Title:
QUINOLINONE DERIVATIVE COMPOUND SELECTIVELY BINDING TO CYSTEINE, PEPTIDE CONJUGATE THEREOF, AND ANTIBODY-DRUG CONJUGATE COMPRISING SAME
Document Type and Number:
WIPO Patent Application WO/2022/045773
Kind Code:
A1
Abstract:
The present invention relates to a quinolinone derivative compound selectively binding to cysteine, an amino acid- or peptide- conjugate thereof, and an antibody-drug conjugate comprising same. Since a conjugate with high chemoselectivity and high yield is formed through a radical pathway induced by visible light, the present invention can be applied in various ways to bioconjugation.
Inventors:
HONG SUNGWOO (KR)
JANG JAEBONG (KR)
CHOI HANGYEOL (KR)
KIM MYOJEONG (KR)
JANG JAEBONG (KR)
CHOI HANGYEOL (KR)
KIM MYOJEONG (KR)
Application Number:
PCT/KR2021/011382
Publication Date:
March 03, 2022
Filing Date:
August 25, 2021
Export Citation:
Assignee:
INST BASIC SCIENCE (KR)
KOREA ADVANCED INST SCI & TECH (KR)
KOREA ADVANCED INST SCI & TECH (KR)
International Classes:
C07F9/30; A61K47/68; A61P31/00; A61P35/00; A61P37/00; C07K5/02
Foreign References:
| KR20160031552A | 2016-03-22 |
Other References:
KIM INWON, MIN MINSIK, KANG DAHYE, KIM KIHO, HONG SUNGWOO: "Direct Phosphonation of Quinolinones and Coumarins Driven by the Photochemical Activity of Substrates and Products", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 19, no. 6, 17 March 2017 (2017-03-17), US , pages 1394 - 1397, XP055905436, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.7b00299
KIM INWON, PARK BOHYUN, KANG GYUMIN, KIM JIYUN, JUNG HOIMIN, LEE HYEONYEONG, BAIK MU‐HYUN, HONG SUNGWOO: "Visible‐Light‐Induced Pyridylation of Remote C(sp 3 )−H Bonds by Radical Translocation of N‐Alkoxypyridinium Salts", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, ¬VERLAG CHEMIE| :, vol. 57, no. 47, 19 November 2018 (2018-11-19), pages 15517 - 15522, XP055905438, ISSN: 1433-7851, DOI: 10.1002/anie.201809879
ZHAO YU-LONG, WU GUO-JIE, LI YOU, GAO LIAN-XUN, HAN FU-SHE: "[NiCl2(dppp)]-Catalyzed Cross-Coupling of Aryl Halides with Dialkyl Phosphite, Diphenylphosphine Oxide, and Diphenylphosphine", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 18, no. 31, 27 July 2012 (2012-07-27), DE, pages 9622 - 9627, XP055905446, ISSN: 0947-6539, DOI: 10.1002/chem.201103723
ZHANG HONGLIN, GU ZHANGXI, LI ZHENYI, PAN CHANGDUO, LI WEIPENG, HU HONGWEN, ZHU CHENGJIAN: "Silver-Catalyzed Cascade Radical Cyclization: A Direct Approach to 3,4-Disubstituted Dihydroquinolin-2(1 H )-ones through Activation of the P–H Bond and Functionalization of the C(sp 2 )–H Bond", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 81, no. 5, 4 March 2016 (2016-03-04), pages 2122 - 2127, XP055905453, ISSN: 0022-3263, DOI: 10.1021/acs.joc.5b01879
CHOI HANGYEOL, KIM MYOJEONG, JANG JAEBONG, HONG SUNGWOO: "Visible‐Light‐Induced Cysteine‐Specific Bioconjugation: Biocompatible Thiol–Ene Click Chemistry", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, ¬VERLAG CHEMIE| :, vol. 59, no. 50, 7 December 2020 (2020-12-07), pages 22514 - 22522, XP055905455, ISSN: 1433-7851, DOI: 10.1002/anie.202010217
KIM INWON, PARK BOHYUN, KANG GYUMIN, KIM JIYUN, JUNG HOIMIN, LEE HYEONYEONG, BAIK MU‐HYUN, HONG SUNGWOO: "Visible‐Light‐Induced Pyridylation of Remote C(sp 3 )−H Bonds by Radical Translocation of N‐Alkoxypyridinium Salts", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, ¬VERLAG CHEMIE| :, vol. 57, no. 47, 19 November 2018 (2018-11-19), pages 15517 - 15522, XP055905438, ISSN: 1433-7851, DOI: 10.1002/anie.201809879
ZHAO YU-LONG, WU GUO-JIE, LI YOU, GAO LIAN-XUN, HAN FU-SHE: "[NiCl2(dppp)]-Catalyzed Cross-Coupling of Aryl Halides with Dialkyl Phosphite, Diphenylphosphine Oxide, and Diphenylphosphine", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 18, no. 31, 27 July 2012 (2012-07-27), DE, pages 9622 - 9627, XP055905446, ISSN: 0947-6539, DOI: 10.1002/chem.201103723
ZHANG HONGLIN, GU ZHANGXI, LI ZHENYI, PAN CHANGDUO, LI WEIPENG, HU HONGWEN, ZHU CHENGJIAN: "Silver-Catalyzed Cascade Radical Cyclization: A Direct Approach to 3,4-Disubstituted Dihydroquinolin-2(1 H )-ones through Activation of the P–H Bond and Functionalization of the C(sp 2 )–H Bond", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 81, no. 5, 4 March 2016 (2016-03-04), pages 2122 - 2127, XP055905453, ISSN: 0022-3263, DOI: 10.1021/acs.joc.5b01879
CHOI HANGYEOL, KIM MYOJEONG, JANG JAEBONG, HONG SUNGWOO: "Visible‐Light‐Induced Cysteine‐Specific Bioconjugation: Biocompatible Thiol–Ene Click Chemistry", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, ¬VERLAG CHEMIE| :, vol. 59, no. 50, 7 December 2020 (2020-12-07), pages 22514 - 22522, XP055905455, ISSN: 1433-7851, DOI: 10.1002/anie.202010217
Attorney, Agent or Firm:
PLUS INTERNATIONAL IP LAW FIRM (KR)
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