N-(吡啶-4-基)-1H-吲哚-1-胺 | 119257-33-9

• 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: N-(吡啶-4-基)-1H-吲哚-1-胺
• 英文名称: P 86-7480
• 英文别名: N-(pyridin-4-yl)-N-1H-indolyl-1-amine；N-(4-pyridinyl)-1H-indol-1-amine；N-pyridin-4-ylindol-1-amine
• CAS: 119257-33-9
• 化学式: C₁₃H₁₁N₃
• 分子量: 209.25
• InChiKey: YFXZWVUZIPQSKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(吡啶-4-基)-1H-吲哚-1-胺 在 吡啶 、 盐酸羟胺 、 sodium hydride 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-propyl-N-(4-pyridinyl)-1H-indol-1-amine-3-carboxaldehyde oxime
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of N-Propyl-N-(4-pyridinyl)-1H-indol-1-amine (Besipirdine) and Related Analogs as Potential Therapeutic Agents for Alzheimer's Disease

  摘要：

  A series of novel N-(4-pyridinyl)-1H-indol-1-amines and other heteroaryl analogs was synthesized and evaluated in tests to determine potential utility for the treatment of Alzheimer's disease. From these compounds, N-propyl-N-(4-pyridinyl)-1H-indol-1-amine (besipirdine, 4c) was selected for clinical development based on in-depth biological evaluation. In addition to cholinomimetic properties based initially on in vitro inhibition of [H-3]quinuclidinyl benzilate binding, in. vivo reversal of scopolamine-induced behavioral deficits, and subsequently on other results, 4c also displayed enhancement of adrenergic mechanisms as evidenced in vitro by inhibition of [H-3]clonidine binding and synaptosomal biogenic amine uptake, and in vivo by reversal of tetrabenazine-induced ptosis. The synthesis, structure-activity relationships for this series, and the biological profile of 4c are reported.

  DOI：

  10.1021/jm9506433
• 作为产物：
  描述：

  1H-吲哚-1-胺 、 4-氯吡啶盐酸盐 以 异丙醇 为溶剂， 反应 2.0h， 以50%的产率得到N-(吡啶-4-基)-1H-吲哚-1-胺
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of N-Propyl-N-(4-pyridinyl)-1H-indol-1-amine (Besipirdine) and Related Analogs as Potential Therapeutic Agents for Alzheimer's Disease

  摘要：

  A series of novel N-(4-pyridinyl)-1H-indol-1-amines and other heteroaryl analogs was synthesized and evaluated in tests to determine potential utility for the treatment of Alzheimer's disease. From these compounds, N-propyl-N-(4-pyridinyl)-1H-indol-1-amine (besipirdine, 4c) was selected for clinical development based on in-depth biological evaluation. In addition to cholinomimetic properties based initially on in vitro inhibition of [H-3]quinuclidinyl benzilate binding, in. vivo reversal of scopolamine-induced behavioral deficits, and subsequently on other results, 4c also displayed enhancement of adrenergic mechanisms as evidenced in vitro by inhibition of [H-3]clonidine binding and synaptosomal biogenic amine uptake, and in vivo by reversal of tetrabenazine-induced ptosis. The synthesis, structure-activity relationships for this series, and the biological profile of 4c are reported.

  DOI：

  10.1021/jm9506433

文献信息

• Use of unsubstituted and substituted n-(pyrrol-1-yl)pyridinamines as
  申请人：Hoechst Marion Roussel, Inc.

  公开号：US05776955A1

  公开（公告）日：1998-07-07

  This invention relates to a method of treating a patient in need of relief from convulsions which comprises administering to such a patient a convulsion-alleviating amount of a compound of the formula ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, m and n are as defined within.

  这项发明涉及一种治疗需要缓解抽搐症状的患者的方法，包括向该患者施用化合物的缓解抽搐量，该化合物的化学式为##STR1##其中R、R.sup.1、R.sup.2、R.sup.3、R.sup.4、m和n的定义如内所述。
• Use of N-(pyridinyl)-1H-indol-1-amines for the treatment of
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US05356910A1

  公开（公告）日：1994-10-18

  There is disclosed a method of alleviating obsessive compulsive disorders which comprises administration of an effective amount of a compound of the formula. ##STR1## where m is 1 or 2; R is H, halogen, loweralkyl, loweralkoxy, arylloweralkoxy, hydroxy, nitro, amino, loweralkylamino or diloweralkylamino; R.sub.1 is H or loweralkyl; R.sub.2 is H or loweralkyl; and R.sub.3 is H, halogen or loweralkyl.

