IL88848A - Immunological determination uses asters, theoesters and amides as myeluminescents - Google Patents

Immunological determination uses asters, theoesters and amides as myeluminescents

Info

Publication number: IL88848A
Authority: IL; Israel
Prior art keywords: specific binding; assay; conjugate; analyte; group
Prior art date: 1987-12-31

Application number

IL8884888A

Other languages

English (en)

Hebrew (he)

Other versions

IL88848A0 (en

Original Assignee

London Diagnostics 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.)

1987-12-31

Filing date

1988-12-30

Publication date

1994-02-27

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26837818&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=IL88848(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1988-12-30 Application filed by London Diagnostics Inc filed Critical London Diagnostics Inc

1989-07-31 Publication of IL88848A0 publication Critical patent/IL88848A0/xx

1994-02-27 Publication of IL88848A publication Critical patent/IL88848A/en

Links

150000002148 esters Chemical class 0.000 title claims abstract description 82
150000001408 amides Chemical class 0.000 title claims abstract description 36
150000007970 thio esters Chemical class 0.000 title claims abstract description 30
238000003018 immunoassay Methods 0.000 title description 5
230000009870 specific binding Effects 0.000 claims abstract description 150
238000000159 protein binding assay Methods 0.000 claims abstract description 85
125000004122 cyclic group Chemical group 0.000 claims abstract description 77
239000000203 mixture Substances 0.000 claims abstract description 65
-1 moiety Chemical class 0.000 claims abstract description 58
229910052799 carbon Inorganic materials 0.000 claims abstract description 47
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 46
125000003118 aryl group Chemical group 0.000 claims abstract description 44
125000001424 substituent group Chemical group 0.000 claims abstract description 29
230000007062 hydrolysis Effects 0.000 claims abstract description 25
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 25
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 19
230000003647 oxidation Effects 0.000 claims abstract description 18
238000007254 oxidation reaction Methods 0.000 claims abstract description 18
125000005842 heteroatom Chemical group 0.000 claims abstract description 16
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
150000002978 peroxides Chemical class 0.000 claims abstract description 16
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 12
229910001882 dioxygen Inorganic materials 0.000 claims abstract description 12
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
238000003149 assay kit Methods 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract 4
238000003556 assay Methods 0.000 claims description 94
238000009739 binding Methods 0.000 claims description 70
239000012491 analyte Substances 0.000 claims description 67
239000000376 reactant Substances 0.000 claims description 64
230000015572 biosynthetic process Effects 0.000 claims description 50
239000007795 chemical reaction product Substances 0.000 claims description 50
239000000463 material Substances 0.000 claims description 32
230000027455 binding Effects 0.000 claims description 24
DZBUGLKDJFMEHC-UHFFFAOYSA-O acridine;hydron Chemical compound C1=CC=CC2=CC3=CC=CC=C3[NH+]=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-O 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
150000001768 cations Chemical class 0.000 claims description 14
230000002829 reductive effect Effects 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 11
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical class [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
239000003153 chemical reaction reagent Substances 0.000 claims description 8
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 7
230000006872 improvement Effects 0.000 claims description 7
230000000903 blocking effect Effects 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 4
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229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 2
