DD297998A5 - Diarylimidazole - Google Patents

Diarylimidazole Download PDF

Info

Publication number: DD297998A5
Authority: DD; German Democratic Republic
Prior art keywords: radical; determination; substance; sample; lower alkyl
Prior art date: 1989-05-31

Application number

DD90341095A

Other languages

German (de)

English (en)

Inventor

Hans-Peter Braun

Ulfert Deneke

Werner Guethlein

Rolf Nagel

Original Assignee

��@��@��k��

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.)

1989-05-31

Filing date

1990-05-29

Publication date

1992-01-30

1990-05-29 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1992-01-30 Publication of DD297998A5 publication Critical patent/DD297998A5/de

Links

239000000126 substance Substances 0.000 claims abstract description 58
238000000034 method Methods 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 15
239000002824 redox indicator Substances 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
102000004420 Creatine Kinase Human genes 0.000 claims description 44
108010042126 Creatine kinase Proteins 0.000 claims description 44
238000012360 testing method Methods 0.000 claims description 44
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 38
150000001875 compounds Chemical class 0.000 claims description 19
PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims description 17
229960004308 acetylcysteine Drugs 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 14
-1 p-dimethylamino-phenyl Chemical group 0.000 claims description 14
239000004615 ingredient Substances 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 9
230000015572 biosynthetic process Effects 0.000 claims description 7
102000003992 Peroxidases Human genes 0.000 claims description 6
108040007629 peroxidase activity proteins Proteins 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
DZFWNZJKBJOGFQ-UHFFFAOYSA-N julolidine Chemical group C1CCC2=CC=CC3=C2N1CCC3 DZFWNZJKBJOGFQ-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims 1
230000008569 process Effects 0.000 abstract description 5
239000003795 chemical substances by application Substances 0.000 abstract description 4
238000002360 preparation method Methods 0.000 abstract description 4
JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
239000003153 chemical reaction reagent Substances 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
239000000969 carrier Substances 0.000 description 19
239000003480 eluent Substances 0.000 description 19
239000000243 solution Substances 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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239000008280 blood Substances 0.000 description 18
238000001514 detection method Methods 0.000 description 18
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
238000002844 melting Methods 0.000 description 16
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
239000007788 liquid Substances 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
230000004913 activation Effects 0.000 description 12
230000000694 effects Effects 0.000 description 12
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PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
239000013078 crystal Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical compound OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 description 10
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 10
239000000463 material Substances 0.000 description 10
239000012071 phase Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 8
238000010992 reflux Methods 0.000 description 8
230000003647 oxidation Effects 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
230000007420 reactivation Effects 0.000 description 7
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229960000583 acetic acid Drugs 0.000 description 6
239000012043 crude product Substances 0.000 description 6
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
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239000002250 absorbent Substances 0.000 description 5
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239000002253 acid Substances 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
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XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
102000057621 Glycerol kinases Human genes 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
210000001124 body fluid Anatomy 0.000 description 4
239000010839 body fluid Substances 0.000 description 4
CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 4
OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
235000011187 glycerol Nutrition 0.000 description 4
239000002808 molecular sieve Substances 0.000 description 4
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
ABXYOVCSAGTJAC-JGWLITMVSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanethial Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=S ABXYOVCSAGTJAC-JGWLITMVSA-N 0.000 description 3
DOZRDZLFLOODMB-UHFFFAOYSA-N 3,5-di-tert-Butyl-4-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1O DOZRDZLFLOODMB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
108010024636 Glutathione Proteins 0.000 description 3
108700016170 Glycerol kinases Proteins 0.000 description 3
AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
230000008859 change Effects 0.000 description 3
125000004663 dialkyl amino group Chemical group 0.000 description 3
125000005594 diketone group Chemical group 0.000 description 3
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239000004744 fabric Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000003365 glass fiber Substances 0.000 description 3
229960003180 glutathione Drugs 0.000 description 3
238000005534 hematocrit Methods 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
125000002883 imidazolyl group Chemical group 0.000 description 3
