Title:
ACRIDINE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2023/033165
Kind Code:
A1
Abstract:
A compound represented by formula [I] (in the formula, R12, R13, R14, R15 and R16 are the same or different, and are hydrogen, halogen, a C1-6 alkyl optionally substituted with halogen, or a C1-6 alkoxy optionally substituted with halogen; R21, R22 and R23 are the same or different, and are hydrogen, halogen, a C1-6 alkyl optionally substituted with halogen, a C1-6 alkoxy optionally substituted with halogen, sulfanyl, nitro or cyano optionally substituted with halogen; R3 is a C1-6 alkyl, etc.; and X- is an anion).
Inventors:
OHKUBO KEI (JP)
AKAO YUSUKE (JP)
KOIZUMI YASUAKI (JP)
AKAO YUSUKE (JP)
KOIZUMI YASUAKI (JP)
Application Number:
PCT/JP2022/033207
Publication Date:
March 09, 2023
Filing Date:
September 05, 2022
Export Citation:
Assignee:
UNIV OSAKA (JP)
OTSUKA PHARMA CO LTD (JP)
OTSUKA PHARMA CO LTD (JP)
International Classes:
C07D219/14; B01J31/02; B01J35/02; C07B61/00; C07C37/58; C07C39/04
Domestic Patent References:
| WO2022079055A1 | 2022-04-21 | |||
| WO2022107755A1 | 2022-05-27 |
Foreign References:
| CN113121439A | 2021-07-16 | |||
| JP2011189224A | 2011-09-29 |
Other References:
HUTSKALOVA VALERIIA, SPARR CHRISTOF: "The Versatility of the Aryne–Imine–Aryne Coupling for the Synthesis of Acridinium Photocatalysts", SYNLETT, vol. 33, no. 12, 1 July 2022 (2022-07-01), DE , pages 1180 - 1183, XP093041436, ISSN: 0936-5214, DOI: 10.1055/s-0040-1720349
YAN HONG, SONG JINSHUAI, ZHU SHAOBIN, XU HAI-CHAO: "Synthesis of Acridinium Photocatalysts via Site-Selective C–H Alkylation", CCS CHEMISTRY, vol. 3, no. 12, 1 December 2021 (2021-12-01), pages 317 - 325, XP093041498, ISSN: 2096-5745, DOI: 10.31635/ccschem.021.202000743
AMRUTA JOSHI-PANGU, FRANÇOIS LÉVESQUE, HUDSON G. ROTH, STEVEN F. OLIVER, LOUIS-CHARLES CAMPEAU, DAVID NICEWICZ, DANIEL A. DIROCCO: "Acridinium-Based Photocatalysts: A Sustainable Option in Photoredox Catalysis", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 16, 19 August 2016 (2016-08-19), pages 7244 - 7249, XP055420073, ISSN: 0022-3263, DOI: 10.1021/acs.joc.6b01240
CHUPAKHIN OLEG N.; SHCHEPOCHKIN ALEXANDER V.; CHARUSHIN VALERY N.; MAIOROVA ANNA V.; KULIKOVA TATYANA V.; SHUNYAEV KONSTANTIN YU.;: "Electrochemical Oxidative Aromatizationof 9-Substituted 9,10-Dihydroacridines: Cleavage of C-HC-X Bond", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, vol. 55, no. 10, 1 October 2019 (2019-10-01), New York , pages 956 - 963, XP036940994, ISSN: 0009-3122, DOI: 10.1007/s10593-019-02562-x
LEE IN-SOOK HAN, EUN HEE JEOUNG, MAURICE M. KREEVOY: " Primary kinetic isotope effects on hydride transfer from 1,3-dimethyl-2-phenylbenzimidazoline to NAD+ analogues", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 123, no. 31, 1 January 2001 (2001-01-01), pages 7492 - 7496, XP093041502, DOI: 10.1021/ja0151302
DATABASE REGISTRY 20 April 2021 (2021-04-20), ANONYMOUS : "Acridinium, 2,7-dibromo-10-methyl-9-(2,4,6-trimethylphenyl)-, tetrafluoroborate(1-) (1:1) (CA INDEX NAME)", XP093041513, retrieved from STN Database accession no. 2635339-83-0
DREHER SPENCER D., KRSKA SHANE W.: "Chemistry Informer Libraries: Conception, Early Experience, and Role in the Future of Cheminformatics", ACCOUNTS OF CHEMICAL RESEARCH, vol. 54, no. 7, 6 April 2021 (2021-04-06), US , pages 1586 - 1596, XP093041516, ISSN: 0001-4842, DOI: 10.1021/acs.accounts.0c00760
ORDA-ZGADZAJ MARZENA, ABRAHAM WERNER: "Photoswitchable Macrocycles Incorporating Acridane Moieties", SYNTHESIS, vol. 2007, no. 21, 1 November 2007 (2007-11-01), Suttgart , DE, pages 3345 - 3356, XP093041520, ISSN: 0039-7881, DOI: 10.1055/s-2007-990829
CAO YI-XUAN, ZHU GAN, LI YIQUN, LE BRETON NOLWENN, GOURLAOUEN CHRISTOPHE, CHOUA SYLVIE, BOIXEL JULIEN, JACQUOT DE ROUVILLE HENRI-P: "Photoinduced Arylation of Acridinium Salts: Tunable Photoredox Catalysts for C–O Bond Cleavage", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 144, no. 13, 6 April 2022 (2022-04-06), pages 5902 - 5909, XP093041524, ISSN: 0002-7863, DOI: 10.1021/jacs.1c12961
MATSUDA MARINA, UCHIYAMA MINETO, ITABASHI YUKI, OHKUBO KEI, KAMIGAITO MASAMI: "Acridinium salts as photoredox organocatalysts for photomediated cationic RAFT and DT polymerizations of vinyl ethers", POLYMER CHEMISTRY, vol. 13, no. 8, 30 December 2021 (2021-12-30), Cambridge , pages 1031 - 1039, XP093041531, ISSN: 1759-9954, DOI: 10.1039/D1PY01568K
ANGEW. CHEM. INT. ED., vol. 50, 2011, pages 8652
J. AM. CHEM. SOC., vol. 135, 2013, pages 5368
"Comprehensive Organic Transformations", 1989, CHEMICAL SOCIETY OF JAPAN, MARUZEN CO., LTD.
