ES2230710T3 - Composiciones generadoras de quimioluminiscencia y procedimientos correspondientes. - Google Patents
Composiciones generadoras de quimioluminiscencia y procedimientos correspondientes.Info
- Publication number
- ES2230710T3 ES2230710T3 ES98940778T ES98940778T ES2230710T3 ES 2230710 T3 ES2230710 T3 ES 2230710T3 ES 98940778 T ES98940778 T ES 98940778T ES 98940778 T ES98940778 T ES 98940778T ES 2230710 T3 ES2230710 T3 ES 2230710T3
- Authority
- ES
- Spain
- Prior art keywords
- substituted
- compound
- peroxidase
- formula
- group
- 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.)
- Expired - Lifetime
Links
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- 108040007629 peroxidase activity proteins Proteins 0.000 claims abstract description 96
- 238000006243 chemical reaction Methods 0.000 claims abstract description 71
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- 108090000790 Enzymes Proteins 0.000 claims abstract description 60
- 238000001514 detection method Methods 0.000 claims abstract description 45
- 150000002978 peroxides Chemical class 0.000 claims abstract description 40
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 27
- 238000003556 assay Methods 0.000 claims abstract description 26
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
- 102000003992 Peroxidases Human genes 0.000 claims abstract description 20
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- 102000013415 peroxidase activity proteins Human genes 0.000 claims description 94
- -1 phosphoryl groups Chemical group 0.000 claims description 76
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- 125000003118 aryl group Chemical group 0.000 claims description 34
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- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 19
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
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- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000002837 carbocyclic group Chemical group 0.000 claims description 9
- 238000003018 immunoassay Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 6
- 108010001336 Horseradish Peroxidase Proteins 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 6
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 238000009396 hybridization Methods 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 108020004707 nucleic acids Proteins 0.000 claims description 5
- 102000039446 nucleic acids Human genes 0.000 claims description 5
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- 238000001262 western blot Methods 0.000 claims description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 239000000427 antigen Substances 0.000 claims description 4
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- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003147 glycosyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229960005489 paracetamol Drugs 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 238000010998 test method Methods 0.000 claims description 3
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 claims description 2
- DIBXSCRTXGVRFD-UHFFFAOYSA-N 4-(1H-imidazol-2-yl)phenol Chemical compound C1=CC(O)=CC=C1C1=NC=CN1 DIBXSCRTXGVRFD-UHFFFAOYSA-N 0.000 claims description 2
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 claims description 2
- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 claims description 2
- 108010073997 Bromide peroxidase Proteins 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
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- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229950011260 betanaphthol Drugs 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 230000002860 competitive effect Effects 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
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- 229910052751 metal Inorganic materials 0.000 claims description 2
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- 108010029942 microperoxidase Proteins 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims 3
