JP2017528520A5 - - Google Patents
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- Publication number
- JP2017528520A5 JP2017528520A5 JP2017530972A JP2017530972A JP2017528520A5 JP 2017528520 A5 JP2017528520 A5 JP 2017528520A5 JP 2017530972 A JP2017530972 A JP 2017530972A JP 2017530972 A JP2017530972 A JP 2017530972A JP 2017528520 A5 JP2017528520 A5 JP 2017528520A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- carbonitrile
- pyridine
- benzofuran
- pyridin
- Prior art date
- 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.)
- Ceased
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- 239000012216 imaging agent Substances 0.000 claims description 102
- -1 cyano, methyl Chemical group 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 238000012636 positron electron tomography Methods 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 208000023105 Huntington disease Diseases 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 230000004770 neurodegeneration Effects 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 102000004169 proteins and genes Human genes 0.000 claims description 6
- 108090000623 proteins and genes Proteins 0.000 claims description 6
- 150000003839 salts Chemical class 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 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 208000037273 Pathologic Processes Diseases 0.000 claims description 4
- 210000004556 brain Anatomy 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 238000002595 magnetic resonance imaging Methods 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 230000009054 pathological process Effects 0.000 claims description 4
- NCQIEJTXMLFJRY-UHFFFAOYSA-N (2-pyridin-3-yl-1,3-benzoxazol-5-yl)methanol Chemical compound N=1C2=CC(CO)=CC=C2OC=1C1=CC=CN=C1 NCQIEJTXMLFJRY-UHFFFAOYSA-N 0.000 claims description 3
- IMJGUZBNDBLOAK-UHFFFAOYSA-N 2-(3-bromopyridin-4-yl)-1,3-benzothiazol-6-ol Chemical compound S1C2=CC(O)=CC=C2N=C1C1=CC=NC=C1Br IMJGUZBNDBLOAK-UHFFFAOYSA-N 0.000 claims description 3
- CFGQDXDPCSUZSH-UHFFFAOYSA-N 2-(3-bromopyridin-4-yl)-6-methoxy-1,3-benzothiazole Chemical compound S1C2=CC(OC)=CC=C2N=C1C1=CC=NC=C1Br CFGQDXDPCSUZSH-UHFFFAOYSA-N 0.000 claims description 3
- IZYUYEILENMPDT-UHFFFAOYSA-N 2-(3-methylphenyl)-1,3-benzoxazol-5-amine Chemical compound CC1=CC=CC(C=2OC3=CC=C(N)C=C3N=2)=C1 IZYUYEILENMPDT-UHFFFAOYSA-N 0.000 claims description 3
- UTDCCOHXAPBGKO-UHFFFAOYSA-N 2-(3-methylphenyl)-[1,3]oxazolo[5,4-b]pyridin-6-amine Chemical group CC1=CC=CC(C=2OC3=NC=C(N)C=C3N=2)=C1 UTDCCOHXAPBGKO-UHFFFAOYSA-N 0.000 claims description 3
- ITFJBVWVZSRNHZ-UHFFFAOYSA-N 2-pyridin-3-yl-1,3-benzoxazol-5-amine Chemical compound N=1C2=CC(N)=CC=C2OC=1C1=CC=CN=C1 ITFJBVWVZSRNHZ-UHFFFAOYSA-N 0.000 claims description 3
- ZCTHPTXYNUMPGE-UHFFFAOYSA-N 2-pyridin-4-yl-1,3-benzoxazol-5-amine Chemical compound N=1C2=CC(N)=CC=C2OC=1C1=CC=NC=C1 ZCTHPTXYNUMPGE-UHFFFAOYSA-N 0.000 claims description 3
- ZIKYQHVPEWMFIU-UHFFFAOYSA-N 4-(6-methoxy-1,3-benzothiazol-2-yl)benzonitrile Chemical compound S1C2=CC(OC)=CC=C2N=C1C1=CC=C(C#N)C=C1 ZIKYQHVPEWMFIU-UHFFFAOYSA-N 0.000 claims description 3
- FBZBVYGYNCRHEM-UHFFFAOYSA-N 6-methoxy-2-(2-methoxyphenyl)-1,3-benzothiazole Chemical compound S1C2=CC(OC)=CC=C2N=C1C1=CC=CC=C1OC FBZBVYGYNCRHEM-UHFFFAOYSA-N 0.000 claims description 3
