JP2010515691A5 - - Google Patents
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- JP2010515691A5 JP2010515691A5 JP2009544997A JP2009544997A JP2010515691A5 JP 2010515691 A5 JP2010515691 A5 JP 2010515691A5 JP 2009544997 A JP2009544997 A JP 2009544997A JP 2009544997 A JP2009544997 A JP 2009544997A JP 2010515691 A5 JP2010515691 A5 JP 2010515691A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- carboxamide
- oxopyridin
- thiophene
- 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.)
- Withdrawn
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- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims description 230
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- -1 2- (2- (dimethylamino) pyridin-4-yl) -4- (2-oxopyridin-1 (2H) -yl) phenyl Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229940002612 prodrug Drugs 0.000 claims description 8
- 239000000651 prodrug Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 208000007536 Thrombosis Diseases 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 230000001732 thrombotic effect Effects 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 206010053567 Coagulopathies Diseases 0.000 claims description 4
- 206010047249 Venous thrombosis Diseases 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- RNAPSGUDJUEJMZ-UHFFFAOYSA-N 2-[2-[4-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-5-iodotriazol-1-yl]-5-(2-oxopyridin-1-yl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(N2C(C=CC=C2)=O)=CC=C1N(C=1I)N=NC=1CNC(=O)C1=CC=C(Cl)S1 RNAPSGUDJUEJMZ-UHFFFAOYSA-N 0.000 claims description 2
- SPAPHUPHMIKVDZ-UHFFFAOYSA-N 2-[2-[4-[[(5-chlorothiophene-2-carbonyl)amino]methyl]triazol-1-yl]-5-(2-oxopyridin-1-yl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 SPAPHUPHMIKVDZ-UHFFFAOYSA-N 0.000 claims description 2
- PFLYXVAFMLHSKC-UHFFFAOYSA-N 2-[4-[[(5-chlorothiophene-2-carbonyl)amino]methyl]triazol-1-yl]-5-(2-oxopyridin-1-yl)benzoic acid Chemical compound OC(=O)C1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 PFLYXVAFMLHSKC-UHFFFAOYSA-N 0.000 claims description 2
- WHOPIKZJDFGCKX-UHFFFAOYSA-N 2-aminoethyl [2-[4-[[(5-chlorothiophene-2-carbonyl)amino]methyl]triazol-1-yl]-5-(2-oxopyridin-1-yl)phenyl] sulfate Chemical compound NCCOS(=O)(=O)OC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 WHOPIKZJDFGCKX-UHFFFAOYSA-N 0.000 claims description 2
- UJYBUHTWJDKSJC-UHFFFAOYSA-N 5-chloro-n-[[1-[2-(1,1-dioxo-1,4-thiazinan-4-yl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)N2CCS(=O)(=O)CC2)N=N1 UJYBUHTWJDKSJC-UHFFFAOYSA-N 0.000 claims description 2
- XSNHVLSLMQSWQH-UHFFFAOYSA-N 5-chloro-n-[[1-[2-(1,2,4-oxadiazol-3-ylmethoxy)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)OCC2=NOC=N2)N=N1 XSNHVLSLMQSWQH-UHFFFAOYSA-N 0.000 claims description 2
- OVYIVNVDMCIUNI-UHFFFAOYSA-N 5-chloro-n-[[1-[2-(1h-imidazol-2-ylmethoxy)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)OCC=2NC=CN=2)N=N1 OVYIVNVDMCIUNI-UHFFFAOYSA-N 0.000 claims description 2
- BLHWKPVISAJAQQ-UHFFFAOYSA-N 5-chloro-n-[[1-[2-(2-fluoropyridin-4-yl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=NC(F)=CC(C=2C(=CC=C(C=2)N2C(C=CC=C2)=O)N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)=C1 BLHWKPVISAJAQQ-UHFFFAOYSA-N 0.000 claims description 2
- WJHTZWMEDODIJF-UHFFFAOYSA-N 5-chloro-n-[[1-[2-(2-hydroxyethylcarbamoyl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound OCCNC(=O)C1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 WJHTZWMEDODIJF-UHFFFAOYSA-N 0.000 claims description 2
- NEOXZNWTVKAXIP-UHFFFAOYSA-N 5-chloro-n-[[1-[2-(2-imidazol-1-ylethoxy)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)OCCN2C=NC=C2)N=N1 NEOXZNWTVKAXIP-UHFFFAOYSA-N 0.000 claims description 2
