JPS6257197B2 - - Google Patents
Info
- Publication number
- JPS6257197B2 JPS6257197B2 JP56064315A JP6431581A JPS6257197B2 JP S6257197 B2 JPS6257197 B2 JP S6257197B2 JP 56064315 A JP56064315 A JP 56064315A JP 6431581 A JP6431581 A JP 6431581A JP S6257197 B2 JPS6257197 B2 JP S6257197B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- group
- arg
- solution
- mmol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 139
- -1 cyclohexylalanyl group Chemical group 0.000 claims description 24
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 235000011054 acetic acid Nutrition 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 2
- 159000000032 aromatic acids Chemical group 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 229960002449 glycine Drugs 0.000 claims description 2
- 235000013905 glycine and its sodium salt Nutrition 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 2
- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 claims description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 claims 1
- 150000001243 acetic acids Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 129
- 239000000243 solution Substances 0.000 description 62
- 239000000758 substrate Substances 0.000 description 45
- 108090000631 Trypsin Proteins 0.000 description 34
- 102000004142 Trypsin Human genes 0.000 description 34
- 239000012588 trypsin Substances 0.000 description 34
- 238000004809 thin layer chromatography Methods 0.000 description 30
- 238000004364 calculation method Methods 0.000 description 28
- 108090000790 Enzymes Proteins 0.000 description 27
- 102000004190 Enzymes Human genes 0.000 description 27
- 238000000921 elemental analysis Methods 0.000 description 27
- 229940088598 enzyme Drugs 0.000 description 27
- 108010088842 Fibrinolysin Proteins 0.000 description 24
- 102000001399 Kallikrein Human genes 0.000 description 24
- 108060005987 Kallikrein Proteins 0.000 description 24
- 102000057032 Tissue Kallikreins Human genes 0.000 description 24
- 229940012957 plasmin Drugs 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 229920005654 Sephadex Polymers 0.000 description 21
- 229960000583 acetic acid Drugs 0.000 description 21
- 239000012507 Sephadex™ Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 20
- 210000000056 organ Anatomy 0.000 description 19
- 239000012043 crude product Substances 0.000 description 17
- 239000012362 glacial acetic acid Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 101710103262 Glandular kallikrein Proteins 0.000 description 14
- 229940024606 amino acid Drugs 0.000 description 14
- 235000001014 amino acid Nutrition 0.000 description 14
- 150000001413 amino acids Chemical class 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 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 12
- 210000002700 urine Anatomy 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 108091005804 Peptidases Proteins 0.000 description 10
- 102000035195 Peptidases Human genes 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 108700022175 Tissue Kallikreins Proteins 0.000 description 9
- 239000004475 Arginine Substances 0.000 description 8
- 108090000113 Plasma Kallikrein Proteins 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 8
- 238000010626 work up procedure Methods 0.000 description 8
- SFKZPTYRENGBTJ-UHFFFAOYSA-N 4-methoxynaphthalen-2-amine Chemical compound C1=CC=C2C(OC)=CC(N)=CC2=C1 SFKZPTYRENGBTJ-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 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 7
- 238000001035 drying Methods 0.000 description 7
- 238000002523 gelfiltration Methods 0.000 description 7
- 108090000765 processed proteins & peptides Proteins 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 206010036790 Productive cough Diseases 0.000 description 6
- 108090000190 Thrombin Proteins 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 6
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 6
- 239000007857 degradation product Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000004445 quantitative analysis Methods 0.000 description 6
- 230000028327 secretion Effects 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 238000002798 spectrophotometry method Methods 0.000 description 6
