JP2020515546A5 - - Google Patents
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- Publication number
- JP2020515546A5 JP2020515546A5 JP2019552594A JP2019552594A JP2020515546A5 JP 2020515546 A5 JP2020515546 A5 JP 2020515546A5 JP 2019552594 A JP2019552594 A JP 2019552594A JP 2019552594 A JP2019552594 A JP 2019552594A JP 2020515546 A5 JP2020515546 A5 JP 2020515546A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- compound
- chlorophenyl
- hydroxy
- 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 79
- 150000001875 compounds Chemical class 0.000 claims 52
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 40
- 238000004519 manufacturing process Methods 0.000 claims 25
- RMCVDTXCEAJNTG-UHFFFAOYSA-N 1-methoxy-2,3-dihydro-1h-isoindole Chemical compound C1=CC=C2C(OC)NCC2=C1 RMCVDTXCEAJNTG-UHFFFAOYSA-N 0.000 claims 23
- 238000000034 method Methods 0.000 claims 22
- 239000012022 methylating agents Substances 0.000 claims 21
- -1 hydroxy, hydroxy Chemical group 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 239000012453 solvate Substances 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000001188 haloalkyl group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 claims 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims 6
- GJFNRSDCSTVPCJ-UHFFFAOYSA-N 1,8-bis(dimethylamino)naphthalene Chemical compound C1=CC(N(C)C)=C2C(N(C)C)=CC=CC2=C1 GJFNRSDCSTVPCJ-UHFFFAOYSA-N 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 5
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 4
- 150000001299 aldehydes Chemical class 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 239000000010 aprotic solvent Substances 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical group [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims 4
- ANYSGBYRTLOUPO-UHFFFAOYSA-N lithium tetramethylpiperidide Chemical compound [Li]N1C(C)(C)CCCC1(C)C ANYSGBYRTLOUPO-UHFFFAOYSA-N 0.000 claims 4
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims 4
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 claims 4
- 150000002825 nitriles Chemical class 0.000 claims 4
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- BXVSAYBZSGIURM-UHFFFAOYSA-N 2-phenoxy-4h-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide Chemical compound O1CC2=CC=CC=C2OP1(=O)OC1=CC=CC=C1 BXVSAYBZSGIURM-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000002466 imines Chemical class 0.000 claims 3
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 claims 3
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 3
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 238000007257 deesterification reaction Methods 0.000 claims 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 238000010348 incorporation Methods 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical group OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 2
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 claims 1
- JDCHPEZNOKLHPK-WAURZEPHSA-N (2S,3S)-3-(4-chlorophenyl)-3-[1-(4-chlorophenyl)-7-fluoro-5-[(1S)-1-hydroxy-1-(oxan-4-yl)propyl]-1-methoxy-3-oxoisoindol-2-yl]-2-methylpropanoic acid Chemical compound ClC1=CC=C(C=C1)[C@H]([C@@H](C(=O)O)C)N1C(C2=C(C=C(C=C2C1=O)[C@](CC)(C1CCOCC1)O)F)(OC)C1=CC=C(C=C1)Cl JDCHPEZNOKLHPK-WAURZEPHSA-N 0.000 claims 1
- UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 claims 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- 238000007792 addition Methods 0.000 claims 1
- 238000005575 aldol reaction Methods 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000037406 food intake Effects 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 238000004808 supercritical fluid chromatography Methods 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- VLRPSULJZLWLPQ-UHFFFAOYSA-N CCC(C1CCOCC1)(c1cc(F)c(C(c(cc2)ccc2Cl)=O)c(C(O)=O)c1)O Chemical compound CCC(C1CCOCC1)(c1cc(F)c(C(c(cc2)ccc2Cl)=O)c(C(O)=O)c1)O VLRPSULJZLWLPQ-UHFFFAOYSA-N 0.000 description 1
- VLRPSULJZLWLPQ-QFIPXVFZSA-N CC[C@](C1CCOCC1)(c1cc(F)c(C(c(cc2)ccc2Cl)=O)c(C(O)=O)c1)O Chemical compound CC[C@](C1CCOCC1)(c1cc(F)c(C(c(cc2)ccc2Cl)=O)c(C(O)=O)c1)O VLRPSULJZLWLPQ-QFIPXVFZSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1704965.1A GB201704965D0 (en) | 2017-03-28 | 2017-03-28 | Pharmaceutical compounds |
| GB1704965.1 | 2017-03-28 | ||
| PCT/GB2018/050845 WO2018178691A1 (en) | 2017-03-28 | 2018-03-28 | Isoindolinone inhibitors of the mdm2-p53 interaction and process for making them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020515546A JP2020515546A (ja) | 2020-05-28 |
| JP2020515546A5 true JP2020515546A5 (enExample) | 2021-05-13 |
| JP7495790B2 JP7495790B2 (ja) | 2024-06-05 |
Family
