1-(3-methylbutyl)-1,3-dihydro-2H-benzimidazol-2-one | 305347-10-8

• 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: 1-(3-methylbutyl)-1,3-dihydro-2H-benzimidazol-2-one
• 英文别名: 1-isopentyl-1H-benzo[d]imidazol-2(3H)-one；3-(3-methylbutyl)-1H-benzimidazol-2-one
• CAS: 305347-10-8
• 化学式: C₁₂H₁₆N₂O
• mdl: MFCD01955755
• 分子量: 204.272
• InChiKey: ALKJFGJPEBAMNI-UHFFFAOYSA-N

物化性质

• 溶解度：
  >30.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-methylbutyl)-1,3-dihydro-2H-benzimidazol-2-one 、 6-Cbz-aminohexyl bromide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS COMPRISING PROTEINASE ACTIVATED RECEPTOR ANTAGONISTS
  [FR] COMPOSITIONS ET PROCEDES COMPORTANT DES ANTAGONISTES DE RECEPTEUR ACTIVE PAR LA PROTEINASE

  摘要：

  公开号：

  WO2006023844A3
• 作为产物：
  描述：

  1-溴代异戊烷 生成 1-(3-methylbutyl)-1,3-dihydro-2H-benzimidazol-2-one
  参考文献：
  名称：

  WO2006/97808

  摘要：

  公开号：

文献信息

• BENZIMIDAZOLONE DERIVATIVES
  申请人：Ando Kazuo

  公开号：US20090298811A1

  公开（公告）日：2009-12-03

  This invention relates to compounds and methods for the treatment of a condition mediated by CB1 receptor activity in a mammalian subject including a human, which comprises administering to a mammal in need of such treatment a therapeutically effective amount of the compound of formula (I) or pharmaceutically acceptable salts thereof, wherein: A, B, R 1 , R 2 and R 3 are each as described herein. These compounds are useful in the treatment of a condition mediated by CB2 receptor binding activity such as, but not limited to, inflammatory pain, nociceptive pain, neuropathic pain, fibromyalgia, chronic low back pain, visceral pain, acute cerebral ischemia, pain, chronic pain, acute pain, post herpetic neuralgia, neuropathies, neuralgia, diabetic neuropathy, HIV-related neuropathy, nerve injury, rheumatoid arthritic pain, osteoarthritic pain, back pain, cancer pain, dental pain, fibromyalgia, neuritis, sciatica, inflammation, neurodegenerative disease, spasticity, epilepsy, Tourette's syndrome, Parkinson's disease, neuroprotection, anxiety, cough, broncho constriction, irritable bowel syndrome (IBS), inflammatory bowel disease (IBD), colitis, cerebrovascular ischemia, cachexia, nausea, emesis, chemotherapy-induced emesis, rheumatoid arthritis, asthma, Crohn's disease, ulcerative colitis, asthma, dermatitis, seasonal allergic rhinitis, gastroesophageal reflux disease (GERD), constipation, diarrhea, functional gastrointestinal disorder, cutaneous T cell lymphoma, multiple sclerosis, osteoarthritis, psoriasis, systemic lupus erythematosus, diabetes, glaucoma, osteoporosis, glomerulonephritis, renal ischemia, nephritis, hepatitis, cerebral stroke, vasodialation, hypertension, vasculitis, myocardial infarction, cerebral ischemia, reversible airway obstruction, adult respiratory disease syndrome, chronic obstructive pulmonary disease (COPD), cryptogenic fibrosing alveolitis and bronchitis.

