DE68925963D1 - Chemilimineszente 1,2-Dioxetan-Verbindungen - Google Patents

Chemilimineszente 1,2-Dioxetan-Verbindungen

Info

Publication number
DE68925963D1
DE68925963D1 DE68925963T DE68925963T DE68925963D1 DE 68925963 D1 DE68925963 D1 DE 68925963D1 DE 68925963 T DE68925963 T DE 68925963T DE 68925963 T DE68925963 T DE 68925963T DE 68925963 D1 DE68925963 D1 DE 68925963D1
Authority
DE
Germany
Prior art keywords
chemiliminescent
dioxetane compounds
group
dioxetane
compounds
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 - Fee Related
Application number
DE68925963T
Other languages
English (en)
Other versions
DE68925963T2 (de
Inventor
Arthur Paul Schaap
Hashem Akhaven-Tafti
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tropix Inc
Original Assignee
Tropix Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Tropix Inc filed Critical Tropix Inc
Publication of DE68925963D1 publication Critical patent/DE68925963D1/de
Application granted granted Critical
Publication of DE68925963T2 publication Critical patent/DE68925963T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
    • C07C43/1788—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
    • C07F9/6539—Five-membered rings
    • C07F9/6541—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
    • 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
    • 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
    • C07F9/6552—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 six-membered ring
    • C07F9/65522—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 six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • 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
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
    • 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
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Luminescent Compositions (AREA)
  • Polyethers (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
DE68925963T 1988-12-27 1989-12-21 Chemilimineszente 1,2-Dioxetan-Verbindungen Expired - Fee Related DE68925963T2 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US07/289,837 US5616729A (en) 1986-07-17 1988-12-27 Enhanced chemiluminescence from 1,2-dioxetanes through energy transfer to tethered fluorescers

Publications (2)

Publication Number Publication Date
DE68925963D1 true DE68925963D1 (de) 1996-04-18
DE68925963T2 DE68925963T2 (de) 1996-10-24

Family

ID=23113325

Family Applications (2)

Application Number Title Priority Date Filing Date
DE198989123690T Pending DE379716T1 (de) 1988-12-27 1989-12-21 Chemilimineszente 1,2-dioxetan-verbindungen.
DE68925963T Expired - Fee Related DE68925963T2 (de) 1988-12-27 1989-12-21 Chemilimineszente 1,2-Dioxetan-Verbindungen

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DE198989123690T Pending DE379716T1 (de) 1988-12-27 1989-12-21 Chemilimineszente 1,2-dioxetan-verbindungen.

Country Status (9)

