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KR900700489A - 희토류 크립테이트, 제조방법, 합성중간물질 및 형광 트레이서로서의 용도 - Google Patents

희토류 크립테이트, 제조방법, 합성중간물질 및 형광 트레이서로서의 용도

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Publication number
KR900700489A
KR900700489A KR1019890701547A KR890701547A KR900700489A KR 900700489 A KR900700489 A KR 900700489A KR 1019890701547 A KR1019890701547 A KR 1019890701547A KR 890701547 A KR890701547 A KR 890701547A KR 900700489 A KR900700489 A KR 900700489A
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South Korea
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formula
cryptate
group
compound
rare earth
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KR1019890701547A
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KR0133732B1 (ko
Inventor
렝 쟝-마리
마띠 제라르
베아뜨리스알파
데쉬노 로베르
졸뤼 에띠엔
Original Assignee
이그레끄, 르 갈릭
꽁빠니 오리 엥뒤스뜨리 소시에떼아노님
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
    • 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
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/531—Production of immunochemical test materials
    • G01N33/532—Production of labelled immunochemicals
    • G01N33/533—Production of labelled immunochemicals with fluorescent label
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2458/00—Labels used in chemical analysis of biological material
    • G01N2458/40—Rare earth chelates

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Immunology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Urology & Nephrology (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Molecular Biology (AREA)
  • Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Cell Biology (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pyridine Compounds (AREA)
  • Luminescent Compositions (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)

Abstract

내용 없음

Description

희토류 크립테이트, 제조방법, 합성중간물질 및 형광 트레이서로서의 용도
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (14)

