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2-Methyl-3-aryloxy-3-heteroarylpropylamine compounds and application

A compound, methyl technology, applied in the field of medicinal chemistry, can solve the problems of no obvious effect on cognitive impairment and low cure rate, and achieve the effect of improving cognition and minor acute toxicity

Active Publication Date: 2017-01-25
NHWA PHARMA CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It shows a low cure rate (less than 60%), and has a better effect on mood disorders, but has little obvious effect on cognitive impairment accompanied by depression

Method used

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  • 2-Methyl-3-aryloxy-3-heteroarylpropylamine compounds and application
  • 2-Methyl-3-aryloxy-3-heteroarylpropylamine compounds and application
  • 2-Methyl-3-aryloxy-3-heteroarylpropylamine compounds and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1 Preparation of 2-propionylthiophene

[0060] Propionic acid (10.0g, 135mmol), thiophene (17.0g, 202mmol) and phosphoric acid (5mL) were mixed and stirred at room temperature, and trifluoroacetic anhydride (56.7g, 270mmol) was slowly added dropwise under ice-cooling. After about 1 hour of the dropwise addition, Remove the ice and stir in the bathroom for 1 hour, add water (100 mL) after cooling, extract with dichloromethane (4-5 times), wash the organic phase with sodium hydroxide (10%) (to slightly alkaline), wash with water, and dry (anhydrous sulfuric acid Magnesium), concentrated to obtain a brown-yellow liquid. It was directly put into the next reaction without further purification.

Embodiment 2

[0061] Example 2 Preparation of 3-dimethylamine-2-methyl-1-(thiophen-2-yl)propan-1-one

[0062] 2-propionylthiophene (12.0g, 85.6mmol), dimethylamine hydrochloride (14.0g, 170mmol) and paraformaldehyde (7.7g, 256mmol) were dissolved in isopropanol (100mL), and concentrated hydrochloric acid (2mL ), the reaction solution was concentrated under reduced pressure after reflux for 24h, and water (200mL) was added, and the unreacted raw materials and impurities were removed after the aqueous phase was extracted with ether, the aqueous layer was adjusted to alkaline with sodium hydroxide (10%), extracted with ethyl acetate, Dry and concentrate to obtain a light yellow liquid, which is directly put into the next reaction without further purification.

Embodiment 3

[0063] Example 3 Preparation of 3-dimethylamino-2-methyl-1-(thiophen-2-yl)propan-1-ol

[0064] 3-Dimethylamine-2-methyl-1-(thiophen-2-yl)propan-1-one (16.9g, 85.6mmol) was dissolved in methanol (100mL), and sodium borohydride (3.9 g, 102.8 mmol), and stirred at the same temperature for 1 h after the addition, the reaction solution was concentrated under reduced pressure, added water, extracted with dichloromethane, dried, and concentrated to obtain 7.8 g of yellow oil. Quantitative yield.

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Abstract

The invention relates to 2-methyl-3-aryloxy-3-heteroarylpropylamine compounds and their pharmaceutical application. It is discovered via experiments that these compounds are KCNQ2 / 3 channel blockers, having good anti-depression activity, capable of improving cognitive function and having low acute toxicity.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a 2-methyl-3-aryloxy-3-heteroarylpropylamine compound and an application thereof. Background technique [0002] Depression is a common mental illness. Its core symptoms include mood disorders (depressed mood, anhedonia, pessimistic world-weariness) and cognitive impairment associated with depression. It has the characteristics of high recurrence rate, high suicide rate, and high disability rate. , with the increasing social pressure, the incidence rate gradually increased. The research on antidepressants began in the 1960s. Monoamine oxidase inhibitors and tricyclic antidepressants were the first to be used. In addition to inhibiting the reuptake of monoamine transmitters, these drugs also inhibit the histamine receptors, Cholinergic receptors and adrenergic receptors have high affinity, and have many adverse reactions and poor tolerance. The antidepressants common...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/20C07D307/52A61K31/381A61K31/341A61P25/24A61P25/28
CPCC07D307/52C07D333/20
Inventor 徐祥清郭强赵松邱印利刘志强司崇静
Owner NHWA PHARMA CORPORATION
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