RU2017112739A - Пиразолил-замещенные пиридоновые соединения как ингибиторы сериновых протеаз - Google Patents
Пиразолил-замещенные пиридоновые соединения как ингибиторы сериновых протеаз Download PDFInfo
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- RU2017112739A RU2017112739A RU2017112739A RU2017112739A RU2017112739A RU 2017112739 A RU2017112739 A RU 2017112739A RU 2017112739 A RU2017112739 A RU 2017112739A RU 2017112739 A RU2017112739 A RU 2017112739A RU 2017112739 A RU2017112739 A RU 2017112739A
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- Russia
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- substituted
- unsubstituted
- methyl
- chlorothiophen
- dihydropyridin
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- -1 Pyrazolyl-Substituted Pyridone Compounds Chemical class 0.000 title claims 27
- 102000012479 Serine Proteases Human genes 0.000 title 1
- 108010022999 Serine Proteases Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 33
- 150000001875 compounds Chemical class 0.000 claims 32
- 208000007536 Thrombosis Diseases 0.000 claims 27
- 125000003118 aryl group Chemical group 0.000 claims 20
- 208000035475 disorder Diseases 0.000 claims 20
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 201000010099 disease Diseases 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000004404 heteroalkyl group Chemical group 0.000 claims 9
- 208000005189 Embolism Diseases 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 7
- 210000001367 artery Anatomy 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- 208000001435 Thromboembolism Diseases 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 102000001399 Kallikrein Human genes 0.000 claims 5
- 108060005987 Kallikrein Proteins 0.000 claims 5
- 125000004474 heteroalkylene group Chemical group 0.000 claims 5
- 206010014522 Embolism venous Diseases 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
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- 208000004043 venous thromboembolism Diseases 0.000 claims 4
- 206010003658 Atrial Fibrillation Diseases 0.000 claims 3
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- 230000001269 cardiogenic effect Effects 0.000 claims 3
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 3
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- 239000008194 pharmaceutical composition Substances 0.000 claims 3
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
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- 206010051055 Deep vein thrombosis Diseases 0.000 claims 2
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- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
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- 229910052717 sulfur Inorganic materials 0.000 claims 2
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- UIONAHGDXCLOGM-UHFFFAOYSA-N 3-[5-[(5-chlorothiophen-2-yl)methylamino]-1-(2,2-dimethylpropanoyl)pyrazol-3-yl]-5-morpholin-4-yl-1H-pyridin-2-one Chemical compound CC(C)(C)C(=O)N1N=C(C=C1NCC1=CC=C(Cl)S1)C1=CC(=CNC1=O)N1CCOCC1 UIONAHGDXCLOGM-UHFFFAOYSA-N 0.000 claims 1
