AU2017379315B2 - Coumarin compounds and their uses as fluorescent labels - Google Patents

Coumarin compounds and their uses as fluorescent labels Download PDF

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AU2017379315B2
AU2017379315B2 AU2017379315A AU2017379315A AU2017379315B2 AU 2017379315 B2 AU2017379315 B2 AU 2017379315B2 AU 2017379315 A AU2017379315 A AU 2017379315A AU 2017379315 A AU2017379315 A AU 2017379315A AU 2017379315 B2 AU2017379315 B2 AU 2017379315B2
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AU2017379315A1 (en
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Nikolai Romanov
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Illumina Cambridge Ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04Ortho-condensed systems
    • C07D491/044Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/052Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14Ortho-condensed systems
    • C07D491/147Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
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    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06Pyrimidine radicals
    • C07H19/10Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
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    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/14Pyrrolo-pyrimidine radicals
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    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00Other synthetic dyes of known constitution
    • C09B57/02Coumarine dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12QMEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
    • C12Q1/6813Hybridisation assays
    • C12Q1/6816Hybridisation assays characterised by the detection means
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    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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    • C12Q1/00Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
    • C12Q1/6869Methods for sequencing
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    • C12Q1/00Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
    • C12Q1/6876Nucleic acid products used in the analysis of nucleic acids, e.g. primers or probes
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
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    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12QMEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q2563/00Nucleic acid detection characterized by the use of physical, structural and functional properties
    • C12Q2563/107Nucleic acid detection characterized by the use of physical, structural and functional properties fluorescence

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Analytical Chemistry (AREA)
  • Immunology (AREA)
  • Microbiology (AREA)
  • Biophysics (AREA)
  • Physics & Mathematics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Pyrane Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
AU2017379315A 2016-12-22 2017-12-15 Coumarin compounds and their uses as fluorescent labels Active AU2017379315B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2022204153A AU2022204153B2 (en) 2016-12-22 2022-06-14 Coumarin Compounds And Their Uses As Fluorescent Labels

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201662438006P 2016-12-22 2016-12-22
US62/438,006 2016-12-22
PCT/EP2017/083128 WO2018114710A1 (en) 2016-12-22 2017-12-15 Coumarin compounds and their uses as fluorescent labels

Related Child Applications (1)

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AU2017379315B2 true AU2017379315B2 (en) 2022-04-14

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AU2022204153A Active AU2022204153B2 (en) 2016-12-22 2022-06-14 Coumarin Compounds And Their Uses As Fluorescent Labels

