CA2575411A1 - Thiazole derivatives having vap-1 inhibitory activity - Google Patents
Thiazole derivatives having vap-1 inhibitory activity Download PDFInfo
- Publication number
- CA2575411A1 CA2575411A1 CA002575411A CA2575411A CA2575411A1 CA 2575411 A1 CA2575411 A1 CA 2575411A1 CA 002575411 A CA002575411 A CA 002575411A CA 2575411 A CA2575411 A CA 2575411A CA 2575411 A1 CA2575411 A1 CA 2575411A1
- Authority
- CA
- Canada
- Prior art keywords
- amino
- methyl
- thiazol
- ethyl
- phenyl
- 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.)
- Abandoned
Links
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- 101000774560 Crotalus atrox Zinc metalloproteinase-disintegrin-like VAP1 Proteins 0.000 title 1
- 150000007979 thiazole derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 186
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- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
- 125000002947 alkylene group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 21
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- PQEFJKLVFBMTHJ-INIZCTEOSA-N (3s)-1-[[2-acetamido-4-[2-[4-(diaminomethylideneamino)phenyl]ethyl]-1,3-thiazol-5-yl]methyl]-n,n-dimethylpyrrolidine-3-carboxamide Chemical compound C1[C@@H](C(=O)N(C)C)CCN1CC1=C(CCC=2C=CC(NC(N)=N)=CC=2)N=C(NC(C)=O)S1 PQEFJKLVFBMTHJ-INIZCTEOSA-N 0.000 claims description 6
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- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
- LOYSBJJGNUPDMW-ZHACJKMWSA-N ethyl (e)-3-[2-acetamido-4-[2-(4-aminophenyl)ethyl]-1,3-thiazol-5-yl]prop-2-enoate Chemical compound S1C(NC(C)=O)=NC(CCC=2C=CC(N)=CC=2)=C1/C=C/C(=O)OCC LOYSBJJGNUPDMW-ZHACJKMWSA-N 0.000 description 2
- KJKCGBJTNCTYIR-WUKNDPDISA-N ethyl (e)-3-[2-acetamido-4-[2-[4-[[n,n'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]phenyl]ethyl]-1,3-thiazol-5-yl]prop-2-enoate Chemical compound S1C(NC(C)=O)=NC(CCC=2C=CC(N\C(NC(=O)OC(C)(C)C)=N\C(=O)OC(C)(C)C)=CC=2)=C1/C=C/C(=O)OCC KJKCGBJTNCTYIR-WUKNDPDISA-N 0.000 description 2
- HPEFLTBLLFQHLA-VAWYXSNFSA-N ethyl (e)-3-[4-[3-(2-acetamido-1,3-thiazol-4-yl)propyl]phenyl]prop-2-enoate Chemical compound C1=CC(/C=C/C(=O)OCC)=CC=C1CCCC1=CSC(NC(C)=O)=N1 HPEFLTBLLFQHLA-VAWYXSNFSA-N 0.000 description 2
- LGPRETRHIITWOD-YPKPFQOOSA-N ethyl (z)-3-[2-acetamido-4-[2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]ethyl]-1,3-thiazol-5-yl]prop-2-enoate Chemical compound S1C(NC(C)=O)=NC(CCC=2C=CC(NC(=O)OC(C)(C)C)=CC=2)=C1\C=C/C(=O)OCC LGPRETRHIITWOD-YPKPFQOOSA-N 0.000 description 2
- KMRBVHNWKFOXEC-UHFFFAOYSA-N ethyl 2-acetamido-4-(chloromethyl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(NC(C)=O)=NC=1CCl KMRBVHNWKFOXEC-UHFFFAOYSA-N 0.000 description 2
- OBIIWXHXIQXEHF-UHFFFAOYSA-N ethyl 2-acetamido-4-[2-(4-aminophenyl)ethyl]-1,3-thiazole-5-carboxylate Chemical compound S1C(NC(C)=O)=NC(CCC=2C=CC(N)=CC=2)=C1C(=O)OCC OBIIWXHXIQXEHF-UHFFFAOYSA-N 0.000 description 2
