N-(5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide | 1206101-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡啶类
• 英文名称: N-(5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide
• 英文别名: N-(5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-acetamide
• CAS: 1206101-26-9
• 化学式: C₈H₇BrN₄O
• 分子量: 255.074
• InChiKey: UAWUFBVTEQUTJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide 、 4-苄氧基苯硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 生成 N-(5-(4-(benzyloxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide
  参考文献：
  名称：

  NOVEL COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE AND INFLAMMATORY DISEASES

  摘要：

  揭示了一种具有以下公式表示的[1,2,4]三唑并[1,5-a]吡啶化合物：此化合物可制备为药物组合物，并可用于哺乳动物，包括人类的预防和治疗，例如涉及软骨降解，骨骼和/或关节退化的疾病，例如骨关节炎；以及涉及炎症或免疫反应的情况，例如克罗恩病，类风湿性关节炎，牛皮癣，过敏性气道疾病（例如哮喘，鼻炎），青少年特发性关节炎，结肠炎，炎性肠病，内毒素驱动的疾病状态（例如旁路手术后的并发症或长期内毒素状态导致的慢性心力衰竭等），涉及软骨周转受损的疾病（例如涉及软骨细胞的合成刺激的疾病），先天性软骨畸形，与IL6过度分泌和移植排斥（例如器官移植排斥）和增殖性疾病有关的疾病。

  公开号：

  US20100029709A1
• 作为产物：
  描述：

  2-氨基-6-溴吡啶 在 盐酸羟胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 19.0h， 生成 N-(5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide
  参考文献：
  名称：

  Triazolopyridines as Selective JAK1 Inhibitors: From Hit Identification to GLPG0634

  摘要：

  Janus kinases (JAK1, JAK2, JAK3, and TYK2) are involved in the signaling of multiple cytokines important in cellular function. Blockade of the JAK-STAT pathway with a small molecule has been shown to provide therapeutic immunomodulation. Having identified JAK1 as a possible new target for arthritis at Galapagos, the compound library was screened against JAK1, resulting in the identification of a triazolopyridine-based series of inhibitors represented by 3. Optimization within this chemical series led to identification of GLPG0634 (65, filgotinib), a selective JAK1 inhibitor currently in phase 2B development for RA and phase 2A development for Crohns disease (CD).

  DOI：

  10.1021/jm501262q

文献信息

• [EN] NOVEL COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE AND INFLAMMATORY DISEASES<br/>[FR] NOUVEAUX COMPOSÉS UTILES POUR LE TRAITEMENT DE MALADIES DÉGÉNÉRATIVES ET INFLAMMATOIRES
  申请人：GALAPAGOS NV

  公开号：WO2010010186A1

  公开（公告）日：2010-01-28

  [1,2,4]Triazolo[1,5-a]pyridine compounds are disclosed that have a formula represented by the following: (I) These compound may be prepared as a pharmaceutical composition, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, diseases involving cartilage degradation, bone and/or joint degradation, for example osteoarthritis; and/or conditions involving inflammation or immune responses, such as Crohn's disease, rheumatoid arthritis, psoriasis, allergic airways disease (e.g. asthma, rhinitis), juvenile idiopathic arthritis, colitis, inflammatory bowel diseases, endotoxin-driven disease states (e.g. complications after bypass surgery or chronic endotoxin states contributing to e.g. chronic cardiac failure), diseases involving impairment of cartilage turnover (e.g. diseases involving the anabolic stimulation of chondrocytes), congenital cartilage malformations, diseases associated with hypersecretion of IL6 and transplantation rejection (e.g. organ transplant rejection) and proliferative diseases.

  [1,2,4]三唑并[1,5-a]吡啶化合物被披露，其具有以下公式(I)表示的化合物。这些化合物可以制备成药物组合物，并且可以用于预防和治疗包括人类在内的哺乳动物的多种病症，包括但不限于涉及软骨降解、骨骼和/或关节退化的疾病，例如骨关节炎；以及/或涉及炎症或免疫反应的状况，如克罗恩病、类风湿性关节炎、银屑病、过敏性呼吸道疾病（例如哮喘、鼻炎）、幼年特发性关节炎、结肠炎、炎症性肠病、内毒素驱动的疾病状态（例如搭桥手术后的并发症或慢性内毒素状态导致慢性心力衰竭）、涉及软骨转换受损的疾病（例如涉及软骨细胞合成代谢刺激的疾病）、先天性软骨畸形、与IL6过度分泌和移植排斥反应相关的疾病（例如器官移植排斥）以及增殖性疾病。
• TRIAZOLOPYRIDINE KINASE INHIBITORS USEFUL FOR THE TREATMENT OF DEGENERATIVE AND INFLAMMATORY DISEASES
  申请人：MENET Christel Jeanne Marie

