4-(benzylamino)-2-chloropyrimidine-5-carboxamide | 643087-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(benzylamino)-2-chloropyrimidine-5-carboxamide
• 英文别名: 4-Benzylamino-2-chloropyrimidine-5-carboxamide
• CAS: 643087-44-9
• 化学式: C₁₂H₁₁ClN₄O
• 分子量: 262.699
• InChiKey: NSDVZRDFFYGXFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(benzylamino)-2-chloropyrimidine-5-carboxamide 、 1-Boc-4-(4-氨基苯基)哌嗪 以 N-甲基吡咯烷酮 为溶剂， 生成 tert-butyl 4-(4-{[5-(aminocarbonyl)-4-(benzylamino)pyrimidin-2-yl]amino}phenyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Identification of 4-benzylamino-2-[(4-morpholin-4-ylphenyl)amino]pyrimidine-5-carboxamide derivatives as potent and orally bioavailable STAT6 inhibitors

  摘要：

  Signal transducers and activators of transcription 6 (STAT6) is a key regulator of the type 2 helper T (Th2) cell immune response and a potential therapeutic target for allergic diseases such as asthma and atopic diseases. To search for potent and orally bioavailable STAT6 inhibitors, we synthesized a series of 4-benzylaminopyrimidine-5- carboxamide derivatives and evaluated their STAT6 inhibitory activities. Among these compounds, 2-[(4-morpholin-4-ylphenyl)amino]-4-[(2,3,6- trifluorobenzyl)amino]pyrimidine-5-carboxamide (25y, YM-341619, AS1617612) showed potent STAT6 inhibition with an IC(50) of 0.70 nM, and also inhibited Th2 differentiation in mouse spleen T cells induced by interleukin (IL)-4 with an IC(50) of 0.28 nM without affecting type 1 helper T (Th1) cell differentiation induced by IL-12. In addition, compound 25y showed an oral bioavailability of 25% in mouse. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.031
• 作为产物：
  描述：

  在 ammonium hydroxide 作用下， 生成 4-(benzylamino)-2-chloropyrimidine-5-carboxamide
  参考文献：
  名称：

  Identification of 4-benzylamino-2-[(4-morpholin-4-ylphenyl)amino]pyrimidine-5-carboxamide derivatives as potent and orally bioavailable STAT6 inhibitors

  摘要：

  Signal transducers and activators of transcription 6 (STAT6) is a key regulator of the type 2 helper T (Th2) cell immune response and a potential therapeutic target for allergic diseases such as asthma and atopic diseases. To search for potent and orally bioavailable STAT6 inhibitors, we synthesized a series of 4-benzylaminopyrimidine-5- carboxamide derivatives and evaluated their STAT6 inhibitory activities. Among these compounds, 2-[(4-morpholin-4-ylphenyl)amino]-4-[(2,3,6- trifluorobenzyl)amino]pyrimidine-5-carboxamide (25y, YM-341619, AS1617612) showed potent STAT6 inhibition with an IC(50) of 0.70 nM, and also inhibited Th2 differentiation in mouse spleen T cells induced by interleukin (IL)-4 with an IC(50) of 0.28 nM without affecting type 1 helper T (Th1) cell differentiation induced by IL-12. In addition, compound 25y showed an oral bioavailability of 25% in mouse. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.031

文献信息

• 2-取代吡唑氨基-4-取代氨基-5-嘧啶甲酰胺 类化合物、组合物及其应用
  申请人：北京赛特明强医药科技有限公司

  公开号：CN109535132B

  公开（公告）日：2021-07-20

  本发明涉及作为JAK抑制剂的一类新化合物、组合物及其应用。具体地，本发明提供了一类具有强力JAK抑制活性的化合物(如式(1)所示)或其立体异构体、几何异构体、互变异构体、在药学上可接受的盐、前药、代谢产物、同位素衍生物和溶剂合物，及其包含所述化合物的药物组合物。本发明还公开了本发明化合物或药物组合物在制备药物中的应用，该药物用于治疗自身免疫疾病或癌症。
• Diaminopyrimidinecarboxa mide derivative
  申请人：Nagashima Shinya

