Title:
THERAPEUTIC AGENT CONTAINING PYRANODIPYRIDINE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2018/207729
Kind Code:
A1
Abstract:
A compound represented by formula (I) or a pharmaceutically acceptable salt thereof has the potential to be used as a therapeutic agent for essential tremor, small fiber neuropathy, dystonia, epilepsy associated with Alzheimer's disease, epilepsy associated with brain tumor or brain tumor.
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Inventors:
IDO KATSUTOSHI (JP)
WAKITA HISASHI (JP)
HATANAKA KEN (JP)
WAKITA HISASHI (JP)
HATANAKA KEN (JP)
Application Number:
PCT/JP2018/017619
Publication Date:
November 15, 2018
Filing Date:
May 07, 2018
Export Citation:
Assignee:
EISAI R&D MAN CO LTD (JP)
International Classes:
A61P25/14; A61K31/444; A61P43/00; C07D491/147
Domestic Patent References:
| WO2017082288A1 | 2017-05-18 |
Foreign References:
| JP2012515192A | 2012-07-05 |
Other References:
PATERSON, NE ET AL.: "Pharmacological characterization of harmaline-induced tremor activity in mice", EUR. J. PHARMACOL., vol. 616, 2009, pages 73 - 80, XP026391810
TOMIYAMA, M. ET AL.: "Upregulation of mRNAs coding for AMPA and NMDA receptor subunits and metabotropic glutamate receptors in the dorsal horn of the spinal cord in a rat model of diabetes melli tus", MOL. BRAIN RES., vol. 136, 2005, pages 275 - 281, XP004893927
HIBI, S. ET AL.: "Discovery of 2-(2-0xo-1-phenyl-5- pyridin-2-y1-1, 2-dihydropyridin-3-yl)benzoni tri le (Perampanel): A novel, noncompetitive alpha-amino-3- hydroxy-5-methyl-4-isoxazolepropanoic acid (AMPA) receptor antagonist", J. MED. CHEM., vol. 55, 2012, pages 10584 - 10600, XP055080818
NEUROLOGY, vol. 64, 2005, pages 2008 - 2020
PARKINSONISM AND RELATED DISORDERS, vol. 16, 2010, pages 604 - 607
JOURNAL OF CENTRAL NERVOUS SYSTEM DISEASE, vol. 5, 2013, pages 43 - 55
THE AMERICAN JOURNAL OF MEDICINE, vol. 115, 2003, pages l34 - 142
JOURNAL OF NEUROLOGICAL SCIENCES, vol. 349, 2015, pages l68 - 173
JOURNAL OF PHYSIOLOGY, vol. 376, 1986, pages 163 - 182
EUROPEAN JOURNAL OF PHARMACOLOGY, vol. 616, 2009, pages 73 - 80
MARTYN CN ET AL., NEUROL NEUROSURG PSYCHIATRY EPIDEMIOLOGY OF PERIPHERAL NEUROPATHY, 1997
HUGHES RC ET AL., BR MED J, vol. 324, 2002, pages 466 - 469
BASBAUM AI ET AL.: "Cellular and molecular mechanisms of pain", CELL, vol. 139, no. 2, 2009, pages 267 - 84, XP055076583, doi:10.1016/j.cell.2009.09.028
CHAN ACWILDER-SMITH EP: "Small fiber neuropathy: Getting bigger!", MUSCLE NERVE, vol. 53, no. 5, 2016, pages 671 - 82
TAVEE JZHOU L., CLEVE CLIN J MED., vol. 76, no. 5, 2009, pages 297 - 305
BAKKERS M ET AL.: "Small fibers, large impact: quality of life in small-fiber neuropathy", MUSCLE NERVE, vol. 49, no. 3, 2014, pages 329 - 36
NANNA BRIX FINNERUP ET AL.: "Handbook of Clinical Neurology", vol. 115, 2013, article "Management of painful neuropathies", pages: 279 - 290
VIKTOR R DREL ET AL.: "Evaluation of the peroxynitrite decomposition catalyst Fe(III) tetramesitylporphyrin octasulfonatc on peripheral neuropathy in a mouse model of type 1 diabetes", INT J MOL MED., vol. 20, no. 6, 2007, pages 783 - 792
TOMIYARNA M ET AL.: "Upregulation of mRNAs coding for AMPA and NMDA receptor subunits and metabotropic glutamate receptors in the dorsal horn of the spinal cord in a rat model of diabetes mellitus", BRAIN RES MOL BRAIN RES, vol. 136, no. 1-2, 2005, pages 275 - 281
