[6-chloro-4-(2-propoxy-ethylamino)-pyridin-3-yl]-carbamic acid tert-butyl ester | 915307-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: [6-chloro-4-(2-propoxy-ethylamino)-pyridin-3-yl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl 6-chloro-4-[(2-propoxyethyl)amino]pyridin-3-ylcarbamate；tert-butyl N-{6-chloro-4-[(2-propoxyethyl)amino]-3-pyridinyl}carbamate；tert-butyl N-[6-chloro-4-(2-propoxyethylamino)pyridin-3-yl]carbamate
• CAS: 915307-79-8
• 化学式: C₁₅H₂₄ClN₃O₃
• 分子量: 329.827
• InChiKey: DWCZHCJMCDQEES-UHFFFAOYSA-N

物化性质

• 沸点：
  426.4±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  72.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [6-chloro-4-(2-propoxy-ethylamino)-pyridin-3-yl]-carbamic acid tert-butyl ester 在 盐酸 、 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 44.0h， 生成 3,7-dichloro-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one
  参考文献：
  名称：

  Carbon-11 and Fluorine-18 Radiolabeled Pyridopyrazinone Derivatives for Positron Emission Tomography (PET) Imaging of Phosphodiesterase-5 (PDE5)

  摘要：

  The cyclic guanosine monophosphate (cGMP) specific phosphodiesterase type 5 (PDES) plays an important role in various pathologies including pulmonary arterial hypertension and cardiomyopathy. PDES represents an important therapeutic and/or prognostic target, but noninvasive assessment of PDE5 expression is lacking. The purpose of this study was to: develop and evaluate pyridopyrazinone derivatives labeled with carbon-11 or fluorine-18 as PDE5-specific PET tracers. In biodistribution studies, highest PDE5-specific retention was observed for [C-11]-12 and [F-18]-17 in the lungs of wild-type mice and in the myocardium of transgenic mice with cardiomyocyte-specific PDES overexpression at 30 min postinjection. In-vivo dynamic microPET images in rats revealed that both tracers crossed the blood-brain barrier but brain retention was not PDE5-specific. Both [C-11]-.1.2 and [F-18]-17 showed specific binding to PDE5 in myocardium of transgenic mice; however [F-18]-11 showed significantly higher PDE5-specific inhibitable binding than [C-11]-12.

  DOI：

  10.1021/acs.jmedchem.6b01666
• 作为产物：
  描述：

  5-(N-叔丁氧羰基氨基)-2-氯吡啶 在 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 25.67h， 生成 [6-chloro-4-(2-propoxy-ethylamino)-pyridin-3-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  WO2006/126082

  摘要：

  公开号：

文献信息

• Pyridine [3,4-b] Pyrazinones
  申请人：Hughes O. Robert

  公开号：US20070249615A1

  公开（公告）日：2007-10-25

  Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I: wherein R 2 , R 6A , R 6B and R 8 are as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, synthetic methods, and intermediates are also disclosed.

  本文披露了化合物及其药用可接受的盐，其中化合物具有以下结构的Formula I：其中R2、R6A、R6B和R8如规范中定义。同时还披露了相应的药物组合物、治疗方法、合成方法和中间体。
• Pyridine [3,4-b] pyrazinones
  申请人：Pharmacia & Upjohn Company LLC

  公开号：US07902195B2

  公开（公告）日：2011-03-08

  Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I: wherein R2, R6A, R6B and R8 are as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, synthetic methods, and intermediates are also disclosed.

  本文披露了化合物及其医药上可接受的盐，其中该化合物具有以下化学结构式（I）：其中R2、R6A、R6B和R8如规范中所定义。此外，还披露了相应的药物组合物、治疗方法、合成方法和中间体。
• WO2006/126083
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2006/126082
  申请人：——

  公开号：——

  公开（公告）日：——
• Investigation of aminopyridiopyrazinones as PDE5 inhibitors: Evaluation of modifications to the central ring system
  作者：Robert O. Hughes、John K. Walker、Jerry W. Cubbage、Yvette M. Fobian、D. Joseph Rogier、Steve E. Heasley、Rhadika M. Blevis-Bal、Alan G. Benson、Dafydd R. Owen、E. Jon Jacobsen、John N. Freskos、John M. Molyneaux、David L. Brown、William C. Stallings、Brad A. Acker、Todd M. Maddux、Mike B. Tollefson、Jennifer M. Williams、Joseph B. Moon、Brent V. Mischke、Jeanne M. Rumsey、Yi Zheng、Alan MacInnes、Brian R. Bond、Ying Yu

  DOI：10.1016/j.bmcl.2009.06.004

  日期：2009.8

  Efforts to improve the potency and physical properties of the aminopyridiopyrazinone class of PDE5 inhibitors through modi. cation of the core ring system are described. Five new ring systems are evaluated and features that impart improved potency and improved solubility are delineated. (C) 2009 Elsevier Ltd. All rights reserved.