AU2008205143A1 - Thiophene carboxamides as Factor Xa inhibitors - Google Patents

Info

Publication number

AU2008205143A1

AU2008205143A1 AU2008205143A AU2008205143A AU2008205143A1 AU 2008205143 A1 AU2008205143 A1 AU 2008205143A1 AU 2008205143 A AU2008205143 A AU 2008205143A AU 2008205143 A AU2008205143 A AU 2008205143A AU 2008205143 A1 AU2008205143 A1 AU 2008205143A1

Authority

AU

Australia

Prior art keywords

methyl

carboxamide

chloro

thiophene

phenyl

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical class NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 title claims description 136
• 229940123583 Factor Xa inhibitor Drugs 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims description 214
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 177
• 239000000203 mixture Substances 0.000 claims description 163
• 238000000034 method Methods 0.000 claims description 72
• 150000003839 salts Chemical class 0.000 claims description 33
• GFWYXAZYVZGBIW-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyridin-1-yl)-2-(4-propan-2-ylpiperazin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(C(C)C)CCN1C1=CC(N2C(C=CC=C2)=O)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 GFWYXAZYVZGBIW-UHFFFAOYSA-N 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 20
• 208000007536 Thrombosis Diseases 0.000 claims description 16
• 239000000651 prodrug Substances 0.000 claims description 11
• 229940002612 prodrug Drugs 0.000 claims description 11
• 241000124008 Mammalia Species 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• VOHLLTDPNSKGFF-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(1-methyl-6-oxopyridazin-3-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(=O)N(C)N=C1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 VOHLLTDPNSKGFF-UHFFFAOYSA-N 0.000 claims description 8
• VGQLDWPXYKIISM-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyrimidin-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(N=CC=C2)=O)N=N1 VGQLDWPXYKIISM-UHFFFAOYSA-N 0.000 claims description 8
• 150000002148 esters Chemical class 0.000 claims description 8
• 230000002401 inhibitory effect Effects 0.000 claims description 6
• SNFVWEAZGAJSJP-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2,4-dimethoxypyrimidin-5-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound COC1=NC(OC)=NC=C1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 SNFVWEAZGAJSJP-UHFFFAOYSA-N 0.000 claims description 5
• RATVVOKWZYXAKP-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopiperazin-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(CNCC2)=O)N=N1 RATVVOKWZYXAKP-UHFFFAOYSA-N 0.000 claims description 5
• OOBGVAVGWJSNDQ-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyridin-1-yl)-2-piperazin-1-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)N2CCNCC2)N=N1 OOBGVAVGWJSNDQ-UHFFFAOYSA-N 0.000 claims description 5
• KIWAJECUKDAMTL-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(3-hydroxy-2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1C(O)=CC=CN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 KIWAJECUKDAMTL-UHFFFAOYSA-N 0.000 claims description 5
• KJJYGWAGSXMOCQ-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(6-oxo-1h-pyridazin-3-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=CC(=CC=2)C2=NNC(=O)C=C2)N=N1 KJJYGWAGSXMOCQ-UHFFFAOYSA-N 0.000 claims description 5
• 206010047249 Venous thrombosis Diseases 0.000 claims description 5
• 239000003146 anticoagulant agent Substances 0.000 claims description 5
• 210000004369 blood Anatomy 0.000 claims description 5
• 239000008280 blood Substances 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• JBMQUFWOIFKATH-UHFFFAOYSA-N 4-chloro-n-[[1-[4-(2-oxopyridin-1-yl)phenyl]imidazol-4-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CN(C=2C=CC(=CC=2)N2C(C=CC=C2)=O)C=N1 JBMQUFWOIFKATH-UHFFFAOYSA-N 0.000 claims description 4
