CS273617B2 - Method of resorufine's derivatives production - Google Patents
Method of resorufine's derivatives production Download PDFInfo
- Publication number
- CS273617B2 CS273617B2 CS549286A CS549286A CS273617B2 CS 273617 B2 CS273617 B2 CS 273617B2 CS 549286 A CS549286 A CS 549286A CS 549286 A CS549286 A CS 549286A CS 273617 B2 CS273617 B2 CS 273617B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- carboxylic acid
- hydroxysuccinimide
- substituted
- amino
- Prior art date
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- HSSLDCABUXLXKM-UHFFFAOYSA-N resorufin Chemical class C1=CC(=O)C=C2OC3=CC(O)=CC=C3N=C21 HSSLDCABUXLXKM-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000003446 ligand Substances 0.000 claims abstract description 70
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 72
- 102000036639 antigens Human genes 0.000 claims description 17
- 108091007433 antigens Proteins 0.000 claims description 17
- 239000000427 antigen Substances 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- OPLMPROXVFNSPN-UHFFFAOYSA-N 3-hydroxy-2,5-dioxopyrrolidine-3-carboxylic acid Chemical group C(=O)(O)C1(C(=O)NC(C1)=O)O OPLMPROXVFNSPN-UHFFFAOYSA-N 0.000 claims 1
- 150000001261 hydroxy acids Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000005518 carboxamido group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 151
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 127
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 80
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 64
- 239000000741 silica gel Substances 0.000 description 63
- 229910002027 silica gel Inorganic materials 0.000 description 63
- 239000002904 solvent Substances 0.000 description 61
- 229960000583 acetic acid Drugs 0.000 description 60
- 239000000047 product Substances 0.000 description 55
- 239000012362 glacial acetic acid Substances 0.000 description 51
- 239000000243 solution Substances 0.000 description 49
- 239000000203 mixture Substances 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- 238000005859 coupling reaction Methods 0.000 description 32
- 230000008878 coupling Effects 0.000 description 29
- 238000010168 coupling process Methods 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 238000003018 immunoassay Methods 0.000 description 16
- 229940027941 immunoglobulin g Drugs 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 15
- -1 antibodies Substances 0.000 description 15
- 239000008057 potassium phosphate buffer Substances 0.000 description 15
- 238000002372 labelling Methods 0.000 description 14
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000000872 buffer Substances 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 11
- AKEUNCKRJATALU-UHFFFAOYSA-N 2,6-dihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=CC=C1O AKEUNCKRJATALU-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 102000004169 proteins and genes Human genes 0.000 description 9
- 108090000623 proteins and genes Proteins 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 239000007850 fluorescent dye Substances 0.000 description 8
- 229960002036 phenytoin Drugs 0.000 description 8
- 230000010287 polarization Effects 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical class [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- 241000283973 Oryctolagus cuniculus Species 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 150000002148 esters Chemical group 0.000 description 6
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 5
- 108010077895 Sarcosine Proteins 0.000 description 5
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000011088 calibration curve Methods 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 5