  1. 하기 일반식 I 및 II중의 하나를 가지는 마크로 폴리시 클리 화합물된 적어도 한개의 희토류 염으로 구성된 희토류 크립테이트 :
    [식에서, 일반식의 고리는 다음 고리중의 하나이다.]
    -Y는 직쇄 또는 측쇄의 한 개 이상의 이중 결합을 함유하거나 하지 않으며 및/또는 산소, 질소, 황 또는 인 같은 한 개 이상의 헤테로원자가 삽입되거나 되지 않는 C1내지 C20알킬렌기, C5내지 C8시클로알킬렌기 또는 C6내지 C14알릴렌기, 상술된 알킬렌, 알킬, 아릴 또는 술포네이트기로 비치환 또는 치환된 시크로알킬렌 또는 아릴렌기에 선택되어진 디발렌트 유기 라디칼로 구성된 스페이서기 또는 팔이다.
    -Z는 생물학적 물질로 공유결합될 수 있는 기능적 기이다, -R은 메틸기이거나 -Y-Z기를 나타낸다, 및-R'은 수소 또는 R''가 C1내지 C10알킬이고 바람직하게는 메틸, 에틸 또는 tert -부틸기를 나타내는 -COOR''기거나 -CO-NH-Y-Z이다.
  2. 제 1항에 있어서, Y가 -CH2-CH2이고 Z가 -NH2-(sic)인 일반식 I의 크립테이트.
  3. 제 1항 또는 제 2항에 있어서,가 비스-비피리딘 마크로사이클인 크립테이트.
  4. 제 1항에 있어서, Y가 -CH2-이고 Z가 CN이며, R이 메틸기인 일반식 II의 크립테이트.
  5. 제 1항에 있어서, Y가 -CH2-CH2-이고 Z가 NH 및 R이 메틸기인 일반식 II의 크립테이트.
  6. 제 1항에 있어서, 하기식 화합물을 다음의, 즉 일반식 NH2-Y-Z의 아민으로 반응하여 아미노 분해시키고 실온에서 질소기류하에 반응을 진행시켜 결과되는 화합물을 이온교환으로 회토류그립테이트로 전환시키는 반응을 거치는 것으로 구성된 일반식 I의 크립테이트로 수득하는 방법.
    [식에서, R1은 C1∼C10알킬렌기이고, Y 및 Z는 제 1항에 정의된 바와 같다.]
  7. 제 6항에 있어서, 식 5의 한분자를 식 6의 화합물 2분자로 반응시켜 일반식 3의 화합물을 수득하고 반응을 용매의 환류온도에서 무수 유기 용매에서 시행하여 일반식 I의 화합물을 수득하는 방법.
    [식에서가 비스-비피리딘 마크로사이클이고 R''는 제 1항에 정의된 바이며, R'는 제 1항에서 정의된 바이고, X는 할라이드 이온이다.]
  8. 제 1항에 있어서, 할로겐화된 화합물9를 마크로사이클로, 마크로폴리시클릭 착화합물 10을 얻기 위해 상술된 용매의 환류 온도에서 및 무수 유기용매의 용액에서 반응시키고 일반식 XYZ의 할로겐화된 화합물로 처리하는 것으로 구성되는 일반식 II의 크립테이트를 얻는 방법.
    [식에서 Y 및 Z는 제 1항에 정의된 바와 같고, X는 할라이드이온이다.]
  9. 합성중간체로서, R1및가 각각 제 1항 및 제 6항에 정의된 바와 같은 다음식의 마크로폴리시클릭 착화합물.
  10. 합성중간체로서,가 제 1항에서 정의된 바와 같고 R2가 H 또는 CH3인 일반식의 화합물.
  11. 제 9항 또는 제 10항에 있어서, 유리크립탄(sic)의 형태인 중간체.
  12. 제 9항 또는 제 10항에 있어서, 알칼리금속 크립테이트 또는 회토류 크립테이트(sic)의 형태인 중간체.
  13. 제 1∼5항중 어느 한 항에 있어서, 형광 잔기로서의 크립테이트의 적용.
  14. 제 1∼5항중 어느 한 항에 있어서, 생물학적물질의 측정 및/또는 결정을 위한 방법 및 특히 균일한 발광방법에서의 형광 잔기로서의 크립테이트의 적용.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890701547A 1987-12-18 1988-12-16 회로류 크립테이트, 제조방법, 합성 중간물질 및 형광 트레이셔로서의 용도 Expired - Fee Related KR0133732B1 (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR87-17765 1987-12-18
FR8717765 1987-12-18
FR8717765A FR2624862B1 (fr) 1987-12-18 1987-12-18 Cryptates de terres rares, procedes d'obtention, intermediaires de synthese et application a titre de marqueurs fluorescents
PCT/FR1988/000620 WO1989005813A1 (fr) 1987-12-18 1988-12-16 Cryptates de terres rares, procedes d'obtention, intermediaires de synthese et application a titre de marqueurs fluorescents

Publications (2)

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KR900700489A true KR900700489A (ko) 1990-08-13
KR0133732B1 KR0133732B1 (ko) 1998-04-21

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EP (1) EP0321353B1 (ko)
JP (1) JP2866419B2 (ko)
KR (1) KR0133732B1 (ko)
AT (1) ATE76410T1 (ko)
AU (1) AU2908889A (ko)
CA (1) CA1334026C (ko)
DE (1) DE3871353D1 (ko)
ES (1) ES2043874T3 (ko)
FI (1) FI92698C (ko)
FR (1) FR2624862B1 (ko)
RU (1) RU2074859C1 (ko)
WO (1) WO1989005813A1 (ko)