BRESSMAN SB: "Dystonia genotypes, phenotypes, and classification", ADV NEUROL, vol. 94, 2004, pages 101 - 107
PAGE D ET AL.: "Quality of life in focal, segmental, and generalized dystonia", MOV DISORD, vol. 22, no. 3, 2007, pages 341 - 347
E. ZOONS ET AL.: "Botulinum toxin as treatment for focal dystonia: a systematic review of the pharmaco-therapeutic and pharmaco-economic value", JOURNAL OF NEUROLOGY, vol. 259, no. 12, 2012, pages 2519 - 2526, XP035144945, doi:10.1007/s00415-012-6510-x
TENNSARASAB P ET AL.: "Medical treatment of dystonia", J CLIN MOVE DISORDER, vol. 3, 2016, pages 19
RICHTERA ET AL., THE AMPA RECEPTOR ANTAGONIST NBQX EXERTS ANTIDYSTONIC EFFECTS IN AN ANIMAL MODEL OF IDIOPATHIC DYSTONIA, vol. 231, 1993, pages 287 - 291
HORVATH A ET AL.: "Epileptic seizures in Alzheimer disease: A review", ALZHEIMER DIS. ASSOC. DISORD., vol. 30, no. 2, 2016, pages 186 - 192
VOSSEL KA ET AL.: "Incidence and impact of subclinical epileptifonn activity in Alzheimer's disease", ANN. NEUROL., vol. 80, no. 6, 2016, pages 858 - 870
ZAREA A ET AL.: "Seizures in dominantly inherited Alzheimer disease", NEUROLOGY, vol. 87, no. 9, 2016, pages 912 - 919
JOUTSA J ET AL.: "Association between childhood-onset epilepsy and amyloid burden 5 decades later", JAMANEUROL, vol. 74, no. 5, 2017, pages 583 - 590
MARCELLO E ET AL.: "SAP97-mediated local trafficking is altered in Alzheimer disease patients' hippocampus", NEUROBIOL. AGING, vol. 33, no. 2, 2012, pages 422.el - 10
GAISLER-SALOMON I ET AL.: "Hippocampus-specific deficiency in RNA editing of GluA2 in Alzheimer's disease", NEUROBIOL. AGING, vol. 35, no. 8, 2014, pages 1785 - 1791, XP028654946, doi:10.1016/j.neurobiolaging.2014.02.018
WHITCOMB DJ ET AL.: "Intracellular oligomeric amyloid-beta rapidly regulates GluAl subunit ofAMPA receptor in the hippocampus", SCI. REP., vol. 5, 2015, pages 10934
BEZZINA C ET AL.: "Early onset of hypersynchronous network activity and expression of a marker of chronic seizures in the Tg2576 mouse model of Alzheimer's disease", PLOS ONE, vol. 10, no. 3, 2015, pages eO119910
SIWEK ME ET AL.: "Altered theta oscillations and aberrant cortical excitatory activity in the 5XFAD model of Alzheimer's disease", NEURAL PLAST, vol. 2015, 2015, pages 781731
LI Y ET AL.: "IDH1 mutation is associated with a higher preoperative seizure incidence in low-grade glioma: A systematic review and meta-analysis", SEIZURE, vol. 55, 2018, pages 76 - 82
NEAL A ET AL.: "Postoperative seizure control in patients with tumor-associated epilepsy", EPILEPSIA, vol. 57, no. 11, 2016, pages 1779 - 1788
BUCKINGHAM SC ET AL.: "Glutamate release by primary brain tumors induces epileptic activity", NAT MED., vol. 17, no. 10, 2011, pages 1269 - 1274
ISHIUCHI S ET AL.: "Blockage of Ca2+-permeable AMPA receptors suppresses migration and induces apoptosis in human glioblastoma cells", NAT. MED, vol. 8, no. 9, 2002, pages 971 - 978, XP002970007, doi:10.1038/nm746
JOUMAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, no. 35, 2011, pages 14082 - 14089
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 765916-91-4
