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Micromolecule phentriazine dioxin-like compound and medicine by taking compound as active ingredient

A benzotriazine and compound technology, applied in the field of small-molecule benzotriazine compounds and medicines using the compound as an active ingredient, can solve problems such as high price and retinal detachment, and achieve the effect of improving safety

Inactive Publication Date: 2010-01-06
JIANGSU DAYUAN BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the above two drugs must be administered by intravitreal injection, which has certain treatment risks, especially the risk of endophthalmitis (bacterial infection in the eye) and retinal detachment that may be caused by intraocular injection.
And it is very expensive because of its polymer structure

Method used

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  • Micromolecule phentriazine dioxin-like compound and medicine by taking compound as active ingredient
  • Micromolecule phentriazine dioxin-like compound and medicine by taking compound as active ingredient
  • Micromolecule phentriazine dioxin-like compound and medicine by taking compound as active ingredient

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of Compound I

[0046] 1. Weigh 10.5g (66.2mmol) of 2-methyl-5-nitro-aniline and place it in a single-necked bottle, add 150ml of CCl4, stir to dissolve, then add 15.6g (831.5mmo) of NBS under ice bath, After the dropwise addition was completed, the ice bath was removed, heated to reflux for 3.5 hours, cooled to room temperature instantly, filtered, and the filter cake was washed three times with 12ml of water and dried to obtain 24.3g of a yellow solid with a yield of 92%.

[0047] 2. Take by weighing 10.2g (41.2mmol) of the compound of the previous step reaction, dissolve it in 20ml of glacial acetic acid, heat to reflux, then add dropwise the hydrochloric acid solution of 6.8g (320mmol) of aminoacetonitrile in the reaction solution, and the dropwise addition is completed Afterwards, the temperature was maintained at 120 degrees for overnight reaction. The reaction solution was cooled, and the pH was adjusted to 12 with a strong base, then the mixture was r...

Embodiment 2

[0055] Synthesis of Compound II

[0056] 1. Weigh 10g (65mmol) of 2-methyl-5-nitro-aniline and place it in a single-necked bottle, add 150ml of CCl4, stir to dissolve, then add 14.6g (81.5mmo) of NBS under ice bath, drop After completion, the ice bath was removed, heated to reflux for 3.5 hours, cooled to room temperature instantly, filtered, and the filter cake was washed three times with 10 ml of water and dried to obtain 23.2 g of a yellow solid with a yield of 90%.

[0057] 2. Take by weighing 9.2g (40mmol) of the compound of the previous step reaction, dissolve it in 20ml of glacial acetic acid, heat to reflux, then add dropwise the hydrochloric acid solution of 6.8g (320mmol) of aminoacetonitrile in the reaction solution, after the dropwise addition , the temperature was maintained at 120 degrees overnight. The reaction solution was cooled, and the pH was adjusted to 12 with a strong base, then the mixture was refluxed for 2 hours, filtered, and the cake was passed thro...

Embodiment 3

[0065] Synthesis of compound III

[0066] Take 5.08g of compound-2, dissolve it in 20ml of THF, add 1ml of triethylamine, stir to dissolve, add dropwise the HTH solution of benzoyl chloride to the reaction solution. The reaction was carried out at room temperature for 3.5 hours, followed by TLC until the reaction was complete. Add 15ml of water to the reaction solution, extract with ethyl acetate, wash the organic phase 3 times with saturated sodium bicarbonate (3*20ml), wash with saturated brine, and dry over anhydrous sodium sulfate. Purification on a silica gel column yielded 7.09 g of a yellow solid. The yield was 88%.

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Abstract

The invention relates to a novel micromolecule phentriazine dioxin-like compound and a medicine by taking compound as active ingredient, and the application of the compound which is used as endothelial growth factor inhibitors for treating fundus oculi maculopathy. The micromolecule phentriazine dioxin-like compound is expressed by a general formula (A) or a general formula (B). The compound is used as an active ingredient of the medicine, can selectively block one group of kinase of vascular endothelial growth factor, and performs important functions of treating macular degeneration such as retina effusion, angiogenesis and inflammation mediated by the vascular endothelial growth factor ; in addition, the medicine can be designed into a drug administration way that eye medicine is dropped in eye, thereby improving the safety, convenience and universality of medicine usage.

Description

technical field [0001] The invention relates to a novel benzotriazine compound, a pharmaceutical composition containing the compound as an active ingredient, and their application as an endothelial growth factor inhibitor in the treatment of fundus diseases caused by neovascularization. Background technique [0002] Fundus diseases caused by new blood vessels, including age-related macular degeneration, myopic macular degeneration and macular edema caused by diabetes, are one of the diseases with the highest incidence in the world. Studies have found that vascular growth factor (VEGF, vascular Endothelial growth factor) is a common pathogenic factor that causes macular degeneration to worsen. In age-related macular degeneration and myopic macular degeneration, it can promote the growth and leakage of new blood vessels, and it is also an important factor that causes macular edema in diabetes and vaso-occlusive retinopathy. In response to this pathogenic mechanism, the medica...

Claims

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Application Information

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IPC IPC(8): C07D253/10C07D401/12A61K31/53A61P27/02
CPCC07D403/12A61P27/02
Inventor 胡颖健冯仲英张飞王红韩丽
Owner JIANGSU DAYUAN BIOTECH
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