Alberts, A. W.Am. J. Cardiol.1988,62, 10J.
[73] Monaghan R. L.; Alberts A. W.; Hoffmann C. H.; Alberts S. G. Hypocholesteremic fermentation products and process of preparation[P]. USA: US4231938A,1979-06-15.
[74] Hoffman W. F.; Alberts A. W.; Anderson P. S.; Chen J.-S.; Smith R. L.; Willard, A. K.J. Med. Chem.1986,29, 849.
[75] Hoffmann W. F.; Smith R. L.; Willard, A. K. Antihypercholesterolemic compounds[P]. USA: US4444784A,1984-04-24.
[76] (a) Terahara A.; Tanaka M. ML-236B Derivatives and their preparation[P]. USA: US4346227A,1981-06-05.
(b) Tsujita S.; Terahara A.; Serizawa, N. Treatment for ischemic heart disease[P]. Japan: JP1983109416A,1981-12-21.
[77] Tabernero L.; Rodwell V. W.; Stauffacher, C. V.J. Biol. Chem.2003,278, 19933.
[78] (a) Rolf A.; Peter F.; Walter H.; Thomas P.; Hilmar B.; Dieter P.; Delf S.; Gunter, T. Substituted pyridines[P]. Europe: EP0325130A3,1989-01-09.
(b) Rolf A.; Peter F.; Walter H.; Thomas P.; Hilmar B.; Dieter P.; Delf S.; Gunter, T. Substituted pyridyl-dihydroxy-heptenoic acid and its salts[P]. USA: US5177080A,1991-11-26.
[79] (a) Kapa. P. K. 6-Substituted-4-hydroxy-tetrahydropyran-2-ones[P]. USA: US4571428A, 1983-07-08.
(b) Kathawala, F. G. Analogs of mevalolactone and derivatives thereof, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals[P]. Japan: JP1985500015A, 1983-11-18.
(c) Kathawala, F. G. Analogs of mevalolactone and derivatives thereof, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals[P]. PCT: WO1984002131A1, 1983-11-18.
[80] (a) Roth, B. D. Trans-6-[2-(3- or 4-carboxamido-substituted pyrrol-1-yl)alkyl] -4-hydroxypyran-2-one inhibitors of cholesterol synthesis[P]. USA: US4681893A, 1986-05-30.
(b) Roth, B.D. (R-(R*R*))-2-(4-fluorophenyl)-beta, delta-dihydroxy-5-(1-methylethyl-3-phenyl-4((phenylamino)-carbonyl)-1H-pyrrole-1-heptanoic acid, its lactone form and salts thereof[P]. Europe: EP1061073A1, 1990-07-20.
[81] (a) Kentaro H.; Teruyuki I.; Haruo K.; Masamichi, W. Pyrimidine derivatives as HMG-CoA reductase inhibitors[P]. Europe: EP0521471B1,1992-06-30.
(b) Paul R.; Charles H. H. Systematic inflammatory markers as diagnostic tools in the prevention of atherosclerotic diseases and as tools to aid in the selection of agents to be used for the prevention and treatment of atherosclerotic disease[P]. USA: US7030152B1,1999-08-31.
(c) Nigel, T. Crystalline bis[(E)-7-[ 4-(4- fluorophenyl)- 6-isopropyl-2-[methyl (methylsulfonyl) amino] pyrimidin -5-yl] (3R,5S)-3, 5-dihydroxyhept -6-enoic acid] calcium salt[P]. PCT: WO2000042024A1, 1999-12-23.
[82] (a) Fujikawa Y.; Suzuki M.; Iwasaki H.; Sakashita, M; Kitahara M.; Quinoline type mevalonolactones.[P]. Japan: JP2569746B2,1988-08-03.
(b) Fujikawa Y.; Suzuki M.; Iwasaki H.; Sakashita, M; Kitahara M.; Quinoline type mevalonolactones.[P]. Europe: EP0304063B1,1988-08-18.
(c) Sompong, W. Quinoline analogs of mevalonolactone and derivatives thereof[P]. USA: US5753675A, 1990-09-23.
[83] Woo J.; Christian A. H.; Burgess S. A.; Jiang Y.; Mansoor U. F.; Levin M. D.Science.2022,376,527.
[84] Gilron I.; Milne B.; Hong M.Anesthesiology.2003,99, 1198.
[85] Flower, R. J.Nat. Rev. Drug. Discov.2003,2, 179.
[86] (a) Kurumbail R. G.; Stevens A. M.; Gierse J. K.; McDonald J. J.; Stegeman R. A.; Pak. J. Y.; Gildehaus D.; Miyashiro J. M.; Penning T. D.; Seibert K.; Isakson P. C.; Stallings W. C.Nature.1996,384, 644.
(b) Plount-Price M. L.; Jorgensen, W. L.J. Am. Chem. Soc.2000,122, 9455.
[87] Chahal S.; Rani P.; Kiran; Sindhu J.; Joshi G.; Ganesan A.; Kalyaanamoorthy S.; Mayank; Kumar P.; Singh R.; Negi A.ACS. Omega.2023,8, 17446.
