JPWO2019178129A5 - - Google Patents
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- JPWO2019178129A5 JPWO2019178129A5 JP2020548735A JP2020548735A JPWO2019178129A5 JP WO2019178129 A5 JPWO2019178129 A5 JP WO2019178129A5 JP 2020548735 A JP2020548735 A JP 2020548735A JP 2020548735 A JP2020548735 A JP 2020548735A JP WO2019178129 A5 JPWO2019178129 A5 JP WO2019178129A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyridin
- carboxamide
- fluoroimidazole
- chloro
- 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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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 576
- -1 pyridin-1-yl Chemical group 0.000 claims description 411
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 322
- 229910052757 nitrogen Inorganic materials 0.000 claims description 164
- 229910052760 oxygen Inorganic materials 0.000 claims description 148
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 145
- 239000001301 oxygen Substances 0.000 claims description 145
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 143
- 125000005842 heteroatom Chemical group 0.000 claims description 143
- 229910052717 sulfur Inorganic materials 0.000 claims description 143
- 239000011593 sulfur Substances 0.000 claims description 143
- 229920006395 saturated elastomer Polymers 0.000 claims description 111
- 150000001875 compounds Chemical class 0.000 claims description 103
- 150000003839 salts Chemical class 0.000 claims description 62
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 56
- 125000001931 aliphatic group Chemical group 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 206010012688 Diabetic retinal oedema Diseases 0.000 claims description 3
- 206010019860 Hereditary angioedema Diseases 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 201000011190 diabetic macular edema Diseases 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 102000003827 Plasma Kallikrein Human genes 0.000 claims description 2
- 108090000113 Plasma Kallikrein Proteins 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 137
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 82
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 73
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 15
- 150000002460 imidazoles Chemical class 0.000 claims 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 5
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 4
- 235000019260 propionic acid Nutrition 0.000 claims 4
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 4
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 3
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 3
- NWVGXXPWOYZODV-UHFFFAOYSA-N 1h-imidazole-5-carbonitrile Chemical compound N#CC1=CN=CN1 NWVGXXPWOYZODV-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- LDDOSDVZPSGLFZ-UHFFFAOYSA-N ethyl cyclopropanecarboxylate Chemical compound CCOC(=O)C1CC1 LDDOSDVZPSGLFZ-UHFFFAOYSA-N 0.000 claims 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- FYCRNRZIEVLZDO-BYPYZUCNSA-N (2s)-morpholin-4-ium-2-carboxylate Chemical compound OC(=O)[C@@H]1CNCCO1 FYCRNRZIEVLZDO-BYPYZUCNSA-N 0.000 claims 1
- LKYNGTHMKCTTQC-UHFFFAOYSA-N 1,2-oxazole-3-carboxamide Chemical compound NC(=O)C=1C=CON=1 LKYNGTHMKCTTQC-UHFFFAOYSA-N 0.000 claims 1
- VAELWSLNTRVXQS-UHFFFAOYSA-N 1,3-oxazole-4-carboxamide Chemical compound NC(=O)C1=COC=N1 VAELWSLNTRVXQS-UHFFFAOYSA-N 0.000 claims 1
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 claims 1
- KEJFADGISRFLFO-UHFFFAOYSA-N 1H-indazol-6-amine Chemical compound NC1=CC=C2C=NNC2=C1 KEJFADGISRFLFO-UHFFFAOYSA-N 0.000 claims 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- LNFZAUNJFRYZLE-UHFFFAOYSA-N 2-fluoro-1h-imidazole Chemical compound FC1=NC=CN1 LNFZAUNJFRYZLE-UHFFFAOYSA-N 0.000 claims 1
