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Condensed ring compound and use thereof

A technology of compounds and cyclic groups, which is applied in the field of fused ring compounds and their applications, and can solve problems such as the unclarified function and role of cysLT2 receptors

Inactive Publication Date: 2006-10-11
ONO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in pathological conditions cysLT 2 The function and role of the receptor have not been elucidated

Method used

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  • Condensed ring compound and use thereof
  • Condensed ring compound and use thereof
  • Condensed ring compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0559] The invention is illustrated by the following non-limiting examples and biological examples.

[0560] Solvents in parentheses in chromatographic separation and TLC represent eluents or developing solvents, and the ratios of solvents used in chromatographic separation and TLC are volume ratios. NMR indicates 1 Solvents in parentheses in H-NMR and NMR represent solvents used in the measurement. TFA stands for trifluoroacetic acid.

[0561] The nomenclature of the present invention is according to ACD / Name (trade name; Advanced Chemistry Development Inc.), which generates IUPAC rule nomenclature.

Embodiment 1

[0562] Example 1: 2-(phenylmethyloxy)-3-nitrobenzoic acid

[0563] Add benzyl bromide (50.0 mL) and potassium carbonate (66.3 g) to a solution of 2-hydroxy-3-nitrobenzoic acid (36.6 g) in N, N-dimethylformamide (500 mL), and the mixture is heated at 60° C. After stirring overnight, the reaction mixture was poured into water, the resulting mixture was extracted with a mixture of ethyl acetate and n-hexane (1:1), the organic layer was dried with water, saturated brine, anhydrous sodium sulfate and concentrated, and the residue was dissolved in In a mixture of tetrahydrofuran (100 mL) and methanol (200 mL), the resulting mixture was stirred at 50°C for 30 minutes, the reaction mixture was concentrated, the residue was acidified with 2N hydrochloric acid, extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and anhydrous After drying over sodium sulfate and concentrating, the residue was recrystallized from isopropanol (50 mL) / n-hexane (200 mL...

Embodiment 2

[0565]Example 2: tert-butyl (2-(phenylmethyloxy)-3-nitrophenyl)carbamate

[0566] At room temperature, diphenylphosphoryl azide (24.9 mL) was added dropwise to a solution of the compound (30.0 g) prepared in Example 1 and triethylamine (16.2 mL) in toluene (440 mL), and the reaction mixture was stirred at 80° C. for 2 hours, tert-butanol (52.6 mL) was added to the reaction mixture, the mixture was stirred at 80°C for 3 hours, the reaction mixture was cooled to room temperature, washed successively with water, 0.1N hydrochloric acid, water, saturated aqueous sodium bicarbonate and saturated brine, After drying over sodium sulfate and concentration, the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1) to obtain the title compound (32.98 g) having the following physical data.

[0567] TLC: Rf 0.40 (n-hexane:ethyl acetate=9:1).

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PUM

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Abstract

The present invention relates to a compound of formula (I) (wherein all symbols have the same meanings as described hereinbefore). The compound antagonizes cysLT 2 and therefore, it is useful as an agent for the prevention and / or treatment of respiratory diseases such as bronchial asthma, bronchial asthma, chronic obstructive pulmonary disease, pneumonectasia, chronic bronchitis, pneumonia (e.g. interstitial pneumonitis etc.), severe acute respiratory syndrome (SARS), acute respiratory distress syndrome (ARDS), allergic rhinitis, sinusitis (e.g. acute sinusitis, chronic sinusitis, etc.), and the like, or as an expectorant or antitussives.

Description

technical field [0001] The present invention relates to: [0002] (1) compounds represented by the following formula (I), [0003] [0004] where all symbols have the same meaning as described below, and [0005] (2) cysLT comprising the compound shown in formula (I) 2 receptor antagonists. Background technique [0006] Bronchial asthma is a pathological condition in which the airways are narrowed due to airway constriction and inflammation, causing paroxysmal coughing, wheezing and dyspnea. Therapeutic drugs include inhaled steroid drugs with strong anti-inflammatory effects, β-stimulant drugs and theophylline as bronchodilators, anti-allergic drugs that inhibit transmitters, and the like. [0007] Various chemical transmitters are known to be involved in bronchial asthma, among which cysteinyl leukotrienes (cysLTs) are known to constrict airways about 1000 times more than histamine. In addition, cysLTs contribute to the induction of airway inflammation, typically i...

Claims

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Application Information

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IPC IPC(8): C07D265/36C07D413/04C07D413/10C07D417/04A61K31/538A61K45/00A61P11/00A61P11/06A61P43/00
Inventor 竹内淳板谷敏中山孝介辰巳正高桥真也藤田学
Owner ONO PHARMA
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