8-[3-(5-chloro-thiophen-2-yl)-phenyl]-6-(1-methanesulfonyl-1-methyl-ethyl)-quinoline | 638218-69-6

• 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: 8-[3-(5-chloro-thiophen-2-yl)-phenyl]-6-(1-methanesulfonyl-1-methyl-ethyl)-quinoline
• 英文别名: 8-[3-(5-Chlorothiophen-2-yl)phenyl]-6-(2-methylsulfonylpropan-2-yl)quinoline
• CAS: 638218-69-6
• 化学式: C₂₃H₂₀ClNO₂S₂
• 分子量: 442.002
• InChiKey: QBZNJVMHQKFVGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴-5-氯噻吩 、 6-(1-methanesulfonyl-1-methyl-ethyl)-8-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-quinoline 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 12.0h， 生成 8-[3-(5-chloro-thiophen-2-yl)-phenyl]-6-(1-methanesulfonyl-1-methyl-ethyl)-quinoline
  参考文献：
  名称：

  [EN] 8-(BIARYL) QUINOLINE PDE4 INHIBITORS
  [FR] INHIBITEURS DE PDE4 8-(BIARYLE)QUINOLINES

  摘要：

  8-(联苯基)喹啉类化合物，其中在8位的联苯基与喹啉基团呈间位关系，是磷酸二酯酶4抑制剂，在治疗哮喘、慢性支气管炎、慢性阻塞性肺疾病、嗜酸性肉芽肿、牛皮癣和其他良性或恶性增生性皮肤疾病、内毒素休克、马蹄炎、马胃肠炎、脓毒性休克、溃疡性结肠炎、克罗恩病、心肌和脑再灌注损伤、炎症性关节炎、慢性肾小球肾炎、特应性皮炎、荨麻疹、成人呼吸窘迫综合征、动物慢性阻塞性肺疾病、尿崩症、过敏性鼻炎、过敏性结膜炎、春季结膜炎、动脉再狭窄、动脉粥样硬化、动脉粥样硬化、神经源性炎症、疼痛、咳嗽、类风湿性关节炎、强直性脊柱炎、移植排斥反应、移植物抗宿主病、胃酸过多分泌、细菌、真菌诱导的败血症、病毒诱导的败血症、真菌诱导的脓毒性休克、病毒诱导的脓毒性休克、炎症介导的慢性组织退行性变、细胞因子介导的慢性组织退行性变、骨关节炎、癌症、虚弱、肌肉消耗、抑郁症、记忆障碍、肿瘤生长或癌细胞侵袭正常组织。另一方面，本发明涉及一种增强健康受试者认知能力的方法，包括给予安全的增强认知量的磷酸二酯酶4抑制剂。具体而言，本发明涉及一种增强健康受试者记忆、学习、保留、回忆、意识和判断能力的方法，包括给予安全且增强认知量的磷酸二酯酶4抑制剂。

  公开号：

  WO2004000814A1

文献信息

• 8-(Biaryl)quinoline pde4 inhibitors
  申请人：Dube Daniel

  公开号：US20050234238A1

  公开（公告）日：2005-10-20

  8-(biaryl) quinolines wherein the bi-aryl group at the 8-position is in a meta relationship to the quinoline group, are PDE4 inhibitors useful in the treatment of asthma, chronic bronchitis, chronic obstructive pulmonary disease, eosinophilic granuloma, psoriasis and other benign or malignant proliferative skin diseases, endotoxic shock, laminitis in horses, colic in horses, septic shock, ulcerative colitis, Crohn's disease, reperfusion injury of the myocardium and brain, inflammatory arthritis, chronic glomerulonephritis, atopic dermatitis, urticaria, adult respiratory distress syndrome, chronic obstructive pulmonary disease in animals, diabetes insipidus, allergic rhinitis, allergic conjunctivitis, vernal conjunctivitis, arterial restenosis, ortherosclerosis, atherosclerosis, neurogenic inflammation, pain, cough, rheumatoid arthritis, ankylosing spondylitis, transplant rejection, graft versus host disease, hypersecretion of gastric acid, bacterial, fungal induced sepsis, viral induced sepsis, fungal induced septic shock, viral induced septic shock, inflammation-mediated chronic tissue degeneration, cytokine-mediated chronic tissue degeneration, osteoarthritis, cancer, cachexia, muscle wasting, depression, memory impairment, tumour growth, or cancerous invasion of normal tissues. In another aspect, the present invention is directed to a method of enhancing cognition in a healthy subject comprising administering a safe cognition enhancing amount of phosphodiesterase-4 inhibitor. In particular, this invention is directed to a method of enhancing memory, learning, retention, recall, awareness and judgement in health subjects comprising administering a safe and cognition enhancing amount of a phosphodiesterase-4 inhibitor.

