(S)-8-(1-isopropyl-piperidin-4-yloxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

• 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: (S)-8-(1-isopropyl-piperidin-4-yloxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one
• 英文别名: (S)-8-(1-isopropylpiperidin-4-yloxy)-4-methyl-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one；(4S)-4-methyl-8-(1-propan-2-ylpiperidin-4-yl)oxy-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one
• 化学式: C₂₀H₂₇N₃O₂
• 分子量: 341.453
• InChiKey: JGXUYJUQTMMZNX-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-8-(1-isopropyl-piperidin-4-yloxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one 、 sodium;hydride 、 溴甲基环丙烷 在 (S)-2-cyclopropylmethyl-8-(1-isopropyl-piperidin-4-yloxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one 作用下， 以to give the desired product as a light yellow solid (55%)的产率得到(S)-2-cyclopropylmethyl-8-(1-isopropyl-piperidin-4-yloxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one
  参考文献：
  名称：

  Tricyclic Amide Derivatives

  摘要：

  本发明涉及式I的化合物，其中A，G，r和R1至R5如描述和要求中所定义，并且其药学上可接受的盐。这些化合物可用于治疗和/或预防与H3受体调节有关的疾病。

  公开号：

  US20090156583A1
• 作为产物：
  描述：

  1-异丙基-4-哌啶醇 、 (S)-8-hydroxy-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one 在 偶氮二甲酸二叔丁酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-8-(1-isopropyl-piperidin-4-yloxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one
  参考文献：
  名称：

  基于3,4-二氢-2 H-吡嗪并[1,2- a ]吲哚-1-酮骨架的强效选择性组胺H 3受体反向激动剂的发现

  摘要：

  已经发现了基于3，4-二氢-2 H-吡嗪并[1,2 - a ]吲哚-1-酮骨架的一系列新的强组胺H 3受体反向激动剂。几种化合物显示出对其他组胺受体亚型的高选择性，并具有良好的理化特性，对CYP450酶的抑制作用低以及微粒体制剂中的高代谢稳定性。（- [R）-2-环丙基甲基-8-（1-异丙基-哌啶-4-基氧基）-3-甲基-3,4-二氢-2 H ^ -吡嗪并[1,2一]吲哚-1-酮（8吨）口服后在急性大鼠成水模型中表现出良好的体内功效。

  DOI：

  10.1016/j.bmcl.2010.08.009
• 作为试剂：
  描述：

  (S)-8-hydroxy-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one 、 1-异丙基-4-哌啶醇 、 三苯基膦 、 偶氮二甲酸二叔丁酯 在 (S)-8-(1-isopropyl-piperidin-4-yloxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one 作用下， 以to give the desired product as a light yellow foam (52%)的产率得到(S)-8-(1-isopropyl-piperidin-4-yloxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one
  参考文献：
  名称：

  Tricyclic amide derivatives

  摘要：

  本发明涉及公式I的化合物，其中A、G、r和R1至R5如描述和权利要求中所定义，并且其药学上可接受的盐。这些化合物对于治疗和/或预防与H3受体调节相关的疾病是有用的。

  公开号：

  US20070135416A1

文献信息

• Tricyclic amide derivatives as modulators of H3 receptors
  申请人：Hoffmann-La Roche Inc.

  公开号：US07786109B2

  公开（公告）日：2010-08-31

  The present invention relates to compounds of formula I wherein A, G, r and R1 to R5 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prevention of diseases which are associated with the modulation of H3 receptors such as, for example, diabetes mellitus.

  本发明涉及式I的化合物，其中A、G、r和R1到R5在说明书和权利要求中定义，并且其药学上可接受的盐。这些化合物可用于治疗和/或预防与调节H3受体相关的疾病，例如糖尿病。
• Synthesis of lactams
  申请人：Tavares Francis Xavier

  公开号：US10202392B2

  公开（公告）日：2019-02-12

  Methods for the synthesis of lactams are presented whereby a carboxylic acid of the formula HOOC—OR—NH-LG, wherein OR is an organic moiety and LG is a leaving group, is reacted with an acid, such as an organic acid, in particular a strong acid, and a dehydrating agent, which may be one in the same such as a strong acid anhydride, such that the amount of acid added allows for the desired transformation to take place without the loss of the leaving group (LG) before the cyclization, and recovering the lactam.

  本发明提出了合成内酰胺的方法，即将式 HOOC-OR-NH-LG（其中 OR 为有机分子，LG 为离去基团）的羧酸与一种酸（如有机酸，特别是强酸）和一种脱水剂（可以是同一种脱水剂，如强酸酸酐）反应，使加入的酸量能够在环化前发生所需的转化而不损失离去基团（LG），从而回收内酰胺。
• TRICYCLIC AMIDE DERIVATIVES USEFUL FOR TREATING OBESITY
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1960401A1

  公开（公告）日：2008-08-27
• SYNTHESIS OF LACTAMS
  申请人：Tavares Francis Xavier

  公开号：US20150087831A1

  公开（公告）日：2015-03-26

  Methods for the synthesis of lactams are presented whereby a carboxylic acid of the formula HOOC—OR—NH-LG, wherein OR is an organic moiety and LG is a leaving group, is reacted with an acid, such as an organic acid, in particular a strong acid, and a dehydrating agent, which may be one in the same such as a strong acid anhydride, such that the amount of acid added allows for the desired transformation to take place without the loss of the leaving group (LG) before the cyclization, and recovering the lactam.
• Process for Synthesis of Lactams
  申请人：TAVARES Francis Xavier

  公开号：US20160257688A1

  公开（公告）日：2016-09-08

  Methods for the synthesis of lactams are presented whereby a carboxylic acid of the formula HOOC—OR—NH-LG, wherein OR is an organic moiety and LG is a leaving group, is reacted with an acid, such as an organic acid, in particular a strong acid, and a dehydrating agent, which may be one in the same such as a strong acid anhydride, such that the amount of acid added allows for the desired transformation to take place without the loss of the leaving group (LG) before the cyclization, and recovering the lactam such as that of the formula (a), provided herein, wherein G represents the atom(s) needed to form a closed ring.