1-benzyl-4-[N-(4-fluorophenyl)amino]piperidine | 131587-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-benzyl-4-[N-(4-fluorophenyl)amino]piperidine
• 英文别名: N-Benzyl-4-(4-fluoroanilino)piperidine；(1-benzylpiperidine-4-yl)-(4-fluorophenyl)amine；N-(1-benzyl-4-piperidinyl)-N-(4-fluorophenyl)amine；1-benzyl-N-(4-fluorophenyl)piperidin-4-amine
• CAS: 131587-27-4
• 化学式: C₁₈H₂₁FN₂
• 分子量: 284.377
• InChiKey: GCHCRHBAGFHFMV-UHFFFAOYSA-N

物化性质

• 沸点：
  404.4±45.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：25 mg/ml； DMSO：50 mg/ml；乙醇：100 mg/ml；乙醇:PBS (pH 7.2) (1:3): 0.25 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-[N-(4-fluorophenyl)amino]piperidine 在 甲醇 、 1-氯乙基氯甲酸酯 作用下， 以 甲苯 为溶剂， 生成 N-(4-fluorophenyl)-N-(piperidin-4-yl)propionamide
  参考文献：
  名称：

  Pharmacological profile of a novel series of NK1 antagonists. In vitro and in vivo potency of benzimidazolone derivatives

  摘要：

  By low throughput examination of our chemical library, compound 7 was selected as a lead NK, antagonist with a K-i of 7.1 nM. Modifications of its structure led to the finding that the in vitro potency could be markedly enhanced by disubstituting the anilino phenyl ring as in compounds 13 or 22. Human binding data correlated rather well with results obtained with in vitro animal mice; compound 13 was the most active with ED50 of 0.001 and 0.3 mg/kg after iv and po administration respectively. Furthermore, antagonist 71 was found to be a potent inhibitor of SP-induced bronchoconstriction in guinea-pigs with an ED50 between 0.1 and 0.03 mg/kg iv. Furthermore, upon oral administration, 71 was observed to be active in a model of SP-induced bronchial hypersensitivity in mice, with an ID50 of around 3 mg/kg.

  DOI：

  10.1016/s0223-5234(97)82771-7
• 作为产物：
  描述：

  1-苄基-2-哌啶酮 在 Å molecular sieve 、 氯化锌 、 4-氟苯胺 sodium cyanoborohydride 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 生成 1-benzyl-4-[N-(4-fluorophenyl)amino]piperidine
  参考文献：
  名称：

  Benzopyran derivatives, their preparation and pharmaceutical

  摘要：

  通用公式（I）的新苯并吡喃衍生物，其中：R.sub.1代表氢或卤素原子或羟基、烷氧基、硝基、氨基、烷基磺酰胺基或酰胺基基团，R代表（1）基团：R.sub.2和R.sub.3可以相同也可以不同，分别为H、卤素、OH、烷基、烷氧基、NH.sub.2、烷基磺酰胺基或NO.sub.2，或（2）基团：n为0或1，R.sub.4为H、烷基或可选择性取代的苯基，Q为酰基、烷基磺酰基或Y为--CO--或--SO.sub.2--，Z为单键、--CH.sub.2--或--NH--，或（3）基团：n为0或1，m为0或2，X为C或N（如果n=0），W为键或--NH--，AR为吡啶基、吲哚基、喹啉基、2-烷基喹啉基或苯基，可选择性取代R.sub.2和R.sub.3，但当X等于N时，n=0，或（4）基团的一般公式：R.sub.7为H或烷基，或者（5）基团：R'和R"相同，分别代表氢原子或烷基基团，它们的异构形式和混合物，以及其与酸的加合盐。这些新产品可用作抗心律失常和抗纤颤剂。

  公开号：

  US05025013A1

文献信息

• [EN] INDOLE DERIVATIVES USEFUL AS HISTAMINE H3 ANTAGONISTS<br/>[FR] DERIVES D'INDOLE UTILISES EN TANT QU'ANTAGONISTES H3 D'HISTAMINE
  申请人：SCHERING CORP

