methyl 3-[(dimethylamino)methyl]-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate | 868552-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: methyl 3-[(dimethylamino)methyl]-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate
• 英文别名: 3-dimethylaminomethyl-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid methyl ester；1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,3-[(dimethylamino)methyl]-1-[(4-fluorophenyl)methyl]-,methyl ester；methyl 3-[(dimethylamino)methyl]-1-[(4-fluorophenyl)methyl]pyrrolo[2,3-c]pyridine-5-carboxylate
• CAS: 868552-11-8
• 化学式: C₁₉H₂₀FN₃O₂
• 分子量: 341.385
• InChiKey: MKNFNQJGVXNIKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-[(dimethylamino)methyl]-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate 在 氯甲酸乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,3-(chloromethyl)-1-[(4-fluorophenyl)methyl]-,methyl ester
  参考文献：
  名称：

  [EN] PYRROLOPYRIDINE DERIVATIVES AND THEIR USE AS HIV-INTEGRASE INHIBITORS
  [FR] INHIBITEURS DE L'ENZYME INTEGRASE DU VIH

  摘要：

  公开号：

  WO2005103003A3
• 作为产物：
  描述：

  methyl 1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate 、 N,N-二甲基氯烯亚胺 以 乙腈 为溶剂， 反应 1.0h， 以97%的产率得到methyl 3-[(dimethylamino)methyl]-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate
  参考文献：
  名称：

  [EN] INHIBITORS OF THE HIV INTEGRASE ENZYME
  [FR] INHIBITEURS DE L'ENZYME INTEGRASE DU VIH

  摘要：

  本发明涉及公式(I)的化合物，或其药物可接受的盐或溶剂化物，包含公式(I)化合物的药物组合物，以及它们在治疗HIV感染哺乳动物中的用途方法。

  公开号：

  WO2006027694A1

文献信息

• Inhibitors of the HIV integrase enzyme
  申请人：Dress Ruprecht Klaus

  公开号：US20050277662A1

  公开（公告）日：2005-12-15

  The present invention is directed to compounds of formula (I), and pharmaceutically acceptable salts and solvates thereof, their synthesis, and their use as modulators or inhibitors of the human immunodeficiency virus (“HIV”) integrase enzyme.

  本发明涉及公式（I）的化合物，以及其药学上可接受的盐和溶剂化物，它们的合成以及它们作为人类免疫缺陷病毒（“HIV”）整合酶酶的调节剂或抑制剂的用途。
• Inhibitors of the Hiv Integrase Enzyme
  申请人：Dress Ruprecht Klaus

  公开号：US20070232644A1

  公开（公告）日：2007-10-04

  The present invention relates to compounds of formula (I), or a pharmaceutically acceptable salt or solvate thereof, pharmaceutical compositions comprising compounds of formula (I), and their methods of use in treating HIV-infected mammals.

  本发明涉及公式(I)的化合物，或其药学上可接受的盐或溶剂，包括公式(I)的化合物的制药组合物，以及它们在治疗感染HIV的哺乳动物中的使用方法。
• INHIBITORS OF THE HIV INTEGRASE ENZYME
  申请人：Dress Klaus Ruprecht

  公开号：US20090170846A1

  公开（公告）日：2009-07-02

  The present invention is directed to compounds of formula (I), and pharmaceutically acceptable salts and solvates thereof, their synthesis, and their use as modulators or inhibitors of the human immunodeficiency virus “HIV” integrase enzyme. Formula (I).

  本发明涉及公式（I）的化合物，以及其制备的药用可接受的盐和溶剂，以及它们作为人类免疫缺陷病毒“HIV”整合酶酶的调节剂或抑制剂的用途。公式（I）。
• Azaindole N-methyl hydroxamic acids as HIV-1 integrase inhibitors-II. The impact of physicochemical properties on ADME and PK
  作者：Steven P. Tanis、Michael B. Plewe、Ted W. Johnson、Scott L. Butler、Deepak Dalvie、Dorothy DeLisle、Klaus R. Dress、Qiyue Hu、Buwen Huang、Jon E. Kuehler、Atsuo Kuki、Wen Liu、Qinghai Peng、Graham L. Smith、Jim Solowiej、Khanh T. Tran、Hai Wang、Anle Yang、Chunfeng Yin、Xiaoming Yu、Junhu Zhang、Huichun Zhu

  DOI：10.1016/j.bmcl.2010.10.022

  日期：2010.12

  HIV-1 integrase is one of three enzymes encoded by the HIV genome and is essential for viral replication, and HIV-1 IN inhibitors have emerged as a new promising class of therapeutics. Recently, we reported the discovery of azaindole hydroxamic acids that were potent inhibitors of the HIV-1 IN enzyme. N-Methyl hydroxamic acids were stable against oxidative metabolism, however were cleared rapidly through phase 2 glucuronidation pathways. We were able to introduce polar groups at the beta-position of the azaindole core thereby altering physical properties by lowering calculated log D values (c Log D) which resulted in attenuated clearance rates in human hepatocytes. Pharmacokinetic data in dog for representative compounds demonstrated moderate oral bioavailability and reasonable half-lives. These ends were accomplished without a large negative impact on enzymatic and antiviral activity, thus suggesting opportunities to alter clearance parameters in future series. (C) 2010 Elsevier Ltd. All rights reserved.
• WO2007/39802
  申请人：——

  公开号：——

  公开（公告）日：——