- HUUONFGOENHRFU-UHFFFAOYSA-N 5-chloro-n-[[1-[2-(2-methoxyethylcarbamoyl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound COCCNC(=O)C1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 HUUONFGOENHRFU-UHFFFAOYSA-N 0.000 claims description 2
- FQTJTUFCRYZMIX-UHFFFAOYSA-N 5-chloro-n-[[1-[2-(3-hydroxypropylcarbamoyl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound OCCCNC(=O)C1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 FQTJTUFCRYZMIX-UHFFFAOYSA-N 0.000 claims description 2
- MZRYTEKMYPLUDU-UHFFFAOYSA-N 5-chloro-n-[[1-[2-(4-ethanimidoylpiperazin-1-yl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(C(=N)C)CCN1C1=CC(N2C(C=CC=C2)=O)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 MZRYTEKMYPLUDU-UHFFFAOYSA-N 0.000 claims description 2
- VLAQTTQBCZIIFL-UHFFFAOYSA-N 5-chloro-n-[[1-[2-[2-(dimethylamino)ethylcarbamoyl]-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound CN(C)CCNC(=O)C1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 VLAQTTQBCZIIFL-UHFFFAOYSA-N 0.000 claims description 2
- RNJFIWMMRXASFB-UHFFFAOYSA-N 5-chloro-n-[[1-[2-[[1-(1h-imidazol-2-ylmethyl)imidazol-2-yl]methoxy]-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)OCC=2N(C=CN=2)CC=2NC=CN=2)N=N1 RNJFIWMMRXASFB-UHFFFAOYSA-N 0.000 claims description 2
- DIZKMQTVBARUCR-UHFFFAOYSA-N 5-chloro-n-[[1-[2-imidazol-1-yl-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)N2C=NC=C2)N=N1 DIZKMQTVBARUCR-UHFFFAOYSA-N 0.000 claims description 2
- YMRWUNXLYCIGGX-UHFFFAOYSA-N 5-chloro-n-[[1-[2-methylsulfonyl-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound CS(=O)(=O)C1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 YMRWUNXLYCIGGX-UHFFFAOYSA-N 0.000 claims description 2
- XKRCSXJLWJXDOS-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyridin-1-yl)-2-(1-oxo-1,4-thiazinan-4-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)N2CCS(=O)CC2)N=N1 XKRCSXJLWJXDOS-UHFFFAOYSA-N 0.000 claims description 2
- UOHVFFLKUIGZCY-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyridin-1-yl)-2-(2-pyrazol-1-ylethoxy)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)OCCN2N=CC=C2)N=N1 UOHVFFLKUIGZCY-UHFFFAOYSA-N 0.000 claims description 2
- BUFNUNLVIQUVFZ-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyridin-1-yl)-2-(2-pyrrol-1-ylethoxy)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)OCCN2C=CC=C2)N=N1 BUFNUNLVIQUVFZ-UHFFFAOYSA-N 0.000 claims description 2
- IDHCRUYQALEARV-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyridin-1-yl)-2-(2h-tetrazol-5-ylmethoxy)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)OCC=2NN=NN=2)N=N1 IDHCRUYQALEARV-UHFFFAOYSA-N 0.000 claims description 2
- OYCLMEWGBYSLLV-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyridin-1-yl)-2-(2h-tetrazol-5-ylmethylcarbamoyl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)C(=O)NCC=2NN=NN=2)N=N1 OYCLMEWGBYSLLV-UHFFFAOYSA-N 0.000 claims description 2
- MQWKGAAJZZEHOQ-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyridin-1-yl)-2-thiomorpholin-4-ylphenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)N2CCSCC2)N=N1 MQWKGAAJZZEHOQ-UHFFFAOYSA-N 0.000 claims description 2
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 2
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- 206010002388 Angina unstable Diseases 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 206010051055 Deep vein thrombosis Diseases 0.000 claims description 2
- 206010014498 Embolic stroke Diseases 0.000 claims description 2
- 206010062506 Heparin-induced thrombocytopenia Diseases 0.000 claims description 2
- 208000010378 Pulmonary Embolism Diseases 0.000 claims description 2
- 206010043647 Thrombotic Stroke Diseases 0.000 claims description 2
- 201000007023 Thrombotic Thrombocytopenic Purpura Diseases 0.000 claims description 2
