Title:
PHOTOSENSITIZING DYE
Document Type and Number:
WIPO Patent Application WO/2021/261546
Kind Code:
A1
Abstract:
The present invention addresses the problem of providing a compound which has absorption in the near-infrared region and achieves a high efficiency of singlet oxygen generation (quantum yield), while exhibiting high tumor toxicity in combination with immunotoxin. The present invention provides a compound represented by formula (1) or a salt thereof. (In the formula, each of L1 and L2 independently represents a single bond, -O-, -CO-, an alkylene group having from 1 to 8 carbon atoms, a sugar chain or a combination thereof; each of R1 and R2 independently represents an alkyl group having from 1 to 8 carbon atoms, a carboxylic acid group, an amino group, a hydroxyl group, a thiol group or a biotin residue; each of R3, R4, R5, R6, R7 and R8 independently represents an alkyl group having from 1 to 8 carbon atoms, a phenyl group, a carboxylic acid group, an amino group, a hydroxyl group, a thiol group or a biotin residue; and M represents Mg, Zn, Fe, P, Si, Cu, Sn, Al, Ti, Mo or Ni.)
Inventors:
OKAMOTO AKIMITSU (JP)
DEWA WAKAKO (JP)
HAMAKUBO TAKAO (JP)
HAMABE MIKAKO (JP)
TODA NAOKO (JP)
SUDO YUKIO (JP)
DEWA WAKAKO (JP)
HAMAKUBO TAKAO (JP)
HAMABE MIKAKO (JP)
TODA NAOKO (JP)
SUDO YUKIO (JP)
Application Number:
PCT/JP2021/023911
Publication Date:
December 30, 2021
Filing Date:
June 24, 2021
Export Citation:
Assignee:
UNIV TOKYO (JP)
PHOTOQ3 INC (JP)
PHOTOQ3 INC (JP)
International Classes:
C07D487/22; A61K31/555; A61K39/395; A61K45/06; A61K47/68; A61P35/00; A61P43/00
Domestic Patent References:
| WO1996002576A1 | 1996-02-01 | |||
| WO1993012227A1 | 1993-06-24 | |||
| WO1992003918A1 | 1992-03-19 | |||
| WO1994002602A1 | 1994-02-03 | |||
| WO1994025585A1 | 1994-11-10 | |||
| WO1996034096A1 | 1996-10-31 | |||
| WO1996033735A1 | 1996-10-31 | |||
| WO1992001047A1 | 1992-01-23 | |||
| WO1992020791A1 | 1992-11-26 | |||
| WO1993006213A1 | 1993-04-01 | |||
| WO1993011236A1 | 1993-06-10 | |||
| WO1993019172A1 | 1993-09-30 | |||
| WO1995001438A1 | 1995-01-12 | |||
| WO1995015388A1 | 1995-06-08 |
Foreign References:
| JPH09501928A | 1997-02-25 | |||
| JP2004529171A | 2004-09-24 | |||
| EP0239400A2 | 1987-09-30 |
Other References:
FURUYAMA TANIYUKI, ISHII TAKASHI, IEDA NAOYA, MAEDA HAJIME, SEGI MASAHITO, UCHIYAMA MASANOBU, NAKAGAWA HIDEHIKO: ") phthalocyanines: improved hydrophilicity and exceptionally red-shifted absorption into the NIR region", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 55, no. 51, 20 June 2019 (2019-06-20), UK , pages 7311 - 7314, XP055893685, ISSN: 1359-7345, DOI: 10.1039/C9CC03022K
DRECHSLER ULF, PFAFF MIRJAM, HANACK MICHAEL: "Synthesis of Novel Functionalised Zinc Phthalocyanines Applicable in Photodynamic Therapy", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 1999, no. 12, 1 December 1999 (1999-12-01), DE , pages 3441 - 3453, XP055893680, ISSN: 1434-193X, DOI: 10.1002/(SICI)1099-0690(199912)1999:12<3441::AID-EJOC3441>3.0.CO;2-Y
HISATAKA KOBAYASHI ET AL., NATIONAL CANCER INSTITUTE
H. KATAOKA ET AL., ANN. TRANSL. MED., vol. 5, 2017, pages 183
T. J. BECK ET AL., J. PHOTOCHEM. PHOTOBIOL., vol. 87, 2007, pages 174
M. FUYUKI ET AL., J. PHOTOCHEM. PHOTOBIOL. A, vol. 252, 2013, pages 152 - 158
