3-(4-fluoro-benzyl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one | 67482-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 3-(4-fluoro-benzyl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one
• 英文别名: 3-[(4-fluorophenyl)methyl]-1H-imidazo[4,5-b]pyridin-2-one
• CAS: 67482-38-6
• 化学式: C₁₃H₁₀FN₃O
• 分子量: 243.24
• InChiKey: KRBYHHCYUOTAKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-fluoro-benzyl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one 在 二(三甲基铝)-1,4-二氮杂二环[2.2.2]辛烷加合物 、 sodium hydride 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 22.0h， 生成 2-[3-(4-fluoro-benzyl)-3H-imidazo[4,5-b]pyridin-2-yloxy]-N-[(S)-1-(4-fluoro-phenyl)-ethyl]-acetamide
  参考文献：
  名称：

  [EN] AUTOTAXIN INHIBITORY COMPOUNDS
  [FR] COMPOSÉS INHIBITEURS DE L'AUTOTAXINE

  摘要：

  本发明涉及式I的化合物，其中A1、A2、A3、R1、R2、R3、R4、R5、R6、L、Ar和Q分别如本文所定义。本发明的化合物是自体脂肪酶（ATX）酶活性的抑制剂。本发明还涉及制备这些化合物的方法，包括含有它们的药物组合物，以及它们在治疗增殖性疾病（如癌症）以及其他ATX活性所涉及的疾病或症状（例如纤维化）中的用途。

  公开号：

  WO2016124939A1
• 作为产物：
  描述：

  N-<(4-fluorophenyl)methyl>-3-nitro-2-pyridinamine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 25.5h， 生成 3-(4-fluoro-benzyl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one
  参考文献：
  名称：

  [EN] AUTOTAXIN INHIBITORY COMPOUNDS
  [FR] COMPOSÉS INHIBITEURS DE L'AUTOTAXINE

  摘要：

  本发明涉及式I的化合物，其中A1、A2、A3、R1、R2、R3、R4、R5、R6、L、Ar和Q分别如本文所定义。本发明的化合物是自体脂肪酶（ATX）酶活性的抑制剂。本发明还涉及制备这些化合物的方法，包括含有它们的药物组合物，以及它们在治疗增殖性疾病（如癌症）以及其他ATX活性所涉及的疾病或症状（例如纤维化）中的用途。

  公开号：

  WO2016124939A1

文献信息

• Autotaxin inhibitory compounds
  申请人：CANCER RESEARCH TECHNOLOGY LIMITED

  公开号：US10654846B2

  公开（公告）日：2020-05-19

  The present invention relates to compounds of formula I, wherein A1, A2, A3, R1, R2, R3, R4, R5, R6, L, Ar and Q are each as defined herein. The compounds of the present invention are inhibitors of autotaxin (ATX) enzyme activity. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions (e.g. fibrosis) in which ATX activity is implicated.

  本发明涉及式 I 的化合物，其中 A1、A2、A3、R1、R2、R3、R4、R5、R6、L、Ar 和 Q 各如本文所定义。本发明的化合物是自体免疫球蛋白（ATX）酶活性的抑制剂。本发明还涉及制备这些化合物的工艺、包含这些化合物的药物组合物，以及它们在治疗增殖性疾病（如癌症）和其他涉及 ATX 活性的疾病或病症（如纤维化）中的用途。
• AUTOTAXIN INHIBITORY COMPOUNDS
  申请人：CANCER RESEARCH TECHNOLOGY LIMITED

  公开号：US20180016274A1

  公开（公告）日：2018-01-18

  The present invention relates to compounds of formula I, wherein A 1 , A 2 , A 3 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L, Ar and Q are each as defined herein. The compounds of the present invention are inhibitors of autotaxin (ATX) enzyme activity. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions (e.g. fibrosis) in which ATX activity is implicated.
• Autotaxin Inhibitory Compunds
  申请人：Cancer Research Technology Limited

  公开号：US20200283435A1

  公开（公告）日：2020-09-10

  The present invention relates to compounds of formula I wherein A 1 , A 2 , A 3 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L, Ar and Q are each as defined herein. The compounds of the present invention are inhibitors of autotaxin (ATX) enzyme activity. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions (e.g. fibrosis) in which ATX activity is implicated.
• [EN] AUTOTAXIN INHIBITORY COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS DE L'AUTOTAXINE
  申请人：CANCER REC TECH LTD

  公开号：WO2016124939A1

  公开（公告）日：2016-08-11

  The present invention relates to compounds of formula I, wherein A1, A2, A3, R1, R2, R3, R4, R5, R6, L, Ar and Q are each as defined herein. The compounds of the present invention are inhibitors of autotaxin (ATX) enzyme activity. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions (e.g. fibrosis) in which ATX activity is implicated.

  本发明涉及式I的化合物，其中A1、A2、A3、R1、R2、R3、R4、R5、R6、L、Ar和Q分别如本文所定义。本发明的化合物是自体脂肪酶（ATX）酶活性的抑制剂。本发明还涉及制备这些化合物的方法，包括含有它们的药物组合物，以及它们在治疗增殖性疾病（如癌症）以及其他ATX活性所涉及的疾病或症状（例如纤维化）中的用途。
• Design, synthesis and characterization of novel N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors leading to the identification of the selective compound, AC1903
  作者：Swagat H. Sharma、Juan Lorenzo Pablo、Monica Suarez Montesinos、Anna Greka、Corey R. Hopkins

  DOI：10.1016/j.bmcl.2018.12.007

  日期：2019.1

  The transient receptor potential cation channel 5 (TRPC5) has been previously shown to affect podocyte survival in the kidney. As such, inhibitors of TRPC5 are interesting candidates for the treatment of chronic kidney disease (CKD). Herein, we report the synthesis and biological characterization of a series of N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors. Work reported here evaluates the benzimidazole scaffold and substituents resulting in the discovery of AC1903, a TRPC5 inhibitor that is active in multiple animal models of CKD.