- NHVZOFMMHWHGKY-UHFFFAOYSA-N ethyl 2-acetamido-4-[2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]ethyl]-1,3-thiazole-5-carboxylate Chemical compound S1C(NC(C)=O)=NC(CCC=2C=CC(NC(=O)OC(C)(C)C)=CC=2)=C1C(=O)OCC NHVZOFMMHWHGKY-UHFFFAOYSA-N 0.000 description 2
- RJQOJTPJOSHXLD-UHFFFAOYSA-N ethyl 2-acetamido-5-[(3-methylsulfanylphenyl)methyl]-1,3-thiazole-4-carboxylate Chemical compound N1=C(NC(C)=O)SC(CC=2C=C(SC)C=CC=2)=C1C(=O)OCC RJQOJTPJOSHXLD-UHFFFAOYSA-N 0.000 description 2
- YSSDYOSYQQXGBA-UHFFFAOYSA-N ethyl 2-acetamido-5-[(4-methylsulfanylphenyl)methyl]-1,3-thiazole-4-carboxylate Chemical compound N1=C(NC(C)=O)SC(CC=2C=CC(SC)=CC=2)=C1C(=O)OCC YSSDYOSYQQXGBA-UHFFFAOYSA-N 0.000 description 2
- VMFKLNTXKXRZIC-UHFFFAOYSA-N ethyl 2-acetamido-5-benzyl-1,3-thiazole-4-carboxylate Chemical compound N1=C(NC(C)=O)SC(CC=2C=CC=CC=2)=C1C(=O)OCC VMFKLNTXKXRZIC-UHFFFAOYSA-N 0.000 description 2
- YYZWXTGTIZIHCH-UHFFFAOYSA-N ethyl 2-amino-5-[(4-methylsulfanylphenyl)methyl]-1,3-thiazole-4-carboxylate Chemical compound N1=C(N)SC(CC=2C=CC(SC)=CC=2)=C1C(=O)OCC YYZWXTGTIZIHCH-UHFFFAOYSA-N 0.000 description 2
- QEICSUTUPITSQL-UHFFFAOYSA-N ethyl 3-[4-[3-(2-acetamido-1,3-thiazol-4-yl)propyl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OCC)=CC=C1CCCC1=CSC(NC(C)=O)=N1 QEICSUTUPITSQL-UHFFFAOYSA-N 0.000 description 2
- CGNJOYUSPNGALU-UHFFFAOYSA-N ethyl 3-bromo-2-oxo-4-phenylbutanoate Chemical compound CCOC(=O)C(=O)C(Br)CC1=CC=CC=C1 CGNJOYUSPNGALU-UHFFFAOYSA-N 0.000 description 2
- IWDKIHJMBNTQIT-UHFFFAOYSA-N ethyl 3-bromo-4-(3-methylsulfanylphenyl)-2-oxobutanoate Chemical compound CCOC(=O)C(=O)C(Br)CC1=CC=CC(SC)=C1 IWDKIHJMBNTQIT-UHFFFAOYSA-N 0.000 description 2
- PUGRQVBMBJKFEQ-UHFFFAOYSA-N ethyl 3-bromo-4-(4-methylsulfanylphenyl)-2-oxobutanoate Chemical compound CCOC(=O)C(=O)C(Br)CC1=CC=C(SC)C=C1 PUGRQVBMBJKFEQ-UHFFFAOYSA-N 0.000 description 2
- XMIVTAOFQJBIGO-UHFFFAOYSA-N ethyl 4-(2-bromoacetyl)benzoate Chemical compound CCOC(=O)C1=CC=C(C(=O)CBr)C=C1 XMIVTAOFQJBIGO-UHFFFAOYSA-N 0.000 description 2
- BBKMEEMVJNOFIZ-UHFFFAOYSA-N ethyl 4-(3-methylsulfanylphenyl)-2-oxobutanoate Chemical compound CCOC(=O)C(=O)CCC1=CC=CC(SC)=C1 BBKMEEMVJNOFIZ-UHFFFAOYSA-N 0.000 description 2
- VUYHRTFKHBIJLA-UHFFFAOYSA-N ethyl 4-(4-methylsulfanylphenyl)-2-oxobutanoate Chemical compound CCOC(=O)C(=O)CCC1=CC=C(SC)C=C1 VUYHRTFKHBIJLA-UHFFFAOYSA-N 0.000 description 2
- FOGLNGQYERMUQC-UHFFFAOYSA-N ethyl 5-[2-[4-(2-acetamido-1,3-thiazol-4-yl)phenyl]ethyl]-1,3-oxazole-4-carboxylate Chemical compound N1=COC(CCC=2C=CC(=CC=2)C=2N=C(NC(C)=O)SC=2)=C1C(=O)OCC FOGLNGQYERMUQC-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229960005375 lutein Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- WQRJKUWDNDJFMP-OAQYLSRUSA-N methyl (3r)-1-[[2-acetamido-4-[2-[4-[[n,n'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]phenyl]ethyl]-1,3-thiazol-5-yl]methyl]pyrrolidine-3-carboxylate Chemical compound C1[C@H](C(=O)OC)CCN1CC1=C(CCC=2C=CC(N\C(NC(=O)OC(C)(C)C)=N\C(=O)OC(C)(C)C)=CC=2)N=C(NC(C)=O)S1 WQRJKUWDNDJFMP-OAQYLSRUSA-N 0.000 description 2