  本发明涉及化合物和方法，用于治疗由CB1受体活性在哺乳动物主体中介导的疾病，包括人类，其包括向需要该治疗的哺乳动物施用化合物的治疗有效量的公式(I)或其药用可接受盐，其中：A、B、R1、R2和R3如本文所述。这些化合物在治疗由CB2受体结合活性介导的疾病中有用，如但不限于炎症性疼痛、伤害性疼痛、神经性疼痛、纤维肌痛、慢性腰痛、内脏疼痛、急性脑缺血、疼痛、慢性疼痛、急性疼痛、带状疱疹后神经痛、神经病、神经痛、糖尿病性神经病、艾滋病相关神经病、神经损伤、类风湿性关节炎疼痛、骨关节炎疼痛、背部疼痛、癌症疼痛、牙痛、纤维肌痛、神经炎、坐骨神经痛、炎症、神经退行性疾病、痉挛、癫痫、托瑞特综合征、帕金森病、神经保护、焦虑、咳嗽、支气管痉挛、肠易激综合征（IBS）、炎症性肠病（IBD）、结肠炎、脑血管缺血、虚弱、恶心、呕吐、化疗诱导呕吐、类风湿关节炎、哮喘、克罗恩病、溃疡性结肠炎、皮炎、季节性过敏性鼻炎、胃食管反流病（GERD）、便秘、腹泻、功能性胃肠障碍、皮肤T细胞淋巴瘤、多发性硬化症、骨关节炎、牛皮癣、系统性红斑狼疮、糖尿病、青光眼、骨质疏松症、肾小球肾炎、肾缺血、肾炎、肝炎、脑中风、血管扩张、高血压、血管炎、心肌梗死、脑缺血、可逆气道阻塞、成人呼吸系统疾病综合征、慢性阻塞性肺疾病（COPD）、隐源性纤维化肺泡炎和支气管炎。
• Benzimidazolone derivatives as CB2 receptor ligands
  申请人：Pfizer Inc.

  公开号：US08138177B2

  公开（公告）日：2012-03-20

  This invention relates to compounds of the formula (I): or pharmaceutically acceptable salts thereof, wherein: A, B, R1, R2 and R3 are each as described herein, and compositions containing such compounds and the use of such compounds in the treatment of a condition mediated by CB2 receptor binding activity such as, but not limited to, inflammatory pain, nociceptive pain, neuropathic pain, fibromyalgia, chronic low back pain, visceral pain, acute cerebral ischemia, pain, chronic pain, acute pain, post herpetic neuralgia, neuropathies, neuralgia, diabetic neuropathy, HIV-related neuropathy, nerve injury, rheumatoid arthritic pain, osteoarthritic pain, back pain, cancer pain, dental pain, fibromyalgia, neuritis, sciatica, inflammation, neurodegenerative disease, cough, broncho constriction, irritable bowel syndrome (IBS), inflammatory bowel disease (IBD), colitis, cerebrovascular ischemia, emesis such as cancer chemotherapy-induced emesis, rheumatoid arthritis, asthma, Crohn's disease, ulcerative colitis, asthma, dermatitis, seasonal allergic rhinitis, gastroesophageal reflux disease (GERD), constipation, diarrhea, functional gastrointestinal disorder, cutaneous T cell lymphoma, multiple sclerosis, osteoarthritis, psoriasis, systemic lupus erythematosus, diabetes, glaucoma, osteoporosis, glomerulonephritis, renal ischemia, nephritis, hepatitis, cerebral stroke, vasculitis, myocardial infarction, cerebral ischemia, reversible airway obstruction, adult respiratory disease syndrome, chronic obstructive pulmonary disease (COPD), cryptogenic fibrosing alveolitis or bronchitis.

  本发明涉及以下式（I）的化合物或其药学上可接受的盐，其中：A、B、R1、R2和R3如下所述，并且包含这种化合物的组合物以及将这种化合物用于治疗由CB2受体结合活性介导的病症，例如但不限于炎性疼痛、伤害性疼痛、神经病性疼痛、纤维肌痛、慢性腰痛、内脏疼痛、急性脑缺血、疼痛、慢性疼痛、急性疼痛、带状疱疹后神经痛、神经病、神经痛、糖尿病神经病、艾滋病相关神经病、神经损伤、类风湿性关节炎疼痛、骨关节炎疼痛、背痛、癌痛、牙痛、纤维肌炎、神经炎、坐骨神经痛、炎症、神经退行性疾病、咳嗽、支气管收缩、肠易激综合征（IBS）、炎性肠病（IBD）、结肠炎、脑血管缺血、呕吐，如癌症化疗引起的呕吐，类风湿性关节炎、哮喘、克罗恩病、溃疡性结肠炎、哮喘、皮炎、季节性过敏性鼻炎、胃食管反流病（GERD）、便秘、腹泻、功能性胃肠障碍、皮肤T细胞淋巴瘤、多发性硬化症、骨关节炎、牛皮癣、系统性红斑狼疮、糖尿病、青光眼、骨质疏松症、肾小球肾炎、肾缺血、肾炎、肝炎、脑卒中、血管炎、心肌梗塞、脑缺血、可逆气道阻塞、成人呼吸系统疾病综合征、慢性阻塞性肺疾病（COPD）、隐源性纤维化性肺炎或支气管炎。
• BENZIMIDAZOLONE DERIVATIVES AS CB2 RECEPTOR LIGANDS
  申请人：Ando Kazuo