- 210000003802 sputum Anatomy 0.000 description 6
- 208000024794 sputum Diseases 0.000 description 6
- 229960004072 thrombin Drugs 0.000 description 6
- 229960005356 urokinase Drugs 0.000 description 6
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000004472 Lysine Substances 0.000 description 4
- 102000003827 Plasma Kallikrein Human genes 0.000 description 4
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000008033 biological extinction Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- GLNDAGDHSLMOKX-UHFFFAOYSA-N coumarin 120 Chemical compound C1=C(N)C=CC2=C1OC(=O)C=C2C GLNDAGDHSLMOKX-UHFFFAOYSA-N 0.000 description 4
- 230000000762 glandular Effects 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
- 239000002244 precipitate Substances 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 229910052722 tritium Inorganic materials 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940122618 Trypsin inhibitor Drugs 0.000 description 3
- 101710162629 Trypsin inhibitor Proteins 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 210000004899 c-terminal region Anatomy 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 description 3
- QAPTWHXHEYAIKG-RCOXNQKVSA-N n-[(1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 QAPTWHXHEYAIKG-RCOXNQKVSA-N 0.000 description 3
- 239000012264 purified product Substances 0.000 description 3
- 239000002753 trypsin inhibitor Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 2
- 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
- QBXVXKRWOVBUDB-GRKNLSHJSA-N ClC=1C(=CC(=C(CN2[C@H](C[C@H](C2)O)C(=O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound ClC=1C(=CC(=C(CN2[C@H](C[C@H](C2)O)C(=O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C QBXVXKRWOVBUDB-GRKNLSHJSA-N 0.000 description 2
- 108010016626 Dipeptides Proteins 0.000 description 2
- 108010062466 Enzyme Precursors Proteins 0.000 description 2
- 102000010911 Enzyme Precursors Human genes 0.000 description 2
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229940125907 SJ995973 Drugs 0.000 description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical compound CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000001980 alanyl group Chemical group 0.000 description 2
- 150000003862 amino acid derivatives Chemical class 0.000 description 2
- 125000000637 arginyl group Chemical class N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 239000012496 blank sample Substances 0.000 description 2
- 210000001124 body fluid Anatomy 0.000 description 2
- 239000010839 body fluid Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229940125872 compound 4d Drugs 0.000 description 2
- 238000007257 deesterification reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000002848 electrochemical method Methods 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 210000004907 gland Anatomy 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- TWYRZWVFWYSNBU-JTQLQIEISA-N l-arg p-nitroanilide Chemical compound NC(N)=NCCC[C@H](N)C(=O)NC1=CC=C([N+]([O-])=O)C=C1 TWYRZWVFWYSNBU-JTQLQIEISA-N 0.000 description 2
- 125000001998 leucyl group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- XZMHJYWMCRQSSI-UHFFFAOYSA-N n-[5-[2-(3-acetylanilino)-1,3-thiazol-4-yl]-4-methyl-1,3-thiazol-2-yl]benzamide Chemical compound CC(=O)C1=CC=CC(NC=2SC=C(N=2)C2=C(N=C(NC(=O)C=3C=CC=CC=3)S2)C)=C1 XZMHJYWMCRQSSI-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 210000001819 pancreatic juice Anatomy 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000005375 photometry Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
- 125000002114 valyl group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PHDIJLFSKNMCMI-ITGJKDDRSA-N (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol Chemical compound OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OCCCCCCCCOC=1C=C2C=CC=NC2=CC=1)O PHDIJLFSKNMCMI-ITGJKDDRSA-N 0.000 description 1
- MNIPVWXWSPXERA-IDNZQHFXSA-N (6r,7r)-1-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-4,7-dihydroxy-6-(11-phenoxyundecanoyloxy)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CCC12[C@@H]([C@@H](OC(=O)CCCCCCCCCCOC=3C=CC=CC=3)C(O1)(C(O)=O)C(O)(C(O2)C(O)=O)C(O)=O)O)C1=CC=CC=C1 MNIPVWXWSPXERA-IDNZQHFXSA-N 0.000 description 1
