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2-(Substituted phenyl)-4,4,5,5-tetramethyl-1-hydroxy-imidazoline, its synthesis, activity and application

A technology of tetramethylimidazoline and hydroxyl group, which is applied in the application field of preparing antithrombotic drugs, thrombolytic drugs and drugs for treating ischemic stroke

Active Publication Date: 2019-02-22
北京恒润泰生医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the instability of 1,3-dioximidazoline requires stabilization

Method used

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  • 2-(Substituted phenyl)-4,4,5,5-tetramethyl-1-hydroxy-imidazoline, its synthesis, activity and application
  • 2-(Substituted phenyl)-4,4,5,5-tetramethyl-1-hydroxy-imidazoline, its synthesis, activity and application
  • 2-(Substituted phenyl)-4,4,5,5-tetramethyl-1-hydroxy-imidazoline, its synthesis, activity and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 prepares 2,3-dimethyl-2,3-dinitrobutane

[0023] Add 130mL of 6N NaOH solution to 69.0g (0.78mol, 70mL) of 2-nitropropane successively under ice bath and stirring, 20mL (0.38mol, slowly dropwise, within 1 hour) of Br 2 and 240 mL of ethanol. The reaction compound was refluxed at 90°C for 3 hours, during which a flaky precipitate appeared. The reaction solution was poured into 800mL of ice water while it was hot, and 49.0g (73%) of the title compound was obtained by filtration as colorless flaky crystals. ESI-MS(m / e):177[M+H] + .

Embodiment 2

[0024] Embodiment 2 prepares 2,3-dimethyl-2,3-dihydroxyaminobutane

[0025] 7.00g (40mmol) 2,3-dimethyl-2,3-dinitrobutane and 4.00g NH 4 Dissolve Cl in 80 mL of 50% aqueous ethanol, stir under ice bath, and add 16.00 g of zinc powder in batches within 3 hours. After the zinc powder was added, the reaction mixture was stirred at room temperature for 3 h, filtered with suction, and the filter cake was repeatedly washed with 50% aqueous ethanol. Combine the filtrate and washing liquid, adjust the pH to 2 with concentrated hydrochloric acid, and concentrate under reduced pressure to obtain a slurry. Dissolve the slurry with a small amount of 50% ethanol aqueous solution, add an appropriate amount of potassium carbonate, mix well, put it into a Soxhlet extractor, use dichloromethane as the extractant, extract at 60°C for 6 hours, concentrate the extract under reduced pressure, and use the residue Trituration with petroleum ether gave 2.07 g (35%) of the title compound as a colorl...

Embodiment 3

[0026] Example 3 Preparation of 2-(3-carboxy-4-hydroxyphenyl)-1,3-dihydroxy-4,4,5,5-tetramethylimidazole

[0027] Dissolve 1.48g (10mmol) of 2,3-dimethyl-2,3-dihydroxyaminobutane in a small amount of methanol at room temperature, add 2.0g (12mmol) of 3-carboxy-4-hydroxybenzaldehyde, and react for 12 hours. Filtration afforded 2.07 g (70%) of the title compound as a colorless powder. ESI-MS(m / e):298[M+H] + .

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Abstract

The invention discloses 1-hydroxy-2-[3-(formyl-Gly)-4-(oxyacetyl-Ala) phenyl]-4,4,5,5-tetramethyl imidazoline, a preparation method thereof, antithrombotic activity thereof, thrombolytic activity thereof, and an effect thereof for treating mice suffering from cerebral ischemia. Furthermore, the invention discloses an application of 1-hydroxy-2-[3-(formyl-Gly)-4-(oxyacetyl-Ala) phenyl]-4,4,5,5-tetramethyl imidazoline to preparation of antithrombotic medicaments, thrombolytic medicaments and ischemic-stroke-treating medicaments.

Description

technical field [0001] The present invention relates to 1-hydroxy-2-[3-(formyl-Gly)-4-(oxyacetyl-Ala)phenyl]-4,4,5,5-tetramethylimidazoline and its preparation method , relating to its antithrombotic activity, relating to its thrombolytic activity, relating to its effect in treating cerebral ischemia rats, and thus the present invention relates to its application in the preparation of antithrombotic drugs, thrombolytic drugs and drugs for treating ischemic stroke . Background technique [0002] Ischemic stroke is a relatively common and serious cerebrovascular disease, characterized by high incidence, high mortality, high disability rate and high recurrence rate. At present, the clinical treatment of ischemic stroke faces the reality that there is no effective drug, especially for patients with stroke lasting more than 4 hours, either dying or being disabled. It is an important clinical need to invent drugs that are effective for patients with a stroke of more than 4 hours...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/26A61K31/4164A61P7/02A61P9/10
CPCC07D233/26
Inventor 彭师奇赵明彭莉
Owner 北京恒润泰生医药科技有限公司