JP2018531897A5 - - Google Patents

Info

Publication number

JP2018531897A5

JP2018531897A5 JP2018510377A JP2018510377A JP2018531897A5 JP 2018531897 A5 JP2018531897 A5 JP 2018531897A5 JP 2018510377 A JP2018510377 A JP 2018510377A JP 2018510377 A JP2018510377 A JP 2018510377A JP 2018531897 A5 JP2018531897 A5 JP 2018531897A5

Authority

JP

Japan

Prior art keywords

carboxamide

methoxy

dodeca

thia

pentaene

Prior art date

2016-08-26

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
• Global Dossier
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• -1 —NR 4 R 5 Chemical group 0.000 claims description 215
• 239000012216 imaging agent Substances 0.000 claims description 66
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 46
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 125000003545 alkoxy group Chemical group 0.000 claims description 30
• 125000001475 halogen functional group Chemical group 0.000 claims description 24
• 238000000034 method Methods 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 20
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 16
• 150000001875 compounds Chemical class 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 238000012636 positron electron tomography Methods 0.000 claims description 10
• 102000004169 proteins and genes Human genes 0.000 claims description 10
• 108090000623 proteins and genes Proteins 0.000 claims description 10
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 7
• 208000023105 Huntington disease Diseases 0.000 claims description 6
• 210000004556 brain Anatomy 0.000 claims description 6
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 6
• 230000004770 neurodegeneration Effects 0.000 claims description 6
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[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 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims description 5
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 5
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 5
• 150000003839 salts Chemical class 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 238000002595 magnetic resonance imaging Methods 0.000 claims description 4
• 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims description 3
• 208000037273 Pathologic Processes Diseases 0.000 claims description 3
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
• 230000009054 pathological process Effects 0.000 claims description 3
• IFPMZBBHBZQTOV-UHFFFAOYSA-N 1,3,5-trinitro-2-(2,4,6-trinitrophenyl)-4-[2,4,6-trinitro-3-(2,4,6-trinitrophenyl)phenyl]benzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(C=2C(=C(C=3C(=CC(=CC=3[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)C(=CC=2[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)=C1[N+]([O-])=O IFPMZBBHBZQTOV-UHFFFAOYSA-N 0.000 claims description 2
• 208000024827 Alzheimer disease Diseases 0.000 claims description 2
• 102000014461 Ataxins Human genes 0.000 claims description 2
• 108010078286 Ataxins Proteins 0.000 claims description 2
• 206010008025 Cerebellar ataxia Diseases 0.000 claims description 2
• 238000012879 PET imaging Methods 0.000 claims description 2
• 208000018737 Parkinson disease Diseases 0.000 claims description 2
• 208000024777 Prion disease Diseases 0.000 claims description 2
• 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims description 2
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
• 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 claims description 2
• 210000004227 basal ganglia Anatomy 0.000 claims description 2
• 210000000133 brain stem Anatomy 0.000 claims description 2
• 238000013170 computed tomography imaging Methods 0.000 claims description 2
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 2
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 2
• 210000001320 hippocampus Anatomy 0.000 claims description 2
• 238000003384 imaging method Methods 0.000 claims description 2
• 210000004185 liver Anatomy 0.000 claims description 2
• 210000003205 muscle Anatomy 0.000 claims description 2
• 238000012831 peritoneal equilibrium test Methods 0.000 claims description 2
• 238000012877 positron emission topography Methods 0.000 claims description 2
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
• 238000003325 tomography Methods 0.000 claims description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
• 238000012986 modification Methods 0.000 description 2
• 230000004048 modification Effects 0.000 description 2
• 0 CC(CC(C)(C1CCCCC1)C(*C1*2)C(*(*)*=C)=O)*1C1C2*CCC1 Chemical compound CC(CC(C)(C1CCCCC1)C(*C1*2)C(*(*)*=C)=O)*1C1C2*CCC1 0.000 description 1
• 238000007792 addition Methods 0.000 description 1
• 230000004075 alteration Effects 0.000 description 1
• 230000007170 pathology Effects 0.000 description 1
• VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1