[88] Lazer E. S.; Miao C.-K.; Cywin C. L.; Sorcek R.; Wong H.-C.; Meng Z.-X.; Potocki I.; Hoermann M. A.; Snow R. J.; Tschantz M. A.; Kelly T. A.; McNeil D. W.; Coutts S. J.; Churchill L.; Graham A. G.; David E.; Grob P. M.; Engel W.; Meier H.; Trummlitz, G.J. Med. Chem.1997,40, 980.
[89] (a) Dai H.-X.; Stepan A. F.; Plummer M. S.; Zhang Y.-H.; Yu, J. Q.J. Am. Chem. Soc.2011,133, 7222.
(b) Ren Q.-Y.; Nie B.; Zhang Y.-J.; Zhang, J.Chin. J. Org. Chem.2018,38, 2465 (in Chinese).
(任青云, 聂飚, 张英俊, 张霁,有机化学, 2018,38, 2465.)
[90] Liu X.-H.; Park H.; Hu J.-H.; Hu Y.; Zhang Q.-L.; Wang B.-L.; Sun B.; Yeung K.-S.; Zhang F.-L.; Yu, J. Q.J. Am. Chem. Soc.2017,139, 888.
[91] Fier P. S.; Hartwig, J. F.J. Am. Chem. Soc.2014,136, 10139.
[92] Deng Z.-J.; Zhao M.-X.; Wang F.; Tang, P. P.Nat. Commun.2020,11, 2569.
[93] Ni S.-J.; Hribersek M.; Baddigam S. K.; Ingner F. J-L.; Orthaber A.; Gates P. J.; Pilarski, L. T.Angew. Chem. Int. Ed.2021,60, 6660.
[94] (a) Levy J. N.; Alegre-Requena J. V.; Liu R.-R.; Paton R. S.; McNally, A.J. Am. Chem.Soc.2020,142, 11295.
(b) Zhang X.; Nottingham K. G.; Patel C.; Alegre-Requena J. V.; Levy J. N.; Paton R. S.; McNally A.Nature.2021,594, 217.
(c) Patel C.; Mohnike M.; Hilton M. C.; McNally A.Org. Lett.2018,20, 2607.
(d) Anderson R. G.; Jett B. M.; McNally, A.Angew. Chem. Int. Ed.2018,57, 12514.
(e) Anderson R. G.; Jett B.M.; McNally A.Tetrahedron.2018,74, 3129.
(f) Hilton M. C.; Zhang X.; Boyle B. T.; Alegre-Requena J. V.; Paton R. S.; McNally A.Science.2018,362, 79.
[95] Deng X.-Y.; Rong J.; Wang L.; Vasdev N.; Zhang L.; Josephson L.; Liang, S. H.Angew. Chem. Int. Ed.2019,58, 2580.
[96] (a) Andre, M. Substituted phenoxy-alkyl-carboxylic acids and derivatives thereof[P]. German: GB1415295A, 1971-10-14.
(b) Andre, M. Esters of p-carbonylphenoxy-isobutyric acids[P]. USA: US4058552A, 1975-07-29.
[97] Chen W.; Huang Z.; Tay N. E-S.; Giglio B.; Wang M.-Z.; Wang H.; Wu Z.-H.; Nicewicz D. A.; Li Z. B.Science.2019,364, 1170.
[98] (a) Werner B.; Pascal F.; Sandra J.; William, M. P. Inhibitors of tyrosine kinases[P]. Europe: EP1532138A1;2003-07-04.
(b) Werner B.; Pascal F.; Sandra J.; William, M. P. Inhibitors of tyrosine kinases[P]. PCT: WO2004005281A1,2003-07-04.
(c) Graeme, B. Use of pyridinyl-pyrimidinylamino-benzamide derivatives for the treatment of amyloid related disorders[P].PCT: WO2005039586A1, 2004-10-26.
[99] Pipal R.W.; Stout K. T.; Musacchio P. Z.; Ren S.-M.; Graham T. J-A.; Verhoog S.; Gantert L.; Lohith T. G.; Schmitz A.; Lee H.-S.; Hesk D.; Hostetler E. D.; Davies I. W.; MacMillan D. W-C.Nature.2021,589, 542.
[100] Thompson A. M.; O'Connor P. D.; Blaser A.; Yardley V.; Maes L.; Gupta S.; Launay D.; Martin D.; Franzblau S. G.; Wan B.-J.; Wang Y.-H.; Ma Z.-K.; Denny, W. A.J. Med. Chem.2016,59, 2530.
[101] Ang C. W.; Jarrad A. M.; Cooper M. A.; Blaskovich, M. A-T.J. Med. Chem.2017,60, 7636.
[102] Mota F.; Ruiz-Bedoya C. A.; Tucker E. W.; Holt D. P.; Jesus P. D.; Lodge M. A.; Erice C.; Chen X.-Y.; Bahr M.; Flavahan K.; Kim J.; Brosnan M. K.; Ordonez A. A.; Peloquin C. A.; Dannals R. F.; Jain, S. K.Nat. Commun.2022,13, 7974.
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