CA2074014A1 - Composes chimiluminescents - Google Patents

Composes chimiluminescents

Info

Publication number: CA2074014A1
Authority: CA; Canada
Prior art keywords: group; chemiluminescent; salt; groups; moiety
Prior art date: 1990-11-21
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.): Abandoned

Application number

CA002074014A

Other languages

English (en)

Inventor

M. Parameswara Reddy

Maged A. Michael

Chan S. Oh

Thomas S. Dobashi

Nabih S. Girgis

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.)

Beckman Coulter Inc

Original Assignee

Beckman Instruments 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.)

1990-11-21

Filing date

1992-07-16

Publication date

1994-01-17

1991-09-20 Priority to EP92900463A priority Critical patent/EP0511366A1/fr

1991-09-20 Priority to PCT/US1991/006861 priority patent/WO1992009580A1/fr

1992-07-16 Application filed by Beckman Instruments Inc filed Critical Beckman Instruments Inc

1992-07-16 Priority to CA002074014A priority patent/CA2074014A1/fr

1994-01-17 Publication of CA2074014A1 publication Critical patent/CA2074014A1/fr

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title abstract description 51
-1 phenanthridinium Chemical compound 0.000 claims abstract description 92
150000003839 salts Chemical class 0.000 claims abstract description 89
229910052799 carbon Inorganic materials 0.000 claims abstract description 42
229910052717 sulfur Inorganic materials 0.000 claims abstract description 29
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
DZBUGLKDJFMEHC-UHFFFAOYSA-O acridine;hydron Chemical compound C1=CC=CC2=CC3=CC=CC=C3[NH+]=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-O 0.000 claims abstract description 20
JEGZRTMZYUDVBF-UHFFFAOYSA-N Benz[a]acridine Chemical group C1=CC=C2C3=CC4=CC=CC=C4N=C3C=CC2=C1 JEGZRTMZYUDVBF-UHFFFAOYSA-N 0.000 claims abstract description 15
SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims abstract description 15
125000001424 substituent group Chemical group 0.000 claims abstract description 13
125000003636 chemical group Chemical group 0.000 claims abstract description 10
125000004429 atom Chemical group 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 75
239000001257 hydrogen Substances 0.000 claims description 69
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical group C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 42
125000003118 aryl group Chemical group 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 31
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 27
150000001450 anions Chemical class 0.000 claims description 25
150000001721 carbon Chemical group 0.000 claims description 23
150000001768 cations Chemical class 0.000 claims description 23
150000002431 hydrogen Chemical class 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 21
125000004093 cyano group Chemical group *C#N 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 18
125000004043 oxo group Chemical group O=* 0.000 claims description 17
125000005518 carboxamido group Chemical group 0.000 claims description 15
125000000623 heterocyclic group Chemical group 0.000 claims description 14
150000003461 sulfonyl halides Chemical class 0.000 claims description 14
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
125000004104 aryloxy group Chemical group 0.000 claims description 12
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 10
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 10
230000015572 biosynthetic process Effects 0.000 claims description 10
150000004820 halides Chemical class 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
150000001451 organic peroxides Chemical class 0.000 claims description 10
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 9
229910052711 selenium Inorganic materials 0.000 claims description 9
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 9
JCNZQXZILSDZLX-UHFFFAOYSA-N 1-(cyanocarbamoylsulfinamoyl)-N-(sulfanylidenemethylidenehydrazinylidene)formamide Chemical compound C(#N)NC(NS(C(=O)N=NN=C=S)=O)=O JCNZQXZILSDZLX-UHFFFAOYSA-N 0.000 claims description 8
BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical group C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 claims description 8
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 8
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
229910002651 NO3 Inorganic materials 0.000 claims description 8
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 8
229910019142 PO4 Inorganic materials 0.000 claims description 8
229910003069 TeO2 Inorganic materials 0.000 claims description 8
125000004414 alkyl thio group Chemical group 0.000 claims description 8
125000001769 aryl amino group Chemical group 0.000 claims description 8
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
229910001882 dioxygen Inorganic materials 0.000 claims description 8
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical group C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
239000010452 phosphate Substances 0.000 claims description 8
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 8
LAJZODKXOMJMPK-UHFFFAOYSA-N tellurium dioxide Chemical compound O=[Te]=O LAJZODKXOMJMPK-UHFFFAOYSA-N 0.000 claims description 8
