ethyl 3-(aminopyridin-3-yl)-2-(1H-imidazol-4-yl)propanoate | 497160-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-(aminopyridin-3-yl)-2-(1H-imidazol-4-yl)propanoate
• 英文别名: 3-(6-amino-pyridin-3-yl)-2-(1H-imidazol-4-yl)-propionic acid ethyl ester；ethyl 3-(6-aminopyridin-3-yl)-2-(1H-imidazol-4-yl)propionate；ethyl 3-(6-aminopyridin-3-yl)-2-(1H-imidazol-5-yl)propanoate
• CAS: 497160-26-6；497160-27-7；497160-29-9
• 化学式: C₁₃H₁₆N₄O₂
• 分子量: 260.296
• InChiKey: OHPQIRNKENDLOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(aminopyridin-3-yl)-2-(1H-imidazol-4-yl)propanoate 在 盐酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(6-aminopyridin-3-yl)-2-(1-(2-propyl)-1H-imidazol-4-yl)propanoic acid dihydrochloride
  参考文献：
  名称：

  Synthesis and Evaluation of Imidazole Acetic Acid Inhibitors of Activated Thrombin-Activatable Fibrinolysis Inhibitor as Novel Antithrombotics

  摘要：

  Thrombin-activatable fibrinolysis inhibitor (TAFI) is an important regulator of fibrinolysis, and inhibitors of this enzyme have potential use in antithrombotic and thrombolytic therapy. Appropriately substituted imidazole acetic acids such as 10j were found to be potent inhibitors of activated TAFI and selective versus the related carboxypeptidases CPA, CPN, and CPM but not CPB. Further, 10j accelerated clot lysis in vitro and was shown to be efficacious in a primate model of thrombosis.

  DOI：

  10.1021/jm034141y
• 作为产物：
  描述：

  2-(1H-咪唑-4-基)乙酸甲酯盐酸盐 在 盐酸 、 sodium hydride 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.75h， 生成 ethyl 3-(aminopyridin-3-yl)-2-(1H-imidazol-4-yl)propanoate
  参考文献：
  名称：

  Synthesis and Evaluation of Imidazole Acetic Acid Inhibitors of Activated Thrombin-Activatable Fibrinolysis Inhibitor as Novel Antithrombotics

  摘要：

  Thrombin-activatable fibrinolysis inhibitor (TAFI) is an important regulator of fibrinolysis, and inhibitors of this enzyme have potential use in antithrombotic and thrombolytic therapy. Appropriately substituted imidazole acetic acids such as 10j were found to be potent inhibitors of activated TAFI and selective versus the related carboxypeptidases CPA, CPN, and CPM but not CPB. Further, 10j accelerated clot lysis in vitro and was shown to be efficacious in a primate model of thrombosis.

  DOI：

  10.1021/jm034141y
• 作为试剂：
  描述：

  3-(6-amino-pyridin-3-yl)-2-(cyclohex-2-en-1-yl-1H-imidazol-4-yl)-propionic acid ethyl ester 在 palladium 10% on activated carbon ethyl 3-(aminopyridin-3-yl)-2-(1H-imidazol-4-yl)propanoate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3-(6-amino-pyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)-propionic acid ethyl ester
  参考文献：
  名称：

  [DE] IMIDAZOL-DERIVATE ALS TAFIA-INHIBITOREN
  [EN] IMIDAZOLE DERIVATIVES USED AS TAFIA INHIBITORS
  [FR] DERIVES D'IMIDAZOLE SERVANT D'INHIBITEURS DE TAFIA

  摘要：

  这项发明涉及公式（I）的连接物，其为激活的凝血酶激活纤溶抑制剂。公式I的连接物适用于制备用于预防和治疗与血栓形成、栓塞、高凝状态或纤维化变化相关的疾病的药物。

  公开号：

  WO2005105781A1

文献信息

• IMIDAZOLE DERIVATIVES USED AS TAFIA INHIBITORS
  申请人：Kallus Christopher

  公开号：US20070129341A1

  公开（公告）日：2007-06-07

  The present invention relates to compounds of formula (I) which are inhibitors of the activated thrombin-activatable fibrinolysis inhibitor. The compounds of formula (I) are suited for producing medicaments for the prevention and treatment of diseases accompanied by thromboses, embolisms, hypercoagulability or fibrotic changes.

  本发明涉及式(I)的化合物，这些化合物是活化凝血酶可激活纤溶抑制剂的抑制剂。式(I)的化合物适用于生产用于预防和治疗伴随有血栓形成、栓塞、高凝状态或纤维化变化的疾病的药物。
• Process for the preparation of 3-(6-amino-pyridin-3yl)-2-acrylic acid derivatives
  申请人：SANOFI

  公开号：US20130245274A1

  公开（公告）日：2013-09-19

  The present invention relates to a process for the preparation of a compound of the formula I, which comprises reacting a compound of the formula IV with the compound of formula VII R15-A2-CHO and to novel intermediate compounds used therein.

  本发明涉及一种制备式I化合物的过程，包括将式IV化合物与式VII R15-A2-CHO化合物反应，并涉及其中使用的新型中间体化合物。
• [EN] ANTICOAGULANT COMPOUNDS<br/>[FR] COMPOSES ANTICOAGULANTS
  申请人：MERCK & CO INC

  公开号：WO2003013526A1

  公开（公告）日：2003-02-20

  Compounds of the invention are useful in inhibiting carboxypeptidase U and associated thrombotic occlusions having the structure (I) and pharmaceutically acceptable salts thereof, wherein t is N or N(R2'), u is C(R3) or N(R2'), and v is C(R2), N or N(R2), provided that, 1) when t is N and u is C(R3), then v is N(R2); 2) when t is N and u is N(R2'), then v is C(R2), and 3) when t is N(R2') and u is C(R3), then v is N or N(R2).

  本发明的化合物在抑制羧肽酶U和相关的血栓闭塞性疾病中具有用途，其结构式为(I)及其药学上可接受的盐，其中t为N或N(R2')，u为C(R3)或N(R2')，v为C(R2)、N或N(R2)，但需满足以下条件：1）当t为N且u为C(R3)时，则v为N(R2)；2）当t为N且u为N(R2')时，则v为C(R2)；3）当t为N(R2')且u为C(R3)时，则v为N或N(R2)。
• PROCESS FOR THE PREPARATION OF A COMPOUND USEFUL AS AN INHIBITOR OF TAFIA
  申请人：Rossen Kai

  公开号：US20120245358A1

  公开（公告）日：2012-09-27

  The present invention relates to a process for the preparation of a compound of the formula I, which comprises reacting a compound of the formula IV with an oxalic acid diester and to novel intermediate compounds used therein.

  本发明涉及一种制备式I化合物的方法，包括将式IV化合物与草酸二酯反应，并涉及其中使用的新型中间体化合物。
• Imidazole derivatives used as TAFIa inhibitors
  申请人：Kallus Christopher

  公开号：US08710232B2

  公开（公告）日：2014-04-29

  The present invention relates to compounds of formula (I) which are inhibitors of the activated thrombin-activatable fibrinolysis inhibitor. The compounds of formula (I) are suited for producing medicaments for the prevention and treatment of diseases accompanied by thromboses, embolisms, hypercoagulability or fibrotic changes.

  本发明涉及公式（I）的化合物，这些化合物是激活的凝血酶原激活纤溶抑制剂的抑制剂。公式（I）的化合物适用于生产用于预防和治疗伴有血栓形成，栓塞，高凝状态或纤维化变化的疾病的药物。