JP2011520967A5 - - Google Patents
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- JP2011520967A5 JP2011520967A5 JP2011510610A JP2011510610A JP2011520967A5 JP 2011520967 A5 JP2011520967 A5 JP 2011520967A5 JP 2011510610 A JP2011510610 A JP 2011510610A JP 2011510610 A JP2011510610 A JP 2011510610A JP 2011520967 A5 JP2011520967 A5 JP 2011520967A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- aryl
- group
- phenyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 199
- -1 heterocyclenyl Chemical group 0.000 claims description 145
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- 125000003118 aryl group Chemical group 0.000 claims description 100
- 125000001072 heteroaryl group Chemical group 0.000 claims description 73
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
- 125000001424 substituent group Chemical group 0.000 claims description 61
- 125000000623 heterocyclic group Chemical group 0.000 claims description 56
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 55
- 229910052799 carbon Inorganic materials 0.000 claims description 52
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 39
- 125000001188 haloalkyl group Chemical group 0.000 claims description 32
- 208000035475 disorder Diseases 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 26
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 108010048049 Factor IXa Proteins 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- VIESAWGOYVNHLV-UHFFFAOYSA-N 1,3-dihydropyrrol-2-one Chemical compound O=C1CC=CN1 VIESAWGOYVNHLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 6
- 238000002560 therapeutic procedure Methods 0.000 claims 3
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 31
- 150000001721 carbon Chemical group 0.000 description 24
- 230000009424 thromboembolic effect Effects 0.000 description 22
- 150000002148 esters Chemical class 0.000 description 21
- 239000012453 solvate Substances 0.000 description 21
- 239000003112 inhibitor Substances 0.000 description 9
- 0 *C(C(*)N(C1=O)c2cc(cccc3)c3nc2O*)N1c1ccccc1 Chemical compound *C(C(*)N(C1=O)c2cc(cccc3)c3nc2O*)N1c1ccccc1 0.000 description 8
- 206010047249 Venous thrombosis Diseases 0.000 description 6
- 230000002526 effect on cardiovascular system Effects 0.000 description 6
- 230000000302 ischemic effect Effects 0.000 description 6
- 208000010125 myocardial infarction Diseases 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 208000004476 Acute Coronary Syndrome Diseases 0.000 description 3
- 206010002388 Angina unstable Diseases 0.000 description 3
- 200000000007 Arterial disease Diseases 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 3
- 206010003658 Atrial Fibrillation Diseases 0.000 description 3
- 239000005552 B01AC04 - Clopidogrel Substances 0.000 description 3
- 206010008092 Cerebral artery thrombosis Diseases 0.000 description 3
- 206010011091 Coronary artery thrombosis Diseases 0.000 description 3
- 206010051055 Deep vein thrombosis Diseases 0.000 description 3
- 206010014513 Embolism arterial Diseases 0.000 description 3
- 229940123849 Factor IXa inhibitor Drugs 0.000 description 3
- 229940124014 Factor VIIIa inhibitor Drugs 0.000 description 3
- 229940082863 Factor VIIa inhibitor Drugs 0.000 description 3
- 229940123583 Factor Xa inhibitor Drugs 0.000 description 3
- 102100037136 Proteinase-activated receptor 1 Human genes 0.000 description 3
- 101710121440 Proteinase-activated receptor 1 Proteins 0.000 description 3
- 208000010378 Pulmonary Embolism Diseases 0.000 description 3
- 206010037437 Pulmonary thrombosis Diseases 0.000 description 3
- 108091008103 RNA aptamers Proteins 0.000 description 3
- 206010063544 Renal embolism Diseases 0.000 description 3
- 101000712605 Theromyzon tessulatum Theromin Proteins 0.000 description 3
- 229940122388 Thrombin inhibitor Drugs 0.000 description 3
- 102000003790 Thrombin receptors Human genes 0.000 description 3
- 108090000166 Thrombin receptors Proteins 0.000 description 3
- 208000007536 Thrombosis Diseases 0.000 description 3
