DE3413693A1 - Fluorierte anilinderivate und ihre verwendung - Google Patents
Fluorierte anilinderivate und ihre verwendungInfo
- Publication number
- DE3413693A1 DE3413693A1 DE19843413693 DE3413693A DE3413693A1 DE 3413693 A1 DE3413693 A1 DE 3413693A1 DE 19843413693 DE19843413693 DE 19843413693 DE 3413693 A DE3413693 A DE 3413693A DE 3413693 A1 DE3413693 A1 DE 3413693A1
- Authority
- DE
- Germany
- Prior art keywords
- fluoro
- carbon atoms
- conh
- single bond
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title description 13
- 238000005859 coupling reaction Methods 0.000 claims abstract description 33
- 230000008878 coupling Effects 0.000 claims abstract description 29
- 238000010168 coupling process Methods 0.000 claims abstract description 29
- 230000001590 oxidative effect Effects 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 4
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 claims description 24
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000005755 formation reaction Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- NECDDBBJVCNJNS-UHFFFAOYSA-N 6-fluoro-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(F)=CC=C21 NECDDBBJVCNJNS-UHFFFAOYSA-N 0.000 claims description 3
- SYKWZKHPWKHRQE-UHFFFAOYSA-N n-[2-(n-ethyl-4-fluoro-3-methylanilino)ethyl]acetamide Chemical compound CC(=O)NCCN(CC)C1=CC=C(F)C(C)=C1 SYKWZKHPWKHRQE-UHFFFAOYSA-N 0.000 claims description 3
- XAJWDQMRNMHAPS-UHFFFAOYSA-N 2-(n-ethyl-4-fluoro-3-methylanilino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CC)C1=CC=C(F)C(C)=C1 XAJWDQMRNMHAPS-UHFFFAOYSA-N 0.000 claims description 2
- KDRFCTLUVUMTGF-UHFFFAOYSA-N 2-(n-ethyl-4-fluoro-3-methylanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(F)C(C)=C1 KDRFCTLUVUMTGF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 102000003992 Peroxidases Human genes 0.000 description 12
- 150000001448 anilines Chemical class 0.000 description 12
- 108040007629 peroxidase activity proteins Proteins 0.000 description 12
- -1 lipid peroxides Chemical class 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 230000008033 biological extinction Effects 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- VTZCLNWLRDQSRY-UHFFFAOYSA-N n-ethyl-4-fluoro-3-methylaniline Chemical compound CCNC1=CC=C(F)C(C)=C1 VTZCLNWLRDQSRY-UHFFFAOYSA-N 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 210000001124 body fluid Anatomy 0.000 description 3
- 239000010839 body fluid Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000007819 coupling partner Substances 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 2
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229920004890 Triton X-100 Polymers 0.000 description 2
- 239000013504 Triton X-100 Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- OTIXUSNHAKOJBX-UHFFFAOYSA-N 1-(aziridin-1-yl)ethanone Chemical compound CC(=O)N1CC1 OTIXUSNHAKOJBX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- LUNFMTSAKGYWAN-UHFFFAOYSA-N 3-(6-fluoro-3,4-dihydro-2h-quinolin-1-yl)propane-1-sulfonic acid Chemical compound FC1=CC=C2N(CCCS(=O)(=O)O)CCCC2=C1 LUNFMTSAKGYWAN-UHFFFAOYSA-N 0.000 description 1
- DDSXIDHLKARTSS-UHFFFAOYSA-N 4-(bromomethyl)benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=C(CBr)C=C1 DDSXIDHLKARTSS-UHFFFAOYSA-N 0.000 description 1
- OTZBTUSMWIXRDK-UHFFFAOYSA-N 4-[(n-ethyl-4-fluoro-3-methylanilino)methyl]benzenesulfonic acid Chemical compound C=1C=C(F)C(C)=CC=1N(CC)CC1=CC=C(S(O)(=O)=O)C=C1 OTZBTUSMWIXRDK-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 102000003914 Cholinesterases Human genes 0.000 description 1
- 108090000322 Cholinesterases Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108010015776 Glucose oxidase Proteins 0.000 description 1
- 239000004366 Glucose oxidase Substances 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 108010092464 Urate Oxidase Proteins 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- HKNSIVFWRXBWCK-UHFFFAOYSA-N [N].NC1=CC=CC=C1 Chemical compound [N].NC1=CC=CC=C1 HKNSIVFWRXBWCK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229940048961 cholinesterase Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OGBZMQPBYUMNRI-UHFFFAOYSA-N n-(4-fluoro-3-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(F)C(C)=C1 OGBZMQPBYUMNRI-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229960005222 phenazone Drugs 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- DAKAQNVUSAGTRS-UHFFFAOYSA-M sodium;1-bromoethanesulfonate Chemical compound [Na+].CC(Br)S([O-])(=O)=O DAKAQNVUSAGTRS-UHFFFAOYSA-M 0.000 description 1
- HNFOAHXBHLWKNF-UHFFFAOYSA-M sodium;2-bromoethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCBr HNFOAHXBHLWKNF-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