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- LXZAFOHXMUDYNN-UHFFFAOYSA-N methyl 3-(4-methylsulfanylphenyl)propanoate Chemical compound COC(=O)CCC1=CC=C(SC)C=C1 LXZAFOHXMUDYNN-UHFFFAOYSA-N 0.000 description 2
- ALIJCZHTMFUTAC-UHFFFAOYSA-N methyl 3-[4-[2-acetamido-5-[(4-methylsulfonylphenyl)methyl]-1,3-thiazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=C(CC=2C=CC(=CC=2)S(C)(=O)=O)SC(NC(C)=O)=N1 ALIJCZHTMFUTAC-UHFFFAOYSA-N 0.000 description 2
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- ZQKSUJFPHHRUPA-UHFFFAOYSA-N methyl 4-[3-(2-amino-1,3-thiazol-4-yl)propyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CCCC1=CSC(N)=N1 ZQKSUJFPHHRUPA-UHFFFAOYSA-N 0.000 description 2
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- TZRQZPMQUXEZMC-UHFFFAOYSA-N tert-butyl n-(2-bromoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCBr TZRQZPMQUXEZMC-UHFFFAOYSA-N 0.000 description 1
- NQXOWXNWMRRJAC-UHFFFAOYSA-N tert-butyl n-[2-[4-[2-(2-acetamido-1,3-thiazol-4-yl)ethyl]anilino]ethyl]carbamate Chemical compound S1C(NC(=O)C)=NC(CCC=2C=CC(NCCNC(=O)OC(C)(C)C)=CC=2)=C1 NQXOWXNWMRRJAC-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- A—HUMAN NECESSITIES
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- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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| AU2004904196 | 2004-07-27 | ||
| AU2004904196A AU2004904196A0 (en) | 2004-07-27 | Thiazole Derivatives Having VAP-1 Inhibitory Activity | |
| PCT/JP2005/014136 WO2006011631A2 (en) | 2004-07-27 | 2005-07-27 | Thiazole derivatives having vap-1 inhibitory activity |
Publications (1)
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| CA2575411A1 true CA2575411A1 (en) | 2006-02-02 |
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| CA002575411A Abandoned CA2575411A1 (en) | 2004-07-27 | 2005-07-27 | Thiazole derivatives having vap-1 inhibitory activity |
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| CA2641734A1 (en) | 2006-02-15 | 2007-08-23 | Abbott Laboratories | Acetyl-coa carboxylase (acc) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| WO2007095603A2 (en) * | 2006-02-15 | 2007-08-23 | Abbott Laboratories | Novel acetyl-coa carboxylase (acc) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| TW200913999A (en) * | 2007-06-25 | 2009-04-01 | R Tech Ueno Ltd | Composition for eye diseases acompany hypoxia or ischemia |
| KR20100096094A (ko) * | 2007-10-19 | 2010-09-01 | 가부시키가이샤 아루떼꾸 우에노 | 백내장 처치를 위한 의약 조성물 |
