Title:
HETEROBIFUNCTIONAL MONODISPERSED POLYETHYLENE GLYCOL HAVING PEPTIDE LINKER
Document Type and Number:
WIPO Patent Application WO/2021/060439
Kind Code:
A1
Abstract:
The present invention addresses the problem of providing: a heterobifunctional monodispersed polyethylene glycol having two adjacent monodispersed polyethylene glycol side chains which can sustainedly release a drug upon the decomposition of a peptide linker by an enzyme in cells and, at the same time, which can effectively block the hydrophobicity of the drug; and an antibody-drug conjugate in which an antibody is conjugated with a drug using the heterobifunctional monodispersed polyethylene glycol. This heterobifunctional monodispersed polyethylene glycol is represented by formula (1). [In formula (1), each symbol is as defined in the description.]
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Inventors:
MATSUNO YUKI (JP)
YOSHIOKA HIROKI (JP)
SUZUKI AKIRA (JP)
YOSHIOKA HIROKI (JP)
SUZUKI AKIRA (JP)
Application Number:
PCT/JP2020/036195
Publication Date:
April 01, 2021
Filing Date:
September 25, 2020
Export Citation:
Assignee:
NOF CORP (JP)
International Classes:
C08G65/323; A61K47/68; C07K5/06; C07K5/08; C07K5/10; C07K16/00
Domestic Patent References:
| WO2018181059A1 | 2018-10-04 | |||
| WO2019176875A1 | 2019-09-19 | |||
| WO2005108463A2 | 2005-11-17 | |||
| WO2005058367A2 | 2005-06-30 | |||
| WO2011023883A1 | 2011-03-03 | |||
| WO2005112919A2 | 2005-12-01 | |||
| WO1989012624A2 | 1989-12-28 |
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HERMANSON, G. T.: "Bioconjugate Techniques", 2008, ACADEMIC PRESS
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KOZBOR, D. ET AL., IMMUNOL. TODAY, vol. 4, 1983, pages 72 - 79
COLE, S. P. C.ALAN R. LISS ET AL., MONOCLONAL ANTIBODIES AND CANCER THERAPY, 1985, pages 77 - 96
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KOZBOR, D. ET AL., IMMUNOLOGY TODAY, vol. 4, 1983, pages 72 - 79
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TRAIL, P. A. ET AL., SCIENCE, vol. 261, 1993, pages 212 - 215
TRAIL, P. A. ET AL., CANCER RESEARCH, vol. 57, 1997, pages 100 - 105
FRANCISCO, J. A. ET AL., CANCER RES, vol. 60, 2000, pages 3225 - 3231
BOWEN, M. A. ET AL., J. IMMUNOL., vol. 151, 1993, pages 5896 - 5906
WAHL, A. F. ET AL., CANCER RES, vol. 62, no. 13, 2002, pages 3736 - 42
ANGEW CHEM INTL. ED. ENGL., vol. 33, 1994, pages 183 - 186
ORDER, S.E. ET AL.: "Monoclonal antibodies for cancer detection and therapy", 1985, ACADEMIC PRESS, article "Analysis, results, and future prospective of the therapeutic use of radiolabeled antibody in cancer therapy", pages: 367 - 382
HELLSTROM, K. E. ET AL.: "Controlled Drug Delivery", 1987, MARCEL DEKKER, INC., article "Antibodies for drug delivery", pages: 623 - 653
THORPE, P. E. ET AL., MONOCLONAL ANTIBODIES, vol. 84, 1985, pages 475 - 506
THORPE, P.E ET AL., IMMUNOL REV, vol. 62, 1982, pages 119 - 158
AXUP, J.Y. ET AL., PROC NATL ACAD SCI, vol. 109, 2012, pages 16101 - 16106
TIAN, F. ET AL., PROC NATL ACAD SCI, vol. 111, 2014, pages 1766 - 1771
HAMBLETT, K. J. ET AL., CLIN. CANCER RES., vol. 10, 2004, pages 7063 - 7070
DORONINA, S.O. ET AL., NAT BIOTECHNOL, vol. 21, 2003, pages 778 - 784
FRANCISCO, J.A. ET AL., BLOOD, vol. 102, 2003, pages 1458 - 1465
TUMEY, L.N., ACS MED. CHEM. LETT., vol. 7, 2016, pages 977 - 982
CHEN, J. ET AL., ANAL. CHEM., vol. 85, 2013, pages 1699 - 1704
