JP2010515689A - 第Ｘａ因子阻害剤としてのチオフェンカルボキサミド - Google Patents

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Publication number

JP2010515689A

JP2010515689A JP2009544989A JP2009544989A JP2010515689A JP 2010515689 A JP2010515689 A JP 2010515689A JP 2009544989 A JP2009544989 A JP 2009544989A JP 2009544989 A JP2009544989 A JP 2009544989A JP 2010515689 A JP2010515689 A JP 2010515689A

Authority

JP

Japan

Prior art keywords

methyl

carboxamide

chloro

phenyl

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Withdrawn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 6
• YNSCKPCDFIDINW-UHFFFAOYSA-N 3-[[2-[[1-[2-(dimethylamino)acetyl]-6-methoxy-4,4-dimethyl-2,3-dihydroquinolin-7-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]thiophene-2-carboxamide Chemical compound COC1=CC(C(CCN2C(=O)CN(C)C)(C)C)=C2C=C1NC(N=C1NC=CC1=1)=NC=1NC=1C=CSC=1C(N)=O YNSCKPCDFIDINW-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 219
• 238000000034 method Methods 0.000 claims abstract description 76
• 150000003839 salts Chemical class 0.000 claims abstract description 36
• 208000007536 Thrombosis Diseases 0.000 claims abstract description 19
• 239000000651 prodrug Substances 0.000 claims abstract description 13
• 229940002612 prodrug Drugs 0.000 claims abstract description 13
• 241000124008 Mammalia Species 0.000 claims abstract description 12
• 150000002148 esters Chemical class 0.000 claims abstract description 10
• 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 210
• 239000000203 mixture Substances 0.000 claims description 151
• -1 nitro, hydroxy Chemical group 0.000 claims description 66
• 125000000217 alkyl group Chemical group 0.000 claims description 61
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 30
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 239000001257 hydrogen Substances 0.000 claims description 27
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 150000002431 hydrogen Chemical class 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 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 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
• 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
• GXQKVIJVPKRVNL-UHFFFAOYSA-N 5-chloro-n-[[1-[4-[(2-methoxyacetyl)-methylamino]phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(N(C)C(=O)COC)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 GXQKVIJVPKRVNL-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
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• ZORMXYHAYUVIPO-UHFFFAOYSA-N n-[[1-[4-[(2-aminoacetyl)-methylamino]phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(N(C(=O)CN)C)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 ZORMXYHAYUVIPO-UHFFFAOYSA-N 0.000 claims description 5
• 230000001732 thrombotic effect Effects 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
• 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 4
• MVQHWEHSUWMMBG-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(4-methyl-1,4-diazepan-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCCN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 MVQHWEHSUWMMBG-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
• 206010053567 Coagulopathies Diseases 0.000 claims description 4
• KSGPQKDDCHVRJN-UHFFFAOYSA-N n-[[1-[4-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=C(F)C(N)=NC(=O)N1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 KSGPQKDDCHVRJN-UHFFFAOYSA-N 0.000 claims description 4
• 208000011580 syndromic disease Diseases 0.000 claims description 4
• 238000011282 treatment Methods 0.000 claims description 4
• OPZZSJCZTIEEPS-UHFFFAOYSA-N 4-[4-[4-[[(5-chlorothiophene-2-carbonyl)amino]methyl]triazol-1-yl]phenyl]-3-oxopiperazine-1-carboxamide Chemical compound O=C1CN(C(=O)N)CCN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 OPZZSJCZTIEEPS-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
• 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 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
• 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
• BRLSGRUWHGRACW-UHFFFAOYSA-N 5-chloro-n-[[1-[4-[3-(2-imidazol-1-ylethoxy)-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(OCCN3C=NC=C3)=CC=C2)=O)N=N1 BRLSGRUWHGRACW-UHFFFAOYSA-N 0.000 claims description 3
