DK1937673T3 - Imidazolderivater som hæmmere af tafi-a - Google Patents

Imidazolderivater som hæmmere af tafi-a Download PDF

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DK1937673T3
DK1937673T3 DK06792327.6T DK06792327T DK1937673T3 DK 1937673 T3 DK1937673 T3 DK 1937673T3 DK 06792327 T DK06792327 T DK 06792327T DK 1937673 T3 DK1937673 T3 DK 1937673T3
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ylmethyl
imidazol
propionic acid
amino
pyridin
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Christopher Kallus
Holger Heitsch
Volkmar Wehner
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Sanofi Sa
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
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    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P11/16Central respiratory analeptics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/04Antineoplastic agents specific for metastasis
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/08Vasodilators for multiple indications
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/14Heterocyclic 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 three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04Ortho-condensed systems

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  • Diabetes (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Claims (6)

1. Forbindelse med formel I
(I) og/eller alle stereoisomere former af forbindelsen med formel I og/eller blandinger af disse former i ethvert forhold og/eller fysiologisk forligeligt salt af forbindelsen med formel I, idet U står for -(C1-C4)-alkylen-Het-Z, og idet U og Z tilsammen danner gruppen
og pyridyldelen i gruppen er usubstitueret eller er substitueret med methyl eller ethyl, n står for nul, R står for hydrogenatom eller -(C1-C4)-alkyl, V står for 1) hydrogenatom, 2) - (C1-C3)-alkyl eller 3) fluor, chlor eller brom, W står for - (C1-C3)-alkylen, X står for en aromatisk fem- til trettenleddet heterocyklus, idet heterocyklus er udvalgt af gruppen isoxazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, oxazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, thienopyridin eller thienyl, og heterocyklus er usubstitueret eller er substitueret en, to eller tre gange uafhængigt af hinanden med RI, Y står for 1) -(C3-C6)-cycloalkyl, idet cycloalkyl er usubstitueret eller er substitueret en, to eller tre gange uafhængigt af hinanden med RI, 2) - (C6-C14)-aryl, idet aryl er udvalgt af gruppen indanyl, naphthyl, phenyl eller tetrahydronaphthalenyl, idet aryl er usubstitueret eller er substitueret en, to eller tre gange uafhængigt af hinanden med RI, eller 3) står for heterocyklus, idet heterocyklus er udvalgt af gruppen 2,3-dihydro-benzo[1,4]dioxin, isoxazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, oxazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, thienopyridin eller thienyl, og Het er usubstitueret eller er substitueret en, to eller tre gange uafhængigt af hinanden med RI, og RI står for fluor, chlor, brom, - (C1-C4) -alkyl, - (C0-C4)-alkylen-phenyl, -0-CH3, -0-(C1-C4)-alkylen-phenyl, idet phenyl er usubstitueret eller er substitueret en eller to gange med fluor, chlor, brom eller -0-(C1-C4)-alkyl, for - (C3-C6) -cycloalkyl eller -CF3.
2. Forbindelse med formel I ifølge krav 1, kendetegnet ved, at forbindelsen 3-(6-amino-pyridin-3-yl)-2-{1-[5-(5-chlor-thiophen-2-yl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-[1-(5-phenyl-isoxazol-3-ylmethyl)-lH-imidazol-4-yl]-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-methoxy-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(5-chlor-thiophen-2-yl)- [1.3.4] thiadiazol-2-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-chlor-phenyl)- [1.3.4] thiadiazol-2-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-trifluormethyl-phenyl)- [1.2.4] oxadiazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(3-trifluormethyl-phenyl)- [1.2.4] oxadiazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-[1-(5-cyclopropyl- [1.3.4] thiadiazol-2-ylmethyl)-lH-imidazol- 