CA3011328C - Chemolight Probes for In Vivo Diagnostics and Imaging - Google Patents

Chemolight Probes for In Vivo Diagnostics and Imaging

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Publication number
CA3011328C
CA3011328C CA3011328A CA3011328A CA3011328C CA 3011328 C CA3011328 C CA 3011328C CA 3011328 A CA3011328 A CA 3011328A CA 3011328 A CA3011328 A CA 3011328A CA 3011328 C CA3011328 C CA 3011328C
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Prior art keywords
compound
group
absent
alkyl
alkylene
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CA3011328A
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English (en)
French (fr)
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CA3011328A1 (en
Inventor
Doron Shabat
Ronit Satchi-Fainaro
Nir HANANYA
Ori GREEN
Tal EILON
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Ramot at Tel Aviv University Ltd
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/005—Fluorescence in vivo characterised by the carrier molecule carrying the fluorescent agent
    • A61K49/0052—Small organic molecules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/6551—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring
    • C07F9/65512—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0066—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
    • C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Biomedical Technology (AREA)
  • Materials Engineering (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Hematology (AREA)
  • Immunology (AREA)
  • Urology & Nephrology (AREA)
  • Medicinal Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Physics & Mathematics (AREA)
  • Food Science & Technology (AREA)
  • Microbiology (AREA)
  • Cell Biology (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Saccharide Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA3011328A 2016-01-26 2017-01-24 Chemolight Probes for In Vivo Diagnostics and Imaging Active CA3011328C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201662287127P 2016-01-26 2016-01-26
US62/287,127 2016-01-26
US201662431618P 2016-12-08 2016-12-08
US62/431,618 2016-12-08
PCT/IL2017/050088 WO2017130191A1 (en) 2016-01-26 2017-01-24 Chemiluminescent probes for diagnostics and in vivo imaging

Publications (2)

Publication Number Publication Date
CA3011328A1 CA3011328A1 (en) 2017-08-03
CA3011328C true CA3011328C (en) 2024-09-17

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CA3011328A Active CA3011328C (en) 2016-01-26 2017-01-24 Chemolight Probes for In Vivo Diagnostics and Imaging

Country Status (8)

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US (4) US10660974B2 (enExample)
EP (1) EP3408349B1 (enExample)
JP (1) JP6915943B2 (enExample)
KR (1) KR102717614B1 (enExample)
CN (1) CN108884386B (enExample)
CA (1) CA3011328C (enExample)
ES (1) ES2866900T3 (enExample)
WO (1) WO2017130191A1 (enExample)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11241507B2 (en) 2017-05-24 2022-02-08 Ramot At Tel-Aviv University Ltd. Near-infrared chemiluminescent probes for in-vivo imaging
WO2018216012A1 (en) 2017-05-24 2018-11-29 Ramot At Tel-Aviv University Ltd. Chemiluminescent probes for imaging/detection of proteases
WO2019224339A1 (en) 2018-05-25 2019-11-28 Biosynth Ag Long wavelength emitting chemiluminescent probes
US11649475B2 (en) * 2018-05-25 2023-05-16 Ramot At Tel-Aviv University Ltd. Dioxetane compounds and their use for the detection of microorganisms
CN111073633B (zh) * 2018-10-22 2023-07-25 北京工商大学 一种萘环类苯硫酚荧光探针
WO2020159448A1 (en) * 2019-02-01 2020-08-06 Nanyang Technological University Molecular renal probes for detecting acute kidney injury
CN110437274A (zh) * 2019-08-28 2019-11-12 南京工业大学 一种用于检测氟离子的探针、制备方法及应用
CN110804009B (zh) * 2019-10-10 2025-12-12 华东理工大学 一类化学发光强度高、波长长、稳定性好的化学发光底物及其制备方法和应用
WO2021086977A1 (en) * 2019-10-28 2021-05-06 Beckman Coulter, Inc. Rapid, high-intensity chemiluminescent dioxetanes
KR102332454B1 (ko) * 2019-12-18 2021-11-29 고려대학교 산학협력단 암 세포 검출용 발광 프로브 화합물 및 이를 포함하는 암 세포 검출용 발광 센서
US20240277873A1 (en) * 2021-08-11 2024-08-22 Nanyang Technological University Ultrabright chemiluminescent probes for detection and imaging
CN114315791B (zh) * 2021-12-22 2023-12-08 东南大学 用于实现手术导航和微小转移瘤成像的小分子化学发光探针及其制备方法和用途
CN114478473B (zh) * 2022-01-25 2024-05-03 南方医科大学 一种亮氨酸氨基肽酶化学发光检测试剂的合成及应用
JP2023110666A (ja) 2022-01-28 2023-08-09 シスメックス株式会社 化合物またはその塩、組成物、化学発光方法、化学発光シグナル測定方法、試薬、試薬キットおよび被検物質測定方法
CN115417863B (zh) * 2022-09-30 2024-02-02 徐州医科大学 一种二氧化硫近红外化学发光探针及其制备方法和应用
CN115894581B (zh) * 2022-10-26 2024-07-09 徐州医科大学 一种β-葡萄糖醛酸苷酶化学发光探针及其制备方法和应用
CN115819416B (zh) * 2022-11-29 2024-06-25 遵义医科大学 一种用于检测和区分的多模态化学发光分子及其应用
CN116217515B (zh) * 2022-12-20 2024-06-18 华南师范大学 一种亚甲基蓝型探针及其制备方法和在检测半胱氨酸中的应用
WO2024147125A1 (en) * 2023-01-04 2024-07-11 Ramot At Tel-Aviv University Ltd. Cyclobutyl-substituted phenoxy-dioxetanes and uses thereof
CN116606220A (zh) * 2023-03-21 2023-08-18 华东理工大学 一种单组分有机余辉化合物及其生物检测的应用
CN116410064A (zh) * 2023-04-13 2023-07-11 西安交通大学 一种合成2-(α-甲氧基-3-羟基苯亚甲基)金刚烷类化合物的方法
CN116655716A (zh) * 2023-04-27 2023-08-29 湖南师范大学 一种检测β-半乳糖苷酶的化学发光探针、制备方法及其应用
US20240386087A1 (en) 2023-05-17 2024-11-21 The Government of the United States of America, as represented by the Secretary of Homeland Security DNA Access Control System
CN117059804B (zh) * 2023-10-13 2024-03-19 瑞浦兰钧能源股份有限公司 一种化学预锂剂、锂离子电池及其制备方法
CN117442269B (zh) * 2023-12-22 2024-12-20 中日友好医院(中日友好临床医学研究所) 一种手术缝合针的搜寻系统及方法
CN119409748A (zh) * 2025-01-06 2025-02-11 四川省医学科学院·四川省人民医院 一种N-乙酰-β-D-氨基葡萄糖酶的化学发光探针、试剂盒及其制备方法和应用
CN119798211A (zh) * 2025-01-23 2025-04-11 西安交通大学 一种巯基化合物激活型化学发光探针及其合成方法和应用

