JP2010515691A - 第Ｘａ因子阻害剤 - Google Patents

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Publication number

JP2010515691A

JP2010515691A JP2009544997A JP2009544997A JP2010515691A JP 2010515691 A JP2010515691 A JP 2010515691A JP 2009544997 A JP2009544997 A JP 2009544997A JP 2009544997 A JP2009544997 A JP 2009544997A JP 2010515691 A JP2010515691 A JP 2010515691A

Authority

JP

Japan

Prior art keywords

methyl

phenyl

carboxamide

oxopyridin

thiophene

Prior art date

2007-01-05

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Withdrawn

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• 229940123583 Factor Xa inhibitor Drugs 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 385
• 238000000034 method Methods 0.000 claims abstract description 177
• 150000003839 salts Chemical class 0.000 claims abstract description 41
• 208000007536 Thrombosis Diseases 0.000 claims abstract description 20
• 239000000651 prodrug Substances 0.000 claims abstract description 17
• 229940002612 prodrug Drugs 0.000 claims abstract description 17
• 150000002148 esters Chemical class 0.000 claims abstract description 14
• 241000124008 Mammalia Species 0.000 claims abstract description 12
• 210000004369 blood Anatomy 0.000 claims abstract description 7
• 239000008280 blood Substances 0.000 claims abstract description 7
• DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims description 469
• 239000000460 chlorine Substances 0.000 claims description 178
• 239000000203 mixture Substances 0.000 claims description 143
• -1 2- (2- (dimethylamino) pyridin-4-yl) -4- (2-oxopyridin-1 (2H) -yl) phenyl Chemical group 0.000 claims description 82
• 125000000217 alkyl group Chemical group 0.000 claims description 46
• 125000001424 substituent group Chemical group 0.000 claims description 33
• 125000003118 aryl group Chemical group 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 125000000623 heterocyclic group Chemical group 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 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 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• 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 6
• 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 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 229910052727 yttrium Inorganic materials 0.000 claims description 6
• 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 5
• 206010047249 Venous thrombosis Diseases 0.000 claims description 5
• 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 5
• 239000003146 anticoagulant agent Substances 0.000 claims description 5
• 150000002431 hydrogen Chemical class 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• 230000001732 thrombotic effect Effects 0.000 claims description 5
• 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 description 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 206010053567 Coagulopathies Diseases 0.000 claims description 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
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