  公开号：US20090181957A1

  公开（公告）日：2009-07-16

  This invention relates to compounds of the formula (I): or pharmaceutically acceptable salts thereof, wherein: A, B, R 1 , R 2 and R 3 are each as described herein, and compositions containing such compounds and the use of such compounds in the treatment of a condition mediated by CB2 receptor binding activity such as, but not limited to, inflammatory pain, nociceptive pain, neuropathic pain, fibromyalgia, chronic low back pain, visceral pain, acute cerebral ischemia, pain, chronic pain, acute pain, post herpetic neuralgia, neuropathies, neuralgia, diabetic neuropathy, HIV-related neuropathy, nerve injury, rheumatoid arthritic pain, osteoarthritic pain, back pain, cancer pain, dental pain, fibromyalgia, neuritis, sciatica, inflammation, neurodegenerative disease, cough, broncho constriction, irritable bowel syndrome (IBS), inflammatory bowel disease (IBD), colitis, cerebrovascular ischemia, emesis such as cancer chemotherapy-induced emesis, rheumatoid arthritis, asthma, Crohn's disease, ulcerative colitis, asthma, dermatitis, seasonal allergic rhinitis, gastroesophageal reflux disease (GERD), constipation, diarrhea, functional gastrointestinal disorder, cutaneous T cell lymphoma, multiple sclerosis, osteoarthritis, psoriasis, systemic lupus erythematosus, diabetes, glaucoma, osteoporosis, glomerulonephritis, renal ischemia, nephritis, hepatitis, cerebral stroke, vasculitis, myocardial infarction, cerebral ischemia, reversible airway obstruction, adult respiratory disease syndrome, chronic obstructive pulmonary disease (COPD), cryptogenic fibrosing alveolitis or bronchitis.

  本发明涉及式(I)的化合物或其药学上可接受的盐，其中：A、B、R1、R2和R3如此处所述，并且包含这种化合物的组合物以及在治疗由CB2受体结合活性介导的疾病中使用这种化合物，例如，但不限于炎症性疼痛、伤害性疼痛、神经病理性疼痛、纤维肌痛、慢性腰痛、内脏疼痛、急性脑缺血、疼痛、慢性疼痛、急性疼痛、带状疱疹后神经痛、神经病、神经痛、糖尿病神经病、艾滋病相关神经病、神经损伤、类风湿性关节炎疼痛、骨关节炎疼痛、背痛、癌症疼痛、牙痛、纤维肌痛、神经炎、坐骨神经痛、炎症、神经退行性疾病、咳嗽、支气管收缩、肠易激综合症（IBS）、炎症性肠病（IBD）、结肠炎、脑血管缺血、恶心（如癌症化疗引起的恶心）、类风湿性关节炎、哮喘、克罗恩病、溃疡性结肠炎、哮喘、皮炎、季节性过敏性鼻炎、胃食管反流病（GERD）、便秘、腹泻、功能性胃肠障碍、皮肤T细胞淋巴瘤、多发性硬化症、骨关节炎、银屑病、系统性红斑狼疮、糖尿病、青光眼、骨质疏松症、肾小球肾炎、肾缺血、肾炎、肝炎、脑卒中、血管炎、心肌梗塞、脑缺血、可逆气道阻塞、成人呼吸系统疾病综合症、慢性阻塞性肺疾病（COPD）、隐源性纤维化性肺炎或支气管炎。
• US8138177B2
  申请人：——

