DD158559A5 - Mittel zum nachweis esterolytischer und/oder proteolytischer enzyme - Google Patents

Mittel zum nachweis esterolytischer und/oder proteolytischer enzyme Download PDF

Info

Publication number: DD158559A5
Authority: DD; German Democratic Republic
Prior art keywords: lower alkyl; group; hydrogen; halogen; lower alkoxy
Prior art date: 1980-05-09

Application number

DD81229847A

Other languages

German (de)

English (en)

Inventor

Dieter Berger

Original Assignee

Boehringer Mannheim Gmbh

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.)

1980-05-09

Filing date

1981-05-08

Publication date

1983-01-19

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6101946&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DD158559(A5) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1981-05-08 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1983-01-19 Publication of DD158559A5 publication Critical patent/DD158559A5/de

Links

108091005804 Peptidases Proteins 0.000 title claims abstract description 30
238000001514 detection method Methods 0.000 title claims abstract description 27
102000035195 Peptidases Human genes 0.000 title claims abstract description 23
229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 title claims abstract description 13
230000000058 esterolytic effect Effects 0.000 title claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 27
125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
239000012954 diazonium Substances 0.000 claims abstract description 26
150000001989 diazonium salts Chemical class 0.000 claims abstract description 26
150000002148 esters Chemical class 0.000 claims abstract description 25
150000001875 compounds Chemical class 0.000 claims abstract description 20
239000004365 Protease Substances 0.000 claims abstract description 17
229910052736 halogen Inorganic materials 0.000 claims abstract description 17
150000002367 halogens Chemical class 0.000 claims abstract description 17
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 17
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 13
108090000371 Esterases Proteins 0.000 claims abstract description 11
150000002431 hydrogen Chemical class 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims abstract description 7
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
239000000470 constituent Substances 0.000 claims abstract description 7
150000001450 anions Chemical class 0.000 claims abstract description 5
230000000087 stabilizing effect Effects 0.000 claims abstract description 5
239000000243 solution Substances 0.000 claims description 51
-1 N-piperidino, phenylamino Chemical group 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 13
239000003153 chemical reaction reagent Substances 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 10
108090000765 processed proteins & peptides Chemical group 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
125000004663 dialkyl amino group Chemical group 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
239000012190 activator Substances 0.000 claims description 8
239000000872 buffer Substances 0.000 claims description 8
239000000654 additive Substances 0.000 claims description 7
150000001413 amino acids Chemical group 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000004104 aryloxy group Chemical group 0.000 claims description 5
239000000843 powder Substances 0.000 claims description 5
230000008878 coupling Effects 0.000 claims description 4
238000010168 coupling process Methods 0.000 claims description 4
238000005859 coupling reaction Methods 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
230000009257 reactivity Effects 0.000 claims description 4
239000003381 stabilizer Substances 0.000 claims description 4
239000000080 wetting agent Substances 0.000 claims description 4
239000002250 absorbent Substances 0.000 claims description 3
230000002745 absorbent Effects 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
239000012085 test solution Substances 0.000 claims description 3
239000010408 film Substances 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
102000004190 Enzymes Human genes 0.000 abstract description 5
108090000790 Enzymes Proteins 0.000 abstract description 5
229940088598 enzyme Drugs 0.000 abstract description 5
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
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230000002452 interceptive effect Effects 0.000 abstract description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 35
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
210000000265 leukocyte Anatomy 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 13
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 12
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 11
239000013078 crystal Substances 0.000 description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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239000000758 substrate Substances 0.000 description 9
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 8
210000002700 urine Anatomy 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
210000001124 body fluid Anatomy 0.000 description 7
239000010839 body fluid Substances 0.000 description 7
ABEUJUYEUCCZQF-UHFFFAOYSA-N 4-chloro-2-methoxy-1-nitrobenzene Chemical compound COC1=CC(Cl)=CC=C1[N+]([O-])=O ABEUJUYEUCCZQF-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000000034 method Methods 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000002904 solvent Substances 0.000 description 6
OBHRVMZSZIDDEK-UHFFFAOYSA-N urobilinogen Chemical compound CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(CC3C(=C(CC)C(=O)N3)C)N2)CCC(O)=O)N1 OBHRVMZSZIDDEK-UHFFFAOYSA-N 0.000 description 6