- YTRWFQHACQRPHX-UHFFFAOYSA-N 3-[5-[(5-chlorothiophen-2-yl)methylamino]-1-(2-methoxybenzoyl)pyrazol-3-yl]-5-pyridin-3-yl-1H-pyridin-2-one Chemical compound ClC1=CC=C(S1)CNC1=CC(=NN1C(C1=C(C=CC=C1)OC)=O)C=1C(NC=C(C=1)C=1C=NC=CC=1)=O YTRWFQHACQRPHX-UHFFFAOYSA-N 0.000 claims 1
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- HHXBRHADWSLBRI-UHFFFAOYSA-N 5-[5-[(5-chlorothiophen-2-yl)methylamino]-1-(2,2-dimethylpropanoyl)pyrazol-3-yl]-3-pyridin-3-yl-1H-pyridin-2-one Chemical compound ClC1=CC=C(S1)CNC1=CC(=NN1C(C(C)(C)C)=O)C=1C=C(C(NC=1)=O)C=1C=NC=CC=1 HHXBRHADWSLBRI-UHFFFAOYSA-N 0.000 claims 1
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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| MD3464271T2 (ro) | 2016-05-31 | 2020-08-31 | Kalvista Pharmaceuticals Ltd | Derivați de pirazol în calitate de inhibitori ai kaliсreinei plasmatice |
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| JP7037507B2 (ja) * | 2017-01-26 | 2022-03-16 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
| EP3612522A4 (en) * | 2017-04-18 | 2021-07-07 | Celgene Quanticel Research, Inc. | THERAPEUTIC COMPOUNDS |
| HUE057912T2 (hu) | 2017-11-29 | 2022-06-28 | Kalvista Pharmaceuticals Ltd | Plazma kallikrein inhibitort tartalmazó dózisformák |
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| CN110386932A (zh) | 2018-04-20 | 2019-10-29 | 艾科思莱德制药公司 | 用于抗肿瘤疗法中的双重atm和dna-pk抑制剂 |
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| CN110467601B (zh) * | 2019-08-29 | 2021-07-02 | 杭州市西溪医院 | 一种吡唑联吡啶酮类化合物、中间体及其制备方法及应用 |
| DE102020103516B4 (de) | 2020-02-11 | 2023-12-07 | Universität Zu Lübeck | Antivirale Wirkstoffe mit breiter Aktivität |
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Family Cites Families (118)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE627393A (enExample) | 1962-01-23 | |||
| BE793955A (fr) | 1972-01-15 | 1973-07-12 | Merck Patent Gmbh | Arylpiperazines et leur procede de preparation |
| DE2409753A1 (de) | 1974-03-01 | 1975-09-11 | Basf Ag | Substituierte pyrazole |
| US4256108A (en) | 1977-04-07 | 1981-03-17 | Alza Corporation | Microporous-semipermeable laminated osmotic system |
| US4160452A (en) | 1977-04-07 | 1979-07-10 | Alza Corporation | Osmotic system having laminated wall comprising semipermeable lamina and microporous lamina |
| US4265874A (en) | 1980-04-25 | 1981-05-05 | Alza Corporation | Method of delivering drug with aid of effervescent activity generated in environment of use |
| US4911920A (en) | 1986-07-30 | 1990-03-27 | Alcon Laboratories, Inc. | Sustained release, comfort formulation for glaucoma therapy |
| FR2588189B1 (fr) | 1985-10-03 | 1988-12-02 | Merck Sharp & Dohme | Composition pharmaceutique de type a transition de phase liquide-gel |
| PH23506A (en) | 1986-05-23 | 1989-08-16 | Smithkline Beckman Corp | 1-aralkyl-substituted-1,2,4,-triazole-5-thiols as dopamine- -hydroxylase inhibitors |
| JPH089541B2 (ja) | 1988-03-07 | 1996-01-31 | 三井東圧化学株式会社 | ピラゾール類を主成分とする脳浮腫抑制剤 |
| JP2784925B2 (ja) | 1988-09-07 | 1998-08-13 | 日本農薬株式会社 | ３又は５−フェニルピラゾール類又はその塩及び除草剤 |
