2-(2,4-dichlorophenyl)-1H-pyrrole-3-carbonitrile | 122453-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(2,4-dichlorophenyl)-1H-pyrrole-3-carbonitrile
• 英文别名: 2-(2,4-Dichloro-phenyl)-1h-pyrrole-3-carbonitrile
• CAS: 122453-07-0
• 化学式: C₁₁H₆Cl₂N₂
• 分子量: 237.088
• InChiKey: PHNUFNXZNUUTFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2,4-dichlorophenyl)-1H-pyrrole-3-carbonitrile 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 5.5h， 生成 5-bromo-2-(2,4-dichlorophenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carbonitrile
  参考文献：
  名称：

  [EN] SUBSTITUTED PYRROLE CARBOXAMIDES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS KINASE INHIBITORS
  [FR] PYRROLE CARBOXAMIDES SUBSTITUÉS, PROCÉDÉ POUR LEUR PRÉPARATION ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE KINASE

  摘要：

  本申请涉及公式（I）的取代吡咯酰胺衍生物，其调节周期7相关蛋白激酶（Cdc7）的活性。因此，本发明的化合物在治疗与激酶活性失调相关的疾病方面具有用途，例如癌症、细胞增殖性疾病、病毒感染、免疫疾病、神经退行性疾病、心血管疾病和骨相关疾病。本申请还提供了制备这些化合物的方法、包含这些化合物的药物组合物以及它们的医学用途。

  公开号：

  WO2022207404A1

文献信息

• [EN] PROCESS FOR THE PREPARATION OF 5-(2-AMINO-PYRIMIDIN-4-YL)-2-ARYL-1H-PYRROLE-3-CARBOXAMIDES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 5-(2-AMINO- PYRIMIDIN-4-YL)-2-ARYL-LH-PYRROLE-3-CARBOXAMIDES
  申请人：NERVIANO MEDICAL SCIENCES SRL

  公开号：WO2009133170A1

  公开（公告）日：2009-11-05

  The present invention relates to a process for the preparation of 5-(2-amino- pyrimidin-4-yl)-2-aryl-lH-pyrrole-3-carboxamides and to the useful intermediate compounds of such process. 5-(2-Amino-pyrimidin-4-yl)-2-aryl-lH-pyrrole-3-carboxamides are described and claimed in WO2007110344, which also discloses processes for their preparation. These compounds can be advantageously prepared through a process which allows to obtain the desired products in high yields and purity and with a limited number of steps. The synthesis is starting from a cyano pyrrole derivative, and is characterized from the final hydrolysis of 5-(2-amino-pyrimidin-4-yl)-2-aryl-lH-pyrrole-3- carbonitrile. The compounds prepared according to the process of the present invention are endowed with protein kinase inhibiting activity and, more particularly, Cdc7 or Cdc7/Cdks inhibiting activity. The compounds are therefore useful in the treatment of a variety of cancers, cell proliferative disorders and diseases associated with protein kinases.

  本发明涉及一种制备5-(2-氨基嘧啶-4-基)-2-芳基-1H-吡咯-3-羧酰胺的方法，以及该过程中有用的中间化合物。在WO2007110344中描述并声明了5-(2-氨基嘧啶-4-基)-2-芳基-1H-吡咯-3-羧酰胺，并且还揭示了它们的制备方法。这些化合物可以通过一种允许以高收率和纯度，并且步骤有限的方法制备得到。该合成是从一个氰基吡咯衍生物开始的，并且其特点在于最终水解5-(2-氨基嘧啶-4-基)-2-芳基-1H-吡咯-3-羰基腈。根据本发明的方法制备的化合物具有蛋白激酶抑制活性，更具体地说，是Cdc7或Cdc7/Cdks抑制活性。因此，这些化合物在治疗各种癌症、细胞增殖性疾病和与蛋白激酶相关的疾病方面是有用的。
• Process for the preparation of 5-(2-amino-pyrimidin-4-yl)-2-aryl-1H-pyrrole-3-carboxamides
  申请人：D'Anello Matteo

  公开号：US08399668B2

  公开（公告）日：2013-03-19

  The present invention relates to a process for the preparation of 5-(2-amino-pyrimidin-4-yl)-2-aryl-1H-pyrrole-3-carboxamides and to the useful intermediate compounds of such process. 5-(2-Amino-pyrimidin-4-yl)-2-aryl-1H-pyrrole-3-carboxamides are described and claimed in WO2007110344, which also discloses processes for their preparation. These compounds can be advantageously prepared through a process which allows to obtain the desired products in high yields and purity and with a limited number of steps. The synthesis is starting from a cyano pyrrole derivative, and is characterized from the final hydrolysis of 5-(2-amino-pyrimidin-4-yl)-2-aryl-1H-pyrrole-3-carbonitrile. The compounds prepared according to the process of the present invention are endowed with protein kinase inhibiting activity and, more particularly, Cdc7 or Cdc7/Cdks inhibiting activity. The compounds are therefore useful in the treatment of a variety of cancers, cell proliferative disorders and diseases associated with protein kinases.

