JP2019515017A5 - - Google Patents
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- JP2019515017A5 JP2019515017A5 JP2018560167A JP2018560167A JP2019515017A5 JP 2019515017 A5 JP2019515017 A5 JP 2019515017A5 JP 2018560167 A JP2018560167 A JP 2018560167A JP 2018560167 A JP2018560167 A JP 2018560167A JP 2019515017 A5 JP2019515017 A5 JP 2019515017A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- substituents
- heterocyclyl
- pharmaceutical composition
- compound
- 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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- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000001424 substituent group Chemical group 0.000 claims description 62
- 125000000623 heterocyclic group Chemical group 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 48
- 239000008194 pharmaceutical composition Substances 0.000 claims description 43
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 41
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 40
- 201000010099 disease Diseases 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 36
- 229910052805 deuterium Inorganic materials 0.000 claims description 34
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 32
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 32
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 206010067063 Progressive relapsing multiple sclerosis Diseases 0.000 claims description 12
- 208000007400 Relapsing-Remitting Multiple Sclerosis Diseases 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 206010063401 primary progressive multiple sclerosis Diseases 0.000 claims description 12
- 201000008628 secondary progressive multiple sclerosis Diseases 0.000 claims description 12
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- 239000006186 oral dosage form Substances 0.000 claims description 8
- 239000000651 prodrug Substances 0.000 claims description 8
- 229940002612 prodrug Drugs 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 229940124597 therapeutic agent Drugs 0.000 claims description 8
- 230000000155 isotopic effect Effects 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- -1 trimethyl pentyl Chemical group 0.000 claims description 6
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- YUMJSMWTNPFIHW-UHFFFAOYSA-N 4-methyl-6-(2,4,4-trimethylpentyl)-1H-pyridine-2-thione Chemical compound CC1=CC(NC(=C1)CC(CC(C)(C)C)C)=S YUMJSMWTNPFIHW-UHFFFAOYSA-N 0.000 claims description 4
- XILUDYZQGRRVDA-UHFFFAOYSA-N 4-methyl-6-propan-2-yl-1H-pyridine-2-thione Chemical compound C(C)(C)C1=CC(=CC(N1)=S)C XILUDYZQGRRVDA-UHFFFAOYSA-N 0.000 claims description 4
- NWVHDMLGBYULFR-UHFFFAOYSA-N 6-cyclohexyl-4-(trifluoromethyl)-1H-pyridine-2-thione Chemical compound C1(CCCCC1)C1=CC(=CC(N1)=S)C(F)(F)F NWVHDMLGBYULFR-UHFFFAOYSA-N 0.000 claims description 4
- VUGUTRZRCUHAPS-UHFFFAOYSA-N 6-cyclohexyl-4-methyl-1H-pyridine-2-thione Chemical compound C1(CCCCC1)C1=CC(=CC(N1)=S)C VUGUTRZRCUHAPS-UHFFFAOYSA-N 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- 239000006207 intravenous dosage form Substances 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 239000006201 parenteral dosage form Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000002062 proliferating effect Effects 0.000 claims description 4
- 208000024891 symptom Diseases 0.000 claims description 4
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 4
- LYIACRHBYINAQO-UHFFFAOYSA-N 6-cyclopropyl-4-methyl-1H-pyridine-2-thione Chemical compound C1(CC1)C1=CC(=CC(N1)=S)C LYIACRHBYINAQO-UHFFFAOYSA-N 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 230000000626 neurodegenerative effect Effects 0.000 claims description 3
- 125000006546 (C4-C10) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- DYFBCVMPCWGVMV-UHFFFAOYSA-N 1,2-dihydropyridine-3-carbonitrile Chemical compound N#CC1=CC=CNC1 DYFBCVMPCWGVMV-UHFFFAOYSA-N 0.000 claims description 2
- NZFDZFJVWFDFQV-UHFFFAOYSA-N 2,4-bis(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=NC(C(F)(F)F)=C1 NZFDZFJVWFDFQV-UHFFFAOYSA-N 0.000 claims description 2
- ZVANSRULPRVUSG-UHFFFAOYSA-N 4,6-dimethyl-1h-pyridine-2-thione Chemical compound CC1=CC(C)=NC(S)=C1 ZVANSRULPRVUSG-UHFFFAOYSA-N 0.000 claims description 2
- ORVPLYYAPORELW-UHFFFAOYSA-N 6-(2-methylpropyl)-4-(trifluoromethyl)-1H-pyridine-2-thione Chemical compound C(C(C)C)C1=CC(=CC(N1)=S)C(F)(F)F ORVPLYYAPORELW-UHFFFAOYSA-N 0.000 claims description 2
- SGAXMCABIBTLJB-UHFFFAOYSA-N 6-butyl-4-(trifluoromethyl)-1H-pyridine-2-thione Chemical compound C(CCC)C1=CC(=CC(N1)=S)C(F)(F)F SGAXMCABIBTLJB-UHFFFAOYSA-N 0.000 claims description 2
