5-溴-3-(1-甲基-1,2,3,6-四氢吡啶-4-基)-1H-吲哚 | 116480-53-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5-溴-3-(1-甲基-1,2,3,6-四氢吡啶-4-基)-1H-吲哚
• 英文名称: 5-bromo-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole
• 英文别名: 5-bromo-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)indole；5-Bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole；5-bromo-3-(1,2,3,6-tetrahydro-1-methyl4-pyridinyl)-1H-indole；5-bromo-3-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-1H-indole
• CAS: 116480-53-6
• 化学式: C₁₄H₁₅BrN₂
• 分子量: 291.19
• InChiKey: IRJNNZSKGXPISD-UHFFFAOYSA-N

物化性质

• 熔点：
  266-268℃

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-溴-3-(1-甲基-1,2,3,6-四氢吡啶-4-基)-1H-吲哚 在 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 、 正戊烷 为溶剂， 生成 5-(Indol-3-yl)-3-(1-Methylpiperidin-4-yl)-1H-Indole
  参考文献：
  名称：

  5-HT1F agonists

  摘要：

  本发明涉及以下化合物（I）的化合物或其药用酸盐；该化合物对于激活哺乳动物体内的5-HT1f受体和抑制蛋白外渗具有用处。

  公开号：

  US06358972B1
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 5-溴吲哚 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以95%的产率得到5-溴-3-(1-甲基-1,2,3,6-四氢吡啶-4-基)-1H-吲哚
  参考文献：
  名称：

  合成5-溴-3-（1-甲基哌啶-4-基）-1 H-吲哚的改进方法：纳拉曲坦盐酸盐合成中的关键中间体

  摘要：

  已经开发出一种改进的方法，用于合成5-溴-3-（1-甲基哌啶-4-基）-1 H-吲哚，其是盐酸那拉曲普坦的关键中间体，被用作偏头痛药物。为扩大规模，开发了一种使用三乙基硅烷的新型一锅法合成程序。

  DOI：

  10.1021/op100018r

文献信息

• Piperidine-indole compounds having 5-HT.sub.6 affinity
  申请人：Allelix Biopharmaceuticals Inc.

  公开号：US06133287A1

  公开（公告）日：2000-10-17

  Described herein are compounds with affinity for the 5-HT.sub.6 receptor, which have the general formula: wherein: R.sup.1 is selected from the group consisting of H and C.sub.1-4 alkyl; R.sup.2 is selected from the group consisting of H, C.sub.1-4 alkyl and benzyl; -- -- -- represents a single or double bond; R.sup.3 is selected from the group consisting of COR.sup.5 and SO.sub.2 R.sup.5 ; R.sup.4a is selected from the group consisting of H, OH, halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; R.sup.4b is selected from the group consisting of H, hydroxy, halo, C.sub.3-7 cycloalkyloxy, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, benzyloxy, phenoxy, trifluoromethyl, trifluoromethoxy and vinyl; R.sup.4c is selected from the group consisting of H, OH, halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; R.sub.4d is selected from the group consisting of H, OH, halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; and R.sup.5 is selected from the group consisting of phenyl, pyridyl, thienyl, quinolinyl and naphthyl which are optionally substituted with 1-4 substituents selected from C.sub.1-4 alkoxy, C.sub.1-4 alkyl, halo, nitro, trifluoromethyl, trifluoromethoxy, 1,2-methylenedioxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl and C.sub.1-4 alkylS--. Also described is the use of these compounds as pharmaceuticals to treat indications where inhibition of the 5-HT.sub.6 receptor is implicated, such as schizophrenia.

  本文描述了与5-HT.sub.6受体亲和力的化合物，其具有以下一般公式：其中：R.sup.1选自H和C.sub.1-4烷基组; R.sup.2选自H、C.sub.1-4烷基和苄基组; -- -- --代表单键或双键; R.sup.3选自COR.sup.5和SO.sub.2R.sup.5组; R.sup.4a选自H、OH、卤素、C.sub.1-4烷基和C.sub.1-4烷氧基组; R.sup.4b选自H、羟基、卤素、C.sub.3-7环烷氧基、C.sub.1-4烷氧基、C.sub.1-4烷基、苄氧基、苯氧基、三氟甲基、三氟甲氧基和乙烯基组; R.sup.4c选自H、OH、卤素、C.sub.1-4烷基和C.sub.1-4烷氧基组; R.sub.4d选自H、OH、卤素、C.sub.1-4烷基和C.sub.1-4烷氧基组; R.sup.5选自苯基、吡啶基、噻吩基、喹啉基和萘基，可选择地用1-4个来自C.sub.1-4烷氧基、C.sub.1-4烷基、卤素、硝基、三氟甲基、三氟甲氧基、1,2-亚甲二氧基、C.sub.1-4烷基羰基、C.sub.1-4烷氧羰基和C.sub.1-4烷基硫代基的取代基取代。还描述了将这些化合物用作药物治疗5-HT.sub.6受体受抑制相关的适应症，如精神分裂症。
• Novel Compounds for the Treatment of Diseases Associated with Amyloid or Amyloid-Like Proteins
  申请人：Kroth Heiko

  公开号：US20110280808A1

  公开（公告）日：2011-11-17

  The present invention relates to novel compounds that can be employed in the treatment of a group of disorders and abnormalities associated with amyloid protein, such as Alzheimer's disease, and of diseases or conditions associated with amyloid-like proteins. The compounds of the present invention can also be used in the treatment of ocular diseases associated with pathological abnormalities/changes in the tissues of the visual system. The present invention further relates to pharmaceutical compositions comprising these compounds and to the use of these compounds for the preparation of medicaments for treating or preventing diseases or conditions associated with amyloid and/or amyloid-like proteins. A method of treating or preventing diseases or conditions associated with amyloid and/or amyloid-like proteins is also disclosed.

