Nitrogen-containing aromatic ring derivatives containing galactose and uses thereof

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

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0160] Example 1 4-(3-chloro-4-(3-(4-(((2S,3R,4S,5R,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,3S,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,3S,4S,5R)-2-(Acetoxymethyl)-6-hydroxytetrahydro-2H-pyran-3,4,5-triyltriacetate (3.6g, 10.3mmol) , trichloroacetonitrile (10.4mL, 104mmol), 4A molecular sieves (3g) and dichloromethane (30mL) were added to a 100mL single-necked round bottom flask, stirred in an ice bath under nitrogen protection for 0.5 hours, and then DBU (0.32mL, 2.1mmol ), stirred and reacted in an ice bath for 0.5 hours; 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 a whit...

Embodiment 2

[0187] Example 2 4-(3-chloro-4-(3-(3-fluoro-4-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl Synthesis of base)tetrahydro-2H-pyran-2-yl)oxy)phenyl)urea)phenoxy)-7-methoxyquinoline-6-carboxamide

[0188]

[0189] Step 1) (2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(2-fluoro-4-nitrophenoxy)tetrahydro-2H-pyridine Synthesis of pyran-3,4,5-triyltriacetate

[0190]

[0191] The title compound of this step was prepared by referring to the method described in step 2 of Example 1, that is, (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2,2,2-trichloro -1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate (1.82g, 3.69mmol), 2-fluoro-4-nitrophenol (1.16g, 7.38mmol), 4A molecular sieve (5g) and boron trifluoride diethyl ether (0.57mL, 4.4mmol) were prepared by reacting in dichloromethane (20mL), and the crude product was separated and purified by silica gel column chromatography (petroleum ether / ethyl acetate ( v / v)=3 / 1) Purification gave the title compound as a light yellow solid (1...

Embodiment 3

[0211] Example 3 4-(3-chloro-4-(3-(3-chloro-4-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl Synthesis of base)tetrahydro-2H-pyran-2-yl)oxy)phenyl)urea)phenoxy)-7-methoxyquinoline-6-carboxamide

[0212]

[0213] Step 1) (2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(2-chloro-4-nitrophenoxy)tetrahydro-2H-pyridine Synthesis of pyran-3,4,5-triyltriacetate

[0214]

[0215] The title compound of this step was prepared by referring to the method described in step 2 of Example 1, that is, (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2,2,2-trichloro -1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate (1.72g, 3.49mmol), 2-chloro-4-nitrophenol (0.73g, 4.2mmol), 4A molecular sieve (5g) and boron trifluoride diethyl ether (0.54mL, 4.2mmol) were prepared by reacting in dichloromethane (20mL), and the crude product was separated and purified by silica gel column chromatography (petroleum ether / ethyl acetate ( v / v)=3 / 1) afforded the title compound as a white solid (1.16 g, 65.8%).

...

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Abstract

The invention belongs to the technical field of medicines, and relates to nitrogen-containing aromatic ring derivatives containing galactose 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 medicines, and relates to a nitrogen-containing aromatic ring derivative containing galactose, a pharmaceutical composition, and a use method and application thereof. Specifically, the present invention relates to nitrogen-containing aromatic ring derivatives containing galactose 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 chara...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/203C07H15/26A61K31/706A61P35/00A61P37/06A61P35/02A61P29/00A61P19/02A61P11/06A61P17/06A61P7/06
CPCC07H15/203C07H15/26A61P35/00A61P37/06A61P35/02A61P29/00A61P19/02A61P11/06A61P17/06A61P7/06
Inventor 金传飞钟文和张英俊
Owner SUNSHINE LAKE PHARM CO LTD
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