ID=58687834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019552594A Active JP7495790B2 (ja) | 2017-03-28 | 2018-03-28 | Ｍｄｍ２－ｐ５３相互作用のイソインドリノン阻害剤およびそれを作製するためのプロセス |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US11603367B2 (enExample) |
| EP (1) | EP3601272A1 (enExample) |
| JP (1) | JP7495790B2 (enExample) |
| KR (1) | KR102673967B1 (enExample) |
| CN (1) | CN110678462B (enExample) |
| GB (1) | GB201704965D0 (enExample) |
| WO (1) | WO2018178691A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201517217D0 (en) | 2015-09-29 | 2015-11-11 | Astex Therapeutics Ltd And Cancer Res Technology Ltd | Pharmaceutical compounds |
| GB201704966D0 (en) | 2017-03-28 | 2017-05-10 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| GB201704965D0 (en) * | 2017-03-28 | 2017-05-10 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| CN113453678A (zh) * | 2018-11-26 | 2021-09-28 | 德彪药业国际股份公司 | Hiv感染的联合治疗 |
| CN109897069B (zh) * | 2019-02-12 | 2021-08-20 | 华东师范大学 | 一种3，3-二取代吲哚啉酮及其衍生物及其合成方法和应用 |
| CN110845288B (zh) * | 2019-11-28 | 2022-07-19 | 浙江工业大学 | 一种手性β-氨基醛类化合物的不对称合成方法 |
| GB201919219D0 (en) | 2019-12-23 | 2020-02-05 | Otsuka Pharma Co Ltd | Cancer biomarkers |
| CN111057128B (zh) * | 2019-12-25 | 2023-05-16 | 哈尔滨师范大学 | 一种含硫的异吲哚酮并环肽衍生物及其制备方法 |
| US20230313313A1 (en) | 2020-08-27 | 2023-10-05 | Otsuka Pharmaceutical Co., Ltd. | Biomarkers for cancer therapy using mdm2 antagonists |
| GB202103080D0 (en) | 2021-03-04 | 2021-04-21 | Otsuka Pharma Co Ltd | Cancer biomarkers |
| WO2025104679A1 (en) * | 2023-11-16 | 2025-05-22 | Otsuka Pharmaceutical Co., Ltd. | Processes for making intermediates for isoindolinone inhibitors of the mdm2-p53 interaction having anticancer activity |
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| KR101401705B1 (ko) | 2012-01-31 | 2014-06-27 | 울산대학교 산학협력단 | 로듐 촉매를 이용한 이소인돌린 유도체의 합성방법 |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US20150258068A1 (en) | 2012-10-30 | 2015-09-17 | Mei Pharma, Inc. | Combination therapies |
| EP3563836A1 (en) | 2013-03-01 | 2019-11-06 | Astex Pharmaceuticals, Inc. | Drug combinations |
| JP6461126B2 (ja) | 2013-07-03 | 2019-01-30 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | Ｍｄｍ２アンタゴニストを用いた患者のがん治療法をパーソナライズするためのｍｒｎａベースの遺伝子発現 |
| EP3094746A1 (en) | 2014-01-14 | 2016-11-23 | Daiichi Sankyo Company, Limited | Gene signatures associated with sensitivity to mdm2 inhibitors |
| MX373045B (es) | 2014-04-17 | 2020-05-26 | Univ Michigan Regents | Inhibidores de mdm2 y metodos terapeuticos que utilizan el mismo. |
| JP2017532959A (ja) | 2014-10-09 | 2017-11-09 | 第一三共株式会社 | Ｍｄｍ２阻害剤に対する感受性の遺伝子シグネチャーに基づく予測因子に関するアルゴリズム |
| WO2016059241A2 (en) | 2014-10-17 | 2016-04-21 | Biomirna Holdings Ltd. | Lung cancer diagnostics and therapeutics with mir-660 |
| CN108024535A (zh) | 2015-07-02 | 2018-05-11 | 大塚制药株式会社 | 冻干药物组合物 |
| GB201517217D0 (en) | 2015-09-29 | 2015-11-11 | Astex Therapeutics Ltd And Cancer Res Technology Ltd | Pharmaceutical compounds |
| GB201517216D0 (en) | 2015-09-29 | 2015-11-11 | Cancer Res Technology Ltd And Astex Therapeutics Ltd | Pharmaceutical compounds |
| IL291017B2 (en) | 2015-10-21 | 2023-11-01 | Otsuka Pharma Co Ltd | Benzolactam compounds as protein kinase inhibitors |
| TWI734715B (zh) | 2015-11-19 | 2021-08-01 | 美商卡默森屈有限公司 | 趨化因子受體調節劑 |
| GB201704965D0 (en) * | 2017-03-28 | 2017-05-10 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| GB201704966D0 (en) | 2017-03-28 | 2017-05-10 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| CA3050645A1 (en) | 2018-07-27 | 2020-01-27 | Ottawa Hospital Research Institute | Treatment of acute myeloid leukemia |
| WO2020169073A1 (en) | 2019-02-24 | 2020-08-27 | Ascentage Pharma (Suzhou) Co., Ltd. | Treatment methods and biomarkers for mdm2 inhibitors |
| GB201919219D0 (en) | 2019-12-23 | 2020-02-05 | Otsuka Pharma Co Ltd | Cancer biomarkers |
| US20230313313A1 (en) | 2020-08-27 | 2023-10-05 | Otsuka Pharmaceutical Co., Ltd. | Biomarkers for cancer therapy using mdm2 antagonists |
| GB202103080D0 (en) | 2021-03-04 | 2021-04-21 | Otsuka Pharma Co Ltd | Cancer biomarkers |
-
2017
- 2017-03-28 GB GBGB1704965.1A patent/GB201704965D0/en not_active Ceased
-
2018
- 2018-03-28 WO PCT/GB2018/050845 patent/WO2018178691A1/en not_active Ceased
- 2018-03-28 US US16/498,207 patent/US11603367B2/en active Active
- 2018-03-28 CN CN201880022720.4A patent/CN110678462B/zh active Active
- 2018-03-28 EP EP18715926.4A patent/EP3601272A1/en active Pending
- 2018-03-28 JP JP2019552594A patent/JP7495790B2/ja active Active
- 2018-03-28 KR KR1020197030377A patent/KR102673967B1/ko active Active
-
2023
- 2023-01-25 US US18/159,452 patent/US12077526B2/en active Active
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2024
- 2024-07-26 US US18/785,847 patent/US20250074900A1/en active Pending
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