• WVDGGELBAQPQRW-UHFFFAOYSA-N 5-chloro-N-[[1-[4-[3-[2-(2-methyl-2-propan-2-ylhydrazinyl)ethoxy]-2-oxopyridin-1-yl]phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound ClC1=CC=C(S1)C(=O)NCC=1N=NN(C1)C1=CC=C(C=C1)N1C(C(=CC=C1)OCCNN(C(C)C)C)=O WVDGGELBAQPQRW-UHFFFAOYSA-N 0.000 claims description 4
• RPMKFVQSNMNQHH-UHFFFAOYSA-N 5-chloro-n-[[1-(4-iodophenyl)imidazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=CC(I)=CC=2)C=N1 RPMKFVQSNMNQHH-UHFFFAOYSA-N 0.000 claims description 4
• RZDMJAVPTRNTMT-UHFFFAOYSA-N 5-chloro-n-[[1-[2-(4-ethylpiperazin-1-yl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(CC)CCN1C1=CC(N2C(C=CC=C2)=O)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 RZDMJAVPTRNTMT-UHFFFAOYSA-N 0.000 claims description 4
• YUMHMIRMMVSWBC-UHFFFAOYSA-N 5-chloro-n-[[1-[2-fluoro-4-(2-oxo-1,3-diazinan-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound FC1=CC(N2C(NCCC2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 YUMHMIRMMVSWBC-UHFFFAOYSA-N 0.000 claims description 4
• UXDFFJQWRALQBE-UHFFFAOYSA-N 5-chloro-n-[[1-[2-fluoro-4-(2-oxopyrazin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound FC1=CC(N2C(C=NC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 UXDFFJQWRALQBE-UHFFFAOYSA-N 0.000 claims description 4
• BWOIKMAHNJFFHD-UHFFFAOYSA-N 5-chloro-n-[[1-[2-fluoro-4-(2-oxopyrimidin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound FC1=CC(N2C(N=CC=C2)=O)=CC=C1N(N=N1)C=C1CNC(=O)C1=CC=C(Cl)S1 BWOIKMAHNJFFHD-UHFFFAOYSA-N 0.000 claims description 4
• SMHXSIQGMQVLFQ-UHFFFAOYSA-N 5-chloro-n-[[1-[2-fluoro-4-(3-methyl-2-oxo-1,3-diazinan-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1N(C)CCCN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C(F)=C1 SMHXSIQGMQVLFQ-UHFFFAOYSA-N 0.000 claims description 4
• YTEKDQYUNGLOSP-UHFFFAOYSA-N 5-chloro-n-[[1-[3-fluoro-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound FC1=CC(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)=CC=C1N1C=CC=CC1=O YTEKDQYUNGLOSP-UHFFFAOYSA-N 0.000 claims description 4
• OTKHCRXNHACOLQ-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(1-methyl-2-oxopyridin-3-yl)phenyl]imidazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1N(C)C=CC=C1C1=CC=C(N2C=C(CNC(=O)C=3SC(Cl)=CC=3)N=C2)C=C1 OTKHCRXNHACOLQ-UHFFFAOYSA-N 0.000 claims description 4
• ZRJOAXZQNPYXNB-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2,5-dihydropyrrole-1-carbonyl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=CC(=CC=2)C(=O)N2CC=CC2)N=N1 ZRJOAXZQNPYXNB-UHFFFAOYSA-N 0.000 claims description 4
• CPFRKRRZEKLLBO-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-hydroxyphenyl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound OC1=CC=CC=C1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 CPFRKRRZEKLLBO-UHFFFAOYSA-N 0.000 claims description 4
• SCBSYDLJTODSKA-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-methoxyphenyl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound COC1=CC=CC=C1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 SCBSYDLJTODSKA-UHFFFAOYSA-N 0.000 claims description 4
• XKITYJYGSAIICA-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-methoxypyridin-3-yl)phenyl]imidazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound COC1=NC=CC=C1C1=CC=C(N2C=C(CNC(=O)C=3SC(Cl)=CC=3)N=C2)C=C1 XKITYJYGSAIICA-UHFFFAOYSA-N 0.000 claims description 4
• RNXYUXZVUHHASO-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxo-1h-pyridin-3-yl)phenyl]imidazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=CC(=CC=2)C=2C(NC=CC=2)=O)C=N1 RNXYUXZVUHHASO-UHFFFAOYSA-N 0.000 claims description 4