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 7
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 7
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
125000001931 aliphatic group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 7
229910018162 SeO2 Inorganic materials 0.000 claims description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
IQZPDFORWZTSKT-UHFFFAOYSA-N nitrosulphonic acid Chemical compound OS(=O)(=O)[N+]([O-])=O IQZPDFORWZTSKT-UHFFFAOYSA-N 0.000 claims description 6
239000007800 oxidant agent Substances 0.000 claims description 6
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
GXYLXFITCXXCQV-UHFFFAOYSA-N 10-methylacridin-10-ium Chemical group C1=CC=C2[N+](C)=C(C=CC=C3)C3=CC2=C1 GXYLXFITCXXCQV-UHFFFAOYSA-N 0.000 claims description 4
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
229910052714 tellurium Inorganic materials 0.000 claims description 4
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
150000003536 tetrazoles Chemical class 0.000 claims description 3
150000003852 triazoles Chemical class 0.000 claims description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
150000002780 morpholines Chemical group 0.000 claims description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 6
125000001302 tertiary amino group Chemical group 0.000 claims 1
238000003018 immunoassay Methods 0.000 abstract description 10
238000003556 assay Methods 0.000 abstract description 7
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 5
125000005842 heteroatom Chemical group 0.000 abstract description 5
229910052698 phosphorus Inorganic materials 0.000 abstract description 5
239000011574 phosphorus Substances 0.000 abstract description 5
239000011593 sulfur Substances 0.000 abstract description 5
239000001301 oxygen Substances 0.000 abstract description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
238000002372 labelling Methods 0.000 abstract description 3
238000010348 incorporation Methods 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
CGZITCMVSSNQPE-NAKRPEOUSA-N phytochelatin 2 Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)N[C@H](C(O)=O)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O CGZITCMVSSNQPE-NAKRPEOUSA-N 0.000 description 34
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 23
239000000047 product Substances 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
229940093499 ethyl acetate Drugs 0.000 description 12
235000019439 ethyl acetate Nutrition 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
108090000790 Enzymes Proteins 0.000 description 10
102000004190 Enzymes Human genes 0.000 description 10
MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 10
230000002285 radioactive effect Effects 0.000 description 10
239000007787 solid Substances 0.000 description 10
125000003342 alkenyl group Chemical group 0.000 description 8
125000001309 chloro group Chemical group Cl* 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
125000000304 alkynyl group Chemical group 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
125000005843 halogen group Chemical group 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
102000004169 proteins and genes Human genes 0.000 description 5
108090000623 proteins and genes Proteins 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
230000035945 sensitivity Effects 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 4
230000021615 conjugation Effects 0.000 description 4
125000000392 cycloalkenyl group Chemical group 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
238000003756 stirring Methods 0.000 description 4
229940124530 sulfonamide Drugs 0.000 description 4
150000003456 sulfonamides Chemical class 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000000427 antigen Substances 0.000 description 3
102000036639 antigens Human genes 0.000 description 3
108091007433 antigens Proteins 0.000 description 3
150000001793 charged compounds Chemical class 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
230000007246 mechanism Effects 0.000 description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
238000006862 quantum yield reaction Methods 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
150000007970 thio esters Chemical class 0.000 description 3
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 2
XUVKSPPGPPFPQN-UHFFFAOYSA-N 10-Methyl-9(10H)-acridone Chemical compound C1=CC=C2N(C)C3=CC=CC=C3C(=O)C2=C1 XUVKSPPGPPFPQN-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
XMODVJAZRSKZEF-UHFFFAOYSA-N acridin-9-yl(pyrrol-1-yl)methanone Chemical compound C=12C=CC=CC2=NC2=CC=CC=C2C=1C(=O)N1C=CC=C1 XMODVJAZRSKZEF-UHFFFAOYSA-N 0.000 description 2
150000001251 acridines Chemical class 0.000 description 2
230000004913 activation Effects 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000001514 detection method Methods 0.000 description 2
MKQRDVRSSVPGEB-UHFFFAOYSA-N dioxetan-3-one Chemical compound O=C1COO1 MKQRDVRSSVPGEB-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
230000005284 excitation Effects 0.000 description 2
