JP2019534310A5 - - Google Patents
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- JP2019534310A5 JP2019534310A5 JP2019524868A JP2019524868A JP2019534310A5 JP 2019534310 A5 JP2019534310 A5 JP 2019534310A5 JP 2019524868 A JP2019524868 A JP 2019524868A JP 2019524868 A JP2019524868 A JP 2019524868A JP 2019534310 A5 JP2019534310 A5 JP 2019534310A5
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- 125000005843 halogen group Chemical group 0.000 claims description 118
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 114
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 103
- 125000001424 substituent group Chemical group 0.000 claims description 97
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 76
- 125000000623 heterocyclic group Chemical group 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 46
- 125000003277 amino group Chemical group 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 125000003367 polycyclic group Chemical group 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 125000002950 monocyclic group Chemical group 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 230000036542 oxidative stress Effects 0.000 claims description 14
- 230000004065 mitochondrial dysfunction Effects 0.000 claims description 13
- 150000002825 nitriles Chemical group 0.000 claims description 13
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 12
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 6
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- KZRTZNQJKJVRKK-UHFFFAOYSA-N 2-(diethylamino)-4-(2-methylphenyl)benzo[e]benzimidazol-5-one Chemical compound CCN(CC)C1=NC2=C(C(=O)C3=CC=CC=C3C2=N1)C1=C(C)C=CC=C1 KZRTZNQJKJVRKK-UHFFFAOYSA-N 0.000 claims description 2
- FUSHVQMWLCUJHF-UHFFFAOYSA-N 2-(dimethylamino)-4-(2-methylphenyl)benzo[e]benzimidazol-5-one Chemical compound CN(C)C1=NC2=C(C(=O)C3=CC=CC=C3C2=N1)C1=C(C)C=CC=C1 FUSHVQMWLCUJHF-UHFFFAOYSA-N 0.000 claims description 2
- LJIMSMKQCLDQDA-UHFFFAOYSA-N 2-(dimethylamino)-4-(2-morpholin-4-ylphenyl)benzo[e]benzimidazol-5-one Chemical compound CN(C)C1=NC2=C(C(=O)C3=CC=CC=C3C2=N1)C1=C(C=CC=C1)N1CCOCC1 LJIMSMKQCLDQDA-UHFFFAOYSA-N 0.000 claims description 2
- RQTPHAKBTKBPDS-UHFFFAOYSA-N 2-(dimethylamino)-4-(4-methylphenyl)benzo[e]benzimidazol-5-one Chemical compound CN(C)C1=NC2=C(C3=CC=C(C)C=C3)C(=O)C3=CC=CC=C3C2=N1 RQTPHAKBTKBPDS-UHFFFAOYSA-N 0.000 claims description 2
- NLIMKLXBRWLMMH-UHFFFAOYSA-N 2-(dimethylamino)-4-[2-(trifluoromethyl)phenyl]benzo[e]benzimidazol-5-one Chemical compound CN(C)C1=NC2=C(C(=O)C3=CC=CC=C3C2=N1)C1=C(C=CC=C1)C(F)(F)F NLIMKLXBRWLMMH-UHFFFAOYSA-N 0.000 claims description 2
- UIFAQSYTRGUNKX-UHFFFAOYSA-N 2-(dimethylamino)-4-[2-methyl-4-(trifluoromethoxy)phenyl]benzo[e]benzimidazol-5-one Chemical compound CN(C)C1=NC2=C(C(=O)C3=CC=CC=C3C2=N1)C1=C(C)C=C(OC(F)(F)F)C=C1 UIFAQSYTRGUNKX-UHFFFAOYSA-N 0.000 claims description 2
- RQONURUBMIPAOP-UHFFFAOYSA-N 2-(dimethylamino)-4-[2-methyl-4-(trifluoromethyl)phenyl]benzo[e]benzimidazol-5-one Chemical compound CN(C)C1=NC2=C(C(=O)C3=CC=CC=C3C2=N1)C1=C(C)C=C(C=C1)C(F)(F)F RQONURUBMIPAOP-UHFFFAOYSA-N 0.000 claims description 2
