JP2020532506A5 - - Google Patents
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- JP2020532506A5 JP2020532506A5 JP2020511347A JP2020511347A JP2020532506A5 JP 2020532506 A5 JP2020532506 A5 JP 2020532506A5 JP 2020511347 A JP2020511347 A JP 2020511347A JP 2020511347 A JP2020511347 A JP 2020511347A JP 2020532506 A5 JP2020532506 A5 JP 2020532506A5
- Authority
- JP
- Japan
- Prior art keywords
- independently
- alkyl
- optionally substituted
- heterocyclyl
- cycloalkyl
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 125
- 125000000623 heterocyclic group Chemical group 0.000 claims description 122
- 150000001875 compounds Chemical class 0.000 claims description 117
- -1 alkyl R 12 Chemical compound 0.000 claims description 116
- 125000005843 halogen group Chemical group 0.000 claims description 116
- 239000001257 hydrogen Substances 0.000 claims description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims description 90
- 125000001072 heteroaryl group Chemical group 0.000 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000000304 alkynyl group Chemical group 0.000 claims description 60
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
- 125000003342 alkenyl group Chemical group 0.000 claims description 44
- 125000004429 atom Chemical group 0.000 claims description 40
- 150000002431 hydrogen Chemical class 0.000 claims description 35
- 125000004043 oxo group Chemical group O=* 0.000 claims description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 21
- 150000001345 alkine derivatives Chemical class 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 239000000651 prodrug Substances 0.000 claims description 16
- 229940002612 prodrug Drugs 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 230000004770 neurodegeneration Effects 0.000 claims description 8
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000031277 Amaurotic familial idiocy Diseases 0.000 claims description 4
- 206010003591 Ataxia Diseases 0.000 claims description 4
- 102000014461 Ataxins Human genes 0.000 claims description 4
- 108010078286 Ataxins Proteins 0.000 claims description 4
- 206010008025 Cerebellar ataxia Diseases 0.000 claims description 4
- 206010012289 Dementia Diseases 0.000 claims description 4
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 4
- 208000002569 Machado-Joseph Disease Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 230000007850 degeneration Effects 0.000 claims description 4
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 4
- 201000010901 lateral sclerosis Diseases 0.000 claims description 4
- 208000005264 motor neuron disease Diseases 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 150000003852 triazoles Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004643 (C1-C12) haloalkoxy group Chemical group 0.000 claims description 2
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000006420 1-fluorocyclopropyl group Chemical group [H]C1([H])C([H])([H])C1(F)* 0.000 claims description 2
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 206010065040 AIDS dementia complex Diseases 0.000 claims description 2
- 208000011403 Alexander disease Diseases 0.000 claims description 2
- 241000283690 Bos taurus Species 0.000 claims description 2
- 208000014644 Brain disease Diseases 0.000 claims description 2
- 206010068597 Bulbospinal muscular atrophy congenital Diseases 0.000 claims description 2
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims description 2
- 208000004986 Diffuse Cerebral Sclerosis of Schilder Diseases 0.000 claims description 2
