N-methyl-5-chloro-2-(4-chlorophenyl)indole acid | 290832-35-8

• 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
• 英文名称: N-methyl-5-chloro-2-(4-chlorophenyl)indole acid
• 英文别名: 5-chloro-2-(4-chlorophenyl)-1-methyl-1H-indole-3-propanoic acid；3-[5-chloro-2-(4-chlorophenyl)-1-methylindol-3-yl]propanoic acid
• CAS: 290832-35-8
• 化学式: C₁₈H₁₅Cl₂NO₂
• 分子量: 348.229
• InChiKey: MUCUZLSHVYFJFI-UHFFFAOYSA-N

物化性质

• 沸点：
  562.2±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-5-chloro-2-(4-chlorophenyl)indole acid 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 4-{3-[5-chloro-2-(4-chlorophenyl)-1-methyl-1H-indol-3-yl]-1-oxopropyl}-1-(phenylmethyl)piperazinone
  参考文献：
  名称：

  2-aryl indole derivative as antagonists of tachykinins

  摘要：

  本发明涉及以下式（I）的化合物：其中R1a、R1b、R2、R3、R4、R5、X和n在此有所定义。这些化合物特别适用于治疗或预防抑郁症、焦虑、疼痛、炎症、偏头痛、呕吐和带状疱疹后神经痛。

  公开号：

  US06518273B1
• 作为产物：
  描述：

  methyl 5-chloro-2-(4-chlorophenyl)-1-methyl-1H-indole-3-propanoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 N-methyl-5-chloro-2-(4-chlorophenyl)indole acid
  参考文献：
  名称：

  2-Aryl indole NK1 antagonists: optimisation of the amide substituent

  摘要：

  The in vivo properties of a series of 2-arylindole NK1 antagonists have been improved, by modification of the amide substituent. The 1-(2-methoxyphenyl)piperazine amide was identified as a major area of metabolism in the lead compound 1. Replacement of this amine moiety by a 4-benzyl-4-hydroxypiperidine resulted in a compound IS with reduced clearance and improved central duration of action. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00616-3

文献信息

• 2-aryl indole derivatives and their use as therapeutic agents
  申请人：——

  公开号：US20010039286A1

  公开（公告）日：2001-11-08

  The present invention relates compounds of the formula (I): 1 wherein R 1a , R 1b ; and R 2 represent a variety of substituents; R 3 represents an optionally substituted phenyl, biphenyl or naphthyl or heteroaryl group; R 4 represents hydrogen, C 1-6 alkyl, carbonyl (=O), (CH 2 ) p phenyl or a C 1-2 alkylene bridge across the piperidine ring; R 5 and R 6 each independently represent a variety of substituents; or R 5 and R 6 together are linked so as to form an optionally substituted 5-or 6-membered ring; X represents an oxygen or a sulfur atom, two hydrogen atoms, ═NH or ═N(C 1-6 alkyl); Y is a straight or branched C 1-4 alkylene, C 2-4 alkenylene or C 2-4 alkynylene chain; the dotted line represents an optional double bond; m is zero or an integer from 1 to 4; n is an integer from 1 to 4; and p is an integer from 1 to 4; or a pharmaceutically acceptable salt thereof. The compounds are of particular use in the treatment or prevention of depression, anxiety, pain, inflammation, migaine, emesis or postherpetic neuralgia.

  本发明涉及以下式（I）的化合物： 1 其中 R 1a ，R 1b ; 和 R 2 代表各种取代基; R 3 代表可选择地取代的苯基、联苯基或萘基或杂环芳基; R 4 代表氢、C 1-6 烷基、羰基（=O）、（CH 2 ） p 苯基或穿过哌啶环的 C 1-2 烷基桥; R 5 和 R 6 各自独立地代表各种取代基; 或 R 5 和 R 6 一起连接以形成可选择地取代的5-或6-成员环; X代表氧或硫原子、两个氢原子、═NH或═N(C 1-6 烷基); Y是直链或支链C 1-4 烷基、C 2-4 烯基或C 2-4 炔基链; 虚线表示可选的双键; m为零或1至4的整数; n为1至4的整数; p为1至4的整数; 或其药学上可接受的盐。 这些化合物在治疗或预防抑郁症、焦虑、疼痛、炎症、偏头痛、呕吐或带状疱疹后神经痛方面特别有用。
• Azaindole derivatives and their use as therapeutic agents
  申请人：——

  公开号：US20020022624A1

  公开（公告）日：2002-02-21

  The present invention relates to compounds of the formula (I): 1 wherein: Het represents a heterocyclic residue selected from: 2 where the dotted line in (b) represents an optional double bond; A completes a fused pyridine ring; and B completes a fused benzene or pyridine ring. The compounds are of particular use in the treatment or prevention of depression, anxiety, pain, inflammation, migaine, emesis or postherpetic neuralgia.

  本发明涉及以下式（I）的化合物： 其中： Het代表从中选择的杂环残基： 在（b）中，虚线表示可选的双键； A完成一个融合吡啶环；以及 B完成一个融合苯或吡啶环。 这些化合物特别适用于治疗或预防抑郁症、焦虑、疼痛、炎症、偏头痛、呕吐或带状疱疹后神经痛。
• US6476045B2
  申请人：——

  公开号：US6476045B2

  公开（公告）日：2002-11-05
• US6518273B1
  申请人：——

  公开号：US6518273B1

  公开（公告）日：2003-02-11
• [EN] 2-ARYL INDOLE DERIVATIVES AS ANTAGONISTS OF TACHYKININS<br/>[FR] DERIVES DE 2-ARYLE INDOLE UTILISES COMME ANTAGONISTES DES TACHYKININES
  申请人：MERCK SHARP & DOHME

  公开号：WO2000051984A1

  公开（公告）日：2000-09-08

  The present invention relates to compounds of formula (I) wherein R?1a and R1b¿ represent a variety of substituents; R3 represents an optionally substituted phenyl, biphenyl or naphthyl group; R4 represents hydrogen, C¿1-6?alkyl, carbonyl (=O), (CH2)pphenyl or a C1-2alkylene bridge across the piperazine ring; R?5¿ represents C¿1-6?alkyl, C3-7cycloalkyl, C3-7cycloalkylC1-4alkyl, C2-6alkenyl, phenyl, naphthyl, fluorenyl, heteroaryl, (CH2)ppphenyl, (CH2)pheteroaryl, CH(phenyl)2, CH(C1-6alkyl)(phenyl), C2-4alkenyl(phenyl), (CH2)pNR?cRd, (CH¿2)pCONR?cRd, (CH¿2)mCORc, (CH2)mCO2Rc or (CH¿2?)pOH; X represents an oxygen or a sulfur atom; m is zero or an integer from 1 to 4; n is an integer from 1 to 4; p is an integer from 1 to 4; or a pharmaceutically acceptable salt thereof. The compounds are of particular use in the treatment or prevention of depression, anxiety, pain, inflammation, migraine, emesis or postherpetic neuralgia.