• AGPUPLOVSPHBRW-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(5-hydroxy-2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=C(O)C=CC(=O)N1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 AGPUPLOVSPHBRW-UHFFFAOYSA-N 0.000 claims description 4
• BKFDAFZIOYPEMP-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(pyrrolidine-1-carbonyl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=CC(=CC=2)C(=O)N2CCCC2)N=N1 BKFDAFZIOYPEMP-UHFFFAOYSA-N 0.000 claims description 4
• ZRMFIQSCNUQWLS-UHFFFAOYSA-N 5-chloro-n-[[1-[4-[2-(trifluoromethoxy)phenyl]phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound FC(F)(F)OC1=CC=CC=C1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 ZRMFIQSCNUQWLS-UHFFFAOYSA-N 0.000 claims description 4
• SMCZJWLTTQNLJA-UHFFFAOYSA-N 5-chloro-n-[[1-[4-[2-oxo-3-(3-piperidin-1-ylpropoxy)pyridin-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(OCCCN3CCCCC3)=CC=C2)=O)N=N1 SMCZJWLTTQNLJA-UHFFFAOYSA-N 0.000 claims description 4
• VFELFOQINSNXLL-UHFFFAOYSA-N 5-chloro-n-[[1-[4-[3-(2-hydroxyethoxy)-2-oxopyridin-1-yl]phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1C(OCCO)=CC=CN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 VFELFOQINSNXLL-UHFFFAOYSA-N 0.000 claims description 4
• LOZXELVWDWEWTM-UHFFFAOYSA-N 5-chloro-n-[[1-[4-[3-(2-methoxyethoxy)-2-oxopyridin-1-yl]phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1C(OCCOC)=CC=CN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 LOZXELVWDWEWTM-UHFFFAOYSA-N 0.000 claims description 4
• ASZXNLMHOAGOJR-UHFFFAOYSA-N 5-chloro-n-[[1-[4-[3-(2-methylsulfanylethoxy)-2-oxopyridin-1-yl]phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1C(OCCSC)=CC=CN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 ASZXNLMHOAGOJR-UHFFFAOYSA-N 0.000 claims description 4
• ZKTRWQMFDRIDGG-UHFFFAOYSA-N 5-chloro-n-[[1-[4-[3-(2-methylsulfinylethoxy)-2-oxopyridin-1-yl]phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1C(OCCS(=O)C)=CC=CN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 ZKTRWQMFDRIDGG-UHFFFAOYSA-N 0.000 claims description 4
• IWLHUDYITNVHIQ-UHFFFAOYSA-N 5-chloro-n-[[1-[4-[3-(2-methylsulfonylethoxy)-2-oxopyridin-1-yl]phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1C(OCCS(=O)(=O)C)=CC=CN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 IWLHUDYITNVHIQ-UHFFFAOYSA-N 0.000 claims description 4
• QZQGTBIZNDAQRI-UHFFFAOYSA-N 5-chloro-n-[[1-[4-[[2-(dimethylamino)acetyl]-methylamino]phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(N(C)C(=O)CN(C)C)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 QZQGTBIZNDAQRI-UHFFFAOYSA-N 0.000 claims description 4
• PEELXIQJDHGSDS-UHFFFAOYSA-N 5-chloro-n-[[1-[4-[methyl(propanoyl)amino]phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(N(C)C(=O)CC)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 PEELXIQJDHGSDS-UHFFFAOYSA-N 0.000 claims description 4
• VRSYIZBWXCEJPG-UHFFFAOYSA-N 5-chloro-n-[[1-[5-(2-oxopyridin-1-yl)pyridin-2-yl]imidazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2N=CC(=CC=2)N2C(C=CC=C2)=O)C=N1 VRSYIZBWXCEJPG-UHFFFAOYSA-N 0.000 claims description 4
• LIRHNJNMAJTEEA-UHFFFAOYSA-N 5-chloro-n-[[1-[6-(2-oxopyridin-1-yl)pyridin-3-yl]imidazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=NC(=CC=2)N2C(C=CC=C2)=O)C=N1 LIRHNJNMAJTEEA-UHFFFAOYSA-N 0.000 claims description 4
• HROUVJXQXZSRLN-UHFFFAOYSA-N 5-chloro-n-[[1-methyl-2-[4-(2-oxopyridin-1-yl)phenyl]imidazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound N1=C(C=2C=CC(=CC=2)N2C(C=CC=C2)=O)N(C)C=C1CNC(=O)C1=CC=C(Cl)S1 HROUVJXQXZSRLN-UHFFFAOYSA-N 0.000 claims description 4
• PGRNITWVHXXQCP-UHFFFAOYSA-N 5-chloro-n-[[2-oxo-1-[4-(2-oxopyridin-1-yl)phenyl]pyridin-3-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC(C1=O)=CC=CN1C1=CC=C(N2C(C=CC=C2)=O)C=C1 PGRNITWVHXXQCP-UHFFFAOYSA-N 0.000 claims description 4
