[4-(5,9-diethoxy-8-oxo-6H-pyrrolo[3,4-g]quinolin-7-yl)-3-methylphenyl]methanesulfonamide | 915192-29-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: [4-(5,9-diethoxy-8-oxo-6H-pyrrolo[3,4-g]quinolin-7-yl)-3-methylphenyl]methanesulfonamide
• CAS: 915192-29-9
• 化学式: C₂₃H₂₅N₃O₅S
• 分子量: 455.535
• InChiKey: PSSUFWSQTYMJCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [4-(5,9-diethoxy-8-oxo-6H-pyrrolo[3,4-g]quinolin-7-yl)-3-methylphenyl]methanesulfonamide 、 alkaline earth salt of/the/ methylsulfuric acid 生成 N-{[4-(5,9-diethoxy-8-oxo-6,8-dihydro-7H-pyrrolo[3,4-g]quinolin-7-yl)-3-methylbenzyl]sulfonyl}-2-phenylacetamide
  参考文献：
  名称：

  Structure–activity relationships and pharmacokinetic parameters of quinoline acylsulfonamides as potent and selective antagonists of the EP4 receptor

  摘要：

  A new series of EP4 antagonists based on a quinoline acylsulfonamide scaffold have been identified as part of our ongoing efforts to develop treatments for chronic inflammation. These compounds show subnanomolar intrinsic binding potency towards the EP4 receptor, and excellent selectivity towards other prostanoid receptors. Acceptable pharmacokinetic profiles have also been demonstrated across a series of preclinical species. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.103
• 作为产物：
  描述：

  N-tert-butyl-1-[4-(5,9-diethoxy-6,8-dioxopyrrolo[3,4-g]quinolin-7-yl)-3-methylphenyl]methanesulfonamide 在 sodium tetrahydroborate 、 三乙基硅烷 、 三氟乙酸 作用下， 生成 [4-(5,9-diethoxy-6-oxo-8H-pyrrolo[3,4-g]quinolin-7-yl)-3-methylphenyl]methanesulfonamide 、 [4-(5,9-diethoxy-8-oxo-6H-pyrrolo[3,4-g]quinolin-7-yl)-3-methylphenyl]methanesulfonamide
  参考文献：
  名称：

  Structure–activity relationships and pharmacokinetic parameters of quinoline acylsulfonamides as potent and selective antagonists of the EP4 receptor

  摘要：

  A new series of EP4 antagonists based on a quinoline acylsulfonamide scaffold have been identified as part of our ongoing efforts to develop treatments for chronic inflammation. These compounds show subnanomolar intrinsic binding potency towards the EP4 receptor, and excellent selectivity towards other prostanoid receptors. Acceptable pharmacokinetic profiles have also been demonstrated across a series of preclinical species. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.103

文献信息

• Quinoline derivatives as ep4 antagonists
  申请人：Belley Michel

  公开号：US20090099226A1

  公开（公告）日：2009-04-16

  The invention is directed to quinoline derivatives as prostaglandin E type receptor antagonists useful for the treatment of EP4 mediated diseases or conditions, such as acute and chronic pain, osteoarthritis, rheumatoid arthritis and cancer. The derivatives have the following structure of formula (I): wherein A and B represents either a nitrogen atom or a CH group with the proviso that they cannot both simultaneously be CH, Q can represent a nitrogen or a carbon atom, and Y and Z are either a nitrogen atom, a N(O) group or a C(R 5 ) group. Pharmaceutical compositions comprising the derivatives of formula (I) are also included.

  本发明涉及喹啉衍生物作为前列腺素E类型受体拮抗剂，用于治疗EP4介导的疾病或症状，如急性和慢性疼痛、骨关节炎、类风湿性关节炎和癌症。这些衍生物具有以下结构式（I）：其中A和B表示氮原子或CH基团，但不能同时为CH，Q可以表示氮原子或碳原子，Y和Z可以是氮原子、N（O）基团或C（R5）基团。还包括含有式（I）的衍生物的制药组合物。
• WO2006/122403
  申请人：——

  公开号：——

  公开（公告）日：——
• QUINOLINE DERIVATIVES AS EP4 ANTAGONISTS
  申请人：Merck Canada Inc.

  公开号：EP1885722B1

  公开（公告）日：2011-11-16
• US8013159B2
  申请人：——

  公开号：US8013159B2

  公开（公告）日：2011-09-06
• Structure–activity relationships and pharmacokinetic parameters of quinoline acylsulfonamides as potent and selective antagonists of the EP4 receptor
  作者：Jason D. Burch、Michel Belley、Réjean Fortin、Denis Deschênes、Mario Girard、John Colucci、Julie Farand、Alex G. Therien、Marie-Claude Mathieu、Danielle Denis、Erika Vigneault、Jean-François Lévesque、Sébastien Gagné、Mark Wrona、Daigen Xu、Patsy Clark、Steve Rowland、Yongxin Han

  DOI：10.1016/j.bmcl.2008.01.103

  日期：2008.3

  A new series of EP4 antagonists based on a quinoline acylsulfonamide scaffold have been identified as part of our ongoing efforts to develop treatments for chronic inflammation. These compounds show subnanomolar intrinsic binding potency towards the EP4 receptor, and excellent selectivity towards other prostanoid receptors. Acceptable pharmacokinetic profiles have also been demonstrated across a series of preclinical species. (c) 2008 Elsevier Ltd. All rights reserved.