150000001413 amino acids Chemical class 0.000 claims description 2
125000005518 carboxamido group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
125000000962 organic group Chemical group 0.000 claims 2
IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 claims 1
101100302211 Arabidopsis thaliana RNR2A gene Proteins 0.000 claims 1
241000182988 Assa Species 0.000 claims 1
101150002896 RNR2 gene Proteins 0.000 claims 1
150000002540 isothiocyanates Chemical class 0.000 claims 1
125000004043 oxo group Chemical group O=* 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
GUOHRXPYGSKUGT-UHFFFAOYSA-N quinolizinium Chemical compound C1=CC=CC2=CC=CC=[N+]21 GUOHRXPYGSKUGT-UHFFFAOYSA-N 0.000 claims 1
229940124530 sulfonamide Drugs 0.000 claims 1
150000003456 sulfonamides Chemical class 0.000 claims 1
125000003396 thiol group Chemical class [H]S* 0.000 claims 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 1
229910052720 vanadium Inorganic materials 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 27
239000007864 aqueous solution Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 63
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
229910001868 water Inorganic materials 0.000 description 54
239000002904 solvent Substances 0.000 description 50
239000000243 solution Substances 0.000 description 49
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 43
239000000872 buffer Substances 0.000 description 43
239000008363 phosphate buffer Substances 0.000 description 43
238000006243 chemical reaction Methods 0.000 description 35
230000000052 comparative effect Effects 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 29
238000000034 method Methods 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
235000019439 ethyl acetate Nutrition 0.000 description 24
239000011780 sodium chloride Substances 0.000 description 24
238000003756 stirring Methods 0.000 description 23
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
239000000523 sample Substances 0.000 description 22
238000001704 evaporation Methods 0.000 description 21
239000007790 solid phase Substances 0.000 description 21
229940093499 ethyl acetate Drugs 0.000 description 20
230000008020 evaporation Effects 0.000 description 18
239000000047 product Substances 0.000 description 18
102000004169 proteins and genes Human genes 0.000 description 18
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239000007787 solid Substances 0.000 description 18
238000001035 drying Methods 0.000 description 16
229910019142 PO4 Inorganic materials 0.000 description 14
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 14
235000021317 phosphate Nutrition 0.000 description 14
239000010452 phosphate Substances 0.000 description 14
238000006467 substitution reaction Methods 0.000 description 14
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 13
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
238000002820 assay format Methods 0.000 description 12
150000001540 azides Chemical class 0.000 description 12
235000011089 carbon dioxide Nutrition 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 12
229940033663 thimerosal Drugs 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
239000000758 substrate Substances 0.000 description 11
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 10
238000004128 high performance liquid chromatography Methods 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
241001494479 Pecora Species 0.000 description 9
FLMOTJBHHJZDED-UHFFFAOYSA-N [O-]S(F)(=O)=O.COC1=CC=C(S(Cl)(=O)=O)C(OC)=C1C1=CC=CC2=[N+](C)C3=CC=CC=C3C(C(O)=O)=C12 Chemical compound [O-]S(F)(=O)=O.COC1=CC=C(S(Cl)(=O)=O)C(OC)=C1C1=CC=CC2=[N+](C)C3=CC=CC=C3C(C(O)=O)=C12 FLMOTJBHHJZDED-UHFFFAOYSA-N 0.000 description 9
UDSISWXADGTTBO-UHFFFAOYSA-N acridine-9-carboxylic acid;sulfurofluoridic acid Chemical compound [O-]S(F)(=O)=O.C1=CC=C2C(C(=O)O)=C(C=CC=C3)C3=[NH+]C2=C1 UDSISWXADGTTBO-UHFFFAOYSA-N 0.000 description 9
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
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FNORUNUDZNWQFF-UHFFFAOYSA-N 2,6-dimethyl-4-nitrophenol Chemical compound CC1=CC([N+]([O-])=O)=CC(C)=C1O FNORUNUDZNWQFF-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