  公开号：US8138177B2

  公开（公告）日：2012-03-20
• [EN] BENZIMIDAZOLONE DERIVATIVES AS CB2 RECEPTOR LIGANDS<br/>[FR] DERIVES DE BENZIMIDAZOLONE EN TANT QUE LIGANDS DE RECEPTEUR CB2
  申请人：PFIZER JAPAN INC

  公开号：WO2006097808A1

  公开（公告）日：2006-09-21

  [EN] This invention relates to compounds of the formula (I): or pharmaceutically acceptable salts thereof, wherein: A, B, R¹, R² and R³ are each as described herein, and compositions containing such compounds and the use of such compounds in the treatment of a condition mediated by CB2 receptor binding activity such as, but not limited to, inflammatory pain, nociceptive pain, neuropathic pain, fibromyalgia, chronic low back pain, visceral pain, acute cerebral ischemia, pain, chronic pain, acute pain, post herpetic neuralgia, neuropathies, neuralgia, diabetic neuropathy, HIV-related neuropathy, nerve injury, rheumatoid arthritic pain, osteoarthritic pain, back pain, cancer pain, dental pain, fibromyalgia, neuritis, sciatica, inflammation, neurodegenerative disease, cough, broncho constriction, irritable bowel syndrome (IBS), inflammatory bowel disease (IBD), colitis, cerebrovascular ischemia, emesis such as cancer chemotherapy-induced emesis, rheumatoid arthritis, asthma, Crohn's disease, ulcerative colitis, asthma, dermatitis, seasonal allergic rhinitis, gastroesophageal reflux disease (GERD), constipation, diarrhea, functional gastrointestinal disorder, cutaneous T cell lymphoma, multiple sclerosis, osteoarthritis, psoriasis, systemic lupus erythematosus, diabetes, glaucoma, osteoporosis, glomerulonephritis, renal ischemia, nephritis, hepatitis, cerebral stroke, vasculitis, myocardial infarction, cerebral ischemia, reversible airway obstruction, adult respiratory disease syndrome, chronic obstructive pulmonary disease (COPD), cryptogenic fibrosing alveolitis or bronchitis.
  [FR] La présente invention a trait à des composés de formule (I), dans laquelle: A, B, R¹, R² et R³ sont tels que définis dans la description, ou leurs sels pharmaceutiquement acceptables; et à des compositions contenant de tels composés et à l'utilisation de tels composé dans le traitement d'une condition médiée par une activité de liaison au récepteur CB2 telle que, mais de manière non limitative, la douleur inflammatoire, la douleur nociceptive, la douleur névropathique, la fibromyalgie, la lombalgie chronique, la douleur viscérale, la douleur ischémique cérébrale aiguë, la douleur chronique, la douleur aiguë, la névralgie post-herpétique, les névropathies, la névralgie, la névropathie diabétique, la névropathie liée au VIH, la lésion nerveuse, la douleur arthritique rhumatoïde, la douleur ostéoarthritique, la dorsalgie, la douleur cancéreuse, la douleur dentaire, la fibromyalgie, la névrite, la sciatique, l'inflammation, la maladie neurodégénérative, la toux, la constriction bronchique, le syndrome du côlon irritable, la maladie intestinale inflammatoire, la colite, l'ischémie cerébro-vasculaire, le vomissement tel que le vomissement induit par la chimiothérapie du cancer, la polyarthrite rhumatoïde, l'asthme, la maladie de Crohn, la colite ulcéreuse, l'asthme, la dermatite, la rhinite allergique saisonnière, la maladie du reflux gastro-oesophagien, la constipation, la diarrhée, le trouble gastro-intestinal fonctionnel, le lymphome T cutané, la sclérose en plaques, l'ostéoarthrite, le psoriasis, le lupus érythémateux systémique, le diabète, le glaucome, l'ostéoporose, la glomérulonéphrite, l'ischémie rénale, la néphrite, l'hépatite, l'apoplexie, la vasculite, l'infarctus du myocarde, l'ischémie cérébrale, l'obstruction de voies aériennes réversible, le syndrome de la maladie respiratoire adulte, la broncho-pneumopathie chronique obstructive (BPCO), l'alvéolite fibrosante cryptogénétique ou la bronchite.