  揭示了一种缓解强迫症障碍的方法，其中包括给予公式化合物的有效量。##STR1## 其中m为1或2；R为H、卤素、较低烷基、较低烷氧基、芳基较低烷氧基、羟基、硝基、氨基、较低烷基氨基或二较低烷基氨基；R.sub.1为H或较低烷基；R.sub.2为H或较低烷基；R.sub.3为H、卤素或较低烷基。
• N-(pyridinyl)-1H-indol-1-amines
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04970218A1

  公开（公告）日：1990-11-13

  There are disclosed compounds of the formula, ##STR1## where m, n, p, R, R.sub.1, R.sub.2 and R.sub.3 are as defined in the specification; which compounds are useful for enhancing memory and also as analgesic and antidepressant agents.

  公式中披露了化合物，其中m、n、p、R、R.sub.1、R.sub.2和R.sub.3如规范中定义；这些化合物对增强记忆、作为镇痛剂和抗抑郁剂都很有用。
• Crystal Form of Besipirdine Chlorhydrate, Process Preparation and Use Thereof
  申请人：Bienayme Hugues

  公开号：US20090048304A1

  公开（公告）日：2009-02-19

  Crystal form of besipirdine chlorhydrate (Form I) corresponding to the Formula (A) below: the aforementioned form being characterized at least by one of the following physico-chemical properties: a) In FTIR, it displays at least the following absorption bands of the infrared spectrum: 778, 1198, 1121, but not the following absorption bands of the infrared spectrum: 3395, 1583, 732, the aforementioned bands being expressed in cm −1 at ±5 cm −1 ; b) In PXRD, it shows at least the following reflections, which are the most intense ones but whose intensity hereafter is given for information only: Formula (II) c) In DSC, it displays at least an endothermic peak at 187.3±2.0° C. using 5° C./min scanning conditions, and a fusion enthalpy ΔH of 130.4±2.0 J/g. The invention also relates to the processes used for the preparation of form I as well as its applications in urology.

  Besipirdine chlorhydrate的晶体形态（I型）对应于下面的公式（A）：上述形式至少具有以下物理化学特性之一：a）在FTIR中，它显示出红外光谱的至少以下吸收带：778、1198、1121，但不包括以下吸收带：3395、1583、732，上述带子以±5 cm-1表达；b）在PXRD中，它至少显示出以下反射，这些反射是最强烈的，但其强度仅供参考：公式（II）c）在DSC中，它至少显示出一个在187.3±2.0℃下的吸热峰，使用5℃/min扫描条件，并具有130.4±2.0 J/g的熔融焓ΔH。本发明还涉及用于制备I型的过程以及其在泌尿学中的应用。
• [EN] USE OFF UNSUBSTITUTED AND SUBSTITUTED N-(PYRROL-1-YL)PYRIDINAMINES AS ANTICONVULSANT AGENTS<br/>[FR] UTILISATION DE N-(PYRROL-1-YL)PYRIDINAMINES SUBSTITUEES ET NON SUBSTITUEES EN TANT QU'AGENTS ANTICONVULSIVANTS
  申请人：HOECHST MARION ROUSSEL, INC.

  公开号：WO1997004777A1

  公开（公告）日：1997-02-13

  (EN) This invention relates to a method of treating a patient in need of relief from convulsions which comprises administering to such a patient a convulsion-alleviating amount of a compound of formula (I), wherein R, R1, R2, R3, R4, m and n are as defined within.(FR) Procédé de traitement d'un patient souffrant de convulsions, qui consiste à administrer à ce patient une quantité suffisante pour atténuer les convulsions d'un composé de formule (I) dans laquelle R, R1, R2, R3, R4, m et n sont tels que définis dans le descriptif.

  该发明涉及一种治疗需要缓解抽搐症状的患者的方法，包括向该患者施用公式（I）化合物的缓解抽搐的剂量，其中R、R1、R2、R3、R4、m和n如描述中所定义。(翻译结果)