N-[3-(dimethylamino)propyl]-5-chloro-2,3-dihydro-2-oxo-1H-indole-1-carboxamide | 265994-71-6

• 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
• 英文名称: N-[3-(dimethylamino)propyl]-5-chloro-2,3-dihydro-2-oxo-1H-indole-1-carboxamide
• 英文别名: N-[3-(Dimethylamino)propyl]-5-chloro-2,3-dihydro2-oxo-1H-indole-1-carboxamide；5-chloro-N-[3-(dimethylamino)propyl]-2-oxo-3H-indole-1-carboxamide
• CAS: 265994-71-6
• 化学式: C₁₄H₁₈ClN₃O₂
• 分子量: 295.769
• InChiKey: IURCMBBEUOJGDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-噻吩甲酰氯 、 N-[3-(dimethylamino)propyl]-5-chloro-2,3-dihydro-2-oxo-1H-indole-1-carboxamide 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (Z)-N-[3-(dimethylamino)propyl]-5-chloro-2,3-dihydro-3-(hydroxy-2-thienylmethylene)-2-oxo-1H-indole-1-carboxamide
  参考文献：
  名称：

  Synthesis of carbon‐14 labelled (3‐{[(Z)‐5‐chloro‐2,3‐dihydro‐3‐(hydroxy‐2‐thienylmethylene)‐2‐oxo‐1 H ‐indol‐1‐yle]carbonylamino}propyl)trimethylammonium chloride, a potential cartilage‐targeted antirheumatic drug

  摘要：

  A [C-14]-labelled form of (3-{[(Z)-5-chloro-2,3-dihydro-3-(hydroxy-2-thienylmethylene)-2-oxo-1H-indol-1-yle]carbonylamino}propyl)trimethylammonium chloride, a potential cartilage-targeted antirheumatic drug, was required for pharmacokinetic studies. This compound, labelled with [C-14] located in the C-3 methylene position, was prepared in four steps starting from N-[3-(dimethylamino)propyl]-5-chloro-2,3-dihydro-2-oxo-1H-indole-1-carboxamide and 2-thiophene-[C-14]carbonyl chloride, previously synthesized by a two-step sequence from barium [C-14]-carbonate and 2-thienyllithium. The desired product was obtained with a specific activity of 359 MBq/mmol (9.7 mCi/mmol). The overall radiochemical yield was 50% based on barium [C-14]-carbonate.

  DOI：

  10.1002/(sici)1099-1344(20000315)43:3<297::aid-jlcr317>3.0.co;2-#
• 作为产物：
  描述：

  5-氯氧化吲哚 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 N-[3-(dimethylamino)propyl]-5-chloro-2,3-dihydro-2-oxo-1H-indole-1-carboxamide
  参考文献：
  名称：

  Synthesis of carbon‐14 labelled (3‐{[(Z)‐5‐chloro‐2,3‐dihydro‐3‐(hydroxy‐2‐thienylmethylene)‐2‐oxo‐1 H ‐indol‐1‐yle]carbonylamino}propyl)trimethylammonium chloride, a potential cartilage‐targeted antirheumatic drug

  摘要：

  A [C-14]-labelled form of (3-{[(Z)-5-chloro-2,3-dihydro-3-(hydroxy-2-thienylmethylene)-2-oxo-1H-indol-1-yle]carbonylamino}propyl)trimethylammonium chloride, a potential cartilage-targeted antirheumatic drug, was required for pharmacokinetic studies. This compound, labelled with [C-14] located in the C-3 methylene position, was prepared in four steps starting from N-[3-(dimethylamino)propyl]-5-chloro-2,3-dihydro-2-oxo-1H-indole-1-carboxamide and 2-thiophene-[C-14]carbonyl chloride, previously synthesized by a two-step sequence from barium [C-14]-carbonate and 2-thienyllithium. The desired product was obtained with a specific activity of 359 MBq/mmol (9.7 mCi/mmol). The overall radiochemical yield was 50% based on barium [C-14]-carbonate.

  DOI：

  10.1002/(sici)1099-1344(20000315)43:3<297::aid-jlcr317>3.0.co;2-#

文献信息

• Quaternary ammonium compounds
  申请人：Les Laboratoires Servier

  公开号：US06759406B1

  公开（公告）日：2004-07-06

  Compounds of formula corresponding to either formula (Ia) or (Ib): wherein: M represents a molecule that can be used for the treatment or diagnosis of pathologies caused by attack on the cartilage, R1, R2 and R3 represent an alkyl group, or R1, R2 and R3, together with the nitrogen atom carrying them, form a heterocycle, X represents a (C1-C6)alkylene chain in which one or more —CH2— groups are optionally replaced by a sulphur atom, an oxygen atom, or an —NR—, —CO—, —CO—NH—, —CO2—, —SO— or —SO2— group, n represents 0 or 1, Hal represents a halogen atom, or, R4 represents an alkyl group, Hal represents a halogen atom, represents a molecule that can be used for the treatment or diagnosis of pathologies caused by attack on the cartilage, wherein the nitrogen atom may optionally be included in a saturated or unsaturated nitrogen-containing heterocyclic system, or included in a double bond; and pharmaceutical compositions thereof.