- 125000000981 3-amino-3-oxopropyl group Chemical group [H]C([*])([H])C([H])([H])C(=O)N([H])[H] 0.000 claims 1
- FHZALEJIENDROK-UHFFFAOYSA-N 5-bromo-1h-imidazole Chemical compound BrC1=CN=CN1 FHZALEJIENDROK-UHFFFAOYSA-N 0.000 claims 1
- BNFGUBCFRVUHJH-UHFFFAOYSA-N 5-cyclopropyl-1h-imidazole Chemical compound C1CC1C1=CNC=N1 BNFGUBCFRVUHJH-UHFFFAOYSA-N 0.000 claims 1
- NJQHZENQKNIRSY-UHFFFAOYSA-N 5-ethyl-1h-imidazole Chemical compound CCC1=CNC=N1 NJQHZENQKNIRSY-UHFFFAOYSA-N 0.000 claims 1
- YXSUIVZFLAJASX-UHFFFAOYSA-N 5-methoxy-1h-imidazole Chemical compound COC1=CN=CN1 YXSUIVZFLAJASX-UHFFFAOYSA-N 0.000 claims 1
- HLGSNXCBXUQZEM-UHFFFAOYSA-N C1C(C1)C1=CC=C2N=CNC2=C1 Chemical compound C1C(C1)C1=CC=C2N=CNC2=C1 HLGSNXCBXUQZEM-UHFFFAOYSA-N 0.000 claims 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims 1
- MZDUQQVDGHZJQU-UHFFFAOYSA-N N-[(7-chloroimidazo[1,5-a]pyridin-1-yl)methyl]-1-[[6-cyclopropyl-8-(3-hydroxy-3-methylbutyl)imidazo[1,2-a]pyridin-2-yl]methyl]pyrazole-4-carboxamide Chemical compound ClC1=CC=2N(C=C1)C=NC=2CNC(=O)C=1C=NN(C=1)CC=1N=C2N(C=C(C=C2CCC(C)(C)O)C2CC2)C=1 MZDUQQVDGHZJQU-UHFFFAOYSA-N 0.000 claims 1
- UNWNQIIDASIOIA-UHFFFAOYSA-N N-[(7-chloroimidazo[1,5-a]pyridin-1-yl)methyl]-1-[[6-cyclopropyl-8-(3-hydroxyoxetan-3-yl)imidazo[1,2-a]pyridin-2-yl]methyl]triazole-4-carboxamide Chemical compound ClC1=CC=2N(C=C1)C=NC=2CNC(=O)C=1N=NN(C=1)CC=1N=C2N(C=C(C=C2C2(COC2)O)C2CC2)C=1 UNWNQIIDASIOIA-UHFFFAOYSA-N 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- GFZWHAAOIVMHOI-UHFFFAOYSA-N azetidine-3-carboxylic acid Chemical compound OC(=O)C1CNC1 GFZWHAAOIVMHOI-UHFFFAOYSA-N 0.000 claims 1
- MOLRJCRTZIEBKH-UHFFFAOYSA-N cyclopropane propanoic acid Chemical compound C(CC)(=O)O.C1CC1 MOLRJCRTZIEBKH-UHFFFAOYSA-N 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- QDYTUZCWBJRHKK-UHFFFAOYSA-N imidazole-4-methanol Chemical compound OCC1=CNC=N1 QDYTUZCWBJRHKK-UHFFFAOYSA-N 0.000 claims 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 claims 1
- 229940095102 methyl benzoate Drugs 0.000 claims 1
- 229940017219 methyl propionate Drugs 0.000 claims 1
- HFAWKTWWZYNOPU-UHFFFAOYSA-N n-methyl-1h-imidazol-5-amine Chemical compound CNC1=CN=CN1 HFAWKTWWZYNOPU-UHFFFAOYSA-N 0.000 claims 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- GGNIKGLUPSHSBV-UHFFFAOYSA-N thiazole-5-carboxamide Chemical compound NC(=O)C1=CN=CS1 GGNIKGLUPSHSBV-UHFFFAOYSA-N 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 238000000034 method Methods 0.000 description 3
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023200830A JP2024012697A (ja) | 2018-03-13 | 2023-11-28 | 血漿カリクレインのインヒビターとしての置換されたイミダゾピリジン及びその使用 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862642376P | 2018-03-13 | 2018-03-13 | |
| US62/642,376 | 2018-03-13 | ||
| US201862757728P | 2018-11-08 | 2018-11-08 | |
| US62/757,728 | 2018-11-08 | ||
| PCT/US2019/021897 WO2019178129A1 (en) | 2018-03-13 | 2019-03-12 | Substituted imidazopyridines as inhibitors of plasma kallikrein and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023200830A Division JP2024012697A (ja) | 2018-03-13 | 2023-11-28 | 血漿カリクレインのインヒビターとしての置換されたイミダゾピリジン及びその使用 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2021517893A JP2021517893A (ja) | 2021-07-29 |
| JPWO2019178129A5 true JPWO2019178129A5 (https=) | 2022-03-22 |
| JP2021517893A5 JP2021517893A5 (https=) | 2022-03-22 |
| JP7590183B2 JP7590183B2 (ja) | 2024-11-26 |
Family
ID=65904618
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020548735A Active JP7590183B2 (ja) | 2018-03-13 | 2019-03-12 | 血漿カリクレインのインヒビターとしての置換されたイミダゾピリジン及びその使用 |