- VESRNJYGBUDZHO-UHFFFAOYSA-N 6-cyclopropyl-4-(trifluoromethyl)-1H-pyridine-2-thione Chemical compound C1(CC1)C1=CC(=CC(N1)=S)C(F)(F)F VESRNJYGBUDZHO-UHFFFAOYSA-N 0.000 claims description 2
- KYYULPWLWVEAPB-UHFFFAOYSA-N 6-methyl-4-(trifluoromethyl)-1h-pyridine-2-thione Chemical compound CC1=CC(C(F)(F)F)=CC(=S)N1 KYYULPWLWVEAPB-UHFFFAOYSA-N 0.000 claims description 2
- LHYLYCNLYSWMTI-UHFFFAOYSA-N 6-methyl-4-propan-2-yl-1H-pyridine-2-thione Chemical compound C(C)(C)C1=CC(NC(=C1)C)=S LHYLYCNLYSWMTI-UHFFFAOYSA-N 0.000 claims description 2
- NHMKEIKRHFVEGN-UHFFFAOYSA-N 6-propan-2-yl-4-(trifluoromethyl)-1H-pyridine-2-thione Chemical compound C(C)(C)C1=CC(=CC(N1)=S)C(F)(F)F NHMKEIKRHFVEGN-UHFFFAOYSA-N 0.000 claims description 2
- 206010010254 Concussion Diseases 0.000 claims description 2
- 208000016192 Demyelinating disease Diseases 0.000 claims description 2
- 206010028570 Myelopathy Diseases 0.000 claims description 2
- 208000027418 Wounds and injury Diseases 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 206010008129 cerebral palsy Diseases 0.000 claims description 2
- 230000009514 concussion Effects 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 230000006378 damage Effects 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 208000014674 injury Diseases 0.000 claims description 2
- 208000037906 ischaemic injury Diseases 0.000 claims description 2
- 210000004698 lymphocyte Anatomy 0.000 claims description 2
- 230000002503 metabolic effect Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 208000002670 vitamin B12 deficiency Diseases 0.000 claims description 2
- 241001061127 Thione Species 0.000 claims 1
- 208000008795 neuromyelitis optica Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662337256P | 2016-05-16 | 2016-05-16 | |
| US62/337,256 | 2016-05-16 | ||
| PCT/US2017/032599 WO2017200902A1 (en) | 2016-05-16 | 2017-05-15 | Pyridinethiones, pharmaceutical compositions thereof, and their therapeutic use for treating a proliferative, inflammatory, neurodegenerative, or immune-mediated disease |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019515017A JP2019515017A (ja) | 2019-06-06 |
| JP2019515017A5 true JP2019515017A5 (https=) | 2020-07-02 |
| JP7044717B2 JP7044717B2 (ja) | 2022-03-30 |
Family
ID=58745507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018560167A Active JP7044717B2 (ja) | 2016-05-16 | 2017-05-15 | ピリジンチオン、その医薬組成物、及び増殖性疾患、炎症性疾患、神経変性疾患、又は免疫介在性疾患を治療するためのそれらの治療的使用 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US10233153B2 (https=) |
| EP (1) | EP3458440B1 (https=) |
| JP (1) | JP7044717B2 (https=) |
| CN (1) | CN109476600B (https=) |
| AU (2) | AU2017266878A1 (https=) |
| CA (1) | CA3024118A1 (https=) |
| DK (1) | DK3458440T3 (https=) |
| ES (1) | ES2928666T3 (https=) |
| TW (1) | TWI753910B (https=) |
| WO (1) | WO2017200902A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111303047B (zh) * | 2020-03-27 | 2023-04-25 | 上海阿拉丁生化科技股份有限公司 | 一种2-氨基-4,6-二甲基吡啶的合成方法 |
| CA3203975A1 (en) | 2020-12-03 | 2022-06-09 | Battelle Memorial Institute | Polymer nanoparticle and dna nanostructure compositions and methods for non-viral delivery |
| CA3216359A1 (en) | 2021-04-07 | 2022-10-13 | Battelle Memorial Institute | Rapid design, build, test, and learn technologies for identifying and using non-viral carriers |
| AU2024353375A1 (en) | 2023-09-29 | 2026-04-09 | Battelle Memorial Institute | Polymer nanoparticle compositions for in vivo expression of polypeptides |
| WO2025122954A1 (en) | 2023-12-08 | 2025-06-12 | Battelle Memorial Institute | Use of dna origami nanostructures for molecular information based data storage systems |
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-
2017
- 2017-05-12 TW TW106115889A patent/TWI753910B/zh active
- 2017-05-15 DK DK17725128.7T patent/DK3458440T3/da active
- 2017-05-15 EP EP17725128.7A patent/EP3458440B1/en active Active
- 2017-05-15 US US15/595,199 patent/US10233153B2/en active Active
- 2017-05-15 JP JP2018560167A patent/JP7044717B2/ja active Active
- 2017-05-15 CN CN201780043972.0A patent/CN109476600B/zh active Active
- 2017-05-15 WO PCT/US2017/032599 patent/WO2017200902A1/en not_active Ceased
- 2017-05-15 CA CA3024118A patent/CA3024118A1/en active Pending
- 2017-05-15 AU AU2017266878A patent/AU2017266878A1/en not_active Abandoned
- 2017-05-15 ES ES17725128T patent/ES2928666T3/es active Active
-
2019
- 2019-03-11 US US16/298,868 patent/US10654805B2/en active Active
-
2021
- 2021-10-13 AU AU2021250904A patent/AU2021250904B2/en active Active