(6-amino-4-chloropyridin-3-yl)boronic acid | 1225228-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (6-amino-4-chloropyridin-3-yl)boronic acid
• 英文别名: (6-Amino-4-chloropyridin-3-yl)boronic acid
• CAS: 1225228-21-6
• 化学式: C₅H₆BClN₂O₂
• 分子量: 172.379
• InChiKey: RSNWIVDFLNKEAC-UHFFFAOYSA-N

物化性质

• 沸点：
  414.8±55.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴-4-甲基噻唑 、 (6-amino-4-chloropyridin-3-yl)boronic acid 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以350 mg的产率得到4-chloro-5-( 4-methylthiazol-2-yl)pyridin-2-amine
  参考文献：
  名称：

  [EN] INHIBITORS OF IRAK4 ACTIVITY
  [FR] INHIBITEURS DE L'ACTIVITÉ DE L'IRAK4

  摘要：

  本发明涉及调节白细胞介素-1(IL-1)受体相关激酶4(IRAK4)的化合物，适用于预防或治疗炎症、细胞增殖和免疫相关疾病和病症。具体提供了公式I的IRAK4抑制剂以及包含这些抑制剂的药物组合物，以及用于治疗IRAK4介导或相关疾病或病症的方法。

  公开号：

  WO2014058685A1
• 作为产物：
  描述：

  2-氨基-4-氯吡啶 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 potassium acetate 、 联硼酸频那醇酯 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 8.0h， 生成 (6-amino-4-chloropyridin-3-yl)boronic acid
  参考文献：
  名称：

  Identification of NVP-BKM120 as a Potent, Selective, Orally Bioavailable Class I PI3 Kinase Inhibitor for Treating Cancer

  摘要：

  Phosphoinositide-3-kinases (PI3Ks) are important oncology targets due to the deregulation of this signaling pathway in a wide variety of human cancers. Herein we describe the structure guided optimization of a series of 2-morpholino, 4-substituted, 6-heterocydic pyrirnidines where the pharmacokinetic properties were improved by modulating the electronics of the 6-position heterocycle, and the overall druglike properties were fine-tuned further by modification of the 4-position substituent. The resulting 2,4-bismorpholino 6-heterocyclic pyrirnidines are potent class I PI3K inhibitors showing mechanism modulation in PI3K dependent cell lines and in vivo efficacy in tumor xenograft models with PI3K pathway deregulation (A2780 ovarian and U87MG glioma). These efforts culminated in the discovery of 15 (NVP-BKM120), currently in Phase II clinical trials for the treatment of cancer.

  DOI：

  10.1021/ml200156t

文献信息

• INHIBITORS OF IRAK4 ACTIVITY
  申请人：SEGANISH W. Michael

  公开号：US20150299224A1

  公开（公告）日：2015-10-22

  The present invention relates to compounds which modulate interleukin-1 (IL-1) receptor-associated kinase 4 (IRAK4) and are useful in the prevention or treatment of inflammatory, cell proliferative and immune-related conditions and diseases. Specifically, provided herein are inhibitors of IRAK4 of Formula I and pharmaceutical compositions comprising such inhibitors, as well as methods therewith for treating IRAK4-mediated or -associated conditions or diseases.

  本发明涉及调节白细胞介素-1（IL-1）受体相关激酶4（IRAK4）的化合物，可用于预防或治疗炎症、细胞增殖和免疫相关的疾病和病症。具体地，本文提供了IRAK4抑制剂I式化合物和包含这些抑制剂的药物组合物，以及使用这些抑制剂的方法来治疗IRAK4介导或相关的疾病或病症。
• Identification of NVP-BKM120 as a Potent, Selective, Orally Bioavailable Class I PI3 Kinase Inhibitor for Treating Cancer
  作者：Matthew T. Burger、Sabina Pecchi、Allan Wagman、Zhi-Jie Ni、Mark Knapp、Thomas Hendrickson、Gordana Atallah、Keith Pfister、Yanchen Zhang、Sarah Bartulis、Kelly Frazier、Simon Ng、Aaron Smith、Joelle Verhagen、Joshua Haznedar、Kay Huh、Ed Iwanowicz、Xiaohua Xin、Daniel Menezes、Hanne Merritt、Isabelle Lee、Marion Wiesmann、Susan Kaufman、Kenneth Crawford、Michael Chin、Dirksen Bussiere、Kevin Shoemaker、Isabel Zaror、Sauveur-Michel Maira、Charles F. Voliva

  DOI：10.1021/ml200156t

  日期：2011.10.13

  Phosphoinositide-3-kinases (PI3Ks) are important oncology targets due to the deregulation of this signaling pathway in a wide variety of human cancers. Herein we describe the structure guided optimization of a series of 2-morpholino, 4-substituted, 6-heterocydic pyrirnidines where the pharmacokinetic properties were improved by modulating the electronics of the 6-position heterocycle, and the overall druglike properties were fine-tuned further by modification of the 4-position substituent. The resulting 2,4-bismorpholino 6-heterocyclic pyrirnidines are potent class I PI3K inhibitors showing mechanism modulation in PI3K dependent cell lines and in vivo efficacy in tumor xenograft models with PI3K pathway deregulation (A2780 ovarian and U87MG glioma). These efforts culminated in the discovery of 15 (NVP-BKM120), currently in Phase II clinical trials for the treatment of cancer.
• [EN] INHIBITORS OF IRAK4 ACTIVITY<br/>[FR] INHIBITEURS DE L'ACTIVITÉ DE L'IRAK4
  申请人：MERCK SHARP & DOHME

  公开号：WO2014058685A1

  公开（公告）日：2014-04-17

  The present invention relates to compounds which modulate interleukin-l (IL-1 ) receptor-associated kinase 4 (IRAK4) and are useful in the prevention or treatment of inflammatory, cell proliferative and immune-related conditions and diseases. Specifically, provided herein are inhibitors of IRAK4 of Formula I and pharmaceutical compositions comprising such inhibitors, as well as methods therewith for treating IRAK4-mediated or -associated conditions or diseases.

  本发明涉及调节白细胞介素-1(IL-1)受体相关激酶4(IRAK4)的化合物，适用于预防或治疗炎症、细胞增殖和免疫相关疾病和病症。具体提供了公式I的IRAK4抑制剂以及包含这些抑制剂的药物组合物，以及用于治疗IRAK4介导或相关疾病或病症的方法。