2-[(5-fluoropyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide | 1093871-76-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-[(5-fluoropyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide
• CAS: 1093871-76-1
• 化学式: C₁₆H₁₂FN₃OS
• 分子量: 313.355
• InChiKey: UHRZCQNOYZSYSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  benzyl [3-(aminocarbonyl)-5-iodo-2-thienyl]carbamate 在 bis-triphenylphosphine-palladium(II) chloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 palladium on activated charcoal 、 氢气 、 sodium carbonate 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 乙二醇二甲醚 、 2-甲基-2-丁醇 、 乙醇 、 水 为溶剂， 生成 2-[(5-fluoropyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide
  参考文献：
  名称：

  Thiophene carboxamide inhibitors of JAK2 as potential treatments for myleoproliferative neoplasms

  摘要：

  A series of carboxamide-substituted thiophenes demonstrating inhibition of JAK2 is described. Development of this chemical series began with the bioisosteric replacement of a urea substituent by a pyridyl ring. Issues of chemical and metabolic stability were solved using the results of both in vitro and in vivo studies, ultimately delivering compounds such as 24 and 25 that performed well in an acute PK/PD model measuring p-STAT5 inhibition. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.064

文献信息

• INHIBITORS OF JANUS KINASES
  申请人：Altman Michael

  公开号：US20100256097A1

  公开（公告）日：2010-10-07

  The instant invention provides for compounds that inhibit the four known mammalian JAK kinases (JAK1, JAK2, JAK3 and TYK2) and PDK1. The invention also provides for compositions comprising such inhibitory compounds and methods of inhibiting the activity of JAK1, JAK2, JAK3 TYK2 and PDK1 by administering the compound to a patient in need of treatment for myeloproliferative disorders or cancer.

  本发明提供了一种抑制四种已知哺乳动物JAK激酶（JAK1、JAK2、JAK3和TYK2）和PDK1的化合物。本发明还提供了包含这些抑制剂化合物的组合物和通过向需要治疗骨髓增生性疾病或癌症的患者施用该化合物来抑制JAK1、JAK2、JAK3、TYK2和PDK1活性的方法。
• US8367706B2
  申请人：——

  公开号：US8367706B2

  公开（公告）日：2013-02-05
• [EN] INHIBITORS OF JANUS KINASES<br/>[FR] INHIBITEURS DES JANUS KINASES
  申请人：MERCK & CO INC

  公开号：WO2008156726A1

  公开（公告）日：2008-12-24

  [EN] The instant invention provides for compounds that inhibit the four known mammalian JAK kinases (JAK1, JAK2, JAK3 and TYK2) and PDK1. The invention also provides for compositions comprising such inhibitory compounds and methods of inhibiting the activity of JAK1, JAK2, JAK3 TYK2 and PDK1 by administering the compound to a patient in need of treatment for myeloproliferative disorders or cancer.
  [FR] La présente invention concerne des composés qui inhibent les quatre kinases JAK mammifères connues (JAK1, JAK2, JAK3 et TYK2) et PDK1. L'invention concerne également des compositions comprenant de tels composés inhibiteurs et des procédés d'inhibition de l'activité de JAK1, JAK2, JAK3, TYK2 et PDK1 par l'administration du composé à un patient nécessitant d'un traitement pour des troubles myéloprolifératifs ou d'un cancer.
• Thiophene carboxamide inhibitors of JAK2 as potential treatments for myleoproliferative neoplasms
  作者：Andrew M. Haidle、Anna A. Zabierek、Kaleen K. Childers、Craig Rosenstein、Anjili Mathur、Michael D. Altman、Grace Chan、Lin Xu、Eric Bachman、Jan-Rung Mo、Melaney Bouthillette、Thomas Rush、Paul Tempest、C. Gary Marshall、Jonathan R. Young

  DOI：10.1016/j.bmcl.2014.02.064

  日期：2014.4

  A series of carboxamide-substituted thiophenes demonstrating inhibition of JAK2 is described. Development of this chemical series began with the bioisosteric replacement of a urea substituent by a pyridyl ring. Issues of chemical and metabolic stability were solved using the results of both in vitro and in vivo studies, ultimately delivering compounds such as 24 and 25 that performed well in an acute PK/PD model measuring p-STAT5 inhibition. (c) 2014 Elsevier Ltd. All rights reserved.