• WQAOPMBPGWPVQE-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(1-methyl-6-oxopyridazin-3-yl)phenyl]imidazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(=O)N(C)N=C1C1=CC=C(N2C(=CN=C2)CNC(=O)C=2SC(Cl)=CC=2)C=C1 WQAOPMBPGWPVQE-UHFFFAOYSA-N 0.000 claims description 4
• PMOZTAWKFUDWNR-UHFFFAOYSA-N 5-chloro-n-[[5-oxo-1-[4-(2-oxopyridin-1-yl)phenyl]-4h-pyrazol-3-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=NN(C=2C=CC(=CC=2)N2C(C=CC=C2)=O)C(=O)C1 PMOZTAWKFUDWNR-UHFFFAOYSA-N 0.000 claims description 4
• KWELSDAWLVMEML-UHFFFAOYSA-N 5-chloro-n-[[6-oxo-1-[4-(2-oxopyridin-1-yl)phenyl]pyridin-3-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)C=C1 KWELSDAWLVMEML-UHFFFAOYSA-N 0.000 claims description 4
• 230000015271 coagulation Effects 0.000 claims description 4
• 238000005345 coagulation Methods 0.000 claims description 4
• BIKDZWMWKDMDCS-UHFFFAOYSA-N ethyl n-[4-[4-[[(5-chlorothiophene-2-carbonyl)amino]methyl]triazol-1-yl]phenyl]-n-methylcarbamate Chemical compound C1=CC(N(C)C(=O)OCC)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 BIKDZWMWKDMDCS-UHFFFAOYSA-N 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• UIMRGRZXXLKNBL-UHFFFAOYSA-N n-[[1-[4-[acetyl(methyl)amino]phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(N(C(C)=O)C)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 UIMRGRZXXLKNBL-UHFFFAOYSA-N 0.000 claims description 4
• 230000001732 thrombotic effect Effects 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• ZSLGWBMIAAEWPB-UHFFFAOYSA-N 5-chloro-n-[[1-[3-methoxy-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound COC1=CC(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)=CC=C1N1C=CC=CC1=O ZSLGWBMIAAEWPB-UHFFFAOYSA-N 0.000 claims description 3
• OLWRNSOZNIWVCS-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2,3-dioxo-1h-pyrazin-4-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1C(O)=NC=CN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 OLWRNSOZNIWVCS-UHFFFAOYSA-N 0.000 claims description 3
• FEPGEIOLKWXESP-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2,4-dioxopyrimidin-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(NC(=O)C=C2)=O)N=N1 FEPGEIOLKWXESP-UHFFFAOYSA-N 0.000 claims description 3
• MHPRDGKAFQPPQU-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxo-4-propan-2-ylpiperazin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1CN(C(C)C)CCN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 MHPRDGKAFQPPQU-UHFFFAOYSA-N 0.000 claims description 3
• DXGLTXOTVXRFRR-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyrazin-1-yl)phenyl]pyrazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=CC(=CC=2)N2C(C=NC=C2)=O)N=C1 DXGLTXOTVXRFRR-UHFFFAOYSA-N 0.000 claims description 3
• SYSMSWCIQCHIEM-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyridin-1-yl)phenyl]pyrazol-3-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=NN(C=2C=CC(=CC=2)N2C(C=CC=C2)=O)C=C1 SYSMSWCIQCHIEM-UHFFFAOYSA-N 0.000 claims description 3
• PYOMIURPKNDCKB-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyridin-1-yl)phenyl]pyrazol-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)N=C1 PYOMIURPKNDCKB-UHFFFAOYSA-N 0.000 claims description 3
• GKQLTXHQRWOOSY-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyridin-1-yl)phenyl]pyrrol-3-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=C1 GKQLTXHQRWOOSY-UHFFFAOYSA-N 0.000 claims description 3
• BIVRWARUUGATHG-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(4-methyl-1,4-diazepan-1-yl)phenyl]pyrazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCCN1C1=CC=C(N2N=CC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 BIVRWARUUGATHG-UHFFFAOYSA-N 0.000 claims description 3
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