  本发明涉及一种制备5-(2-氨基嘧啶-4-基)-2-芳基-1H-吡咯-3-羧酰胺的过程以及该过程的有用中间体化合物。在WO2007110344中描述和声明了5-(2-氨基嘧啶-4-基)-2-芳基-1H-吡咯-3-羧酰胺，并且还揭示了它们的制备过程。这些化合物可以通过一种允许高产率和纯度以及少量步骤获得所需产品的过程来优势制备。合成从一个氰基吡咯衍生物开始，并以5-(2-氨基嘧啶-4-基)-2-芳基-1H-吡咯-3-碳腈的最终水解为特征。根据本发明的过程制备的化合物具有蛋白激酶抑制活性，尤其是Cdc7或Cdc7/Cdks抑制活性。因此，这些化合物在治疗各种癌症、细胞增殖性疾病和与蛋白激酶相关的疾病中非常有用。
• PROCESS FOR THE PREPARATION OF 5-(2-AMINO-PYRIMIDIN-4-YL)-2-ARYL-1H-PYRROLE-3-CARBOXAMIDES
  申请人：D'Anello Matteo

  公开号：US20110040090A1

  公开（公告）日：2011-02-17

  The present invention relates to a process for the preparation of 5-(2-amino-pyrimidin-4-yl)-2-aryl-1H-pyrrole-3-carboxamides and to the useful intermediate compounds of such process. 5-(2-Amino-pyrimidin-4-yl)-2-aryl-1H-pyrrole-3-carboxamides are described and claimed in W02007110344, which also discloses processes for their preparation. These compounds can be advantageously prepared through a process which allows to obtain the desired products in high yields and purity and with a limited number of steps. The synthesis is starting from a cyano pyrrole derivative, and is characterized from the final hydrolysis of 5-(2-amino-pyrimidin-4-yl)-2-aryl-1H-pyrrole-3-carbonitrile. The compounds prepared according to the process of the present invention are endowed with protein kinase inhibiting activity and, more particularly, Cdc7 or Cdc7/Cdks inhibiting activity. The compounds are therefore useful in the treatment of a variety of cancers, cell proliferative disorders and diseases associated with protein kinases.

  本发明涉及一种制备5-(2-氨基嘧啶-4-基)-2-芳基-1H-吡咯-3-羧酰胺的过程，以及该过程的有用中间体化合物。W02007110344中描述和声明了5-(2-氨基嘧啶-4-基)-2-芳基-1H-吡咯-3-羧酰胺，并且还揭示了它们的制备方法。这些化合物可以通过一种允许以高收率和纯度以及有限的步骤获得所需产物的过程优势地制备。合成从氰基吡咯衍生物开始，并以5-(2-氨基嘧啶-4-基)-2-芳基-1H-吡咯-3-碳腈的最终水解为特征。按照本发明的方法制备的化合物具有蛋白激酶抑制活性，特别是Cdc7或Cdc7/Cdks抑制活性。因此，这些化合物在治疗各种癌症、细胞增殖性疾病和与蛋白激酶相关的疾病中有用。
• US8399668B2
  申请人：——

  公开号：US8399668B2

  公开（公告）日：2013-03-19
• [EN] SUBSTITUTED PYRROLE CARBOXAMIDES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS KINASE INHIBITORS<br/>[FR] PYRROLE CARBOXAMIDES SUBSTITUÉS, PROCÉDÉ POUR LEUR PRÉPARATION ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE KINASE
  申请人：NERVIANO MEDICAL SCIENCES SRL

  公开号：WO2022207404A1

  公开（公告）日：2022-10-06

  The application relates to substituted pyrrole carboxamide derivatives of formula (I) which modulate the activity of cycle 7-related protein kinase (Cdc7). The compounds of this invention are therefore useful in treating diseases related to dysregulated kinases activity, for example cancer, cell proliferative disorders, viral infections, immune disorders, neurodegenerative disorders, cardiovascular diseases and bone related diseases. The application also provides methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and their medical uses.

  本申请涉及公式（I）的取代吡咯酰胺衍生物，其调节周期7相关蛋白激酶（Cdc7）的活性。因此，本发明的化合物在治疗与激酶活性失调相关的疾病方面具有用途，例如癌症、细胞增殖性疾病、病毒感染、免疫疾病、神经退行性疾病、心血管疾病和骨相关疾病。本申请还提供了制备这些化合物的方法、包含这些化合物的药物组合物以及它们的医学用途。