• 206010051055 Deep vein thrombosis Diseases 0.000 claims description 3
• 230000001404 mediated effect Effects 0.000 claims description 3
• BURYKUBLLMASQQ-UHFFFAOYSA-N n-[[1-[4-(4-amino-2-oxopyrimidin-1-yl)phenyl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound O=C1N=C(N)C=CN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 BURYKUBLLMASQQ-UHFFFAOYSA-N 0.000 claims description 3
• HNGLSEOYSMTFPC-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(methylamino)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(NC)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 HNGLSEOYSMTFPC-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 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
• 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
• 208000032109 Transient ischaemic attack Diseases 0.000 claims description 2
• 208000007814 Unstable Angina Diseases 0.000 claims description 2
• 208000015294 blood coagulation disease Diseases 0.000 claims description 2
• 230000004087 circulation Effects 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
• 210000002216 heart Anatomy 0.000 claims description 2
• 210000003709 heart valve Anatomy 0.000 claims description 2
• 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 2
• 208000010125 myocardial infarction Diseases 0.000 claims description 2
• 230000000414 obstructive effect Effects 0.000 claims description 2
• 230000002537 thrombolytic effect Effects 0.000 claims description 2
• 201000010875 transient cerebral ischemia Diseases 0.000 claims description 2
• NJRXIKONXNPCDT-UHFFFAOYSA-N 1-[5-[4-[[(5-chlorothiophene-2-carbonyl)amino]methyl]triazol-1-yl]pyridin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=N1 NJRXIKONXNPCDT-UHFFFAOYSA-N 0.000 claims 1
• QYYXSOFLPATEKV-UHFFFAOYSA-N 2-[[1-[4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methylcarbamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NCC1=CN(C=2C=CC(=CC=2)N2C(C=CC=C2)=O)N=N1 QYYXSOFLPATEKV-UHFFFAOYSA-N 0.000 claims 1
• BYDHUDDMOHWTIC-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(1h-indol-2-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=CC(=CC=2)C=2NC3=CC=CC=C3C=2)N=N1 BYDHUDDMOHWTIC-UHFFFAOYSA-N 0.000 claims 1
• SMDZRFHAANDFHX-UHFFFAOYSA-N 5-chloro-n-[[3-[6-(1,4-diazepan-1-yl)pyridin-3-yl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN=NN1C1=CC=C(N2CCNCCC2)N=C1 SMDZRFHAANDFHX-UHFFFAOYSA-N 0.000 claims 1
• 201000007023 Thrombotic Thrombocytopenic Purpura Diseases 0.000 claims 1
• AQAACCLDNLZFDY-UHFFFAOYSA-N n-[[1-(4-aminophenyl)imidazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(N)=CC=C1N1C=C(CNC(=O)C=2SC(Cl)=CC=2)N=C1 AQAACCLDNLZFDY-UHFFFAOYSA-N 0.000 claims 1
• NNZMKARGPSSTFW-UHFFFAOYSA-N n-[[1-(4-carbamoylphenyl)triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 NNZMKARGPSSTFW-UHFFFAOYSA-N 0.000 claims 1
• SYXHLVMJLBZSDX-UHFFFAOYSA-N n-[[1-[2-(3-oxopiperazin-1-yl)-4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)NCC(N=N1)=CN1C1=CC=C(N2C(C=CC=C2)=O)C=C1N1CCNC(=O)C1 SYXHLVMJLBZSDX-UHFFFAOYSA-N 0.000 claims 1
• KFLJDLSBGSQKIM-UHFFFAOYSA-N n-[[1-[4-(2-oxopyridin-1-yl)phenyl]imidazol-4-yl]methyl]acetamide Chemical compound C1=NC(CNC(=O)C)=CN1C1=CC=C(N2C(C=CC=C2)=O)C=C1 KFLJDLSBGSQKIM-UHFFFAOYSA-N 0.000 claims 1
• JUALGSPEHOKAJJ-UHFFFAOYSA-N n-[[1-[6-(azepan-1-yl)pyridin-3-yl]triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=NC(=CC=2)N2CCCCCC2)N=N1 JUALGSPEHOKAJJ-UHFFFAOYSA-N 0.000 claims 1
• AJKNTDUHCRDNSD-UHFFFAOYSA-N n-[[3-(4-carbamoylphenyl)triazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1N1C(CNC(=O)C=2SC(Cl)=CC=2)=CN=N1 AJKNTDUHCRDNSD-UHFFFAOYSA-N 0.000 claims 1
• 108010074860 Factor Xa Proteins 0.000 abstract description 53
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• 239000000243 solution Substances 0.000 description 49
• 235000019439 ethyl acetate Nutrition 0.000 description 44
• 0 CC(C)c1c(*)[n](*)c(S(C)C)n1 Chemical compound CC(C)c1c(*)[n](*)c(S(C)C)n1 0.000 description 41
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• 238000002953 preparative HPLC Methods 0.000 description 31
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 27
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• 239000011734 sodium Substances 0.000 description 24
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