- SEQBOWWCVROFEL-UHFFFAOYSA-N BrC1=C(C#N)C(=CC=C1)C=1OC2=C(C=1)C=C(C=C2)OC Chemical compound BrC1=C(C#N)C(=CC=C1)C=1OC2=C(C=1)C=C(C=C2)OC SEQBOWWCVROFEL-UHFFFAOYSA-N 0.000 claims description 3
- LRNPUZOVQWPHOQ-UHFFFAOYSA-N BrC1=C(OC2=C1C=C(C=C2)OC)C1=CC=NC=C1 Chemical compound BrC1=C(OC2=C1C=C(C=C2)OC)C1=CC=NC=C1 LRNPUZOVQWPHOQ-UHFFFAOYSA-N 0.000 claims description 3
- HJGPLBVVFGORQM-UHFFFAOYSA-N BrC=1C=C2C(=NC=1)OC(=C2)C1=C(C#N)C=CC=C1 Chemical compound BrC=1C=C2C(=NC=1)OC(=C2)C1=C(C#N)C=CC=C1 HJGPLBVVFGORQM-UHFFFAOYSA-N 0.000 claims description 3
- XBBUCNQMPJHZDQ-UHFFFAOYSA-N BrC=1C=CC(=C(C#N)C=1)C=1OC2=C(C=1)C=C(C=C2)OC Chemical compound BrC=1C=CC(=C(C#N)C=1)C=1OC2=C(C=1)C=C(C=C2)OC XBBUCNQMPJHZDQ-UHFFFAOYSA-N 0.000 claims description 3
- VYARPIZJKMXUOL-UHFFFAOYSA-N C(#C)C=1C=NC=CC=1C=1OC2=C(C=1)C=C(C=C2)OC Chemical compound C(#C)C=1C=NC=CC=1C=1OC2=C(C=1)C=C(C=C2)OC VYARPIZJKMXUOL-UHFFFAOYSA-N 0.000 claims description 3
- DGVQJSQXYQGFOH-UHFFFAOYSA-N CN(C)C1=CC=C2N=C(SC2=C1)C1=C(C=NC=C1)C#N Chemical compound CN(C)C1=CC=C2N=C(SC2=C1)C1=C(C=NC=C1)C#N DGVQJSQXYQGFOH-UHFFFAOYSA-N 0.000 claims description 3
- LKJHDMQGRRSTQA-UHFFFAOYSA-N CN(C)CC1=C(C#N)C(=CC=C1)C=1OC2=C(C=1)C=C(C=C2)OC Chemical compound CN(C)CC1=C(C#N)C(=CC=C1)C=1OC2=C(C=1)C=C(C=C2)OC LKJHDMQGRRSTQA-UHFFFAOYSA-N 0.000 claims description 3
- ZESVXGNAJFLKLO-UHFFFAOYSA-N CN(C)CC1=CC(=C(C#N)C=C1)C=1OC2=C(C=1)C=C(C=C2)OC Chemical compound CN(C)CC1=CC(=C(C#N)C=C1)C=1OC2=C(C=1)C=C(C=C2)OC ZESVXGNAJFLKLO-UHFFFAOYSA-N 0.000 claims description 3
- KDTVAGLGTBTSGG-UHFFFAOYSA-N CNC1=C(C=CN=C1)C1=NC2=CC=C(OC)C=C2S1 Chemical compound CNC1=C(C=CN=C1)C1=NC2=CC=C(OC)C=C2S1 KDTVAGLGTBTSGG-UHFFFAOYSA-N 0.000 claims description 3
- XIHHXXIPBVQUSO-UHFFFAOYSA-N COC1=CC2=C(C=C1)N=C(O2)C1=C(C=CC=C1)C#N Chemical compound COC1=CC2=C(C=C1)N=C(O2)C1=C(C=CC=C1)C#N XIHHXXIPBVQUSO-UHFFFAOYSA-N 0.000 claims description 3
- LTJFMMOYDPGMSU-UHFFFAOYSA-N COC1=CC2=C(C=C1)N=C(O2)C1=C(C=NC=C1)C#N Chemical compound COC1=CC2=C(C=C1)N=C(O2)C1=C(C=NC=C1)C#N LTJFMMOYDPGMSU-UHFFFAOYSA-N 0.000 claims description 3
- PAYAXQUHENCLPC-UHFFFAOYSA-N COC1=CC2=C(C=C1)N=C(O2)C1=CC=CN=C1 Chemical compound COC1=CC2=C(C=C1)N=C(O2)C1=CC=CN=C1 PAYAXQUHENCLPC-UHFFFAOYSA-N 0.000 claims description 3
- LNNFLXPFGVFQGQ-UHFFFAOYSA-N COC1=CC=C2N=C(SC2=C1)C1=C(C=CC=C1)C#N Chemical compound COC1=CC=C2N=C(SC2=C1)C1=C(C=CC=C1)C#N LNNFLXPFGVFQGQ-UHFFFAOYSA-N 0.000 claims description 3
- JFDHYZWYORPCKH-UHFFFAOYSA-N COC1=CC=C2N=C(SC2=C1)C1=C(C=CN=C1)C#N Chemical compound COC1=CC=C2N=C(SC2=C1)C1=C(C=CN=C1)C#N JFDHYZWYORPCKH-UHFFFAOYSA-N 0.000 claims description 3
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- JTSQDUDQVIJBDO-UHFFFAOYSA-N COC1=CC=C2N=C(SC2=C1)C1=C(C=NC=C1)C1=CC=NN1 Chemical compound COC1=CC=C2N=C(SC2=C1)C1=C(C=NC=C1)C1=CC=NN1 JTSQDUDQVIJBDO-UHFFFAOYSA-N 0.000 claims description 3
- CJQVZZMUBSLELW-UHFFFAOYSA-N COC1=CC=C2N=C(SC2=C1)C1=C(F)C=NC=C1 Chemical compound COC1=CC=C2N=C(SC2=C1)C1=C(F)C=NC=C1 CJQVZZMUBSLELW-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
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| CN107108534B (zh) | 2014-08-29 | 2023-05-09 | Chdi基金会股份有限公司 | 用于成像亨廷顿蛋白的探针 |
| SI3197277T1 (sl) | 2014-08-29 | 2022-04-29 | Chdi Foundation, Inc. | Sonde za slikanje proteina huntingtina |
| CA2959531C (en) | 2014-08-29 | 2023-01-10 | Chdi Foundation, Inc. | Probes for imaging huntingtin protein |
| PL3340796T3 (pl) | 2015-08-28 | 2022-02-21 | Chdi Foundation, Inc. | Sondy do obrazowania białka huntingtyny |
