JP2010515689A5 - - Google Patents
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- JP2010515689A5 JP2010515689A5 JP2009544989A JP2009544989A JP2010515689A5 JP 2010515689 A5 JP2010515689 A5 JP 2010515689A5 JP 2009544989 A JP2009544989 A JP 2009544989A JP 2009544989 A JP2009544989 A JP 2009544989A JP 2010515689 A5 JP2010515689 A5 JP 2010515689A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- carboxamide
- chloro
- phenyl
- 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- Withdrawn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 156
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- -1 nitro, hydroxy Chemical group 0.000 claims description 7
- 208000007536 Thrombosis Diseases 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 230000001732 thrombotic effect Effects 0.000 claims description 6
- 206010053567 Coagulopathies Diseases 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 206010047249 Venous thrombosis Diseases 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000008280 blood Substances 0.000 claims description 4
- 210000004369 blood Anatomy 0.000 claims description 4
- 150000002148 esters Chemical class 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
- 229940002612 prodrug Drugs 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 230000035602 clotting Effects 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 2
- 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 2
- 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 2
- 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 description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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
- 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 2
- 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 2
- 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 2
- 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 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
- 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 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
- 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
- 239000003146 anticoagulant agent Substances 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
- 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
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 2
- 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 2
- 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 2
- 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 description 2
- 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 description 2
- 230000000414 obstructive effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 230000002537 thrombolytic effect Effects 0.000 claims description 2
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/620,615 US7696352B2 (en) | 2004-06-18 | 2007-01-05 | Factor Xa inhibitors |
| PCT/US2008/050244 WO2008086188A2 (en) | 2007-01-05 | 2008-01-04 | Thiophene carboxamides as factor xa inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010515689A JP2010515689A (ja) | 2010-05-13 |
| JP2010515689A5 true JP2010515689A5 (enExample) | 2012-03-08 |
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| JP2009544989A Withdrawn JP2010515689A (ja) | 2007-01-05 | 2008-01-04 | 第Ｘａ因子阻害剤としてのチオフェンカルボキサミド |
Country Status (6)
| Country | Link |
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| US (2) | US7696352B2 (enExample) |
| EP (1) | EP2114928A2 (enExample) |
| JP (1) | JP2010515689A (enExample) |
| AU (1) | AU2008205143A1 (enExample) |
| CA (1) | CA2674843A1 (enExample) |
| WO (1) | WO2008086188A2 (enExample) |
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| WO2001064642A2 (en) | 2000-02-29 | 2001-09-07 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
| US7696352B2 (en) * | 2004-06-18 | 2010-04-13 | Millennium Pharmaceuticals, Inc. | Factor Xa inhibitors |
| KR101195801B1 (ko) | 2004-06-18 | 2012-11-05 | 밀레니엄 파머슈티컬스 인코퍼레이티드 | Ｘａ 인자 억제제 |
| AP2007004244A0 (en) | 2005-05-10 | 2007-12-31 | Intermune Inc | Method of modulating stress-activated protein kinase system |
| WO2007112367A2 (en) * | 2006-03-27 | 2007-10-04 | Portola Pharmaceuticals, Inc. | Potassium channel modulators and platelet procoagulant activity |
| EP2016072B1 (en) | 2006-05-05 | 2014-07-16 | Millennium Pharmaceuticals, Inc. | Factor xa inhibitors |
| EP2077995B1 (en) | 2006-11-02 | 2012-02-08 | Millennium Pharmaceuticals, Inc. | Methods of synthesizing pharmaceutical salts of a factor xa inhibitor |
