N-cyclopentyl-N-methyl-4-(3-nitrophenyl)-1H-imidazole-1-carboxamide | 1356960-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-cyclopentyl-N-methyl-4-(3-nitrophenyl)-1H-imidazole-1-carboxamide
• 英文别名: N-cyclopentyl-N-methyl-4-(3-nitrophenyl)imidazole-1-carboxamide
• CAS: 1356960-85-4
• 化学式: C₁₆H₁₈N₄O₃
• 分子量: 314.344
• InChiKey: OIPQMWUMUMFFKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-cyclopentyl-N-methyl-4-(3-nitrophenyl)-1H-imidazole-1-carboxamide 在 palladium 10% on activated carbon 、 甲酸铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 19.0h， 生成 N-cyclopentyl-N-methyl-4-(3-ureidophenyl)-1H-imidazole-1-carboxamide
  参考文献：
  名称：

  [EN] PROCESSES FOR THE SYNTHESIS OF SUBSTITUTED UREA COMPOUNDS
  [FR] PROCÉDÉS DE SYNTHÈSE DE COMPOSÉS D'URÉE SUBSTITUÉS

  摘要：

  公开号：

  WO2015112036A3
• 作为产物：
  描述：

  2-溴-3'-硝基苯乙酮 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 6.5h， 生成 N-cyclopentyl-N-methyl-4-(3-nitrophenyl)-1H-imidazole-1-carboxamide
  参考文献：
  名称：

  [EN] UREA COMPOUNDS AND THEIR USE AS ENZYME INHIBITORS
  [FR] COMPOSÉS D'URÉE ET LEUR UTILISATION EN TANT QU'INHIBITEURS D'ENZYME

  摘要：

  公开号：

  WO2014017936A3

文献信息

• PROCESS FOR THE SYNTHESIS OF SUBSTITUTED UREA COMPOUNDS
  申请人：Learmonth David Alexander

  公开号：US20130123493A1

  公开（公告）日：2013-05-16

  A process for preparing a substitute urea of Formula (II) or Formula (I), or a pharmaceutically acceptable salt or ester thereof, Formula (II): Formula (I): the process comprising the reaction of a carbamate of Formula (II′): or formula (I′): with a primary or secondary amine of the formula: R1R2NH, wherein ring A, and R1, R2, R5, V, W, X, Y and Z are as defined herein.

  一种制备公式（II）或公式（I）的替代尿素或其药学上可接受的盐或酯的方法，公式（II）：公式（I）：该方法包括将公式（II'）的氨基甲酸酯或公式（I'）的氨基甲酸酯与公式为R1R2NH的一次或二次胺反应，其中环A、R1、R2、R5、V、W、X、Y和Z在此定义。
• UREA COMPOUNDS AND THEIR USE AS ENZYME INHIBITORS
  申请人：BIAL-PORTELA & CA, S.A.

  公开号：US20150174103A1

  公开（公告）日：2015-06-25

  A compound having the following structure: or a pharmaceutically acceptable salt or derivative thereof. The compound may be used in the treatment or prevention of a disorder selected from appetite regulation, obesity, metabolic disorders, cachexia, anorexia, pain, inflammation, neurotoxicity, neurotrauma, stroke, multiple sclerosis, spinal cord injury, Parkinson's disease, levodopa-induced dyskinesia, Huntington's disease, Gilles de la Tourette's syndrome, tardive dyskinesia, dystonia, amyotrophic lateral sclerosis, Alzheimer's disease, epilepsy, schizophrenia, anxiety, depression, insomnia, nausea, emesis, alcohol disorders, drug addictions such as opiates, nicotine, cocaine, alcohol and psychostimulants, hypertension, circulatory shock, myocardial reperfusion injury, atherosclerosis, asthma, glaucoma, retinopathy, cancer, inflammatory bowel disease, acute and chronic liver disease such as hepatitis and liver cirrhosis, arthritis and osteoporosis.