- 150000002605 large molecules Chemical class 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229940043230 sarcosine Drugs 0.000 description 5
- 239000001119 stannous chloride Substances 0.000 description 5
- 235000011150 stannous chloride Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 4
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 4
- ZYUPLDFSBVJNIH-UHFFFAOYSA-N 3-(1,3-dimethyl-2,6-dioxopurin-7-yl)propanoic acid Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CCC(O)=O)C=N2 ZYUPLDFSBVJNIH-UHFFFAOYSA-N 0.000 description 4
- 102000005744 Glycoside Hydrolases Human genes 0.000 description 4
- 108010031186 Glycoside Hydrolases Proteins 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000002875 fluorescence polarization Methods 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- SIFCHNIAAPMMKG-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) acetate Chemical compound CC(=O)ON1C(=O)CCC1=O SIFCHNIAAPMMKG-UHFFFAOYSA-N 0.000 description 3
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical compound NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 description 3
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 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
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 102000002068 Glycopeptides Human genes 0.000 description 3
- 108010015899 Glycopeptides Proteins 0.000 description 3
- PLXBWHJQWKZRKG-UHFFFAOYSA-N Resazurin Chemical class C1=CC(=O)C=C2OC3=CC(O)=CC=C3[N+]([O-])=C21 PLXBWHJQWKZRKG-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
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- 238000002474 experimental method Methods 0.000 description 3
- 238000001215 fluorescent labelling Methods 0.000 description 3
- 150000004676 glycans Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- ZTSGDCMQRKBJKC-ZDUSSCGKSA-N methyl (2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate Chemical compound IC1=CC(C[C@H](N)C(=O)OC)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 ZTSGDCMQRKBJKC-ZDUSSCGKSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 102000039446 nucleic acids Human genes 0.000 description 3
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- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 3
- 229960002695 phenobarbital Drugs 0.000 description 3
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- MYKMOIQAHCMLIR-UHFFFAOYSA-N tert-butyl 2-(methylamino)acetate Chemical compound CNCC(=O)OC(C)(C)C MYKMOIQAHCMLIR-UHFFFAOYSA-N 0.000 description 3
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 3
- MPLHNVLQVRSVEE-UHFFFAOYSA-N texas red Chemical compound [O-]S(=O)(=O)C1=CC(S(Cl)(=O)=O)=CC=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 MPLHNVLQVRSVEE-UHFFFAOYSA-N 0.000 description 3
- 229940034208 thyroxine Drugs 0.000 description 3
- KUDHATWUNGXIQC-UHFFFAOYSA-N 1-(2-aminoethyl)-5,5-diphenylimidazolidine-2,4-dione Chemical compound NCCN1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 KUDHATWUNGXIQC-UHFFFAOYSA-N 0.000 description 2
- WWOOGWNXZBZSSO-UHFFFAOYSA-N 1-(2-aminoethyl)imidazolidine-2,4-dione Chemical compound NCCN1CC(=O)NC1=O WWOOGWNXZBZSSO-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- WKBLRSUVOPQYMO-UHFFFAOYSA-N 2-methyl-4-nitrosobenzene-1,3-diol Chemical compound CC1=C(O)C=CC(N=O)=C1O WKBLRSUVOPQYMO-UHFFFAOYSA-N 0.000 description 2
- VBIXSHPPIPNDLW-UHFFFAOYSA-N 2-nitrosobenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1N=O VBIXSHPPIPNDLW-UHFFFAOYSA-N 0.000 description 2
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 2
- MFRZPLYKVDHOSN-UHFFFAOYSA-N 4-(2-isocyanoethyl)morpholine Chemical compound [C-]#[N+]CCN1CCOCC1 MFRZPLYKVDHOSN-UHFFFAOYSA-N 0.000 description 2
- JVTXZVVELSONAM-UHFFFAOYSA-N 4-chloro-6-nitrosobenzene-1,3-diol Chemical compound OC1=CC(O)=C(N=O)C=C1Cl JVTXZVVELSONAM-UHFFFAOYSA-N 0.000 description 2
