4-amino-N-(3-dimethylaminopropyl)-N-methylbenzamide | 466694-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-N-(3-dimethylaminopropyl)-N-methylbenzamide
• 英文别名: 4-[N-methyl-N-(3-dimethylamino-propyl)-aminocarbonyl]-1-aniline；4-amino-N-(3-dimethylamino-propyl)-N-methyl-benzamide；4-amino-N-[3-(dimethylamino)propyl]-N-methylBenzamide
• CAS: 466694-51-9
• 化学式: C₁₃H₂₁N₃O
• mdl: MFCD16318611
• 分子量: 235.329
• InChiKey: YLLPACHGOOZABB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  49.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-amino-N-(3-dimethylaminopropyl)-N-methylbenzamide 、 (E)-methyl 1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate 生成 (Z)-3-({4-[(3-dimethylaminopropyl)-methyl-carbamoyl]-phenylamino}-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Substituted indolinones

  摘要：

  本发明涉及一种通式1中6位取代的吲哚酮，其中R1至R5和X的定义如权利要求1中定义的，其异构体和盐，特别是具有有价值的药理特性的生理上可接受的盐，特别是对各种受体酪氨酸激酶和细胞周期蛋白/CDK复合物以及内皮细胞增殖具有抑制作用的物质，含有这些化合物的药物组合物，其用途和制备这些化合物的方法。

  公开号：

  US20030092756A1
• 作为产物：
  描述：

  N-(3-(dimethyl amino)propyl)-N-methyl-4-nitrobenzamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 1.5h， 生成 4-amino-N-(3-dimethylaminopropyl)-N-methylbenzamide
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Indolinones as Triple Angiokinase Inhibitors and the Discovery of a Highly Specific 6-Methoxycarbonyl-Substituted Indolinone (BIBF 1120)

  摘要：

  Inhibition of tumor angiogenesis through blockade of the vascular endothelial growth factor (VEGF) signaling pathway is a new treatment modality in oncology. Preclinical findings suggest that blockade of additional pro-angiogenic kinases, such as Fibroblast and platelet-derived growth factor receptors (FGFR and PDGFR), may improve the efficacy of pharmacological cancer treatment. Indolinones substituted in position 6 were identified as selective inhibitors of VEGF-, PDGF-, and FGF-receptor kinases. In particular, 6-methoxycarbonyl-substituted indolinones showed a highly favorable selectivity profile. Optimization identified potent inhibitors of VEGF-related endothelial cell proliferation with additional efficacy on pericyctes and smooth muscle cells. In contrast, no direct inhibition of tumor cell proliferation was observed. Compounds 2 (BIBF 1000) and 3 (BIBF 1120) are orally available and display encouraging efficacy in in vivo tumor models while being well tolerated. The triple angiokinase inhibitor 3 is currently in phase III clinical trials for the treatment of nonsmall cell lung cancer.

  DOI：

  10.1021/jm900431g

文献信息

• Indolinone derivatives substituted in the 6 position, the preparation thereof and their use as pharmaceutical compositions
  申请人：Heckel Armin

  公开号：US20060194813A1

  公开（公告）日：2006-08-31

  The present invention relates to indolinone derivatives substituted in the 6 position of general formula wherein R 1 to R 6 and X are defined as in claim 1 , the tautomers, enantiomers, diastereomers, mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof, which have valuable pharmacological properties, in particular an inhibiting effect on various receptor tyrosine kinases and on the proliferation of endothelial cells and various tumour cells, pharmaceutical compositions containing these compounds, their use and processes for preparing them.

  本发明涉及一种在通式中6位取代的吲哚酮衍生物，其中R1至R6和X如权利要求1所定义，其互变异构体、对映异构体、顺反异构体、混合物及其盐，特别是其生理上可接受的盐，具有有价值的药理特性，特别是对各种受体酪氨酸激酶和内皮细胞以及各种肿瘤细胞的增殖具有抑制作用，包含这些化合物的制药组合物，它们的用途和制备过程。
• Indolinones substituted by heterocycles, the preparation thereof and their use as medicaments
  申请人：Kley Joerg

  公开号：US20050054710A1

  公开（公告）日：2005-03-10

  The present invention relates to heterocyclically substituted indolinones of general formula wherein R 1 to R 5 and X are defined as in claim 1, the tautomers, the diastereomers, the enantiomers, the mixtures thereof, the prodrugs thereof and the salts thereof, particularly the physiologically acceptable salts thereof which have valuable pharmacological properties, in particular an inhibiting effect on various receptor tyrosine kinases and cyclin/CDK complexes and on the proliferation of endothelial cells and various tumour cells, pharmaceutical compositions containing these compounds, their use and processes for preparing them.

  本发明涉及一般式为的杂环取代吲哚酮 其中R1至R5和X的定义如权利要求1中所述，其互变异构体、对映异构体、混合物、前药及其盐，特别是具有有价值的药理学特性，特别是对各种受体酪氨酸激酶和环/ CDK复合物以及内皮细胞和各种肿瘤细胞的增殖具有抑制作用的生理上可接受的盐，包含这些化合物的制药组合物，它们的用途和制备它们的过程。
• IN 6-STELLUNG SUBSTITUIERTE INDOLINE UND IHRE VERWENDUNG ALS KINASE-INHIBITOREN
  申请人：Boehringer Ingelheim Pharma GmbH & Co.KG

  公开号：EP1379501A1

  公开（公告）日：2004-01-14
• IN 6-STELLUNG SUBSTITUIERTE INDOLINONDERIVATE, IHRE HERSTELLUNG UND IHRE VERWENDUNG ALS ARZNEIMITTEL
  申请人：BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG

  公开号：EP1527046A1

  公开（公告）日：2005-05-04
• US6858641B2
  申请人：——

  公开号：US6858641B2

  公开（公告）日：2005-02-22