JPH0253040B2 - - Google Patents

Info

Publication number: JPH0253040B2
Authority: JP; Japan
Prior art keywords: group; amino; carbon atoms; factor; methyl
Prior art date: 1980-02-12
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.): Expired - Lifetime

Application number

JP60299814A

Other languages

English (en)

Japanese (ja)

Other versions

JPS63300A (ja

Inventor

Rarusu Gundoro Suensen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

DSM Nutritional Products AG

Original Assignee

Pentapharm AG

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.)

1980-02-12

Filing date

1985-12-28

Publication date

1990-11-15

1985-12-28 Application filed by Pentapharm AG filed Critical Pentapharm AG

1988-01-05 Publication of JPS63300A publication Critical patent/JPS63300A/ja

1990-11-15 Publication of JPH0253040B2 publication Critical patent/JPH0253040B2/ja

Status Granted legal-status Critical Current

Links

-1 methoxy, methyl Chemical group 0.000 claims abstract description 63
125000000217 alkyl group Chemical group 0.000 claims abstract description 26
125000003277 amino group Chemical group 0.000 claims abstract description 13
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 13
239000000460 chlorine Chemical group 0.000 claims abstract description 10
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 6
229910052801 chlorine Chemical group 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 5
125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims abstract description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 5
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 5
125000001589 carboacyl group Chemical group 0.000 claims abstract 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 4
125000004432 carbon atom Chemical group C* 0.000 claims description 51
239000000243 solution Substances 0.000 claims description 38
230000015572 biosynthetic process Effects 0.000 claims description 25
229960002897 heparin Drugs 0.000 claims description 22
229920000669 heparin Polymers 0.000 claims description 22
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 21
238000004458 analytical method Methods 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 17
238000000034 method Methods 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 17
239000000047 product Substances 0.000 claims description 17
239000000872 buffer Substances 0.000 claims description 15
238000000354 decomposition reaction Methods 0.000 claims description 14
230000003287 optical effect Effects 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
238000012360 testing method Methods 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
238000005259 measurement Methods 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 6
239000007857 degradation product Substances 0.000 claims description 6
238000004445 quantitative analysis Methods 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
230000004913 activation Effects 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
230000008878 coupling Effects 0.000 claims description 5
238000010168 coupling process Methods 0.000 claims description 5
238000005859 coupling reaction Methods 0.000 claims description 5
150000008049 diazo compounds Chemical class 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
239000002821 viper venom Substances 0.000 claims description 5
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
125000006515 benzyloxy alkyl group Chemical group 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
238000007865 diluting Methods 0.000 claims description 3
PGOHTUIFYSHAQG-LJSDBVFPSA-N (2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoyl]amino]hexanoic acid Chemical compound CSCC[C@H](N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(O)=O PGOHTUIFYSHAQG-LJSDBVFPSA-N 0.000 claims description 2
108010000499 Thromboplastin Proteins 0.000 claims description 2
102000002262 Thromboplastin Human genes 0.000 claims description 2
239000007853 buffer solution Substances 0.000 claims 3
125000005843 halogen group Chemical group 0.000 claims 3
REAWNMHCBIUKLZ-ZYHUDNBSSA-N (3R,4R)-4-(hydroxymethyl)-3-(6-methylheptanoyl)oxolan-2-one Chemical compound CC(C)CCCCC(=O)[C@H]1[C@H](CO)COC1=O REAWNMHCBIUKLZ-ZYHUDNBSSA-N 0.000 claims 1
108010014173 Factor X Proteins 0.000 claims 1
241000282412 Homo Species 0.000 claims 1
241001465754 Metazoa Species 0.000 claims 1
230000003197 catalytic effect Effects 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
102000004190 Enzymes Human genes 0.000 abstract description 16
108090000790 Enzymes Proteins 0.000 abstract description 16
230000002255 enzymatic effect Effects 0.000 abstract description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 2
230000007071 enzymatic hydrolysis Effects 0.000 abstract description 2
238000006047 enzymatic hydrolysis reaction Methods 0.000 abstract description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 2
229910052736 halogen Chemical group 0.000 abstract description 2
150000002367 halogens Chemical group 0.000 abstract description 2
239000000463 material Substances 0.000 abstract description 2
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 abstract 1
108010074860 Factor Xa Proteins 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 abstract 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
150000002431 hydrogen Chemical group 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 abstract 1
239000007858 starting material Substances 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 106
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
238000004809 thin layer chromatography Methods 0.000 description 24
238000000921 elemental analysis Methods 0.000 description 23
239000000758 substrate Substances 0.000 description 23
239000003480 eluent Substances 0.000 description 22
108090000631 Trypsin Proteins 0.000 description 21
102000004142 Trypsin Human genes 0.000 description 21
239000012588 trypsin Substances 0.000 description 21
238000004364 calculation method Methods 0.000 description 18
229960000583 acetic acid Drugs 0.000 description 14
229920005654 Sephadex Polymers 0.000 description 13
229940088598 enzyme Drugs 0.000 description 13
239000012507 Sephadex™ Substances 0.000 description 12
235000001014 amino acid Nutrition 0.000 description 12
229940024606 amino acid Drugs 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000012043 crude product Substances 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
150000001413 amino acids Chemical class 0.000 description 11
239000012362 glacial acetic acid Substances 0.000 description 11
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 10
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 9