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BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
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CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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125000003118 aryl group Chemical group 0.000 description 2
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238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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125000004432 carbon atom Chemical group C* 0.000 description 2
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239000006046 creatine Substances 0.000 description 2
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VHJLVAABSRFDPM-ZXZARUISSA-N dithioerythritol Chemical compound SC[C@H](O)[C@H](O)CS VHJLVAABSRFDPM-ZXZARUISSA-N 0.000 description 2
VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
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238000003786 synthesis reaction Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
210000002700 urine Anatomy 0.000 description 2
CBCQTCPKFYFJEU-UHFFFAOYSA-N 1,4-dioxo-1,4-dipentoxybutane-2-sulfonic acid Chemical compound CCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCC CBCQTCPKFYFJEU-UHFFFAOYSA-N 0.000 description 1
VHJLVAABSRFDPM-UHFFFAOYSA-N 1,4-dithiothreitol Chemical compound SCC(O)C(O)CS VHJLVAABSRFDPM-UHFFFAOYSA-N 0.000 description 1
CTUHWNWLWHCUAY-UHFFFAOYSA-N 1-[4-(diethylamino)phenyl]-2-hydroxypropan-1-one Chemical compound CCN(CC)C1=CC=C(C(=O)C(C)O)C=C1 CTUHWNWLWHCUAY-UHFFFAOYSA-N 0.000 description 1
AESPEQHQWZKPEW-UHFFFAOYSA-N 1-[4-(diethylamino)phenyl]propan-1-one Chemical compound CCN(CC)C1=CC=C(C(=O)CC)C=C1 AESPEQHQWZKPEW-UHFFFAOYSA-N 0.000 description 1
AGOURROBDMBTHY-UHFFFAOYSA-N 1-[4-(dipropylamino)phenyl]-2-hydroxypropan-1-one Chemical compound CCCN(CCC)C1=CC=C(C(=O)C(C)O)C=C1 AGOURROBDMBTHY-UHFFFAOYSA-N 0.000 description 1
FMLUDMBUEJLQLK-UHFFFAOYSA-N 1-[4-(dipropylamino)phenyl]propane-1,2-dione Chemical compound CCCN(CCC)C1=CC=C(C(=O)C(C)=O)C=C1 FMLUDMBUEJLQLK-UHFFFAOYSA-N 0.000 description 1
STCBHSHARMAIOM-UHFFFAOYSA-N 1-methyl-1h-imidazol-1-ium;chloride Chemical compound Cl.CN1C=CN=C1 STCBHSHARMAIOM-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 1
GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 1
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HDOZLDYBGNJMMZ-UHFFFAOYSA-N 4-(dipropylamino)benzaldehyde Chemical compound CCCN(CCC)C1=CC=C(C=O)C=C1 HDOZLDYBGNJMMZ-UHFFFAOYSA-N 0.000 description 1
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 1
MINUIJOJCBSNOG-UHFFFAOYSA-N [1-[4-(diethylamino)phenyl]-1-oxopropan-2-yl] acetate Chemical compound CCN(CC)C1=CC=C(C(=O)C(C)OC(C)=O)C=C1 MINUIJOJCBSNOG-UHFFFAOYSA-N 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
LNQVTSROQXJCDD-UHFFFAOYSA-N adenosine monophosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(CO)C(OP(O)(O)=O)C1O LNQVTSROQXJCDD-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
210000000601 blood cell Anatomy 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
JXIDRUSBYYMCON-UHFFFAOYSA-N butan-2-one;heptane Chemical compound CCC(C)=O.CCCCCCC JXIDRUSBYYMCON-UHFFFAOYSA-N 0.000 description 1
238000011088 calibration curve Methods 0.000 description 1
MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
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239000008139 complexing agent Substances 0.000 description 1
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238000006482 condensation reaction Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 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
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
MWEQTWJABOLLOS-UHFFFAOYSA-L disodium;[[[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-oxidophosphoryl] hydrogen phosphate;trihydrate Chemical compound O.O.O.[Na+].[Na+].C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP([O-])(=O)OP(O)([O-])=O)C(O)C1O MWEQTWJABOLLOS-UHFFFAOYSA-L 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
210000003743 erythrocyte Anatomy 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
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238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
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238000005187 foaming Methods 0.000 description 1
239000011888 foil Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
108010054790 glycerol-3-phosphate oxidase Proteins 0.000 description 1
LPTIRUACFKQDHZ-UHFFFAOYSA-N hexadecyl sulfate;hydron Chemical compound CCCCCCCCCCCCCCCCOS(O)(=O)=O LPTIRUACFKQDHZ-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
230000036651 mood Effects 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000008055 phosphate buffer solution Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000002985 plastic film Substances 0.000 description 1
229920006255 plastic film Polymers 0.000 description 1
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239000004417 polycarbonate Substances 0.000 description 1
229920006289 polycarbonate film Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
238000004393 prognosis Methods 0.000 description 1
KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
URLJMZWTXZTZRR-UHFFFAOYSA-N sodium myristyl sulfate Chemical compound CCCCCCCCCCCCCCOS(O)(=O)=O URLJMZWTXZTZRR-UHFFFAOYSA-N 0.000 description 1
229960000776 sodium tetradecyl sulfate Drugs 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000003774 sulfhydryl reagent Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000005496 tempering Methods 0.000 description 1
239000012085 test solution Substances 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000007306 turnover Effects 0.000 description 1
235000019154 vitamin C Nutrition 0.000 description 1
239000011718 vitamin C Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1

