N-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxamide | 1075753-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxamide
• 英文别名: N-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-5-carboxamide；5-methylcarbamoyl-1,3-dihydro-2H-benzimidazol-2-one；N-methyl-2-oxo-1,3-dihydrobenzimidazole-5-carboxamide
• CAS: 1075753-22-8
• 化学式: C₉H₉N₃O₂
• mdl: MFCD24390588
• 分子量: 191.189
• InChiKey: KWTVMNDOKRKPOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  70.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxamide 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 生成 2-chloro-N-methyl-3H-benzimidazole-5-carboxamide
  参考文献：
  名称：

  Design, syntheses, and structure–activity relationships of novel NPY Y5 receptor antagonists: 2-{3-Oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole derivatives

  摘要：

  Design, syntheses, and structure-activity relationships of a novel class of 2-{3-oxospiro[isobenzofuran-1(3H),4'-piperidin]-1'-yl}benzimidazole NPY Y5 receptor antagonists are described. The benzimidazole structures were newly designed based on the urea linkage of our prototype Y5 receptor antagonists (2 and 3). By optimizing substituents on the benzimidazole core part of the lead compound 5a, we were able to develop a potent, orally available, and brain-penetrable Y5 selective antagonist (5k). Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.018

文献信息

• SUBSTITUTED IMIDAZOLIDINONE DERIVATIVES
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP1221443A1

  公开（公告）日：2002-07-10

  This invention relates to the compounds represented by the general formula [I],    [in which A-D signify optionally substituted methine group(s) or nitrogen atom; E signifies oxygen or sulfur atom; signify optionally substituted mono- or bi-cyclic aliphatic nitrogen-containing heterocyclic group(s); R1 signifies lower alkenyl, lower alkynyl, cyclo(lower alkyl), lower alkanoyl, lower alkoxycarbonyl, optionally substituted lower alkyl and the like; and R2 signifies lower alkyl]. The compounds of the present invention exhibit an action to stimulate muscarinic acetylcholine receptors M4, and are useful as analgesic for diseases accompanying pain such as cancerous pain, migraine, gout, chronic rheumatism, chronic pain or neuralgia; or as agents for treating tolerance to narcotic analgesics represented by morphine, dependence on narcotic analgesics represented by morphine, itching, dementia, irritable bowel syndrome, schizophrenia, glaucoma, pollakiuria, urinary incontinence, cholelithiasis, cholecystitis, functional dyspepsia and reflux esophagitis.

  本发明涉及通式[I]所代表的化合物、 [其中 A-D 表示任选取代的甲基或氮原子；E 表示氧原子或硫原子； 表示任选取代的单环或双环脂肪族含氮杂环基团；R1 表示低级烯基、低级炔基、环（低级烷基）、低级烷酰基、低级烷氧羰基、任选取代的低级烷基等；R2 表示低级烷基]。 本发明的化合物具有刺激毒蕈碱乙酰胆碱受体 M4 的作用，可作为镇痛剂用于治疗伴随疼痛的疾病，如癌性疼痛、偏头痛、痛风、慢性风湿病、慢性疼痛或神经痛；或作为治疗对以吗啡为代表的麻醉性镇痛剂的耐受性、对以吗啡为代表的麻醉性镇痛剂的依赖性、瘙痒、痴呆、肠易激综合征、精神分裂症、青光眼、花斑尿、尿失禁、胆石症、胆囊炎、功能性消化不良和反流性食管炎的药物。
• US6699880B1
  申请人：——

  公开号：US6699880B1

  公开（公告）日：2004-03-02
• Design, syntheses, and structure–activity relationships of novel NPY Y5 receptor antagonists: 2-{3-Oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole derivatives
  作者：Yoshio Ogino、Norikazu Ohtake、Yoshikazu Nagae、Kenji Matsuda、Minoru Moriya、Takuya Suga、Makoto Ishikawa、Maki Kanesaka、Yuko Mitobe、Junko Ito、Tetsuya Kanno、Akane Ishihara、Hisashi Iwaasa、Tomoyuki Ohe、Akio Kanatani、Takehiro Fukami

  DOI：10.1016/j.bmcl.2008.08.018

  日期：2008.9

  Design, syntheses, and structure-activity relationships of a novel class of 2-3-oxospiro[isobenzofuran-1(3H),4'-piperidin]-1'-yl}benzimidazole NPY Y5 receptor antagonists are described. The benzimidazole structures were newly designed based on the urea linkage of our prototype Y5 receptor antagonists (2 and 3). By optimizing substituents on the benzimidazole core part of the lead compound 5a, we were able to develop a potent, orally available, and brain-penetrable Y5 selective antagonist (5k). Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.