230000035945 sensitivity Effects 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
238000001035 drying Methods 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
239000004475 Arginine Substances 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 6
235000009697 arginine Nutrition 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
230000000694 effects Effects 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000010626 work up procedure Methods 0.000 description 5
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
108090000190 Thrombin Proteins 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
239000004019 antithrombin Substances 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
DEKPYXUDJRABNK-UHFFFAOYSA-N dimethyl 5-aminobenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(N)=CC(C(=O)OC)=C1 DEKPYXUDJRABNK-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000002523 gelfiltration Methods 0.000 description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical group C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 4
229960004072 thrombin Drugs 0.000 description 4
SFKZPTYRENGBTJ-UHFFFAOYSA-N 4-methoxynaphthalen-2-amine Chemical compound C1=CC=C2C(OC)=CC(N)=CC2=C1 SFKZPTYRENGBTJ-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
206010053567 Coagulopathies Diseases 0.000 description 3
150000008574 D-amino acids Chemical group 0.000 description 3
108010049003 Fibrinogen Proteins 0.000 description 3
102000008946 Fibrinogen Human genes 0.000 description 3
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
210000004899 c-terminal region Anatomy 0.000 description 3
230000035602 clotting Effects 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
229940012952 fibrinogen Drugs 0.000 description 3
238000011534 incubation Methods 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
108090000765 processed proteins & peptides Proteins 0.000 description 3
230000005588 protonation Effects 0.000 description 3
FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 2
PNHBRYIAJCYNDA-VQCQRNETSA-N (4r)-6-[2-[2-ethyl-4-(4-fluorophenyl)-6-phenylpyridin-3-yl]ethyl]-4-hydroxyoxan-2-one Chemical compound C([C@H](O)C1)C(=O)OC1CCC=1C(CC)=NC(C=2C=CC=CC=2)=CC=1C1=CC=C(F)C=C1 PNHBRYIAJCYNDA-VQCQRNETSA-N 0.000 description 2
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 2
PSWDQTMAUUQILQ-UHFFFAOYSA-N 2-[(6-methoxy-4-methylquinazolin-2-yl)amino]-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound N1=C(C)C2=CC(OC)=CC=C2N=C1NC1=NC(=O)C(C)=C(C)N1 PSWDQTMAUUQILQ-UHFFFAOYSA-N 0.000 description 2
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
OVDGUTHABMXVMI-UHFFFAOYSA-N 3-nitro-4-(propylamino)benzoic acid Chemical compound CCCNC1=CC=C(C(O)=O)C=C1[N+]([O-])=O OVDGUTHABMXVMI-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
AGPKZVBTJJNPAG-RFZPGFLSSA-N D-Isoleucine Chemical compound CC[C@@H](C)[C@@H](N)C(O)=O AGPKZVBTJJNPAG-RFZPGFLSSA-N 0.000 description 2
MTCFGRXMJLQNBG-UWTATZPHSA-N D-Serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 description 2
CKLJMWTZIZZHCS-UWTATZPHSA-N D-aspartic acid Chemical compound OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 2
HNDVDQJCIGZPNO-RXMQYKEDSA-N D-histidine Chemical compound OC(=O)[C@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-RXMQYKEDSA-N 0.000 description 2
AYFVYJQAPQTCCC-STHAYSLISA-N D-threonine Chemical compound C[C@H](O)[C@@H](N)C(O)=O AYFVYJQAPQTCCC-STHAYSLISA-N 0.000 description 2
OUYCCCASQSFEME-MRVPVSSYSA-N D-tyrosine Chemical compound OC(=O)[C@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-MRVPVSSYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
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OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
238000012800 visualization Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0819—Tripeptides with the first amino acid being acidic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/1008—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
- 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
- C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
- C12Q1/37—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase involving peptidase or proteinase
- 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
- C12Q1/56—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving blood clotting factors, e.g. involving thrombin, thromboplastin, fibrinogen
- 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
- C12Q2337/00—N-linked chromogens for determinations of peptidases and proteinases
- C12Q2337/10—Anilides
- C12Q2337/12—Para-Nitroanilides p-NA
- 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
- C12Q2337/00—N-linked chromogens for determinations of peptidases and proteinases
- C12Q2337/20—Coumarin derivatives
- C12Q2337/22—7-Amino-4-methylcoumarin, i.e. AMC, MCA
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/90—Enzymes; Proenzymes
- G01N2333/914—Hydrolases (3)
- G01N2333/948—Hydrolases (3) acting on peptide bonds (3.4)
- G01N2333/95—Proteinases, i.e. endopeptidases (3.4.21-3.4.99)
- G01N2333/964—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue
- G01N2333/96425—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue from mammals
- G01N2333/96427—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue from mammals in general
- G01N2333/9643—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue from mammals in general with EC number
- G01N2333/96433—Serine endopeptidases (3.4.21)
- G01N2333/96441—Serine endopeptidases (3.4.21) with definite EC number
- G01N2333/96444—Factor X (3.4.21.6)
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/81—Packaged device or kit
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/802—Chromogenic or luminescent peptides
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/28—Bound to a nonpeptide drug, nonpeptide label, nonpeptide carrier, or a nonpeptide resin
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/10—Composition for standardization, calibration, simulation, stabilization, preparation or preservation; processes of use in preparation for chemical testing
- Y10T436/106664—Blood serum or blood plasma standard or control
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/10—Composition for standardization, calibration, simulation, stabilization, preparation or preservation; processes of use in preparation for chemical testing
- Y10T436/108331—Preservative, buffer, anticoagulant or diluent
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/10—Composition for standardization, calibration, simulation, stabilization, preparation or preservation; processes of use in preparation for chemical testing
- Y10T436/109163—Inorganic standards or controls

