ethyl 3-nitro-4-[(3-methoxypropyl)amino]benzoate | 1256937-01-5

• 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: ethyl 3-nitro-4-[(3-methoxypropyl)amino]benzoate
• 英文别名: Ethyl 4-[(3-methoxypropyl)amino]-3-nitrobenzoate；ethyl 4-(3-methoxypropylamino)-3-nitrobenzoate
• CAS: 1256937-01-5
• 化学式: C₁₃H₁₈N₂O₅
• 分子量: 282.296
• InChiKey: YFLMGBHWIWRQBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-nitro-4-[(3-methoxypropyl)amino]benzoate 在 sodium dithionite 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 ethyl 3-amino-4-[(3-methoxypropyl)amino]benzoate
  参考文献：
  名称：

  Discovery of 2-aminoimidazopyridine adenosine A2A receptor antagonists

  摘要：

  A novel series of adenosine A(2A) receptor antagonists was identified by high-throughput screening of an encoded combinatorial compound collection. The initial hits were optimized for A(2A) binding affinity, A(1) selectivity, and in vitro microsomal stability generating orally available 2-aminoimidazo[4,5-b]pyridinebased A(2A) antagonist leads. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.08.064
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸乙酯 、 3-甲氧基丙胺 以 二甲基亚砜 为溶剂， 生成 ethyl 3-nitro-4-[(3-methoxypropyl)amino]benzoate
  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

文献信息

• 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。
• NEUARTIGE BENZIMIDAZOLDERIVATE ALS EP4-ANTAGONISTEN
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP2928884A1

  公开（公告）日：2015-10-14
• US9708311B2
  申请人：——

  公开号：US9708311B2

  公开（公告）日：2017-07-18
• [DE] NEUARTIGE BENZIMIDAZOLDERIVATE ALS EP4-ANTAGONISTEN<br/>[EN] NOVEL BENZIMIDAZOLE DERIVATIVES AS EP4 ANTAGONISTS<br/>[FR] NOUVEAUX DÉRIVÉS DU BENZIMIDAZOLE COMME ANTAGONISTES EP4
  申请人：BAYER PHARMA AG

  公开号：WO2014086739A1

  公开（公告）日：2014-06-12

  Die vorliegende Erfindung betrifft neuartige Benzimidazolderivate der allgemeinen Formel (I), Verfahren zu ihrer Herstellung sowie deren Verwendung zur Herstellung von pharmazeutischen Mitteln zur Behandlung von Erkrankungen und Indikationen, die im Zusammenhang stehen mit dem Rezeptor EP4.