A. SUGANAMI ET AL., BIOORG. MED. CHEM. LETT., vol. 22, 2012, pages 7481 - 7485
S. REN ET AL., ACS APPL. MATER. INTERFACES., vol. 9, 2017, pages 31509
M. MITSUNAGA ET AL., NAT. MED., vol. 17, 2011, pages 1685 - 1691
C. CILIERS ET AL., CANCER RES., vol. 78, 2018, pages 758
K. FUJIWARA ET AL., PLOS ONE, vol. 10, 2015, pages e0125468
K. BERG ET AL., CANCER RES., vol. 59, 1999, pages 1180 - 1183
A. A. SULTAN ET AL., LANCET ONCOL, vol. 17, 2016, pages 1217 - 1229
Y. HUANG ET AL., J. PORPHYRINS PHTHALOCYANINES, vol. 22, 2018, pages 764 - 770
J. JIANG ET AL., RSC ADV., vol. 4, 2014, pages 32987 - 32996
T. GOSLINSKI ET AL., POLYHEDRON, vol. 30, 2011, pages 1538 - 1546
N. KOBAYASHI ET AL., J. AM. CHEM. SOC., vol. 133, 2011, pages 19642 - 19645
S. HIROHARA ET AL., J. PHOTOCHEM. PHOTOBIOL., B, vol. 78, 2005, pages 7 - 15
M. M. MARTINL. LINDQVIST, J. LUMIN., vol. 10, 1975, pages 381 - 390
T. OTSUKI ET AL., SCI. REP., vol. 5, 2015, pages 18577
S. DERER ET AL., J. IMMUNOL., vol. 189, 2012, pages 5230 - 5239
C. DENG ET AL., ONCOTARGET, vol. 8, 2017, pages 38568 - 38580
X. ZHOU ET AL., J. CANCER RES. CLIN. ONCOL., vol. 138, 2012, pages 1081 - 1090
DRECHSLER ULF, PFAFF MIRJAM, HANACK MICHAEL: "Synthesis of Novel Functionalised Zinc Phthalocyanines Applicable in Photodynamic Therapy", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 1999, no. 12, 1 December 1999 (1999-12-01), DE , pages 3441 - 3453, XP055893680, ISSN: 1434-193X, DOI: 10.1002/(SICI)1099-0690(199912)1999:12<3441::AID-EJOC3441>3.0.CO;2-Y
HISATAKA KOBAYASHI ET AL., NATIONAL CANCER INSTITUTE
H. KATAOKA ET AL., ANN. TRANSL. MED., vol. 5, 2017, pages 183
T. J. BECK ET AL., J. PHOTOCHEM. PHOTOBIOL., vol. 87, 2007, pages 174
M. FUYUKI ET AL., J. PHOTOCHEM. PHOTOBIOL. A, vol. 252, 2013, pages 152 - 158
A. SUGANAMI ET AL., BIOORG. MED. CHEM. LETT., vol. 22, 2012, pages 7481 - 7485
S. REN ET AL., ACS APPL. MATER. INTERFACES., vol. 9, 2017, pages 31509
M. MITSUNAGA ET AL., NAT. MED., vol. 17, 2011, pages 1685 - 1691
C. CILIERS ET AL., CANCER RES., vol. 78, 2018, pages 758
K. FUJIWARA ET AL., PLOS ONE, vol. 10, 2015, pages e0125468
K. BERG ET AL., CANCER RES., vol. 59, 1999, pages 1180 - 1183
A. A. SULTAN ET AL., LANCET ONCOL, vol. 17, 2016, pages 1217 - 1229
Y. HUANG ET AL., J. PORPHYRINS PHTHALOCYANINES, vol. 22, 2018, pages 764 - 770
J. JIANG ET AL., RSC ADV., vol. 4, 2014, pages 32987 - 32996
T. GOSLINSKI ET AL., POLYHEDRON, vol. 30, 2011, pages 1538 - 1546
N. KOBAYASHI ET AL., J. AM. CHEM. SOC., vol. 133, 2011, pages 19642 - 19645
S. HIROHARA ET AL., J. PHOTOCHEM. PHOTOBIOL., B, vol. 78, 2005, pages 7 - 15
M. M. MARTINL. LINDQVIST, J. LUMIN., vol. 10, 1975, pages 381 - 390
T. OTSUKI ET AL., SCI. REP., vol. 5, 2015, pages 18577
S. DERER ET AL., J. IMMUNOL., vol. 189, 2012, pages 5230 - 5239
C. DENG ET AL., ONCOTARGET, vol. 8, 2017, pages 38568 - 38580
X. ZHOU ET AL., J. CANCER RES. CLIN. ONCOL., vol. 138, 2012, pages 1081 - 1090
Attorney, Agent or Firm:
SIKS & CO. (JP)
Download PDF:
Previous Patent: LIQUID FOOD
Next Patent: IMAGE ANALYSIS METHOD, LEARNING IMAGE OR ANALYSIS IMAGE GENERATION METHOD, TRAINED MODEL GENERATION ...
Next Patent: IMAGE ANALYSIS METHOD, LEARNING IMAGE OR ANALYSIS IMAGE GENERATION METHOD, TRAINED MODEL GENERATION ...