JPWO2020047312A5 - - Google Patents
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- Publication number
- JPWO2020047312A5 JPWO2020047312A5 JP2021510446A JP2021510446A JPWO2020047312A5 JP WO2020047312 A5 JPWO2020047312 A5 JP WO2020047312A5 JP 2021510446 A JP2021510446 A JP 2021510446A JP 2021510446 A JP2021510446 A JP 2021510446A JP WO2020047312 A5 JPWO2020047312 A5 JP WO2020047312A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- optionally substituted
- sulfonamide
- amino
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 160
- 239000001257 hydrogen Substances 0.000 claims description 158
- 229910052739 hydrogen Inorganic materials 0.000 claims description 158
- 150000001875 compounds Chemical class 0.000 claims description 132
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 116
- -1 methyl ((S) -1-((R) -1-phenylethyl) pyrrolidine-3-yl) amino Chemical group 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 50
- 229940002612 prodrug Drugs 0.000 claims description 45
- 239000000651 prodrug Substances 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 45
- 125000001188 haloalkyl group Chemical group 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 42
- 239000012453 solvate Substances 0.000 claims description 41
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 38
- 125000001475 halogen functional group Chemical group 0.000 claims description 34
- 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 30
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 20
- 125000003107 substituted aryl group Chemical group 0.000 claims description 18
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 16
- 125000000335 thiazolyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 108010052164 Sodium Channels Proteins 0.000 claims description 12
- 102000018674 Sodium Channels Human genes 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 7
- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 6
- MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- NKFLEFWUYAUDJV-UHFFFAOYSA-N pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1 NKFLEFWUYAUDJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 206010010904 Convulsion Diseases 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 208000028329 epileptic seizure Diseases 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims description 2
- RSAVKVUPOAKTAP-KRWDZBQOSA-N 3-fluoro-5-[[(3S)-1-[(2-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound FC=1C(=NC=C(C=1C)N(C)[C@@H]1CN(CC1)CC1=C(C=CC=C1)F)S(=O)(=O)NC1=NC(=CC=C1)F RSAVKVUPOAKTAP-KRWDZBQOSA-N 0.000 claims description 2
- OVYARDCMVLNIME-UHFFFAOYSA-N 3-fluoro-5-[[1-[(2-fluorophenyl)methyl]piperidin-4-yl]-methylamino]-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound FC=1C(=NC=C(C=1C)N(C)C1CCN(CC1)CC1=C(C=CC=C1)F)S(=O)(=O)NC1=NC(=CC=C1)F OVYARDCMVLNIME-UHFFFAOYSA-N 0.000 claims description 2
- YIKJNPKJBVVXED-UHFFFAOYSA-N 4-[(1-benzylpiperidin-4-yl)-methylamino]-N-(6-fluoropyridin-2-yl)-5-methylthiophene-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C=1C=C(SC=1C)S(=O)(=O)NC1=NC(=CC=C1)F)C YIKJNPKJBVVXED-UHFFFAOYSA-N 0.000 claims description 2
