JP2020503274A5 - - Google Patents
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- JP2020503274A5 JP2020503274A5 JP2019529472A JP2019529472A JP2020503274A5 JP 2020503274 A5 JP2020503274 A5 JP 2020503274A5 JP 2019529472 A JP2019529472 A JP 2019529472A JP 2019529472 A JP2019529472 A JP 2019529472A JP 2020503274 A5 JP2020503274 A5 JP 2020503274A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- aryl
- heteroaryl
- alkynyl
- 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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- 125000000623 heterocyclic group Chemical group 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 48
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 44
- 125000000304 alkynyl group Chemical group 0.000 claims description 42
- 125000003342 alkenyl group Chemical group 0.000 claims description 41
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 40
- -1 alkoxyfluoroalkyl Chemical group 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- IGXWBGJHJZYPQS-SSDOTTSWSA-N D-Luciferin Chemical class OC(=O)[C@H]1CSC(C=2SC3=CC=C(O)C=C3N=2)=N1 IGXWBGJHJZYPQS-SSDOTTSWSA-N 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 108060001084 Luciferase Proteins 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000005089 Luciferase Substances 0.000 claims description 9
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 8
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- 108090000790 Enzymes Proteins 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 4
- 238000004020 luminiscence type Methods 0.000 claims description 3
- CPTUWIGDJUMCRJ-NSHDSACASA-N (4S)-2-(6,7-dihydro-5H-pyrrolo[3,2-f][1,3]benzothiazol-2-yl)-5,5-dimethyl-4H-1,3-thiazole-4-carboxylic acid Chemical compound N1=C(SC=2C1=CC=1CCNC=1C=2)C=1SC([C@@H](N=1)C(=O)O)(C)C CPTUWIGDJUMCRJ-NSHDSACASA-N 0.000 claims description 2
- FWRZLSGXVGEFQS-ZDUSSCGKSA-N (4S)-2-(7-aminobenzo[g][1,3]benzothiazol-2-yl)-5,5-dimethyl-4H-1,3-thiazole-4-carboxylic acid Chemical compound NC=1C=C2C=CC=3N=C(SC=3C2=CC=1)C=1SC([C@@H](N=1)C(=O)O)(C)C FWRZLSGXVGEFQS-ZDUSSCGKSA-N 0.000 claims description 2
- KUEFORRJXBJEJM-LBPRGKRZSA-N (4S)-2-[6-(3-hydroxypropylamino)-1,3-benzothiazol-2-yl]-5,5-dimethyl-4H-1,3-thiazole-4-carboxylic acid Chemical compound OCCCNC1=CC2=C(N=C(S2)C=2SC([C@@H](N=2)C(=O)O)(C)C)C=C1 KUEFORRJXBJEJM-LBPRGKRZSA-N 0.000 claims description 2
- UDXMNUQVKAQMAK-ZDUSSCGKSA-N (4S)-5,5-dimethyl-2-(6-pyrrolidin-1-yl-1,3-benzothiazol-2-yl)-4H-1,3-thiazole-4-carboxylic acid Chemical compound CC1([C@@H](N=C(S1)C=1SC2=C(N=1)C=CC(=C2)N1CCCC1)C(=O)O)C UDXMNUQVKAQMAK-ZDUSSCGKSA-N 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- HKGFMDMTFXAFKJ-UHFFFAOYSA-N C(C)C1(C(N=C(S1)C=1SC2=C(N=1)C=C(C(=C2)O)F)C(=O)O)CC Chemical compound C(C)C1(C(N=C(S1)C=1SC2=C(N=1)C=C(C(=C2)O)F)C(=O)O)CC HKGFMDMTFXAFKJ-UHFFFAOYSA-N 0.000 claims description 2
- IUAOEQJFYSNPKL-UHFFFAOYSA-N C(C)C1(C(N=C(S1)C=1SC2=C(N=1)C=CC(=C2)O)C(=O)O)CC Chemical compound C(C)C1(C(N=C(S1)C=1SC2=C(N=1)C=CC(=C2)O)C(=O)O)CC IUAOEQJFYSNPKL-UHFFFAOYSA-N 0.000 claims description 2