- 208000032274 Encephalopathy Diseases 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 102000002639 Eukaryotic Initiation Factor-2B Human genes 0.000 claims description 2
- 108010082945 Eukaryotic Initiation Factor-2B Proteins 0.000 claims description 2
- 208000003736 Gerstmann-Straussler-Scheinker Disease Diseases 0.000 claims description 2
- 206010072075 Gerstmann-Straussler-Scheinker syndrome Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 206010022489 Insulin Resistance Diseases 0.000 claims description 2
- 208000027747 Kennedy disease Diseases 0.000 claims description 2
- 208000016604 Lyme disease Diseases 0.000 claims description 2
- 206010052057 Neuroborreliosis Diseases 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 2
- 208000032319 Primary lateral sclerosis Diseases 0.000 claims description 2
- 208000024777 Prion disease Diseases 0.000 claims description 2
- 208000021811 Sandhoff disease Diseases 0.000 claims description 2
- 206010046298 Upper motor neurone lesion Diseases 0.000 claims description 2
- 208000006269 X-Linked Bulbo-Spinal Atrophy Diseases 0.000 claims description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
- 208000007502 anemia Diseases 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229960003920 cocaine Drugs 0.000 claims description 2
- 230000001149 cognitive effect Effects 0.000 claims description 2
- 230000003205 diastolic effect Effects 0.000 claims description 2
- 125000005048 dihydroisoxazolyl group Chemical group O1N(CC=C1)* 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 230000003211 malignant effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 230000003387 muscular Effects 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000006000 trichloroethyl group Chemical group 0.000 claims 1
- 0 *C(*)(C(*)(*)C(*)(OC1)I*)C1(*)N* Chemical compound *C(*)(C(*)(*)C(*)(OC1)I*)C1(*)N* 0.000 description 6
- ZZWOEUZXZBOYNR-UHFFFAOYSA-N OP(Cl)(=O)OCC(Cl)(Cl)Cl Chemical compound OP(Cl)(=O)OCC(Cl)(Cl)Cl ZZWOEUZXZBOYNR-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023030214A JP2023060020A (ja) | 2017-09-01 | 2023-02-28 | 化合物、組成物、及び、方法 |
| JP2024062313A JP2024086819A (ja) | 2017-09-01 | 2024-04-08 | 化合物、組成物、及び、方法 |
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762553750P | 2017-09-01 | 2017-09-01 | |
| US62/553,750 | 2017-09-01 | ||
| US201762609267P | 2017-12-21 | 2017-12-21 | |
| US62/609,267 | 2017-12-21 | ||
| US201862634721P | 2018-02-23 | 2018-02-23 | |
| US62/634,721 | 2018-02-23 | ||
| US201862697281P | 2018-07-12 | 2018-07-12 | |
| US62/697,281 | 2018-07-12 | ||
| PCT/US2018/049197 WO2019046779A1 (en) | 2017-09-01 | 2018-08-31 | COMPOUNDS, COMPOSITIONS AND METHODS |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023030214A Division JP2023060020A (ja) | 2017-09-01 | 2023-02-28 | 化合物、組成物、及び、方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020532506A JP2020532506A (ja) | 2020-11-12 |
| JP2020532506A5 true JP2020532506A5 (https=) | 2021-10-14 |
| JP7382308B2 JP7382308B2 (ja) | 2023-11-16 |
Family
ID=65526108
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020511347A Active JP7382308B2 (ja) | 2017-09-01 | 2018-08-31 | 化合物、組成物、及び、方法 |
| JP2023030214A Pending JP2023060020A (ja) | 2017-09-01 | 2023-02-28 | 化合物、組成物、及び、方法 |
| JP2024062313A Pending JP2024086819A (ja) | 2017-09-01 | 2024-04-08 | 化合物、組成物、及び、方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023030214A Pending JP2023060020A (ja) | 2017-09-01 | 2023-02-28 | 化合物、組成物、及び、方法 |