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
General Health & Medical Sciences (AREA)
Biophysics (AREA)
Medicinal Chemistry (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
Engineering & Computer Science (AREA)
Analytical Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Biotechnology (AREA)
Immunology (AREA)
Microbiology (AREA)
General Engineering & Computer Science (AREA)
Physics & Mathematics (AREA)
Hematology (AREA)
Neurosurgery (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Peptides Or Proteins (AREA)
Investigating Or Analysing Biological Materials (AREA)
Enzymes And Modification Thereof (AREA)
Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
Meat, Egg Or Seafood Products (AREA)
Saccharide Compounds (AREA)

JP60299814A 1980-02-12 1985-12-28 媒体中の第Ｘａ−因子、ヘパリン又は第Ｘａ−抗因子を定量分析する方法 Granted JPS63300A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1130/80-1		1980-02-12
CH113080		1980-02-12

Publications (2)

Publication Number	Publication Date
JPS63300A JPS63300A (ja)	1988-01-05
JPH0253040B2 true JPH0253040B2 (2)	1990-11-15

Family

ID=4203192

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP56500604A Expired - Lifetime JPH032879B2 (2)	1980-02-12	1981-02-06
JP60299814A Granted JPS63300A (ja)	1980-02-12	1985-12-28	媒体中の第Ｘａ−因子、ヘパリン又は第Ｘａ−抗因子を定量分析する方法

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
JP56500604A Expired - Lifetime JPH032879B2 (2)	1980-02-12	1981-02-06

Country Status (13)

Country	Link
US (2)	US4440678A (2)
EP (1)	EP0034122B1 (2)
JP (2)	JPH032879B2 (2)
AT (1)	ATE4702T1 (2)
AU (1)	AU581050B2 (2)
CA (1)	CA1161432A (2)
DE (1)	DE3160903D1 (2)
DK (1)	DK154221C (2)
ES (1)	ES8302780A1 (2)
IL (1)	IL62096A (2)
NO (1)	NO151787C (2)
WO (1)	WO1981002294A1 (2)
ZA (1)	ZA81789B (2)