- GUODTJDYAURGDJ-UHFFFAOYSA-N 4-ethyl-6-nitrosobenzene-1,3-diol Chemical compound CCC1=CC(N=O)=C(O)C=C1O GUODTJDYAURGDJ-UHFFFAOYSA-N 0.000 description 2
- CJIJXIFQYOPWTF-UHFFFAOYSA-N 7-hydroxycoumarin Natural products O1C(=O)C=CC2=CC(O)=CC=C21 CJIJXIFQYOPWTF-UHFFFAOYSA-N 0.000 description 2
- ISSGEVVFFNVECI-UHFFFAOYSA-N 9-hydroxy-12-oxido-5-oxobenzo[a]phenoxazin-12-ium-8-carboxylic acid Chemical compound C1=CC=C2C3=[N+]([O-])C(C=CC(O)=C4C(=O)O)=C4OC3=CC(=O)C2=C1 ISSGEVVFFNVECI-UHFFFAOYSA-N 0.000 description 2
- INQHRPGOFLKCNY-UHFFFAOYSA-N 9-hydroxy-8-(piperazine-1-carbonyl)benzo[a]phenoxazin-5-one Chemical compound OC1=CC=C2N=C(C3=CC=CC=C3C(=O)C=3)C=3OC2=C1C(=O)N1CCNCC1 INQHRPGOFLKCNY-UHFFFAOYSA-N 0.000 description 2
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- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000028161 membrane depolarization Effects 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- MZMOYVCDPQCUOP-UHFFFAOYSA-N piperazin-1-ium;2,2,2-trifluoroacetate Chemical compound C1C[NH2+]CCN1.[O-]C(=O)C(F)(F)F MZMOYVCDPQCUOP-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical class OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 239000001022 rhodamine dye Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- FJPYVLNWWICYDW-UHFFFAOYSA-M sodium;5,5-diphenylimidazolidin-1-ide-2,4-dione Chemical compound [Na+].O=C1[N-]C(=O)NC1(C=1C=CC=CC=1)C1=CC=CC=C1 FJPYVLNWWICYDW-UHFFFAOYSA-M 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 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
- 150000007970 thio esters Chemical class 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003021 water soluble solvent Substances 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
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/533—Production of labelled immunochemicals with fluorescent label
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/80—Fluorescent dyes, e.g. rhodamine
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/802—Chromogenic or luminescent peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Medicinal Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Biotechnology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Pathology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS104187A CS273630B2 (en) | 1985-07-25 | 1987-02-17 | Method of resorufine's derivatives production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853526565 DE3526565A1 (de) | 1985-07-25 | 1985-07-25 | Resorufin-derivate, verfahren zu deren herstellung sowie deren verwendung in fluoreszenzimmunoassays |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS549286A2 CS549286A2 (en) | 1990-08-14 |
| CS273617B2 true CS273617B2 (en) | 1991-03-12 |
Family
ID=6276697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS549286A CS273617B2 (en) | 1985-07-25 | 1986-07-18 | Method of resorufine's derivatives production |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US4954630A (es) |
| EP (1) | EP0209875B1 (es) |
| JP (3) | JPS6236368A (es) |
| KR (1) | KR870001184A (es) |
| AT (1) | ATE55998T1 (es) |
| CA (1) | CA1338320C (es) |
| CS (1) | CS273617B2 (es) |
| DE (2) | DE3526565A1 (es) |
| ES (1) | ES2002110A6 (es) |
| SU (1) | SU1621811A3 (es) |
| YU (1) | YU45348B (es) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0319620A1 (en) * | 1987-12-10 | 1989-06-14 | Viomedics Inc. | Novel oxazines-ureas and thiazine urea chromophors |
| DE3526565A1 (de) * | 1985-07-25 | 1987-02-05 | Boehringer Mannheim Gmbh | Resorufin-derivate, verfahren zu deren herstellung sowie deren verwendung in fluoreszenzimmunoassays |
| DE3644401A1 (de) * | 1986-12-24 | 1988-07-07 | Boehringer Mannheim Gmbh | Neue hydrolase-substrate |