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US (4) US10214768B2 (enExample)
EP (2) EP4257596A3 (enExample)
JP (1) JP2020504074A (enExample)
KR (1) KR102512190B1 (enExample)
CN (1) CN109476674B (enExample)
AU (2) AU2017379315B2 (enExample)
CA (1) CA3025880C (enExample)
ES (1) ES2954284T3 (enExample)
IL (1) IL263358B (enExample)
SG (1) SG11201810611YA (enExample)
WO (1) WO2018114710A1 (enExample)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG11201810611YA (en) * 2016-12-22 2018-12-28 Illumina Cambridge Ltd Coumarin compounds and their uses as fluorescent labels
KR20210125471A (ko) 2018-10-05 2021-10-18 안나푸르나 바이오, 인코포레이티드 Apj 수용체 활성과 관련된 병태를 치료하기 위한 화합물 및 조성물
US11293061B2 (en) 2018-12-26 2022-04-05 Illumina Cambridge Limited Sequencing methods using nucleotides with 3′ AOM blocking group
WO2020178231A1 (en) * 2019-03-01 2020-09-10 Illumina, Inc. Multiplexed fluorescent detection of analytes
NL2023327B1 (en) * 2019-03-01 2020-09-17 Illumina Inc Multiplexed fluorescent detection of analytes
US11421271B2 (en) * 2019-03-28 2022-08-23 Illumina Cambridge Limited Methods and compositions for nucleic acid sequencing using photoswitchable labels
CN112794857B (zh) * 2019-11-13 2023-09-19 湖南超亟检测技术有限责任公司 一种可用于亚铁离子检测的荧光探针及制备和应用
JP2023510454A (ja) 2019-11-27 2023-03-14 イルミナ ケンブリッジ リミテッド シクロオクタテトラエンを含有する色素及び組成物
WO2021183403A2 (en) * 2020-03-10 2021-09-16 Western Digital Technologies, Inc. Magnetic sensor arrays for nucleic acid sequencing and methods of making and using them
MX2022016492A (es) 2020-06-22 2023-03-06 Illumina Cambridge Ltd Nucleosidos y nucleotidos con grupo de bloqueo de acetal 3'.
US11981964B2 (en) * 2020-07-28 2024-05-14 Illumina Cambridge Limited Substituted coumarin dyes and uses as fluorescent labels
US20220195516A1 (en) 2020-12-17 2022-06-23 Illumina Cambridge Limited Methods, systems and compositions for nucleic acid sequencing
US20220195517A1 (en) * 2020-12-17 2022-06-23 Illumina Cambridge Limited Long stokes shift chromenoquinoline dyes and uses in sequencing applications
US20220195196A1 (en) * 2020-12-17 2022-06-23 Illumina Cambridge Limited Alkylpyridinium coumarin dyes and uses in sequencing applications
US20220195518A1 (en) 2020-12-22 2022-06-23 Illumina Cambridge Limited Methods and compositions for nucleic acid sequencing
CN114671843B (zh) * 2020-12-24 2023-07-04 郑州思昆生物工程有限公司 一种荧光化合物、荧光修饰核苷酸、试剂盒
WO2022243480A1 (en) 2021-05-20 2022-11-24 Illumina, Inc. Compositions and methods for sequencing by synthesis
EP4499862A1 (en) 2022-03-28 2025-02-05 Illumina, Inc. Labeled avidin and methods for sequencing
AU2023246772A1 (en) * 2022-03-29 2024-01-18 Illumina Inc. Chromenoquinoline dyes and uses in sequencing
US20230332197A1 (en) 2022-03-31 2023-10-19 Illumina Singapore Pte. Ltd. Nucleosides and nucleotides with 3' vinyl blocking group
AU2023246851A1 (en) 2022-03-31 2024-01-18 Illumina, Inc. Compositions and methods for improving sequencing signals
EP4532759A1 (en) 2022-05-31 2025-04-09 Illumina, Inc. Compositions and methods for nucleic acid sequencing
EP4594428A2 (en) 2022-09-30 2025-08-06 Illumina, Inc. Compositions and methods for reducing photo damage during sequencing
CA3246536A1 (en) 2022-12-22 2024-06-27 Illumina, Inc. TRANSITION METAL CATALYST COMPOSITIONS AND SYNTHETIC SEQUENCE PROCESSES
CA3246545A1 (en) 2022-12-22 2024-06-27 Illumina, Inc. PALLADIUM CATALYST COMPOSITIONS AND SYNTHETIC SEQUENCE PROCESSES
EP4642931A1 (en) 2022-12-27 2025-11-05 Illumina, Inc. Methods of sequencing using 3´ allyl blocked nucleotides
US20240327909A1 (en) 2023-03-30 2024-10-03 Illumina, Inc. Compositions and methods for nucleic acid sequencing
WO2025049700A1 (en) 2023-08-31 2025-03-06 Illumina, Inc. Compositions and methods for nucleic acid sequencing
WO2025144716A1 (en) 2023-12-28 2025-07-03 Illumina, Inc. Nucleotides with enzymatically cleavable 3'-o-glycoside blocking groups for sequencing
WO2025184226A1 (en) 2024-02-28 2025-09-04 Illumina, Inc. Nucleotides with terminal phosphate capping
WO2025188906A1 (en) 2024-03-08 2025-09-12 Illumina, Inc. Modified adenosine nucleotides
WO2025221895A1 (en) 2024-04-19 2025-10-23 Illumina, Inc. Water soluble polymer scaffolds for dye labeling
WO2025230914A1 (en) 2024-04-29 2025-11-06 Illumina, Inc. Nucleotides with enzyme-triggered self-immolative linkers for sequencing by synthesis