Classifications

- 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- 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
- 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
- C12Q1/48—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving transferase
- C12Q1/50—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving transferase involving creatine phosphokinase
- 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)
Zoology (AREA)
Wood Science & Technology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
Microbiology (AREA)
Molecular Biology (AREA)
Analytical Chemistry (AREA)
Biotechnology (AREA)
Physics & Mathematics (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Immunology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Holo Graphy (AREA)
Steroid Compounds (AREA)
Dental Preparations (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD90341095A 1989-05-31 1990-05-29 Diarylimidazole DD297998A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3917677A DE3917677A1 (de)	1989-05-31	1989-05-31	Diarylimidazole

Publications (1)

Publication Number	Publication Date
DD297998A5 true DD297998A5 (de)	1992-01-30

Family

ID=6381742

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90341095A DD297998A5 (de)	1989-05-31	1990-05-29	Diarylimidazole

Country Status (8)

Country	Link
US (1)	US5162200A (fr)
EP (1)	EP0402667B1 (fr)
JP (1)	JPH0747586B2 (fr)
AT (1)	ATE101137T1 (fr)
CA (1)	CA2017146A1 (fr)
DD (1)	DD297998A5 (fr)
DE (2)	DE3917677A1 (fr)
ES (1)	ES2062171T3 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5702955A (en) *	1995-05-22	1997-12-30	Bayer Corporation	Ascorbate resistant detection of hydrogen peroxide

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4089747A (en) *	1976-08-09	1978-05-16	Eastman Kodak Company	Compositions for the detection of hydrogen peroxide
US4547461A (en) *	1983-01-18	1985-10-15	Eastman Kodak Company	Composition, analytical element and method for the quantification of creatine kinase
JPS59193352A (ja) *	1983-04-18	1984-11-01	Fuji Photo Film Co Ltd	分析試薬および多層化学分析要素
DE3411997A1 (de) *	1984-03-31	1985-10-17	Boehringer Mannheim Gmbh, 6800 Mannheim	Neue redox-indikatoren