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4983779A (en) * 1986-07-17 1991-01-08 The Board Of Governors Of Wayne State University Process for the preparation of vinyl ethers
US5616729A (en) * 1986-07-17 1997-04-01 Board Of Governors Of Wayne State University Enhanced chemiluminescence from 1,2-dioxetanes through energy transfer to tethered fluorescers
ES2271944T3 (es) * 1994-10-28 2007-04-16 Gen-Probe Incorporated Composiciones y metodos para la deteccion y cuantificacion simultaneas de multiples secuencias especificas de acidos nucleicos.
US5783381A (en) * 1995-10-19 1998-07-21 Tropix, Inc. Chemiluminescent 1,2-dioxetanes
JP3852140B2 (ja) * 1996-09-11 2006-11-29 東ソー株式会社 １，２−ジオキセタン誘導体
AU2001234612A1 (en) * 2000-01-28 2001-08-07 Brij Pal Giri Novel stabilized formulations for chemiluminescent assays
US7781229B2 (en) * 2004-04-14 2010-08-24 Michigan Diagnostics, Llc Ultra-sensitive chemiluminescent substrates for enzymes and their conjugates
KR102326217B1 (ko) 2014-01-08 2021-11-15 스미또모 가가꾸 가부시키가이샤 금속 착체 및 그것을 사용한 발광 소자
US10700292B2 (en) 2014-03-17 2020-06-30 Sumitomo Chemical Company, Limited Metal complex and light emitting device using the same

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WO2017130191A1 (en) 2017-08-03
EP3408349B1 (en) 2021-03-31
US10660974B2 (en) 2020-05-26
EP3408349A4 (en) 2019-10-23
JP6915943B2 (ja) 2021-08-11
EP3408349A1 (en) 2018-12-05
US11931429B2 (en) 2024-03-19
ES2866900T3 (es) 2021-10-20
US20220047725A1 (en) 2022-02-17
US20240197924A1 (en) 2024-06-20
JP2019509981A (ja) 2019-04-11
CN108884386A (zh) 2018-11-23
KR102717614B1 (ko) 2024-10-16
CN108884386B (zh) 2022-03-15
US20190290787A1 (en) 2019-09-26
CA3011328A1 (en) 2017-08-03
BR112018015334A2 (pt) 2018-12-18
KR20180108697A (ko) 2018-10-04
US12357709B2 (en) 2025-07-15
US20200237932A1 (en) 2020-07-30
US11179482B2 (en) 2021-11-23

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