5-(4-Chloro-2-ethoxyphenyl)-4-methyl-1,2-oxazole-3-carbonyl chloride | 1110772-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-Chloro-2-ethoxyphenyl)-4-methyl-1,2-oxazole-3-carbonyl chloride
• 英文别名: 5-(4-chloro-2-ethoxyphenyl)-4-methyl-1,2-oxazole-3-carbonyl chloride
• CAS: 1110772-00-3
• 化学式: C₁₃H₁₁Cl₂NO₃
• 分子量: 300.141
• InChiKey: MASNTORXYCKMNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3R)-3-氨基环己醇 、 5-(4-Chloro-2-ethoxyphenyl)-4-methyl-1,2-oxazole-3-carbonyl chloride 在 三乙胺 作用下， 生成 5-(4-chloro-2-ethoxyphenyl)-N-((1R,3S)-3-hydroxycyclohexyl)-4-methylisoxazole-3-carboxamide
  参考文献：
  名称：

  Discovery of potent, soluble and orally active TRPV1 antagonists. Structure–activity relationships of a series of isoxazoles

  摘要：

  Systematic optimisation of a poorly soluble lead series of isoxazole-3-carboxamides was conducted. Substitution of the 4-position with specific polar functionality afforded the requisite balance of potency, solubility and physicochemical properties. Compound 21a was found to be efficacious in the rat Capsaicin Hargreaves assay following oral administration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.051
• 作为产物：
  描述：

  5-溴-4-甲基异恶唑-3-羧酸乙酯 在 甲醇 、 四(三苯基膦)钯 、 草酰氯 、 potassium carbonate 、 lithium 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 5-(4-Chloro-2-ethoxyphenyl)-4-methyl-1,2-oxazole-3-carbonyl chloride
  参考文献：
  名称：

  Discovery of potent, soluble and orally active TRPV1 antagonists. Structure–activity relationships of a series of isoxazoles

  摘要：

  Systematic optimisation of a poorly soluble lead series of isoxazole-3-carboxamides was conducted. Substitution of the 4-position with specific polar functionality afforded the requisite balance of potency, solubility and physicochemical properties. Compound 21a was found to be efficacious in the rat Capsaicin Hargreaves assay following oral administration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.051

文献信息

• [EN] 5-PHENYL-ISOXAZOLE-3-CARBOXAMIDE DERIVATIVES AS TRPV1 MODULATORS<br/>[FR] DÉRIVÉS D'ISOXAZOLE-3-CARBOXAMIDE
  申请人：ORGANON NV

  公开号：WO2009016241A1

  公开（公告）日：2009-02-05

  The present invention relates to isoxazole-3-carboxamide derivative having the general Formula (I), or a pharmaceutically acceptable salt thereof, to pharmaceutical compositions comprising the same, as well as to the use of said isoxazole-3-carboxamide derivatives for the treatment of TRPV1 mediated disorders, such as acute and chronic pain disorders, acute and chronic neuropathic pain, acute and chronic inflammatory pain, respiratory diseases, and lower urinary tract disorders.

  本发明涉及具有通式（I）的异噁唑-3-羧酰胺衍生物，或其药学上可接受的盐，包括含有相同成分的药物组合物，以及所述异噁唑-3-羧酰胺衍生物用于治疗TRPV1介导的疾病，如急性和慢性疼痛疾病、急性和慢性神经病性疼痛、急性和慢性炎症性疼痛、呼吸道疾病和下尿路疾病。
• 5- PHENYL-ISOXAZOLE-3-CARBOXAMIDE DERIVATIVES AS TRPV1 MODULATORS
  申请人：Roughton Andrew Laird

  公开号：US20110065764A1

  公开（公告）日：2011-03-17

  The present invention relates to isoxazole-3-carboxamide derivative having the general Formula (I), or a pharmaceutically acceptable salt thereof, to pharmaceutical compositions comprising the same, as well as to the use of said isoxazole-3-carboxamide derivatives for the treatment of TRPV1 mediated disorders, such as acute and chronic pain disorders, acute and chronic neuropathic pain, acute and chronic inflammatory pain, respiratory diseases, and lower urinary tract disorders.

  本发明涉及一种具有一般式(I)的异恶唑-3-羧酰胺衍生物，或其药学上可接受的盐，以及包含它们的药物组合物，以及使用所述异恶唑-3-羧酰胺衍生物治疗TRPV1介导的疾病，如急性和慢性疼痛疾病，急性和慢性神经病性疼痛，急性和慢性炎症性疼痛，呼吸系统疾病和下尿路疾病的用途。
• 5-PHENYL-ISOXAZOLE-3-CARBOXAMIDE DERIVATIVES AS TRPV1 MODULATORS
  申请人：N.V. Organon

  公开号：EP2185530B1

  公开（公告）日：2011-09-14
• US8211927B2
  申请人：——

  公开号：US8211927B2

  公开（公告）日：2012-07-03