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Gamma secretase modulators

A solvate, pharmaceutical technology, applied in the field of gamma secretase regulators

Inactive Publication Date: 2011-02-09
SCHERING AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, the treatment of Alzheimer's disease is limited to symptomatic therapy using symptom-modifying agents (represented by acetylcholinesterase inhibitors) and basic therapy to prevent disease progression that has not yet developed

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[1993]

[1994] Step A:

[1995]

[1996] Compound E2a (2.03 g, 10 mmol), Cu 2 O (0.288 g, 2 mmol), PEG (4.0), Cs 2 CO 3 (9.77 g, 30 mmol), a mixture of 4-methylimidazole (0.98 g, 12 mmol) and E2b (0.72 g, 3 mmol) in NMP (15 mL) was vacuumed at 120 °C in a sealed tube - Nitrogen exchange degassing and stirring for 48 hours. The mixture was cooled to room temperature and washed with CH 2 Cl 2 Dilute, then add silica gel. The mixture was stirred for 20 minutes and filtered. The organic layer was washed with water (3x), brine, washed over MgSO 4 Drying, and concentration gave crude product. The crude residue was purified by column chromatography with CH 2 Cl 2 Elution with / MeOH afforded compound E2c (0.2 g).

[1997] Step B:

[1998]

[1999] Compound E1h (0.141 mmol), E2c (28.8 mg, 0.141 mmol), potassium carbonate (0.117 g, 0.846 mmol) and CuBr.Me 2 A mixture of S (58 mg, 0.282 mmol) in pyridine (1.0 mL) was heated at 140°C overnight. The mixture was wash...

Embodiment 3

[2001]

[2002] Step A:

[2003]

[2004] To a solution of compound E1h (1 equiv) in THF was added 1 PrMgCl.LiCl (1M in THF, 1.3 equiv) and stir for 20 minutes. This was followed by the addition of methyl cyanoformate (1.0 equiv). The resulting mixture was stirred at room temperature for 2 h, after which it was washed with saturated aqueous NH 4 Cl diluted, will be extracted with EtOAc, will be dried (Na 2 SO 4 ), will be concentrated and will be purified by silica gel flash chromatography (Hex / EtOAc) to give compound E3a.

[2005] Step B:

[2006]

[2007] E3a will be hydrolyzed with LiOH in water / MeOH / THF to give E3b.

[2008] Step C:

[2009]

[2010] Compounds E1j (0.596mmol) and E3b (0.596mmol) will be mixed into DCM (4ml) at room temperature, which is then added with HOBT (96mg, 0.715mmol), EDC (136mg, 0.715mmol) and DIEA (300μl, 1.2mmol). The resulting mixture was continuously stirred at room temperature for 16 hours. The mixture will use CH 2 Cl ...

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PUM

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Abstract

This invention provides novel compounds that are modulators of gamma secretase. The compounds have the formula (I). Also disclosed are methods of modulating gamma secretase activity and methods of treating Alzheimer's disease using the compounds of formula (I).

Description

[0001] References to related applications [0002] This application claims the benefit of US Provisional Application Serial No. 61 / 012863, filed December 11, 2007. technical field [0003] The present invention relates to certain heterocyclic compounds that can be used as γ-secretase regulators (including inhibitors, antagonists, etc.), pharmaceutical compositions containing the compounds, and methods for using the compounds and compositions to treat various diseases, Such diseases include central nervous system disorders such as neurodegenerative diseases such as Alzheimer's disease and other diseases involving the deposition of amyloid proteins. It is especially useful for reducing the production of amyloid beta (hereinafter referred to as Aβ), which can effectively treat diseases caused by Aβ, such as Alzheimer's disease and Down syndrome (Down Syndrome). Background technique [0004] Alzheimer's disease is a disease characterized by neuronal degeneration and loss and al...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P25/00C07D455/02C07D498/04C07D487/04A61K31/4375C07D513/04
CPCC07D455/02A61P9/00A61P11/02A61P25/00A61P25/28A61P27/06
Inventor X·黄R·G·阿斯拉尼安A·帕拉尼
Owner SCHERING AG
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