  公开号：WO2004000831A1

  公开（公告）日：2003-12-31

  Disclosed are novel compounds of the formula I wherein M1 is CH or N and M2 is C(R3) or N; R1 is optionally substituted indolyl or an aza derivative thereof; R2 is optionally substituted aryl or heteroaryl; and the remaining variables are as defined in the specification. Also disclosed are pharmaceutical compositions comprising the compounds of formula I. Also disclosed are methods of treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion) using the compounds of Formula I. Also disclosed are methods of treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion) using the compounds of formula I in combination with a H1 receptor antagonist.

  揭示了式I的新化合物，其中M1为CH或N，M2为C(R3)或N；R1为可选择地取代的吲哚基或其氮杂衍生物；R2为可选择地取代的芳基或杂环芳基；其余变量如规范中所定义。还揭示了包括式I化合物的药物组合物。还揭示了使用式I化合物治疗各种疾病或症状的方法，例如过敏、过敏引起的气道反应和充血（例如，鼻塞）等。还揭示了使用式I化合物与H1受体拮抗剂结合治疗各种疾病或症状的方法，例如过敏、过敏引起的气道反应和充血（例如，鼻塞）等。
• Novel piperidine-substituted indoles-or heteroderivatives thereof
  申请人：Anderskewitz Ralf

  公开号：US20050153979A1

  公开（公告）日：2005-07-14

  Accordingly, one object of the present invention are novel piperidine-substituted indoles- or heteroderivatives thereof of the formula 1: wherein R 1 , R 5 , R 6 , A, B, D-E, X—W—V, Y, i, j, n and m are defined as below. Another object of the present invention is to provide agonists or antagonists of CCR-3, or pharmaceutically acceptable salts thereof, more particularly to provide pharmaceutical compositions comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of at least one of the compounds of the present invention or a pharmaceutically acceptable salt thereof.

  因此，本发明的一个目标是提供一种新型的哌啶取代的吲哚或其杂环衍生物，其化学式为1：其中R1，R5，R6，A，B，D-E，X—W—V，Y，i，j，n和m如下所定义。本发明的另一个目标是提供CCR-3的激动剂或拮抗剂，或其药学上可接受的盐，更具体地提供包含药学上可接受的载体和本发明化合物或其药学上可接受的盐的治疗有效量的制剂。
• Piperidine-substituted indoles-or heteroderivatives thereof
  申请人：Boehringer Ingelheim International GmbH

  公开号：US07544806B2

  公开（公告）日：2009-06-09

  Accordingly, one object of the present invention are novel piperidine-substituted indoles- or heteroderivatives thereof of the formula 1: wherein R1, R5, R6, A, B, D-E, X-W-V, Y, i, j, n and m are defined as below. Another object of the present invention is to provide agonists or antagonists of CCR-3, or pharmaceutically acceptable salts thereof, more particularly to provide pharmaceutical compositions comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of at least one of the compounds of the present invention or a pharmaceutically acceptable salt thereof.

  因此，本发明的一个目的是提供式1中的新型哌啶取代吲哚或其杂环衍生物，其中R1、R5、R6、A、B、D-E、X-W-V、Y、i、j、n和m的定义如下。本发明的另一个目的是提供CCR-3的激动剂或拮抗剂，或其药学上可接受的盐，更具体地提供包含药学上可接受的载体和本发明化合物或其药学上可接受的盐的至少一种的治疗有效量的制剂。
• N-Aryl-N-(4-Piperidinyl)amides and pharmaceutical compositions and methods employing such compounds
  申请人：Anaquest, Inc.