  公开号：US20050272753A1

  公开（公告）日：2005-12-08

  A compound which may be used for the prevention or treatment of respiratory diseases in which STAT 6 is concerned, particularly asthma, chronic obstructive pulmonary disease and the like is provided. A pyrimidine derivative or a salt thereof, which has an arylamino or arylethylamino group which may be substituted with a specified substituent, at the 2-position, amino group substituted with benzyl group or the like, at the 4-position, and carbamoyl group which may be substituted, at the 5-position, is provided.

  提供了一种可用于预防或治疗呼吸道疾病，特别是哮喘、慢性阻塞性肺病等与STAT 6有关的化合物。该化合物是一种嘧啶衍生物或其盐，其在2位具有可以被指定取代基取代的芳基氨基或芳基乙基氨基，4位具有被苄基基团或类似基团取代的氨基，5位具有可以被取代的氨基甲酰基。
• Diaminopyrimidinecarboxamide Derivative
  申请人：Nagashima Shinya

  公开号：US20090281072A1

  公开（公告）日：2009-11-12

  A compound which may be used for the prevention or treatment of respiratory diseases in which STAT 6 is concerned, particularly asthma, chronic obstructive pulmonary disease and the like is provided. A pyrimidine derivative or a salt thereof, which has an arylamino or arylethylamino group which may be substituted with a specified substituent, at the 2-position, amino group substituted with benzyl group or the like, at the 4-position, and carbamoyl group which may be substituted, at the 5-position, is provided.

  提供了一种可用于预防或治疗呼吸系统疾病，特别是哮喘、慢性阻塞性肺疾病等与STAT 6有关的化合物。该化合物为嘧啶衍生物或其盐，其在2位具有可被取代的芳基氨基或芳基乙基氨基基团，4位具有氨基取代的苯甲基基团或类似基团，5位具有可被取代的氨基甲酰基团。
• DIAMINOPYRIMIDINECARBOXAMIDE DERIVATIVE
  申请人：Nagashima Shinya

  公开号：US20110294749A1

  公开（公告）日：2011-12-01

  A compound which may be used for the prevention or treatment of respiratory diseases in which STAT 6 is concerned, particularly asthma, chronic obstructive pulmonary disease and the like is provided. A pyrimidine derivative or a salt thereof, which has an arylamino or arylethylamino group which may be substituted with a specified substituent, at the 2-position, amino group substituted with benzyl group or the like, at the 4-position, and carbamoyl group which may be substituted, at the 5-position, is provided.

  提供了一种可用于预防或治疗涉及STAT 6的呼吸系统疾病，特别是哮喘、慢性阻塞性肺疾病等的化合物。该化合物为嘧啶衍生物或其盐，其在2位具有可以被指定取代基取代的芳基氨基或芳基乙基氨基基团，在4位具有可以被苄基或类似物取代的氨基基团，并在5位具有可以被取代的氨基甲酰基团。
• Diaminopyrimidinecarboxamide derivative
  申请人：Astellas Pharma, Inc.

  公开号：US07449456B2

  公开（公告）日：2008-11-11

  A compound which may be used for the prevention or treatment of respiratory diseases in which STAT 6 is concerned, particularly asthma, chronic obstructive pulmonary disease and the like is provided. A pyrimidine derivative or a salt thereof, which has an arylamino or arylethylamino group which may be substituted with a specified substituent, at the 2-position, amino group substituted with benzyl group or the like, at the 4-position, and carbamoyl group which may be substituted, at the 5-position, is provided.

  提供一种化合物，可用于预防或治疗涉及STAT 6的呼吸系统疾病，特别是哮喘、慢性阻塞性肺疾病等。该化合物是一种嘧啶衍生物或其盐，其在2位具有可以被指定取代基取代的芳基氨基或芳基乙基氨基，4位上具有被苯甲基等基团取代的氨基，5位上具有可以被取代的氨基甲酰基。