JP2020510046A5 - - Google Patents
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- Publication number
- JP2020510046A5 JP2020510046A5 JP2019549462A JP2019549462A JP2020510046A5 JP 2020510046 A5 JP2020510046 A5 JP 2020510046A5 JP 2019549462 A JP2019549462 A JP 2019549462A JP 2019549462 A JP2019549462 A JP 2019549462A JP 2020510046 A5 JP2020510046 A5 JP 2020510046A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- quinoline
- imidazole
- chloro
- pyran
- 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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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 154
- -1 2,2-difluoropropyl Chemical group 0.000 claims 97
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 45
- 150000001875 compounds Chemical class 0.000 claims 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 36
- 150000003839 salts Chemical class 0.000 claims 35
- 102100021468 Equilibrative nucleoside transporter 2 Human genes 0.000 claims 32
- 101000822017 Homo sapiens Equilibrative nucleoside transporter 2 Proteins 0.000 claims 32
- 102100021469 Equilibrative nucleoside transporter 1 Human genes 0.000 claims 31
- 101000822020 Homo sapiens Equilibrative nucleoside transporter 1 Proteins 0.000 claims 31
- CIIFKVFOVFJZDM-UHFFFAOYSA-N quinoline-8-carbonitrile Chemical compound C1=CN=C2C(C#N)=CC=CC2=C1 CIIFKVFOVFJZDM-UHFFFAOYSA-N 0.000 claims 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 24
- 125000004429 atom Chemical group 0.000 claims 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- FVNAQFOFKZUYGE-UHFFFAOYSA-N 1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-8-fluoro-2-[(4-methyltriazol-1-yl)methyl]imidazo[4,5-c]quinoline Chemical compound FC1(C(CN(C1)C)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)F)CN1N=NC(=C1)C)F FVNAQFOFKZUYGE-UHFFFAOYSA-N 0.000 claims 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims 3
- YDUTZRUUPJSWMS-KRWDZBQOSA-N 3-[[8-chloro-1-[(4S)-3,3-difluorooxan-4-yl]imidazo[4,5-c]quinolin-2-yl]methyl]-5-methyl-1,2-oxazole Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@@H]1C(COCC1)(F)F)CC1=NOC(=C1)C YDUTZRUUPJSWMS-KRWDZBQOSA-N 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- YVFMOFCDPODUPW-UHFFFAOYSA-N 3-[[8-chloro-1-(4,4-difluoro-1-methylpyrrolidin-3-yl)imidazo[4,5-c]quinolin-2-yl]methyl]-5-methyl-1,2,4-oxadiazole Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1CN(CC1(F)F)C)CC1=NOC(=N1)C YVFMOFCDPODUPW-UHFFFAOYSA-N 0.000 claims 2
- DTYXHKYEGPKZBD-UHFFFAOYSA-N 8-chloro-1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-2-[(4-methyltriazol-1-yl)methyl]imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1CN(CC1(F)F)C)CN1N=NC(=C1)C DTYXHKYEGPKZBD-UHFFFAOYSA-N 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- PYFVAVZYKLONHU-TZMCWYRMSA-N 1-[(2R,4R)-2-methyloxan-4-yl]-2-(1,2,4-triazol-1-ylmethyl)-8-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C[C@H]1OCC[C@H](C1)N1C(=NC=2C=NC=3C=CC(=CC3C21)C(F)(F)F)CN2N=CN=C2 PYFVAVZYKLONHU-TZMCWYRMSA-N 0.000 claims 1
- GKZSTPTXOXPTCF-UHFFFAOYSA-N 3-[[8-chloro-1-(3,3-difluorooxan-4-yl)imidazo[4,5-c]quinolin-2-yl]methyl]-5-methyl-1,2,4-oxadiazole Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1C(COCC1)(F)F)CC1=NOC(=N1)C GKZSTPTXOXPTCF-UHFFFAOYSA-N 0.000 claims 1
- NHIUYAPDFWHHHY-UKRRQHHQSA-N 8-(difluoromethyl)-2-[(4-methoxypyrazol-1-yl)methyl]-1-[(2R,4R)-2-methyloxan-4-yl]imidazo[4,5-c]quinoline Chemical compound FC(C1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@H]1C[C@H](OCC1)C)CN1N=CC(=C1)OC)F NHIUYAPDFWHHHY-UKRRQHHQSA-N 0.000 claims 1
- ILDKLXJMIUPRLE-UHFFFAOYSA-N 8-chloro-1-(3,3-difluorooxan-4-yl)-2-[(4-methyltriazol-1-yl)methyl]imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1C(COCC1)(F)F)CN1N=NC(=C1)C ILDKLXJMIUPRLE-UHFFFAOYSA-N 0.000 claims 1
- PURUAKUDDOJBAN-UHFFFAOYSA-N 8-chloro-1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-2-[(1-methyl-1,2,4-triazol-3-yl)methyl]imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1CN(CC1(F)F)C)CC1=NN(C=N1)C PURUAKUDDOJBAN-UHFFFAOYSA-N 0.000 claims 1
- LYOWXMJQTPATSP-UHFFFAOYSA-N 8-chloro-1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-2-[(4-methyltriazol-2-yl)methyl]imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1CN(CC1(F)F)C)CN1N=CC(=N1)C LYOWXMJQTPATSP-UHFFFAOYSA-N 0.000 claims 1
