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Polycyclic acid compounds useful as crth2 antagonists and antiallergic agents

A compound, C2-C6 technology, applied in the field of therapeutic agents for inflammatory diseases, can solve problems such as not mentioned

Inactive Publication Date: 2010-01-27
ASTELLAS PHARMA INC
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

However, none of these publications mention or suggest allergic reactions

Method used

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  • Polycyclic acid compounds useful as crth2 antagonists and antiallergic agents
  • Polycyclic acid compounds useful as crth2 antagonists and antiallergic agents
  • Polycyclic acid compounds useful as crth2 antagonists and antiallergic agents

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0268] To a solution of 5-(diphenylmethyl)-1-ethoxycarbonylmethyl-2(1H)-pyridone (565 mg) in EtOH was added dropwise 1M aqueous NaOH (4.9 mL) at room temperature, and the mixture was stirred at room temperature. The mixture was left for 1 hour. The resulting mixture was diluted with water (25 mL) and acidified with 1M aqueous HCl (10 mL). The precipitate was collected by filtration and washed with water (10 mL) to obtain 5-(diphenylmethyl)-1-carboxymethyl-2(1H)-pyridone (472 mg) as colorless crystals.

[0269] MS (ESI, m / z): 320 (M+H) + .

preparation example 2

[0271] To a solution of (2E,2′E)-3,3′-(1,3-phenylene)diethylacrylate (27.9 g) in a mixture of EtOH (300 mL) and THF (200 mL) at 0° C. 1M NaOH aqueous solution (92 mL) was added. The reaction mixture was stirred at the same temperature for 5 hours. The organic solvent of the reaction mixture was evaporated in vacuo and the obtained liquid was washed with EtOAc. The aqueous layer was neutralized with 1M aqueous HCl (92 mL), and the precipitate was collected by filtration. The precipitate was recrystallized twice from EtOH-water to obtain (2E)-3-{3-[(1E)-3-ethoxy-3-oxopropyl-1-en-1-yl]phenyl} Acrylic acid (10.5 g) as colorless crystals.

[0272] MS (ESI, m / z): 245 (M-H) - .

preparation example 3

[0274] To a suspension of LiH (45.6 mg) in DMF (6.0 mL) was added portionwise 5-(diphenylmethyl)-2(1H)-pyridone (500 mg) at room temperature, and the mixture was stirred at the same temperature for 15 min. To this mixture was added ethyl bromoacetate (255 μL) dropwise. The mixture was stirred at room temperature for 14 hours. The reaction was quenched with 1M aqueous HCl (10.0 mL), and the mixture was extracted with EtOAc (30 mL). The organic layer was sequentially washed with saturated NaHCO 3 aqueous and brine washes with anhydrous MgSO 4 Dry, vacuum filter and evaporate. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=3:2) to obtain 5-(diphenylmethyl)-1-ethoxycarbonylmethyl-2(1H)-pyridone (574 mg) as Colorless amorphous substance.

[0275] 1 H-NMR (CDCl 3 )δ: 1.27 (3H, t, J = 7.2Hz), 4.21 (2H, q, J = 7.2Hz), 4.53 (2H, s), 5.26 (1H, s), 6.55 (1H, d, J = 9.1 Hz), 6.67 (1H, d, J=1.8Hz), 7.10-7.17 (4H, m), 7.19-7.38 (7H, m).

[0276] MS (ES...

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Abstract

The present invention relates to a novel compound or a salt thereof, which is useful as a CRTH2 antagonist, especially as a medicament for disorder that participates eosinophil, for example, allergic disorder such as asthma, allergic rhinitis, allergic dermatitis, conjunctival inflammation, hives, eosinophilic bronchitis, food allergy, inflammation of the nasal sinuses, multiple sclerosis, angiitis, or chronic obstructive pulmonary disease (COPD) and the like.

Description

technical field [0001] The present application relates to novel compounds and medicaments containing the compounds as active ingredients, more particularly, the present application relates to therapeutic agents for inflammatory diseases. Background technique [0002] Mast cells, known as conductive cells in allergic inflammation, can be activated by various stimuli including antigens and produce various inflammatory mediators. [0003] Prostaglandin D 2 (PGD 2 ) is an important prostaglandin compound produced by activated mast cells. Some reports indicate that antigen challenge is in the airways of asthmatic patients (New England Journal of Medicine, 1986, 315(13), pp.800-804), in the nasal mucosa of allergic rhinitis patients or in the skin of allergic dermatitis patients (Journal of Immunology, 1991, 146 (2), pp.671-676) induce a large amount of PGD 2 . [0004] Fujitani et al. reported that overexpression of PGD synthase in transgenic mice (where PGD 2 Increased pro...

Claims

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Application Information

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IPC IPC(8): C07D213/64C07D401/06C07D209/08C07D209/42C07D401/12C07C233/20C07C233/60C07C233/73C07C233/18C07D213/81C07D413/04C07D237/14C07D213/82C07D213/56A61K31/4412A61P37/08
CPCC07D213/56C07D237/14C07D413/14C07D235/08C07C2101/08C07D401/06C07C271/50C07D237/04C07D401/10C07C233/73C07D413/04C07D213/64C07D213/81C07D211/76C07C233/18C07D409/10C07D263/38C07D213/82C07D209/24C07D263/22C07D277/34C07D405/04C07D209/08C07C233/60C07D401/12C07D333/38C07D209/14C07D213/80C07C233/20C07D209/42C07C2601/08A61P11/00A61P11/02A61P11/06A61P17/00A61P27/02A61P37/08A61P43/00A61K31/4412
Inventor 寺坂忠嗣善光龙哉林田久松田博佐藤淳司今村佳正长田宏关规夫天田由幸田崎调武田全弘田渕精一郎安田实椿一典
Owner ASTELLAS PHARMA INC
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