Triazine compounds and pharmaceutical use thereof

a technology of triazine and compound, applied in the field of triazine compound, can solve the problems of side effects of nsaid, increase the risk of stomach perforation, bleeding and the like, and disrupt the balance, and achieve the effect of suppressing pge2 production

Inactive Publication Date: 2015-09-24
JAPAN TOBACCO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The new chemical compound described in this patent can be used to treat various conditions such as pain, inflammation, fever, joint disorders, high blood pressure, eye diseases, brain damage, and even some types of cancer. It works by reducing the levels of an important substance called PGF2.

Problems solved by technology

The patent text describes a new compound that can inhibit the growth and metastasis of cancer cells. The compound was developed by studying the mechanism of action of a protein called mPGES-1, which is involved in the production of a lipid called PGE2 that inhibits the growth and metastasis of cancer cells. The text also mentions that the compound can be used as a therapeutic drug for the treatment of pain, inflammation, and other diseases associated with inflammation. The patent text also describes the use of the compound in animal models to evaluate the effectiveness of the new compound. The technical problem addressed by the patent text is the development of a new compound that can inhibit the growth and metastasis of cancer cells.

Method used

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  • Triazine compounds and pharmaceutical use thereof
  • Triazine compounds and pharmaceutical use thereof
  • Triazine compounds and pharmaceutical use thereof

Examples

Experimental program
Comparison scheme
Effect test

production example 1

Synthesis of N-(4-chloro-3-{4-[4-(2,2-dimethylpropoxyl)phenyl]-6-hydroxy-1,3,5-triazin-2-yl}benzyl)-3,3,3-trifluoro-2,2-dimethylpropionamide (Example No. 1-86)

[0584]

(1) 2-chloro-4-[4-(2,2-dimethylpropoxyl)phenyl]-6-methoxy-1,3,5-triazine

[0585]

[0586]Under an argon atmosphere, a suspension of 4-(2,2-dimethylpropoxyl)phenylboronic acid (2.0 g, 9.6 mmol), 2,4-dichloro-6-methoxy-1,3,5-triazine (3.5 g, 19 mmol), [1,1′-bis(diphenylphosphino) ferrocene]palladium(II)dichloride dichloromethane adduct (1.1 g, 0.96 mmol) and 2M aqueous sodium carbonate solution (14 ml, 29 mmol) in toluene (20 ml) was stirred at 100° C. for 3.5 hr. At room temperature, to the reaction mixture were added water and ethyl acetate and the mixture was partitioned. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, washed with saturated brine, dried over sodium sulfate, filtered to remove sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column ...

production example 2

Synthesis of 1-[4-chloro-3-(4-hydroxy-6-phenyl-1,3,5-triazin-2-yl)-benzyl]-3,3-dimethyl-1,3-dihydroindol-2-one (Example No. 1-258)

[0603]

(1) 2-(5-bromomethyl-2-chlorophenyl)-4-methoxy-6-phenyl-1,3,5-triazine

[0604]

[0605]By a method similar to that in Production Example 1 (1) and (2), and using 2,4-dichloro-6-methoxy-1,3,5-triazine, 2-chloro-5-hydroxymethylphenylboronic acid, and phenylboronic acid instead of 4-(2,2-dimethylpropoxyl)phenylboronic acid, [4-chloro-3-(4-methoxy-6-phenyl-1,3,5-triazin-2-yl)phenyl]methanol was obtained.

[0606]Under an argon atmosphere, to a solution of the obtained [4-chloro-3-(4-methoxy-6-phenyl-1,3,5-triazin-2-yl)phenyl]methanol (0.47 g, 1.4 mmol) and triphenylphosphine (0.56 g, 2.1 mmol) in chloroform (4.5 ml) was added carbon tetrabromide (0.71 g, 2.1 mmol) under ice-cooling. The reaction mixture was stirred at room temperature for 10 min, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hex...

production example 3

Synthesis of N-[4-chloro-3-(4-hydroxy-6-phenyl-1,3,5-triazin-2-yl)benzyl]-N-ethyl-3,3,3-trifluoro-2,2-dimethylpropionamide (Example No. 1-263)

[0614]

(1) [4-chloro-3-(4-methoxy-6-phenyl-1,3,5-triazin-2-yl)benzyl]ethylamine

[0615]

[0616]Under an argon atmosphere, to 2-(5-bromomethyl-2-chlorophenyl)-4-methoxy-6-phenyl-1,3,5-triazine (0.20 g, 0.51 mmol) obtained in the same manner as in Production Example 2 (1) was added a solution of 2M ethylamine tetrahydrofuran (2.5 ml) at room temperature, and the mixture was stirred for 1 hr. To the reaction mixture were added saturated aqueous sodium hydrogen carbonate and ethyl acetate and the mixture was partitioned. The organic layer was washed with saturated brine, dried over sodium sulfate, filtered to remove sodium sulfate, and concentrated under reduced pressure to give the title compound (0.28 g) as a crude product.

[0617]1H-NMR (400 MHz, CDCl3) δ: 1.14 (3H, t, J=7.2 Hz), 2.70 (2H, q, J=7.2 Hz), 3.86 (2H, s), 4.22 (3H, s), 7.44 (1H, dd, J=8.2,...

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Abstract

Provided is a compound having an mPGES-1 inhibitory activity and useful for the prophylaxis or treatment of pain, rheumatism, osteoarthritis, fever, Alzheimer's disease, multiple sclerosis, arteriosclerosis, glaucoma, ocular hypertension, ischemic retinal disease, systemic scleroderma and cancer including colorectal cancer.
A compound represented by the formula [I] or a pharmaceutically acceptable salt thereof:
wherein each symbol is as defined in the SPECIFICATION.

Description

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Claims

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Application Information

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Owner JAPAN TOBACCO INC
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