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3-substituted carbonyl-naphtho[2,3-b]furane derivative or pharmaceutically acceptable salt thereof

A pharmacy and furan technology, applied in the field of pharmaceutical composition, can solve problems such as unexpected and tumor reduction

Inactive Publication Date: 2016-11-23
1GLOBE BIOMEDICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Conventional therapy targeting the common cancer cells that make up the majority of a tumor mass is expected to reduce tumor size but is not expected to have a meaningful survival effect unless it also targets CSCs

Method used

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  • 3-substituted carbonyl-naphtho[2,3-b]furane derivative or pharmaceutically acceptable salt thereof
  • 3-substituted carbonyl-naphtho[2,3-b]furane derivative or pharmaceutically acceptable salt thereof
  • 3-substituted carbonyl-naphtho[2,3-b]furane derivative or pharmaceutically acceptable salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0342] Methyl 2-(1,l-dimethoxyethyl)-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-3-carboxylate

[0343]

[0344] 2,3-dichloro-1,4-naphthoquinone (2.27g), 4,4-dimethoxy-3-oxopentanoic acid methyl ester (2.09g) and potassium carbonate (3.46g) in acetonitrile (100mL ) solution was heated and stirred at 90°C for 6 hours. The precipitated solid was filtered through celite with ethyl acetate. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate / chloroform) to obtain the title compound as a yellow solid (2.87 g).

[0345] MS(ESI+)313(M-OMe + )

Embodiment 2

[0347] Methyl 2-acetyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-3-carboxylate

[0348]

[0349] A solution of the compound of Example 1 (1.15 g) in formic acid (20 mL) was stirred at 25°C for 4 hours. The reaction solution was concentrated under reduced pressure, methanol (10 mL) was added thereto, and the mixture was stirred. The solid was collected on a filter to give the title compound (grey, 0.96g).

[0350] MS(ESI+)299(M + +1)

Embodiment 3

[0352] 2-Acetyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-3-carboxylic acid

[0353]

[0354] A solution of the compound of Example 2 (0.96 g) in a mixture of 4N HCl / 1,4-dioxane (10 mL) and conc. HCl (4 mL) was stirred at 120° C. for 9 hours. The reaction solution was concentrated under reduced pressure. To the residue was added saturated NaHCO 3 aqueous solution and ethyl acetate, and the mixture was extracted. The aqueous layer was acidified with HCl, then extracted with chloroform. The organic layer was washed with brine, washed with Na 2 SO 4 Dry and filter. The filtrate was concentrated under reduced pressure to obtain the title compound (grey, 0.44 g).

[0355] MS(ESI+)285(M + +1)

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Abstract

The present invention provides a compound of the following formula (1) or a pharmaceutically acceptable salt thereof, wherein X is an oxygen atom and the like; Y is -CO-, -S02-and the like; R1 is an optionally-substituted C1-6 alkyl group, an optionally-substituted C1-6 alkylcarbonyl group and the like; R2 is an optionally-substituted C1-6 alkyl group, an optionally-substituted C1-6 alkoxy group, an optionally-substituted amino group, an optionally-substituted 5-to 12-membered monocyclic or polycyclic saturated heterocyclic group and the like; R3, R4, R5, and R6 are independently a hydrogen atom and the like which exhibits excellent effects in suppressing the proliferation and sphere-forming ability of cancer cells, and can be useful as an antitumor drug or cell growth inhibitor.

Description

technical field [0001] The present invention relates to a 3-substituted carbonylnaphtho[2,3-b]furan derivative or a pharmaceutically acceptable salt thereof which can be used as medicine. Specifically, the present invention relates to a pharmaceutical composition comprising a 3-substituted carbonylnaphtho[2,3-b]furan derivative or a pharmaceutically acceptable salt thereof. The present invention also relates to a medicament comprising a 3-substituted carbonylnaphtho[2,3-b]furan derivative or a pharmaceutically acceptable salt thereof. Background technique [0002] Cancer is caused by genetic abnormalities caused by radiation, ultraviolet rays, carcinogens, viruses, etc. The number of deaths from cancer is increasing year by year, and cancer is now the number one cause of death in Japan. Methods for treating cancer include, for example, antitumor drugs, surgery, radiation therapy, and immunotherapy, among which treatment with antitumor drugs is most important as drug therap...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N47/10
CPCA61K31/343A61K31/443A61K31/497A61P35/00A61P35/02C07D307/92C07D405/04C07D405/12C07D413/06
Inventor 曾根敏彦W·广濑N·岛田C·J·李李微D·莱格特
Owner 1GLOBE BIOMEDICAL CO LTD
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