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- Withdrawn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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| 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)
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| EP (1) | EP2114928A2 (enExample) |
| JP (1) | JP2010515689A (enExample) |
| AU (1) | AU2008205143A1 (enExample) |
| CA (1) | CA2674843A1 (enExample) |
| WO (1) | WO2008086188A2 (enExample) |
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| AU2001245353A1 (en) | 2000-02-29 | 2001-09-12 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
| US7696352B2 (en) * | 2004-06-18 | 2010-04-13 | Millennium Pharmaceuticals, Inc. | Factor Xa inhibitors |
| CN1968922A (zh) | 2004-06-18 | 2007-05-23 | 米伦纽姆医药公司 | 因子xa抑制剂 |
| BRPI0608907A2 (pt) | 2005-05-10 | 2010-02-17 | Itermune Inc | método de modulação de sistema de proteìna cinase ativada por estresse |
| WO2007112367A2 (en) * | 2006-03-27 | 2007-10-04 | Portola Pharmaceuticals, Inc. | Potassium channel modulators and platelet procoagulant activity |
| TW200813017A (en) * | 2006-05-05 | 2008-03-16 | Millennium Pharm Inc | Factor XA inhibitors |
| PT2404906E (pt) * | 2006-11-02 | 2015-11-02 | Millennium Pharm Inc | Métodos de sintetizar sais farmacêuticos de um inibidor de fator xa |
| EP2114930A2 (en) * | 2007-01-05 | 2009-11-11 | Millennium Pharmaceuticals, Inc. | Factor xa inhibitors |
| AU2008239659B2 (en) * | 2007-04-13 | 2013-09-05 | Millennium Pharmaceuticals, Inc. | Combination anticoagulant therapy with a compound that acts as a factor Xa inhibitor |
| EP2586439A1 (en) * | 2007-05-02 | 2013-05-01 | Portola Pharmaceuticals, Inc. | Combination therapy with a compound acting as a platelet ADP receptor inhibitor |
| 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 |
| CA2728769A1 (en) * | 2008-07-04 | 2010-01-07 | Bruno Villoutreix | Nitrogen heterocycle derivatives as proteasome modulators |
| US20110294668A1 (en) | 2008-12-08 | 2011-12-01 | North Carolina State University | Inhibition and dispersion of biofilms in plants with imidazole-triazole derivatives |
| JPWO2011007819A1 (ja) | 2009-07-17 | 2012-12-27 | 塩野義製薬株式会社 | ラクタムまたはベンゼンスルホンアミド化合物を含有する医薬 |
| WO2011075602A1 (en) | 2009-12-17 | 2011-06-23 | Millennium Pharmaceuticals, Inc. | Methods of preparing factor xa inhibitors and salts thereof |
| 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 |
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| WO2011130515A1 (en) * | 2010-04-14 | 2011-10-20 | The United States Of America, As Represented By The 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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| CA2910873A1 (en) * | 2013-04-30 | 2014-11-06 | Glaxosmithkline Intellectual Property (No.2) Limited | Enhancer of zeste homolog 2 inhibitors |
| RU2692485C2 (ru) | 2014-04-02 | 2019-06-25 | Интермьюн, Инк. | Противофиброзные пиридиноны |
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| JP2020503336A (ja) * | 2016-12-29 | 2020-01-30 | ダウ アグロサイエンシィズ エルエルシー | 殺有害生物化合物の調製方法 |
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| US6514977B1 (en) | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
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| DE19962924A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
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| WO2003074501A1 (en) | 2002-03-07 | 2003-09-12 | Sds Biotech K.K. | Substituted isoxazole alkylamine derivative and agri- and horticultural fungicide |
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| CN1968922A (zh) * | 2004-06-18 | 2007-05-23 | 米伦纽姆医药公司 | 因子xa抑制剂 |
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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 AU AU2008205143A patent/AU2008205143A1/en not_active Abandoned
- 2008-01-04 EP EP08705691A patent/EP2114928A2/en not_active Withdrawn
- 2008-01-04 JP JP2009544989A patent/JP2010515689A/ja not_active Withdrawn
- 2008-01-04 CA CA002674843A patent/CA2674843A1/en not_active Abandoned
-
2010
- 2010-01-29 US US12/697,135 patent/US20100234352A1/en not_active Abandoned
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