| CA2674924A1 (en) * | 2007-01-05 | 2008-07-17 | Millennium Pharmaceuticals, Inc. | Factor xa inhibitors |
| EP2155195B1 (en) | 2007-04-13 | 2014-07-16 | Millennium Pharmaceuticals, Inc. | Combination anticoagulant therapy with a compound that acts as a factor Xa inhibitor |
| KR101509829B1 (ko) * | 2007-05-02 | 2015-04-06 | 포톨라 파마슈티컬스, 인코포레이티드 | 혈소판 ａｄｐ 수용체 억제제로 작용하는 화합물을 이용한 병용요법 |
| WO2009063029A2 (en) * | 2007-11-16 | 2009-05-22 | Boehringer Ingelheim International Gmbh | Substituted amides, manufacturing and use thereof as medicaments |
| EP2224809A4 (en) | 2007-11-27 | 2014-06-11 | Univ North Carolina State | INHIBITION OF BIOFILMS IN PLANTS WITH IMIDAZOLE DERIVATIVES |
| EP2296653B1 (en) | 2008-06-03 | 2016-01-27 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| WO2010001365A1 (en) * | 2008-07-04 | 2010-01-07 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Nitrogen heterocycle derivatives as proteasome modulators |
| WO2010077603A1 (en) * | 2008-12-08 | 2010-07-08 | North Carolina State University | Inhibition and dispersion of biofilms in plants with imidazole-triazole derivatives |
| US20120135997A1 (en) | 2009-07-17 | 2012-05-31 | Shionogi & Co., Ltd. | Pharmaceutical composition comprising a lactam or benzenesulfonamide compound |
| EP2513094B1 (en) * | 2009-12-17 | 2015-12-16 | Millennium Pharmaceuticals, Inc. | Crystalline salts of a factor xa inhibitor |
| JP5766204B2 (ja) | 2009-12-17 | 2015-08-19 | 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因子阻害剤の合成方法 |
| US8742120B2 (en) * | 2009-12-17 | 2014-06-03 | Millennium Pharmaceuticals, Inc. | Methods of preparing factor xa inhibitors and salts thereof |
| US20130096160A1 (en) * | 2010-04-14 | 2013-04-18 | Secretary, Department Of Health And Human Services | Arylthiazolyl piperidines and related compounds as modulators of survival motor neuron (smn) protein production |
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| 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 |
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| US6514977B1 (en) * | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
| GB9725244D0 (en) | 1997-11-29 | 1998-01-28 | Zeneca Ltd | Chemical compounds |
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| DE19962924A1 (de) * | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
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| DE10027151A1 (de) | 2000-05-31 | 2001-12-06 | Bayer Ag | Herbizide Mittel auf Basis von substituierten Carbonsäureamiden |
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| US6914058B2 (en) | 2002-01-18 | 2005-07-05 | Dr. Reddy's Laboratories, Limited | Antibacterial compounds: process for their preparation and pharmaceutical compositions containing them |
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| WO2004101531A1 (en) | 2003-04-29 | 2004-11-25 | Dr. Reddy's Laboratories Ltd. | Antiinfective 1,2,3-triazole derivatives, process for their preparation and pharmaceutical compositions containing them |
| DE10322469A1 (de) | 2003-05-19 | 2004-12-16 | Bayer Healthcare Ag | Heterocyclische Verbindungen |
| WO2004106329A2 (en) | 2003-06-03 | 2004-12-09 | Dr. Reddy's Laboratories Ltd. | Novel antiinfective compounds and their pharmaceutical compositions |
| US7199149B2 (en) | 2003-10-01 | 2007-04-03 | Bristol Myers Squibb Company | Monocyclic and bicyclic lactams as factor Xa inhibitors |
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| CN101304971B (zh) * | 2005-11-08 | 2011-09-07 | 米伦纽姆医药公司 | Xa因子抑制剂n-(5-氯-2-吡啶基)-2-[[4-[(二甲氨基)亚氨基甲基]苯甲酰基]氨基]-5-甲氧基-苯甲酰胺的医药盐和多晶型 |
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| KR101509829B1 (ko) * | 2007-05-02 | 2015-04-06 | 포톨라 파마슈티컬스, 인코포레이티드 | 혈소판 ａｄｐ 수용체 억제제로 작용하는 화합물을 이용한 병용요법 |
| KR102069498B1 (ko) * | 2007-09-28 | 2020-01-23 | 포톨라 파마슈티컬스, 인코포레이티드 | 인자 Ｘａ 저해제에 대한 안티도트 및 그것을 사용하는 방법 |
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-
2007
- 2007-01-05 US US11/620,615 patent/US7696352B2/en not_active Expired - Fee Related
-
2008
- 2008-01-04 WO PCT/US2008/050244 patent/WO2008086188A2/en not_active Ceased
- 2008-01-04 EP EP08705691A patent/EP2114928A2/en not_active Withdrawn
- 2008-01-04 CA CA002674843A patent/CA2674843A1/en not_active Abandoned
- 2008-01-04 AU AU2008205143A patent/AU2008205143A1/en not_active Abandoned
- 2008-01-04 JP JP2009544989A patent/JP2010515689A/ja not_active Withdrawn
-
2010
- 2010-01-29 US US12/697,135 patent/US20100234352A1/en not_active Abandoned
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