Title:
COMPOUND FOR PHOTOOXYGENATION CATALYST AND MEDICINAL COMPOSITION CONTAINING SAME
Document Type and Number:
WIPO Patent Application WO/2023/100942
Kind Code:
A1
Abstract:
[Problem] To develop an artificial catalyst capable of inhibiting aggregation of pathogenic amyloids (tau amyloids) formed by the aggregation of tau proteins, and to provide a prophylactic and therapeutic medicine for amyloid-related diseases using the same. [Solution] It is found that a compound having a structure, wherein an electron acceptor moiety containing a specific thiazole ring is linked to an electron donor moiety by intramolecular conjugation, is useful as a novel biocatalyst capable of selectively oxygenating tau amyloids upon the irradiation with light and preventing the aggregation thereof. It is also found that the aforesaid compound has excellent blood-brain barrier penetration properties and enables the oxygenation of tau amyloids in the brain upon the irradiation with light from the outside of the body.
Inventors:
KANAI MOTOMU (JP)
TOMITA TAISUKE (JP)
HORI YUKIKO (JP)
SUZUKI TAKANOBU (JP)
SOMA YOUHEI (JP)
SAWAZAKI TAKA (JP)
HIGUCHI MAKOTO (JP)
TAKUWA HIROYUKI (JP)
TOMITA TAISUKE (JP)
HORI YUKIKO (JP)
SUZUKI TAKANOBU (JP)
SOMA YOUHEI (JP)
SAWAZAKI TAKA (JP)
HIGUCHI MAKOTO (JP)
TAKUWA HIROYUKI (JP)
Application Number:
PCT/JP2022/044215
Publication Date:
June 08, 2023
Filing Date:
November 30, 2022
Export Citation:
Assignee:
UNIV TOKYO (JP)
WAKAYAMA MEDICAL UNIV (JP)
NATIONAL INSTITUTES FOR QUANTUM SCIENCE AND TECH (JP)
WAKAYAMA MEDICAL UNIV (JP)
NATIONAL INSTITUTES FOR QUANTUM SCIENCE AND TECH (JP)
International Classes:
A61K31/4985; C07D513/04; A61K41/00; A61P25/28; C07D519/00
Domestic Patent References:
| WO2014134243A1 | 2014-09-04 | |||
| WO2019026797A1 | 2019-02-07 |
Foreign References:
| JP2016079108A | 2016-05-16 | |||
| JP2015089879A | 2015-05-11 | |||
| JP2019506915A | 2019-03-14 |
Other References:
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MATSUMURA KENJI, ONO MASAHIRO, KITADA AYANE, WATANABE HIROYUKI, YOSHIMURA MASASHI, IIKUNI SHIMPEI, KIMURA HIROYUKI, OKAMOTO YOKO, : "Structure–Activity Relationship Study of Heterocyclic Phenylethenyl and Pyridinylethenyl Derivatives as Tau-Imaging Agents That Selectively Detect Neurofibrillary Tangles in Alzheimer’s Disease Brains", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 58, no. 18, 24 September 2015 (2015-09-24), US , pages 7241 - 7257, XP093069868, ISSN: 0022-2623, DOI: 10.1021/acs.jmedchem.5b00440
TOMITA TAISUKE: "Development of amyloid-selective photooxygenation catalyst — Toward the development of innovative treatments for neurodegenerative diseases", KAGAKU - CHEMISTRY, KAGAKU DOJIN, KYOTO, JP, vol. 74, no. 11, 1 November 2019 (2019-11-01), JP , pages 68 - 69, XP009547013, ISSN: 0451-1964