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239000002253 acid Substances 0.000 description 8
150000001721 carbon Chemical group 0.000 description 8
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108091003079 Bovine Serum Albumin Proteins 0.000 description 7
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
229940098773 bovine serum albumin Drugs 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
238000000926 separation method Methods 0.000 description 7
210000002966 serum Anatomy 0.000 description 7
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QOASOGIMYCQJDH-UHFFFAOYSA-N 1-[2,6-dimethyl-4-(trimethylazaniumyl)phenyl]-10-methylacridin-10-ium-9-carboxylate Chemical compound CC1=C(C(=CC(=C1)[N+](C)(C)C)C)C1=CC=CC2=[N+](C3=CC=CC=C3C(=C12)C(=O)[O-])C QOASOGIMYCQJDH-UHFFFAOYSA-N 0.000 description 6
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
OOGYVVYCCYJADG-UHFFFAOYSA-N acridine-1-carboxylic acid Chemical compound C1=CC=C2C=C3C(C(=O)O)=CC=CC3=NC2=C1 OOGYVVYCCYJADG-UHFFFAOYSA-N 0.000 description 6
IYRYQBAAHMBIFT-UHFFFAOYSA-N acridine-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(C=CC=C3)C3=NC2=C1 IYRYQBAAHMBIFT-UHFFFAOYSA-N 0.000 description 6
230000002860 competitive effect Effects 0.000 description 6
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238000005886 esterification reaction Methods 0.000 description 6
238000010265 fast atom bombardment Methods 0.000 description 6
239000011159 matrix material Substances 0.000 description 6
239000012038 nucleophile Substances 0.000 description 6
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QIYUZWMXMSNPRG-UHFFFAOYSA-N phenyl acridine-9-carboxylate Chemical compound C=12C=CC=CC2=NC2=CC=CC=C2C=1C(=O)OC1=CC=CC=C1 QIYUZWMXMSNPRG-UHFFFAOYSA-N 0.000 description 6
229960003387 progesterone Drugs 0.000 description 6
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238000003786 synthesis reaction Methods 0.000 description 6
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ORDIDWMFTSWPSF-UHFFFAOYSA-N 1-(2,6-dimethyl-4-nitrophenyl)acridine-9-carboxylic acid Chemical compound CC1=CC([N+]([O-])=O)=CC(C)=C1C1=CC=CC2=NC3=CC=CC=C3C(C(O)=O)=C12 ORDIDWMFTSWPSF-UHFFFAOYSA-N 0.000 description 5
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 5
KGRKYDOJEWLQMY-UHFFFAOYSA-N 3-hydroxyacridine-9-carboxylic acid Chemical compound OC1=CC=C2C(C(=O)O)=C(C=CC=C3)C3=NC2=C1 KGRKYDOJEWLQMY-UHFFFAOYSA-N 0.000 description 5
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XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 5
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DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
PULIPROXHHEHEY-UHFFFAOYSA-N 1-(2,6-dimethyl-4-nitrophenyl)-10-methyl-9h-acridine Chemical class CN1C2=CC=CC=C2CC2=C1C=CC=C2C1=C(C)C=C([N+]([O-])=O)C=C1C PULIPROXHHEHEY-UHFFFAOYSA-N 0.000 description 4
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IFMDPNYROKZRER-UHFFFAOYSA-N 6-methylphenanthridine Chemical compound C1=CC=C2C(C)=NC3=CC=CC=C3C2=C1 IFMDPNYROKZRER-UHFFFAOYSA-N 0.000 description 4
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WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 4
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BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
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JFZKPIWXUVQQPK-UHFFFAOYSA-N [O-]S(F)(=O)=O.CC1=CC=CC(C)=C1C1=CC=CC2=[N+](C)C3=CC=CC=C3C(C(O)=O)=C12 Chemical compound [O-]S(F)(=O)=O.CC1=CC=CC(C)=C1C1=CC=CC2=[N+](C)C3=CC=CC=C3C(C(O)=O)=C12 JFZKPIWXUVQQPK-UHFFFAOYSA-N 0.000 description 1
MEEOCKXOYJSWTM-UHFFFAOYSA-M [O-]S(F)(=O)=O.COC1=CC=C(S(Cl)(=O)=O)C(OC)=C1OC(=O)C1=CC(C=2C=CC=CC=2)=[N+](C)C2=CC=CC=C12 Chemical compound [O-]S(F)(=O)=O.COC1=CC=C(S(Cl)(=O)=O)C(OC)=C1OC(=O)C1=CC(C=2C=CC=CC=2)=[N+](C)C2=CC=CC=C12 MEEOCKXOYJSWTM-UHFFFAOYSA-M 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
POZJERCVPSQRFG-UHFFFAOYSA-N acridine-9-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=C(C=CC=C3)C3=NC2=C1 POZJERCVPSQRFG-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003418 antiprogestin Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
239000011324 bead Substances 0.000 description 1
