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New tricyclic quinone derivative

Inactive Publication Date: 2017-01-19
BOSTON BIOMEDICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent describes compounds that can stop the growth of cancer cells and their ability to form spheres. These compounds can be used as medication to prevent or treat cancer.

Problems solved by technology

Therefore, many antitumor agents act on not only on cancer cells, but also on normal cells, and consequently any types of side effects develop.
However, with regard to molecular targeting agents, although previous side effects are reduced, there are problems that new side effects are exhibited and alternatives of pharmaceutical agents are limited.
Although the aforementioned antitumor agents were clinically used for the purpose of cancer therapy and prolonging the life of a cancer patients, there are still a number of unsolved problems including problems of side effects and the like as described above.
Although Conventional therapy that targets normal cancer cells accounting for most part of tumor lumps can reduce the size of a tumor, as long as a CSC is also targeted at the same time, a meaningful survival effect cannot be expected.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

reference example 1

methyl 4,7-dimethoxy-1-benzothiophene-2-carboxylate

[0204]

[0205]To a solution of 3,6-dimethoxy-2-nitrobenzaldehyde (70.0 g) in DMF (420 mL) was added dropwise methyl mercaptoacetate (33.4 mL) at room temperature. Subsequently, potassium carbonate (137 g) was added thereto in 10 parts, and then at unchanged constant temperature the reaction mixture was stirred for 1 hour. Methyl iodide (41.3 mL) was added dropwise thereto, followed by stirring for another 1 hour. The insoluble substance was removed through Celite, and then solvent was evaporated off. The resulting residue was dissolved in ethyl acetate (700 mL), washed with water (2×700 mL) and saturated brine (700 mL), and then dried over sodium sulfate. The solvent was then evaporated off to yield a standard compound as a flesh-colored powder (81.1 g).

[0206]1H-NMR (CDCl3, δ ppm): 8.04 (1H, s), 7.04 (1H, d, J=8.4 Hz), 6.90 (1H, d, J=8.4 Hz), 3.92 (3H, s), 3.89 (3H, s), 3.88 (3H, s) MS (ESI+) 253 (M++1).

reference example 2

methyl 5-amino-4,7-dimethoxy-1-benzothiophene-2-carboxylate (2A)

reference example 3

methyl 6-amino-4,7-dimethoxy-1-benzothiophene-2-carboxylate (2B)

[0207]

[0208]To a solution of methyl 4,7-dimethoxy-1-benzothiophene-2-carboxylate (2.04 g) (which was obtained in Reference example 1) in acetic acid (102 mL) was added dropwise 70% aqueous nitric acid solution (512 μL), and then the reaction mixture was stirred at 70° C. for 1 hour. After it was returned to room temperature, the reaction solution was poured into iced water, and then extracted with chloroform two times. The resulting organic layer was washed with saturated brine, and then dried over sodium sulfate. The solvent was then evaporated off to yield a mixture of 1A and 1B (2.57 g). This was used in the next reaction without further purification.

[0209]To a suspension of 90% reduced iron (2.68 g) and ammonium chloride (555 mg) in methanol / water (57.6 mL / 28.8 mL), which had been heated and stirred at 75° C., was added dropwise a suspension of the obtained mixture of 1A and 1B (2.57 g) in methanol (8.65 mL), and th...

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PUM

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Abstract

This invention provides a compound represented by formula (1) or a pharmaceutically acceptable salt thereof. Specifically, the present invention provides a compound represented by formula (1) or a pharmaceutically acceptable salt thereof [Therein, A is O, S, or N—R6; ring G is a 5-membered or 6-membered aromatic ring, etc., including 1-3 heteroatoms selected from O, S and N as constituent atoms; R1 and R2 are each independently a hydrogen atom, a halogen atom, or an optionally-substituted C1-6 alkyl carbonyl group, etc.; R3, R4 and R5 are each independently a hydrogen atom, a halogen atom, or an optionally-substituted C1-6 alkyl carbonyl group, etc.; and R6 is a hydrogen atom or an optionally-substituted C1-6 alkyl group, etc.].

Description

TECHNICAL FIELD[0001]The present invention relates to novel tricyclic quinone derivatives useful as medicament or a pharmacologically acceptable salt thereof. More particularly, the invention relates to pharmaceutical compositions comprising a novel tricyclic quinone derivative or a pharmacologically acceptable salt thereof. The invention relates to therapeutic agents comprising a novel tricyclic quinone derivative comprising the compound, or a pharmacologically acceptable salt thereof.BACKGROUND ART[0002]Cancer develops when abnormality in gene occurs by an action of radiation, ultra violet rays, carcinogen, virus, or the like. The number of deaths by cancer increases year by year, and cancer is currently the top cause of death in Japan. As means for such cancer therapy, antitumor agents, surgical operation, radiotherapy, immunotherapy, and the like are performed. However, among these, the therapeutic use of an antitumor agent is the most important as an internally therapeutic mean...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D491/048
CPCC07D491/048C07D495/04C07D471/04A61P35/00A61P35/02A61K31/381A61K31/4355A61K31/4365A61K31/5377
Inventor BAN, HITOSHIKAMIOKA, SEIJIRI, SHOUKOUFURUTA, TOMOYUKIKITANO, HIROYUKILI, CHIANG JIA
Owner BOSTON BIOMEDICAL
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