| CN106632002A (zh) * | 2016-09-28 | 2017-05-10 | 贵州大学 | 一种依托考昔及其对照品5‑氯‑3‑(4‑(甲基磺酰基)苯基)‑2,3‑联吡啶的制备工艺 |
| GB201617339D0 (en) | 2016-10-12 | 2016-11-23 | Lytix Biopharma As | Therapeutic compounds |
| CN108178764A (zh) * | 2018-01-09 | 2018-06-19 | 天津科技大学 | 呋喃并[2,3-b]吡啶类化合物及无金属催化的合成方法 |
| US11389438B2 (en) | 2019-02-25 | 2022-07-19 | Chdi Foundation, Inc. | Compounds for targeting mutant huntingtin protein and uses thereof |
| EP4192819A1 (en) * | 2020-08-06 | 2023-06-14 | CHDI Foundation, Inc. | Heterobiaryl compounds and imaging agents for imaging huntingtin protein |
| MX2023011888A (es) * | 2021-04-08 | 2023-12-06 | Chdi Foundation Inc | Compuestos de isoindolinona y agentes de formación de imágenes para la obtencion de imágenes de la proteína huntingtina. |
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| FR2524468B1 (fr) * | 1982-04-06 | 1985-10-18 | Sandoz Sa | Nouveaux derives condenses du thiophene, leur preparation et leur utilisation comme azurants optiques |
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| CA2438032C (en) | 2003-03-14 | 2013-05-07 | University Of Pittsburgh | Benzothiazole derivative compounds, compositions and uses |
| WO2005040337A2 (en) | 2003-05-20 | 2005-05-06 | The Regents Of The University Of California | METHODS FOR BINDING AGENTS TO β-AMYLOID PLAQUES |
| WO2005016384A1 (ja) * | 2003-08-13 | 2005-02-24 | Bf Research Institute, Inc. | アミロイド蓄積性疾患のプローブ、アミロイド染色剤、アミロイド蓄積性疾患の治療および予防薬、ならびに神経原線維変化の診断プローブおよび染色剤 |
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| US7858803B2 (en) | 2007-04-27 | 2010-12-28 | The General Hospital Corporation | Imaging tracers for early detection and treatment of amyloid plaques caused by Alzheimer's disease and related disorders |
| KR101469275B1 (ko) * | 2007-06-01 | 2014-12-08 | 재단법인서울대학교산학협력재단 | 베타아밀로이드 침착의 영상화를 위한 헤테로사이클릭 인덴계열의 유도체 및 그의 방사성 동위원소 표지화합물 |
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| JP2011524864A (ja) * | 2008-05-30 | 2011-09-08 | メルク・シャープ・エンド・ドーム・コーポレイション | 新規な置換されたアザベンゾオキサゾール |
| WO2010051196A1 (en) * | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel substituted azabenzoxazoles |
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| CN107108534B (zh) | 2014-08-29 | 2023-05-09 | Chdi基金会股份有限公司 | 用于成像亨廷顿蛋白的探针 |
| SI3197277T1 (sl) | 2014-08-29 | 2022-04-29 | Chdi Foundation, Inc. | Sonde za slikanje proteina huntingtina |
| CA2959531C (en) | 2014-08-29 | 2023-01-10 | Chdi Foundation, Inc. | Probes for imaging huntingtin protein |
| PL3340796T3 (pl) | 2015-08-28 | 2022-02-21 | Chdi Foundation, Inc. | Sondy do obrazowania białka huntingtyny |
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2015
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- 2015-08-28 US US15/507,217 patent/US10907197B2/en active Active
- 2015-08-28 CN CN201580058281.9A patent/CN107105655A/zh active Pending
- 2015-08-28 CA CA2959505A patent/CA2959505A1/en not_active Abandoned
- 2015-08-28 KR KR1020177008352A patent/KR20170047341A/ko not_active Ceased
- 2015-08-28 ES ES15836157T patent/ES2818107T3/es active Active
- 2015-08-28 JP JP2017530972A patent/JP2017528520A/ja not_active Ceased
- 2015-08-28 BR BR112017004134A patent/BR112017004134A2/pt not_active Application Discontinuation
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2017
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2020
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