229940024606 amino acid Drugs 0.000 description 5
235000001014 amino acid Nutrition 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
229940039227 diagnostic agent Drugs 0.000 description 5
239000000032 diagnostic agent Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000005968 1-Decanol Substances 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000001035 drying Methods 0.000 description 4
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
LQXKHFZRJYXXFA-QMMMGPOBSA-N (2s)-2-[(4-methylphenyl)sulfonylamino]propanoic acid Chemical compound OC(=O)[C@H](C)NS(=O)(=O)C1=CC=C(C)C=C1 LQXKHFZRJYXXFA-QMMMGPOBSA-N 0.000 description 3
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
229930195725 Mannitol Natural products 0.000 description 3
BVMWIXWOIGJRGE-UHFFFAOYSA-N NP(O)=O Chemical compound NP(O)=O BVMWIXWOIGJRGE-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910021538 borax Inorganic materials 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000000594 mannitol Substances 0.000 description 3
235000010355 mannitol Nutrition 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000004328 sodium tetraborate Substances 0.000 description 3
235000010339 sodium tetraborate Nutrition 0.000 description 3
ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 2
WKFYEWXSRFQOKX-UHFFFAOYSA-N 1,4-dioxane;toluene Chemical compound C1COCCO1.CC1=CC=CC=C1 WKFYEWXSRFQOKX-UHFFFAOYSA-N 0.000 description 2
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
XQDNFAMOIPNVES-UHFFFAOYSA-N 3,5-Dimethoxyphenol Chemical compound COC1=CC(O)=CC(OC)=C1 XQDNFAMOIPNVES-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 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
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
229960003116 amyl nitrite Drugs 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process 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
239000007853 buffer solution Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000003086 colorant Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
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230000000093 cytochemical effect Effects 0.000 description 2
230000009089 cytolysis Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
238000006911 enzymatic reaction Methods 0.000 description 2
OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 2
238000009472 formulation Methods 0.000 description 2
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
239000000047 product Substances 0.000 description 2
230000002797 proteolythic effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
230000002485 urinary effect Effects 0.000 description 2
239000000811 xylitol Substances 0.000 description 2
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HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 2
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JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
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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 1
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CXHKYNGLOYMSAH-UHFFFAOYSA-N 2-methoxy-4-morpholin-4-ylbenzenediazonium Chemical compound C1=C([N+]#N)C(OC)=CC(N2CCOCC2)=C1 CXHKYNGLOYMSAH-UHFFFAOYSA-N 0.000 description 1
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CPYIJDKLHBGYSY-UHFFFAOYSA-N 3-morpholin-4-yl-4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C(N2CCOCC2)=C1 CPYIJDKLHBGYSY-UHFFFAOYSA-N 0.000 description 1
MGFJDEHFNMWYBD-UHFFFAOYSA-N 4-(2-pyridin-4-ylethenyl)pyridine Chemical group C=1C=NC=CC=1C=CC1=CC=NC=C1 MGFJDEHFNMWYBD-UHFFFAOYSA-N 0.000 description 1
RNMOZCXLJVXTKP-UHFFFAOYSA-N 4-(5-methoxy-2-nitrophenyl)morpholine Chemical compound COC1=CC=C([N+]([O-])=O)C(N2CCOCC2)=C1 RNMOZCXLJVXTKP-UHFFFAOYSA-N 0.000 description 1
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- 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
- C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
- C—CHEMISTRY; METALLURGY
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- 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
- C12Q2334/00—O-linked chromogens for determinations of hydrolase enzymes, e.g. glycosidases, phosphatases, esterases
- C12Q2334/30—Naphthol derivatives, e.g. alpha-naphthyl-esters, i.e. alpha-NE, beta-naphthyl-esters, i.e. beta-NE
- 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
- C12Q2334/00—O-linked chromogens for determinations of hydrolase enzymes, e.g. glycosidases, phosphatases, esterases
- C12Q2334/50—Indoles
- C—CHEMISTRY; METALLURGY
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- 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
- C12Q2334/00—O-linked chromogens for determinations of hydrolase enzymes, e.g. glycosidases, phosphatases, esterases
- C12Q2334/70—O-linked chromogens for determinations of hydrolase enzymes, e.g. glycosidases, phosphatases, esterases the product, e.g. phenol, naphthol being diazotised in situ, e.g. with Fast Red
- 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
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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Zoology (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
General Engineering & Computer Science (AREA)
Microbiology (AREA)
Molecular Biology (AREA)
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Biotechnology (AREA)
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Bioinformatics & Cheminformatics (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Investigating Or Analysing Biological Materials (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Other Investigation Or Analysis Of Materials By Electrical Means (AREA)