- 208000007814 Unstable Angina Diseases 0.000 claims description 2
- KGDMTBHTTRQBPY-UHFFFAOYSA-N [2-[4-[[(5-chlorothiophene-2-carbonyl)amino]methyl]triazol-1-yl]-5-(2-oxopyridin-1-yl)phenyl] methyl sulfate Chemical compound COS(=O)(=O)OC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 KGDMTBHTTRQBPY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000003146 anticoagulant agent Substances 0.000 claims description 2
- 239000008280 blood Substances 0.000 claims description 2
- 210000004369 blood Anatomy 0.000 claims description 2
- 208000015294 blood coagulation disease Diseases 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000002490 cerebral effect Effects 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 230000035602 clotting Effects 0.000 claims description 2
- 238000007887 coronary angioplasty Methods 0.000 claims description 2
- 208000009190 disseminated intravascular coagulation Diseases 0.000 claims description 2
- 210000003709 heart valve Anatomy 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 2
- 230000000302 ischemic effect Effects 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- KVZRHSVORAEIEG-UHFFFAOYSA-N n-[2-[4-[[(5-chlorothiophene-2-carbonyl)amino]methyl]triazol-1-yl]-5-(2-oxopyridin-1-yl)phenyl]pyridine-3-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)NC(=O)C=2C=NC=CC=2)N=N1 KVZRHSVORAEIEG-UHFFFAOYSA-N 0.000 claims description 2
- GCLQQRKXNVPOJW-UHFFFAOYSA-N n-[2-[4-[[(5-chlorothiophene-2-carbonyl)amino]methyl]triazol-1-yl]-5-(2-oxopyridin-1-yl)phenyl]pyridine-4-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)NC(=O)C=2C=CN=CC=2)N=N1 GCLQQRKXNVPOJW-UHFFFAOYSA-N 0.000 claims description 2
- RZJXSNOVOLXJBO-UHFFFAOYSA-N n-[[1-[2-(1-acetylpiperidin-4-yl)oxy-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1CN(C(=O)C)CCC1OC1=CC(N2C(C=CC=C2)=O)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 RZJXSNOVOLXJBO-UHFFFAOYSA-N 0.000 claims description 2
- JZXHDNSXMMSTOY-UHFFFAOYSA-N n-[[1-[2-(1h-benzimidazol-2-ylmethoxy)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C(=CC(=CC=2)N2C(C=CC=C2)=O)OCC=2NC3=CC=CC=C3N=2)N=N1 JZXHDNSXMMSTOY-UHFFFAOYSA-N 0.000 claims description 2
- VACRWHFRVMTVCA-UHFFFAOYSA-N n-[[1-[2-(2-acetamidoethoxy)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound CC(=O)NCCOC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 VACRWHFRVMTVCA-UHFFFAOYSA-N 0.000 claims description 2
- SCWMGYMYSXTQKY-UHFFFAOYSA-N n-[[1-[2-(2-amino-2-oxoethoxy)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NC(=O)COC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 SCWMGYMYSXTQKY-UHFFFAOYSA-N 0.000 claims description 2
- QCFDXHLKEDHMDI-UHFFFAOYSA-N n-[[1-[2-(2-aminoethoxy)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NCCOC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 QCFDXHLKEDHMDI-UHFFFAOYSA-N 0.000 claims description 2
- LPKCMPYZKJQQFZ-UHFFFAOYSA-N n-[[1-[2-(2-aminoethylamino)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NCCNC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 LPKCMPYZKJQQFZ-UHFFFAOYSA-N 0.000 claims description 2
- ZIGAKSXOOMHFNW-UHFFFAOYSA-N n-[[1-[2-(2-aminoethylcarbamoyl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NCCNC(=O)C1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 ZIGAKSXOOMHFNW-UHFFFAOYSA-N 0.000 claims description 2
- DBDGYINKBIHKRQ-UHFFFAOYSA-N n-[[1-[2-(2-aminoethylsulfanyl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NCCSC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 DBDGYINKBIHKRQ-UHFFFAOYSA-N 0.000 claims description 2
- HBXKXXLALBFWPW-UHFFFAOYSA-N n-[[1-[2-(2-aminoethylsulfonyl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NCCS(=O)(=O)C1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 HBXKXXLALBFWPW-UHFFFAOYSA-N 0.000 claims description 2