230000005283 ground state Effects 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000005855 radiation Effects 0.000 description 2
239000011973 solid acid Substances 0.000 description 2
239000012265 solid product Substances 0.000 description 2
241000894007 species Species 0.000 description 2
238000004611 spectroscopical analysis Methods 0.000 description 2
238000010183 spectrum analysis Methods 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
125000003396 thiol group Chemical class [H]S* 0.000 description 2
229920001567 vinyl ester resin Polymers 0.000 description 2
WYNZXNXFHYJUTE-UHFFFAOYSA-N 1,2-dioxetanedione Chemical compound O=C1OOC1=O WYNZXNXFHYJUTE-UHFFFAOYSA-N 0.000 description 1
UUHROEQEJGLJQQ-UHFFFAOYSA-N 1-(10-methylacridin-10-ium-9-carbonyl)indole-2,3-dione Chemical compound C12=CC=CC=C2[N+](C)=C(C=CC=C2)C2=C1C(=O)N1C2=CC=CC=C2C(=O)C1=O UUHROEQEJGLJQQ-UHFFFAOYSA-N 0.000 description 1
MXGJGUFCBPRWPC-UHFFFAOYSA-N 1-(acridine-9-carbonyl)indole-2,3-dione Chemical compound C1=CC=C2C(C(N3C4=CC=CC=C4C(=O)C3=O)=O)=C(C=CC=C3)C3=NC2=C1 MXGJGUFCBPRWPC-UHFFFAOYSA-N 0.000 description 1
HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 description 1
RUYNUXHHUVUINQ-UHFFFAOYSA-N 2-Methyl-3-furanthiol Chemical compound CC=1OC=CC=1S RUYNUXHHUVUINQ-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical compound NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 description 1
HUDPLKWXRLNSPC-UHFFFAOYSA-N 4-aminophthalhydrazide Chemical class O=C1NNC(=O)C=2C1=CC(N)=CC=2 HUDPLKWXRLNSPC-UHFFFAOYSA-N 0.000 description 1
LEOJISUPFSWNMA-UHFFFAOYSA-N ABEI Chemical compound O=C1NNC(=O)C=2C1=CC(N(CCCCN)CC)=CC=2 LEOJISUPFSWNMA-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
241000400611 Eucalyptus deanei Species 0.000 description 1
241001136705 Glechoma hederacea Species 0.000 description 1
229930186217 Glycolipid Natural products 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
108010001336 Horseradish Peroxidase Proteins 0.000 description 1
101100000208 Mus musculus Orm2 gene Proteins 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
108091034117 Oligonucleotide Proteins 0.000 description 1
JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
HQNSZEINMADIMG-UHFFFAOYSA-M [O-]S(F)(=O)=O.C12=CC=CC=C2[N+](C)=C2C=CC=CC2=C1C(=O)N1C=CC=C1 Chemical compound [O-]S(F)(=O)=O.C12=CC=CC=C2[N+](C)=C2C=CC=CC2=C1C(=O)N1C=CC=C1 HQNSZEINMADIMG-UHFFFAOYSA-M 0.000 description 1
ROXGSFNGVZJEOP-UHFFFAOYSA-M [O-]S(F)(=O)=O.C12=CC=CC=C2[N+](C)=C2C=CC=CC2=C1C(=O)N1C=CC=N1 Chemical compound [O-]S(F)(=O)=O.C12=CC=CC=C2[N+](C)=C2C=CC=CC2=C1C(=O)N1C=CC=N1 ROXGSFNGVZJEOP-UHFFFAOYSA-M 0.000 description 1
238000010521 absorption reaction 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
KUKONHWWHFEDCS-UHFFFAOYSA-N acridine-9-carbonyl chloride;hydrochloride Chemical compound Cl.C1=CC=C2C(C(=O)Cl)=C(C=CC=C3)C3=NC2=C1 KUKONHWWHFEDCS-UHFFFAOYSA-N 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
239000005515 coenzyme Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000005274 electronic transitions Effects 0.000 description 1
238000001952 enzyme assay Methods 0.000 description 1
230000005281 excited state Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000000499 gel Substances 0.000 description 1
231100000206 health hazard Toxicity 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
150000003949 imides Chemical group 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
230000000984 immunochemical effect Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000004020 luminiscence type Methods 0.000 description 1
HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
PGWHWYBRRVQFCI-UHFFFAOYSA-N methyl acridine-9-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=C(C=CC=C3)C3=NC2=C1 PGWHWYBRRVQFCI-UHFFFAOYSA-N 0.000 description 1
239000012022 methylating agents‎ Substances 0.000 description 1
108010029942 microperoxidase Proteins 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
238000007899 nucleic acid hybridization Methods 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
150000002926 oxygen Chemical class 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
RXNXLAHQOVLMIE-UHFFFAOYSA-N phenyl 10-methylacridin-10-ium-9-carboxylate Chemical compound C12=CC=CC=C2[N+](C)=C2C=CC=CC2=C1C(=O)OC1=CC=CC=C1 RXNXLAHQOVLMIE-UHFFFAOYSA-N 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
230000008569 process Effects 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000027756 respiratory electron transport chain Effects 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
229940126585 therapeutic drug Drugs 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
229910001428 transition metal ion Inorganic materials 0.000 description 1
125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/64—Acridine or hydrogenated acridine ring systems
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Biomedical Technology (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Cell Biology (AREA)
Microbiology (AREA)
Biotechnology (AREA)
Food Science & Technology (AREA)
Medicinal Chemistry (AREA)
Physics & Mathematics (AREA)
Analytical Chemistry (AREA)
General Physics & Mathematics (AREA)
Pathology (AREA)
Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