DD81229847A 1980-05-09 1981-05-08 Mittel zum nachweis esterolytischer und/oder proteolytischer enzyme DD158559A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19803017721 DE3017721A1 (de)	1980-05-09	1980-05-09	Mittel zum nachweis esterolytischer und/oder proteolytischer enzyme und dafuer geeignete substrate

Publications (1)

Publication Number	Publication Date
DD158559A5 true DD158559A5 (de)	1983-01-19

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ID=6101946

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Application Number	Title	Priority Date	Filing Date
DD81229847A DD158559A5 (de)	1980-05-09	1981-05-08	Mittel zum nachweis esterolytischer und/oder proteolytischer enzyme

Country Status (24)

Country	Link
US (2)	US4551428A (fr)
EP (1)	EP0039880B2 (fr)
JP (2)	JPS578798A (fr)
AR (1)	AR228452A1 (fr)
AT (1)	ATE3993T1 (fr)
AU (1)	AU523744B2 (fr)
BR (1)	BR8102876A (fr)
CA (1)	CA1186201A (fr)
CS (1)	CS223999B2 (fr)
DD (1)	DD158559A5 (fr)
DE (2)	DE3017721A1 (fr)
DK (1)	DK169974B1 (fr)
ES (1)	ES502034A0 (fr)
FI (1)	FI77692C (fr)
HK (1)	HK82586A (fr)
HU (1)	HU187334B (fr)
MY (1)	MY8600605A (fr)
PL (1)	PL131123B1 (fr)
PT (1)	PT73005B (fr)
SG (1)	SG38786G (fr)
SU (1)	SU1466663A3 (fr)
UA (1)	UA6035A1 (fr)
YU (2)	YU117781A (fr)
ZA (1)	ZA812961B (fr)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3017721A1 (de) *	1980-05-09	1981-11-26	Boehringer Mannheim Gmbh, 6800 Mannheim	Mittel zum nachweis esterolytischer und/oder proteolytischer enzyme und dafuer geeignete substrate
US4499185A (en) *	1982-05-17	1985-02-12	Miles Laboratories, Inc.	Test for esterase activity in a liquid sample
DE3309544A1 (de) *	1983-03-17	1984-09-20	Macherey-Nagel & Co Chemikalienhandel, 5160 Düren	Teststreifen zum nachweis von leukozyten im harn
DE3329394A1 (de) *	1983-08-13	1985-02-28	Bayer Ag, 5090 Leverkusen	Chromogene und fluorogene carbonsaeureester, verfahren zu deren herstellung sowie verfahren und mittel zum nachweis und zur bestimmung von hydrolasen
EP0146348B1 (fr) *	1983-12-14	1991-07-31	The Upjohn Company	Naphtalènes, indoles, benzofuranes et benzothiophènes substitués comme inhibiteurs de lipoxygénase
DE3413119A1 (de) *	1984-04-06	1985-10-24	Miles Laboratories, Inc., Elkhart, Ind.	Analysenverfahren und mittel zum nachweis esterolytischer und/oder proteolytischer enzyme
US4637979A (en) *	1984-04-06	1987-01-20	Miles Laboratories, Inc.	Composition and test device for determining the presence of leukocytes containing a zwitterion coupling agent
DE3413118A1 (de) *	1984-04-06	1985-10-24	Miles Laboratories, Inc., Elkhart, Ind.	Analysenverfahren und mittel zum nachweis esterolytischer und/oder proteolytischer enzyme
DE3413077A1 (de) *	1984-04-06	1985-10-17	Miles Laboratories, Inc., Elkhart, Ind.	Chromogene aminosaeure- und peptidester, verfahren zu deren herstellung, verwendung dieser verbindungen in analysenverfahren sowie mittel zum nachweis esterolytischer und/oder proteolytischer enzyme
DE3413120A1 (de) *	1984-04-06	1985-10-24	Miles Laboratories, Inc., Elkhart, Ind.	Analysenverfahren und mittel zum nachweis esterolytischer und/oder proteolytischer enzyme
DE3413078A1 (de) *	1984-04-06	1985-10-24	Miles Laboratories, Inc., Elkhart, Ind.	Chromogene aminosaeure- und peptidester, verfahren zu deren herstellung, verwendung dieser verbindungen in analysenverfahren sowie mittel zum nachweis esterolytischer und/oder proteolytischer enzyme
US4657855A (en) *	1984-04-06	1987-04-14	Miles Laboratories, Inc.	Composition and test device for determining the presence of leukocytes, esterase and protease in a test sample
DE3446714A1 (de) *	1984-12-21	1986-06-26	Boehringer Mannheim Gmbh	Verfahren zum nachweis des vorliegens einer allergie und zum spezifischen nachweis des fuer die allergie verantwortlichen allergens
US4777267A (en) *	1986-02-07	1988-10-11	Kanebo Ltd.	1,3-dioxol-2-one derivatives
US4677075A (en) *	1986-05-05	1987-06-30	Louderback Allan Lee	Urobilinogen control
DE3813503A1 (de) *	1988-04-22	1989-11-02	Boehringer Mannheim Gmbh	Traegergebundenes mehrkomponentiges nachweissystem zur kolorimetrischen bestimmung esterolytisch oder/und proteolytisch aktiver inhaltsstoffe von koerperfluessigkeiten
US5084324A (en) *	1989-08-25	1992-01-28	W. R. Grace & Co.-Conn.	Micro-bubble laminate with perforated substrate
US4950354A (en) *	1989-08-25	1990-08-21	W. R. Grace & Co.-Conn.	Method of making a micro-bubble laminate
JPH0465584U (fr) *	1990-10-12	1992-06-08
EP0661280A1 (fr) *	1993-12-29	1995-07-05	Kyoto Daiichi Kagaku Co., Ltd.	Ester d'acide aminé et composition contenant un réactif pour détecter des leucocytes en elastase dans le liquide corporel
CA2161574A1 (fr)	1994-11-15	1996-05-16	James Noffsinger	Methode pour determiner par colorimetrie la concentration des leucocytes dans un fluide biologique
US6528652B1 (en)	1999-01-21	2003-03-04	Chronimed	Composition and device for detecting leukocytes in urine
US6348324B1 (en)	1999-01-21	2002-02-19	Hypoguard America Limited	Composition and device for detecting leukocytes in urine
US6203496B1 (en) *	1999-08-12	2001-03-20	Michael R. Gael	Apparatus with reagents for detection of medical conditions
IL140993A0 (en)	2000-05-15	2002-02-10	Bayer Ag	Trypsin substrate and diagnostic device, and method of using same
US6955921B2 (en)	2001-04-30	2005-10-18	Bayer Corporation	Trypsin substrate and diagnostic device, and method of using same
US6709868B2 (en) *	2002-05-20	2004-03-23	Portascience Inc.	Method and apparatus for measuring white blood cell count
US7727206B2 (en) *	2005-12-27	2010-06-01	Gorres Geoffrey H	Device for monitoring a patient for a urinary tract infection
US11104933B1 (en) *	2016-03-22	2021-08-31	Cleu Diagnostics, Llc	Compositions and methods for determining the presence of active leukocyte cells using an electrochemical assay
EP3848708A1 (fr) *	2020-01-13	2021-07-14	Roche Diagnostics GmbH	Formulation de réactif pour bande d'essai de leucocytes

