JPH11514006A - ジベンゾジヒドロピリジンカルボン酸エステル類及びそれらの化学ルミネセント分析法への利用 - Google Patents
ジベンゾジヒドロピリジンカルボン酸エステル類及びそれらの化学ルミネセント分析法への利用Info
- Publication number
- JPH11514006A JPH11514006A JP10505881A JP50588198A JPH11514006A JP H11514006 A JPH11514006 A JP H11514006A JP 10505881 A JP10505881 A JP 10505881A JP 50588198 A JP50588198 A JP 50588198A JP H11514006 A JPH11514006 A JP H11514006A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- dibenzodihydropyridine
- substituted
- carboxylate
- 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
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
- C07D221/12—Phenanthridines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- 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
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- 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
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- 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
- Y10S435/975—Kit
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- Biotechnology (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Pyridine Compounds (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.式1又は式2で表されるジベンゾジヒドロピリジンカルボン酸エステル: 式中、R1は、置換アルキル又はシアノであり; R2及びR3は、独立して、水素、アルキル、置換アルキル、アリール又は置換ア リールであり; R4は水素、アルキル、置換アルキル、アリール又は置換アリールであり; R5及びR6は、独立して、アルキル、アルコキシ又は比較的酸化に対して安定な 他の置換基であり; m及びnは0から4の整数であって;ここでm又はnが2以上の場合、R5又はR6は相 互結合していても良く; Zは酸素又は硫黄である。 2.R1がハロアルキル基、特に、トリフルオロメチル基である、請求の範囲第 1項記載のジベンゾジヒドロピリジンカルボン酸エステル。 3.R2がハロアルキル基、特に、トリフルオロメチル基である、請求の範囲第 2項記載のジベンゾジヒドロピリジンカルボン酸エステル。 4.R3が、水素、アルキル、ハロアルキル、フェニル又はハロフェニルである 、請求の範囲第1〜3項の何れか1項に記載のジベンゾジヒドロピリジンカルボ ン酸エステル。 5.R5及びR6が、独立して、メトキシ、クロロ及び/又はフルオロ、及びm及び nが、独立して、0又は1である、請求の範囲第1〜4項の何れか1項に記載のジ ベンゾジヒドロピリジンカルボン酸エステル。 6.Zが酸素である、請求の範囲第1〜5項の何れか1項に記載のジベンゾジ ヒドロピリジンカルボン酸エステル。 7.請求の範囲第1〜6項の何れか1項に記載のジベンゾジヒドロピリジンカ ルボン酸エステルを化学ルミネセント基質として用いた、ペルオキシダーゼ分析 方法。 8.pHが6〜7.5である、請求の範囲第7項記載の方法。 9.フェノール、特にp-フェニルフェノールを促進剤として用いる、請求の範 囲第7項又は第8項に記載の方法。 10.請求の範囲第1〜6項の何れか1項に記載のジベンゾジヒドロピリジンカ ルボン酸エステル、及び任意的に過酸化物、フェノール性促進剤、及び任意的に ペルオキシダーゼを含む、ペルオキシダーゼ活性分析用キット。 11.式3又は4で表されるジベンゾピリジニウム化合物: 式中、R1は置換アルキル、特にハロアルキル、又はシアノであり; R2及びR3は、独立して、水素、アルキル、置換アルキル、特にハロアルキル、 アリール又は置換アリールであり; R4は水素、アルキル、置換アルキル、アリール又は置換アリールであり; R5及びR6は、独立して、アルキル、アルコキシ、ハロゲン又は比較的酸化に対 して安定な他の置換基であり; m及びnは0から4の整数で、m又はnが2以上の場合、R5又はR6は相互結合してい ても良く、好ましくはm及びnの一つ以上が1又は2であり;また Zは酸素又は硫黄である。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP96202022.8 | 1996-07-16 | ||
EP96202022 | 1996-07-16 | ||
PCT/NL1997/000417 WO1998002421A1 (en) | 1996-07-16 | 1997-07-15 | Dibenzodihydropyridinecarboxylic esters and their use in chemiluminescent assay methods |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH11514006A true JPH11514006A (ja) | 1999-11-30 |
JP3338061B2 JP3338061B2 (ja) | 2002-10-28 |
Family
ID=8224199
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50588198A Expired - Fee Related JP3338061B2 (ja) | 1996-07-16 | 1997-07-15 | ジベンゾジヒドロピリジンカルボン酸エステル類及びそれらの化学ルミネセント分析法への利用 |
Country Status (10)
Country | Link |
---|---|
US (1) | US6030803A (ja) |
EP (1) | EP0915851B1 (ja) |
JP (1) | JP3338061B2 (ja) |
AT (1) | ATE214697T1 (ja) |
CA (1) | CA2261032C (ja) |
DE (1) | DE69711188T2 (ja) |
DK (1) | DK0915851T3 (ja) |
ES (1) | ES2171964T3 (ja) |
PT (1) | PT915851E (ja) |
WO (1) | WO1998002421A1 (ja) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3169383B2 (ja) | 1996-01-16 | 2001-05-21 | ルミゲン インク | ホスファターゼ酵素で化学発光を生成させるための化合物、組成物および方法 |
US6410732B2 (en) | 1996-01-16 | 2002-06-25 | Lumigen, Inc. | Processing and synthetic intermediates for preparing N-arylacridancarboxylic acid derivatives |
WO2000009487A1 (en) * | 1998-08-11 | 2000-02-24 | Bayer Corporation | Near infrared chemiluminescent acridinium compounds and uses thereof |
US7186568B1 (en) | 2000-06-26 | 2007-03-06 | Lumigen Inc. | Electrochemiluminescence from acridan compounds |
