3-氨基-4-[(2-甲氧基乙基)氨基]苯甲酸 | 284672-81-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氨基-4-[(2-甲氧基乙基)氨基]苯甲酸
• 英文名称: 3-amino-4-[(2-methoxyethyl)amino]benzoic acid
• 英文别名: 3-amino-4-(2-methoxyethylamino)benzoic acid
• CAS: 284672-81-7
• 化学式: C₁₀H₁₄N₂O₃
• 分子量: 210.233
• InChiKey: YMXVSYRCBLIMJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-氨基-4-[(2-甲氧基乙基)氨基]苯甲酸 在 sodium metabisulfite 、 氯化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.67h， 生成 2-(9-ethyl-9H-carbazol-3-yl)-1-(2-methoxyethyl)-1H-benzimidazole-5-carboxamide
  参考文献：
  名称：

  Identification of a Benzimidazolecarboxylic Acid Derivative (BAY 1316957) as a Potent and Selective Human Prostaglandin E2 Receptor Subtype 4 (hEP4-R) Antagonist for the Treatment of Endometriosis

  摘要：

  The presence and growth of endometrial tissue outside the uterine cavity in endometriosis patients are primarily driven by hormone-dependent and inflammatory processes-the latter being frequently associated with severe, acute, and chronic pelvic pain. The EP4 subtype of prostaglandin E2 (PGE2) receptors (EP4-R) is a particularly promising antiinflammatory and antinociceptive target as both this receptor subtype and the pathways forming PGE2 are highly expressed in endometriotic lesions. High-throughput screening resulted in the identification of benzimidazole derivatives as novel hEP4-R antagonists. Careful structure-activity relationship investigation guided by rational design identified a methyl substitution adjacent to the carboxylic acid as an appropriate means to accomplish favorable pharmacokinetic properties by reduction of glucuronidation. Further optimization led to the identification of benzimidazolecarboxylic acid BAY 1316957, a highly potent, specific, and selective hEP4-R antagonist with excellent drug metabolism and pharmacokinetics properties. Notably, treatment with BAY 1316957 can be expected to lead to prominent and rapid pain relief and significant improvement of the patient's quality of life.

  DOI：

  10.1021/acs.jmedchem.8b01862
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸乙酯 在 palladium 10% on activated carbon 、 氢气 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 13.0h， 生成 3-氨基-4-[(2-甲氧基乙基)氨基]苯甲酸
  参考文献：
  名称：

  Novel benzimidazole derivatives as EP4 ligands

  摘要：

  本发明涉及一种新型苯并咪唑衍生物，其通式为(I)，以及其制备方法和用于制备治疗与EP4受体相关的疾病和适应症的药物组合物的用途。

  公开号：

  US20160318905A1

文献信息

• Novel benzimidazole derivatives as EP4 ligands
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20160318905A1

  公开（公告）日：2016-11-03

  The present invention relates to novel benzimidazole derivatives of the general formula (I), to processes for their preparation and to their use for preparing pharmaceutical compositions for the treatment of disorders and indications associated with the EP4 receptor.

  本发明涉及一种新型苯并咪唑衍生物，其通式为(I)，以及其制备方法和用于制备治疗与EP4受体相关的疾病和适应症的药物组合物的用途。
• NOVEL BENZIMIDAZOLE DERIVATIVES AS EP4 ANTAGONISTS
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20160214977A1

  公开（公告）日：2016-07-28

  The present invention relates to novel benzimidazole derivatives of the general formula (I), processes for their preparation and their use for the production of pharmaceutical compositions for the treatment of diseases and indications that are connected with the receptor EP4.

  本发明涉及通式(I)的新型苯并咪唑衍生物，其制备方法以及它们用于制备治疗与EP4受体相关的疾病和适应症的药物组合物的用途。
• Benzimidazole derivatives as EP4 ligands
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US10730856B2

  公开（公告）日：2020-08-04

  The present invention relates to novel benzimidazole derivatives of the general formula (I), to processes for their preparation and to their use for preparing pharmaceutical compositions for the treatment of disorders and indications associated with the EP4 receptor.

  本发明涉及通式（I）的新型苯并咪唑衍生物、其制备工艺及其用于制备治疗与 EP4 受体相关的疾病和适应症的药物组合物。
• JP2016501241A5
  申请人：——

  公开号：JP2016501241A5

  公开（公告）日：2016-01-18
• 1-Alkyl-benzotriazole-5-carboxylic Acids Are Highly Selective Agonists of the Human Orphan G-Protein-Coupled Receptor GPR109b
  作者：Graeme Semple、Philip J. Skinner、Martin C. Cherrier、Peter J. Webb、Carleton R. Sage、Susan Y. Tamura、Ruoping Chen、Jeremy G. Richman、Daniel T. Connolly

  DOI：10.1021/jm051099t

  日期：2006.2.1

  I-Substituted benzotriazole carboxylic acids have been identified as the first reported examples of selective small-molecule agonists of the human orphan G-protein-coupled receptor GPR109b (HM74), a low-affinity receptor for the HDL-raising drug niacin. No activity was observed at the highly homologous high-affinity macin receptor GPR109a (HM74A). The high degree of selectivity was attributed to a difference in the amino acid sequence adjacent to a key arginine-ligand interaction allowing somewhat larger ligands to be tolerated by GPR109b.