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1128371A (en) *	1965-10-04	1968-09-25	Miles Lab	Diagnostic composition
US3585001A (en) *	1969-02-17	1971-06-15	Miles Lab	Stabilized test device and process for detecting couplable compounds
US3715325A (en) *	1970-10-02	1973-02-06	Miles Lab	Insoluble polymeric diazonium salt chromogen
US3905872A (en) *	1973-12-14	1975-09-16	American Cyanamid Co	Alkaline phosphatase test material
DE2531539A1 (de) *	1975-07-15	1977-01-20	Riedel De Haen Ag	Indikatorsubstanz zum nachweis von kuppelnden fluessigkeits-inhaltsstoffen, diese enthaltende diagnostische mittel und verfahren zu deren herstellung
DE2836644A1 (de) *	1978-08-22	1980-03-06	Boehringer Mannheim Gmbh	Diagnostisches mittel zum nachweis von leukozyten in koerperfluessigkeiten und dafuer geeignete chromogene
DE2854987A1 (de) *	1978-12-20	1980-06-26	Boehringer Mannheim Gmbh	Diagnostische mittel zum nachweis proteolytischer enzyme und dafuer geeignete chromogene
DE2905531A1 (de) *	1979-02-14	1981-01-08	Boehringer Mannheim Gmbh	Diagnostisches mittel zum nachweis von leukozyten in koerperfluessigkeiten
DE2936543A1 (de) *	1979-09-10	1981-04-09	Behringwerke Ag, 3550 Marburg	Chromogene verbindungen
DE3017721A1 (de) *	1980-05-09	1981-11-26	Boehringer Mannheim Gmbh, 6800 Mannheim	Mittel zum nachweis esterolytischer und/oder proteolytischer enzyme und dafuer geeignete substrate