- GXGLFFFMHFQHSC-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-(dimethylamino)benzo[e]benzimidazol-5-one Chemical compound CN(C)C1=NC2=C(C(=O)C3=CC=CC=C3C2=N1)C1=C(Cl)C=CC=C1 GXGLFFFMHFQHSC-UHFFFAOYSA-N 0.000 claims description 2
- AXTVRMARIOTHDJ-UHFFFAOYSA-N 4-(2-methylphenyl)-2-(4-methylpiperazin-1-yl)benzo[e]benzimidazol-5-one Chemical compound CN1CCN(CC1)C1=NC2=C(C(=O)C3=CC=CC=C3C2=N1)C1=C(C)C=CC=C1 AXTVRMARIOTHDJ-UHFFFAOYSA-N 0.000 claims description 2
- BEPDXECDKPQHCH-UHFFFAOYSA-N N=1N(C(=C(C2=C3C(=NC(=N3)N(C)C)C3=C(C2=O)C=CC=C3)C=1C)C)C Chemical compound N=1N(C(=C(C2=C3C(=NC(=N3)N(C)C)C3=C(C2=O)C=CC=C3)C=1C)C)C BEPDXECDKPQHCH-UHFFFAOYSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- -1 Chloro-4-methoxyphenyl Chemical group 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- JLXZMLLNPNOODV-UHFFFAOYSA-N imidazol-4-one Chemical compound O=C1C=NC=N1 JLXZMLLNPNOODV-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- BENGSVASFLEXGZ-UHFFFAOYSA-N 4-(2-chloro-4-methoxyphenyl)-2-(dimethylamino)benzo[e]benzimidazol-5-one Chemical compound COC1=CC(Cl)=C(C=C1)C1=C2N=C(N=C2C2=CC=CC=C2C1=O)N(C)C BENGSVASFLEXGZ-UHFFFAOYSA-N 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 230000004064 dysfunction Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 0 *C1=C2N=C(N(*)*)N=C2c2ccccc2C1=O Chemical compound *C1=C2N=C(N(*)*)N=C2c2ccccc2C1=O 0.000 description 1
- 208000010444 Acidosis Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- QGCKIQHFSRPRRO-UHFFFAOYSA-N CN(C)C(N=C1c2c3cccc2)=NC1=C(c1cccc(OC)c1Cl)C3=O Chemical compound CN(C)C(N=C1c2c3cccc2)=NC1=C(c1cccc(OC)c1Cl)C3=O QGCKIQHFSRPRRO-UHFFFAOYSA-N 0.000 description 1
- RUINRYPKPLLIFA-UHFFFAOYSA-N Cc(cc(cc1)OC)c1C1=C2N=C(N(C)C)N=C2c(cccc2)c2C1=O Chemical compound Cc(cc(cc1)OC)c1C1=C2N=C(N(C)C)N=C2c(cccc2)c2C1=O RUINRYPKPLLIFA-UHFFFAOYSA-N 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 208000032274 Encephalopathy Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 208000035177 MELAS Diseases 0.000 description 1
- 208000002569 Machado-Joseph Disease Diseases 0.000 description 1
- 206010058799 Mitochondrial encephalomyopathy Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 230000007950 acidosis Effects 0.000 description 1
- 208000026545 acidosis disease Diseases 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 208000014188 hereditary optic neuropathy Diseases 0.000 description 1
- 208000037805 labour Diseases 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 201000010901 lateral sclerosis Diseases 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 208000005264 motor neuron disease Diseases 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022089435A JP2022107730A (ja) | 2016-11-15 | 2022-06-01 | ２－置換アミノ－ナフト［１，２－ｄ］イミダゾール－５－オン化合物またはその製薬学上許容される塩 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016222028 | 2016-11-15 | ||
| JP2016222028 | 2016-11-15 | ||
| JP2016250981 | 2016-12-26 | ||
| JP2016250981A JP2018083799A (ja) | 2016-11-15 | 2016-12-26 | ２−置換アミノ−ナフト［１，２−ｄ］イミダゾール−５−オン化合物またはその製薬学上許容される塩 |
| PCT/US2017/061879 WO2018093957A1 (en) | 2016-11-15 | 2017-11-15 | 2-substituted amino-naphth[1,2-d]imidazol-5-one compounds or pharmaceutically acceptable salts thereof cross reference to related applications |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022089435A Division JP2022107730A (ja) | 2016-11-15 | 2022-06-01 | ２－置換アミノ－ナフト［１，２－ｄ］イミダゾール－５－オン化合物またはその製薬学上許容される塩 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019534310A JP2019534310A (ja) | 2019-11-28 |