JZYMCIPZZLIJKR-UHFFFAOYSA-N benzo[b]acridine Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3N=C21 JZYMCIPZZLIJKR-UHFFFAOYSA-N 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229960002685 biotin Drugs 0.000 description 1
235000020958 biotin Nutrition 0.000 description 1
239000011616 biotin Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
238000010219 correlation analysis Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
POZRVZJJTULAOH-LHZXLZLDSA-N danazol Chemical compound C1[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=CC2=C1C=NO2 POZRVZJJTULAOH-LHZXLZLDSA-N 0.000 description 1
229960000766 danazol Drugs 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
238000002143 fast-atom bombardment mass spectrum Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000004404 heteroalkyl group Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
BTJRKNUKPQBLAL-UHFFFAOYSA-N hydron;4-methylmorpholine;chloride Chemical compound Cl.CN1CCOCC1 BTJRKNUKPQBLAL-UHFFFAOYSA-N 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
230000001900 immune effect Effects 0.000 description 1
230000036046 immunoreaction Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 description 1
238000002372 labelling Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
238000001471 micro-filtration Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
OLSOYUUAJUQDIO-UHFFFAOYSA-N n-isothiocyanato-1-oxomethanimine Chemical compound O=C=NN=C=S OLSOYUUAJUQDIO-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
CCQQDZSUDQGRGI-UHFFFAOYSA-N phenyl 1,3,10-trimethylacridin-10-ium-9-carboxylate Chemical compound C=12C=CC=CC2=[N+](C)C2=CC(C)=CC(C)=C2C=1C(=O)OC1=CC=CC=C1 CCQQDZSUDQGRGI-UHFFFAOYSA-N 0.000 description 1
GAJSTODKNYAPHO-UHFFFAOYSA-N phenyl 2-phenylquinoline-4-carboxylate Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1C(=O)OC1=CC=CC=C1 GAJSTODKNYAPHO-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002028 premature Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000003623 progesteronic effect Effects 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
XSCHRSMBECNVNS-UHFFFAOYSA-O quinoxalin-1-ium Chemical compound [NH+]1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-O 0.000 description 1
230000011514 reflex Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000012488 sample solution Substances 0.000 description 1
238000001542 size-exclusion chromatography Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000003335 steric effect Effects 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000000870 ultraviolet spectroscopy Methods 0.000 description 1
238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
- 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
- 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
- C07D219/06—Oxygen atoms
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
- 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
- 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
- G01N33/536—Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase
- G01N33/542—Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase with steric inhibition or signal modification, e.g. fluorescent quenching
- 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
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Immunology (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Biomedical Technology (AREA)
Hematology (AREA)
Molecular Biology (AREA)
Urology & Nephrology (AREA)
General Health & Medical Sciences (AREA)
Physics & Mathematics (AREA)
Biotechnology (AREA)
Medicinal Chemistry (AREA)
Microbiology (AREA)
Analytical Chemistry (AREA)
Biochemistry (AREA)
Cell Biology (AREA)
General Physics & Mathematics (AREA)
Pathology (AREA)
Food Science & Technology (AREA)
Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Luminescent Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Steroid Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IL8884888A 1987-12-31 1988-12-30 Immunological determination uses asters, theoesters and amides as myeluminescents IL88848A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US14004087A	1987-12-31	1987-12-31
US29184388A	1988-12-29	1988-12-29

