5-Ethynyl-1-methyl-1h-imidazole-2-carboxamide | 957147-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Ethynyl-1-methyl-1h-imidazole-2-carboxamide
• 英文别名: 5-ethynyl-1-methylimidazole-2-carboxamide
• CAS: 957147-20-5
• 化学式: C₇H₇N₃O
• 分子量: 149.152
• InChiKey: IUYKBAFHGCMKGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Ethynyl-1-methyl-1h-imidazole-2-carboxamide 、 N-(3-(1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-iodo-4-methylbenzamide 生成 5-[5-(3-imidazol-1-yl-5-trifluoromethylphenylcarbamoyl)-2-methyl-phenylethynyl]-1-methyl-1H-imidazole-2-carboxylic acid amide
  参考文献：
  名称：

  Monocyclic Heterocyclic Compounds

  摘要：

  本发明涉及具有以下一般式的化合物：其中变量基团的定义如本文所述，以及它们的制备和使用。

  公开号：

  US20090149471A1
• 作为产物：
  描述：

  在 甲醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 5-Ethynyl-1-methyl-1h-imidazole-2-carboxamide
  参考文献：
  名称：

  Discovery of 5-(arenethynyl) hetero-monocyclic derivatives as potent inhibitors of BCR–ABL including the T315I gatekeeper mutant

  摘要：

  Ponatinib (AP24534) was previously identified as a pan-BCR-ABL inhibitor that potently inhibits the T315I gatekeeper mutant, and has advanced into clinical development for the treatment of refractory or resistant CML. In this study, we explored a novel series of five and six membered monocycles as alternate hinge-binding templates to replace the 6,5-fused imidazopyridazine core of ponatinib. Like ponatinib, these monocycles are tethered to pendant toluanilides via an ethynyl linker. Several compounds in this series displayed excellent in vitro potency against both native BCR-ABL and the T315I mutant. Notably, a subset of inhibitors exhibited desirable PK and were orally active in a mouse model of T315I-driven CML. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.060

文献信息

• Monocyclic Heteroaryl compounds
  申请人：ARIAD Pharmaceuticals, Inc.

  公开号：US08278307B2

  公开（公告）日：2012-10-02

  This invention relates to compounds of the general formula: in which the variable groups are as defined herein, and to their preparation and use.

  本发明涉及以下通式的化合物：其中变量基团如本文所定义，并涉及其制备和应用。
• Monocyclic Heterocyclic Compounds
  申请人：Shakespeare William C.

  公开号：US20090149471A1

  公开（公告）日：2009-06-11

  This invention relates to compounds of the general formula: in which the variable groups are as defined herein, and to their preparation and use.

  本发明涉及具有以下一般式的化合物：其中变量基团的定义如本文所述，以及它们的制备和使用。
• MONOCYCLIC HETEROARYL COMPOUNDS
  申请人：ARIAD PHARMACEUTICALS, INC.

  公开号：EP2024366A2

  公开（公告）日：2009-02-18
• US8278307B2
  申请人：——

  公开号：US8278307B2

  公开（公告）日：2012-10-02
• [EN] MONOCYCLIC HETEROARYL COMPOUNDS<br/>[FR] COMPOSÉS D'HÉTÉROARYLE MONOCYCLIQUE
  申请人：ARIAD PHARMA INC

  公开号：WO2007133562A2

  公开（公告）日：2007-11-22

  [EN] This invention relates to compounds of the general formula(I) in which the variable groups are as defined herein, and to their preparation and use.
  [FR] L'invention concerne des composés de formule (I), dans laquelle des groupes variables sont spécifiés dans la description, ainsi que leur préparation et leur utilisation.