3-溴-7-氯-5-甲基-1H-吡唑并[4,3-b]吡啶 | 268547-53-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 中文名称: 3-溴-7-氯-5-甲基-1H-吡唑并[4,3-b]吡啶
• 英文名称: 3-bromo-7-chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine
• 英文别名: 3-Bromo-5-methyl-7-chloro-pyrazolo[4,3-b]pyridine；3-bromo-7-chloro-5-methyl-2H-pyrazolo[4,3-b]pyridine
• CAS: 268547-53-1
• 化学式: C₇H₅BrClN₃
• 分子量: 246.494
• InChiKey: WPVDNHUFUJJDKA-UHFFFAOYSA-N

物化性质

• 沸点：
  373.4±37.0 °C(Predicted)
• 密度：
  1.857±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-溴-7-氯-5-甲基-1H-吡唑并[4,3-b]吡啶 在 barium dihydroxide 、 四(三苯基膦)钯 、 氢溴酸 、 sodium hydride 、 sodium carbonate 、 对甲苯磺酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 89.25h， 生成 (10S)-3-(2-chloro-4-fluorophenyl)-9-(cyclopropylmethyl)-10-ethyl-6-methyl-1,2,5,9-tetrazatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraene
  参考文献：
  名称：

  Design and Synthesis of Tricyclic Corticotropin-Releasing Factor-1 Antagonists

  摘要：

  Antagonists of the corticotropin-releasing factor (CRF) neuropeptide should prove to be effective in treating stress and anxiety-related disorders. In an effort to identify antagonists with improved physicochemical properties, new tricyclic CRF, antagonists were designed, synthesized, and tested for biological activity. As a result of studies aimed at establishing a relationship between structure and CRF, binding affinity, NBI 35965 (12a) was identified as a high-affinity antagonist with a pK(i) value of 8.5. Compound 12a proved to be a functional CRF, antagonist with pIC(50) values of 7.1 and 6.9 in the in vitro CRF-stimulated cAMP accumulation and ACTH production assays, respectively, and 12a also reduced CRF or stress induced ACTH production in vivo.

  DOI：

  10.1021/jm049085v
• 作为产物：
  描述：

  7-氯-5-甲基-1H-吡唑并[4,3-b]-吡啶 在 溴 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以98%的产率得到3-溴-7-氯-5-甲基-1H-吡唑并[4,3-b]吡啶
  参考文献：
  名称：

  Design and Synthesis of Tricyclic Corticotropin-Releasing Factor-1 Antagonists

  摘要：

  Antagonists of the corticotropin-releasing factor (CRF) neuropeptide should prove to be effective in treating stress and anxiety-related disorders. In an effort to identify antagonists with improved physicochemical properties, new tricyclic CRF, antagonists were designed, synthesized, and tested for biological activity. As a result of studies aimed at establishing a relationship between structure and CRF, binding affinity, NBI 35965 (12a) was identified as a high-affinity antagonist with a pK(i) value of 8.5. Compound 12a proved to be a functional CRF, antagonist with pIC(50) values of 7.1 and 6.9 in the in vitro CRF-stimulated cAMP accumulation and ACTH production assays, respectively, and 12a also reduced CRF or stress induced ACTH production in vivo.

  DOI：

  10.1021/jm049085v

文献信息

• CRF receptor antagonists and methods relating thereto
  申请人：Neurocrine Biosciences, Inc.

  公开号：US20040087589A1

  公开（公告）日：2004-05-06

  CRF receptor antagonists are disclosed which have utility in the treatment of a variety of disorders, including the treatment of disorders manifesting hypersecretion of CRF in a warm-blooded animals, such as stroke. The CRF receptor antagonists of this invention have the following structure: 1 including stereoisomers and pharmaceutically acceptable salts thereof, wherein n, m, A, B, C, R, R 1 , R 2 and Ar are as defined herein. Compositions containing a CRF receptor antagonist in combination with a pharmaceutically acceptable carrier are also disclosed, as well as methods for use of the same

  本发明揭示了CRF受体拮抗剂，其在治疗多种疾病中具有用途，包括治疗温血动物中CRF过度分泌的疾病，如中风。本发明的CRF受体拮抗剂具有以下结构：1包括立体异构体和其药学上可接受的盐，其中n，m，A，B，C，R，R1，R2和Ar如本文所定义。还揭示了含有CRF受体拮抗剂和药学上可接受的载体的组合物，以及使用它们的方法。
• Crf Receptor Antagonists And Methods Relating Thereto
  申请人：Lanier Marion

  公开号：US20080064719A1

  公开（公告）日：2008-03-13

  CRF receptor antagonists are disclosed which may have utility in the treatment of a variety of disorders, including the treatment of disorders manifesting hypersecretion of CRF in mammals, such as stroke. The CRF receptor antagonists of this invention have the following structure: and pharmaceutically acceptable salts, esters, solvates, stereoisomers and prodrugs thereof, wherein R 1 , R 2 , n, R 5 , Ar, and Het are as defined herein. Compositions containing a CRF receptor antagonists in combination with a pharmaceutically acceptable carrier are also disclosed, as well as methods for use of the same.

  本发明公开了CRF受体拮抗剂，可用于治疗多种疾病，包括治疗哺乳动物中CRF分泌过多表现的疾病，如中风。本发明的CRF受体拮抗剂具有以下结构：以及其药学上可接受的盐、酯、溶剂合物、立体异构体和前药，其中R1、R2、n、R5、Ar和Het的定义如本文所述。本发明还公开了含有CRF受体拮抗剂和药学上可接受的载体的组合物，以及使用它们的方法。
• WO2006/44821
  申请人：——

  公开号：——

  公开（公告）日：——
• CRF RECEPTOR ANTAGONISTS AND METHODS RELATING THERETO
  申请人：Neurocrine Biosciences, Inc.

  公开号：EP1129091B1

  公开（公告）日：2002-10-02
• US6514982B1
  申请人：——

  公开号：US6514982B1

  公开（公告）日：2003-02-04