- IHUSUCKZPNUTSF-UHFFFAOYSA-N n-[[1-[2-(2-aminopyridin-4-yl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=NC(N)=CC(C=2C(=CC=C(C=2)N2C(C=CC=C2)=O)N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)=C1 IHUSUCKZPNUTSF-UHFFFAOYSA-N 0.000 claims description 2
- VOBXKMMQZQFWQU-UHFFFAOYSA-N n-[[1-[2-(3-acetamidopropoxy)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound CC(=O)NCCCOC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 VOBXKMMQZQFWQU-UHFFFAOYSA-N 0.000 claims description 2
- BNEHTNGQXNAPHX-UHFFFAOYSA-N n-[[1-[2-(3-aminopropoxy)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NCCCOC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 BNEHTNGQXNAPHX-UHFFFAOYSA-N 0.000 claims description 2
- FOMKCVXPHJYHCW-UHFFFAOYSA-N n-[[1-[2-(3-aminopropylamino)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NCCCNC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 FOMKCVXPHJYHCW-UHFFFAOYSA-N 0.000 claims description 2
- KZYJZOMWQOUEMZ-UHFFFAOYSA-N n-[[1-[2-(3-aminopropylcarbamoyl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NCCCNC(=O)C1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 KZYJZOMWQOUEMZ-UHFFFAOYSA-N 0.000 claims description 2
- OZGDFHRVJPRWEE-UHFFFAOYSA-N n-[[1-[2-(4-acetamidopiperidin-1-yl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(N2C(C=CC=C2)=O)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 OZGDFHRVJPRWEE-UHFFFAOYSA-N 0.000 claims description 2
- HHYWFVBAPVNJQT-UHFFFAOYSA-N n-[[1-[2-(4-acetylpiperazin-1-yl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1CN(C(=O)C)CCN1C1=CC(N2C(C=CC=C2)=O)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 HHYWFVBAPVNJQT-UHFFFAOYSA-N 0.000 claims description 2
- AUQQCIFILJQHSS-UHFFFAOYSA-N n-[[1-[2-(4-aminopiperidin-1-yl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1CC(N)CCN1C1=CC(N2C(C=CC=C2)=O)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 AUQQCIFILJQHSS-UHFFFAOYSA-N 0.000 claims description 2
- BHCDLUZDTGTPID-UHFFFAOYSA-N n-[[1-[2-(6-aminopyridin-3-yl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=NC(N)=CC=C1C1=CC(N2C(C=CC=C2)=O)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 BHCDLUZDTGTPID-UHFFFAOYSA-N 0.000 claims description 2
- HZOZQPIZSDRVII-UHFFFAOYSA-N n-[[1-[2-(aminomethyl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NCC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 HZOZQPIZSDRVII-UHFFFAOYSA-N 0.000 claims description 2
- YIBZIJCJJZSDFN-UHFFFAOYSA-N n-[[1-[2-(carbamoylamino)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NC(=O)NC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 YIBZIJCJJZSDFN-UHFFFAOYSA-N 0.000 claims description 2
- ZARAXECKUXVCPF-UHFFFAOYSA-N n-[[1-[2-[(2-amino-2-oxoethyl)carbamoyl]-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NC(=O)CNC(=O)C1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 ZARAXECKUXVCPF-UHFFFAOYSA-N 0.000 claims description 2
- MZVSQKJPUJTKRH-UHFFFAOYSA-N n-[[1-[2-[(3-amino-3-oxopropyl)carbamoyl]-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NC(=O)CCNC(=O)C1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 MZVSQKJPUJTKRH-UHFFFAOYSA-N 0.000 claims description 2
- PJKKVHZDRQPCKI-UHFFFAOYSA-N n-[[1-[2-[2-(carbamoylamino)ethoxy]-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NC(=O)NCCOC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 PJKKVHZDRQPCKI-UHFFFAOYSA-N 0.000 claims description 2
- DWYATFBGDNAQPS-UHFFFAOYSA-N n-[[1-[2-[3-(carbamoylamino)propoxy]-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NC(=O)NCCCOC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 DWYATFBGDNAQPS-UHFFFAOYSA-N 0.000 claims description 2