- 208000007814 Unstable Angina Diseases 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 239000003146 anticoagulant agent Substances 0.000 description 3
- 229940127219 anticoagulant drug Drugs 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 230000002612 cardiopulmonary effect Effects 0.000 description 3
- 230000002490 cerebral effect Effects 0.000 description 3
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 description 3
- 230000002860 competitive effect Effects 0.000 description 3
- 208000002528 coronary thrombosis Diseases 0.000 description 3
- 238000001631 haemodialysis Methods 0.000 description 3
- 230000000322 hemodialysis Effects 0.000 description 3
- 239000007943 implant Substances 0.000 description 3
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 3
- 201000010849 intracranial embolism Diseases 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 229940020573 plavix Drugs 0.000 description 3
- 230000000306 recurrent effect Effects 0.000 description 3
- 239000003868 thrombin inhibitor Substances 0.000 description 3
- 201000005060 thrombophlebitis Diseases 0.000 description 3
- 230000001052 transient effect Effects 0.000 description 3
- KKFZSALIMUSQSX-QPBDYMMBSA-N CCC1[C@H](C)C[C@H](C)C(C)C1 Chemical compound CCC1[C@H](C)C[C@H](C)C(C)C1 KKFZSALIMUSQSX-QPBDYMMBSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5431008P | 2008-05-19 | 2008-05-19 | |
| US61/054,310 | 2008-05-19 | ||
| PCT/US2009/044291 WO2009143039A2 (en) | 2008-05-19 | 2009-05-18 | Heterocyclic compounds as factor ixa inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011520967A JP2011520967A (ja) | 2011-07-21 |
| JP2011520967A5 true JP2011520967A5 (enExample) | 2012-06-07 |
| JP5504259B2 JP5504259B2 (ja) | 2014-05-28 |
Family
ID=41066042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011510610A Expired - Fee Related JP5504259B2 (ja) | 2008-05-19 | 2009-05-18 | 第ｉｘａ因子阻害剤としての複素環式化合物 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8148363B2 (enExample) |
| EP (2) | EP2300435A2 (enExample) |
| JP (1) | JP5504259B2 (enExample) |
| CN (1) | CN102099340A (enExample) |
| AR (1) | AR071823A1 (enExample) |
| CA (1) | CA2724430A1 (enExample) |
| CL (1) | CL2009001214A1 (enExample) |
| MX (1) | MX2010012635A (enExample) |
| PE (1) | PE20091972A1 (enExample) |
| TW (1) | TW201008930A (enExample) |
| WO (1) | WO2009143039A2 (enExample) |
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| MA33451B1 (fr) * | 2009-06-26 | 2012-07-03 | Novartis Ag | Dérivés d'imidazolidin-2-one 1,3-disubstitués en tant qu'inhibiteurs de cyp 17 |
| US8242284B1 (en) * | 2009-09-21 | 2012-08-14 | The United States Of America As Represented By The United States Department Of Energy | Anti-cancer agents based on 6-trifluoromethoxybenzimidazole derivatives and method of making |
| JP6155187B2 (ja) * | 2010-03-30 | 2017-06-28 | ヴァーセオン コーポレイション | トロンビンの阻害剤としての多置換芳香族化合物 |
| ES2626601T3 (es) * | 2010-06-28 | 2017-07-25 | Bayer Intellectual Property Gmbh | Compuestos heterocíclicos como pesticidas |
| WO2012003405A1 (en) | 2010-06-30 | 2012-01-05 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
| NZ609955A (en) | 2010-11-09 | 2015-05-29 | Ironwood Pharmaceuticals Inc | Sgc stimulators |
| EA023064B1 (ru) | 2011-04-28 | 2016-04-29 | Новартис Аг | ИНГИБИТОРЫ 17α-ГИДРОКСИЛАЗЫ/C-ЛИАЗЫ |
| EP2729150B1 (en) | 2011-07-08 | 2016-09-14 | Merck Sharp & Dohme Corp. | Factor ixa inhibitors |
| ES2882807T3 (es) | 2011-09-16 | 2021-12-02 | Novartis Ag | Heterociclil carboxamidas N-sustituidas |
| CN104066731B (zh) | 2011-12-27 | 2016-06-15 | 铁木医药有限公司 | 可用作sgc刺激剂的2-苄基、3-(嘧啶-2-基)取代的吡唑类 |
| CN102660253B (zh) * | 2012-03-07 | 2014-05-21 | 泰山医学院 | 一种吡唑啉衍生物类Ni2+荧光探针及其应用 |
| US9914727B2 (en) | 2012-12-19 | 2018-03-13 | Merck Sharp & Dohme Corp. | Factor IXa inhibitors |
| US9695198B2 (en) | 2012-12-19 | 2017-07-04 | Merck Sharp & Dohme Corp. | Factor IXa inhibitors |
| EP2934538B1 (en) * | 2012-12-19 | 2021-03-31 | Merck Sharp & Dohme Corp. | Factor ixa inhibitors |