JOURNAL OF MEDICINAL CHEMISTRY, vol. 51, no. 15, 2008, pages 4708 - 4714
NEUROSCIENCE LETTER, vol. 590, 2015, pages 84 - 90
CHAPLAN ET AL., J NEUROSCI METHODS, vol. 53, 1994, pages 55 - 63
ANNU REV PHARMACOL TOXICOL, vol. 20, 1980, pages 441 - 462
EUR J PHARMACOLOGY, vol. 231, 1993, pages 287 - 291
KIMBALL AW ET AL.: "Chemical protection against ionizing radiation. I. Sampling methods for screening compounds in radiation protection studies with mice", RADIAT RES., vol. 7, no. 1, 1957, pages 1 - 12
TOMIYAMA, M. ET AL.: "Upregulation of mRNAs coding for AMPA and NMDA receptor subunits and metabotropic glutamate receptors in the dorsal horn of the spinal cord in a rat model of diabetes melli tus", MOL. BRAIN RES., vol. 136, 2005, pages 275 - 281, XP004893927
HIBI, S. ET AL.: "Discovery of 2-(2-0xo-1-phenyl-5- pyridin-2-y1-1, 2-dihydropyridin-3-yl)benzoni tri le (Perampanel): A novel, noncompetitive alpha-amino-3- hydroxy-5-methyl-4-isoxazolepropanoic acid (AMPA) receptor antagonist", J. MED. CHEM., vol. 55, 2012, pages 10584 - 10600, XP055080818
NEUROLOGY, vol. 64, 2005, pages 2008 - 2020
PARKINSONISM AND RELATED DISORDERS, vol. 16, 2010, pages 604 - 607
JOURNAL OF CENTRAL NERVOUS SYSTEM DISEASE, vol. 5, 2013, pages 43 - 55
THE AMERICAN JOURNAL OF MEDICINE, vol. 115, 2003, pages l34 - 142
JOURNAL OF NEUROLOGICAL SCIENCES, vol. 349, 2015, pages l68 - 173
JOURNAL OF PHYSIOLOGY, vol. 376, 1986, pages 163 - 182
EUROPEAN JOURNAL OF PHARMACOLOGY, vol. 616, 2009, pages 73 - 80
MARTYN CN ET AL., NEUROL NEUROSURG PSYCHIATRY EPIDEMIOLOGY OF PERIPHERAL NEUROPATHY, 1997
HUGHES RC ET AL., BR MED J, vol. 324, 2002, pages 466 - 469
BASBAUM AI ET AL.: "Cellular and molecular mechanisms of pain", CELL, vol. 139, no. 2, 2009, pages 267 - 84, XP055076583, doi:10.1016/j.cell.2009.09.028
CHAN ACWILDER-SMITH EP: "Small fiber neuropathy: Getting bigger!", MUSCLE NERVE, vol. 53, no. 5, 2016, pages 671 - 82
TAVEE JZHOU L., CLEVE CLIN J MED., vol. 76, no. 5, 2009, pages 297 - 305
BAKKERS M ET AL.: "Small fibers, large impact: quality of life in small-fiber neuropathy", MUSCLE NERVE, vol. 49, no. 3, 2014, pages 329 - 36
NANNA BRIX FINNERUP ET AL.: "Handbook of Clinical Neurology", vol. 115, 2013, article "Management of painful neuropathies", pages: 279 - 290
VIKTOR R DREL ET AL.: "Evaluation of the peroxynitrite decomposition catalyst Fe(III) tetramesitylporphyrin octasulfonatc on peripheral neuropathy in a mouse model of type 1 diabetes", INT J MOL MED., vol. 20, no. 6, 2007, pages 783 - 792
TOMIYARNA M ET AL.: "Upregulation of mRNAs coding for AMPA and NMDA receptor subunits and metabotropic glutamate receptors in the dorsal horn of the spinal cord in a rat model of diabetes mellitus", BRAIN RES MOL BRAIN RES, vol. 136, no. 1-2, 2005, pages 275 - 281
BRESSMAN SB: "Dystonia genotypes, phenotypes, and classification", ADV NEUROL, vol. 94, 2004, pages 101 - 107
PAGE D ET AL.: "Quality of life in focal, segmental, and generalized dystonia", MOV DISORD, vol. 22, no. 3, 2007, pages 341 - 347
E. ZOONS ET AL.: "Botulinum toxin as treatment for focal dystonia: a systematic review of the pharmaco-therapeutic and pharmaco-economic value", JOURNAL OF NEUROLOGY, vol. 259, no. 12, 2012, pages 2519 - 2526, XP035144945, doi:10.1007/s00415-012-6510-x