- LKNWGYRYOIWKJN-VIFPVBQESA-N FC=1C(=CC2=C(N=C(S2)C=2SC([C@@H](N=2)C(=O)O)(C)C)C=1)O Chemical compound FC=1C(=CC2=C(N=C(S2)C=2SC([C@@H](N=2)C(=O)O)(C)C)C=1)O LKNWGYRYOIWKJN-VIFPVBQESA-N 0.000 claims description 2
- LKNWGYRYOIWKJN-SECBINFHSA-N FC=1C(=CC2=C(N=C(S2)C=2SC([C@H](N=2)C(=O)O)(C)C)C=1)O Chemical compound FC=1C(=CC2=C(N=C(S2)C=2SC([C@H](N=2)C(=O)O)(C)C)C=1)O LKNWGYRYOIWKJN-SECBINFHSA-N 0.000 claims description 2
- ODEFKOSEFACSIP-UHFFFAOYSA-N FC=1C(=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCCCC3)C=1)O Chemical compound FC=1C(=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCCCC3)C=1)O ODEFKOSEFACSIP-UHFFFAOYSA-N 0.000 claims description 2
- UIINYUSVOLCVEM-UHFFFAOYSA-N OC1=CC2=C(N=C(S2)C=2SC(C(N=2)C(=O)O)(CCC)CCC)C=C1 Chemical compound OC1=CC2=C(N=C(S2)C=2SC(C(N=2)C(=O)O)(CCC)CCC)C=C1 UIINYUSVOLCVEM-UHFFFAOYSA-N 0.000 claims description 2
- ZKMIZRVVFWEERX-UHFFFAOYSA-N OC1=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCC(CC3)C)C=C1 Chemical compound OC1=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCC(CC3)C)C=C1 ZKMIZRVVFWEERX-UHFFFAOYSA-N 0.000 claims description 2
- FEGFZCLCDNCUBZ-UHFFFAOYSA-N OC1=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCCC3)C=C1 Chemical compound OC1=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCCC3)C=C1 FEGFZCLCDNCUBZ-UHFFFAOYSA-N 0.000 claims description 2
- QVZZOBKXNHXEQX-UHFFFAOYSA-N OC1=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCCCC3)C=C1 Chemical compound OC1=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCCCC3)C=C1 QVZZOBKXNHXEQX-UHFFFAOYSA-N 0.000 claims description 2
- BUFUALJVTKYRCD-UHFFFAOYSA-N OC1=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCCCCC3)C=C1 Chemical compound OC1=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCCCCC3)C=C1 BUFUALJVTKYRCD-UHFFFAOYSA-N 0.000 claims description 2
- KOIVGRULBNSRPP-UHFFFAOYSA-N OC1=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCN(CC3)C)C=C1 Chemical compound OC1=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCN(CC3)C)C=C1 KOIVGRULBNSRPP-UHFFFAOYSA-N 0.000 claims description 2
- KFHQMZPTKPFSRN-UHFFFAOYSA-N OC1=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCOCC3)C=C1 Chemical compound OC1=CC2=C(N=C(S2)C=2SC3(C(N=2)C(=O)O)CCOCC3)C=C1 KFHQMZPTKPFSRN-UHFFFAOYSA-N 0.000 claims description 2
- GZLBPLZQEWPZJE-UHFFFAOYSA-N OC1=CC2=C(N=C(S2)C=2SC3(CC3)C(N=2)C(=O)O)C=C1 Chemical compound OC1=CC2=C(N=C(S2)C=2SC3(CC3)C(N=2)C(=O)O)C=C1 GZLBPLZQEWPZJE-UHFFFAOYSA-N 0.000 claims description 2
- OZTICKGMSLZQPD-UHFFFAOYSA-N OC1=CC2=C(N=C(S2)C=2SC3(CCC3)C(N=2)C(=O)O)C=C1 Chemical compound OC1=CC2=C(N=C(S2)C=2SC3(CCC3)C(N=2)C(=O)O)C=C1 OZTICKGMSLZQPD-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000001727 in vivo Methods 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 238000000338 in vitro Methods 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- VRTNFECUWSQRPC-UHFFFAOYSA-N 2-(6-amino-1,3-benzothiazol-2-yl)-5,5-dimethyl-4H-1,3-thiazole-4-carboxylic acid Chemical compound NC1=CC2=C(N=C(S2)C=2SC(C(N=2)C(=O)O)(C)C)C=C1 VRTNFECUWSQRPC-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 5
