JP2017521489A5 - - Google Patents

Info

Publication number

JP2017521489A5

JP2017521489A5 JP2017518041A JP2017518041A JP2017521489A5 JP 2017521489 A5 JP2017521489 A5 JP 2017521489A5 JP 2017518041 A JP2017518041 A JP 2017518041A JP 2017518041 A JP2017518041 A JP 2017518041A JP 2017521489 A5 JP2017521489 A5 JP 2017521489A5

Authority

JP

Japan

Prior art keywords

optionally substituted

methyl

chloro

ethyl

alkyl

Prior art date

2015-06-15

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Granted

Links

• Espacenet
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• -1 cyanomethoxy Chemical group 0.000 claims description 156
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 104
• 125000000217 alkyl group Chemical group 0.000 claims description 81
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 76
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
• 229910052736 halogen Inorganic materials 0.000 claims description 38
• 150000002367 halogens Chemical class 0.000 claims description 38
• 150000001875 compounds Chemical class 0.000 claims description 37
• 125000003545 alkoxy group Chemical group 0.000 claims description 35
• 125000001246 bromo group Chemical group Br* 0.000 claims description 24
• 229910052757 nitrogen Chemical group 0.000 claims description 24
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 22
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 21
• 125000004429 atom Chemical group 0.000 claims description 21
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 20
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 201000010099 disease Diseases 0.000 claims description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 239000011593 sulfur Substances 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 239000001301 oxygen Chemical group 0.000 claims description 14
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 208000015181 infectious disease Diseases 0.000 claims description 12
• 125000002252 acyl group Chemical group 0.000 claims description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims description 10
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 7
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 6
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 6
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
• 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 6
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 6
• 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 claims description 6
• 101001016865 Homo sapiens Heat shock protein HSP 90-alpha Proteins 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 230000004770 neurodegeneration Effects 0.000 claims description 6
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 208000023275 Autoimmune disease Diseases 0.000 claims description 4
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
• 208000035473 Communicable disease Diseases 0.000 claims description 4
• 241000711950 Filoviridae Species 0.000 claims description 4
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 4
• 241000712907 Retroviridae Species 0.000 claims description 4
• 241000711931 Rhabdoviridae Species 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
• 208000027866 inflammatory disease Diseases 0.000 claims description 4
• 230000002757 inflammatory effect Effects 0.000 claims description 4
• 125000004001 thioalkyl group Chemical group 0.000 claims description 4
• 208000024827 Alzheimer disease Diseases 0.000 claims description 3
• 241000700739 Hepadnaviridae Species 0.000 claims description 3
• 241000709664 Picornaviridae Species 0.000 claims description 3
• 241000700605 Viruses Species 0.000 claims description 3
• 230000002062 proliferating effect Effects 0.000 claims description 3
• 230000003612 virological effect Effects 0.000 claims description 3
• 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 2
• 241000712892 Arenaviridae Species 0.000 claims description 2
• 201000001320 Atherosclerosis Diseases 0.000 claims description 2
• 208000035143 Bacterial infection Diseases 0.000 claims description 2
• 208000004051 Chronic Traumatic Encephalopathy Diseases 0.000 claims description 2
• 241000710781 Flaviviridae Species 0.000 claims description 2
• 206010017533 Fungal infection Diseases 0.000 claims description 2
• 101710113864 Heat shock protein 90 Proteins 0.000 claims description 2
• 241001122120 Hepeviridae Species 0.000 claims description 2
• 241000700586 Herpesviridae Species 0.000 claims description 2
• 208000023105 Huntington disease Diseases 0.000 claims description 2
• 206010020751 Hypersensitivity Diseases 0.000 claims description 2
• 208000031888 Mycoses Diseases 0.000 claims description 2
• 206010028980 Neoplasm Diseases 0.000 claims description 2
• 206010033799 Paralysis Diseases 0.000 claims description 2
• 208000018737 Parkinson disease Diseases 0.000 claims description 2
• 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 2
• 241001631648 Polyomaviridae Species 0.000 claims description 2
• 241000700625 Poxviridae Species 0.000 claims description 2
• 241000702247 Reoviridae Species 0.000 claims description 2
• 208000034799 Tauopathies Diseases 0.000 claims description 2
• 208000030886 Traumatic Brain injury Diseases 0.000 claims description 2
• 208000026935 allergic disease Diseases 0.000 claims description 2
• 230000007815 allergy Effects 0.000 claims description 2
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
• 208000006673 asthma Diseases 0.000 claims description 2
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
• 201000011510 cancer Diseases 0.000 claims description 2
• 208000017004 dementia pugilistica Diseases 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 230000002401 inhibitory effect Effects 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 230000000750 progressive effect Effects 0.000 claims description 2
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
• 230000009529 traumatic brain injury Effects 0.000 claims description 2
• XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 6
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
• 125000000547 substituted alkyl group Chemical group 0.000 claims 3
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
• 241000702628 Birnaviridae Species 0.000 claims 1
• 241000712464 Orthomyxoviridae Species 0.000 claims 1
• 210000004227 basal ganglia Anatomy 0.000 claims 1
• 230000001054 cortical effect Effects 0.000 claims 1
• 230000007850 degeneration Effects 0.000 claims 1
• 238000000034 method Methods 0.000 description 24
• 0 C=C(C1)C1NC(C(S)=*)=O Chemical compound C=C(C1)C1NC(C(S)=*)=O 0.000 description 3
• 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 3
• FXBQZODCHGJETH-DAXSKMNVSA-N CC(C)/C=C(/C(C)=O)\N Chemical compound CC(C)/C=C(/C(C)=O)\N FXBQZODCHGJETH-DAXSKMNVSA-N 0.000 description 1
• 208000011990 Corticobasal Degeneration Diseases 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• 208000036142 Viral infection Diseases 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 238000007917 intracranial administration Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 238000011200 topical administration Methods 0.000 description 1
• 230000009385 viral infection Effects 0.000 description 1