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Triazole compounds as lipoxygenase inhibitors

A compound, optionally a technology, applied in the direction of anti-inflammatory agents, drug combinations, organic chemistry, etc., can solve problems that are not specifically disclosed

Inactive Publication Date: 2008-11-05
BIOLIPOX AB
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these documents do not specifically disclose 1(N)-unsubstituted 1,2,3-triazole-4-carboxylic acid amides

Method used

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  • Triazole compounds as lipoxygenase inhibitors
  • Triazole compounds as lipoxygenase inhibitors
  • Triazole compounds as lipoxygenase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 to 69

[0441] general steps

[0442] Method A

[0443]TBTU (1.1 mmol) was added to a solution of 1,2,3-triazole-4-carboxylic acid (113 mg, 1.0 mmol) and diisopropylethylamine (258 mg, 2 mmol) in anhydrous DMF (1 mL) and The mixture was stirred at room temperature for 10 min. The relevant arylamine (1.3 mmol) was added and the mixture was stirred at the indicated temperature for the indicated period. The resulting mixture was concentrated and water (20 mL) was added to the residue. The mixture was extracted with EtOAc (3 x 20 mL) and the combined extracts were washed with water (20 mL), dried (Na 2 SO 4 ) and concentrate. The residue was purified by chromatography (eluent EtOAc / heptane) to afford the title product.

[0444] Method B

[0445] 1,2,3-triazole-4-carboxylic acid (65 mg, 0.50 mmol), SOCl 2 (1 mL) and DMF (1 drop) was heated at 40 °C for 2 h. The mixture was concentrated and the residue was dried in vacuo. The resulting solid, DMAP (83mg, 0.68mmol) and the re...

Embodiment 70-78

[0469] general steps

[0470] (a) 3-[2-(Trimethylsilyl)ethoxymethyl]-1,2,3-triazole-4-carboxylic acid aryl-amide

[0471] Butyllithium (1.6M in hexane, 1.1 mL, 1.7 mmol) was added dropwise to 1-[2-(trimethylsilyl)ethoxymethyl]-1 cooled to -20 °C, 2,3-Triazole (3:1 mixture of isomers prepared as described above, 300 mg, 1.5 mmol) in THF (20 mL). The mixture was stirred at -20°C for 30 min and cooled to -78°C. A solution of the relevant aryl isocyanate (2.0 mmol) in THF (5 mL) was added dropwise and the mixture was stirred at -78 °C for 2 h, allowed to warm to room temperature, and then stirred at room temperature for 18 h. Add Et 2 O (20mL) and NH 4 Cl (aq, sat, 10 mL) and the layers were separated. Wash the aqueous phase with Et 2 O (2×20 mL) was extracted and the combined extracts were dried (Na 2 SO 4 ) and concentrate. The residue was purified by chromatography (eluent EtOAc / heptane) to afford the subtitled product (intermediate (a) 32 to 40) as a white or yell...

Embodiment 79-105

[0483] general steps

[0484] Butyllithium (1.6M in hexane, 900 μL, 1.5 mmol) in THF (12 mL) cooled to -50 °C was added dropwise to 1-[2-(trimethylsilyl)ethoxy A solution of methyl]-1,2,3-triazole (3:1 mixture of isomers, prepared as described above, 210 μL, 299 mg, 1.5 mmol). The mixture was stirred at -50°C for 30 min, cooled to -78°C and a solution of the relevant isocyanate (2 mmol) in THF (5 mL) was added dropwise. The mixture was stirred at -78 °C for 30 min, allowed to warm to room temperature and stirred at room temperature for 16 h. The mixture was cooled to 0 °C and HCl (10 mL of 0.27M in EtOH, 2.7 mmol) was added. After stirring at 0 °C for 4 h, the mixture was concentrated and the residue was purified by chromatography (eluent EtOAc / heptane, 20-60%) to afford the title product.

[0485] Table 5 - Examples (Ex.) 79 to 105

[0486] Ex.

[0487]

[0488]

[0489] Table 6 - Physical Properties of Examples 79-105

[0490] ...

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Abstract

There is provided compounds of formula (I) wherein W is an optionally substituted aryl or heteroaryl group, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of a lipoxygenase (e.g. 15- lipoxygenase) is desired and / or required, and particularly in the treatment of inflammation.

Description

field of invention [0001] The present invention relates to novel pharmaceutically useful compounds. The present invention also generally relates to compounds useful in the inhibition of 15-lipoxygenase activity and thus in the treatment of inflammatory diseases and inflammation. The invention also relates to the use of such compounds as medicines, to pharmaceutical compositions containing them, and to synthetic routes for their production. Background of the invention [0002] There are many diseases / conditions that are inflammatory in their nature. One of the major problems associated with existing treatments for inflammatory disorders is the lack of efficacy and / or the prevalence of side effects (real or perceived). [0003] Asthma is a chronic inflammatory disease affecting 6% to 8% of the adult population in industrialized societies. In children, the incidence is even higher, approaching 10% in most countries. Asthma is the most common cause of hospitalization in chil...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/04C07D401/12C07D403/12C07D417/12A61K31/4192A61P29/00
CPCC07D401/12C07D403/12C07D417/14C07D249/04A61P1/04A61P1/18A61P11/00A61P11/06A61P17/00A61P17/02A61P17/06A61P19/02A61P25/00A61P25/28A61P27/02A61P27/16A61P29/00A61P35/00A61P37/06A61P37/08A61P43/00A61P9/00A61P9/10A61P3/10A61K31/4192
Inventor 本亚明·佩尔克曼安德列·萨宁彼得·尼尔松哈塞·克罗曼
Owner BIOLIPOX AB
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