Heterocyclic sulfonamide derivative and medicine containing same

A nitrogen heterocycle and pharmaceutical technology, applied in the field of novel heterocyclic sulfonamide compounds

Active Publication Date: 2018-09-28
EA PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, it has also been reported that formaldehyde-induced pain behavior disappears in TRPA1 knockout mice (Non-Patent Document 9)

Method used

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  • Heterocyclic sulfonamide derivative and medicine containing same
  • Heterocyclic sulfonamide derivative and medicine containing same
  • Heterocyclic sulfonamide derivative and medicine containing same

Examples

Experimental program
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Embodiment

[0722] Hereinafter, the present invention will be described in detail using reference examples, examples, and test examples, but the present invention is not limited to these. In addition, unless otherwise specified, the devices, reagents, and the like used in this example can be easily prepared according to methods generally practiced in the art, or can be purchased commercially. In addition, % of the title compound represents a yield.

[0723] The structural formulas and physical properties of the reference example compounds are shown in Table 2.

[0724] [table 2-1]

[0725]

[0726] [Table 2-2]

[0727]

[0728] [Table 2-3]

[0729]

[0730] [Table 2-4]

[0731]

[0732] [Table 2-5]

[0733]

reference example A-1

[0734] Reference Example A-1: ​​Synthesis of 5-fluorobenzofuran-2-ylsulfonyl chloride (A-1)

[0735] (Step 1) Synthesis of 2-(2,2-dibromovinyl)-4-fluorophenol

[0736] A solution of carbon tetrabromide (1.70kg, 5.14mol) in dichloromethane (80mL) was cooled to 0°C, triphenylphosphine (2.07kg, 7.91mol) was added, and stirred for 30 minutes. Triethylamine (1.30 kg, 12.8 mol) was added to the reaction mixture, and then 5-fluoro-2-hydroxybenzaldehyde (300 g, 2.14 mol) was added slowly while keeping the reaction temperature below 5°C. The reaction mixture was stirred at 30°C for 2 hours, then concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane / ethyl acetate) to obtain the title compound (300 g, 1.01 mol, 47%).

[0737] 1 H NMR (400MHz, CDCl 3 )δ7.54 (s, 1H), 7.35-7.32 (m, 1H), 6.95-6.90 (m, 1H), 6.79-6.75 (m, 1H), 5.41 (s, 1H).

[0738] (Step 2) Synthesis of 2-bromo-5-fluorobenzofuran

[0739] Tetrahydrofuran...

reference example A-2

[0745] Reference Example A-2: Synthesis of 4-fluorobenzofuran-2-ylsulfonyl chloride (A-2)

[0746] The title compound was obtained in the same manner as in Reference Example A-1, using 6-fluoro-2-hydroxybenzaldehyde instead of 5-fluoro-2-hydroxybenzaldehyde.

[0747] MS(ESI)m / z 235(M+H) +

[0748] 1 H NMR (400MHz, CDCl 3 ) δ 7.72 (s, 1H), 7.60-7.55 (m, 1H), 7.47 (d, J=8.8Hz, 1H), 7.12 (t, J=8.8Hz, 1H).

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Abstract

The purpose of the present invention is to provide a novel compound having TRPA1 antagonist activity, a medicine containing the compound, and a pharmaceutical agent applicable to prophylaxis or treatment of diseases associated with TRPA1 antagonists and TRPA1. This compound represented by formula (I): [in the formula, each symbol is as defined in the description] or a pharmaceutically acceptable salt thereof, and a medicine or the like containing the compound or a pharmaceutically acceptable salt thereof, have TRPA1 antagonist activity, and are applicable to prophylaxis or treatment of diseases associated with TRPA1 antagonists and TRPA1.

Description

technical field [0001] The present invention relates to a novel heterocyclic sulfonamide compound with transient receptor potential ankyrin 1 (Transient Receptor Potential Ankyrin 1, TRPA1) antagonistic activity and a pharmaceutical composition containing the compound, and may be used for the prevention or treatment of diseases related to TRPA1 medicine. Background technique [0002] Transient receptor potential ankyrin 1 (TRPA1) is a nonselective cation channel belonging to the transient receptor potential (TRP) channel superfamily. Like other TRP channel families, it has 6 transmembrane domains forming a tetramer composed of 4 subunits. TRPA1 is a ligand-dependent ion channel that undergoes structural changes through ligand binding. As a result, the channel opens, allowing cations such as calcium ions and sodium ions to flow into the cell, thereby regulating the membrane potential of the cell. As ligands of TRPA1, irritating natural substances (for example, allyl isothi...

Claims

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Application Information

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IPC IPC(8): C07D405/14A61K31/4439A61K31/506A61P1/04A61P1/18A61P3/10A61P11/06A61P11/08A61P11/14A61P17/04A61P19/02A61P25/00A61P25/04A61P29/00A61P37/08A61P43/00C07D403/12C07D409/14C07D491/048C07K14/705
CPCA61P25/00A61K31/4439A61K31/506C07D403/12C07D405/14C07D409/14C07D491/048C07K14/705C07D405/12
Inventor 小林香织铃木保奥住龙哉
Owner EA PHARMA CO LTD
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