| JPH01211595A (ja) * | 1988-02-18 | 1989-08-24 | Kikkoman Corp | 新規Ｎ−アセチル−β−Ｄ−グルコサミン誘導体、その製法及びＮ−アセチル−β−Ｄ−グルコサミニダーゼ活性測定用試薬への利用 |
| AU6351896A (en) * | 1995-07-26 | 1997-02-26 | Universite De Montreal | Elisa serodiagnosis of pig pleuropneumonia serotypes 5a and 5b |
| ES2277376T3 (es) | 1997-04-08 | 2007-07-01 | Universite De Montreal | Serodiagnostico mediante elisa de la pleuroneumonia porcina de serotipo 2. |
| JP3810035B2 (ja) | 1997-09-08 | 2006-08-16 | 日本精機株式会社 | 易開封性包装袋およびその製造装置 |
| US6420130B1 (en) * | 1998-12-14 | 2002-07-16 | Aurora Biosciences Corporation | Optical molecular sensors for cytochrome P450 activity |
| US6143492A (en) * | 1998-12-14 | 2000-11-07 | Aurora Biosciences Corporation | Optical molecular sensors for cytochrome P450 activity |
| ES2199605T3 (es) * | 1998-12-14 | 2004-02-16 | Vertex Pharmaceuticals (San Diego) Llc | Indicadores moleculares opticos de actividad del citocromo p450. |
| US6514687B1 (en) * | 1998-12-14 | 2003-02-04 | Vertex Pharmaceuticals (San Diego), Llc | Optical molecular sensors for cytochrome P450 activity |
| GB9902068D0 (en) * | 1999-01-29 | 1999-03-24 | Smithkline Beecham Plc | Compounds |
| US6727356B1 (en) * | 1999-12-08 | 2004-04-27 | Epoch Pharmaceuticals, Inc. | Fluorescent quenching detection reagents and methods |
| US20040081959A9 (en) * | 1999-12-08 | 2004-04-29 | Epoch Biosciences, Inc. | Fluorescent quenching detection reagents and methods |
| US6972339B2 (en) | 2001-09-07 | 2005-12-06 | Epoch Biosciences, Inc. | Compounds and methods for fluorescent labeling |
| US8569516B2 (en) * | 2001-09-07 | 2013-10-29 | Elitech Holding B.V. | Compounds and methods for fluorescent labeling |
| US7803536B2 (en) * | 2002-09-20 | 2010-09-28 | Integrated Dna Technologies, Inc. | Methods of detecting fluorescence with anthraquinone quencher dyes |
| US7541454B2 (en) * | 2003-10-24 | 2009-06-02 | Epoch Biosciences, Inc. | Compounds and methods for fluorescent labeling |
| EP2298312B1 (en) * | 2003-10-31 | 2018-09-26 | Molecular Probes Inc. | Fluorinated resorufin compounds and their application in detecting hydrogen peroxide |
| US7439341B2 (en) | 2003-11-14 | 2008-10-21 | Integrated Dna Technologies, Inc. | Fluorescence quenching azo dyes, their methods of preparation and use |
| EP1781675B1 (en) | 2004-08-13 | 2014-03-26 | Epoch Biosciences, Inc. | Phosphonate fluorescent dyes and conjugates |
| EP1907560B1 (en) * | 2005-05-20 | 2013-01-23 | Integrated DNA Technologies, Inc. | Compounds and methods for labeling oligonucleotides |
| US9506057B2 (en) | 2010-03-26 | 2016-11-29 | Integrated Dna Technologies, Inc. | Modifications for antisense compounds |
| US8916345B2 (en) | 2010-03-26 | 2014-12-23 | Integrated Dna Technologies, Inc. | Methods for enhancing nucleic acid hybridization |
| US8735575B2 (en) | 2010-07-30 | 2014-05-27 | Washington University | Phenoxazine derivatives and methods of use thereof |
| EP2614149B1 (en) | 2010-09-07 | 2015-04-08 | Integrated Dna Technologies, Inc. | Modifications for antisense compounds |
| DK2714939T3 (en) | 2011-05-24 | 2015-06-29 | Elitech Holding Bv | DETECTION OF METHICILLIN-RESISTENT STAPHYLOCOCCUS AUREUS |
| US20140220598A1 (en) | 2011-09-09 | 2014-08-07 | Tohoku University | Biological substance detection method |
| US9642858B2 (en) | 2012-10-30 | 2017-05-09 | University of Pittsburgh—of the Commonwealth System of Higher Education | Use of resazurin, or analogs thereof, for antibacterial therapy |
| US20140255928A1 (en) | 2013-03-11 | 2014-09-11 | Elitech Holding B.V. | Methods for true isothermal strand displacement amplification |
| WO2014186147A2 (en) | 2013-05-13 | 2014-11-20 | Elitech Holding B.V. | Droplet digital pcr with short minor groove probes |
