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Glucose-containing nitrogen-containing aromatic ring derivative and application thereof

A technology of nitrogen oxides and compounds, applied to nitrogen-containing aromatic ring derivatives and pharmaceutical compositions, preparation of such compounds and pharmaceutical compositions, nitrogen-containing aromatic ring derivatives and pharmaceutical compositions thereof, diseases, prevention or treatment of tumors field

Active Publication Date: 2021-06-04
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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  • Glucose-containing nitrogen-containing aromatic ring derivative and application thereof
  • Glucose-containing nitrogen-containing aromatic ring derivative and application thereof
  • Glucose-containing nitrogen-containing aromatic ring derivative and application 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-trihydroxyl-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 (4.0g, 11.5mmol) , trichloroacetonitrile (11.5mL, 115mmol), 4A molecular sieves (5g) and dichloromethane (80mL) were added to a 250mL single-necked round bottom flask, stirred in an ice bath under nitrogen protection for 1 hour, and then DBU (0.35mL, 2.3mmol ), stirred and reacted in an ice bath for 1 hour; the reaction was stopped, filtered, and the filtrate was collected 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 ...

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 base)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 pyran-3,4,5-triyltriacetate

[0189]

[0190] The title compound of this step was prepared by referring to the method described in step 2 of Example 1, that is, (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2,2,2-trichloro -1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate (1.0g, 2.03mmol), 2-fluoro-4-nitro-phenol (382mg, 2.43mmol), 4A molecular sieve (1.2g) and boron trifluoride diethyl 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) afforded the title compound as a white solid (0.65 g, 65.7%)....

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 base)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 pyran-3,4,5-triyltriacetate

[0212]

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

[0...

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Abstract

The invention belongs to the technical field of medicines, and relates to a glucose-containing nitrogen-containing aromatic ring derivative and application thereof, and a pharmaceutical composition containing the compound. The invention also relates to a method for preparing the compound and pharmaceutical composition, and application of the compound and pharmaceutical composition in preventing or treating tumors, inflammatory diseases, autoimmune diseases and other diseases, especially tumors.

Description

technical field [0001] The invention belongs to the technical field of medicines, and relates to a nitrogen-containing aromatic ring derivative containing glucose, a pharmaceutical composition, and a use method and application thereof. Specifically, the present invention relates to nitrogen-containing aromatic ring derivatives containing glucose and pharmaceutical compositions thereof, methods for preparing such compounds and pharmaceutical compositions, and their use in the prevention or treatment of tumors, inflammatory disorders, autoimmune disease and other diseases. 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 malignant tumors originating from epithelial tissue, and is the most common type of malignant tumors. Generally speaking, "cancer" generally refers to all malignant tumors. Cancer has biological character...

Claims

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Application Information

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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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