TANIGUCHI ATSUHIKO, SHIMIZU YUSUKE, OISAKI KOUNOSUKE, SOHMA YOUHEI, KANAI MOTOMU: "Switchable photooxygenation catalysts that sense higher-order amyloid structures", NATURE CHEMISTRY, NATURE PUBLISHING GROUP UK, LONDON, vol. 8, no. 10, 1 October 2016 (2016-10-01), London, pages 974 - 982, XP055843239, ISSN: 1755-4330, DOI: 10.1038/nchem.2550
NI JIZHI, TANIGUCHI ATSUHIKO, OZAWA SHUTA, HORI YUKIKO, KUNINOBU YOICHIRO, SAITO TAKASHI, SAIDO TAKAOMI C., TOMITA TAISUKE, SOHMA : "Near-Infrared Photoactivatable Oxygenation Catalysts of Amyloid Peptide", CHEM, CELL PRESS, US, vol. 4, no. 4, 12 April 2018 (2018-04-12), US , pages 807 - 820, XP055832151, ISSN: 2451-9294, DOI: 10.1016/j.chempr.2018.02.008
SUZUKI TAKANOBU, HORI YUKIKO, SAWAZAKI TAKA, SHIMIZU YUSUKE, NEMOTO YU, TANIGUCHI ATSUHIKO, OZAWA SHUTA, SOHMA YOUHEI, KANAI MOTOM: "Photo-oxygenation inhibits tau amyloid formation", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 55, no. 44, 4 June 2019 (2019-06-04), UK , pages 6165 - 6168, XP055832152, ISSN: 1359-7345, DOI: 10.1039/C9CC01728C
MARTIN MACKENZIE D., BAKER JEREMY D., SUNTHARALINGAM AMIRTHAA, NORDHUES BRYCE A., SHELTON LINDSEY B., ZHENG DALI, SABBAGH JONATHAN: "Inhibition of Both Hsp70 Activity and Tau Aggregation in Vitro Best Predicts Tau Lowering Activity of Small Molecules", ACS CHEMICAL BIOLOGY, vol. 11, no. 7, 15 July 2016 (2016-07-15), pages 2041 - 2048, XP093069847, ISSN: 1554-8929, DOI: 10.1021/acschembio.6b00223
ZHOU YANG, LI JUNHAO, NORDBERG AGNETA, ÅGREN HANS: "Dissecting the Binding Profile of PET Tracers to Corticobasal Degeneration Tau Fibrils", ACS CHEMICAL NEUROSCIENCE, AMERICAN CHEMICAL SOCIETY, US, vol. 12, no. 18, 15 September 2021 (2021-09-15), US , pages 3487 - 3496, XP093069956, ISSN: 1948-7193, DOI: 10.1021/acschemneuro.1c00536
MIRANDA-AZPIAZU PATRICIA; SVEDBERG MARIE; HIGUCHI MAKOTO; ONO MAIKO; JIA ZHISHENG; SUNNEMARK DAN; ELMORE CHARLES S.; SCHOU MAGNUS;: "Identification and in vitro characterization of C05-01, a PBB3 derivative with improved affinity for alpha-synuclein", BRAIN RESEARCH, ELSEVIER, AMSTERDAM, NL, vol. 1749, 18 September 2020 (2020-09-18), NL , XP086327336, ISSN: 0006-8993, DOI: 10.1016/j.brainres.2020.147131
RYUJI KYAN, KOHEI SATO NOBUYUKI MASE, TETSUO NARUMI: "26P-pm078S Synthesis and binding properties of chloroalkene-type PBB3 compounds targeting neurofibrillary tangles", 140TH ANNUAL MEETING OF THE PHARMACEUTICAL SOCIETY OF JAPAN; KYOTO, JAPAN; MARCH 25-28, 2020, PHARMACEUTICAL SOCIETY OF JAPAN, JP, vol. 140, 5 March 2020 (2020-03-05) - 28 March 2020 (2020-03-28), JP, pages 1 - 1, XP009546761
TANIGUCHI DAIKI, TOMOYUKI IMAI, TAKUMA NISHIZAWA, KOHEI SATO, NOBUYUKI MASE, TETSUO NARUMI: "23PO-am022S Chloroalkene form directed to radiolabeling with 11C. Synthetic studies of PBB3 derivatives and assessment of tau binding capacity", 139TH ANNUAL MEETING OF THE PHARMACEUTICAL SOCIETY OF JAPAN; MARCH 20-23, 2019, vol. 139, 1 March 2019 (2019-03-01) - 23 March 2019 (2019-03-23), XP009546755