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US8941631B2 (en)	2007-11-16	2015-01-27	Qualcomm Mems Technologies, Inc.	Simultaneous light collection and illumination on an active display

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DE3244030A1 (de) *	1982-11-27	1984-05-30	Behringwerke Ag, 3550 Marburg	Chromogene verbindungen, verfahren zu ihrer herstellung und ihre verwendung
JPS59112952A (ja) *	1982-12-21	1984-06-29	Taisho Pharmaceut Co Ltd	ペプチド誘導体
DE3311287A1 (de) *	1983-03-28	1984-10-04	Behringwerke Ag, 3550 Marburg	Verfahren zur fotometrischen bestimmung der aktivierten partiellen thromboplastinzeit und reagenz dazu
EP0128118B1 (de) *	1983-06-03	1991-08-14	Pentapharm A.G.	Peptidderivate und deren Verwendung als Substrate zur quantitativen Bestimmung von Enzymen
JPS60241900A (ja) *	1984-05-16	1985-11-30	Nitto Boseki Co Ltd	新規な第Ｘａ因子活性測定用基質
DE3504405A1 (de) *	1985-02-08	1986-08-14	Boehringer Mannheim Gmbh, 6800 Mannheim	Bestimmung von prokallikrein
GB8504522D0 (en) *	1985-02-21	1985-03-27	Genetics Int Inc	Electrochemistry of mediators
FI860043A7 (fi) *	1986-01-06	1987-07-07	Orion Yhtymae Oy	Peptidisubstraatit sekä menetelmä endotoksiinin kvantitatiiviseksi määrittämiseksi.
SE461494B (sv) *	1986-03-21	1990-02-19	Thorsman & Co Ab	Faestanordning foer en elektrisk kopplingsdosa
SE8601327D0 (sv) *	1986-03-21	1986-03-21	Kabivitrum Ab	Nya peptidderivat
DE3783966T2 (de) *	1986-07-29	1993-05-27	Sunstar Inc	Reagens zur pruefung von periodentalen erkrankungen.
DE3629175A1 (de) *	1986-08-28	1988-03-17	Behringwerke Ag	Chromogene verbindungen, verfahren zu deren herstellung und ihre verwendung
US5110727A (en) *	1987-04-03	1992-05-05	Cardiovascular Diagnostics, Inc.	Method for performing coagulation assays accurately, rapidly and simply, using dry chemical reagents and paramagnetic particles
US5115099A (en) *	1988-06-14	1992-05-19	Nitto Boseki Co., Ltd.	Substrates for determination of enzyme activity and intermediates for synthesis of the substrates as well as process for producing the intermediates
JPH06104079B2 (ja) *	1988-07-14	1994-12-21	日東紡績株式会社	新規な酵素活性測定用基質
WO1990003577A1 (en)	1988-09-30	1990-04-05	The University Of Vermont And State Agricultural College	Immunoassays for catalytically-active, serine proteases
US5320945A (en) *	1989-07-14	1994-06-14	Boehringer Mannheim Gmbh	Method and reagent for the determination of antithrombin III
ES2078978T3 (es)	1989-08-17	1996-01-01	Baxter Diagnostics Inc	Procedimiento de determinacion cromogenica de niveles de factores de coagulacion sanguinea en plasma y otros fluidos.
FR2658519B1 (fr) *	1990-02-19	1995-07-07	Serbio	Substrats peptidiques pour identification du facteur xa.
US6348570B1 (en) *	1991-08-16	2002-02-19	Merck & Co., Inc.	Chromophore containing compounds and their use in determining interleukin-1β convertase activity
US5308756A (en) *	1991-11-20	1994-05-03	Baxter Diagnostics Inc.	Protein S chromogenic assay
PT937158E (pt) *	1996-10-31	2001-06-29	Roche Diagnostics Gmbh	Processo para a determinacao da actividade catalitica de factor ixa
US6297024B1 (en)	1998-10-15	2001-10-02	Cell Activation, Inc.	Methods for assessing complement activation
US6235494B1 (en)	1999-02-08	2001-05-22	The Scripps Research Institute	Substrates for assessing mannan-binding protein-associated serine protease activity and methods using the substrates
CA2363827A1 (en) *	1999-02-23	2000-08-31	Pentapharm Ag	Oligopeptide derivatives for the electrochemical measurement of protease activity
WO2003022873A1 (de) *	2001-09-10	2003-03-20	Novel Science International Gmbh	Organische verbindungen mit biologischer wirkung als thrombinhemmer und ihre verwendung
DE102005003145B4 (de) *	2005-01-21	2006-10-19	Dade Behring Marburg Gmbh	Stablies, chromogenes Flüssigreagenz und dessen Verwendung in gerinnungsdiagnostischen Tests
EP2333555A1 (de)	2009-12-09	2011-06-15	Siemens Healthcare Diagnostics Products GmbH	Heterogener Gerinnungstest
EP2465941A1 (de)	2010-12-20	2012-06-20	Siemens Healthcare Diagnostics Products GmbH	Verfahren zur simultanen Bestimmung mehrerer Gerinnungsproteasen
EP2484775A1 (de)	2011-02-07	2012-08-08	Siemens Healthcare Diagnostics Products GmbH	Heparin-insensitives Verfahren zur Bestimmung von direkten Gerinnungsfaktorinhibitoren
EP2843416A1 (de)	2013-09-02	2015-03-04	Siemens Healthcare Diagnostics Products GmbH	Kontroll- und Kalibratormaterial für die Bestimmung von direkten Antikoagulanzien
EP3348649A1 (de)	2017-01-16	2018-07-18	Siemens Healthcare Diagnostics Products GmbH	Universales kontrollmaterial für gerinnungsfaktorinhibitor-teste

