EA035646B1 - Зонды для визуализации белка хантингтина - Google Patents

Info

Publication number

EA035646B1

EA035646B1 EA201790407A EA201790407A EA035646B1 EA 035646 B1 EA035646 B1 EA 035646B1 EA 201790407 A EA201790407 A EA 201790407A EA 201790407 A EA201790407 A EA 201790407A EA 035646 B1 EA035646 B1 EA 035646B1

Authority

EA

Eurasian Patent Office

Prior art keywords

pyridin

methoxy

benzoxazol

methyl

benzoxazole

Prior art date

2014-08-29

Links

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• 238000003384 imaging method Methods 0.000 title claims description 20
• 102000016252 Huntingtin Human genes 0.000 title claims description 6
• 108050004784 Huntingtin Proteins 0.000 title claims description 6
• 239000000523 sample Substances 0.000 title description 3
• 238000000034 method Methods 0.000 claims abstract description 436
• 150000001875 compounds Chemical class 0.000 claims abstract description 197
• 239000012216 imaging agent Substances 0.000 claims abstract description 34
• 150000003839 salts Chemical class 0.000 claims abstract description 31
• -1 phenoxy, benzyloxy Chemical group 0.000 claims description 323
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 168
• 125000000217 alkyl group Chemical group 0.000 claims description 129
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 120
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 81
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 62
• 125000003545 alkoxy group Chemical group 0.000 claims description 59
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 53
• 125000001072 heteroaryl group Chemical group 0.000 claims description 51
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 50
• 229910052757 nitrogen Inorganic materials 0.000 claims description 50
• 229910052736 halogen Inorganic materials 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 38
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 150000002367 halogens Chemical class 0.000 claims description 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 33
• 108090000623 proteins and genes Proteins 0.000 claims description 32
• 102000004169 proteins and genes Human genes 0.000 claims description 30
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 25
• 238000002600 positron emission tomography Methods 0.000 claims description 24
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 22
• 208000023105 Huntington disease Diseases 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 18
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
• 210000004556 brain Anatomy 0.000 claims description 17
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 15
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 14
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 14
• 210000004227 basal ganglia Anatomy 0.000 claims description 13
• 208000037273 Pathologic Processes Diseases 0.000 claims description 12
• 230000009054 pathological process Effects 0.000 claims description 12
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 150000002431 hydrogen Chemical group 0.000 claims description 10
• ZFJFJZXRNGRKKC-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(=NC=2)N)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(=NC=2)N)C=1 ZFJFJZXRNGRKKC-UHFFFAOYSA-N 0.000 claims description 9
• 230000000694 effects Effects 0.000 claims description 9
• 235000005152 nicotinamide Nutrition 0.000 claims description 9
• 239000011570 nicotinamide Substances 0.000 claims description 9
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 9
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 8
• 230000004770 neurodegeneration Effects 0.000 claims description 8
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 7
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• MPNMFPMIKIBHKP-UHFFFAOYSA-N N1=C(C=CC=C1)C(CC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1)=O Chemical compound N1=C(C=CC=C1)C(CC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1)=O MPNMFPMIKIBHKP-UHFFFAOYSA-N 0.000 claims description 7
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• 238000012879 PET imaging Methods 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
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• YCPMYYOBZAAPBL-UHFFFAOYSA-N CN1C(C=NC(=C1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1)=O Chemical compound CN1C(C=NC(=C1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1)=O YCPMYYOBZAAPBL-UHFFFAOYSA-N 0.000 claims description 6
• KRFHCVWQQZZUPP-UHFFFAOYSA-N COC=1C=C2C=CN(C(C2=CC=1)=O)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1C=C2C=CN(C(C2=CC=1)=O)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 KRFHCVWQQZZUPP-UHFFFAOYSA-N 0.000 claims description 6
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• VLFKDTKNQFDAND-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)N2CCC=3C=CC=NC=3C2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)N2CCC=3C=CC=NC=3C2)C=1 VLFKDTKNQFDAND-UHFFFAOYSA-N 0.000 claims description 6
• SGLKHXPUUXJCTL-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)N2CCNCC2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)N2CCNCC2)C=1 SGLKHXPUUXJCTL-UHFFFAOYSA-N 0.000 claims description 6
• MBIBEFJCLZGBPQ-UHFFFAOYSA-N COC=1C=NC(=NC=1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1C=NC(=NC=1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 MBIBEFJCLZGBPQ-UHFFFAOYSA-N 0.000 claims description 6
• IOKDQUAIBOQSON-UHFFFAOYSA-N COC=1N=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1N=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 IOKDQUAIBOQSON-UHFFFAOYSA-N 0.000 claims description 6
• ZCJNSWVHUFRULS-UHFFFAOYSA-N COCCOC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COCCOC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 ZCJNSWVHUFRULS-UHFFFAOYSA-N 0.000 claims description 6
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• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
• SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
• 238000002591 computed tomography Methods 0.000 claims description 6
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
• 238000002595 magnetic resonance imaging Methods 0.000 claims description 6
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
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