1989
- 1989-05-31 DE DE3917677A patent/DE3917677A1/de not_active Withdrawn
1990
- 1990-05-18 CA CA002017146A patent/CA2017146A1/fr not_active Abandoned
- 1990-05-23 AT AT90109780T patent/ATE101137T1/de not_active IP Right Cessation
- 1990-05-23 DE DE90109780T patent/DE59004469D1/de not_active Expired - Lifetime
- 1990-05-23 ES ES90109780T patent/ES2062171T3/es not_active Expired - Lifetime
- 1990-05-23 EP EP90109780A patent/EP0402667B1/fr not_active Expired - Lifetime
- 1990-05-28 JP JP2138145A patent/JPH0747586B2/ja not_active Expired - Fee Related
- 1990-05-29 DD DD90341095A patent/DD297998A5/de not_active IP Right Cessation
- 1990-05-30 US US07/530,661 patent/US5162200A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE59004469D1 (de)	1994-03-17
US5162200A (en)	1992-11-10
EP0402667B1 (fr)	1994-02-02
CA2017146A1 (fr)	1990-11-30
ES2062171T3 (es)	1994-12-16
EP0402667A1 (fr)	1990-12-19
ATE101137T1 (de)	1994-02-15
JPH0747586B2 (ja)	1995-05-24
JPH0319699A (ja)	1991-01-28
DE3917677A1 (de)	1990-12-06

Legal Events

Date	Code	Title	Description
1999-04-01	RPI	Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act)
2000-10-12	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
US4665023A (en)	1987-05-12	Imidazole derivatives as redox indicators
DE69132961T2 (de)	2002-09-19	Styrylsubstituierte heteroarylverbindungen, welche egf-rezeptor-tyrosinkinase inhibieren
DE60318888T2 (de)	2009-01-08	Pyrimido 4,5-d pyrimidinderivate mit antikrebswirkung
EP0054689B1 (fr)	1984-08-29	Préparation stabilisée de sels de tétrazolium
DE2166398C3 (de)	1978-06-22	43-Tetrazolo [1,5-a] chinoline und Verfahren zu ihrer Herstellung
EP0167973B1 (fr)	1988-06-22	Indicateurs redox
DE3704359A1 (de)	1988-08-25	Azolhalbaminal-derivate und ihre verwendung als nitrifikationsinhibitoren
EP0402667B1 (fr)	1994-02-02	Diarylimidazoles
EP0256400B1 (fr)	1992-09-23	Dérivés de pyrimidine, leur préparation et médicaments contenant les dérivés
DE3443415C2 (fr)	1988-10-06
DE3926365A1 (de)	1991-02-07	Cycloalkylenazole, verfahren zu deren herstellung, pharmazeutische praeparate, die diese enthalten sowie ihre verwendung zur herstellung von arzneimitteln
DE69704329T2 (de)	2001-09-20	N-benzylpiperazinderivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
DE69326111T2 (de)	1999-12-09	Hydantoinderivate, deren Salze und diese enthaltende Maillard-Reaktionsinhibitoren
DE3512629C2 (de)	1995-07-06	s-Triazolo[1,5-a]pyrimidine und Verfahren zu ihrer Herstellung
EP0094080B1 (fr)	1987-09-09	Dérivés de la pyrido(2,1-b)quinazoline
US5274095A (en)	1993-12-28	Diarylimidazoles
DD143608A5 (de)	1980-09-03	Verfahren zur herstellung von 4'-substituierten 2,4-dichlor-alpha-(imidazol-n-ylmethyl)-dibenzylaethern
DE69114644T2 (de)	1996-05-15	4(5)-Imidazole fähig zur Inhibierung von Aromatase.
DE69002340T2 (de)	1993-12-02	Pyrimidin-Derivate, 2-[4-(Alpha-heteroaryl-alpha-aryl-(alpha-alkyl)-methoxy)-butyl)-1-piperazinyl] mit serotoninergischer Wirkung.
DE3301470C2 (fr)	1991-04-11
US4131608A (en)	1978-12-26	Thioethers
DE60114889T2 (de)	2006-07-20	Verfahren zur herstellung von fluconazole und kristallmodifikationen davon
DE2302567B2 (de)	1980-05-29	3-Substituierte Rifamycine, Verfahren zu ihrer Herstellung und therapeutische Zubereitung, die diese Verbindungen enthält
DE202023105298U1 (de)	2023-10-13	System zur Synthese von 6-Aryl-4-(aryliden)-2-arylpyridazin-3-on-Derivaten und zur Durchführung einer antimykobakteriellen Bewertung
DE2301766B2 (de)	1980-02-28	3-substituierte Rifamycine, Verfahren zu ihrer Herstellung und therapeutische Zubereitungen, die diese Verbindungen enthalten