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IL42124A (en) *	1972-05-02	1977-02-28	Kabi Ab	Substrate for the determination of proteolytic enzymes
US4162941A (en) *	1974-12-05	1979-07-31	Ab Kabi	Method for determining a proteolytic enzyme
SE407058B (sv) *	1974-12-05	1979-03-12	Kabi Ab	Nya kromogena enzymsubstrat for serinproteaser
CH622286A5 (2) *	1975-06-23	1981-03-31	Pentapharm Ag
SE407571B (sv) *	1975-07-11	1979-04-02	Kabi Ab	Nya kromogena enzymsubstrat for serinproteaser
US4137225A (en) *	1975-07-11	1979-01-30	Ab Kabi	Novel chromogenic enzyme substrates
US4061625A (en) *	1975-07-11	1977-12-06	Ab Kabi	Novel chromogenic thrombin substrates
SE419871B (sv) *	1975-12-01	1981-08-31	Pharmacia Ab	Sett att bestemma aktiviteten hos faktor xa-inhibitor i blod
CH634662A5 (de) *	1976-05-28	1983-02-15	Pentapharm Ag	Verwendung von tripeptidderivaten zur quantitativen bestimmung von plasminogen-aktivatoren.
SE437153B (sv) *	1976-12-01	1985-02-11	Kabi Ab	Specifika kromogena enzymsubstrat for serinproteaser
SE7801373L (sv) *	1978-02-07	1979-08-08	Kabi Ab	Lett spjelkbara substrat for kvantifiering av proteaser
US4275153A (en) *	1978-08-03	1981-06-23	American Hospital Supply Corporation	Analytical fluorogenic substrates for proteolytic enzymes
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1981
- 1981-02-05 CA CA000370232A patent/CA1161432A/en not_active Expired
- 1981-02-06 JP JP56500604A patent/JPH032879B2/ja not_active Expired - Lifetime
- 1981-02-06 WO PCT/CH1981/000014 patent/WO1981002294A1/de not_active Ceased
- 1981-02-06 AT AT81810036T patent/ATE4702T1/de not_active IP Right Cessation
- 1981-02-06 ZA ZA00810789A patent/ZA81789B/xx unknown
- 1981-02-06 US US06/302,420 patent/US4440678A/en not_active Expired - Lifetime
- 1981-02-06 DE DE8181810036T patent/DE3160903D1/de not_active Expired
- 1981-02-06 EP EP81810036A patent/EP0034122B1/de not_active Expired
- 1981-02-09 IL IL62096A patent/IL62096A/xx not_active IP Right Cessation
- 1981-02-11 ES ES499343A patent/ES8302780A1/es not_active Expired
- 1981-10-09 NO NO813418A patent/NO151787C/no unknown
- 1981-10-12 DK DK451981A patent/DK154221C/da not_active IP Right Cessation
1982
- 1982-09-15 US US06/418,257 patent/US4480030A/en not_active Expired - Lifetime
1985
- 1985-12-28 JP JP60299814A patent/JPS63300A/ja active Granted
1986
- 1986-01-13 AU AU52204/86A patent/AU581050B2/en not_active Ceased