TENNSARASAB P ET AL.: "Medical treatment of dystonia", J CLIN MOVE DISORDER, vol. 3, 2016, pages 19
RICHTERA ET AL., THE AMPA RECEPTOR ANTAGONIST NBQX EXERTS ANTIDYSTONIC EFFECTS IN AN ANIMAL MODEL OF IDIOPATHIC DYSTONIA, vol. 231, 1993, pages 287 - 291
HORVATH A ET AL.: "Epileptic seizures in Alzheimer disease: A review", ALZHEIMER DIS. ASSOC. DISORD., vol. 30, no. 2, 2016, pages 186 - 192
VOSSEL KA ET AL.: "Incidence and impact of subclinical epileptifonn activity in Alzheimer's disease", ANN. NEUROL., vol. 80, no. 6, 2016, pages 858 - 870
ZAREA A ET AL.: "Seizures in dominantly inherited Alzheimer disease", NEUROLOGY, vol. 87, no. 9, 2016, pages 912 - 919
JOUTSA J ET AL.: "Association between childhood-onset epilepsy and amyloid burden 5 decades later", JAMANEUROL, vol. 74, no. 5, 2017, pages 583 - 590
MARCELLO E ET AL.: "SAP97-mediated local trafficking is altered in Alzheimer disease patients' hippocampus", NEUROBIOL. AGING, vol. 33, no. 2, 2012, pages 422.el - 10
GAISLER-SALOMON I ET AL.: "Hippocampus-specific deficiency in RNA editing of GluA2 in Alzheimer's disease", NEUROBIOL. AGING, vol. 35, no. 8, 2014, pages 1785 - 1791, XP028654946, doi:10.1016/j.neurobiolaging.2014.02.018
WHITCOMB DJ ET AL.: "Intracellular oligomeric amyloid-beta rapidly regulates GluAl subunit ofAMPA receptor in the hippocampus", SCI. REP., vol. 5, 2015, pages 10934
BEZZINA C ET AL.: "Early onset of hypersynchronous network activity and expression of a marker of chronic seizures in the Tg2576 mouse model of Alzheimer's disease", PLOS ONE, vol. 10, no. 3, 2015, pages eO119910
SIWEK ME ET AL.: "Altered theta oscillations and aberrant cortical excitatory activity in the 5XFAD model of Alzheimer's disease", NEURAL PLAST, vol. 2015, 2015, pages 781731
LI Y ET AL.: "IDH1 mutation is associated with a higher preoperative seizure incidence in low-grade glioma: A systematic review and meta-analysis", SEIZURE, vol. 55, 2018, pages 76 - 82
NEAL A ET AL.: "Postoperative seizure control in patients with tumor-associated epilepsy", EPILEPSIA, vol. 57, no. 11, 2016, pages 1779 - 1788
BUCKINGHAM SC ET AL.: "Glutamate release by primary brain tumors induces epileptic activity", NAT MED., vol. 17, no. 10, 2011, pages 1269 - 1274
ISHIUCHI S ET AL.: "Blockage of Ca2+-permeable AMPA receptors suppresses migration and induces apoptosis in human glioblastoma cells", NAT. MED, vol. 8, no. 9, 2002, pages 971 - 978, XP002970007, doi:10.1038/nm746
JOUMAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, no. 35, 2011, pages 14082 - 14089
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 765916-91-4
JOURNAL OF MEDICINAL CHEMISTRY, vol. 51, no. 15, 2008, pages 4708 - 4714
NEUROSCIENCE LETTER, vol. 590, 2015, pages 84 - 90
CHAPLAN ET AL., J NEUROSCI METHODS, vol. 53, 1994, pages 55 - 63
ANNU REV PHARMACOL TOXICOL, vol. 20, 1980, pages 441 - 462
EUR J PHARMACOLOGY, vol. 231, 1993, pages 287 - 291
KIMBALL AW ET AL.: "Chemical protection against ionizing radiation. I. Sampling methods for screening compounds in radiation protection studies with mice", RADIAT RES., vol. 7, no. 1, 1957, pages 1 - 12
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HASEGAWA Yoshiki et al. (JP)
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