| US20090170770A1 (en) * | 2007-11-06 | 2009-07-02 | Ali Hafezi-Moghadam | Methods and compositions for treating conditions associated with angiogenesis using a vascular adhesion protein-1 (vap 1) inhibitor |
| ES2442298T3 (es) * | 2008-01-18 | 2014-02-11 | Allergan, Inc. | Agentes alfa 2 adrenérgicos selectivos de subtipo y métodos para usarlos |
| TWI437986B (zh) | 2008-01-31 | 2014-05-21 | R Tech Ueno Ltd | 噻唑衍生物及使用該衍生物作為ｖａｐ－１抑制劑之用途 |
| TWI490214B (zh) * | 2008-05-30 | 2015-07-01 | 艾德克 上野股份有限公司 | 苯或噻吩衍生物及該等作為ｖａｐ－１抑制劑之用途 |
| BRPI0920237A2 (pt) * | 2008-10-21 | 2015-12-29 | Metabolex Inc | agonistas do receptor aril gpr120 e suas respectivas utilizações |
| UA112154C2 (uk) | 2009-09-08 | 2016-08-10 | Біоті Терапіс Корп. | Застосування повністю людського анти-vap-1-антитіла для лікування фіброзних станів |
| FI20115234A0 (fi) | 2011-03-08 | 2011-03-08 | Biotie Therapies Corp | Uusia pyridatsinoni- ja pyridoniyhdisteitä |
| SG193307A1 (en) * | 2011-03-15 | 2013-10-30 | Astellas Pharma Inc | Guanidine compound |
| EP2781521A4 (en) | 2011-10-19 | 2015-03-04 | Kowa Co | NOVEL COMPOUND OF SPIROINDOLINE AND THERAPEUTIC AGENT CONTAINING THE SAME |
| CA2915163A1 (en) | 2013-06-12 | 2014-12-18 | Proximagen Limited | New therapeutic uses of enzyme inhibitors |
| WO2015159112A1 (en) | 2014-04-15 | 2015-10-22 | Pécsi Tudományegyetem | Semicarbazide-sensitive amine oxidase inhibitors for use as analgesics in traumatic neuropathy and neurogenic inflammation |
| WO2015189534A1 (en) | 2014-06-12 | 2015-12-17 | Proximagen Limited | Vap-1 inhibitors for treating muscular dystrophy |
| CN104478828B (zh) * | 2014-12-10 | 2016-07-06 | 漳州片仔癀药业股份有限公司 | 2-氨基-7-取代苯并噻唑类化合物及其制备方法与用途 |
| JOP20200093A1 (ar) | 2015-01-09 | 2017-06-16 | Kyowa Kirin Co Ltd | طريقة لإنتاج مشتق ثيازول |
| JP2018076236A (ja) | 2015-06-05 | 2018-05-17 | 株式会社アールテック・ウエノ | がんを処置するための医薬組成物 |
| JP6809464B2 (ja) | 2015-08-06 | 2021-01-06 | 宇部興産株式会社 | 置換グアニジン誘導体 |
| EP3386494A1 (en) | 2015-12-07 | 2018-10-17 | Benevolentai Cambridge Limited | Vap-1 inhibitors for treating pain |
| AU2017262707B2 (en) * | 2016-05-12 | 2020-11-19 | Boehringer Ingelheim International Gmbh | Pyridinyl derivatives, pharmaceutical compositions and uses thereof as AOC3 inhibitors |
| HUE058181T2 (hu) | 2016-12-28 | 2022-07-28 | Ube Industries | Subsztituált guanidin vegyület |
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| US4511574A (en) * | 1981-01-08 | 1985-04-16 | Mitsui Toatsu Kagaku Kabushiki Kaisha | N-(4-Phenyl-2-thiazolyl)carbamate derivatives |
| US4699928A (en) * | 1984-07-13 | 1987-10-13 | Merrell Dow Pharmaceuticals Inc. | Fluoroallylamine derivatives |
| IT1181871B (it) * | 1985-04-01 | 1987-09-30 | Consiglio Nazionale Ricerche | Inibitori selettivi delle benzilamminossidasi rispetto ad altre amminossidasi |