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2664702B1 (fr) * 1990-07-13 1993-08-06 Cis Bio Int Procede de reduction d'interferences dans un dosage par fluorescence.
FR2664699B1 (fr) * 1990-07-13 1995-08-18 Cis Bio Int Procede d'amplification du signal d'emission d'un compose luminescent.
EP0626068B1 (en) * 1991-12-05 1999-05-06 Wallac Oy Luminescent lanthanide chelates
FR2769315B1 (fr) * 1997-10-03 2001-06-08 Cis Bio Int Conjugues fluorescents de nucleosides ou de nucleotides, leur procede de preparation et leur utilisation
US6689574B1 (en) 1997-10-07 2004-02-10 Merck & Co., Inc. Assays for nuclear receptor agonists and antagonists using fluorescence resonance energy transfer
FR2778744B1 (fr) 1998-05-14 2000-06-23 Cis Bio Int Dosage immunologique de la chromogranine a humaine (cga) anticorps, reactifs et trousses utilisables pour ce dosage
US6488097B1 (en) 1999-01-08 2002-12-03 Pnm, Inc. Fire protection sprinkler head support
FR2791141B1 (fr) * 1999-03-15 2001-06-01 Cis Bio Int Procede de reduction de l'extinction de fluorescence due au milieu de mesure
FR2792072A1 (fr) * 1999-04-08 2000-10-13 Cis Bio Int Methode homogene de detection ou de determination d'une interaction chimique ou physicochimique
FR2809817B1 (fr) 2000-06-02 2003-08-15 Cis Bio Int Procede de detection de presence d'un liquide dans un melange
FR2810406B1 (fr) * 2000-06-15 2002-09-20 Cis Bio Int Nouveaux cryptates de terre rare peu sensibles a l'extinction de fluorescence
DE102004034517A1 (de) 2004-07-16 2006-02-16 Covion Organic Semiconductors Gmbh Metallkomplexe
FR2878850B1 (fr) 2004-12-02 2008-10-31 Cis Bio Internat Sa Derives de l'inositol-1-phosphate
FR2890446B1 (fr) 2005-09-05 2008-04-18 Cis Bio Internat Sa Methode de detection d'interaction intracellulaire entre bio-molecules
US7845599B2 (en) 2007-03-22 2010-12-07 The Viking Corporation Mounting coupling for sprinkler support system
WO2008155339A2 (en) * 2007-06-20 2008-12-24 Ge Healthcare Limited Labelling methods
FR2934684B1 (fr) 2008-07-31 2012-11-16 Cis Bio Int Methode de detection de l'internalisation de proteines membranaires.
FR2940286B1 (fr) 2008-12-19 2011-04-08 Cis Bio Int Nouveaux cryptates de terres rares comportant un motif tetraazatriphenylene
JP5732452B2 (ja) 2009-04-30 2015-06-10 セイエス ビオ アンテルナショナル Ｖｆｔドメイン膜タンパク質のダイマーを調節する化合物の検出方法
FR2949156B1 (fr) 2009-08-13 2016-04-15 Cis-Bio Int Methode de determination de la liaison d'un compose donne a un recepteur membranaire
FR2977674B1 (fr) 2011-07-06 2015-08-14 Cisbio Bioassays Methode amelioree de detection et/ou de quantification d'un analyte present a la surface d'une cellule
FR2978149B1 (fr) 2011-07-18 2014-01-10 Cisbio Bioassays Nouveaux agents complexants et complexes de lanthanide correspondant, et leur utilisation comme marqueurs luminescents
FR2980271B1 (fr) 2011-09-16 2013-10-11 Cisbio Bioassays Procede de determination de la glycosylation d'un anticorps
WO2013124544A1 (fr) 2012-02-22 2013-08-29 Cisbio Bioassays Procede de normalisation de la luminescence emise par un milieu de mesure.
FR2988174B1 (fr) 2012-03-19 2014-04-25 Cisbio Bioassays Procede de determination de la capacite d'un anticorps a maintenir des cellules a proximite l'une de l'autre