- QRDAPCMJAOQZSU-KQQUZDAGSA-N (e)-3-[4-[(e)-3-(3-fluorophenyl)-3-oxoprop-1-enyl]-1-methylpyrrol-2-yl]-n-hydroxyprop-2-enamide Chemical compound C1=C(\C=C\C(=O)NO)N(C)C=C1\C=C\C(=O)C1=CC=CC(F)=C1 QRDAPCMJAOQZSU-KQQUZDAGSA-N 0.000 description 1
- JNPGUXGVLNJQSQ-BGGMYYEUSA-M (e,3r,5s)-7-[4-(4-fluorophenyl)-1,2-di(propan-2-yl)pyrrol-3-yl]-3,5-dihydroxyhept-6-enoate Chemical compound CC(C)N1C(C(C)C)=C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)C(C=2C=CC(F)=CC=2)=C1 JNPGUXGVLNJQSQ-BGGMYYEUSA-M 0.000 description 1
- VAVHMEQFYYBAPR-ITWZMISCSA-N (e,3r,5s)-7-[4-(4-fluorophenyl)-1-phenyl-2-propan-2-ylpyrrol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound CC(C)C1=C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)C(C=2C=CC(F)=CC=2)=CN1C1=CC=CC=C1 VAVHMEQFYYBAPR-ITWZMISCSA-N 0.000 description 1
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Landscapes
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH351580 | 1980-05-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS572253A JPS572253A (en) | 1982-01-07 |
| JPS6257197B2 true JPS6257197B2 (fr) | 1987-11-30 |
Family
ID=4257649
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6431581A Granted JPS572253A (en) | 1980-05-06 | 1981-04-30 | Tripeptide derivative and quantitative analysis of proteinase |
| JP5224287A Expired - Lifetime JPH0244518B2 (ja) | 1980-05-06 | 1987-03-09 | Tanpakubunkaikosooteiryobunsekisuruhoho |
| JP5224187A Granted JPS62294696A (ja) | 1980-05-06 | 1987-03-09 | トリペプチド誘導体 |
| JP5224087A Granted JPS62294695A (ja) | 1980-05-06 | 1987-03-09 | トリペプチド誘導体 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5224287A Expired - Lifetime JPH0244518B2 (ja) | 1980-05-06 | 1987-03-09 | Tanpakubunkaikosooteiryobunsekisuruhoho |
| JP5224187A Granted JPS62294696A (ja) | 1980-05-06 | 1987-03-09 | トリペプチド誘導体 |
| JP5224087A Granted JPS62294695A (ja) | 1980-05-06 | 1987-03-09 | トリペプチド誘導体 |
Country Status (3)
| Country | Link |
|---|---|
| JP (4) | JPS572253A (fr) |
| DK (2) | DK155051C (fr) |
| NO (1) | NO155540C (fr) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1179200B (de) * | 1960-01-26 | 1964-10-08 | Hoechst Ag | Verfahren zur Herstellung von N-Benzolsulfonyl-N'-methyl-cyclohexylharnstoffen |
| SE380257B (sv) * | 1972-05-02 | 1975-11-03 | Bofors Ab | Nya diagnostiskt verksamma substrat med hog specificitet till trombin och andra proteolytiska enzymer av typen peptidyl-peptid-hydrolaser |
| JPS4942396A (fr) * | 1973-05-01 | 1974-04-20 | ||
| SE407405B (sv) * | 1975-07-11 | 1979-03-26 | Kabi Ab | Nya kromogena trombinsubstrat |
| SE407571B (sv) * | 1975-07-11 | 1979-04-02 | Kabi Ab | Nya kromogena enzymsubstrat for serinproteaser |
| CH634662A5 (de) * | 1976-05-28 | 1983-02-15 | Pentapharm Ag | Verwendung von tripeptidderivaten zur quantitativen bestimmung von plasminogen-aktivatoren. |
| CA1161431A (fr) * | 1979-05-11 | 1984-01-31 | Lars G. Svendsen | Derives de tripeptide |
-
1981
- 1981-04-06 DK DK155781A patent/DK155051C/da not_active IP Right Cessation
- 1981-04-30 JP JP6431581A patent/JPS572253A/ja active Granted
- 1981-05-05 NO NO811510A patent/NO155540C/no not_active IP Right Cessation
-
1987
- 1987-03-09 JP JP5224287A patent/JPH0244518B2/ja not_active Expired - Lifetime
- 1987-03-09 JP JP5224187A patent/JPS62294696A/ja active Granted
- 1987-03-09 JP JP5224087A patent/JPS62294695A/ja active Granted
-
1988
- 1988-09-13 DK DK509788A patent/DK159458C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK509788A (da) | 1988-09-13 |
| JPH0244518B2 (ja) | 1990-10-04 |
| JPS572253A (en) | 1982-01-07 |
| DK159458C (da) | 1991-03-04 |
| DK155781A (da) | 1981-11-07 |
| DK509788D0 (da) | 1988-09-13 |
| DK155051B (da) | 1989-01-30 |
| JPH0244840B2 (fr) | 1990-10-05 |
| JPS62296899A (ja) | 1987-12-24 |
| JPS62294696A (ja) | 1987-12-22 |
| NO155540B (no) | 1987-01-05 |
| DK159458B (da) | 1990-10-15 |
| DK155051C (da) | 1989-07-03 |
| NO811510L (no) | 1981-11-09 |
| JPS62294695A (ja) | 1987-12-22 |
| JPH0244839B2 (fr) | 1990-10-05 |
| NO155540C (no) | 1987-04-15 |
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