- GPTXWRGISTZRIO-UHFFFAOYSA-N chlorquinaldol Chemical compound ClC1=CC(Cl)=C(O)C2=NC(C)=CC=C21 GPTXWRGISTZRIO-UHFFFAOYSA-N 0.000 claims 2
- 101710171326 Peroxidase 28 Proteins 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 32
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- 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
- C09K11/07—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials having chemically interreactive components, e.g. reactive chemiluminescent compositions
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING 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
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
- C12Q1/28—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving peroxidase
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/968—High energy substrates, e.g. fluorescent, chemiluminescent, radioactive
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Luminescent Compositions (AREA)
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| WO1997026245A1 (en) * | 1996-01-16 | 1997-07-24 | Lumigen, Inc. | Compounds, compositions and methods for generating chemiluminescence with phosphatase enzymes |
| US6126870A (en) * | 1997-09-12 | 2000-10-03 | Lumigen, Inc. | Chemiluminescent labeling compounds |
| US6017769A (en) * | 1998-06-17 | 2000-01-25 | Lumigen, Inc. | Non-enzymatic methods of generating chemiluminescence from acridan alkenes |
| US7186568B1 (en) * | 2000-06-26 | 2007-03-06 | Lumigen Inc. | Electrochemiluminescence from acridan compounds |
| EP1322670B1 (en) * | 2000-06-26 | 2005-12-21 | Lumigen, Inc. | Electrochemiluminescence from acridan compounds |
| US6872828B2 (en) * | 2001-12-20 | 2005-03-29 | Lumigen, Inc. | Compounds for generating chemiluminescence with a peroxidase |
| EP1456176B1 (en) * | 2001-12-20 | 2009-03-18 | Lumigen, Inc. | Improved compounds for generating chemiluminescence with a peroxidase |
| US7560556B2 (en) * | 2001-12-20 | 2009-07-14 | Lumigen, Inc. | Assay methods using chemiluminescent detection of peroxidase |
| US6897036B2 (en) * | 2002-06-06 | 2005-05-24 | Lumigen, Inc. | Fluorescent detection of peroxidase enzymes |
| US7390670B2 (en) | 2003-02-20 | 2008-06-24 | Lumigen, Inc. | Signalling compounds and methods for detecting hydrogen peroxide |
| US7682839B2 (en) * | 2005-03-14 | 2010-03-23 | Lumigen, Inc. | Methods using novel chemiluminescent labels |
| US20060205094A1 (en) * | 2005-03-14 | 2006-09-14 | Lumigen, Inc. | Methods using novel chemiluminescent labels |
| US7879575B2 (en) * | 2005-04-27 | 2011-02-01 | The Trustees Of The University Of Pennsylvania | Nanostructures that provide a modified nanoenvironment for the enhancement of luminescence |
| WO2006116686A2 (en) * | 2005-04-27 | 2006-11-02 | The Trustees Of The University Of Pennsylvania | Nanostructure enhanced luminescent devices |
| WO2006116687A2 (en) * | 2005-04-27 | 2006-11-02 | The Trustees Of The University Of Pennsylvania | Nanoassays |
| US7566573B2 (en) * | 2005-12-19 | 2009-07-28 | Idexx Laboratories, Inc. | Dual standard curve immunoassay |
| US7732153B2 (en) | 2006-05-09 | 2010-06-08 | Beckman Coulter, Inc. | Nonseparation assay methods |
| US7799534B2 (en) * | 2006-05-09 | 2010-09-21 | Beckman Coulter, Inc. | Nonseparation assay methods |
| US7674629B2 (en) * | 2007-03-15 | 2010-03-09 | Saint Louis University | Method for improving chemiluminescent signal |
| WO2009062027A1 (en) * | 2007-11-07 | 2009-05-14 | Beckman Coulter, Inc. | Nonseparation assay methods using peroxide generating enzymes |
| CN101178402B (zh) * | 2007-12-06 | 2011-08-24 | 武汉赛欣生物技术有限公司 | 聚合酶标记抗体的制备方法 |
| US20090162876A1 (en) * | 2007-12-20 | 2009-06-25 | Abbott Laboratories | Myeloperoxidase assays |
| US8652442B2 (en) | 2008-11-03 | 2014-02-18 | Washington University | Bioluminescence imaging of myeloperoxidase activity in vivo, methods, compositions and apparatuses therefor |
| CN102333885A (zh) | 2009-02-27 | 2012-01-25 | 贝克曼考尔特公司 | 使用选择性信号抑制剂的非分离式测定 |
| US9029092B2 (en) | 2009-02-27 | 2015-05-12 | Beckman Coulter, Inc. | Solution phase homogeneous assays |
| US20110097723A1 (en) * | 2009-09-19 | 2011-04-28 | Qun Liu | Methods and reagents for analyte detection |