- QUHULGIHZLHSEE-UHFFFAOYSA-N 5-[(1-benzylpiperidin-4-yl)-methylamino]-3-fluoro-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C=1C(=C(C(=NC=1)S(=O)(=O)NC1=NC(=CC=C1)F)F)C)C QUHULGIHZLHSEE-UHFFFAOYSA-N 0.000 claims description 2
- FFYXKCTYHJPFJU-UHFFFAOYSA-N 5-[(1-benzylpiperidin-4-yl)-methylamino]-3-fluoro-N-(6-fluoropyridin-2-yl)-6-methylpyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C=1C=C(C(=NC=1C)S(=O)(=O)NC1=NC(=CC=C1)F)F)C FFYXKCTYHJPFJU-UHFFFAOYSA-N 0.000 claims description 2
- AMQJFTMGKNIINO-UHFFFAOYSA-N 5-[(1-benzylpiperidin-4-yl)-methylamino]-N-(6-fluoropyridin-2-yl)-4-methyl-1,3-thiazole-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C1=C(N=C(S1)S(=O)(=O)NC1=NC(=CC=C1)F)C)C AMQJFTMGKNIINO-UHFFFAOYSA-N 0.000 claims description 2
- RLTVQPTYWXWWPV-SFHVURJKSA-N 5-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-3-fluoro-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C=1C(=C(C(=NC=1)S(=O)(=O)NC1=NC(=CC=C1)F)F)C)C RLTVQPTYWXWWPV-SFHVURJKSA-N 0.000 claims description 2
- ODGXYSJPMZSCEK-SFHVURJKSA-N 5-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-4-methyl-N-(1,2-thiazol-3-yl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C=1C(=CC(=NC=1)S(=O)(=O)NC1=NSC=C1)C)C ODGXYSJPMZSCEK-SFHVURJKSA-N 0.000 claims description 2
- QQWICYYXCHMGMZ-IBGZPJMESA-N 5-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C=1C(=CC(=NC=1)S(=O)(=O)NC1=NC(=CC=C1)F)C)C QQWICYYXCHMGMZ-IBGZPJMESA-N 0.000 claims description 2
- XCVXMOSTQLIATQ-MRXNPFEDSA-N 5-[[1-[(1R)-1-(2-fluorophenyl)ethyl]piperidin-4-yl]-methylamino]-N-(6-fluoropyridin-2-yl)-4-methyl-1,3-thiazole-2-sulfonamide Chemical compound FC1=C(C=CC=C1)[C@@H](C)N1CCC(CC1)N(C1=C(N=C(S1)S(=O)(=O)NC1=NC(=CC=C1)F)C)C XCVXMOSTQLIATQ-MRXNPFEDSA-N 0.000 claims description 2
- WGDILJNGFXFIAY-UHFFFAOYSA-N 5-[[1-[(2-fluorophenyl)methyl]piperidin-4-yl]-methylamino]-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound FC1=C(CN2CCC(CC2)N(C=2C(=CC(=NC=2)S(=O)(=O)NC2=NC(=CC=C2)F)C)C)C=CC=C1 WGDILJNGFXFIAY-UHFFFAOYSA-N 0.000 claims description 2
- GOPCJWYLPSWJCM-UHFFFAOYSA-N 5-[[1-[(3-fluorophenyl)methyl]piperidin-4-yl]-methylamino]-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound FC=1C=C(CN2CCC(CC2)N(C=2C(=CC(=NC=2)S(=O)(=O)NC2=NC(=CC=C2)F)C)C)C=CC=1 GOPCJWYLPSWJCM-UHFFFAOYSA-N 0.000 claims description 2
- ZPVFMBCRLJXBIX-KRWDZBQOSA-N CC(C(N(C)[C@@H]1CN(CC2=NC(C3CC3)=CS2)CC1)=C1)=CCN1C1=CSC=N1 Chemical compound CC(C(N(C)[C@@H]1CN(CC2=NC(C3CC3)=CS2)CC1)=C1)=CCN1C1=CSC=N1 ZPVFMBCRLJXBIX-KRWDZBQOSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 210000004027 cell Anatomy 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 210000004962 mammalian cell Anatomy 0.000 claims description 2
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 2
- LOEIOUFEFDPFQL-UHFFFAOYSA-N 5-(1-benzylpiperidin-4-yl)oxy-N-(6-fluoropyridin-2-yl)-4-(trifluoromethyl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)OC=1C(=CC(=NC=1)S(=O)(=O)NC1=NC(=CC=C1)F)C(F)(F)F LOEIOUFEFDPFQL-UHFFFAOYSA-N 0.000 description 1