- 230000009261 transgenic effect Effects 0.000 description 3
- XXZCJMWSTWCVLY-UHFFFAOYSA-N 2-(6-hydroxy-1,3-benzothiazol-2-yl)-5,5-dimethyl-4H-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1C(C)(C)SC(C=2SC3=CC(O)=CC=C3N=2)=N1 XXZCJMWSTWCVLY-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- NZTHROHVCHLWHT-UHFFFAOYSA-N C(C1=CC=CC=C1)C1(C(N=C(S1)C=1SC2=C(N=1)C=CC(=C2)O)C(=O)O)CC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)C1(C(N=C(S1)C=1SC2=C(N=1)C=CC(=C2)O)C(=O)O)CC1=CC=CC=C1 NZTHROHVCHLWHT-UHFFFAOYSA-N 0.000 description 1
- 0 CC1(C=C)SC(c2nc(c(*)c(*)c(*)c3*)c3[s]2)=NC1C(*)=O Chemical compound CC1(C=C)SC(c2nc(c(*)c(*)c(*)c3*)c3[s]2)=NC1C(*)=O 0.000 description 1
- CYCGRDQQIOGCKX-UHFFFAOYSA-N Dehydro-luciferin Natural products OC(=O)C1=CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 CYCGRDQQIOGCKX-UHFFFAOYSA-N 0.000 description 1
- BJGNCJDXODQBOB-UHFFFAOYSA-N Fivefly Luciferin Natural products OC(=O)C1CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 BJGNCJDXODQBOB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DDWFXDSYGUXRAY-UHFFFAOYSA-N Luciferin Natural products CCc1c(C)c(CC2NC(=O)C(=C2C=C)C)[nH]c1Cc3[nH]c4C(=C5/NC(CC(=O)O)C(C)C5CC(=O)O)CC(=O)c4c3C DDWFXDSYGUXRAY-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022110372A JP7696867B2 (ja) | 2016-12-01 | 2022-07-08 | ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662428707P | 2016-12-01 | 2016-12-01 | |
| US62/428,707 | 2016-12-01 | ||
| PCT/US2017/064284 WO2018102726A1 (en) | 2016-12-01 | 2017-12-01 | 5,5-disubstituted luciferins and their use in luciferase-based assays |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022110372A Division JP7696867B2 (ja) | 2016-12-01 | 2022-07-08 | ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020503274A JP2020503274A (ja) | 2020-01-30 |
| JP2020503274A5 true JP2020503274A5 (https=) | 2021-01-14 |
| JP7104702B2 JP7104702B2 (ja) | 2022-07-21 |
Family
ID=60703215
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019529472A Active JP7104702B2 (ja) | 2016-12-01 | 2017-12-01 | ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用 |
| JP2022110372A Active JP7696867B2 (ja) | 2016-12-01 | 2022-07-08 | ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022110372A Active JP7696867B2 (ja) | 2016-12-01 | 2022-07-08 | ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用 |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US10400264B2 (https=) |
| EP (1) | EP3548470B1 (https=) |
| JP (2) | JP7104702B2 (https=) |
| WO (1) | WO2018102726A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7104702B2 (ja) * | 2016-12-01 | 2022-07-21 | プロメガ コーポレイション | ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用 |
| EP3661932B1 (en) | 2017-08-04 | 2021-10-06 | Promega Corporation | Compositions and methods for stabilizing benzothiazole luciferin analogs |