| JP6553020B2 (ja) | 2013-03-15 | 2019-07-31 | ジーピービー デット ホールディングス トゥー エルエルシー | アレルギー及び自己免疫疾患に関する診断分析を行うための自動化された免疫分析計システム |
| US9383336B2 (en) | 2014-04-04 | 2016-07-05 | General Electric Company | System and method for flat panel detector gel and blot imaging |
| CN104761584A (zh) * | 2015-02-27 | 2015-07-08 | 北京利德曼生化股份有限公司 | 吖啶酯衍生物及其合成方法和应用 |
| EP3350577B1 (en) * | 2015-09-16 | 2022-02-16 | Global Life Sciences Solutions Germany Gmbh | System and method for flat panel detector gel and blot imaging |
| WO2020012391A1 (en) | 2018-07-13 | 2020-01-16 | 3M Innovative Properties Company | Assay |
| CN112400113B (zh) | 2018-07-13 | 2022-04-15 | 3M创新有限公司 | 特异性结合化学发光测定法 |
| CN113295678B (zh) * | 2021-05-14 | 2022-11-08 | 济南迪曼生物科技有限公司 | 一种电化学发光清洗液 |
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| DE68911633T2 (de) * | 1988-09-30 | 1994-04-07 | Fujirebio Kk | Verfahren zur Bestimmung von Peroxidase-Aktivität unter Verwendung von Chemilumineszenz. |
| EP0422252B1 (en) * | 1989-04-28 | 1995-07-26 | Toray Industries, Inc. | Method for detecting a substance using chemiluminescence |
| DD296503A5 (de) * | 1989-07-13 | 1991-12-05 | �K@�K@������������@�K@�Kk�� | Chemitumineszente zusammensetzungen, chemilumineszenz-verfahren und ihre anwendung in analytischen tests |
| US5324835A (en) * | 1990-03-30 | 1994-06-28 | Biosensor Laboratories Co., Ltd. | Pyridazinoquinoxalinones for use as chemiluminescent agents |
| US5629168A (en) * | 1992-02-10 | 1997-05-13 | British Technology Group Limited | Chemiluminescent enhancers |
| US5552298A (en) * | 1992-10-23 | 1996-09-03 | Lumigen, Inc. | Enzyme-catalyzed chemiluminescence from hydroxyaryl cyclic diacylhydrazide compounds |
| US5512451A (en) * | 1993-04-01 | 1996-04-30 | British Technology Group Limited | Enhancement of chemiluminescent reactions |
| US5593845A (en) * | 1993-05-17 | 1997-01-14 | Lumigen, Inc. | Aryl N-alkylacridancarboxylate derivatives useful for chemiluminescent detection |
| US5670644A (en) * | 1993-05-17 | 1997-09-23 | Lumigen, Inc. | Acridan compounds |
| US5491072A (en) * | 1993-05-17 | 1996-02-13 | Lumigen, Inc. | N-alkylacridan carboxyl derivatives useful for chemiluminescent detection |
| US5523212A (en) * | 1993-05-17 | 1996-06-04 | Lumigen, Inc. | Aryl N-alkylacridanthiocarboxylate derivatives useful for chemiluminescent detection |
| US5723295A (en) * | 1993-05-17 | 1998-03-03 | Lumigen, Inc. | Methods, acridan compounds and kits for producing light |
| DE19548375A1 (de) * | 1995-12-27 | 1997-07-03 | Behringwerke Ag | Immunologische Bestimmungsmethode |
| WO1997026245A1 (en) * | 1996-01-16 | 1997-07-24 | Lumigen, Inc. | Compounds, compositions and methods for generating chemiluminescence with phosphatase enzymes |
| ATE364629T1 (de) * | 1996-01-22 | 2007-07-15 | Curis Inc | Methoden zur herstellung von op-1 morphogen analoge |
-
1997
- 1997-09-12 US US08/928,793 patent/US5922558A/en not_active Expired - Lifetime
-
1998
- 1998-08-12 WO PCT/US1998/015813 patent/WO1999014358A1/en not_active Ceased
- 1998-08-12 AT AT98940778T patent/ATE280241T1/de not_active IP Right Cessation
- 1998-08-12 CA CA2300096A patent/CA2300096C/en not_active Expired - Lifetime
- 1998-08-12 ES ES98940778T patent/ES2230710T3/es not_active Expired - Lifetime
- 1998-08-12 DE DE69827152T patent/DE69827152T2/de not_active Expired - Lifetime
- 1998-08-12 JP JP2000511896A patent/JP4790905B2/ja not_active Expired - Lifetime
- 1998-08-12 EP EP98940778A patent/EP1019525B1/en not_active Expired - Lifetime
- 1998-08-12 AU AU88975/98A patent/AU733086C/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU733086C (en) | 2002-01-03 |
| CA2300096A1 (en) | 1999-03-25 |
| EP1019525B1 (en) | 2004-10-20 |
| ATE280241T1 (de) | 2004-11-15 |
| EP1019525A4 (en) | 2003-01-02 |
| WO1999014358A1 (en) | 1999-03-25 |
| AU8897598A (en) | 1999-04-05 |
| DE69827152T2 (de) | 2006-03-09 |
| JP2001516589A (ja) | 2001-10-02 |
| AU733086B2 (en) | 2001-05-03 |
| CA2300096C (en) | 2010-02-09 |
| DE69827152D1 (de) | 2004-11-25 |
| EP1019525A1 (en) | 2000-07-19 |
| US5922558A (en) | 1999-07-13 |
| JP4790905B2 (ja) | 2011-10-12 |
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