| DK0495421T3 (da) | 1991-01-15 | 1996-12-09 | Alcon Lab Inc | Anvendelse af carragenaner i topiske ophthalmiske sammensætninger |
| US5212162A (en) | 1991-03-27 | 1993-05-18 | Alcon Laboratories, Inc. | Use of combinations gelling polysaccharides and finely divided drug carrier substrates in topical ophthalmic compositions |
| JP3810097B2 (ja) | 1993-01-15 | 2006-08-16 | 明治製菓株式会社 | ピロリジン−２−イルカルボニル複素環式化合物誘導体 |
| ATE212985T1 (de) | 1993-11-30 | 2002-02-15 | Searle & Co | Tricyclische,substituierte pyrazolyl- benzolsulfonamide und ihre verwendung als cyclooxygenase ii inhibitoren |
| US5466823A (en) | 1993-11-30 | 1995-11-14 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides |
| US6309853B1 (en) | 1994-08-17 | 2001-10-30 | The Rockfeller University | Modulators of body weight, corresponding nucleic acids and proteins, and diagnostic and therapeutic uses thereof |
| AU700964B2 (en) | 1994-11-10 | 1999-01-14 | Cor Therapeutics, Inc. | Pharmaceutical pyrazole compositions useful as inhibitors of protein kinases |
| US5733955A (en) | 1995-02-10 | 1998-03-31 | The Goodyear Tire & Rubber Company | Asphalt cement modification |
| JP3663522B2 (ja) | 1995-08-12 | 2005-06-22 | 日本農薬株式会社 | 植物生育調節用組成物及びその使用方法 |
| US5756529A (en) | 1995-09-29 | 1998-05-26 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides for use in veterinary therapies |
| WO1997013756A1 (en) | 1995-10-13 | 1997-04-17 | Otsuka Kagaku Kabushiki Kaisha | Pyrazole derivatives and insecticidal compositions containing the same as active ingredient |
| US5792761A (en) | 1996-08-12 | 1998-08-11 | Merck & Co., Inc. | Thrombin inhibitors |
| DE19632773A1 (de) | 1996-08-14 | 1998-02-19 | Basf Ag | Neue Thrombininhibitoren |
| GB9622370D0 (en) | 1996-10-28 | 1997-01-08 | Merck Sharp & Dohme | Therapeutic agents |
| US5869500A (en) | 1996-12-13 | 1999-02-09 | Hoffmann-La Roche Inc. | Pyridone compounds useful in treating Alzheimer's disease |
| NZ336162A (en) | 1996-12-23 | 2000-09-29 | Du Pont Pharm Co | pyrrole, tetrazole or pyrazole derivatives useful as factor Xa inhibitors |
| AR012117A1 (es) | 1997-03-21 | 2000-09-27 | Novartis Ag | Compuestos herbicidas, proceso para su preparacion, compuestos intermediarios para su exclusivo uso en dicho proceso, composicion herbicidae inhibidora del crecimiento de las plantas, metodo para controlar el crecimiento indeseado de plantas y uso de dicha composicion en el control de |
| KR20010071975A (ko) | 1998-08-11 | 2001-07-31 | 해슬러 요세 | 살선충성 피라졸 |
| KR20000047461A (ko) | 1998-12-29 | 2000-07-25 | 성재갑 | 트롬빈 억제제 |
| SE9900070D0 (sv) | 1999-01-13 | 1999-01-13 | Astra Ab | New use |
| AR023510A1 (es) | 1999-04-21 | 2002-09-04 | Astrazeneca Ab | Un equipo de partes, formulacion farmaceutica y uso de un inhibidor de trombina. |
| WO2000071536A1 (en) | 1999-05-20 | 2000-11-30 | E.I. Du Pont De Nemours And Company | Heteroaryloxypyrimidine insecticides and acaricides |
| PL353455A1 (en) | 1999-08-12 | 2003-11-17 | Pharmacia Italia S.P.A. | 3(5)-amino-pyrazole derivatives, process for their preparation and their use as antitumor agents |
| WO2001019798A2 (en) | 1999-09-17 | 2001-03-22 | Cor Therapeutics Inc. | INHIBITORS OF FACTOR Xa |
| US6632815B2 (en) | 1999-09-17 | 2003-10-14 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
| WO2001040223A2 (en) | 1999-12-02 | 2001-06-07 | Novartis Ag | Aminoheterocyclylamides as pesticides and antiparasitic agents |
| WO2002000651A2 (en) | 2000-06-27 | 2002-01-03 | Bristol-Myers Squibb Pharma Company | Factor xa inhibitors |
| WO2002092573A2 (en) | 2001-05-16 | 2002-11-21 | Vertex Pharmaceuticals Incorporated | Heterocyclic substituted pyrazoles as inhibitors of src and other protein kinases |
| US6589997B2 (en) | 2001-06-29 | 2003-07-08 | North Shore-Long Island Jewish Health System | Small-molecule modulators of hepatocyte growth factor/scatter factor activities |
| SI21097A (sl) | 2001-12-04 | 2003-06-30 | Univerza V Ljubljani | Inhibitorji trombina |
| EP1509505A2 (en) | 2002-01-23 | 2005-03-02 | Arena Pharmaceuticals, Inc. | SMALL MOLECULE MODULATORS OF THE 5−HT2A SEROTONIN RECEPTOR USEFUL FOR THE PROPHYLAXIS AND TREATMENT OF DISORDERS RELATED THERETO |
| SE0200198D0 (sv) | 2002-01-23 | 2002-01-23 | Astrazeneca Ab | New use |
| JP2003313103A (ja) | 2002-02-20 | 2003-11-06 | Sankyo Agro Kk | ４−アシルアミノピラゾール誘導体を有効成分として含有する農薬 |
| GB0214139D0 (en) | 2002-06-19 | 2002-07-31 | Glaxo Group Ltd | Chemical compounds |
| DE10229070A1 (de) | 2002-06-28 | 2004-01-15 | Merck Patent Gmbh | Phenylderivate 5 |
| TW200812986A (en) * | 2002-08-09 | 2008-03-16 | Nps Pharma Inc | New compounds |
| WO2004035564A1 (en) | 2002-10-17 | 2004-04-29 | Syngenta Participations Ag | Pyridine derivatives useful as herbicides |
| US7192976B2 (en) | 2002-12-21 | 2007-03-20 | Angion Biomedica Corporation | Small molecule modulators of hepatocyte growth factor (scatter factor) activity |
| JP4585448B2 (ja) | 2002-12-23 | 2010-11-24 | サノフィ−アベンティス・ドイチュラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 第Ｘａ因子阻害剤としてのピラゾール−誘導体 |
| WO2004058722A1 (en) | 2002-12-24 | 2004-07-15 | Arena Pharmaceuticals, Inc. | Diarylamine and arylheteroarylamine pyrazole derivatives as modulators of 5ht2a |
| US20040147561A1 (en) | 2002-12-27 | 2004-07-29 | Wenge Zhong | Pyrid-2-one derivatives and methods of use |
| JP2004231528A (ja) | 2003-01-28 | 2004-08-19 | Sankyo Agro Kk | アミド誘導体 |
| GB0308318D0 (en) | 2003-04-10 | 2003-05-14 | Merck Sharp & Dohme | Therapeutic agents |
| US7396935B2 (en) | 2003-05-01 | 2008-07-08 | Bristol-Myers Squibb Company | Aryl-substituted pyrazole-amide compounds useful as kinase inhibitors |
| CA2524269A1 (en) | 2003-05-02 | 2004-11-18 | Elan Pharmaceuticals, Inc. | 4- bromo - 5 - (2- chloro - benzoylamino) - 1h - pyrazole - 3 - carboxylic acid amide derivatives and related compounds as bradykinin b1 receptor antagonists for the treatment of inflammatory diseases |
| EP1479679A1 (en) | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | Triazole-derivatives as factor Xa inhibitors |
| US7223780B2 (en) | 2003-05-19 | 2007-05-29 | Sanofi-Aventis Deutschland Gmbh | Triazole-derivatives as blood clotting enzyme factor Xa inhibitors |
