TWI240723B - Substituted naphthyl benzofuran derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1) - Google Patents
Substituted naphthyl benzofuran derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1) Download PDFInfo
- Publication number
- TWI240723B TWI240723B TW091112529A TW91112529A TWI240723B TW I240723 B TWI240723 B TW I240723B TW 091112529 A TW091112529 A TW 091112529A TW 91112529 A TW91112529 A TW 91112529A TW I240723 B TWI240723 B TW I240723B
- Authority
- TW
- Taiwan
- Prior art keywords
- benzofuran
- naphthyl
- scope
- patent application
- pharmaceutically acceptable
- Prior art date
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- -1 naphthyl benzofuran derivatives Chemical class 0.000 title claims abstract description 168
- 108010022233 Plasminogen Activator Inhibitor 1 Proteins 0.000 title claims abstract description 31
- 102000012335 Plasminogen Activator Inhibitor 1 Human genes 0.000 title claims abstract description 30
- 239000003112 inhibitor Substances 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 192
- 150000003839 salts Chemical class 0.000 claims abstract description 53
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 35
- 125000003118 aryl group Chemical group 0.000 claims abstract description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 15
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 208000005069 pulmonary fibrosis Diseases 0.000 claims abstract description 6
- 125000005024 alkenyl aryl group Chemical group 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 4
- 239000003527 fibrinolytic agent Substances 0.000 claims abstract description 4
- 230000003480 fibrinolytic effect Effects 0.000 claims abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 108
- 150000002148 esters Chemical group 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 47
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 12
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 208000005189 Embolism Diseases 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 230000015271 coagulation Effects 0.000 claims description 6
- 238000005345 coagulation Methods 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 210000003462 vein Anatomy 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 230000015556 catabolic process Effects 0.000 claims description 4
- 230000002107 myocardial effect Effects 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 102000009123 Fibrin Human genes 0.000 claims description 3
- 108010073385 Fibrin Proteins 0.000 claims description 3
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 claims description 3
- 230000003143 atherosclerotic effect Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229950003499 fibrin Drugs 0.000 claims description 3
- 230000002093 peripheral effect Effects 0.000 claims description 3
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims description 2
- RCLVYHIXCSLQDS-UHFFFAOYSA-N 2-[6-(3-pentyl-1-benzofuran-2-yl)naphthalen-2-yl]oxyacetic acid Chemical compound C1=C(OCC(O)=O)C=CC2=CC(C3=C(C4=CC=CC=C4O3)CCCCC)=CC=C21 RCLVYHIXCSLQDS-UHFFFAOYSA-N 0.000 claims description 2
- 208000031104 Arterial Occlusive disease Diseases 0.000 claims description 2
- 206010008088 Cerebral artery embolism Diseases 0.000 claims description 2
- 102000001938 Plasminogen Activators Human genes 0.000 claims description 2
- 108010001014 Plasminogen Activators Proteins 0.000 claims description 2
- 208000007502 anemia Diseases 0.000 claims description 2
- 208000021328 arterial occlusion Diseases 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 201000010849 intracranial embolism Diseases 0.000 claims description 2
- 230000003902 lesion Effects 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229940127126 plasminogen activator Drugs 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 208000003663 ventricular fibrillation Diseases 0.000 claims description 2
- QAJLAJGOUHWOEW-UHFFFAOYSA-N 5-[[6-(3-pentyl-1-benzofuran-2-yl)naphthalen-2-yl]oxymethyl]-2h-tetrazole Chemical compound O1C2=CC=CC=C2C(CCCCC)=C1C(C=C1C=C2)=CC=C1C=C2OCC1=NN=NN1 QAJLAJGOUHWOEW-UHFFFAOYSA-N 0.000 claims 2
- GAYZBHFSLMXJGY-UHFFFAOYSA-N 1-[2-[5-bromo-6-(2h-tetrazol-5-ylmethoxy)naphthalen-2-yl]-5-chloro-1-benzofuran-3-yl]pentan-1-one Chemical compound O1C2=CC=C(Cl)C=C2C(C(=O)CCCC)=C1C(C=C1C=C2)=CC=C1C(Br)=C2OCC1=NN=NN1 GAYZBHFSLMXJGY-UHFFFAOYSA-N 0.000 claims 1
- 206010053567 Coagulopathies Diseases 0.000 claims 1
- 208000015294 blood coagulation disease Diseases 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 claims 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 239000000052 vinegar Chemical group 0.000 claims 1
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- 238000000034 method Methods 0.000 abstract description 131
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- 206010047249 Venous thrombosis Diseases 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 230000003278 mimic effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 250
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 206