TOMOYUKI IMAI, MAIKO ONO, KOHEI SATO, NOBUYUKI MASE, MASATO HIGUCHI, TETSUO NARUMI: "26X-pm01S Creation of novel amyloid-binding compounds focusing on amide bond equivalence", 138TH ANNUAL MEETING OF THE PHARMACEUTICAL SOCIETY OF JAPAN; MARCH 25-28, 2018, vol. 138, 1 March 2018 (2018-03-01) - 28 March 2018 (2018-03-28), XP009546759
TOMOYUKI IMAI, TAKUYA CHIBA, KOHEI SATO, NOBUYUKI MASE, TETSUO NARUMI: "26U-am11 Synthesis and evaluation of photostability of chloroalkene-containing PBB3 derivatives for tau imaging", 137TH ANNUAL MEETING OF THE PHARMACEUTICAL SOCIETY OF JAPAN; SENDAI, JAPAN; MARCH 24-27, 2017, vol. 137, 1 January 2017 (2017-01-01) - 27 March 2017 (2017-03-27), XP009546760
SAWAZAKI TAKA, SOHMA YOUHEI, KANAI MOTOMU: "Knoevenagel Condensation between 2-Methyl-thiazolo[4,5-b]pyrazines and Aldehydes", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, JP, vol. 70, no. 1, 1 January 2022 (2022-01-01), JP , pages 82 - 84, XP093069972, ISSN: 0009-2363, DOI: 10.1248/cpb.c21-00780
MATSUMURA KENJI, ONO MASAHIRO, KITADA AYANE, WATANABE HIROYUKI, YOSHIMURA MASASHI, IIKUNI SHIMPEI, KIMURA HIROYUKI, OKAMOTO YOKO, : "Structure–Activity Relationship Study of Heterocyclic Phenylethenyl and Pyridinylethenyl Derivatives as Tau-Imaging Agents That Selectively Detect Neurofibrillary Tangles in Alzheimer’s Disease Brains", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 58, no. 18, 24 September 2015 (2015-09-24), US , pages 7241 - 7257, XP093069868, ISSN: 0022-2623, DOI: 10.1021/acs.jmedchem.5b00440
TOMITA TAISUKE: "Development of amyloid-selective photooxygenation catalyst — Toward the development of innovative treatments for neurodegenerative diseases", KAGAKU - CHEMISTRY, KAGAKU DOJIN, KYOTO, JP, vol. 74, no. 11, 1 November 2019 (2019-11-01), JP , pages 68 - 69, XP009547013, ISSN: 0451-1964
TANIGUCHI ATSUHIKO, SHIMIZU YUSUKE, OISAKI KOUNOSUKE, SOHMA YOUHEI, KANAI MOTOMU: "Switchable photooxygenation catalysts that sense higher-order amyloid structures", NATURE CHEMISTRY, NATURE PUBLISHING GROUP UK, LONDON, vol. 8, no. 10, 1 October 2016 (2016-10-01), London, pages 974 - 982, XP055843239, ISSN: 1755-4330, DOI: 10.1038/nchem.2550
NI JIZHI, TANIGUCHI ATSUHIKO, OZAWA SHUTA, HORI YUKIKO, KUNINOBU YOICHIRO, SAITO TAKASHI, SAIDO TAKAOMI C., TOMITA TAISUKE, SOHMA : "Near-Infrared Photoactivatable Oxygenation Catalysts of Amyloid Peptide", CHEM, CELL PRESS, US, vol. 4, no. 4, 12 April 2018 (2018-04-12), US , pages 807 - 820, XP055832151, ISSN: 2451-9294, DOI: 10.1016/j.chempr.2018.02.008
SUZUKI TAKANOBU, HORI YUKIKO, SAWAZAKI TAKA, SHIMIZU YUSUKE, NEMOTO YU, TANIGUCHI ATSUHIKO, OZAWA SHUTA, SOHMA YOUHEI, KANAI MOTOM: "Photo-oxygenation inhibits tau amyloid formation", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 55, no. 44, 4 June 2019 (2019-06-04), UK , pages 6165 - 6168, XP055832152, ISSN: 1359-7345, DOI: 10.1039/C9CC01728C
