methyl 4-(N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)sulfamoyl)benzoate | 1254207-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-(N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)sulfamoyl)benzoate
• 英文别名: methyl 4-[[3-chloro-5-(trifluoromethyl)pyridin-2-yl]sulfamoyl]benzoate
• CAS: 1254207-05-0
• 化学式: C₁₄H₁₀ClF₃N₂O₄S
• 分子量: 394.759
• InChiKey: CZMZHJOWKHRKCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 4-(N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)sulfamoyl)benzoate 在 1-羟基苯并三唑 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(benzyl(3-chloro-5-(trifluoromethyl)pyridin-2-yl)sulfamoyl)-N-methylbenzamide
  参考文献：
  名称：

  Identification of a novel 2-pyridyl-benzensulfonamide derivative, RQ-00203078, as a selective and orally active TRPM8 antagonist

  摘要：

  A novel series of 2-pyridyl-benzensulfonamide derivatives have been identified as selective and orally active TRPM8 antagonists via high throughput screening (HTS). Exploration of the structure-activity relationships of compound 1 has led to the identification of RQ-00203078 (compound 36) as a highly selective, potent and orally available TRPM8 antagonist.RQ-00203078 demonstrated excellent in vivo activity in a dose dependent manner with an ED50 value of 0.65 mg/kg in the icilin-induced wet-dog shakes model in rats after oral administration and may become an important pharmacological tool for fully assessing the potential therapeutic use of the targets activated by cold stimulation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.074
• 作为产物：
  描述：

  4-(氯磺酰基)苯甲酸甲酯 、 2-氨基-3-氯-5-三氟甲基吡啶 在 二氯甲烷 、 盐酸 、 碳酸氢钠 、 magnesium sulfate 作用下， 以 吡啶 为溶剂， 反应 14.0h， 以to give 550 mg (27% yield) of methyl 4-(N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)sulfamoyl)benzoate as a dark solid that的产率得到methyl 4-(N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)sulfamoyl)benzoate
  参考文献：
  名称：

  SULFAMOYL BENZOIC ACID DERIVATIVES AS TRPM8 ANTAGONISTS

  摘要：

  本发明涉及公式（I）的磺酰苯甲酸衍生物或其药学上可接受的盐，其制备过程，含有它们的制药组合物以及它们在治疗通过TRPM8受体介导的各种疾病中的应用。

  公开号：

  US20120094964A1

文献信息

• [EN] SULFAMOYL BENZOIC ACID DERIVATIVES AS TRPM8 ANTAGONISTS<br/>[FR] DÉRIVÉS D'ACIDE SULFAMOYL BENZOÏQUE EN TANT QU'ANTAGONISTES DE TRPM8
  申请人：RAQUALIA PHARMA INC

  公开号：WO2010125831A1

  公开（公告）日：2010-11-04

  The present invention relates to sulfamoyl benzoic acid derivatives of formula (I) or a pharmaceutically acceptable salt thereof, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders which are mediated via the TRPM8 receptor.

  本发明涉及化合物的磺胺基苯甲酸衍生物（I）或其药学上可接受的盐，其制备方法，含有它们的药物组合物以及它们在治疗通过TRPM8受体介导的各种疾病中的用途。
• SULFAMOYL BENZOIC ACID DERIVATIVES AS TRPM8 ANTAGONISTS
  申请人：Inoue Tadashi

  公开号：US20120094964A1

  公开（公告）日：2012-04-19

  The present invention relates to sulfamoyl benzoic acid derivatives of formula (I) or a pharmaceutically acceptable salt thereof, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders which are mediated via the TRPM8 receptor.

  本发明涉及公式（I）的磺酰苯甲酸衍生物或其药学上可接受的盐，其制备过程，含有它们的制药组合物以及它们在治疗通过TRPM8受体介导的各种疾病中的应用。
• Identification of a novel 2-pyridyl-benzensulfonamide derivative, RQ-00203078, as a selective and orally active TRPM8 antagonist
  作者：Masashi Ohmi、Yuji Shishido、Tadashi Inoue、Kazuo Ando、Akiyoshi Fujiuchi、Akiko Yamada、Shuzo Watanabe、Kiyoshi Kawamura

  DOI：10.1016/j.bmcl.2014.10.074

  日期：2014.12

  A novel series of 2-pyridyl-benzensulfonamide derivatives have been identified as selective and orally active TRPM8 antagonists via high throughput screening (HTS). Exploration of the structure-activity relationships of compound 1 has led to the identification of RQ-00203078 (compound 36) as a highly selective, potent and orally available TRPM8 antagonist.RQ-00203078 demonstrated excellent in vivo activity in a dose dependent manner with an ED50 value of 0.65 mg/kg in the icilin-induced wet-dog shakes model in rats after oral administration and may become an important pharmacological tool for fully assessing the potential therapeutic use of the targets activated by cold stimulation. (C) 2014 Elsevier Ltd. All rights reserved.