1980
- 1980-05-09 DE DE19803017721 patent/DE3017721A1/de not_active Withdrawn
1981
- 1981-05-04 CS CS813290A patent/CS223999B2/cs unknown
- 1981-05-04 AR AR285192A patent/AR228452A1/es active
- 1981-05-05 CA CA000376871A patent/CA1186201A/fr not_active Expired
- 1981-05-05 AT AT81103385T patent/ATE3993T1/de not_active IP Right Cessation
- 1981-05-05 ZA ZA00812961A patent/ZA812961B/xx unknown
- 1981-05-05 EP EP81103385A patent/EP0039880B2/fr not_active Expired
- 1981-05-05 US US06/260,616 patent/US4551428A/en not_active Expired - Lifetime
- 1981-05-05 DE DE8181103385T patent/DE3160522D1/de not_active Expired
- 1981-05-06 PL PL1981231002A patent/PL131123B1/pl unknown
- 1981-05-07 AU AU70239/81A patent/AU523744B2/en not_active Expired
- 1981-05-08 YU YU01177/81A patent/YU117781A/xx unknown
- 1981-05-08 JP JP6927981A patent/JPS578798A/ja active Granted
- 1981-05-08 DD DD81229847A patent/DD158559A5/de not_active IP Right Cessation
- 1981-05-08 PT PT73005A patent/PT73005B/pt unknown
- 1981-05-08 UA UA3278845A patent/UA6035A1/uk unknown
- 1981-05-08 HU HU811244A patent/HU187334B/hu unknown
- 1981-05-08 DK DK204881A patent/DK169974B1/da not_active IP Right Cessation
- 1981-05-08 BR BR8102876A patent/BR8102876A/pt unknown
- 1981-05-08 ES ES502034A patent/ES502034A0/es active Granted
- 1981-05-08 SU SU813278845A patent/SU1466663A3/ru active
- 1981-05-08 FI FI811418A patent/FI77692C/fi not_active IP Right Cessation
1983
- 1983-05-19 YU YU112483A patent/YU45887B/sh unknown
1984
- 1984-05-04 US US06/606,984 patent/US4749648A/en not_active Expired - Lifetime
1985
- 1985-10-11 JP JP60225022A patent/JPS61199800A/ja active Granted
1986
- 1986-04-30 SG SG387/86A patent/SG38786G/en unknown
- 1986-10-30 HK HK825/86A patent/HK82586A/xx not_active IP Right Cessation
- 1986-12-30 MY MY605/86A patent/MY8600605A/xx unknown

Also Published As

Publication number	Publication date
SG38786G (en)	1989-09-01
HK82586A (en)	1986-11-07
YU117781A (en)	1983-12-31
JPS578798A (en)	1982-01-18
JPH0243480B2 (fr)	1990-09-28
JPS6145982B2 (fr)	1986-10-11
AU7023981A (en)	1981-11-12
US4749648A (en)	1988-06-07
ATE3993T1 (de)	1983-07-15
AU523744B2 (en)	1982-08-12
CA1186201A (fr)	1985-04-30
FI77692C (fi)	1989-04-10
MY8600605A (en)	1986-12-31
DE3017721A1 (de)	1981-11-26
AR228452A1 (es)	1983-03-15
PL131123B1 (en)	1984-10-31
CS223999B2 (en)	1983-11-25
FI811418L (fi)	1981-11-10
UA6035A1 (uk)	1994-12-29
EP0039880B1 (fr)	1983-06-29
JPS61199800A (ja)	1986-09-04
PT73005B (de)	1982-07-01
EP0039880A1 (fr)	1981-11-18
ZA812961B (en)	1982-05-26
BR8102876A (pt)	1982-02-02
PT73005A (de)	1981-06-01
YU112483A (en)	1989-10-31
ES8202792A1 (es)	1982-03-01
DK169974B1 (da)	1995-04-18
ES502034A0 (es)	1982-03-01
FI77692B (fi)	1988-12-30
PL231002A1 (fr)	1981-12-23
EP0039880B2 (fr)	1987-06-03
YU45887B (sh)	1992-09-07
SU1466663A3 (ru)	1989-03-15
US4551428A (en)	1985-11-05
DK204881A (da)	1981-11-10
DE3160522D1 (en)	1983-08-04
HU187334B (en)	1985-12-28