  一种具有以下结构的化合物：或其药学上可接受的盐或衍生物。该化合物可用于治疗或预防以下疾病：食欲调节、肥胖症、代谢紊乱、消瘦、厌食症、疼痛、炎症、神经毒性、神经创伤、中风、多发性硬化、脊髓损伤、帕金森病、左旋多巴诱发的运动障碍、亨廷顿病、吉尔·德·拉·图雷特综合征、迟发性运动障碍、肌张力障碍、肌萎缩性侧索硬化症、阿尔茨海默病、癫痫、精神分裂症、焦虑症、抑郁症、失眠、恶心、呕吐、酒精障碍、药物成瘾（如鸦片、尼古丁、可卡因、酒精和精神兴奋剂）、高血压、循环性休克、心肌再灌注损伤、动脉粥样硬化、哮喘、青光眼、视网膜病变、癌症、炎症性肠病、急性和慢性肝病（如肝炎和肝硬化）、关节炎和骨质疏松症。
• Urea compounds and their use as enzyme inhibitors
  申请人：BIAL-PORTELA & CA, S.A.

  公开号：US10023541B2

  公开（公告）日：2018-07-17

  A compound having the following structure: or a pharmaceutically acceptable salt or derivative thereof. The compound may be used in the treatment or prevention of a disorder selected from appetite regulation, obesity, metabolic disorders, cachexia, anorexia, pain, inflammation, neurotoxicity, neurotrauma, stroke, multiple sclerosis, spinal cord injury, Parkinson's disease, levodopa-induced dyskinesia, Huntington's disease, Gilles de la Tourette's syndrome, tardive dyskinesia, dystonia, amyotrophic lateral sclerosis, Alzheimer's disease, epilepsy, schizophrenia, anxiety, depression, insomnia, nausea, emesis, alcohol disorders, drug addictions such as opiates, nicotine, cocaine, alcohol and psychostimulants, hypertension, circulatory shock, myocardial reperfusion injury, atherosclerosis, asthma, glaucoma, retinopathy, cancer, inflammatory bowel disease, acute and chronic liver disease such as hepatitis and liver cirrhosis, arthritis and osteoporosis.

  具有以下结构的化合物 或其药学上可接受的盐或衍生物。多发性硬化症、脊髓损伤、帕金森病、左旋多巴诱发的运动障碍、亨廷顿氏病、吉尔-德-图雷特综合征、迟发性运动障碍、肌张力障碍、肌萎缩性脊髓侧索硬化症、阿尔茨海默氏症、癫痫、精神分裂症、颅内压增高、颅内压增高和颅内压增高、癫痫、精神分裂症、焦虑、抑郁、失眠、恶心、呕吐、酒精紊乱、药物成瘾（如鸦片制剂、尼古丁、可卡因、酒精和精神兴奋剂）、高血压、循环休克、心肌再灌注损伤、动脉粥样硬化、哮喘、青光眼、视网膜病变、癌症、炎症性肠病、急慢性肝病（如肝炎和肝硬化）、关节炎和骨质疏松症。
• Processes for the synthesis of substituted urea compounds
  申请人：BIAL-PORTELA & Ca, S.A.

  公开号：US11078163B2

  公开（公告）日：2021-08-03

  The present invention concerns a process for preparing a compound having the Formula A; or a pharmaceutically acceptable salt or derivative thereof, or for preparing a substituted urea compound of Formula IIa, or a pharmaceutically acceptable salt or ester thereof, the process comprising the reaction of an imidazolyl intermediate of Formula IIa′ with a carbamoyl halide of the formula: R1R2NC(═O)Hal, wherein Hal represents Cl, F, I or Br, wherein the intermediate of Formula IIa′ is prepared by oxidation of the derivative of R5 and R6, R6-C(═O)CH2R5 to form a glyoxal intermediate R6-C(═O)(C═O)R5, which is subjected to treatment with ammonium hydroxide and an aldehyde R8CHO to provide the intermediate of Formula IIa′ and wherein the compound substituents are as defined herein.

  本发明涉及一种制备具有式A的化合物或其药学上可接受的盐或衍生物的工艺，或制备式IIa的取代脲化合物或其药学上可接受的盐或酯的工艺，该工艺包括式IIa′的咪唑中间体与式的氨基甲酰卤反应：R1R2NC(═O)Hal，其中Hal代表Cl、F、I或Br，式Ⅱa′的中间体是由R5和R6的衍生物R6-C(═O)CH2R5氧化制备成乙二醛中间体R6-C(═O)(C═O)R5、经氢氧化铵和醛 R8CHO 处理，得到式 IIa′的中间体，其中化合物取代基如本文所定义。
• PROCES FOR THE SYNTHESIS OF SUBSTITUTED UREA COMPOUNDS
  申请人：BIAL - Portela & CA., S.A.

  公开号：EP2606035B1

  公开（公告）日：2017-09-06