- HVHOCAKRYXUBFR-UHFFFAOYSA-N 5-(1-benzylpiperidin-4-yl)oxy-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)OC=1C(=CC(=NC=1)S(=O)(=O)NC1=NC(=CC=C1)F)C HVHOCAKRYXUBFR-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862725960P | 2018-08-31 | 2018-08-31 | |
| US62/725,960 | 2018-08-31 | ||
| PCT/US2019/048900 WO2020047312A1 (en) | 2018-08-31 | 2019-08-29 | Heteroaryl-substituted sulfonamide compounds and their use as sodium channel inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021535137A JP2021535137A (ja) | 2021-12-16 |
| JPWO2020047312A5 true JPWO2020047312A5 (hu) | 2022-07-20 |
| JP7383012B2 JP7383012B2 (ja) | 2023-11-17 |
Family
ID=67953871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021510446A Active JP7383012B2 (ja) | 2018-08-31 | 2019-08-29 | ヘテロアリール置換スルホンアミド化合物、およびナトリウムチャネル阻害剤としてのその使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10752623B2 (hu) |
| EP (1) | EP3844158A1 (hu) |
| JP (1) | JP7383012B2 (hu) |
| CN (1) | CN112638898B (hu) |
| CA (1) | CA3104913A1 (hu) |
| MA (1) | MA53488A (hu) |
| WO (1) | WO2020047312A1 (hu) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109526219B (zh) | 2016-05-20 | 2021-03-12 | 泽农医药公司 | 苯磺酰胺及其作为治疗剂的用途 |
| BR112019011121A2 (pt) | 2016-12-09 | 2019-10-01 | Xenon Pharmaceuticals Inc | compostos de benzenossulfonamida e seu uso como agentes terapêuticos |
| CN112262142B (zh) | 2018-06-13 | 2023-11-14 | 泽农医药公司 | 苯磺酰胺化合物及其作为治疗剂的用途 |
| CR20210099A (es) | 2018-08-31 | 2021-06-24 | Xenon Pharmaceuticals Inc | Compuestos de sulfonamida sustituidos con heteroarilo y su uso como agentes terapèuticos |
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| CN106795149B (zh) | 2015-05-05 | 2019-09-24 | 上海海雁医药科技有限公司 | 双环取代的苯磺酰胺衍生物、其制法与医药上的用途 |
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| CN109526219B (zh) * | 2016-05-20 | 2021-03-12 | 泽农医药公司 | 苯磺酰胺及其作为治疗剂的用途 |
| US10668067B2 (en) * | 2016-07-20 | 2020-06-02 | Amgen Inc. | Pyridine sulfonamides |
| TW201811766A (zh) * | 2016-08-29 | 2018-04-01 | 瑞士商諾華公司 | N-(吡啶-2-基)吡啶-磺醯胺衍生物及其用於疾病治療之用途 |
| US10968210B2 (en) | 2016-11-17 | 2021-04-06 | Merck Sharp & Dohme Corp. | Diamino-alkylamino-linked arylsulfonamide compounds with selective activity in voltage-gated sodium channels |
| BR112019011121A2 (pt) | 2016-12-09 | 2019-10-01 | Xenon Pharmaceuticals Inc | compostos de benzenossulfonamida e seu uso como agentes terapêuticos |
| PE20211065A1 (es) * | 2018-07-27 | 2021-06-09 | Xenon Pharmaceuticals Inc | Metodo para tratar la epilepsia |
-
2019
- 2019-08-29 US US16/555,983 patent/US10752623B2/en active Active
- 2019-08-29 WO PCT/US2019/048900 patent/WO2020047312A1/en unknown
- 2019-08-29 EP EP19768958.1A patent/EP3844158A1/en active Pending
- 2019-08-29 CN CN201980056968.7A patent/CN112638898B/zh active Active
- 2019-08-29 JP JP2021510446A patent/JP7383012B2/ja active Active
- 2019-08-29 MA MA053488A patent/MA53488A/fr unknown
- 2019-08-29 CA CA3104913A patent/CA3104913A1/en active Pending
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