Publications (2)

Publication Number	Publication Date
IL88848A0 IL88848A0 (en)	1989-07-31
IL88848A true IL88848A (en)	1994-02-27

Family

ID=26837818

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL8884888A IL88848A (en)	1987-12-31	1988-12-30	Immunological determination uses asters, theoesters and amides as myeluminescents

Country Status (14)

Country	Link
EP (2)	EP0322926B2 (fr)
JP (1)	JP3172522B2 (fr)
KR (1)	KR900700888A (fr)
AT (2)	ATE425970T1 (fr)
AU (1)	AU635890B2 (fr)
CA (1)	CA1341613C (fr)
DE (3)	DE3856597D1 (fr)
ES (1)	ES2134185T5 (fr)
GB (4)	GB2232995B (fr)
GR (1)	GR3031647T3 (fr)
IE (1)	IE61614B1 (fr)
IL (1)	IL88848A (fr)
NZ (1)	NZ227506A (fr)
WO (1)	WO1989006231A1 (fr)

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US4918192A (en) *	1986-10-06	1990-04-17	Ciba Corning Diagnostics Corp.	Polysubstituted aryl acridinium esters
DE3750503T2 (de) *	1986-10-22	1995-02-09	Abbott Lab	Chemilumineszierende Acridinium- und Phenantridiniumsalze.
US4950613A (en) *	1988-02-26	1990-08-21	Gen-Probe Incorporated	Proteted chemiluminescent labels
WO1989012232A1 (fr) *	1988-06-08	1989-12-14	London Diagnostics, Inc.	Analyses mettant en oeuvre la production de signaux detectables induite par activateur
US5656426A (en) *	1988-08-01	1997-08-12	Chiron Diagnostics Corporation	Functionaized hydrophilic acridinium esters
US5227489A (en) *	1988-08-01	1993-07-13	Ciba Corning Diagnostics Corp.	Stable hydrophilic acridinium esters suitable for liposome encapsulation
CA1339491C (fr) *	1988-09-26	1997-10-07	Say-Jong Law	Derives de polysubstitution d'ester d'acridinium arylique, nucleophiles;leurs utilisations
US5663074A (en) *	1988-09-26	1997-09-02	Chiron Diagnostics Corporation	Nucleophilic polysubstituted aryl acridinium ester conjugates and syntheses thereof
US5340716A (en) *	1991-06-20	1994-08-23	Snytex (U.S.A.) Inc.	Assay method utilizing photoactivated chemiluminescent label
WO1994002486A1 (fr) *	1992-07-20	1994-02-03	Syntex (U.S.A.) Inc.	Nouveaux composes chimioluminescents et procedes d'utilisation
US6002000A (en) *	1992-07-20	1999-12-14	Dade Behring Marburg Gmbh	Chemiluminescent compounds and methods of use
CA2141451C (fr) *	1992-07-31	2003-10-07	John S. Pease	Matrices chimioluminescentes pouvant etre photoactivees
JP3584379B2 (ja) *	1993-02-04	2004-11-04	持田製薬株式会社	アクリジニウム化合物およびアクリジニウム化合物複合体
US5395752A (en) *	1993-03-19	1995-03-07	Ciba Corning Diagnostics Corp.	Long emission wavelength chemiluminescent compounds and their use in test assays
US5491072A (en) *	1993-05-17	1996-02-13	Lumigen, Inc.	N-alkylacridan carboxyl derivatives useful for chemiluminescent detection
US5393891A (en) *	1993-06-08	1995-02-28	The Du Pont Merck Pharmaceutical Company	Immunoassay reagents and methods for detecting brequinar and analogs
US5731148A (en) *	1995-06-07	1998-03-24	Gen-Probe Incorporated	Adduct protection assay
EP0761652A1 (fr) *	1995-08-01	1997-03-12	Mochida Pharmaceutical Co., Ltd.	Dérivés d'acridinium à plusieurs groupes luminescents et groupes liants et leur conjugués
PT915851E (pt) *	1996-07-16	2002-09-30	Staat Nl Verteg Door Min Welzi	Esteres dibenzodihidropiridinecarboxilicos e seu uso no ensaio dos metodos quimiluminiscente
US6165800A (en) *	1997-05-30	2000-12-26	Bayer Corporation	Chemiluminescent energy transfer conjugates and their uses as labels in binding assays
JP4838932B2 (ja) *	1997-08-21	2011-12-14	メインメディカルセンター	過酸化物に基づく化学発光の検量方法、並びにそのために用いる化合物
US6723851B2 (en) *	2001-10-31	2004-04-20	Quest Diagnostics Investment Incorporated	Chemiluminescent compounds and use thereof
DE102005020384A1 (de) *	2005-05-02	2006-11-09	Therainvention Gmbh	Spektroskopisches Verfahren zum Nachweis von Analyten