CA002074014A 1990-11-21 1992-07-16 Composes chimiluminescents Abandoned CA2074014A1 (fr)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
EP92900463A EP0511366A1 (fr)	1990-11-21	1991-09-20	Composes chimioluminescents
PCT/US1991/006861 WO1992009580A1 (fr)	1990-11-21	1991-09-20	Composes chimioluminescents
CA002074014A CA2074014A1 (fr)	1990-11-21	1992-07-16	Composes chimiluminescents

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US61648690A	1990-11-21	1990-11-21
CA002074014A CA2074014A1 (fr)	1990-11-21	1992-07-16	Composes chimiluminescents

Publications (1)

Publication Number	Publication Date
CA2074014A1 true CA2074014A1 (fr)	1994-01-17

Family

ID=25675333

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002074014A Abandoned CA2074014A1 (fr)	1990-11-21	1992-07-16	Composes chimiluminescents

Country Status (3)

Country	Link
EP (1)	EP0511366A1 (fr)
CA (1)	CA2074014A1 (fr)
WO (1)	WO1992009580A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5731148A (en) *	1995-06-07	1998-03-24	Gen-Probe Incorporated	Adduct protection assay

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE1008216A4 (fr) *	1994-01-25	1996-02-20	Biocode Sa	Derives chemoluminescents heterocycliques.
IT1302564B1 (it) *	1997-05-22	2000-09-29	Hoffmann La Roche	Immunosaggio di polarizzazione di fluorescenza perfezionato.
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
DE60213986T2 (de) *	2001-06-01	2007-09-06	Roche Diagnostics Gmbh	Neuen reagenzien in chemilumineszenz-nachweisverfahren
KR102540846B1 (ko)	2014-11-25	2023-06-07	삼성전자주식회사	유기 광전 소자용 화합물, 및 이를 포함하는 유기 광전 소자, 이미지 센서 및 전자 장치
GB201905721D0 (en)	2019-04-24	2019-06-05	Univ Dundee	Compounds

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1461877A (en) *	1974-02-12	1977-01-19	Wellcome Found	Assay method utilizing chemiluminescence
EP0082636B2 (fr) *	1981-12-11	2006-10-18	The Welsh National School of Medicine	Composés et procédé pour le marquage luminescent
DE3628573C2 (de) *	1986-08-22	1994-10-13	Hoechst Ag	Chemilumineszierende Acridinderivate, Verfahren zu deren Herstellung und ihre Verwendung in Lumineszenzimmunoassays
DE3844954C2 (de) *	1988-02-20	1998-07-16	Hoechst Ag	Spezielle chemilumineszierende Acridinderivate und ihre Verwendung in Lumineszenzimmunoassays

1991
- 1991-09-20 EP EP92900463A patent/EP0511366A1/fr not_active Withdrawn
- 1991-09-20 WO PCT/US1991/006861 patent/WO1992009580A1/fr not_active Ceased
1992
- 1992-07-16 CA CA002074014A patent/CA2074014A1/fr not_active Abandoned

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5731148A (en) *	1995-06-07	1998-03-24	Gen-Probe Incorporated	Adduct protection assay

Also Published As

Publication number	Publication date
EP0511366A1 (fr)	1992-11-04
WO1992009580A1 (fr)	1992-06-11

Publication	Publication Date	Title
US5534622A (en)	1996-07-09	Rare earth cryptates, processes for their preparation, synthesis intermediates and application as fluorescent tracers
US5565570A (en)	1996-10-15	Chemiluminescent acridinium salts
US5521103A (en)	1996-05-28	Acridinium compounds as chemiluminogenic label
CA2768352C (fr)	2016-10-11	Nouveaux colorants fluorescents et leurs utilisations
US4900686A (en)	1990-02-13	Fluorescent conjugates and biological diagnostic assay
CA1137975A (fr)	1982-12-21	Conjugats chimioluminescents marques au phthalhydrazide
GB2045239A (en)	1980-10-29	Intermediates useful in the synthesis of chemiluminescent- labeled conjugates for use in specific binding assays
US5767287A (en)	1998-06-16	Compounds and method for synthesizing sulfoindocyanine dyes
CA2074014A1 (fr)	1994-01-17	Composes chimiluminescents
US4297273A (en)	1981-10-27	Chemiluminescent phthalhydrazide-labeled protein and polypeptide conjugates
CA1147336A (fr)	1983-05-31	Produits conjugues chimilumiscents, marques au phtalhydrazide
CA1147737A (fr)	1983-06-07	Conjugues chimiluminescents marques a la phtalhydrazide

Legal Events

Date	Code	Title	Description
1998-07-16	FZDE	Discontinued

CA2074014A1 - Composes chimiluminescents - Google Patents

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Priority Applications (3)

Applications Claiming Priority (2)

Publications (1)

Family

ID=25675333

Family Applications (1)

Country Status (3)

Cited By (1)

Families Citing this family (6)

Family Cites Families (4)

Cited By (1)

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