| JP2021525269A (ja) | 2018-05-29 | 2021-09-24 | セルシィ セラピューティクス，インコーポレーテッド | 疼痛処置のための化合物、それを含む組成物及びそれを使用する方法 |
| WO2019236731A1 (en) * | 2018-06-05 | 2019-12-12 | Promega Corporation | Luciferase enzymes for use with thermostable luciferins in bioluminescent assays |
| US11980668B2 (en) | 2018-11-09 | 2024-05-14 | R.P. Scherer Technologies, Llc | Sulfatase-cleavable linkers for antibody-drug conjugates |
| WO2020159565A1 (en) * | 2019-02-01 | 2020-08-06 | Cersci Therapeutics, Inc. | Methods of treating post-surgical pain with a thiazoline anti-hyperalgesic agent |
| US20200246317A1 (en) * | 2019-02-01 | 2020-08-06 | Cersci Therapeutics, Inc. | Methods of treating diabetic neuropathy with a thiazoline anti-hyperalgesic agent |
| SG11202110561XA (en) | 2019-05-10 | 2021-10-28 | Cersci Therapeutics Inc | Manufacturing methods and polymorphs of a thiazoline anti-hyperalgesic agent |
| CN110590700B (zh) * | 2019-09-12 | 2021-09-21 | 山东大学 | 多元杂环化合物与制备方法及其在检测半胱氨酸中的应用 |
| JP7448993B2 (ja) * | 2019-09-26 | 2024-03-13 | ウィタヤシリメティ インスティチュート オブ サイエンス アンド テクノロジー | ルシフェリン誘導体及びその合成方法 |
| CN114478578B (zh) * | 2021-12-24 | 2024-03-29 | 上海中医药大学 | 测定羧酸酯酶1的特异性生物发光探针底物及其制备方法和应用 |
| CN115745987B (zh) * | 2022-08-05 | 2026-03-27 | 华东理工大学 | 一种荧光素酶底物及其制备方法和用途 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5965736A (en) * | 1996-01-16 | 1999-10-12 | Lumigen, Inc. | Compositions and methods for generating red chemiluminescence |
| JP2005500281A (ja) * | 2001-06-01 | 2005-01-06 | エフ．ホフマン−ラ ロシュ アーゲー | ルシフェリンヒドラジド |
| US7074891B2 (en) | 2003-02-07 | 2006-07-11 | Posco | Leukocyte stimulating peptides |
| EP2778234B1 (en) | 2005-05-31 | 2017-09-27 | Promega Corporation | Luminogenic and fluorogenic compounds and methods to detect molecules or conditions |
| CA2768352C (en) * | 2009-07-16 | 2016-10-11 | Beckman Coulter, Inc. | Novel fluorescent dyes and uses thereof |
| BR112013010487B1 (pt) * | 2010-11-02 | 2021-02-02 | Promega Corporation | compostos de coelenterazina, kit compreendendo ditos compostos e método para detectar luminescência em uma amostra in vitro |
| US9370588B2 (en) * | 2013-01-04 | 2016-06-21 | University Of Massachusetts | Luciferin amides |
| JP6495232B2 (ja) | 2013-03-12 | 2019-04-03 | プロメガ コーポレイションＰｒｏｍｅｇａ Ｃｏｒｐｏｒａｔｉｏｎ | 赤方偏移ルシフェリン及びその使用方法 |
| JP7104702B2 (ja) * | 2016-12-01 | 2022-07-21 | プロメガ コーポレイション | ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用 |
| EP3661932B1 (en) | 2017-08-04 | 2021-10-06 | Promega Corporation | Compositions and methods for stabilizing benzothiazole luciferin analogs |
-
2017
- 2017-12-01 JP JP2019529472A patent/JP7104702B2/ja active Active
- 2017-12-01 WO PCT/US2017/064284 patent/WO2018102726A1/en not_active Ceased
- 2017-12-01 US US15/829,581 patent/US10400264B2/en active Active
- 2017-12-01 EP EP17817600.4A patent/EP3548470B1/en active Active
-
2019
- 2019-07-19 US US16/516,974 patent/US10913972B2/en active Active
-
2022
- 2022-07-08 JP JP2022110372A patent/JP7696867B2/ja active Active
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