VALLIERE-DOUGLASS, J. F. ET AL., ANAL. CHEM., vol. 84, 2012, pages 2843 - 2849
BIRDSALL, R. E. ET AL., MABS, vol. 7, 2015, pages 1036 - 1044
ZHAO, R. Y. ET AL., J. MED. CHEM., vol. 54, 2011, pages 3606 - 3623
See also references of EP 4036149A4
BIOMATERIALS, vol. 22, no. 5, 2001, pages 405 - 417
HERMANSON, G. T.: "Bioconjugate Techniques", 2008, ACADEMIC PRESS
CHARI, R.V.J. ET AL., CANCER RES, vol. 52, 1992, pages 127 - 131
"PEGylated Protein Drugs: Basic Science and Clinical Applications", 2009, BIRKHAUSER
PORTARO, F. C. ET AL., BIOCHEM. J., vol. 347, 2000, pages 123 - 129
CEZARI, M.H.S. ET AL., BIOCHEM. J., vol. 368, 2002, pages 365 - 369
KYTE JDOOLITTLE RF, J MOL BIOL, vol. 157, 1982, pages 105 - 132
CHENG, T. ET AL., J CHEM INF MODEL, vol. 47, 2007, pages 2140 - 2148
MANT, C.T. ET AL., METHODS MOL BIOL, vol. 386, 2007, pages 3 - 55
MILLER, K. ET AL., J. IMMUNOL., vol. 170, 2003, pages 4854 - 4861
JANEWAY, C.TRAVERS, P.WALPORT, M.SHLOMCHIK, M.: "Immunobiology", 2001, GARLAN PUBLISHING
KOHLER, GMILSTEIN, C, NATURE, vol. 256, 1975, pages 495 - 497
KOZBOR, D. ET AL., IMMUNOL. TODAY, vol. 4, 1983, pages 72 - 79
COLE, S. P. C.ALAN R. LISS ET AL., MONOCLONAL ANTIBODIES AND CANCER THERAPY, 1985, pages 77 - 96
TENG, N. N. ET AL., PROC. NATL. ACAD. SCI. USA., vol. 80, 1983, pages 7308 - 7312
KOZBOR, D. ET AL., IMMUNOLOGY TODAY, vol. 4, 1983, pages 72 - 79
OLSSON, L. ET AL., METH. ENZYMOL., vol. 92, 1982, pages 3 - 16
MILSTEIN, C ET AL., NATURE, vol. 305, 1983, pages 537 - 539
BIRD, R. E. ET AL., SCIENCE, vol. 242, 1988, pages 423 - 442
HUSTON, J. S. ET AL., PROC. NATL. ACAD. SOT USA, vol. 85, 1988, pages 5879 - 5883
WARD, E. S. ET AL., NATURE, vol. 334, 1989, pages 544 - 554
TRAIL, P. A. ET AL., SCIENCE, vol. 261, 1993, pages 212 - 215
TRAIL, P. A. ET AL., CANCER RESEARCH, vol. 57, 1997, pages 100 - 105
FRANCISCO, J. A. ET AL., CANCER RES, vol. 60, 2000, pages 3225 - 3231
BOWEN, M. A. ET AL., J. IMMUNOL., vol. 151, 1993, pages 5896 - 5906
WAHL, A. F. ET AL., CANCER RES, vol. 62, no. 13, 2002, pages 3736 - 42
ANGEW CHEM INTL. ED. ENGL., vol. 33, 1994, pages 183 - 186
ORDER, S.E. ET AL.: "Monoclonal antibodies for cancer detection and therapy", 1985, ACADEMIC PRESS, article "Analysis, results, and future prospective of the therapeutic use of radiolabeled antibody in cancer therapy", pages: 367 - 382
HELLSTROM, K. E. ET AL.: "Controlled Drug Delivery", 1987, MARCEL DEKKER, INC., article "Antibodies for drug delivery", pages: 623 - 653
THORPE, P. E. ET AL., MONOCLONAL ANTIBODIES, vol. 84, 1985, pages 475 - 506
THORPE, P.E ET AL., IMMUNOL REV, vol. 62, 1982, pages 119 - 158
AXUP, J.Y. ET AL., PROC NATL ACAD SCI, vol. 109, 2012, pages 16101 - 16106
TIAN, F. ET AL., PROC NATL ACAD SCI, vol. 111, 2014, pages 1766 - 1771
HAMBLETT, K. J. ET AL., CLIN. CANCER RES., vol. 10, 2004, pages 7063 - 7070
DORONINA, S.O. ET AL., NAT BIOTECHNOL, vol. 21, 2003, pages 778 - 784
FRANCISCO, J.A. ET AL., BLOOD, vol. 102, 2003, pages 1458 - 1465
TUMEY, L.N., ACS MED. CHEM. LETT., vol. 7, 2016, pages 977 - 982
CHEN, J. ET AL., ANAL. CHEM., vol. 85, 2013, pages 1699 - 1704
VALLIERE-DOUGLASS, J. F. ET AL., ANAL. CHEM., vol. 84, 2012, pages 2843 - 2849
BIRDSALL, R. E. ET AL., MABS, vol. 7, 2015, pages 1036 - 1044
ZHAO, R. Y. ET AL., J. MED. CHEM., vol. 54, 2011, pages 3606 - 3623
See also references of EP 4036149A4
Attorney, Agent or Firm:
TAKASHIMA, Hajime (JP)
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