- AFSJECQGCYZDGF-UHFFFAOYSA-N 8-chloro-2-[(4-cyclopropyltriazol-1-yl)methyl]-1-(3,3-difluorooxan-4-yl)imidazo[4,5-c]quinoline Chemical compound C1(=CC=C2N=CC3=C(N(C(=N3)CN3C=C(N=N3)C3CC3)C3CCOCC3(F)F)C2=C1)Cl AFSJECQGCYZDGF-UHFFFAOYSA-N 0.000 claims 1
- JMVLVNHZMPXEMD-UHFFFAOYSA-N 8-chloro-2-[(4-cyclopropyltriazol-1-yl)methyl]-1-(4,4-difluoro-1-methylpyrrolidin-3-yl)imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1CN(CC1(F)F)C)CN1N=NC(=C1)C1CC1 JMVLVNHZMPXEMD-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
- 206010024229 Leprosy Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000034799 Tauopathies Diseases 0.000 claims 1
- 230000001054 cortical effect Effects 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762469756P | 2017-03-10 | 2017-03-10 | |
| US62/469,756 | 2017-03-10 | ||
| US201862629152P | 2018-02-12 | 2018-02-12 | |
| US62/629,152 | 2018-02-12 | ||
| PCT/IB2018/051439 WO2018163066A1 (en) | 2017-03-10 | 2018-03-06 | Novel imidazo[4,5-c]quinoline derivatives as lrrk2 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020510046A JP2020510046A (ja) | 2020-04-02 |
| JP2020510046A5 true JP2020510046A5 (https=) | 2021-04-22 |
| JP7219223B2 JP7219223B2 (ja) | 2023-02-07 |
Family
ID=61683855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019549462A Active JP7219223B2 (ja) | 2017-03-10 | 2018-03-06 | ＬＲＲＫ２阻害剤としての新規のイミダゾ［４，５－ｃ］キノリン誘導体 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US11312713B2 (https=) |
| EP (1) | EP3592741B1 (https=) |
| JP (1) | JP7219223B2 (https=) |
| KR (1) | KR102582626B1 (https=) |
| CN (1) | CN111051304B (https=) |
| AU (1) | AU2018230236B2 (https=) |
| BR (1) | BR112019018688A2 (https=) |
| CA (1) | CA3056030A1 (https=) |
| IL (1) | IL269214B (https=) |
| MX (1) | MX2019010756A (https=) |
| SG (2) | SG11201908322WA (https=) |
| TW (1) | TWI701246B (https=) |
| WO (1) | WO2018163066A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112022022511A2 (pt) | 2020-05-06 | 2022-12-13 | Servier Lab | Inibidores macrocíclicos de lrrk2 quinase |
| EP4236950A4 (en) | 2020-10-29 | 2024-10-23 | Merck Sharp & Dohme LLC | N-LINKED ISOQUINOLINE AMIDES AS LRRK2 INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF |
| BR112023017834A2 (pt) | 2021-03-18 | 2023-10-03 | Servier Lab | Inibidores de lrrk2 cinase macrocíclicos |
| WO2023220238A1 (en) * | 2022-05-12 | 2023-11-16 | Interline Therapeutics, Inc. | Lrrk2 inhibitors |
| CN119403801A (zh) * | 2022-05-12 | 2025-02-07 | 因特来治疗公司 | Lrrk2抑制剂 |
| CN115728413A (zh) * | 2022-11-09 | 2023-03-03 | 内蒙古帕默康创医疗仪器有限公司 | 舍曲林血药浓度的定量分析方法 |
| CN116879450A (zh) * | 2023-07-25 | 2023-10-13 | 江苏汉邦科技股份有限公司 | 一种利用超临界流体色谱系统分离纯化芦可替尼前体的方法 |
| CN118440041B (zh) * | 2024-07-02 | 2024-09-27 | 苏州凯瑞医药科技有限公司 | 一种手性4-氨基-3-羟基四氢吡喃的制备方法 |
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| RU2722149C1 (ru) * | 2015-09-14 | 2020-05-27 | Пфайзер Инк. | Новые производные имидазо[4,5-c] хинолинов и имидазо[4,5-c][1,5] нафтиридинов в качестве ингибиторов LRRK2 |
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-
2018
- 2018-03-06 AU AU2018230236A patent/AU2018230236B2/en active Active
- 2018-03-06 CA CA3056030A patent/CA3056030A1/en active Pending
- 2018-03-06 US US16/492,558 patent/US11312713B2/en active Active
- 2018-03-06 WO PCT/IB2018/051439 patent/WO2018163066A1/en not_active Ceased
- 2018-03-06 KR KR1020197029735A patent/KR102582626B1/ko active Active
- 2018-03-06 CN CN201880029989.5A patent/CN111051304B/zh active Active
- 2018-03-06 EP EP18711703.1A patent/EP3592741B1/en active Active
- 2018-03-06 SG SG11201908322W patent/SG11201908322WA/en unknown
- 2018-03-06 MX MX2019010756A patent/MX2019010756A/es unknown
- 2018-03-06 JP JP2019549462A patent/JP7219223B2/ja active Active
- 2018-03-06 BR BR112019018688A patent/BR112019018688A2/pt not_active Application Discontinuation
- 2018-03-06 SG SG10202110112T patent/SG10202110112TA/en unknown
- 2018-03-07 TW TW107107734A patent/TWI701246B/zh active
-
2019
- 2019-09-09 IL IL269214A patent/IL269214B/en unknown
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