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2126811A1 (en) * 1971-05-29 1972-12-14 Basf Ag Fluorescent pigments dyes - of the coumarin series for synthetic fibres and plastics
WO2003074519A1 (en) * 2002-03-06 2003-09-12 Novartis Ag Coumarines useful as biomarkers
WO2009124800A1 (de) * 2008-04-09 2009-10-15 Henkel Ag & Co. Kgaa Kationische direktzieher und mittel zum färben keratinhaltigen fasern

Family Cites Families (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5302509A (en) 1989-08-14 1994-04-12 Beckman Instruments, Inc. Method for sequencing polynucleotides
JPH0743896A (ja) * 1993-07-28 1995-02-14 Toyobo Co Ltd 光重合性組成物
US5846719A (en) 1994-10-13 1998-12-08 Lynx Therapeutics, Inc. Oligonucleotide tags for sorting and identification
WO1998044151A1 (en) 1997-04-01 1998-10-08 Glaxo Group Limited Method of nucleic acid amplification
US6465178B2 (en) 1997-09-30 2002-10-15 Surmodics, Inc. Target molecule attachment to surfaces
US6485944B1 (en) 1997-10-10 2002-11-26 President And Fellows Of Harvard College Replica amplification of nucleic acid arrays
US6093518A (en) * 1998-02-09 2000-07-25 Kansai Paint Co., Ltd. Visible laser-curable composition
ATE309390T1 (de) 1998-07-30 2005-11-15 Solexa Ltd Matrizen von biomolekülen und ihre verwendung in sequenzierung
GB0002310D0 (en) 2000-02-01 2000-03-22 Solexa Ltd Polynucleotide sequencing
AR021833A1 (es) 1998-09-30 2002-08-07 Applied Research Systems Metodos de amplificacion y secuenciacion de acido nucleico
US6391937B1 (en) 1998-11-25 2002-05-21 Motorola, Inc. Polyacrylamide hydrogels and hydrogel arrays made from polyacrylamide reactive prepolymers
US6664061B2 (en) 1999-06-25 2003-12-16 Amersham Biosciences Ab Use and evaluation of a [2+2] photoaddition in immobilization of oligonucleotides on a three-dimensional hydrogel matrix
US6372813B1 (en) 1999-06-25 2002-04-16 Motorola Methods and compositions for attachment of biomolecules to solid supports, hydrogels, and hydrogel arrays
WO2002012566A2 (en) 2000-08-09 2002-02-14 Motorola, Inc. The use and evaluation of a [2+2] photocycloaddition in immobilization of oligonucleotides on a three-dimensional hydrogel matrix
JP4837174B2 (ja) * 2001-02-02 2011-12-14 株式会社林原生物化学研究所 クマリン誘導体およびその製造方法、それを利用した発光剤、発光素子
DE10160524A1 (de) * 2001-12-05 2003-06-26 Dyomics Gmbh Neue Fluoreszenzmarker mit großem Stokes-Shift
EP3438116B1 (en) 2002-08-23 2021-02-17 Illumina Cambridge Limited Labelled nucleotides
JP2006509040A (ja) 2002-08-23 2006-03-16 ソレックサ リミテッド 修飾されたヌクレオチド
DE10356130A1 (de) * 2003-11-28 2005-06-23 Dyomics Gmbh Neue Polymethinfarbstoffe auf Cumarin-Basis mit einstellbarem Stokes-Shift
US7563907B2 (en) * 2002-12-05 2009-07-21 Dyomics Gmbh Compounds based on polymethines
US6727362B1 (en) * 2003-06-19 2004-04-27 Labeltek Inc. Coumarin derivatives and an electroluminescent (EL) device using the coumarin derivatives
GB0321306D0 (en) 2003-09-11 2003-10-15 Solexa Ltd Modified polymerases for improved incorporation of nucleotide analogues