- C12Q1/28—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving peroxidase
-
- 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
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q2326/00—Chromogens for determinations of oxidoreductase enzymes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- General Engineering & Computer Science (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Biophysics (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843413693 DE3413693A1 (de) | 1984-04-11 | 1984-04-11 | Fluorierte anilinderivate und ihre verwendung |
| DE8585104315T DE3572970D1 (en) | 1984-04-11 | 1985-04-10 | Fluorinated aniline derivatives and their use |
| AT85104315T ATE46324T1 (de) | 1984-04-11 | 1985-04-10 | Fluorierte anilinderivate und ihre verwendung. |
| EP85104315A EP0161482B1 (de) | 1984-04-11 | 1985-04-10 | Fluorierte Anilinderivate und ihre Verwendung |
| JP60075505A JPS60243050A (ja) | 1984-04-11 | 1985-04-11 | フッ素化アニリン誘導体、過酸化水素およびペルオキシダーゼの定量法 |
| US07/159,422 US4912258A (en) | 1984-04-11 | 1988-02-05 | Fluorinated aniline derivatives and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843413693 DE3413693A1 (de) | 1984-04-11 | 1984-04-11 | Fluorierte anilinderivate und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3413693A1 true DE3413693A1 (de) | 1985-10-17 |
Family
ID=6233307
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843413693 Withdrawn DE3413693A1 (de) | 1984-04-11 | 1984-04-11 | Fluorierte anilinderivate und ihre verwendung |
| DE8585104315T Expired DE3572970D1 (en) | 1984-04-11 | 1985-04-10 | Fluorinated aniline derivatives and their use |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8585104315T Expired DE3572970D1 (en) | 1984-04-11 | 1985-04-10 | Fluorinated aniline derivatives and their use |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4912258A (enExample) |
| EP (1) | EP0161482B1 (enExample) |
| JP (1) | JPS60243050A (enExample) |
| AT (1) | ATE46324T1 (enExample) |
| DE (2) | DE3413693A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3425219A1 (de) * | 1984-07-09 | 1986-02-06 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verwendung von anilinderivaten als kupplungskomponente in oxidativen farbbildungsreaktionen |
| JP2701090B2 (ja) * | 1990-11-30 | 1998-01-21 | 和光純薬工業株式会社 | 被酸化性呈色試薬 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3978061A (en) * | 1967-05-16 | 1976-08-31 | L'oreal | Keratin fiber dye compounds |
| LU67861A1 (enExample) * | 1973-06-22 | 1975-03-27 | ||
| NO132225C (enExample) * | 1973-06-22 | 1975-10-08 | Farmaceutisk Ind As | |
| DK678474A (enExample) * | 1974-02-15 | 1975-10-13 | Hoffmann La Roche | |
| IT1070051B (it) * | 1975-06-26 | 1985-03-25 | Oreal | Copulanti per la tintura di fibre cheratiniche..procedimento per la loro preparazione e composizioni di tintura comprendenti tali copulanti |
| FR2315255A1 (fr) * | 1975-06-26 | 1977-01-21 | Oreal | Coupleurs glycoles |
| JPS5823079B2 (ja) * | 1978-11-15 | 1983-05-12 | バテル メモリアル インステイチユ−ト | 水性媒質中の過酸化水素の量および酵素酸化によって過酸化水素を発生する有機基質の量を測定する分析方法および手段 |
| JPS561896A (en) * | 1979-06-19 | 1981-01-10 | Eiken Kagaku Kk | Determination of hydrogen peroxide and reagent for it |
| DE3037342A1 (de) * | 1980-01-09 | 1981-07-16 | Dojindo Laboratories, Kumamotoshi | N-sulfoalkylanilinderivate und ihre verwendung |
| IE50928B1 (en) * | 1980-02-19 | 1986-08-20 | Riker Laboratories Inc | Substituted tetrahydroquinaldines and their use in the preparation of flumequine |
| US4521511A (en) * | 1982-09-22 | 1985-06-04 | Enzyme Technology Company | Catalyzed colorimetric and fluorometric substrates for peroxidase enzyme determinations |
| US4672029A (en) * | 1984-12-06 | 1987-06-09 | Eastman Kodak Company | Color-forming couplers and their use in the analytical determination of hydrogen peroxide or other analytes |
-
1984
- 1984-04-11 DE DE19843413693 patent/DE3413693A1/de not_active Withdrawn
-
1985
- 1985-04-10 DE DE8585104315T patent/DE3572970D1/de not_active Expired
- 1985-04-10 AT AT85104315T patent/ATE46324T1/de not_active IP Right Cessation
- 1985-04-10 EP EP85104315A patent/EP0161482B1/de not_active Expired
- 1985-04-11 JP JP60075505A patent/JPS60243050A/ja active Granted
-
1988
- 1988-02-05 US US07/159,422 patent/US4912258A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0322861B2 (enExample) | 1991-03-27 |
| US4912258A (en) | 1990-03-27 |
| EP0161482B1 (de) | 1989-09-13 |
| EP0161482A1 (de) | 1985-11-21 |
| JPS60243050A (ja) | 1985-12-03 |
| DE3572970D1 (en) | 1989-10-19 |
| ATE46324T1 (de) | 1989-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |