CA2895209C - Substituted pyridine and pyrazine compounds as pde4 inhibitors - Google Patents

Substituted pyridine and pyrazine compounds as pde4 inhibitors Download PDF

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Publication number
CA2895209C
CA2895209C CA2895209A CA2895209A CA2895209C CA 2895209 C CA2895209 C CA 2895209C CA 2895209 A CA2895209 A CA 2895209A CA 2895209 A CA2895209 A CA 2895209A CA 2895209 C CA2895209 C CA 2895209C
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disorder
compound
methyl
methoxypyridin
difluoromethoxy
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French (fr)
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CA2895209A1 (en
Inventor
Venkataiah Bollu
James Breitenbucher
Alan Kaplan
Robert Lemus
Andrew Lindstrom
Troy Vickers
Mark E. Wilson
James Zapf
Michael I. Weinhouse
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Dart Neuroscience Cayman Ltd
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Dart Neuroscience Cayman Ltd
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Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6282721B2 (ja) 2013-03-14 2018-02-21 ダート・ニューロサイエンス・(ケイマン)・リミテッド Pde4阻害剤としての置換ピリジン及びピラジン化合物
EP3519816A4 (en) * 2016-09-29 2020-05-06 The Regents of the University of California Compounds for increasing neural plasticity
EP3773562A1 (en) * 2018-04-05 2021-02-17 Universiteit Hasselt Selective pde4d inhibitors against demyelinating diseases
CN109438434B (zh) * 2018-11-19 2021-05-04 华南农业大学 一种含噁唑环的2-氰基亚氨基噻唑烷类化合物及其制备方法和应用
CN113784962B (zh) 2019-02-27 2025-04-25 加利福尼亚大学董事会 用于治疗脑部疾病的氮杂环庚三烯并-吲哚类和其他杂环
AU2020228289A1 (en) 2019-02-27 2021-09-09 The Regents Of The University Of California N-substituted indoles and other heterocycles for treating brain disorders
JP2022531129A (ja) * 2019-04-23 2022-07-06 テトラ ディスカバリー パートナーズ インコーポレイテッド Pde4d阻害剤としての3-ヒドロキシ-2-フェニル-6-(ピラゾール-4-イルメチル)ピリジン誘導体
EP3965760A4 (en) * 2019-05-06 2023-01-04 Calcimedica, Inc. SYNTHESIS OF CRAC CHANNEL INHIBITORS
AU2020381103B2 (en) * 2019-11-07 2022-08-11 Cybin Uk Ltd Compounds
US12404265B2 (en) 2020-08-04 2025-09-02 Nura Bio, Inc. Substituted pyridine derivatives as SARM1 inhibitors
CN111995585B (zh) * 2020-08-04 2022-01-25 常州大学 嘧啶乙酰胺类化合物及其作为磷酸二酯酶pde2活性抑制剂的应用
CN116438171A (zh) 2020-09-16 2023-07-14 努拉生物公司 作为sarm1抑制剂的取代的吡啶衍生物
JP2024528036A (ja) 2021-07-28 2024-07-26 ヌラ バイオ,インク. Sarm1阻害剤としての置換ピリジン誘導体
TW202333668A (zh) 2021-12-15 2023-09-01 美商德利克斯醫療公司 經苯氧基及苄氧基取代之精神成形素(psychoplastogen)及其用途
CN116265440B (zh) * 2021-12-16 2024-09-27 贵州大学 一种水杨酮拼接吡啶酮类化合物及其制备方法及应用
EP4562001A1 (en) * 2022-07-27 2025-06-04 Nura Bio, Inc. Substituted pyridine derivatives as sarm1 inhibitors
WO2024067660A1 (zh) 2022-09-29 2024-04-04 苏州爱科百发生物医药技术有限公司 氮杂稠环类化合物、其制备方法及其在医药上的应用
CN116082254B (zh) * 2022-12-28 2025-04-11 浙江永太科技股份有限公司 一种1-烷基-1,2,4-三氮唑-3-甲醇的制备方法

Family Cites Families (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4938949A (en) 1988-09-12 1990-07-03 University Of New York Treatment of damaged bone marrow and dosage units therefor
AU1504599A (en) 1997-12-17 1999-07-05 Shionogi & Co., Ltd. Novel pyridine compounds
US9931318B2 (en) 2003-04-08 2018-04-03 Dart Neuroscience (Cayman) Ltd. Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation
ES2373540T3 (es) 2000-08-10 2012-02-06 Cold Spring Harbor Laboratory Entrenamiento cognitivo aumentado.
US7868015B2 (en) 2000-08-10 2011-01-11 Cold Spring Harbor Laboratory Phosphodiesesterase 4 inhibitors for the treatment of a cognitive deficit
GB0111078D0 (en) 2001-05-04 2001-06-27 Novartis Ag Organic compounds
MY130622A (en) 2001-11-05 2007-07-31 Novartis Ag Naphthyridine derivatives, their preparation and their use as phosphodiesterase isoenzyme 4 (pde4) inhibitors
AR037714A1 (es) 2001-12-06 2004-12-01 Maxia Pharmaceuticals Inc Derivados de tiazolidinona y oxazolidinona 2-sustituidos para la inhibicion de fosfatasas y el tratamiento de cancer
CN100513397C (zh) 2002-11-19 2009-07-15 记忆药物公司 磷酸二酯酶4抑制剂
GB0229281D0 (en) 2002-12-16 2003-01-22 Novartis Ag Organic compounds
US20050020587A1 (en) 2003-07-25 2005-01-27 Pfizer Inc Nicotinamide derivatives useful as PDE4 inhibitors
MY141255A (en) * 2003-12-11 2010-03-31 Memory Pharm Corp Phosphodiesterase 4 inhibitors, including n-substituted diarylamine analogs
KR101267392B1 (ko) * 2004-06-30 2013-05-23 주식회사 씨앤드씨신약연구소 피리딘 유도체 및 그의 제조방법
GB0425572D0 (en) 2004-11-19 2004-12-22 Glaxo Group Ltd 1,7-Naphthyridines
CN101163706A (zh) 2005-04-21 2008-04-16 贝林格尔·英格海姆国际有限公司 用于治疗炎性疾病的二氢噻吩并嘧啶
WO2006124874A2 (en) * 2005-05-12 2006-11-23 Kalypsys, Inc. Inhibitors of b-raf kinase
AU2007221020B9 (en) 2006-02-28 2013-04-04 Dart Neuroscience (Cayman) Ltd. Therapeutic compounds
US7829713B2 (en) 2006-02-28 2010-11-09 Helicon Therapeutics, Inc. Therapeutic piperazines
US20070254913A1 (en) * 2006-04-19 2007-11-01 Dunn Robert F Phosphodiesterase 4 inhibitors
EP2032585B1 (de) 2006-05-24 2014-07-23 Boehringer Ingelheim International GmbH Substituierte pteridine als therapeutika
MX2009003222A (es) * 2006-10-04 2009-04-06 Hoffmann La Roche Derivados de 3-piridinocarboxamida y 2-pirazinocarboxamida como agentes elevadores de colesterol de lipoproteina de alta densidad.
CN102014928A (zh) 2007-05-15 2011-04-13 海利空医疗公司 使用小干扰RNA(siRNA)鉴别参与记忆形成的基因的方法
EP2182809B1 (en) 2007-08-27 2018-01-17 Dart Neuroscience (Cayman) Ltd Therapeutic isoxazole compounds
US8877816B2 (en) 2007-11-21 2014-11-04 Decode Genetics Ehf 4-(or 5-) substituted catechol derivatives
WO2009067604A1 (en) 2007-11-21 2009-05-28 Decode Genetics Ehf Substituted benzoazole pde4 inhibitors for treating inflammatory, cardiovascular and cns disorders
EP2222638A2 (en) * 2007-11-21 2010-09-01 Decode Genetics EHF Biaryl pde4 inhibitors for treating inflammation
EP2222639A1 (en) 2007-11-21 2010-09-01 Decode Genetics EHF Biaryl pde4 inhibitors for treating pulmonary and cardiovascular disorders
WO2010003084A2 (en) 2008-07-02 2010-01-07 Memory Pharmaceuticals Corporation Phosphodiesterase 4 inhibitors
US20100125087A1 (en) 2008-11-14 2010-05-20 Astrazeneca Ab New compounds 575
WO2010059836A1 (en) 2008-11-20 2010-05-27 Decode Genetics Ehf Substituted aza-bridged bicyclics for cardiovascular and cns disease
EP2630136A1 (en) * 2010-10-21 2013-08-28 Universität des Saarlandes Selective cyp11b1 inhibitors for the treatment of cortisol dependent diseases
JP6282721B2 (ja) 2013-03-14 2018-02-21 ダート・ニューロサイエンス・(ケイマン)・リミテッド Pde4阻害剤としての置換ピリジン及びピラジン化合物

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