| US4650907A (en) * | 1985-12-05 | 1987-03-17 | Merrell Dow Pharmaceuticals Inc. | Nonaromatic fluoroallylamine MAO inhibitors |
| US4916151A (en) * | 1985-12-05 | 1990-04-10 | Merrell Dow Pharmaceuticals Inc. | Method of treating parkinson's syndrome |
| US4943593A (en) * | 1988-02-25 | 1990-07-24 | Merrell Dow Pharmaceuticals Inc. | Inhibitors of lysyl oxidase |
| US4965288A (en) * | 1988-02-25 | 1990-10-23 | Merrell Dow Pharmaceuticals Inc. | Inhibitors of lysyl oxidase |
| US5021456A (en) * | 1988-02-25 | 1991-06-04 | Merrell Dow Pharmaceuticals Inc. | Inhibitors of lysyl oxidase |
| US5059814A (en) * | 1988-11-30 | 1991-10-22 | The California Institute Of Technology | Winner-take-all circuits for neural computing systems |
| JPH0848664A (ja) * | 1994-08-05 | 1996-02-20 | Hisamitsu Pharmaceut Co Inc | 新規なグアニジノ安息香酸エステル誘導体 |
| GB9506188D0 (en) * | 1995-03-27 | 1995-05-17 | Fujisawa Pharmaceutical Co | Amidine derivatives |
| WO2002002090A2 (en) * | 2000-07-05 | 2002-01-10 | Biotie Therapies Corp. | Inhibitors of copper-containing amine oxidases |
| AU2002214505A1 (en) * | 2000-11-09 | 2002-05-21 | Biovitrum Ab | New use of 4, 5, 6, 7-tetrahydroimidazo-(4,5-c)pyridine derivatives |
| TWI336696B (en) * | 2003-01-27 | 2011-02-01 | Astellas Pharma Inc | Thiazole derivatives |
| US20060229346A1 (en) * | 2003-03-31 | 2006-10-12 | Sucampo Ag | Method for treating vascular hyperpermeable disease |
| CN1933833B (zh) * | 2004-03-18 | 2011-09-07 | 株式会社·R-技术上野 | 含有噻唑衍生物的含水组合物 |
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2005
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- 2005-07-27 AT AT05768525T patent/ATE427941T1/de not_active IP Right Cessation
- 2005-07-27 US US11/572,772 patent/US20070254931A1/en not_active Abandoned
- 2005-07-27 CN CNA200580031703XA patent/CN101031555A/zh active Pending
- 2005-07-27 WO PCT/JP2005/014136 patent/WO2006011631A2/en active Application Filing
- 2005-07-27 CA CA002575411A patent/CA2575411A1/en not_active Abandoned
- 2005-07-27 DE DE602005013793T patent/DE602005013793D1/de active Active
- 2005-07-27 KR KR1020077004487A patent/KR20070050932A/ko not_active Application Discontinuation
- 2005-07-27 EP EP05768525A patent/EP1786792B1/en not_active Not-in-force
- 2005-07-27 ES ES05768525T patent/ES2324922T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ES2324922T3 (es) | 2009-08-19 |
| JP4978464B2 (ja) | 2012-07-18 |
| WO2006011631A3 (en) | 2006-04-20 |
| EP1786792A2 (en) | 2007-05-23 |
| US20070254931A1 (en) | 2007-11-01 |
| DE602005013793D1 (de) | 2009-05-20 |
| KR20070050932A (ko) | 2007-05-16 |
| CN101031555A (zh) | 2007-09-05 |
| JP2008508188A (ja) | 2008-03-21 |
| ATE427941T1 (de) | 2009-04-15 |
| EP1786792B1 (en) | 2009-04-08 |
| WO2006011631A2 (en) | 2006-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20130729 |