  本发明涉及一种新型化合物，可用于治疗与淀粉样蛋白相关的一组疾病和异常，如阿尔茨海默病，以及与淀粉样蛋白类似蛋白相关的疾病或病况。本发明的化合物还可用于治疗与视觉系统组织中的病理异常/变化相关的眼部疾病。本发明还涉及包含这些化合物的药物组合物，以及利用这些化合物制备用于治疗或预防与淀粉样和/或淀粉样类似蛋白相关的疾病或病况的药物的用途。还公开了一种治疗或预防与淀粉样和/或淀粉样类似蛋白相关的疾病或病况的方法。
• [EN] NOVEL COMPOUNDS FOR THE TREATMENT OF DISEASES ASSOCIATED WITH AMYLOID OR AMYLOID-LIKE PROTEINS<br/>[FR] NOUVEAUX COMPOSÉS POUR LE TRAITEMENT DE MALADIES ASSOCIÉES AUX PROTÉINES AMYLOÏDES OU DE TYPE AMYLOÏDE
  申请人：AC IMMUNE SA

  公开号：WO2011128455A1

  公开（公告）日：2011-10-20

  The present invention relates to novel compounds that can be employed in the treatment of a group of disorders and abnormalities associated with amyloid protein, such as Alzheimer's disease, and of diseases or conditions associated with amyloid-like proteins. The compounds of the present invention can also be used in the treatment of ocular diseases associated with pathological abnormalities/changes in the tissues of the visual system. The present invention further relates to pharmaceutical compositions comprising these compounds and to the use of these compounds for the preparation of medicaments for treating or preventing diseases or conditions associated with amyloid and/or amyloid-like proteins. A method of treating or preventing diseases or conditions associated with amyloid and/or amyloid-like proteins is also disclosed.

  本发明涉及一类新化合物，可用于治疗与淀粉样蛋白相关的一组疾病和异常，例如阿尔茨海默病，以及与类淀粉样蛋白相关的疾病或状况。本发明的化合物还可用于治疗与视觉系统组织病理性异常/变化相关的眼病。本发明还涉及包含这些化合物的药物组合物，以及使用这些化合物制备用于治疗或预防与淀粉样和/或类淀粉样蛋白相关的疾病或状况的药物。还公开了一种治疗或预防与淀粉样和/或类淀粉样蛋白相关疾病或状况的方法。
• Inhibition of serotonin reuptake
  申请人：Eli Lilly and Company

  公开号：US05846982A1

  公开（公告）日：1998-12-08

  This invention provides compounds and a method for the inhibition of serotonin reuptake in mammals.

  这项发明提供了一种用于抑制哺乳动物中5-羟色胺再摄取的化合物和方法。
• 1H-indole and benzo(b)thiophene derivatives with 4-(1,2,3,6-tetra:hydro:pyridinyl)- and 4-piperidinyl-groups bound to the heterocyclic ring as inhibitors of serotonin reuptake
  申请人：ELI LILLY AND COMPANY

  公开号：EP0812826A1

  公开（公告）日：1997-12-17

  The pharmaceutical use of novel compounds of formula I: where Z is a structure of formula A-B is -C=CH- or -C(R5)-CH2-; X is S or NR4; R1 is H, halo, formyl, C1-C4 alkyl, C1-C4 alkoxy, thienylmethyloxy, 4,5-dihydrothiazol-2-yl, cyano, nitro, carboxamido, trifluoromethyl or hydroxy; R2 is H or halo; R3 is H, C1-C4 alkyl, (C1-C4 alkylene)-aryl, or -CH2-Y-NR7R8; R4 is H, C1-C4 alkyl, C1-C5 acyl, or phenylsulfonyl; R5 is H or OH; R6 is H or methyl; Y is -CH2- or -C(O)-; R7 is pyridinyl; and R8 is H or -C(O)-(C3-C6 cycloalkyl); and pharmaceutically acceptable salts thereof.

  化合物的药用途：其中Z是formulaA-B结构，-C=CH-或-C(R5)-CH2-；X是S或NR4；R1是H、卤素、甲酰基、C1-C4烷基、C1-C4烷氧基、噻吩甲氧基、4,5-二氢噻唑-2-基、氰基、硝基、羧酰胺基、三氟甲基或羟基；R2是H或卤素；R3是H、C1-C4烷基、(C1-C4烷基)-芳基，或-CH2-Y-NR7R8；R4是H、C1-C4烷基、C1-C5酰基，或苯基磺酰基；R5是H或OH；R6是H或甲基；Y是-CH2-或-C(O)-；R7是吡啶基；R8是H或-C(O)-(C3-C6环烷基)；以及其药用上可接受的盐。