| EP1697342A2 (en) * | 2003-09-08 | 2006-09-06 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| AU2004270733B2 (en) | 2003-09-11 | 2011-05-19 | Itherx Pharma, Inc. | Cytokine inhibitors |
| US20060281803A1 (en) | 2003-09-23 | 2006-12-14 | Lindsley Craig W | Pyrazole modulators of metabotropic glutamate receptors |
| TW200526588A (en) | 2003-11-17 | 2005-08-16 | Smithkline Beecham Corp | Chemical compounds |
| US20080188527A1 (en) | 2003-12-23 | 2008-08-07 | Cashman John R | Synthetic Compounds and Derivatives as Modulators of Smoking or Nicotine Ingestion and Lung Cancer |
| MXPA06010900A (es) | 2004-03-26 | 2007-02-21 | Methylgene Inc | Inhibidores de histona desacetilasa. |
| US7429604B2 (en) * | 2004-06-15 | 2008-09-30 | Bristol Myers Squibb Company | Six-membered heterocycles useful as serine protease inhibitors |
| US7235530B2 (en) | 2004-09-27 | 2007-06-26 | Dyax Corporation | Kallikrein inhibitors and anti-thrombolytic agents and uses thereof |
| US8084451B2 (en) | 2005-01-10 | 2011-12-27 | University Of Connecticut | Heteropyrrole analogs acting on cannabinoid receptors |
| EP1867331A4 (en) | 2005-04-06 | 2009-04-08 | Takeda Pharmaceutical | TRIAZOLE DERIVATIVE AND USE THEREOF |
| GB0507577D0 (en) | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
| CN100427481C (zh) | 2005-05-26 | 2008-10-22 | 沈阳化工研究院 | 一种芳基醚类化合物及其制备与应用 |
| WO2007067836A2 (en) | 2005-12-05 | 2007-06-14 | Boehringer Ingelheim International Gmbh | Substituted pyrazole compounds useful as soluble epoxide hydrolase inhibitors |
| EP2016068A1 (en) | 2006-05-03 | 2009-01-21 | AstraZeneca AB | Pyrazole derivatives and their use as pi3k inhibitors |
| AU2007257959A1 (en) | 2006-06-09 | 2007-12-21 | Kemia, Inc. | Therapy using cytokine inhibitors |
| DE102006032824A1 (de) | 2006-07-14 | 2008-01-17 | Bayer Healthcare Ag | Substituierte Indazole |
| EP2043631A2 (en) | 2006-07-17 | 2009-04-08 | Boehringer Ingelheim International GmbH | New indications for direct thrombin inhibitors in the cardiovascular field |
| US7625944B2 (en) | 2006-07-31 | 2009-12-01 | Activesite Pharmaceuticals, Inc. | Inhibitors of plasma kallikrein |
| WO2008023235A1 (en) | 2006-08-25 | 2008-02-28 | Pfizer Products Inc. | Pyrazole derivatives as anti-platelet and anti-thrombotic agents |
| WO2008062739A1 (en) | 2006-11-20 | 2008-05-29 | Japan Tobacco Inc. | Pyrazoles and use thereof as drugs |
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| US20100144793A1 (en) | 2006-11-24 | 2010-06-10 | Ac Immune Sa | Novel compounds for the treatment of diseases associated with amyloid or amyloid-like proteins |
| EP2125778A1 (en) | 2006-12-22 | 2009-12-02 | Millennium Pharmaceuticals, Inc. | Certain pyrazoline derivatives with kinase inhibitory activity |
| UY30892A1 (es) | 2007-02-07 | 2008-09-02 | Smithkline Beckman Corp | Inhibidores de la actividad akt |
| WO2008105383A1 (ja) | 2007-02-26 | 2008-09-04 | Toray Industries, Inc. | ピラゾール誘導体およびその医薬用途 |
| GB0714129D0 (en) | 2007-07-19 | 2007-08-29 | Smithkline Beecham Corp | compounds |
| AU2008284746A1 (en) | 2007-08-06 | 2009-02-12 | Dainippon Sumitomo Pharma Co., Ltd. | Aminopyrazole amide derivative |