US6897036B2 (en) * | 2002-06-06 | 2005-05-24 | Lumigen, Inc. | Fluorescent detection of peroxidase enzymes |
US7319041B2 (en) * | 2002-09-27 | 2008-01-15 | Siemens Medical Solutions Diagnostic | Applications of acridinium compounds and derivatives in homogeneous assays |
US7309615B2 (en) * | 2002-09-27 | 2007-12-18 | Siemens Medical Solutions Diagnostic | High quantum yield acridinium compounds and their uses in improving assay sensitivity |
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 |
US8974791B2 (en) | 2007-07-27 | 2015-03-10 | Armagen Technologies, Inc. | Methods and compositions for increasing α-L-iduronidase activity in the CNS |
WO2009062027A1 (en) * | 2007-11-07 | 2009-05-14 | Beckman Coulter, Inc. | Nonseparation assay methods using peroxide generating enzymes |
JP2012519284A (ja) | 2009-02-27 | 2012-08-23 | ベックマン コールター, インコーポレイテッド | 選択的シグナル阻害剤を用いた非分離アッセイ |
JP5844643B2 (ja) * | 2009-02-27 | 2016-01-20 | ベックマン コールター, インコーポレイテッド | 液相ホモジニアスアッセイ |
US20110097723A1 (en) * | 2009-09-19 | 2011-04-28 | Qun Liu | Methods and reagents for analyte detection |
PT2485761T (pt) | 2009-10-09 | 2019-05-30 | Armagen Inc | Métodos e composições para aumentar a atividade da iduronato 2-sulfatase no snc |
WO2012028167A2 (en) | 2010-05-20 | 2012-03-08 | Innohyphen Bv | Acridinium ester chemiluminescence upon reductive triggering |
CN104230804B (zh) * | 2014-08-30 | 2016-05-25 | 云南民族大学 | 化学发光物aps-5关键中间体的制备方法 |
US10538589B2 (en) | 2015-01-14 | 2020-01-21 | Armagen Inc. | Methods and compositions for increasing N-acetylglucosaminidase (NAGLU) activity in the CNS using a fusion antibody comprising an anti-human insulin receptor antibody and NAGLU |
EP3821249B1 (en) | 2018-07-13 | 2022-06-29 | 3M Innovative Properties Company | Specific binding chemiluminescent assay |
JP2021531458A (ja) | 2018-07-13 | 2021-11-18 | スリーエム イノベイティブ プロパティズ カンパニー | アッセイ |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3645292C2 (de) * | 1986-08-22 | 1997-12-11 | Hoechst Ag | Chemilumineszenzimmunoassays und ein Verfahren zu ihrer Herstellung |
NZ227506A (en) * | 1987-12-31 | 1992-06-25 | London Diagnostics Inc | Specific binding assays using chemiluminescent compounds |
US4950613A (en) * | 1988-02-26 | 1990-08-21 | Gen-Probe Incorporated | Proteted chemiluminescent labels |
JP2859451B2 (ja) * | 1991-01-11 | 1999-02-17 | 太平洋セメント株式会社 | N−フルオロピリジニウム塩の製造方法 |
US5491072A (en) * | 1993-05-17 | 1996-02-13 | Lumigen, Inc. | N-alkylacridan carboxyl derivatives useful for chemiluminescent detection |
-
1997
- 1997-07-15 WO PCT/NL1997/000417 patent/WO1998002421A1/en active IP Right Grant
- 1997-07-15 US US09/214,514 patent/US6030803A/en not_active Expired - Lifetime
- 1997-07-15 ES ES97930881T patent/ES2171964T3/es not_active Expired - Lifetime
- 1997-07-15 CA CA002261032A patent/CA2261032C/en not_active Expired - Fee Related
- 1997-07-15 EP EP97930881A patent/EP0915851B1/en not_active Expired - Lifetime
- 1997-07-15 DK DK97930881T patent/DK0915851T3/da active
- 1997-07-15 PT PT97930881T patent/PT915851E/pt unknown
- 1997-07-15 AT AT97930881T patent/ATE214697T1/de active
- 1997-07-15 JP JP50588198A patent/JP3338061B2/ja not_active Expired - Fee Related
- 1997-07-15 DE DE69711188T patent/DE69711188T2/de not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US6030803A (en) | 2000-02-29 |
DK0915851T3 (da) | 2002-04-29 |
JP3338061B2 (ja) | 2002-10-28 |
DE69711188D1 (de) | 2002-04-25 |
CA2261032A1 (en) | 1998-01-22 |
PT915851E (pt) | 2002-09-30 |
DE69711188T2 (de) | 2002-09-05 |
EP0915851A1 (en) | 1999-05-19 |
ATE214697T1 (de) | 2002-04-15 |
EP0915851B1 (en) | 2002-03-20 |
WO1998002421A1 (en) | 1998-01-22 |
CA2261032C (en) | 2003-11-25 |
ES2171964T3 (es) | 2002-09-16 |
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