MARTIN MACKENZIE D., BAKER JEREMY D., SUNTHARALINGAM AMIRTHAA, NORDHUES BRYCE A., SHELTON LINDSEY B., ZHENG DALI, SABBAGH JONATHAN: "Inhibition of Both Hsp70 Activity and Tau Aggregation in Vitro Best Predicts Tau Lowering Activity of Small Molecules", ACS CHEMICAL BIOLOGY, vol. 11, no. 7, 15 July 2016 (2016-07-15), pages 2041 - 2048, XP093069847, ISSN: 1554-8929, DOI: 10.1021/acschembio.6b00223
ZHOU YANG, LI JUNHAO, NORDBERG AGNETA, ÅGREN HANS: "Dissecting the Binding Profile of PET Tracers to Corticobasal Degeneration Tau Fibrils", ACS CHEMICAL NEUROSCIENCE, AMERICAN CHEMICAL SOCIETY, US, vol. 12, no. 18, 15 September 2021 (2021-09-15), US , pages 3487 - 3496, XP093069956, ISSN: 1948-7193, DOI: 10.1021/acschemneuro.1c00536
MIRANDA-AZPIAZU PATRICIA; SVEDBERG MARIE; HIGUCHI MAKOTO; ONO MAIKO; JIA ZHISHENG; SUNNEMARK DAN; ELMORE CHARLES S.; SCHOU MAGNUS;: "Identification and in vitro characterization of C05-01, a PBB3 derivative with improved affinity for alpha-synuclein", BRAIN RESEARCH, ELSEVIER, AMSTERDAM, NL, vol. 1749, 18 September 2020 (2020-09-18), NL , XP086327336, ISSN: 0006-8993, DOI: 10.1016/j.brainres.2020.147131
RYUJI KYAN, KOHEI SATO NOBUYUKI MASE, TETSUO NARUMI: "26P-pm078S Synthesis and binding properties of chloroalkene-type PBB3 compounds targeting neurofibrillary tangles", 140TH ANNUAL MEETING OF THE PHARMACEUTICAL SOCIETY OF JAPAN; KYOTO, JAPAN; MARCH 25-28, 2020, PHARMACEUTICAL SOCIETY OF JAPAN, JP, vol. 140, 5 March 2020 (2020-03-05) - 28 March 2020 (2020-03-28), JP, pages 1 - 1, XP009546761
TANIGUCHI DAIKI, TOMOYUKI IMAI, TAKUMA NISHIZAWA, KOHEI SATO, NOBUYUKI MASE, TETSUO NARUMI: "23PO-am022S Chloroalkene form directed to radiolabeling with 11C. Synthetic studies of PBB3 derivatives and assessment of tau binding capacity", 139TH ANNUAL MEETING OF THE PHARMACEUTICAL SOCIETY OF JAPAN; MARCH 20-23, 2019, vol. 139, 1 March 2019 (2019-03-01) - 23 March 2019 (2019-03-23), XP009546755
TOMOYUKI IMAI, MAIKO ONO, KOHEI SATO, NOBUYUKI MASE, MASATO HIGUCHI, TETSUO NARUMI: "26X-pm01S Creation of novel amyloid-binding compounds focusing on amide bond equivalence", 138TH ANNUAL MEETING OF THE PHARMACEUTICAL SOCIETY OF JAPAN; MARCH 25-28, 2018, vol. 138, 1 March 2018 (2018-03-01) - 28 March 2018 (2018-03-28), XP009546759
TOMOYUKI IMAI, TAKUYA CHIBA, KOHEI SATO, NOBUYUKI MASE, TETSUO NARUMI: "26U-am11 Synthesis and evaluation of photostability of chloroalkene-containing PBB3 derivatives for tau imaging", 137TH ANNUAL MEETING OF THE PHARMACEUTICAL SOCIETY OF JAPAN; SENDAI, JAPAN; MARCH 24-27, 2017, vol. 137, 1 January 2017 (2017-01-01) - 27 March 2017 (2017-03-27), XP009546760
SAWAZAKI TAKA, SOHMA YOUHEI, KANAI MOTOMU: "Knoevenagel Condensation between 2-Methyl-thiazolo[4,5-b]pyrazines and Aldehydes", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, JP, vol. 70, no. 1, 1 January 2022 (2022-01-01), JP , pages 82 - 84, XP093069972, ISSN: 0009-2363, DOI: 10.1248/cpb.c21-00780
Attorney, Agent or Firm:
ONO Makoto et al. (JP)
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