4-yl]-propionsyre, 3-(6-amino-pyridin-3-yl)-2-[1-(5-phenyl-[1,2,4]oxadiazol-3-ylmethyl)-lH-imidazol-4-yl]-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[3-(3,4-dimethoxy-phenyl)- [1.2.4] oxadiazol-5-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)—2 —{1—[3-(4-methoxy-phenyl)- [1.2.4] oxadiazol-5-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)—2—{1-[3-(4'-isopropyl-phenyl)- [1.2.4] oxadiazol-5-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[3-(4'-tert-butyl-phenyl)- [1.2.4] oxadiazol-5-ylmethyl]-lH-imidazol-4-yl}-propionyure, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(3,4-dichlor-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[3-(4-methoxy-phenyl)- [1.2.4] oxadiazol-5-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-[1-(5-phenyl-[1,3,4]thiadiazol-2-ylmethyl)-lH-imidazol-4-yl]-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-methoxy-phenyl)- [1.3.4] thiadiazol-2-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)— 2 —{1—[5-(3,5-dimethyl-isoxazol-4-yl)- [1.2.4] oxadiazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-[1-(5-thiophen-2-yl-isoxazol-3-ylmethyl)-lH-imidazol-4-yl]-propionsyre, 3-(6-amino-pyridin-3-yl)-2-(1—{3 —[4-(4-chlor-benzyloxy)-phenyl]-[1,2,4]oxadiazol-5-ylmethyl}-lH-imidazol-4-yl)-propionsyre, 3-(6-amino-pyridin-3-yl)-2-[1-(4-phenyl-5-trifluormethyl-thiophen-2-ylmethyl)-lH-imidazol-4-yl]-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-brom-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-[1-(5-p-tolyl-isoxazol-3-ylmethyl)-lH-imidazol-4-yl]-propionsyre, 3-(6-amino-pyridin-3-yl)-2-(1 — {2 —[5-(5-chlor-thiophen-2-yl)-isoxazol-3-yl]-ethyl}-lH-imidazol-4-yl)-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-isobutyl-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-[1-(5-cyclopentyl- [1.3.4] thiadiazol-2-ylmethyl)-lH-imidazol-4-yl]-propionsyre, 3-(6-amino-pyridin-3-yl)-2-[1-(5-cyclobutyl-[1,3,4]thiadiazol- 2- ylmethyl)-lH-imidazol-4-yl]-propionsyre, 3- (6-amino-pyridin-3-yl)-2-[1-(5-cyclopropyl-isoxazol-3-ylmethyl)-lH-imidazol-4-yl]-propionsyre, 3-(6-amino-pyridin-3-yl)-2-[1-(5-cyclohexyl-isoxazol-3- ylmethyl)-lH-imidazol-4-yl]-propionsyre, 3-(6-amino-pyridin-3-yl)-2-[1-(5-cyclohexyl-[1,3,4]thiadiazol- 2- ylmethyl)-lH-imidazol-4-yl]-propionsyre, 3- (6-amino-pyridin-3-yl)-2-[1-(5-cyclobutyl-isoxazol-3-ylmethyl)-lH-imidazol-4-yl]-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-fluor-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-benzyl-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-tert-butyl-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-tert-butyl-2,6-dimethyl-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(2-chlor-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-sec-butyl-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-[1-(5-indan-5-yl-isoxazol-3-ylmethyl)-lH-imidazol-4-yl]-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-cyclopentyl-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-isopropyl-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-butyl-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-cyclohexyl-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)—2—{1—[5—(5,6,7,8-tetrahydro-naphthalen-2-yl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-propyl-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)-2-{1-[5-(4-phenethyl-phenyl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-pyridin-3-yl)— 2 —{1—[5-(2,3-dihydro- benzo[1,4]dioxin-6-yl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, (S)-3-(6-amino-pyridin-3-yl)-2-{1-[5-(5-chlor-thiophen-2-yl)- isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyreethylester, (R) -3-(6-amino-pyridin-3-yl)-2-{1-[5-(5-chlor-thiophen-2-yl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyreethylester, (S) -3-(6-amino-pyridin-3-yl)-2-{1-[5-(5-chlor-thiophen-2-yl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, (R)-3-(6-amino-pyridin-3-yl)-2-{1-[5-(5-chlor-thiophen-2-yl)-isoxazol-3-ylmethyl]-lH-imidazol-4-yl}-propionsyre, 3-(6-amino-5-methyl-pyridin-3-yl)-2-[1-(5-cyclopropyl- [1,3,4]thiadiazol-2-ylmethyl)-1 H-imidazol-4-yl]-propionsyre,