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8941631B2 (en)	2007-11-16	2015-01-27	Qualcomm Mems Technologies, Inc.	Simultaneous light collection and illumination on an active display

Also Published As

Publication number	Publication date
AU581050B2 (en)	1989-02-09
NO813418L (no)	1981-10-09
US4480030A (en)	1984-10-30
NO151787B (no)	1985-02-25
DK451981A (da)	1981-10-12
JPH032879B2 (2)	1991-01-17
JPS56501849A (2)	1981-12-17
ES499343A0 (es)	1983-01-16
DK154221C (da)	1989-05-22
EP0034122B1 (de)	1983-09-21
NO151787C (no)	1985-06-05
US4440678A (en)	1984-04-03
IL62096A0 (en)	1981-03-31
IL62096A (en)	1986-09-30
JPS63300A (ja)	1988-01-05
DE3160903D1 (en)	1983-10-27
AU5220486A (en)	1986-05-15
ATE4702T1 (de)	1983-10-15
ZA81789B (en)	1982-03-31
WO1981002294A1 (fr)	1981-08-20
DK154221B (da)	1988-10-24
CA1161432A (en)	1984-01-31
ES8302780A1 (es)	1983-01-16
EP0034122A1 (de)	1981-08-19

Publication	Publication Date	Title
US4440678A (en)	1984-04-03	Tripeptide derivatives and their application in assaying enzymes
US4028318A (en)	1977-06-07	Chromogenic enzyme substrates
SU1277904A3 (ru)	1986-12-15	Способ получени трипептидов
EP0046742B1 (en)	1984-06-27	Peptide substrates for determination of protease activity
US4016042A (en)	1977-04-05	Substrate for the quantitative determination of enzymes
DK149333B (da)	1986-05-05	Tripeptidderivater samt salte deraf med mineralsyrer eller organiske syrer til anvendelse som substrater til kvantitativ bestemmelse af thrombin og thrombinlignende enzymer, ecarinthrombin, plasmin og plasminlignende enzymer samt proenzymer, proenzymaktivatorer og enzyminhibitorer herfor i legemsvaeskerfra mennesker og pattedyr samt i dyriske celleekstrakter
JPH0616719B2 (ja)	1994-03-09	酵素の検出および測定用色原体基質
US4190574A (en)	1980-02-26	Substrate for the quantitative determination of plasminogen activators
US4563305A (en)	1986-01-07	Radiolabelled substrates for assaying mammalian enzymes
US4428874A (en)	1984-01-31	Tripeptide derivatives
US4510241A (en)	1985-04-09	Peptide-type substrates useful in the quantitative determination of endotoxin
US4448715A (en)	1984-05-15	Tagged pyroglu-L-Phe-L-Arg derivatives, substrates and assays for kallikrein
US4406832A (en)	1983-09-27	Peptide-type substrates useful in the quantitative determination of endotoxin
US4568636A (en)	1986-02-04	Tripeptide derivatives
US4216142A (en)	1980-08-05	Chromogenic substrates for the proteolytic enzymes
GB2126720A (en)	1984-03-28	A method for determination of enzyme activity
US4169015A (en)	1979-09-25	Novel chromogenic thrombin substrates
US4162941A (en)	1979-07-31	Method for determining a proteolytic enzyme
Rush et al.	1984	Fluorogenic substrates for the enkephalin-degrading neutral endopeptidase (Enkephalinase)
DK168574B1 (da)	1994-04-25	Peptidderivater og salte deraf med mineralsyrer eller organiske syrer samt anvendelsen heraf som substrat til kvantitativ bestemmelse af C1-esterase
JP2560058B2 (ja)	1996-12-04	新規なペプチド誘導体
JPH0244840B2 (2)	1990-10-05
JPH0776232B2 (ja)	1995-08-16	ペプチド誘導体及びその使用方法

JPH0253040B2 - - Google Patents

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