  公开号：EP0160422A1

  公开（公告）日：1985-11-06

  Compounds are disclosed of the formula optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is selected from the group consisting of phenyl and substituted phenyl wherein the substituents are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio, or combinations thereof: R1 is selected from a furanyl group, a thienyl group or a group of the formula wherein R5 is selected from lower-alkyl, lower-cycloalkyl, halogenated lower-alkyl, phenyl, or phenyl lower-alkyl, and wherein each R6 is independently selected from hydrogen, lower-cycloalkyl or lower-alkyl; P2 is selected from the group consisting of phenyl-lower-alkyl, lower-alkyl, lower-alkenyl, lower-alkynyl, halogenated lower-alkyl, (cycloalkyl)alkyl, thienyl lower-alkyl,thiazolyl lower-alkyl which can be substituted in the 4-position with a methyl group, (4,5-dihydro-5-oxo-1H-tetrazol-1-yl) lower-alkyl which can be substituted in the 4-position with a group selected from lower-alkyl, lower cycloalkyl, aryl or aryl lower-alkyl, and substituted phenyl lower-alkyl in whcih the substituents on the phenyl ring are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio or combinations thereof; R3 is selected from a ! group consisting of hydrogen, methoxymethyl, and a carboxylate radical represented by the formula. wherein R10 is selected from the group consisting of lower-alkyl, aryl-lower-alkyl, lower-alkoxy-lower-alkyl, and aryloxy-lower-alkyl; and R4 is selected from hydrogen or methyl. Analgesic compositions containing these compounds and methods of using such compounds are also disclosed.

  所公开的化合物为式 其光学活性异构体形式，和/或其药学上可接受的酸加成盐，式中R 选自苯基和取代苯基组成的组，其中取代基选自卤素、氰基、低级烷氧基、低级烷基、低级烷二氧基、卤代低级烷基、低级烷硫基或其组合：R1 选自呋喃基、噻吩基或式如下的基团 其中 R5 选自低烷基、低环烷基、卤代低烷基、苯基或苯基低烷基，且每个 R6 独立选自氢、低环烷基或低烷基；P2 选自由苯基-低级烷基、低级烷基、低级烯基、低级炔基、卤代低级烷基、 （环烷基）烷基、噻吩低级烷基、可在 4 位被甲基取代的噻唑低级烷基、可在 4 位被选 自低级烷基的基团取代的（4,5-二氢-5-氧代-1H-四唑-1-基）低级烷基、低级环烷基、芳基或芳基低级烷基和取代的苯基低级烷基，其中苯环上的取代基 选自卤素、氰基、低级烷氧基、低级烷基、低级烷二氧基、卤代低级烷基、低级烷硫基 或它们的组合；R3 选自！其中 R10 选自由低级烷基、芳基-低级烷基、低级烷氧基-低级烷基和芳氧基-低级烷基组成的组；R4 选自由氢或甲基。还公开了含有这些化合物的镇痛组合物和使用这些化合物的方法。
• Indole derivatives useful as histamine H3 antagonists
  申请人：SCHERING CORPORATION

  公开号：EP1777223A1

  公开（公告）日：2007-04-25

  Disclosed are novel compounds of the formula I wherein M1 is CH or N and M2 is C(R3) or N; R1 is optionally substituted indolyl or an aza derivative thereof; R2 is optionally substituted aryl or heteroaryl; and the remaining variables are as defined in the specification. Also disclosed are pharmaceutical compositions comprising the compounds of formula I. Also disclosed are the uses of the compounds of formula I for treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion). Also disclosed are uses of the compounds of formula I in combination with a H1 receptor antagonist for treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion).

  公开了式 I 的新型化合物，其中 M1 是 CH 或 N，M2 是 C(R3) 或 N；R1 是任选取代的吲哚基或其氮杂衍生物；R2 是任选取代的芳基或杂芳基；其余变量如说明书中所定义。还公开了包含式 I 化合物的药物组合物。还公开了式 I 化合物用于治疗各种疾病或病症的用途，例如过敏、过敏引起的气道反应和鼻塞（如鼻塞）。还公开了式 I 化合物与 H1 受体拮抗剂结合用于治疗各种疾病或病症的用途，例如过敏、过敏引起的气道反应和充血（如鼻塞）。