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GB1461877A (en) *	1974-02-12	1977-01-19	Wellcome Found	Assay method utilizing chemiluminescence
DE3279029D1 (en) *	1981-12-11	1988-10-20	Welsh Nat School Med	Luminescent labelling materials and procedures
US4687747A (en) *	1984-07-02	1987-08-18	Mallinckrodt, Inc.	Phenanthridinium ester as a labelling compound in luminometric immunoassay
JPS6261969A (ja) *	1985-09-06	1987-03-18	アモコ・コーポレーション	アクリジニウムエステルの合成法
DE3628573C2 (de) *	1986-08-22	1994-10-13	Hoechst Ag	Chemilumineszierende Acridinderivate, Verfahren zu deren Herstellung und ihre Verwendung in Lumineszenzimmunoassays
US4745181A (en) *	1986-10-06	1988-05-17	Ciba Corning Diagnostics Corp.	Polysubstituted aryl acridinium esters
DE3750503T2 (de) *	1986-10-22	1995-02-09	Abbott Lab	Chemilumineszierende Acridinium- und Phenantridiniumsalze.
DE3854029T2 (de) *	1987-09-21	1995-10-26	Gen Probe Inc	Homogener Abschirmungstest.
NL8703075A (nl) †	1987-12-18	1989-07-17	Nederlanden Staat	Acridiniumverbindingen als chemiluminescentie-merkstof.

1988
- 1988-12-22 NZ NZ227506A patent/NZ227506A/en unknown
- 1988-12-30 GB GB9014479A patent/GB2232995B/en not_active Expired - Lifetime
- 1988-12-30 EP EP88121915A patent/EP0322926B2/fr not_active Expired - Lifetime
- 1988-12-30 AT AT98123411T patent/ATE425970T1/de not_active IP Right Cessation
- 1988-12-30 DE DE3856597T patent/DE3856597D1/de not_active Expired - Lifetime
- 1988-12-30 DE DE3856358T patent/DE3856358T3/de not_active Expired - Lifetime
- 1988-12-30 CA CA587320A patent/CA1341613C/fr active Active
- 1988-12-30 ES ES88121915T patent/ES2134185T5/es not_active Expired - Lifetime
- 1988-12-30 JP JP50138589A patent/JP3172522B2/ja not_active Expired - Lifetime
- 1988-12-30 IE IE389588A patent/IE61614B1/en not_active IP Right Cessation
- 1988-12-30 DE DE883891212T patent/DE3891212T1/de not_active Withdrawn
- 1988-12-30 WO PCT/US1988/004719 patent/WO1989006231A1/fr not_active Ceased
- 1988-12-30 IL IL8884888A patent/IL88848A/en not_active IP Right Cessation
- 1988-12-30 AT AT88121915T patent/ATE183311T1/de not_active IP Right Cessation
- 1988-12-30 AU AU29270/89A patent/AU635890B2/en not_active Expired
- 1988-12-30 EP EP98123411A patent/EP0916658B1/fr not_active Expired - Lifetime
1989
- 1989-09-01 KR KR1019890701647A patent/KR900700888A/ko not_active Withdrawn
1992
- 1992-02-14 GB GB9203180A patent/GB2251942A/en not_active Withdrawn
- 1992-02-14 GB GB9203179A patent/GB2252161A/en not_active Withdrawn
- 1992-02-14 GB GB9203181A patent/GB2252162A/en not_active Withdrawn
1999
- 1999-10-27 GR GR990402736T patent/GR3031647T3/el unknown