| KR101559597B1 (ko) | 2007-09-28 | 2015-10-12 | 다케다 야쿠힌 고교 가부시키가이샤 | ５―원 헤테로시클릭 화합물 |
| JP2011507910A (ja) | 2007-12-21 | 2011-03-10 | ユニバーシティー オブ ロチェスター | 真核生物の寿命を変更するための方法 |
| US8658685B2 (en) | 2008-01-31 | 2014-02-25 | Activesite Pharmaceuticals, Inc. | Methods for treatment of kallikrein-related disorders |
| JP2011511806A (ja) | 2008-02-07 | 2011-04-14 | マサチューセッツ・アイ・アンド・イア・インファーマリー | Ａｔｏｈ１発現を増強する化合物 |
| CN102088973A (zh) | 2008-05-15 | 2011-06-08 | 杜克大学 | 与热休克转录因子激活化合物及其靶标有关的组合物和方法 |
| JP5504259B2 (ja) | 2008-05-19 | 2014-05-28 | メルク・シャープ・アンド・ドーム・コーポレーション | 第ｉｘａ因子阻害剤としての複素環式化合物 |
| JP5775452B2 (ja) | 2008-07-10 | 2015-09-09 | アンジオン バイオメディカ コーポレイション | 肝細胞増殖因子（分散因子）活性の低分子モジュレーターの組成物および方法 |
| US8273900B2 (en) | 2008-08-07 | 2012-09-25 | Novartis Ag | Organic compounds |
| CA2733958A1 (en) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Insecticidal 4-phenyl-1h-pyrazoles |
| WO2010020601A1 (en) | 2008-08-19 | 2010-02-25 | Boehringer Ingelheim International Gmbh | Dabigatran in tumour therapy |
| JP2012500243A (ja) | 2008-08-19 | 2012-01-05 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 肺高血圧症患者の治療のためのダビガトランエテキシラートの使用 |
| MX2011001612A (es) | 2008-08-19 | 2011-03-04 | Boehringer Ingelheim Int | Dabigatran para cateterismo cardiaco con intervencion percutanea. |
| AU2010244684B2 (en) | 2009-05-07 | 2014-07-03 | Grunenthal Gmbh | Substituted aromatic carboxamide and urea derivatives as vanilloid receptor ligands |
| SG184243A1 (en) * | 2010-03-30 | 2012-10-30 | Verseon Corp | Multisubstituted aromatic compounds as inhibitors of thrombin |
| CN101851207B (zh) | 2010-06-11 | 2012-01-25 | 扬州康伊尔医药科技有限公司 | 抗病毒化合物中间体1-酰基-吡唑-3-羧酸及其制备方法 |
| RS54761B1 (sr) | 2010-06-24 | 2016-10-31 | Gilead Sciences | Pirazolo[1,5-a]pirimidini i-triazini kao antiviralni agensi |
| EP2604602A4 (en) | 2010-08-11 | 2013-12-18 | Taisho Pharmaceutical Co Ltd | HETEROARYL PYRAZOLE DERIVATIVE |
| EP2635278B1 (en) | 2010-11-03 | 2019-12-11 | Dow AgroSciences LLC | Pesticidal compositions and processes related thereto |
| WO2012065019A2 (en) | 2010-11-12 | 2012-05-18 | Exelixis, Inc. | Pyridopyrimidinone inhibitors of p13k alpha |
| WO2012129258A1 (en) | 2011-03-22 | 2012-09-27 | Merck Sharp & Dohme Corp. | Amidopyrazole inhibitors of interleukin receptor-associated kinases |
| US8691861B2 (en) | 2011-04-13 | 2014-04-08 | Activesite Pharmaceuticals, Inc. | Prodrugs of inhibitors of plasma kallikrein |
| WO2012154880A1 (en) | 2011-05-09 | 2012-11-15 | Proteostasis Therapeutics, Inc. | Proteostasis regulators for treating cystic fibrosis and other protein misfolding diseases |
| HK1199713A1 (en) | 2011-05-17 | 2015-08-14 | 普莱希科公司 | Kinase modulation and indications therefor |
| WO2013039985A2 (en) | 2011-09-12 | 2013-03-21 | The Johns Hopkins University | Serine protease inhibitors |
| WO2013049591A2 (en) | 2011-09-29 | 2013-04-04 | Verseon Corporation | Dual inhibitor compounds and methods of use thereof |
| WO2013101830A1 (en) * | 2011-12-27 | 2013-07-04 | Ironwood Pharmaceuticals, Inc. | 2 - benzyl, 3 - (pyrimidin- 2 -yl) substituted pyrazoles useful as sgc stimulators |