Legal Events

Date	Code	Title	Description
1995-08-31	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD158559A5 (de)	1983-01-19	Mittel zum nachweis esterolytischer und/oder proteolytischer enzyme
EP0012957B1 (fr)	1981-09-16	Moyen diagnostique pour la détermination d'enzymes protéolytiques et esters d'indoxyle ou de thioindoxyle appropriés comme chromogènes, procédé pour leur préparation et leur utilisation pour la préparation de moyens diagnostiques
EP0157360B1 (fr)	1991-08-14	Esters chromogènes d'aminoacides et de peptides, procédés pour leur préparation, utilisation de ces agents dans des méthodes analytiques et agents pour l'identification d'enzymes estérolytiques et/ou protéolytiques
EP0157362A2 (fr)	1985-10-09	Esters chromogènes d'aminoacides et peptides, procédé pour leur préparation, utilisation de ces composés pour procédés analytiques ainsi comme agents pour marquer enzymes estérolytiques et/ou protéolytiques
DE19639169A1 (de)	1998-04-02	Redoxaktive Verbindungen und deren Anwendung
EP0158225B1 (fr)	1992-03-11	Méthode de dosage et agents pour détecter des enzymes estérolytiques et/ou protéolytiques
EP0008428B1 (fr)	1984-10-31	Réactif de diagnostic pour la détection des leucocytes dans les liquides corporels et colorants azoiques estérifiés leur servant d'agents chromogènes, procédé de préparation de ceux-ci et application à la préparation de produits de diagnostic pour la détection des leucocytes dans des liquides corporels
EP0423632A1 (fr)	1991-04-24	Substrats pour hydrolases
DE3644401A1 (de)	1988-07-07	Neue hydrolase-substrate
EP0034323B1 (fr)	1983-08-17	Esters d'aminoacides et de peptides de leuco-indoanilines, procédé pour leur préparation et agents contenant ces composés pour la détection d'enzymes protéolytiques
EP0433855B1 (fr)	2001-03-07	Ammophenols O- et N-substitués, intermédaires pour leur préparation, leur utilisation comme substrats pour hydrolases, procédé d'analyse correspondant et agents diagnostiques
EP0433853A1 (fr)	1991-06-26	Usage de 1-aryl semicarbazides pour la stabilisation de substrats d'enzymes, procédé correspondant et moyen diagnostique contenant ce stabilisateur
DE3534927A1 (de)	1987-04-02	Phosphate von resorufin-derivaten, verfahren zu deren herstellung sowie deren verwendung zur bestimmung der aktivitaet von phosphatasen
EP0210559B1 (fr)	1991-09-25	Dérivés de N-acyldéhydrorésorufine, procédé pour leur préparation ainsi que leur utilisation pour la détermination de peroxyde d'hydrogène, de composés à activité peroxydatiques ou de peroxydase
EP0158224B1 (fr)	1991-07-24	Méthode de dosage et agents pour détecter des enzymes estérolytiques et/ou protéolytiques
EP0157361B1 (fr)	1989-08-23	Méthode de dosage et agents pour détecter des enzymes estérolytiques et/ou protéolytiques
DE4015592A1 (de)	1991-11-21	Verfahren zur bestimmung eines ions mit erhoehter empfindlichkeit, verwendung hierfuer geeigneter substanzen und entsprechendes mittel
EP0457184B1 (fr)	1994-08-17	Dérivés naphtoliques, leur procédé de préparation et leur utilisation
SI8311124A8 (sl)	1995-12-31	Sredstvo in postopek za dokaz ekterolitskih in/ali proteolitskih encimov
DD236114A1 (de)	1986-05-28	Verfahren zur bestimmung von bakterieninfektion in liquores