  具有与化学式（Ia）或（Ib）相对应的化合物： 其中： M代表可用于治疗或诊断由对软骨的攻击引起的病理的分子， R1、R2和R3代表烷基基团，或R1、R2和R3与携带它们的氮原子一起形成杂环， X代表（C1-C6）烷基链，其中一个或多个—CH2—基团可以选择性地被硫原子、氧原子或—NR—、—CO—、—CO—NH—、—CO2—、—SO—或—SO2—基团所取代， n代表0或1， Hal代表卤素原子， 或， R4代表烷基基团， Hal代表卤素原子， 代表可用于治疗或诊断由对软骨的攻击引起的病理的分子，其中氮原子可以选择性地包含在饱和或不饱和的含氮杂环系统中，或包含在双键中；以及其药物组成物。
• New quaternary ammonium compounds
  申请人：——

  公开号：US20040208822A1

  公开（公告）日：2004-10-21

  A compound of formula corresponding to either formula (Ia) or (Ib): 1 wherein: M represents a molecule that can be used for the treatment or diagnosis of pathologies caused by attack on the cartilage, R 1 , R 2 and R 3 represent alkyl, or R 1, R 2 and R 3 together with the nitrogen atom carrying them, form a heterocycle, X represents a (C 1 -C 6 )alkylene chain in which one or more —CH 2 — groups are optionally replaced by sulphur, oxygen, or —NR—, —CO—, —CO—NH—, —CO 2 —, —SO— or —SO 2 —, n represents 0 or 1, Hal represents halogen, or, 2 R 4 represents alkyl, Hal represents halogen, 3 represents a molecule that can be used for the treatment or diagnosis of pathologies caused by attack on the cartilage, wherein the nitrogen atom may optionally be included in a saturated or unsaturated nitrogen-containing heterocyclic system, or included in a double bond.

  化合物的化学式对应于公式(Ia)或(Ib)中的任意一种： 其中， M代表可用于治疗或诊断由对软骨的攻击引起的病理的分子， R1、R2和R3代表烷基，或者R1、R2和R3连同它们携带的氮原子形成一个杂环， X代表一个(C1-C6)烷基链，其中一个或多个—CH2—基团可选择地被硫、氧、—NR—、—CO—、—CO—NH—、—CO2—、—SO—或—SO2—取代， n代表0或1， Hal代表卤素， 或者， 2R4代表烷基， Hal代表卤素， 3代表可用于治疗或诊断由对软骨的攻击引起的病理的分子，其中氮原子可选择地包括在饱和或不饱和的含氮杂环系统中，或包括在双键中。
• DERIVES D' AMONIUM QUATERNAIRE, LEUR PROCEDE DE PREPARATION ET LEUR USAGE EN PHARMACIE
  申请人：Institut National de la Santé et de la Recherche Médicale

  公开号：EP1185526B1

  公开（公告）日：2004-09-15
• US7008613B2
  申请人：——

  公开号：US7008613B2

  公开（公告）日：2006-03-07
• Synthesis of carbon‐14 labelled (3‐{[(Z)‐5‐chloro‐2,3‐dihydro‐3‐(hydroxy‐2‐thienylmethylene)‐2‐oxo‐1 <i>H</i> ‐indol‐1‐yle]carbonylamino}propyl)trimethylammonium chloride, a potential cartilage‐targeted antirheumatic drug
  作者：Isabelle Giraud、Maryse Rapp、Jean‐Michel Dupuy、Jean‐Claude Maurizis、Jean‐Claude Madelmont

  DOI：10.1002/(sici)1099-1344(20000315)43:3<297::aid-jlcr317>3.0.co;2-#

  日期：2000.3.15

  A [C-14]-labelled form of (3-[(Z)-5-chloro-2,3-dihydro-3-(hydroxy-2-thienylmethylene)-2-oxo-1H-indol-1-yle]carbonylamino}propyl)trimethylammonium chloride, a potential cartilage-targeted antirheumatic drug, was required for pharmacokinetic studies. This compound, labelled with [C-14] located in the C-3 methylene position, was prepared in four steps starting from N-[3-(dimethylamino)propyl]-5-chloro-2,3-dihydro-2-oxo-1H-indole-1-carboxamide and 2-thiophene-[C-14]carbonyl chloride, previously synthesized by a two-step sequence from barium [C-14]-carbonate and 2-thienyllithium. The desired product was obtained with a specific activity of 359 MBq/mmol (9.7 mCi/mmol). The overall radiochemical yield was 50% based on barium [C-14]-carbonate.