| EP2807157A1 (en) | 2012-01-27 | 2014-12-03 | Novartis AG | 5-membered heteroarylcarboxamide derivatives as plasma kallikrein inhibitors |
| EP2862861B1 (en) | 2012-06-14 | 2016-01-06 | Daiichi Sankyo Company, Limited | Piperidinylpyrazolopyridine derivative |
| EP2945938B1 (en) | 2013-01-18 | 2018-03-07 | F. Hoffmann-La Roche AG | 3-substituted pyrazoles and use as dlk inhibitors |
| SI2968297T1 (sl) * | 2013-03-15 | 2019-02-28 | Verseon Corporation | Multisubstituirane aromatske skupine kot inhibitorji serinske proteaze |
| WO2015087995A1 (ja) | 2013-12-13 | 2015-06-18 | 第一三共株式会社 | シクロアルキル又はヘテロシクリルピラゾロピリジン誘導体 |
| WO2015118342A1 (en) | 2014-02-06 | 2015-08-13 | Heptares Therapeutics Limited | Bicyclic aza compounds as muscarinic m1 receptor agonists. |
| KR20170048410A (ko) * | 2014-09-17 | 2017-05-08 | 베르선 코포레이션 | 세린 프로테아제 저해제로서의 피라졸릴-치환된 피리돈 화합물 |
-
2015
- 2015-09-17 KR KR1020177007352A patent/KR20170048410A/ko not_active Withdrawn
- 2015-09-17 WO PCT/US2015/050809 patent/WO2016044662A1/en not_active Ceased
- 2015-09-17 EP EP15841577.8A patent/EP3194369A4/en not_active Withdrawn
- 2015-09-17 SG SG11201701940UA patent/SG11201701940UA/en unknown
- 2015-09-17 CA CA2960790A patent/CA2960790A1/en not_active Abandoned
- 2015-09-17 AU AU2015317522A patent/AU2015317522A1/en not_active Abandoned
- 2015-09-17 CN CN201580050088.0A patent/CN106687445A/zh active Pending
- 2015-09-17 JP JP2017514899A patent/JP2017528486A/ja active Pending
- 2015-09-17 US US15/512,037 patent/US10189810B2/en active Active
- 2015-09-17 BR BR112017004704A patent/BR112017004704A2/pt not_active Application Discontinuation
- 2015-09-17 RU RU2017112739A patent/RU2017112739A/ru not_active Application Discontinuation
- 2015-09-17 MX MX2017003624A patent/MX2017003624A/es unknown
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2017
- 2017-03-06 IL IL250965A patent/IL250965A0/en unknown
- 2017-03-13 ZA ZA2017/01799A patent/ZA201701799B/en unknown
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2018
- 2018-12-07 US US16/213,272 patent/US20190359586A1/en not_active Abandoned
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2020
- 2020-03-26 AU AU2020202167A patent/AU2020202167A1/en not_active Abandoned
- 2020-05-19 JP JP2020087253A patent/JP2020143112A/ja active Pending
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| SG11201701940UA (en) | 2017-04-27 |
| EP3194369A4 (en) | 2018-02-28 |
| BR112017004704A2 (pt) | 2018-01-23 |
| MX2017003624A (es) | 2017-07-13 |
| IL250965A0 (en) | 2017-04-30 |
| ZA201701799B (en) | 2019-06-26 |
| RU2017112739A3 (enExample) | 2019-04-01 |
| AU2020202167A1 (en) | 2020-04-30 |
| JP2017528486A (ja) | 2017-09-28 |
| CN106687445A (zh) | 2017-05-17 |
| JP2020143112A (ja) | 2020-09-10 |
| EP3194369A1 (en) | 2017-07-26 |
| WO2016044662A1 (en) | 2016-03-24 |
| KR20170048410A (ko) | 2017-05-08 |
| US20170267656A1 (en) | 2017-09-21 |
| US20190359586A1 (en) | 2019-11-28 |
| US10189810B2 (en) | 2019-01-29 |
| AU2015317522A1 (en) | 2017-03-23 |
| CA2960790A1 (en) | 2016-03-24 |
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