- BIQAFAQZCXOWCP-UHFFFAOYSA-N n-[[1-[2-[4-(carbamoylamino)piperidin-1-yl]-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1CC(NC(=O)N)CCN1C1=CC(N2C(C=CC=C2)=O)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 BIQAFAQZCXOWCP-UHFFFAOYSA-N 0.000 claims description 2
- KTVRYBMKFYGATK-UHFFFAOYSA-N n-[[1-[2-acetamido-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound CC(=O)NC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 KTVRYBMKFYGATK-UHFFFAOYSA-N 0.000 claims description 2
- DOWRPERVGUTYJO-UHFFFAOYSA-N n-[[1-[2-amino-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NC1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 DOWRPERVGUTYJO-UHFFFAOYSA-N 0.000 claims description 2
- GPOSXKFQDIULGV-UHFFFAOYSA-N n-[[1-[2-carbamoyl-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NC(=O)C1=CC(N2C(C=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 GPOSXKFQDIULGV-UHFFFAOYSA-N 0.000 claims description 2
- 230000000414 obstructive effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 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
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 230000002537 thrombolytic effect Effects 0.000 claims description 2
- 230000001052 transient effect Effects 0.000 claims description 2
- JWCJYKXDVIUNSF-UHFFFAOYSA-N 1-[2-[4-[[(5-chlorothiophene-2-carbonyl)amino]methyl]triazol-1-yl]-5-(2-oxopyridin-1-yl)phenyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=CC(N2C(C=CC=C2)=O)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 JWCJYKXDVIUNSF-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
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| US88373407P | 2007-01-05 | 2007-01-05 | |
| PCT/US2008/050305 WO2008086226A2 (en) | 2007-01-05 | 2008-01-04 | Factor xa inhibitors |
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| JP2010515691A JP2010515691A (ja) | 2010-05-13 |
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| WO (1) | WO2008086226A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2401778C (en) | 2000-02-29 | 2010-12-21 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
| BRPI0512273A (pt) * | 2004-06-18 | 2008-02-19 | Millennium Pharm Inc | inibidores do fator xa |
| US7696352B2 (en) * | 2004-06-18 | 2010-04-13 | Millennium Pharmaceuticals, Inc. | Factor Xa inhibitors |
| US20090186810A1 (en) * | 2006-03-27 | 2009-07-23 | Portola Pharmaceuticals, Inc. | Potassium channel modulators and platelet procoagulant activity |
| EP2016072B1 (en) | 2006-05-05 | 2014-07-16 | Millennium Pharmaceuticals, Inc. | Factor xa inhibitors |
| WO2008057972A1 (en) * | 2006-11-02 | 2008-05-15 | Millennium Pharmaceuticals, Inc. | Methods of synthesizing pharmaceutical salts of a factor xa inhibitor |
| WO2008127682A2 (en) | 2007-04-13 | 2008-10-23 | Millennium Pharmaceuticals, Inc. | Combination anticoagulant therapy with a compound that acts as a factor xa inhibitor |
| EA020045B1 (ru) * | 2007-05-02 | 2014-08-29 | Портола Фармасьютиклз, Инк. | Комбинированная терапия соединением, проявляющим активность ингибитора рецептора адф на тромбоцитах |
| US8399494B2 (en) * | 2008-10-30 | 2013-03-19 | Merck Sharp & Dohme Corp. | 2,5-disubstituted phenyl carboxamide orexin receptor antagonists |
| CN104774176A (zh) | 2009-12-17 | 2015-07-15 | 米伦纽姆医药公司 | 合成Xa因子抑制剂的方法 |
| JP5796872B2 (ja) | 2009-12-17 | 2015-10-21 | ミレニアム ファーマシューティカルズ， インコーポレイテッドＭｉｌｌｅｎｎｉｕｍ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ． | 第Ｘａ因子阻害剤の結晶性塩 |
| WO2011075602A1 (en) | 2009-12-17 | 2011-06-23 | Millennium Pharmaceuticals, Inc. | Methods of preparing factor xa inhibitors and salts thereof |
| AR082804A1 (es) | 2010-09-01 | 2013-01-09 | Portola Pharm Inc | Formas cristalinas de un inhibidor del factor xa |