  公开号：US20120309784A1

  公开（公告）日：2012-12-06

  A novel [1,2,4]triazolo[1,5-a]pyridine compound is disclosed that has a formula represented by the following: This compound may be prepared as a pharmaceutical composition, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, diseases involving cartilage degradation, bone and/or joint degradation, for example osteoarthritis; and/or conditions involving inflammation or immune responses, such as Crohn's disease, rheumatoid arthritis, psoriasis, allergic airways disease (e.g. asthma, rhinitis), juvenile idiopathic arthritis, colitis, inflammatory bowel diseases, endotoxin-driven disease states (e.g. complications after bypass surgery or chronic endotoxin states contributing to e.g. chronic cardiac failure), diseases involving impairment of cartilage turnover (e.g. diseases involving the anabolic stimulation of chondrocytes), congenital cartilage malformations, diseases associated with hypersecretion of IL6 and transplantation rejection (e.g. organ transplant rejection) and proliferative diseases.

  本发明揭示了一种具有以下公式表示的新型[1,2,4]三唑并[1,5-a]吡啶化合物： 此化合物可以制备为一种药物组成物，并可用于哺乳动物包括人类的预防和治疗多种疾病，包括但不限于涉及软骨降解、骨骼和/或关节降解的疾病，例如骨关节炎；以及涉及炎症或免疫反应的疾病，例如克罗恩病、类风湿性关节炎、银屑病、过敏性呼吸道疾病（例如哮喘、鼻炎）、儿童特发性关节炎、结肠炎、炎症性肠病、内毒素驱动的疾病状态（例如旁路手术后的并发症或慢性内毒素状态导致的慢性心力衰竭等），涉及软骨周转受损的疾病（例如涉及软骨细胞的合成刺激的疾病）、先天性软骨畸形、与IL6过度分泌和移植排斥（例如器官移植排斥）及增生性疾病有关的疾病。
• Compounds useful for the treatment of degenerative and inflammatory diseases
  申请人：Menet Christel Jeanne Marie

  公开号：US09415037B2

  公开（公告）日：2016-08-16

  [1,2,4]triazolo[1,5-a]pyridine compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, diseases involving cartilage degradation, bone and/or joint degradation, for example osteoarthritis; and/or conditions involving inflammation or immune responses, such as Crohn's disease, rheumatoid arthritis, psoriasis, allergic airways disease (e.g. asthma, rhinitis), juvenile idiopathic arthritis, colitis, inflammatory bowel diseases, endotoxin-driven disease states (e.g. complications after bypass surgery or chronic endotoxin states contributing to e.g. chronic cardiac failure), diseases involving impairment of cartilage turnover (e.g. diseases involving the anabolic stimulation of chondrocytes), congenital cartilage malformations, diseases associated with hypersecretion of IL6 and transplantation rejection (e.g. organ transplant rejection) and proliferative diseases.

  本发明揭示了一种具有以下式子表示的[1,2,4]三唑并[1,5-a]吡啶化合物： 这些化合物可以制备成药物组合物，并可用于预防和治疗哺乳动物（包括人类）的各种疾病，包括但不限于涉及软骨降解、骨骼和/或关节降解的疾病，例如骨关节炎；以及涉及炎症或免疫反应的疾病，例如克罗恩病、类风湿性关节炎、牛皮癣、过敏性呼吸道疾病（例如哮喘、鼻炎）、少年特发性关节炎、结肠炎、炎症性肠病、内毒素驱动的疾病状态（例如旁路手术后的并发症或慢性内毒素状态导致的慢性心力衰竭等），涉及软骨周转障碍的疾病（例如涉及软骨细胞的合成刺激的疾病）、先天性软骨畸形、与IL6高分泌相关的疾病和移植排斥反应（例如器官移植排斥反应）和增殖性疾病。
• NOVEL COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE AND INFLAMMATORY DISEASES.
  申请人：Galapagos N.V.

  公开号：EP2346864A1

  公开（公告）日：2011-07-27
• US8242274B2
  申请人：——

  公开号：US8242274B2

  公开（公告）日：2012-08-14