Pyrrolopyrimidine derivatives as NR2B NMDA receptor antagonists

A compound, chemical entity technology, applied in the field of pyrrolopyrimidine derivatives as NR2B NMDA receptor antagonists

Active Publication Date: 2017-05-24
RUGEN HLDG CAYMAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present invention specifically addresses the need for improved NR2B receptor antagonists in one or more of aspects such a

Method used

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  • Pyrrolopyrimidine derivatives as NR2B NMDA receptor antagonists
  • Pyrrolopyrimidine derivatives as NR2B NMDA receptor antagonists
  • Pyrrolopyrimidine derivatives as NR2B NMDA receptor antagonists

Examples

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example

[0573] As depicted in the Examples below, in certain illustrative embodiments, chemical entities are prepared according to the following procedures. It will be appreciated that while the general methods describe the synthesis of certain chemical entities of the invention, the following methods and others known to those skilled in the art are also applicable to all chemical entities as described herein and to these chemical entities respective subclasses and kinds.

[0574] Temperatures are given in degrees Celsius. If not mentioned otherwise, all evaporations are performed under reduced pressure, preferably between 15 mm Hg and 100 mm Hg. The structures of intermediates and final products were determined by standard analytical methods, such as mass spectrometry and NMR spectroscopy.

[0575] abbreviation:

[0576] aq aqueous solution

[0577] Boc tert-butoxycarbonyl

[0578] Cbz benzyloxycarbonyl

[0579] DAST diethylaminosulfur trifluoride

[0580] DCM dichloromethane ...

example 1

[0605] Example 1. Chemical entity.

example 1A

[0606] Example 1.A. Intermediates.

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Abstract

Disclosed are chemical entities of formula I: [INSERT CHEMICAL FORMULA HERE] wherein X, Y, Z, R1, R3, R4, R5 and R6 are defined herein, as NR2B subtype selective receptor antagonists. Also disclosed are pharmaceutical compositions comprising a chemical entity of formula I, and methods of treating various diseases and disorders associated with NR2B antagonism, e.g., diseases and disorders of the CNS, such as depression, by administering a chemical entity of formula I.

Description

Background technique [0001] Nonselective NMDA receptor antagonists were originally developed for stroke and head trauma, and have shown clinical efficacy in the treatment of depression in recent years. The nonselective NMDA receptor antagonist ketamine has been shown to have rapid onset and efficacy in depression resistant to standard monoamine reuptake inhibitor therapy (Mathews and Zarat Zarate), 2013, J. Clin. Psychiatry 74:516-158). However, nonselective NMDA receptor antagonists, such as ketamine, have various undesirable pharmacological activities that limit their application in humans. Specifically, dissociative or psychotropic side effects are particularly prominent for non-selective NMDA receptor antagonists. In recent years, NR2B subtype-selective NMDA receptor antagonists have shown potential in numerous clinical indications. Specifically, NR2B antagonists have also demonstrated antidepressant activity in early clinical trials (Ibrahim et al., 2012, J. Clin. Psyc...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/519A61P25/24A61P25/16A61P25/28
CPCC07D487/04A61K31/519A61P25/00A61P25/04A61P25/08A61P25/14A61P25/16A61P25/24A61P25/28A61P25/30A61P43/00A61P9/10A61K9/0053
Inventor 吉迪恩·夏皮罗
Owner RUGEN HLDG CAYMAN
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