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Compound used as DOR receptor antagonist

A technology of compounds and receptors, applied in the field of compounds, can solve problems that cannot greatly improve memory or effectively cure

Inactive Publication Date: 2015-08-19
苏州远智医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs can only reduce the deterioration of clinical symptoms of moderate to severe Alzheimer's disease to a certain extent, but cannot greatly improve memory or effectively cure them, and the market demand is far from being met

Method used

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  • Compound used as DOR receptor antagonist
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  • Compound used as DOR receptor antagonist

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Compound 1

[0105] N,N-Diethyl-4-(2-(((2-(trifluoromethyl)benzyl)amino)methyl)-1H-indene-3-position)benzamide

[0106]

[0107] Intermediate 1-1: 3-Chloro-1H-indene-2-carbaldehyde

[0108]

[0109] Cool 4mL of phosphorus oxychloride to 0°C, add DMF (800mg, 11mmol), stir for 30min, add 1-indanone (1.32g, 10mmol), stir the reaction system at room temperature for 2h, then heat to 70°C to clarify. After cooling to room temperature, the reactant was poured into 50 g of crushed ice, extracted with EA (50 mL*3), and the organic layer was washed with water (100 mL*2), saturated sodium bicarbonate (100 mL), and saturated sodium chloride (100 mL). Concentration gave a crude product, which was purified by column chromatography (EA:PE=1:30) to give Intermediate 1-1 as a pale yellow solid (750 mg, 42%).

[0110] Intermediate 1-2: N,N-Diethyl-4-(2-formaldehyde-1H-indene-3-position)benzamide

[0111]

[0112]Compound 1-1 (400mg, 2.25mmol), boroester 1-2 (1.10g, 3.63mmol)...

Embodiment 2

[0118] Compound 2

[0119] N,N-Diethyl-4-(5-hydroxy-2-(((2-(trifluoromethyl)benzyl)amino)methyl)-1H-indene-3-position)benzamide

[0120]

[0121] Intermediate 2-2: 3-Chloro-5-methoxy-1H-indene-2-carbaldehyde

[0122]

[0123] Add 1ml of phosphorus oxychloride to a 25ml single-necked bottle, seal it tightly, and place it in an ice-water bath to cool to 0°C. Inject DMF (216mg, 2.96mmol) with a syringe and stir for 20min. 2-1 (400mg, 2.47mmol) was added to the above system and replaced with nitrogen 3 times. After stirring at room temperature for 3 hours, TLC showed that a small amount of compound 1 was not converted. Pour the system into 20ml of ice water to quench, add 50ml of EA, separate the layers, extract the aqueous layer with 50ml of EA, combine the organic layers, wash once with saturated NaCl, and then wash with anhydrous sulfuric acid Sodium-dried, dried, and purified by column chromatography, intermediate 2-2 (150 mg, 29.2%) was obtained.

[0124] Intermedia...

Embodiment 3

[0135] Compound 3

[0136] N,N-Diethyl-4-(2-(((2-fluorophenethyl)amino)methyl)-5-hydroxy-1H-indene-3-position)benzamide

[0137]

[0138] Compound 3 can be prepared by replacing 2-trifluoromethylphenethylamine with 2-fluorophenethylamine according to the method for preparing compound 2.

[0139] 1 H NMR (400MHz, CDCl 3 )δ7.39(d, J=8.0Hz, 2H), 7.24-7.11(m, 5H), 7.04-6.96(m, 2H), 6.67(dd, J1=8.0Hz, J2=2.0Hz, 1H), 6.61(d,J=2.0Hz,1H),3.67(s,2H),3.57(m,2H),3.47(s,2H),3.31(m,2H),2.87-2.81(m,4H),1.27 -1.23(m,3H),1.19-1.14(m,3H); ESI-MS m / z 459.5(M+H) + .

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PUM

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Abstract

The invention provides a compound used as a DOR receptor antagonist. The structural formula of the compound is as shown in the specification. In comparison with the prior art, the invention expounds a pharmaceutical composition and a preparation containing the compound and an application of the DOR antagonist. The compound can be separately used as a medicine or can be used along with other compounds so as to treat AD (Alzheimer's disease).

Description

technical field [0001] The present invention relates to a compound, a method for preparing the compound, a pharmaceutical composition and a medicament of the compound, and the compound is used for treating, preventing, and diagnosing one or more diseases or symptoms related to Alzheimer's disease. Background technique [0002] The Diagnostic and Statistical Manual of the American Psychiatric Association defines dementia as an organic mental disorder characterized by widespread intellectual loss. AD (Alzheimer's disease) is the most common dementia, accounting for more than 50% of typical late-onset dementias. [0003] As of 2009, there are about 129 million people over 60 years old in my country, accounting for 10.15% of the total population, which makes my country enter an aging society ahead of schedule. In my country, senile dementia mostly occurs in the elderly over the age of 65, accounting for about 4% to 5%, about 10% over the age of 75, and about 20% over the age of...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C237/30C07C237/48C07C237/32C07C213/02C07C215/50C07C235/46C07D307/81C07D335/02C07D207/14C07D217/04C07D295/155C07D277/28C07D309/04C07D333/20C07D213/36C07D213/38C07D311/58C07D295/13C07D213/81C07D213/74C07D211/14C07D211/46C07D309/08C07D223/16C07D267/10C07D417/12C07D407/12C07D313/08C07D405/06C07D405/04A61K31/166A61K31/343A61K31/443A61K31/382A61K31/40A61K31/472A61K31/495A61K31/426A61K31/351A61K31/381A61K31/4402A61K31/4418A61K31/137A61K31/352A61K31/5375A61K31/4409A61K31/496A61K31/4453A61K31/451A61K31/445A61K31/55A61K31/553A61K31/427A61K31/335A61K31/4427A61P25/28
Inventor 李本赵简裴钢陈力江涛翟培彬孙利
Owner 苏州远智医药科技有限公司
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