| ES2791749T3 (es) | 2013-03-15 | 2020-11-05 | Verseon Corp | Halogenopirazoles como inhibidores de la trombina |
| WO2014145986A1 (en) | 2013-03-15 | 2014-09-18 | Verseon, Inc. | Multisubstituted aromatic compounds as serine protease inhibitors |
| WO2015160636A1 (en) | 2014-04-16 | 2015-10-22 | Merck Sharp & Dohme Corp. | Factor ixa inhibitors |
| US10266526B2 (en) * | 2014-09-10 | 2019-04-23 | Epizyme, Inc. | Substituted 1,2,3-triazoles as SMYD inhibitors for treating cancer |
| WO2016044645A1 (en) * | 2014-09-17 | 2016-03-24 | Elmaleh David R | Anticoagulant derivatives for cardiovascular imaging |
| KR20170048410A (ko) | 2014-09-17 | 2017-05-08 | 베르선 코포레이션 | 세린 프로테아제 저해제로서의 피라졸릴-치환된 피리돈 화합물 |
| US10314820B2 (en) | 2014-12-04 | 2019-06-11 | Procomcure Biotech Gmbh | Imidazole-based heterocyclic compounds |
| WO2016087616A1 (en) * | 2014-12-04 | 2016-06-09 | Procomcure Biotech Gmbh | Imidazole-based antimicrobial agents |
| WO2016133793A1 (en) * | 2015-02-16 | 2016-08-25 | Merck Sharp & Dohme Corp. | FACTOR IXa INHIBITORS |
| AU2016224974B2 (en) | 2015-02-27 | 2019-09-26 | Verseon Corporation | Substituted pyrazole compounds as serine protease inhibitors |
| KR20180132783A (ko) * | 2016-04-07 | 2018-12-12 | 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 | 단백질 조절제로서 유용한 헤테로사이클릭 아미드 |
| CN113549110B (zh) * | 2016-04-07 | 2024-08-16 | 葛兰素史密斯克莱知识产权发展有限公司 | 用作蛋白质调节剂的杂环酰胺 |
| EP3541381B1 (en) * | 2016-11-18 | 2022-12-28 | Merck Sharp & Dohme LLC | Inhibitors of factor xiia |
| WO2018175670A1 (en) | 2017-03-22 | 2018-09-27 | The Research Foundation For The State University Of New York | Matrix metalloproteinase-9 hemopexin domain inhibitors and methods of treatment using same |
| WO2019204447A1 (en) | 2018-04-17 | 2019-10-24 | The Regents Of The University Of Michigan | Inhibitors of platelet function and methods for use of the same |
| CN112457308B (zh) * | 2019-09-09 | 2024-01-02 | 上海长森药业有限公司 | 新型三环芳香杂环化合物，及其制备方法、药物组合物和应用 |
| EP4143183B1 (en) | 2020-04-29 | 2025-10-22 | Gasherbrum Bio, Inc. | Heterocyclic glp-1 agonists |
| WO2022028572A1 (en) | 2020-08-06 | 2022-02-10 | Gasherbrum Bio, Inc. | Heterocyclic glp-1 agonists |
| WO2022081573A1 (en) * | 2020-10-12 | 2022-04-21 | University Of Tennessee Research Foundation | Transient receptor potential canonical 3 inhibitors and methods of use thereof |
| CN116547279A (zh) * | 2020-10-13 | 2023-08-04 | 加舒布鲁姆生物公司 | 杂环glp-1激动剂 |
| CN114149371B (zh) * | 2021-11-26 | 2023-08-22 | 首都医科大学 | 四取代吡唑类化合物及其应用 |
| CN114478511B (zh) * | 2022-02-24 | 2023-06-20 | 中国药科大学 | 苯并恶唑类化合物及其制备方法、药物组合物和应用 |
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| CA2574147A1 (en) * | 2004-07-22 | 2006-02-09 | Linda Brockunier | Substituted pyrazoles, compositions containing such compounds and methods of use |
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| US20070197532A1 (en) * | 2005-11-18 | 2007-08-23 | Cao Sheldon X | Glucokinase activators |
| US7968683B1 (en) * | 2008-05-07 | 2011-06-28 | Schering Corporation | Factor IXa crystals, related complexes and methods |
| CA2724294A1 (en) * | 2008-05-16 | 2009-11-19 | Schering Corporation | Glucagon receptor antagonists, compositions, and methods for their use |
-
2009
- 2009-05-18 CN CN200980128238XA patent/CN102099340A/zh active Pending
- 2009-05-18 CA CA2724430A patent/CA2724430A1/en not_active Abandoned
- 2009-05-18 TW TW098116429A patent/TW201008930A/zh unknown
- 2009-05-18 CL CL2009001214A patent/CL2009001214A1/es unknown
- 2009-05-18 JP JP2011510610A patent/JP5504259B2/ja not_active Expired - Fee Related
- 2009-05-18 PE PE2009000694A patent/PE20091972A1/es not_active Application Discontinuation
- 2009-05-18 MX MX2010012635A patent/MX2010012635A/es active IP Right Grant
- 2009-05-18 AR ARP090101778A patent/AR071823A1/es not_active Application Discontinuation
- 2009-05-18 EP EP09751268A patent/EP2300435A2/en not_active Ceased
- 2009-05-18 WO PCT/US2009/044291 patent/WO2009143039A2/en not_active Ceased
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- 2009-05-18 EP EP14173412.9A patent/EP2805939B1/en not_active Not-in-force