GB0326073D0 (en) 2003-11-07 2003-12-10 Solexa Ltd Improvements in or relating to polynucleotide arrays
EP1701785A1 (en) 2004-01-07 2006-09-20 Solexa Ltd. Modified molecular arrays
US20080194522A1 (en) * 2004-08-25 2008-08-14 Gong Chen Development of Fluorogenic Substrates For Monoamine Oxidases (Mao-A and Mao-B)
JP4990886B2 (ja) 2005-05-10 2012-08-01 ソレックサ リミテッド 改良ポリメラーゼ
GB0517097D0 (en) 2005-08-19 2005-09-28 Solexa Ltd Modified nucleosides and nucleotides and uses thereof
USRE49362E1 (en) 2006-05-18 2023-01-10 Illumina Cambridge Limited Dye compounds and the use of their labelled conjugates
WO2010063732A1 (en) * 2008-12-01 2010-06-10 Biotype Ag Novel combination of fluorescent dyes for the detection of nucleic acids
EP2370110B1 (en) 2008-12-25 2017-08-02 Canon Kabushiki Kaisha Labeling composition for intraocular tissue, labeling method of intraocular tissue, and screening method
CN101851505B (zh) * 2010-06-09 2013-02-27 深圳丹邦投资集团有限公司 一种香豆素类有机电致荧光材料及其合成方法
CN107190078A (zh) * 2011-05-06 2017-09-22 凯杰有限公司 包含内部标记引物的核酸的测序、扩增和检测方法
ES2639938T5 (es) 2011-09-23 2021-05-07 Illumina Inc Métodos y composiciones para la secuenciación de ácidos nucleicos
US9164086B2 (en) * 2011-10-18 2015-10-20 Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V. Fluorescent dyes with phosphorylated hydroxymethyl groups and their use in light microscopy and imaging techniques
JP6174881B2 (ja) * 2012-04-04 2017-08-02 住友化学株式会社 着色硬化性樹脂組成物
US9012022B2 (en) 2012-06-08 2015-04-21 Illumina, Inc. Polymer coatings
ES2620427T3 (es) * 2013-03-08 2017-06-28 Illumina Cambridge Limited Compuestos rodamina y su uso como marcadores fluorescentes
BR112015022448B1 (pt) 2013-03-15 2020-12-08 Illumina Cambridge Limited molécula de nucleotídeo ou nucleosídeo modificado, métodos para preparar o crescimento de polinucleotídeo complementar a polinucleotídeo alvo de fita simples em reação de sequenciação e para determinar a sequência de polinucleotídeo alvo de fita simples e kit
CN105218538B (zh) * 2015-09-24 2017-04-26 四川大学 取代的香豆素‑吡啶衍生物及其制备方法和用途
SG11201810611YA (en) * 2016-12-22 2018-12-28 Illumina Cambridge Ltd Coumarin compounds and their uses as fluorescent labels

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2126811A1 (en) * 1971-05-29 1972-12-14 Basf Ag Fluorescent pigments dyes - of the coumarin series for synthetic fibres and plastics
WO2003074519A1 (en) * 2002-03-06 2003-09-12 Novartis Ag Coumarines useful as biomarkers
WO2009124800A1 (de) * 2008-04-09 2009-10-15 Henkel Ag & Co. Kgaa Kationische direktzieher und mittel zum färben keratinhaltigen fasern

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EP3559004A1 (en) 2019-10-30
US10214768B2 (en) 2019-02-26
EP4257596A2 (en) 2023-10-11
EP3559004B1 (en) 2023-07-05
CN109476674A (zh) 2019-03-15
CA3025880A1 (en) 2018-06-28
KR102512190B1 (ko) 2023-03-21
IL263358A (en) 2018-12-31
AU2017379315A1 (en) 2018-12-13
US20210155977A1 (en) 2021-05-27
US10533211B2 (en) 2020-01-14
CA3025880C (en) 2020-01-28
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