| JP2024062313A Pending JP2024086819A (ja) | 2017-09-01 | 2024-04-08 | 化合物、組成物、及び、方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US12139478B2 (https=) |
| EP (2) | EP3676297B1 (https=) |
| JP (3) | JP7382308B2 (https=) |
| CN (1) | CN111201245B (https=) |
| CA (1) | CA3072057A1 (https=) |
| DK (1) | DK3676297T3 (https=) |
| ES (1) | ES2952994T3 (https=) |
| FI (1) | FI3676297T3 (https=) |
| HU (1) | HUE062446T2 (https=) |
| MA (1) | MA50063A (https=) |
| PL (1) | PL3676297T3 (https=) |
| PT (1) | PT3676297T (https=) |
| SI (1) | SI3676297T1 (https=) |
| TW (1) | TW201920129A (https=) |
| WO (1) | WO2019046779A1 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3071024A1 (en) | 2017-08-09 | 2019-02-14 | Denali Therapeutics Inc. | Compounds, compositions and methods |
| CN111201245B (zh) | 2017-09-01 | 2024-04-05 | 戴纳立制药公司 | 化合物、组合物和方法 |
| WO2019090088A1 (en) | 2017-11-02 | 2019-05-09 | Calico Life Sciences Llc | Modulators of the integrated stress pathway |
| CN111757739A (zh) | 2017-12-13 | 2020-10-09 | 普拉西斯生物技术有限责任公司 | 整合应激反应路径抑制剂 |
| AU2019282253A1 (en) | 2018-06-05 | 2020-11-26 | Altos Labs, Inc. | Inhibitors of integrated stress response pathway |
| TW202545902A (zh) | 2018-10-11 | 2025-12-01 | 美商嘉來克生命科學有限責任公司 | 整合應激路徑之前藥調節劑 |
| EP3924341A4 (en) | 2019-02-13 | 2022-11-02 | Denali Therapeutics Inc. | Compounds, compositions and methods |
| SG11202108552QA (en) | 2019-02-13 | 2021-09-29 | Denali Therapeutics Inc | Compounds, compositions and methods |
| EP3959198A1 (en) * | 2019-04-23 | 2022-03-02 | Evotec International GmbH | Modulators of the integrated stress response pathway |
| MX2021012904A (es) | 2019-04-23 | 2022-01-18 | Evotec Int Gmbh | Moduladores de la via de respuesta al estres integrada. |
| PE20220572A1 (es) * | 2019-04-30 | 2022-04-20 | Calico Life Sciences Llc | Moduladores de la via integrada del estres |
| WO2020252207A1 (en) | 2019-06-12 | 2020-12-17 | Praxis Biotech LLC | Modulators of integrated stress response pathway |
| JP7699595B2 (ja) | 2020-01-28 | 2025-06-27 | エヴォテック・インターナショナル・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 統合的ストレス応答経路の調節因子 |
| CN115190813B (zh) * | 2020-03-11 | 2024-10-15 | 埃沃特克国际有限责任公司 | 整合应激反应途径的调节剂 |
| RS66455B1 (sr) | 2020-10-22 | 2025-02-28 | Evotec Int Gmbh | Modulatori puta integrisanog odgovora na stres |
| EP4232447A1 (en) * | 2020-10-22 | 2023-08-30 | Evotec International GmbH | Modulators of the integrated stress response pathway |
| CN116761803A (zh) * | 2020-10-22 | 2023-09-15 | 埃沃特克国际有限责任公司 | 整合应激反应途径的调节剂 |
| EP4232153A1 (en) | 2020-10-22 | 2023-08-30 | Evotec International GmbH | Modulators of the integrated stress response pathway |
| CN117580824A (zh) * | 2020-10-30 | 2024-02-20 | 卡里科生命科学有限责任公司 | 整合应激通路的调节剂 |
| IL302440A (en) * | 2020-10-30 | 2023-06-01 | Calico Life Sciences Llc | Combined pressure pathway modulators |
| CN116768877B (zh) * | 2022-05-30 | 2026-03-31 | 中国药科大学 | Isr抑制剂及其制备方法和应用 |
| TW202440081A (zh) * | 2023-03-14 | 2024-10-16 | 美商人福醫藥美國公司 | σ-1受體拮抗劑及其應用 |
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2018
- 2018-08-31 CN CN201880063335.4A patent/CN111201245B/zh active Active
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- 2018-08-31 EP EP23173466.6A patent/EP4248965A3/en not_active Withdrawn
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- 2018-08-31 US US16/643,168 patent/US12139478B2/en active Active
- 2018-08-31 CA CA3072057A patent/CA3072057A1/en active Pending
- 2018-08-31 WO PCT/US2018/049197 patent/WO2019046779A1/en not_active Ceased
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2023
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