| EP3230467A1 (en) | 2014-12-12 | 2017-10-18 | ELITechGroup B.V. | Methods and compositions for detecting antibiotic resistant bacteria |
| WO2016094607A2 (en) | 2014-12-12 | 2016-06-16 | Elitechgroup B.V. | Methods and compositions for detecting antibiotic resistant bacteria |
| WO2021080629A1 (en) | 2019-10-23 | 2021-04-29 | Elitechgroup, Inc. | Methods for true isothermal strand displacement amplification |
| EP3932995A1 (en) | 2020-07-04 | 2022-01-05 | Emulseo SAS | Novel fluorescent substrates and uses thereof in microfluidics |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB807687A (en) * | 1955-10-10 | 1959-01-21 | Bayer Ag | Phenoxazone-dicarboxylic acid derivatives |
| US4141688A (en) * | 1977-08-11 | 1979-02-27 | Miles Laboratories, Inc. | Composition, device and method for determining reducing agents |
| IT1140209B (it) * | 1981-09-25 | 1986-09-24 | Anic Spa | Reagenti per immunoluorescenza e metodo per la loro preparazione |
| US4667032A (en) * | 1983-01-21 | 1987-05-19 | Merck Frosst Canada, Inc. | Phenothiazone derivatives and analogs |
| US4859667A (en) * | 1983-01-21 | 1989-08-22 | Merck Frosst Canada, Inc. | Pharmaceutical compositions of phenothiazone derivatives and analogs |
| US4714763A (en) * | 1985-07-11 | 1987-12-22 | Viomedics Inc. | Novel oxazine-ureas and thiazine urea chromophors as fluorescent labels |
| DE3526565A1 (de) * | 1985-07-25 | 1987-02-05 | Boehringer Mannheim Gmbh | Resorufin-derivate, verfahren zu deren herstellung sowie deren verwendung in fluoreszenzimmunoassays |
| DE3526566A1 (de) * | 1985-07-25 | 1987-02-05 | Boehringer Mannheim Gmbh | N-acyl-dihydroresorufin-derivate, verfahren zu deren herstellung sowie deren verwendung zur bestimmung von wasserstoffperoxid, peroxidatisch wirkender verbindungen oder peroxidase |
| DE3644401A1 (de) * | 1986-12-24 | 1988-07-07 | Boehringer Mannheim Gmbh | Neue hydrolase-substrate |
| US5242805A (en) * | 1991-08-23 | 1993-09-07 | Molecular Probes, Inc. | Long wavelength lipophilic fluorogenic glycosidase substrates |
-
1985
- 1985-07-25 DE DE19853526565 patent/DE3526565A1/de not_active Withdrawn
-
1986
- 1986-07-18 CS CS549286A patent/CS273617B2/cs unknown
- 1986-07-21 DE DE8686109957T patent/DE3673715D1/de not_active Expired - Lifetime
- 1986-07-21 YU YU1302/86A patent/YU45348B/xx unknown
- 1986-07-21 EP EP86109957A patent/EP0209875B1/de not_active Expired - Lifetime
- 1986-07-21 AT AT86109957T patent/ATE55998T1/de not_active IP Right Cessation
- 1986-07-24 ES ES8600580A patent/ES2002110A6/es not_active Expired
- 1986-07-24 SU SU864027894A patent/SU1621811A3/ru active
- 1986-07-24 US US06/889,676 patent/US4954630A/en not_active Expired - Lifetime
- 1986-07-24 CA CA000514621A patent/CA1338320C/en not_active Expired - Fee Related
- 1986-07-25 KR KR1019860006078A patent/KR870001184A/ko not_active Withdrawn
- 1986-07-25 JP JP61173993A patent/JPS6236368A/ja active Pending
- 1986-09-05 JP JP61208119A patent/JPS62174066A/ja active Pending
- 1986-09-05 JP JP61208120A patent/JPS62174067A/ja active Pending
-
1991
- 1991-03-28 US US07/758,288 patent/US5304645A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA1338320C (en) | 1996-05-07 |
| YU45348B (en) | 1992-05-28 |
| KR870001184A (ko) | 1987-03-12 |
| EP0209875A1 (de) | 1987-01-28 |
| DE3526565A1 (de) | 1987-02-05 |
| YU130286A (en) | 1987-12-31 |
| ES2002110A6 (es) | 1988-07-16 |
| JPS62174067A (ja) | 1987-07-30 |
| US5304645A (en) | 1994-04-19 |
| JPS62174066A (ja) | 1987-07-30 |
| DE3673715D1 (de) | 1990-10-04 |
| CS549286A2 (en) | 1990-08-14 |
| ATE55998T1 (de) | 1990-09-15 |
| EP0209875B1 (de) | 1990-08-29 |
| JPS6236368A (ja) | 1987-02-17 |
| SU1621811A3 (ru) | 1991-01-15 |
| US4954630A (en) | 1990-09-04 |
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