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 128
- 239000007787 solid Substances 0.000 description 107
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- 229910001868 water Inorganic materials 0.000 description 97
- 235000019439 ethyl acetate Nutrition 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 76
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 75
- 238000001819 mass spectrum Methods 0.000 description 65
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 64
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 61
- 238000000921 elemental analysis Methods 0.000 description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
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- 230000008569 process Effects 0.000 description 45
- 238000003818 flash chromatography Methods 0.000 description 43
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- 229960000583 acetic acid Drugs 0.000 description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- 239000003480 eluent Substances 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 31
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
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- 239000012267 brine Substances 0.000 description 20
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
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- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 18
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 17
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 15
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- 238000006243 chemical reaction Methods 0.000 description 12
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
- 208000024891 symptom Diseases 0.000 description 11
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- 238000010168 coupling process Methods 0.000 description 10
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 9
- 229910052778 Plutonium Inorganic materials 0.000 description 9
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 9
- 108090000373 Tissue Plasminogen Activator Proteins 0.000 description 9
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- 238000004364 calculation method Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 9
- OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 description 9
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 9
- 229960000187 tissue plasminogen activator Drugs 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
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- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 8
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- 238000002360 preparation method Methods 0.000 description 8
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- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- HECLRDQVFMWTQS-HORUIINNSA-N bis[cyclopentadiene] Chemical compound C1C2[C@H]3CC=C[C@H]3C1C=C2 HECLRDQVFMWTQS-HORUIINNSA-N 0.000 description 7
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 7
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- PHFJAODRBDSBPX-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)-1-benzofuran Chemical compound C1=CC=C2OC(C3=CC4=CC=C(C=C4C=C3)OC)=CC2=C1 PHFJAODRBDSBPX-UHFFFAOYSA-N 0.000 description 6
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- 239000000284 extract Substances 0.000 description 4
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Classifications
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Landscapes
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Applications Claiming Priority (1)
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| US29970201P | 2001-06-20 | 2001-06-20 |
Publications (1)
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| US7374886B2 (en) | 1999-04-09 | 2008-05-20 | Rigshospitalet | Tissue inhibitor of matrix metalloproteinases type-1 (TIMP-1) as a cancer marker and postoperative marker for minimal residual disease or recurrent disease in patients with a prior history of cancer |
| TWI224101B (en) * | 2001-06-20 | 2004-11-21 | Wyeth Corp | Substituted naphthyl indole derivatives as inhibitors of plasminogen activator inhibitor type-1 (PAI-1) |
| ATE367812T1 (de) * | 2001-06-20 | 2007-08-15 | Wyeth Corp | Substituierte indolsäurederivate als inhibitoren von plasminogen-aktivator-inhibitor-1 (pai-1) |
| US7291639B2 (en) * | 2001-06-20 | 2007-11-06 | Wyeth | Aryloxy-acetic acid compounds useful as inhibitors of plasminogen activator inhibitor-1 (PAI-1) |
| AU2003296324A1 (en) * | 2002-12-10 | 2004-06-30 | Wyeth | Aryl, aryloxy, and alkyloxy substituted 1h-indol-3-yl glyoxylic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
| DE60306548T2 (de) * | 2002-12-10 | 2007-06-21 | Wyeth | Substituierte 3-carbonyl-1-yl-essigsäure-derivate als plasminogen aktivator inhibitor(pai-1) inhibitoren |
| UA80453C2 (en) * | 2002-12-10 | 2007-09-25 | Derivatives of substituted dyhydropyranoindol-3,4-dion as inhibitors of plasminogen activator inhibitor-1 (pai-1) | |