  8-(联苯基)喹啉中，8位位置的联苯基与喹啉基团呈间位关系，是PDE4抑制剂，可用于治疗哮喘、慢性支气管炎、慢性阻塞性肺疾病、嗜酸性粒细胞肉芽肿、银屑病和其他良性或恶性增生性皮肤疾病、内毒素休克、马蹄疾病、马腹绞痛、败血症休克、溃疡性结肠炎、克罗恩病、心肌和脑再灌注损伤、炎性关节炎、慢性肾小球肾炎、特应性皮炎、荨麻疹、成人呼吸窘迫综合症、动物慢性阻塞性肺疾病、尿崩症、过敏性鼻炎、过敏性结膜炎、春季结膜炎、动脉再狭窄、动脉硬化、神经源性炎症、疼痛、咳嗽、类风湿性关节炎、强直性脊柱炎、移植排斥、移植物抗宿主病、胃酸分泌过多、细菌、真菌引起的败血症、病毒引起的败血症、真菌引起的败血性休克、病毒引起的败血性休克、炎症介导的慢性组织退化、细胞因子介导的慢性组织退化、骨关节炎、癌症、消瘦、肌肉消耗、抑郁症、记忆障碍、肿瘤生长或癌细胞侵袭正常组织。另一方面，本发明还涉及一种增强健康受试者认知能力的方法，包括给予安全的认知增强剂量的磷酸二酯酶-4抑制剂。特别地，本发明涉及一种增强健康受试者记忆、学习、保留、回忆、意识和判断能力的方法，包括给予安全的认知增强剂量的磷酸二酯酶-4抑制剂。
• 8-(BIARYL) QUINOLINE PDE4 INHIBITORS
  申请人：MERCK FROSST CANADA INC.

  公开号：EP1517895A1

  公开（公告）日：2005-03-30
• US7153968B2
  申请人：——

  公开号：US7153968B2

  公开（公告）日：2006-12-26
• [EN] 8-(BIARYL) QUINOLINE PDE4 INHIBITORS<br/>[FR] INHIBITEURS DE PDE4 8-(BIARYLE)QUINOLINES
  申请人：MERCK FROSST CANADA INC

  公开号：WO2004000814A1

  公开（公告）日：2003-12-31

  8-(biaryl) quinolines wherein the bi-aryl group at the 8-position is in a meta relationship to the quinoline group, are PDE4 inhibitors useful in the treatment of asthma, chronic bronchitis, chronic obstructive pulmonary disease, eosinophilic granuloma, psoriasis and other benign or malignant proliferative skin diseases, endotoxic shock, laminitis in horses, colic in horses, septic shock, ulcerative colitis, Crohn's disease, reperfusion injury of the myocardium and brain, inflammatory arthritis, chronic glomerulonephritis, atopic dermatitis, urticaria, adult respiratory distress syndrome, chronic obstructive pulmonary disease in animals, diabetes insipidus, allergic rhinitis, allergic conjunctivitis, vernal conjunctivitis, arterial restenosis, ortherosclerosis, atherosclerosis, neurogenic inflammation, pain, cough, rheumatoid arthritis, ankylosing spondylitis, transplant rejection, graft versus host disease, hypersecretion of gastric acid, bacterial, fungal induced sepsis, viral induced sepsis, fungal induced septic shock, viral induced septic shock, inflammation-mediated chronic tissue degeneration, cytokine-mediated chronic tissue degeneration, osteoarthritis, cancer, cachexia, muscle wasting, depression, memory impairment, tumour growth, or cancerous invasion of normal tissues.In another aspect, the present invention is directed to a method of enhancing cognition in a healthy subject comprising administering a safe cognition enhancing amount of phosphodiesterase-4 inhibitor. In particular, this invention is directed to a method of enhancing memory, learning, retention, recall, awareness and judgement in health subjects comprising administering a safe and cognition enhancing amount of a phosphodiesterase-4 inhibitor.

  8-(联苯基)喹啉类化合物，其中在8位的联苯基与喹啉基团呈间位关系，是磷酸二酯酶4抑制剂，在治疗哮喘、慢性支气管炎、慢性阻塞性肺疾病、嗜酸性肉芽肿、牛皮癣和其他良性或恶性增生性皮肤疾病、内毒素休克、马蹄炎、马胃肠炎、脓毒性休克、溃疡性结肠炎、克罗恩病、心肌和脑再灌注损伤、炎症性关节炎、慢性肾小球肾炎、特应性皮炎、荨麻疹、成人呼吸窘迫综合征、动物慢性阻塞性肺疾病、尿崩症、过敏性鼻炎、过敏性结膜炎、春季结膜炎、动脉再狭窄、动脉粥样硬化、动脉粥样硬化、神经源性炎症、疼痛、咳嗽、类风湿性关节炎、强直性脊柱炎、移植排斥反应、移植物抗宿主病、胃酸过多分泌、细菌、真菌诱导的败血症、病毒诱导的败血症、真菌诱导的脓毒性休克、病毒诱导的脓毒性休克、炎症介导的慢性组织退行性变、细胞因子介导的慢性组织退行性变、骨关节炎、癌症、虚弱、肌肉消耗、抑郁症、记忆障碍、肿瘤生长或癌细胞侵袭正常组织。另一方面，本发明涉及一种增强健康受试者认知能力的方法，包括给予安全的增强认知量的磷酸二酯酶4抑制剂。具体而言，本发明涉及一种增强健康受试者记忆、学习、保留、回忆、意识和判断能力的方法，包括给予安全且增强认知量的磷酸二酯酶4抑制剂。