P.G.M. WUTST.W. GREENE: "Greene's Protective Groups in Organic Synthesis", 2006
YAN HONG, SONG JINSHUAI, ZHU SHAOBIN, XU HAI-CHAO: "Synthesis of Acridinium Photocatalysts via Site-Selective C–H Alkylation", CCS CHEMISTRY, vol. 3, no. 12, 1 December 2021 (2021-12-01), pages 317 - 325, XP093041498, ISSN: 2096-5745, DOI: 10.31635/ccschem.021.202000743
AMRUTA JOSHI-PANGU, FRANÇOIS LÉVESQUE, HUDSON G. ROTH, STEVEN F. OLIVER, LOUIS-CHARLES CAMPEAU, DAVID NICEWICZ, DANIEL A. DIROCCO: "Acridinium-Based Photocatalysts: A Sustainable Option in Photoredox Catalysis", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 16, 19 August 2016 (2016-08-19), pages 7244 - 7249, XP055420073, ISSN: 0022-3263, DOI: 10.1021/acs.joc.6b01240
CHUPAKHIN OLEG N.; SHCHEPOCHKIN ALEXANDER V.; CHARUSHIN VALERY N.; MAIOROVA ANNA V.; KULIKOVA TATYANA V.; SHUNYAEV KONSTANTIN YU.;: "Electrochemical Oxidative Aromatizationof 9-Substituted 9,10-Dihydroacridines: Cleavage of C-HC-X Bond", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, vol. 55, no. 10, 1 October 2019 (2019-10-01), New York , pages 956 - 963, XP036940994, ISSN: 0009-3122, DOI: 10.1007/s10593-019-02562-x
LEE IN-SOOK HAN, EUN HEE JEOUNG, MAURICE M. KREEVOY: " Primary kinetic isotope effects on hydride transfer from 1,3-dimethyl-2-phenylbenzimidazoline to NAD+ analogues", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 123, no. 31, 1 January 2001 (2001-01-01), pages 7492 - 7496, XP093041502, DOI: 10.1021/ja0151302
DATABASE REGISTRY 20 April 2021 (2021-04-20), ANONYMOUS : "Acridinium, 2,7-dibromo-10-methyl-9-(2,4,6-trimethylphenyl)-, tetrafluoroborate(1-) (1:1) (CA INDEX NAME)", XP093041513, retrieved from STN Database accession no. 2635339-83-0
DREHER SPENCER D., KRSKA SHANE W.: "Chemistry Informer Libraries: Conception, Early Experience, and Role in the Future of Cheminformatics", ACCOUNTS OF CHEMICAL RESEARCH, vol. 54, no. 7, 6 April 2021 (2021-04-06), US , pages 1586 - 1596, XP093041516, ISSN: 0001-4842, DOI: 10.1021/acs.accounts.0c00760
ORDA-ZGADZAJ MARZENA, ABRAHAM WERNER: "Photoswitchable Macrocycles Incorporating Acridane Moieties", SYNTHESIS, vol. 2007, no. 21, 1 November 2007 (2007-11-01), Suttgart , DE, pages 3345 - 3356, XP093041520, ISSN: 0039-7881, DOI: 10.1055/s-2007-990829
CAO YI-XUAN, ZHU GAN, LI YIQUN, LE BRETON NOLWENN, GOURLAOUEN CHRISTOPHE, CHOUA SYLVIE, BOIXEL JULIEN, JACQUOT DE ROUVILLE HENRI-P: "Photoinduced Arylation of Acridinium Salts: Tunable Photoredox Catalysts for C–O Bond Cleavage", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 144, no. 13, 6 April 2022 (2022-04-06), pages 5902 - 5909, XP093041524, ISSN: 0002-7863, DOI: 10.1021/jacs.1c12961
MATSUDA MARINA, UCHIYAMA MINETO, ITABASHI YUKI, OHKUBO KEI, KAMIGAITO MASAMI: "Acridinium salts as photoredox organocatalysts for photomediated cationic RAFT and DT polymerizations of vinyl ethers", POLYMER CHEMISTRY, vol. 13, no. 8, 30 December 2021 (2021-12-30), Cambridge , pages 1031 - 1039, XP093041531, ISSN: 1759-9954, DOI: 10.1039/D1PY01568K
ANGEW. CHEM. INT. ED., vol. 50, 2011, pages 8652
J. AM. CHEM. SOC., vol. 135, 2013, pages 5368
"Comprehensive Organic Transformations", 1989, CHEMICAL SOCIETY OF JAPAN, MARUZEN CO., LTD.
P.G.M. WUTST.W. GREENE: "Greene's Protective Groups in Organic Synthesis", 2006
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
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