Country Link
US (5) US5616729A (de)
EP (1) EP0379716B1 (de)
JP (1) JPH03505739A (de)
AT (1) ATE135353T1 (de)
CA (1) CA2006222C (de)
DE (2) DE379716T1 (de)
ES (1) ES2040682T1 (de)
GR (1) GR910300015T1 (de)
WO (1) WO1990007511A1 (de)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5582980A (en) * 1989-07-17 1996-12-10 Tropix, Inc. Chemiluminescent 1,2-dioxetanes
US6022964A (en) 1989-07-17 2000-02-08 Tropix, Inc. Chemiluminescent 1,2-dioxetanes
DE473984T1 (de) * 1990-09-07 1992-08-13 The Board Of Governors Of Wayne State University, Detroit, Mich., Us 1,2-dioxetan-verbindungen als chemilumineszierende markierungen fuer organische und biologische molekuele.
US5334725A (en) * 1991-05-21 1994-08-02 Eli Lilly And Company 2-aminomethyl-4-exomethylenethiazoline epoxides
US5340716A (en) * 1991-06-20 1994-08-23 Snytex (U.S.A.) Inc. Assay method utilizing photoactivated chemiluminescent label
DK0984282T3 (da) * 1991-05-22 2003-11-17 Dade Behring Marburg Gmbh Partikler med en inkorporeret sammensætning omfattende en kemiluminescerende forbindelse
US5578498A (en) 1991-05-22 1996-11-26 Behringwerke Ag Metal chelate containing compositions for use in chemiluminescent assays
US5785887A (en) * 1992-04-17 1998-07-28 Colgate-Palmolive Company Peroxygen bleach composition
US6002000A (en) * 1992-07-20 1999-12-14 Dade Behring Marburg Gmbh Chemiluminescent compounds and methods of use
JPH07509245A (ja) * 1992-07-20 1995-10-12 デイド・ベーリング・マルブルク・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング 新規化学発光化合物およびその使用方法
JP3464798B2 (ja) * 1992-07-31 2003-11-10 デイド・ベーリング・マルブルク・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング 光活性化化学発光基質
US5773628A (en) * 1994-11-14 1998-06-30 Tropix, Inc. 1,2-dioxetane compounds with haloalkoxy groups, methods preparation and use
WO1997014692A1 (en) * 1995-10-17 1997-04-24 Tropix, Inc. 1,2 chemiluminescent dioxetanes of improved performance
US5679803A (en) * 1995-10-25 1997-10-21 Tropix, Inc. 1,2 chemiluminescent dioxetanes of improved performance
DE19538708A1 (de) * 1995-10-18 1997-04-24 Boehringer Mannheim Gmbh Heterocyclische Dioxetan-Substrate, Verfahren zur Herstellung und Verwendung
US5783381A (en) * 1995-10-19 1998-07-21 Tropix, Inc. Chemiluminescent 1,2-dioxetanes
US6165800A (en) * 1997-05-30 2000-12-26 Bayer Corporation Chemiluminescent energy transfer conjugates and their uses as labels in binding assays
WO1999049831A2 (en) * 1998-03-28 1999-10-07 Martin Vladimir V Amplified fluorescent materials and uses thereof
US6355441B1 (en) * 1998-07-28 2002-03-12 Tropix, Inc. Benzothiazole dioxetanes
US6660529B2 (en) 1998-07-28 2003-12-09 Pe Corporation Heteroaryl substituted benzothiazole dioxetanes
US6555698B1 (en) * 1998-11-17 2003-04-29 Tropix, Inc. Chemiluminescent substrates for neuraminidase, assays for detection of neuraminidase and kits therefor
US6783948B1 (en) 1999-07-30 2004-08-31 Bayer Corporation Chemiluminescent acridinium compounds and analogues thereof as substrates of hydrolytic enzymes
DE60200051T2 (de) * 2001-03-08 2004-07-29 Tosoh Corp., Shinnanyo 1,2-Dioxetanderivate, Lumineszenzreagenzien, Lumineszenzverfahren und Messmethoden
JP2004167306A (ja) * 2002-11-18 2004-06-17 Ict:Kk 排ガス浄化用触媒および排ガス浄化方法
US7390670B2 (en) 2003-02-20 2008-06-24 Lumigen, Inc. Signalling compounds and methods for detecting hydrogen peroxide
US6970240B2 (en) * 2003-03-10 2005-11-29 Applera Corporation Combination reader
US20060079699A1 (en) * 2004-08-27 2006-04-13 Brooks Edwards Intermediate compounds and methods for synthesizing chemiluminescent dioxetane substrates
FR2886292B1 (fr) 2005-05-27 2009-10-16 Quidd Soc Par Actions Simplifiee Biomarqueur a emission luminescente
WO2009142678A1 (en) * 2008-03-27 2009-11-26 Promega Corporatin Protein labeling with cyanobenzothiazole conjugates
WO2009139811A2 (en) * 2008-05-15 2009-11-19 Tianxin Wang Chemiluminescent methods and reagents for analyte detection
WO2010126075A1 (ja) * 2009-04-30 2010-11-04 国立大学法人 東京大学 Ｎｐｐ検出用蛍光プローブ
EP2456887B1 (de) 2009-07-21 2015-11-25 Gen-Probe Incorporated Verfahren und zusammensetzungen für den quantitativen nachweis von nukleinsäuresequenzen in einem erweiterten dynamischen bereich
EP3408349B1 (de) 2016-01-26 2021-03-31 Ramot at Tel-Aviv University Ltd. Chemiluminescente fluorophor-gekoppelte adamantylene-dioxetane sonden als diagnostika oder in-vivo bildgebende sensoren
AU2018317810A1 (en) 2017-08-17 2020-03-19 Novo Nordisk A/S Novel acylated insulin analogues and uses thereof
CN115947946B (zh) * 2022-12-13 2023-11-07 中山大学 一种肾清除型双通道光学纳米探针及其制备方法和应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3720622A (en) * 1970-01-02 1973-03-13 American Cyanamid Co Generation of light from the decomposition of dioxetaneones in the presence of a fluorescer
US4315998A (en) * 1974-06-12 1982-02-16 Research Corporation Polymer-bound photosensitizing catalysts
CA1044639A (en) * 1974-06-12 1978-12-19 Research Corporation Polymer-bound photosensitizing catalysts and photosensitized reactions utilizing same
US5707559A (en) * 1986-07-17 1998-01-13 Tropix, Inc. Chemiluminescent 1,2-dioxetane compounds

Also Published As

Publication number Publication date
CA2006222A1 (en) 1990-06-27
ATE135353T1 (de) 1996-03-15
WO1990007511A1 (en) 1990-07-12
US5438146A (en) 1995-08-01
ES2040682T1 (es) 1993-11-01
JPH03505739A (ja) 1991-12-12
US5616729A (en) 1997-04-01
US5652345A (en) 1997-07-29
CA2006222C (en) 2001-07-03
GR910300015T1 (en) 1991-11-15
EP0379716A1 (de) 1990-08-01
US5698728A (en) 1997-12-16
EP0379716B1 (de) 1996-03-13
US5631353A (en) 1997-05-20
DE379716T1 (de) 1991-05-23
DE68925963T2 (de) 1996-10-24

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