3. Fremgangsmåde til fremstilling af forbindelsen med formel I ifølge et af kravene 1 eller 2, kendetegnet ved, at man a) omsætter en forbindelse med formel III
(III) idet R, U og V har de i forbindelsen med formel I ifølge krav 1 nævnte betegnelser, med en forbindelse LG-W-X-Y, idet W, X og Y har de i forbindelsen med formel I ifølge krav 1 nævnte betegnelser, og LG er en fraspaltelig gruppe fra rækken -Cl, -Br, -I, -O-tosyl eller -O-mesyl, til en forbindelse med formel I ifølge krav I, idet R ikke er hydrogenatom, eller omsætter forbindelsen med formel I ifølge krav I, idet R ikke er hydrogenatom, ved hjælp af spaltning af esteren til en forbindelse med formel I, idet R betegner hydrogenatom, eller b) opsplitter en ifølge fremgangsmåden a) fremstillet forbindelse med formel I eller et egnet forstadie af formel I, som på basis af sin kemiske struktur optræder i enantiomere former, ved hjælp af saltdannelse med enantiomerrene syrer eller baser, kromatografi på chirale stationærfaser eller derivatisering ved hjælp af chirale, enantiomerrene forbindelser såsom aminosyrer, separation af de således opnåede diastereomerer og fraspaltning af de chirale hjælpegrupper i de rene enantiomerer, eller c) omdanner den ifølge fremgangsmåderne a) eller b) fremstillede forbindelse med formel I enten isoleret i fri form eller i tilfælde af forekomsten af syre eller basiske grupper til fysiologisk forligelige salte.
4. Lægemiddel, kendetegnet ved et aktivt indhold af i det mindste en forbindelse med formel I ifølge et af kravene 1 eller 2 sammen med et farmaceutisk egnet og fysiologisk forligeligt bærestof, tilsætningsstof og/eller andre aktiveller hjælpestoffer.
5. Anvendelse af forbindelsen med formel I ifølge et af kravene 1 eller 2 til fremstilling af et lægemiddel til profylakse, sekundærprævention eller terapi af alle sådanne sygdomme, som er forbundet med tromboser, embolier, hyperkoagulabilitet eller fibrotiske forandringer.
6. Anvendelse ifølge krav 5, kendetegnet ved, at det drejer sig om myokardieinfarkt, Angina pectoris og andre former for akut koronarsyndrom, slagtilfælde, perifere vaskulære sygdomme, dyb venetrombose, lungeemboli, emboliske eller trombotiske hændelser betinget af kardielle arrhytmier, kardiovaskulære hændelser såsom restenose efter revaskularisering og angioplasti og lignende indgreb såsom stentimplantationer og bypass-operationer, eller reduktion af tromboserisikoen efter kirurgiske indgreb såsom ved knæ- og hofteledsoperationer eller om dissemineret intravaskulær koagulation, sepsis og andre intravaskulære hændelser, som er forbundet med en infektion, atherosklerose, diabetes og det metaboliske syndrom og følgerne heraf, tumorvækst og tumormetastasering, betændte og degenerative ledsygdomme såsom rheumatoid artritis og arthrose, forstyrrelser i det hæmostatiske system såsom fibrinaflejringer, fibrotiske forandringer i lungerne såsom kronisk obstruktiv lungesygdom, adult respiratory distress syndrom eller fibrinaflejringer i øjet efter øjenoperationer eller hindring og/eller behandling af ardannelse.
DK06792327.6T 2005-10-15 2006-09-30 Imidazolderivater som hæmmere af tafi-a DK1937673T3 (da)

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DE102005049385A DE102005049385A1 (de) 2005-10-15 2005-10-15 Imidazolderivate als Inhibitoren von TAFIa
PCT/EP2006/009500 WO2007045339A1 (de) 2005-10-15 2006-09-30 Imidazolderivate als inhibitoren von tafi-a

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ES (1) ES2558874T3 (da)
HU (1) HUE026577T2 (da)
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PT (1) PT1937673E (da)
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US8044208B2 (en) 2011-10-25
US20080262028A1 (en) 2008-10-23
EP1937673A1 (de) 2008-07-02
JP2009511516A (ja) 2009-03-19
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