FR3000960B1 (fr) * 2013-01-16 2015-03-06 Cisbio Bioassays Nouveaux agents complexants hydrosolubles et complexes de lanthanide correspondants
FR3004189B1 (fr) 2013-04-04 2015-09-04 Ecole Norm Superieure Lyon Complexes de lanthanide comprenant au moins deux groupes betaines, utiles comme marqueurs luminescents
FR3032797B1 (fr) 2015-02-13 2017-03-03 Cisbio Bioassays Procede de quantification d'une proteine d'interet presente dans un echantillon biologique
FR3045053B1 (fr) 2015-12-09 2018-01-05 Cisbio Bioassays Agents complexants hydrosolubles a base de triazapyridinophane et complexes de lanthanide fluorescents correspondants
WO2017127684A1 (en) 2016-01-21 2017-07-27 SeLux Diagnostics, Inc. Methods for rapid antimicrobial susceptibility testing
US9834808B2 (en) 2016-01-21 2017-12-05 SeLux Diagnostics, Inc. Methods for rapid antibiotic susceptibility testing
CN106432070A (zh) * 2016-09-20 2017-02-22 上海应用技术大学 一种6,6’‑二溴甲基‑2,2’‑联吡啶‑4,4’‑二甲酸二甲酯的制备方法
CN110072888B (zh) 2016-12-16 2023-07-18 H.隆德贝克有限公司 药剂、用途和方法
RU2647578C1 (ru) * 2016-12-20 2018-03-16 Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) N,n’-диэтил- n,n’-ди(2-бром-4-r-фенил)диамиды 2,2’-бипиридил-6,6’-дикарбоновой кислоты и способ их получения, циклизация полученных амидов с образованием 6,6’-диэтил-9,9’-диr-дибензо[f]-1,7-нафтиридин-5,5’(6н,6’h)-дионов
JP7146765B2 (ja) 2016-12-23 2022-10-04 セルックス・ダイアグノスティクス・インコーポレイテッド 改善された迅速な抗菌薬感受性試験のための方法
FR3067349B1 (fr) 2017-06-12 2020-12-04 Cisbio Bioassays Nouveaux agents mono et di-antennes complexants hydrosolubles et complexes de lanthanide correspondants
FR3067712B1 (fr) 2017-06-14 2019-08-02 Cisbio Bioassays Nouveaux agents complexants de type trimethoxyphenyl pyridine hydrosolubles et complexes de lanthanide correspondants
FR3069644B1 (fr) 2017-07-28 2024-07-12 Cisbio Bioassays Methode pour mesurer la modulation de l'activation d'un recepteur couple a une proteine g
ES2898929T3 (es) 2017-12-21 2022-03-09 H Lundbeck As Diagnóstico y tratamiento de alfa-sinucleinopatías
FR3084365B1 (fr) 2018-07-27 2020-10-23 Cisbio Bioassays Anticorps a domaine unique qui se lient a la proteine g alpha
CN109456309B (zh) * 2018-11-22 2020-11-27 北京工业大学 一种多吡唑含氮杂环化合物及其制备和应用
FR3092172B1 (fr) 2019-01-30 2021-02-12 Cisbio Bioassays Méthode pour mesurer la modulation de l’activation d’un récepteur couplé à une protéine G avec des analogues du GTP
CN111848621B (zh) * 2020-06-29 2022-05-27 中国科学院苏州生物医学工程技术研究所 一种镧系笼状化合物及其制备方法与用途

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2570703B1 (fr) * 1984-09-26 1988-07-08 Commissariat Energie Atomique Complexes macropolycycliques de terres rares et application a titre de marqueurs fluorescents

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FR2624862A1 (fr) 1989-06-23
EP0321353B1 (fr) 1992-05-20
FI902981A0 (fi) 1990-06-14
KR0133732B1 (ko) 1998-04-21
JPH03502575A (ja) 1991-06-13
RU2074859C1 (ru) 1997-03-10
FI92698B (fi) 1994-09-15
JP2866419B2 (ja) 1999-03-08
DE3871353D1 (de) 1992-06-25
EP0321353A1 (fr) 1989-06-21
FR2624862B1 (fr) 1990-06-08
ATE76410T1 (de) 1992-06-15
ES2043874T3 (es) 1994-01-01
FI92698C (fi) 1994-12-27
CA1334026C (fr) 1995-01-17
WO1989005813A1 (fr) 1989-06-29
AU2908889A (en) 1989-07-19

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