| JP2019534310A5 true JP2019534310A5 (https=) | 2021-01-21 |
| JP7083826B2 JP7083826B2 (ja) | 2022-06-13 |
Family
ID=62237007
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016250981A Pending JP2018083799A (ja) | 2016-11-15 | 2016-12-26 | ２−置換アミノ−ナフト［１，２−ｄ］イミダゾール−５−オン化合物またはその製薬学上許容される塩 |
| JP2019524868A Active JP7083826B2 (ja) | 2016-11-15 | 2017-11-15 | ２－置換アミノ－ナフト［１，２－ｄ］イミダゾール－５－オン化合物またはその製薬学上許容される塩 |
| JP2022089435A Withdrawn JP2022107730A (ja) | 2016-11-15 | 2022-06-01 | ２－置換アミノ－ナフト［１，２－ｄ］イミダゾール－５－オン化合物またはその製薬学上許容される塩 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016250981A Pending JP2018083799A (ja) | 2016-11-15 | 2016-12-26 | ２−置換アミノ−ナフト［１，２−ｄ］イミダゾール−５−オン化合物またはその製薬学上許容される塩 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022089435A Withdrawn JP2022107730A (ja) | 2016-11-15 | 2022-06-01 | ２－置換アミノ－ナフト［１，２－ｄ］イミダゾール－５－オン化合物またはその製薬学上許容される塩 |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US10738014B2 (https=) |
| EP (2) | EP3541814B1 (https=) |
| JP (3) | JP2018083799A (https=) |
| CN (1) | CN110023311B (https=) |
| CA (1) | CA3082764A1 (https=) |
| ES (1) | ES2898836T3 (https=) |
| HU (1) | HUE056922T2 (https=) |
| PL (1) | PL3541814T3 (https=) |
| PT (1) | PT3541814T (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009061744A2 (en) | 2007-11-06 | 2009-05-14 | Edison Pharmaceuticals, Inc. | 4- (p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases |
| AU2015364640B2 (en) | 2014-12-16 | 2020-08-13 | Ptc Therapeutics, Inc. | Polymorphic and amorphous forms of (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide |
| JP2018083799A (ja) | 2016-11-15 | 2018-05-31 | バイオエレクトロン テクノロジー コーポレイション | ２−置換アミノ−ナフト［１，２−ｄ］イミダゾール−５−オン化合物またはその製薬学上許容される塩 |
| US12195432B2 (en) | 2018-08-06 | 2025-01-14 | The Board Of Trustees Of The Leland Stanford Junior University | 2-arylbenzimidazoles as Ppargc1a activators for treating neurodegenerative diseases |
| KR20210076956A (ko) | 2018-10-17 | 2021-06-24 | 피티씨 테라퓨틱스, 인크. | α-시누클레인병증, 타우병증 및 기타 장애를 억제 및 치료하기 위한 2,3,5-트리메틸-6-노닐사이클로헥사-2,5-디엔-1,4-디온 |
| CA3182912A1 (en) | 2020-05-13 | 2021-11-18 | Chdi Foundation, Inc. | Htt modulators for treating huntington's disease |
| PH12022553516A1 (en) * | 2021-02-25 | 2024-06-03 | Aptabio Therapeutics Inc | Novel pyrazole derivatives |
| PE20240893A1 (es) | 2021-07-08 | 2024-04-24 | Ptc Therapeutics Inc | Composiciones farmaceuticas que comprenden 2,3,5-trimetil-6-nonilciclohexa-2,5-dien-1,4-diona |
| MX2024005933A (es) | 2021-11-17 | 2024-08-06 | Chdi Foundation Inc | Moduladores de htt pata tratar la enfermedad de huntington. |
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2016
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- 2017-11-15 EP EP17817338.1A patent/EP3541814B1/en active Active
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- 2017-11-15 JP JP2019524868A patent/JP7083826B2/ja active Active
- 2017-11-15 CN CN201780070427.0A patent/CN110023311B/zh active Active
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