Also Published As

Publication number	Publication date
NZ227506A (en)	1992-06-25
ATE425970T1 (de)	2009-04-15
IE883895L (en)	1989-06-30
AU635890B2 (en)	1993-04-08
JPH03501772A (ja)	1991-04-18
EP0916658B1 (fr)	2009-03-18
GB9203181D0 (en)	1992-04-01
GB2232995B (en)	1992-10-14
JP3172522B2 (ja)	2001-06-04
ATE183311T1 (de)	1999-08-15
KR900700888A (ko)	1990-08-17
EP0916658A1 (fr)	1999-05-19
GB2252161A (en)	1992-07-29
DE3856597D1 (de)	2009-04-30
AU2927089A (en)	1989-08-01
DE3856358T3 (de)	2004-12-30
IL88848A0 (en)	1989-07-31
GB2251942A (en)	1992-07-22
GB9203180D0 (en)	1992-04-01
GB2252162A (en)	1992-07-29
EP0322926A2 (fr)	1989-07-05
CA1341613C (fr)	2011-05-10
GB2232995A (en)	1991-01-02
GB9014479D0 (en)	1990-10-03
DE3856358T2 (de)	2000-04-20
ES2134185T5 (es)	2004-11-01
GR3031647T3 (en)	2000-02-29
EP0322926B1 (fr)	1999-08-11
GB9203179D0 (en)	1992-04-01
EP0322926B2 (fr)	2004-03-31
DE3856358D1 (de)	1999-09-16
WO1989006231A1 (fr)	1989-07-13
EP0322926A3 (fr)	1991-03-20
ES2134185T3 (es)	1999-10-01
IE61614B1 (en)	1994-11-16
DE3891212T1 (de)	1991-01-10

Legal Events

Date	Code	Title
2001-06-14	RH	Patent void
2003-03-12	KB	Patent renewed
2007-03-08	KB	Patent renewed

Publication	Publication Date	Title
IL88848A (en)	1994-02-27	Immunological determination uses asters, theoesters and amides as myeluminescents
US5284951A (en)	1994-02-08	Hydrolytically stable chemiluminescent labels and their conjugates, and assays therefrom
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EP0635019B1 (fr)	1999-05-26	Derives opiaces et etiquettes et conjugues de derives opiaces polypeptidiques et proteiques
US5346996A (en)	1994-09-13	Rare earth cryptates, processes for their preparation, synthesis intermediates and application as fluorescent tracers
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US5532171A (en)	1996-07-02	Phenothiazine derivatives, their production and use
Mikola et al.	1995	Syntheses and properties of luminescent lanthanide chelate labels and labeled haptenic antigens for homogeneous immunoassays
GB2045239A (en)	1980-10-29	Intermediates useful in the synthesis of chemiluminescent- labeled conjugates for use in specific binding assays
GB2041920A (en)	1980-09-17	Intermediates useful in the synthesis of chemiluminescent phthalhydrazide-labelled conjugates
JPH07502045A (ja)	1995-03-02	新規なビオチン化試薬
US5338847A (en)	1994-08-16	Hydrolytically stable chemiluminescent labels and their conjugates, and assays therefrom by adduct formation
US4226993A (en)	1980-10-07	Amino-functionalized phthalhydrazides
GB2026158A (en)	1980-01-30	Chemiluminescent naphthalene - 1,2 - dicarboxylic acid hydrazide-labelled conjugates
US5321136A (en)	1994-06-14	Peri substituted fused ring chemiluminescent labels and their conjugates, and assays therefrom
Adamczyk et al.	2000	Evaluation of chemiluminescent estradiol conjugates by using a surface plasmon resonance detector
HK1020276A (en)	2000-04-07	Assays utilizing improved chemiluminescent esters, thioesters and amides
EP0827502A1 (fr)	1998-03-11	Derives de methadone, conjugues de derives de methadone proteiniques et polypeptidiques et marqueurs
US4133949A (en)	1979-01-09	Dicarboxylic acid esters of cardiac glycosides
EP0846126A1 (fr)	1998-06-10	Derives et conjugues d'antidepresseurs tricycliques convenant a des dosages immunologiques
FR2625565A1 (fr)	1989-07-07	Esters, thioesters et amides chimioluminescents perfectionnes, et analyses les utilisant