| TW201240664A (en) | 2010-09-01 | 2012-10-16 | Portola Pharm Inc | Methods and formulations of treating thrombosis with betrixaban and a P-glycoprotein inhibitor |
| CN102219753B (zh) * | 2011-04-21 | 2012-10-31 | 山东大学 | 一种三氮唑类化合物及其制备方法与应用 |
| US20150224091A1 (en) | 2011-08-31 | 2015-08-13 | Portola Pharmaceuticals, Inc. | Prevention and treatment of thrombosis in medically ill patients |
| MX2015000830A (es) | 2012-07-18 | 2015-10-26 | Sunshine Lake Pharma Co Ltd | Derivados heterociclicos nitrogenosos y su aplicacion en farmacos. |
| JP2016526538A (ja) | 2013-06-20 | 2016-09-05 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺ダニ剤及び殺虫剤としてのアリールスルフィド誘導体及びアリールスルホキシド誘導体 |
| ES2761571T3 (es) | 2013-06-20 | 2020-05-20 | Bayer Cropscience Ag | Derivados de arilsulfuro y arilsulfóxido como acaricidas e insecticidas |
| CN105517995B (zh) | 2013-07-08 | 2018-10-02 | 拜耳作物科学股份公司 | 作为农药的六元c-n键合的芳基硫化物和芳基硫氧化物衍生物 |
| EP3078378B1 (en) | 2015-04-08 | 2020-06-24 | Vaiomer | Use of factor xa inhibitors for regulating glycemia |
| CN107382836A (zh) * | 2017-08-04 | 2017-11-24 | 吴赣药业（苏州）有限公司 | 一种1‑(4‑氨基苯基)‑1h‑吡啶‑2‑酮的制备方法 |
| CN108129348B (zh) * | 2018-01-12 | 2019-11-01 | 南开大学 | 叠氮三氟甲氧基化合物及其合成方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6514977B1 (en) * | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
| US6844367B1 (en) * | 1999-09-17 | 2005-01-18 | Millennium Pharmaceuticals, Inc. | Benzamides and related inhibitors of factor Xa |
| DE19962924A1 (de) * | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
| CA2401778C (en) * | 2000-02-29 | 2010-12-21 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
| US7312235B2 (en) * | 2001-03-30 | 2007-12-25 | Millennium Pharmaceuticals, Inc. | Benzamide inhibitors of factor Xa |
| WO2003074501A1 (en) * | 2002-03-07 | 2003-09-12 | Sds Biotech K.K. | Substituted isoxazole alkylamine derivative and agri- and horticultural fungicide |
| DE10322469A1 (de) * | 2003-05-19 | 2004-12-16 | Bayer Healthcare Ag | Heterocyclische Verbindungen |
| DE602004024910D1 (de) * | 2003-10-09 | 2010-02-11 | Millennium Pharm Inc | Thioethersubstituierte benzamide als inhibitoren von faktor xa |
| BRPI0512273A (pt) * | 2004-06-18 | 2008-02-19 | Millennium Pharm Inc | inibidores do fator xa |
| US7696352B2 (en) * | 2004-06-18 | 2010-04-13 | Millennium Pharmaceuticals, Inc. | Factor Xa inhibitors |
| PT1948608E (pt) * | 2005-11-08 | 2012-05-24 | Millennium Pharm Inc | Novos sais farmacêuticos e polimorfos de um inibidor do fator xa |
| EP2016072B1 (en) * | 2006-05-05 | 2014-07-16 | Millennium Pharmaceuticals, Inc. | Factor xa inhibitors |
| CA2671502C (en) * | 2006-12-08 | 2017-01-24 | Millennium Pharmaceuticals, Inc. | Unit dose formulations and methods of treating thrombosis with an oral factor xa inhibitor |
| WO2008127682A2 (en) * | 2007-04-13 | 2008-10-23 | Millennium Pharmaceuticals, Inc. | Combination anticoagulant therapy with a compound that acts as a factor xa inhibitor |
| EA020045B1 (ru) * | 2007-05-02 | 2014-08-29 | Портола Фармасьютиклз, Инк. | Комбинированная терапия соединением, проявляющим активность ингибитора рецептора адф на тромбоцитах |
-
2008
- 2008-01-04 US US11/969,758 patent/US20080293704A1/en not_active Abandoned
- 2008-01-04 JP JP2009544997A patent/JP2010515691A/ja not_active Withdrawn
- 2008-01-04 CA CA002674924A patent/CA2674924A1/en not_active Abandoned
- 2008-01-04 AU AU2008205093A patent/AU2008205093A1/en not_active Abandoned
- 2008-01-04 WO PCT/US2008/050305 patent/WO2008086226A2/en not_active Ceased
- 2008-01-04 EP EP08713578A patent/EP2114930A2/en not_active Ceased
-
2010
- 2010-12-22 US US12/976,602 patent/US20110160196A1/en not_active Abandoned
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