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Nitrogen-containing aromatic ring derivatives containing glucose and uses thereof

A technology of medicines and compounds, applied in the fields of diseases, nitrogen-containing aromatic ring derivatives and pharmaceutical compositions, preparation of such compounds and pharmaceutical compositions, prevention or treatment of tumors, nitrogen-containing aromatic ring derivatives and pharmaceutical compositions

Active Publication Date: 2022-04-29
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nitrogen-containing aromatic ring derivatives containing glucose have unexpectedly excellent antitumor activity, and its structure and activity have not been reported so far

Method used

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  • Nitrogen-containing aromatic ring derivatives containing glucose and uses thereof
  • Nitrogen-containing aromatic ring derivatives containing glucose and uses thereof
  • Nitrogen-containing aromatic ring derivatives containing glucose and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0160] Example 1 4-(3-Chloro-4-(3-(4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro Synthesis of -2H-pyran-2-yl)oxy)phenyl)urea)phenoxy)-7-methoxyquinoline-6-carboxamide

[0161]

[0162] Step 1) (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetra Synthesis of Hydrogen-2H-pyran-3,4,5-triyltriacetate

[0163]

[0164] (2R,3R,4S,5R)-2-(acetoxymethyl)-6-hydroxytetrahydro-2H-pyran-3,4,5-triyltriacetate (4.0 g, 11.5 mmol) , trichloroacetonitrile (11.5mL, 115mmol), 4A molecular sieves (5g) and dichloromethane (80mL) were added to a 250mL single-neck round-bottomed flask, stirred in an ice bath under nitrogen protection for 1 hour, and then added DBU (0.35mL, 2.3mmol) ), stirred the reaction under ice bath for 1 hour; stopped the reaction, filtered, collected the filtrate and spin-dried under reduced pressure, separated and purified by column chromatography (petroleum ether / ethyl acetate (v / v)=4 / 1) to obtain the title compound as pale...

Embodiment 2

[0186]Example 2 4-(3-Chloro-4-(3-(3-Fluoro-4-((((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl) Synthesis of tetrahydro-2H-pyran-2-yl)oxy)phenyl)urea)phenoxy)-7-methoxyquinoline-6-carboxamide

[0187]

[0188] Step 1) (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(2-fluoro-4-nitrophenoxy)tetrahydro-2H-pyridine Synthesis of Furan-3,4,5-triyltriacetate

[0189]

[0190] The title compound in this step was prepared according to the method described in Example 1, Step 2, namely (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2,2,2-trichloro) -1-Imineethoxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate (1.0 g, 2.03 mmol), 2-fluoro-4-nitro-phenol (382 mg, 2.43mmol), 4A molecular sieves (1.2g) and boron trifluoride ether (0.316mL, 2.43mmol) were prepared by reacting in dichloromethane (16mL), and the crude product was separated and purified by silica gel column chromatography (petroleum ether / ethyl acetate) (v / v)=2 / 1) to give the title compound as a white solid (0.65 g, 65.7%).

[0191] MS...

Embodiment 3

[0209] Example 3 4-(3-Chloro-4-(3-(3-Chloro-4-((((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl) Synthesis of tetrahydro-2H-pyran-2-yl)oxy)phenyl)urea)phenoxy)-7-methoxyquinoline-6-carboxamide

[0210]

[0211] Step 1) (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(2-chloro-4-nitrophenoxy)tetrahydro-2H-pyridine Synthesis of Furan-3,4,5-triyltriacetate

[0212]

[0213] The title compound in this step was prepared according to the method described in Example 1, Step 2, namely (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2,2,2-trichloro) -1-Imineethoxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate (1.5g, 3.04mmol), 2-chloro-4-nitro-phenol (634mg, 2.43 mmol), 4A molecular sieves (1.5 g) and boron trifluoride ether (0.475 mL, 3.66 mmol) were prepared by reaction in dichloromethane (24 mL), and the crude product was subjected to silica gel column chromatography (petroleum ether / ethyl acetate (v / v)=2 / 1) Purification gave the title compound as a white solid (1.0 g, 65.2%).

[0214] MS(...

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Abstract

The invention belongs to the technical field of medicines, and relates to nitrogen-containing aromatic ring derivatives containing glucose and uses thereof, as well as pharmaceutical compositions containing the compounds. The present invention also relates to methods for preparing such compounds and pharmaceutical compositions, and their use in the prevention or treatment of tumors, inflammatory disorders, autoimmune diseases and other diseases, especially tumors.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a nitrogen-containing aromatic ring derivative and a pharmaceutical composition containing glucose, and a method and application thereof. In particular, the present invention relates to nitrogen-containing aromatic ring derivatives containing glucose and pharmaceutical compositions thereof, and also to methods for preparing such compounds and pharmaceutical compositions, and their use in the prevention or treatment of tumors, inflammatory disorders, autoimmunity diseases, etc. In particular, the compounds of the present invention and their pharmaceutical compositions are used for the prevention or treatment of tumors. Background technique [0002] In medicine, cancer refers to a malignant tumor originating from epithelial tissue, and is the most common type of malignant tumor. Generally speaking, "cancer" is used to refer to all malignant tumors. Cancer has biological character...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/26C07H1/00A61K31/7036A61P35/00A61P37/02A61P35/02A61P29/00A61P19/02
CPCC07H15/26C07H1/00A61P35/00A61P37/02A61P35/02A61P29/00A61P19/02
Inventor 金传飞钟文和许腾飞
Owner SUNSHINE LAKE PHARM CO LTD
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