| JP2023200830A Withdrawn JP2024012697A (ja) | 2018-03-13 | 2023-11-28 | 血漿カリクレインのインヒビターとしての置換されたイミダゾピリジン及びその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023200830A Withdrawn JP2024012697A (ja) | 2018-03-13 | 2023-11-28 | 血漿カリクレインのインヒビターとしての置換されたイミダゾピリジン及びその使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US10730874B2 (https=) |
| EP (1) | EP3765459A1 (https=) |
| JP (2) | JP7590183B2 (https=) |
| KR (1) | KR20200143376A (https=) |
| CN (1) | CN112135825A (https=) |
| AU (1) | AU2019234670B2 (https=) |
| CA (1) | CA3093802A1 (https=) |
| TW (1) | TWI834641B (https=) |
| WO (1) | WO2019178129A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7210540B2 (ja) | 2017-08-04 | 2023-01-23 | 武田薬品工業株式会社 | 血漿カリクレインの阻害剤およびその使用 |
| KR20200143376A (ko) * | 2018-03-13 | 2020-12-23 | 샤이어 휴먼 지네틱 테라피즈 인크. | 혈장 칼리크레인 억제제로서의 치환된 이미다조피리딘 및 이의 용도 |
| TW202045011A (zh) * | 2019-02-28 | 2020-12-16 | 瑞士商先正達農作物保護公司 | 具有含硫取代基之殺有害生物活性雜環衍生物 |
| WO2020204112A1 (ja) | 2019-04-01 | 2020-10-08 | 日産化学株式会社 | ピリダジノン化合物及び除草剤 |
| CN114667289B (zh) * | 2019-09-18 | 2025-08-26 | 武田药品工业有限公司 | 杂芳基血浆激肽释放酶抑制剂 |
| EP4031547B1 (en) * | 2019-09-18 | 2024-07-17 | Takeda Pharmaceutical Company Limited | Plasma kallikrein inhibitors and uses thereof |
| WO2021211938A1 (en) | 2020-04-17 | 2021-10-21 | Shire Human Genetic Therapies, Inc. | Solid forms of inhibitors of plasma kallikrein |
| PT4136091T (pt) | 2020-04-17 | 2025-08-22 | Takeda Pharmaceuticals Co | Formas e composições de inibidores da calicreína plasmática |
| EP4223755A4 (en) | 2020-09-30 | 2025-05-14 | Sumitomo Chemical Company, Limited | Heterocyclic compound and composition containing it for controlling harmful arthropods |
| BR112023018619A2 (pt) | 2021-03-17 | 2023-11-28 | Takeda Pharmaceuticals Co | Inibidores de heteroaril de calicreína plasmática |
| US20240382482A1 (en) * | 2021-03-17 | 2024-11-21 | Takeda Pharmaceutical Company Limited | Plasma kallikrein inhibitors |
| US20240226106A1 (en) * | 2021-03-17 | 2024-07-11 | Shire Human Genetic Therapies, Inc. | Inhibitors of plasma kallikrein |
| EP4308564A1 (en) | 2021-03-17 | 2024-01-24 | Takeda Pharmaceutical Company Limited | Polycyclic inhibitors of plasma kallikrein |
| CN117396473A (zh) * | 2021-03-17 | 2024-01-12 | 武田药品工业株式会社 | 血浆激肽释放酶的咪唑并吡啶基抑制剂 |
| JP2025531207A (ja) | 2022-09-15 | 2025-09-19 | 武田薬品工業株式会社 | 遺伝性血管性浮腫の処置のための血漿カリクレイン阻害剤としてのｎ－（（イソキノリン－６イル）メチル）－１ｈ－ピラゾール－４－カルボキサミド誘導体 |
| CR20250520A (es) * | 2023-05-09 | 2025-12-19 | Amgen Inc | Alcoholes y éteres bicíclicos 5,6-condensados y 6,6-condensados y composiciones para su uso como moduladores de la 15-prostaglandina deshidrogenasa |
| CN119708015A (zh) * | 2023-09-28 | 2025-03-28 | 杭州圣域生物医药科技有限公司 | 杂芳基化合物、其中间体、制备方法和应用 |
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-
2019
- 2019-03-12 KR KR1020207029051A patent/KR20200143376A/ko active Pending
- 2019-03-12 WO PCT/US2019/021897 patent/WO2019178129A1/en not_active Ceased
- 2019-03-12 CN CN201980032031.6A patent/CN112135825A/zh active Pending
- 2019-03-12 CA CA3093802A patent/CA3093802A1/en active Pending
- 2019-03-12 AU AU2019234670A patent/AU2019234670B2/en active Active
- 2019-03-12 US US16/299,996 patent/US10730874B2/en active Active
- 2019-03-12 EP EP19713331.7A patent/EP3765459A1/en active Pending
- 2019-03-12 JP JP2020548735A patent/JP7590183B2/ja active Active
- 2019-03-13 TW TW108108497A patent/TWI834641B/zh active
-
2020
- 2020-06-22 US US16/908,497 patent/US11352356B2/en active Active
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2022
- 2022-04-20 US US17/724,753 patent/US12441724B2/en active Active
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2023
- 2023-11-28 JP JP2023200830A patent/JP2024012697A/ja not_active Withdrawn
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