| CA2509170A1 (en) * | 2002-12-10 | 2004-06-24 | Wyeth | Substituted 3-alkyl and 3-arylalkyl 1h-indol-1-yl acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
| US7342039B2 (en) * | 2003-09-25 | 2008-03-11 | Wyeth | Substituted indole oximes |
| US7446201B2 (en) * | 2003-09-25 | 2008-11-04 | Wyeth | Substituted heteroaryl benzofuran acids |
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| US7442805B2 (en) * | 2003-09-25 | 2008-10-28 | Wyeth | Substituted sulfonamide-indoles |
| JP2007530603A (ja) * | 2004-03-30 | 2007-11-01 | デン コンゲリク ベテリネル−オク ランドボホイスコレ | プロテアーゼ阻害物質の遮断又は検出による癌治療及び癌治療効能予測の改善 |
| EP1794138A2 (en) * | 2004-08-23 | 2007-06-13 | Wyeth | Thiazolo-naphthyl acids as inhibitors of plasminogen activator inhibitor-1 |
| US7754747B2 (en) | 2004-08-23 | 2010-07-13 | Wyeth Llc | Oxazolo-naphthyl acids |
| JP2008510814A (ja) * | 2004-08-23 | 2008-04-10 | ワイス | Ｐａｉ−１阻害剤としてのピロロ−ナフチル酸 |
| BRPI0614340A2 (pt) * | 2005-08-17 | 2011-04-12 | Wyeth Corp | indóis substituìdos e métodos de seu uso |
| AR059629A1 (es) * | 2006-02-27 | 2008-04-16 | Wyeth Corp | Inhibidores del inhibidor del activador de plasminogeno (pai- 1) para el tratamiento de trastornos musculares |
| AU2007307597A1 (en) | 2006-10-12 | 2008-04-17 | Institute Of Medicinal Molecular Design. Inc. | Carboxylic acid derivatives |
| JP5253174B2 (ja) | 2006-10-12 | 2013-07-31 | 株式会社医薬分子設計研究所 | Ｎ−フェニルオキサミド酸誘導体 |
| JP5470046B2 (ja) | 2007-10-23 | 2014-04-16 | 株式会社医薬分子設計研究所 | Ｐａｉ−１産生抑制剤 |
| US8633245B2 (en) * | 2008-04-11 | 2014-01-21 | Institute Of Medicinal Molecular Design, Inc. | PAI-1 inhibitor |
| WO2009125606A1 (ja) | 2008-04-11 | 2009-10-15 | 株式会社医薬分子設計研究所 | Pai-1阻害剤 |
| RU2011121042A (ru) | 2008-11-26 | 2013-01-10 | Файв Прайм Терапеутикс, Инк. | Композиции и способы регулирования экспрессии коллагена и актина гладких мышц посредством serpine2 |
| US8614237B2 (en) | 2009-05-05 | 2013-12-24 | Sloan-Kettering Institute For Cancer Research | Benzofuran-4,5-diones as selective peptide deformylase inhibitors |
| CN102850451B (zh) * | 2011-06-29 | 2014-05-07 | 辽宁诺康生物制药有限责任公司 | 具有抑制纤溶酶活性的重组textilinin-1及其制备方法和应用 |
| JP6682008B2 (ja) | 2015-12-18 | 2020-04-15 | タレンゲン インターナショナル リミテッドＴａｌｅｎｇｅｎ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｌｉｍｉｔｅｄ | 糖尿病性腎症を予防及び治療するための方法 |
| CN106890324A (zh) * | 2015-12-18 | 2017-06-27 | 深圳瑞健生命科学研究院有限公司 | 一种预防和治疗糖尿病肾病的方法 |
| JP7175270B2 (ja) | 2016-12-15 | 2022-11-18 | タレンゲン インターナショナル リミテッド | グルカゴン、インスリンを正常なバランスに戻らせる方法 |
| CN114957176A (zh) * | 2022-07-01 | 2022-08-30 | 河南中医药大学第一附属医院 | 人血管紧张素转化酶抑制剂化合物和合成方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1464242A (en) | 1974-04-18 | 1977-02-09 | Smithkline Corp | Benzoyl benzofurans and compositions comprising them |
| US4024273A (en) * | 1974-06-20 | 1977-05-17 | Smithkline Corporation | Coronary vasodilator and anti-anginal compositions comprising substituted benzofurans and benzothiophenes and methods of producing coronary vasodilation and anti-anginal activity |
| ZA825413B (en) | 1981-08-26 | 1983-06-29 | Pfizer | Thromboxane synthetase inhibitors, processes for their production, and pharmaceutical compositions comprising them |
| ZA928276B (en) * | 1991-10-31 | 1993-05-06 | Daiichi Seiyaku Co | Aromatic amidine derivates and salts thereof. |
| US6756388B1 (en) | 1993-10-12 | 2004-06-29 | Pfizer Inc. | Benzothiophenes and related compounds as estrogen agonists |
| CA2134192A1 (en) | 1993-11-12 | 1995-05-13 | Michael L. Denney | 5, 6-bicyclic glycoprotein iib/iiia antagonists |
| CA2207141A1 (en) | 1996-07-15 | 1998-01-15 | David Thompson Berg | Benzothiophene compounds, and uses and formulations thereof |
| US6110963A (en) | 1998-05-12 | 2000-08-29 | American Home Products Corporation | Aryl-oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia |
-
2002
- 2002-06-10 TW TW091112529A patent/TWI240723B/zh not_active IP Right Cessation
- 2002-06-18 JP JP2003507076A patent/JP4476624B2/ja not_active Expired - Lifetime
- 2002-06-18 CA CA002449844A patent/CA2449844A1/en not_active Abandoned
- 2002-06-18 CN CNB028161874A patent/CN1308320C/zh not_active Expired - Fee Related
- 2002-06-18 EP EP02747904A patent/EP1401822A1/en not_active Withdrawn
- 2002-06-18 US US10/174,166 patent/US6599925B2/en not_active Expired - Fee Related
- 2002-06-18 WO PCT/US2002/019231 patent/WO2003000671A1/en not_active Ceased
- 2002-06-18 MX MXPA03011400A patent/MXPA03011400A/es active IP Right Grant
- 2002-06-18 BR BR0210532-2A patent/BR0210532A/pt not_active IP Right Cessation
- 2002-06-20 AR ARP020102314A patent/AR036100A1/es unknown
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| Publication number | Publication date |
|---|---|
| US6599925B2 (en) | 2003-07-29 |
| JP2004534824A (ja) | 2004-11-18 |
| MXPA03011400A (es) | 2004-04-05 |
| BR0210532A (pt) | 2004-06-22 |
| AR036100A1 (es) | 2004-08-11 |
| EP1401822A1 (en) | 2004-03-31 |
| CA2449844A1 (en) | 2003-01-03 |
| CN1308320C (zh) | 2007-04-04 |
| JP4476624B2 (ja) | 2010-06-09 |
| CN1543456A (zh) | 2004-11-03 |
| WO2003000671A1 (en) | 2003-01-03 |
| US20030018067A1 (en) | 2003-01-23 |
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