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Therapeutic agent for chronic obstructive pulmonary disease

A technology for chronic obstructive and pulmonary diseases, applied in allergic diseases, sensory diseases, respiratory diseases, etc., can solve the problems of different mechanisms of COPD activity and action, undisclosed prevention and/or treatment of COPD, etc.

Inactive Publication Date: 2008-04-23
SUMITOMO DAINIPPON PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] It has been reported in Patent Document 1 that a 5-membered ring compound is capable of suppressing a delayed asthmatic response, but there is no disclosure of an agent for the prevention and / or treatment of COPD, whose activity and mechanism of action are different from those of asthma

Method used

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  • Therapeutic agent for chronic obstructive pulmonary disease
  • Therapeutic agent for chronic obstructive pulmonary disease
  • Therapeutic agent for chronic obstructive pulmonary disease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0145] N-{2-[2-[(3-fluorophenyl)imino]-4-(4-morpholinophenyl)-thiazol-3(2H)-yl]ethyl}-N'-methyl Urea (SMP-028)

[0146]

[0147] (1) To a solution of tert-butyl 2-(aminoethyl)carbamate (1.02g) in acetonitrile (20ml) was added dropwise 3-fluorophenylisothiocyanate (752mg), and the mixture was heated at 75°C 1 hour. The reaction mixture was concentrated in vacuo and crystallized from n-hexanol to give tert-butyl 2-{[(3-fluoroanilino)thiocarbonyl]amino}ethylcarbamate (1.81 g)

[0148] 1 H-NMR (CDCl 3 ): δ1.35(9H, s), 3.35(2H, m), 3.74(2H, m), 4.89(1H, bs), 6.99(3H, m), 7.37(1H, m), 7.81(1H, bs)

[0149](2) Under a nitrogen atmosphere, stir and heat the tert-butyl 2-{[(3-fluoroanilino)thiocarbonyl]amino}ethylcarbamate (1.81g) obtained above at 45°C, α-bromo - A mixture of 4'-morpholino-acetophenone (1.56 g) and ethanol (20 ml). After 1 hour, the resulting crystals were filtered to give {2-[2-[(3-fluorophenyl)imino]-4-(4-morpholinophenyl)-thiazol-3(2H)-yl]ethyl } tert-But...

Embodiment 2

[0156] N-{2-[2-[(3-fluorophenyl)imino]-4-(4-morpholinophenyl)-thiazol-3(2H)-yl]ethyl}-N'-methyl Urea salt

[0157] (1) N-{2-[2-[(3-fluorophenyl)imino]-4-(4-morpholino-4-ylphenyl)-1,3-thiazole-3(2H)- Synthesis of ]ethyl}-N'-methylurea hydrobromide

[0158] To N-{2-[2-[(3-fluorophenyl)imino]-4-(4-morpholino-4-ylphenyl)-1,3-thiazol-3(2H)-yl] To a suspension of ethyl}-N'-methylurea (455 mg) in chloroform (50 ml) was added 25% HBr / AcOH (0.32 g), and the dissolved mixture was stirred for 30 minutes. Diethyl ether was added thereto after removal of the solvent, and the precipitate was filtered to obtain crystals (520 mg) with a melting point of 191-193°C.

[0159] (2) N-{2-[2-[(3-fluorophenyl)imino]-4-(4-morpholino-4-ylphenyl)-1,3-thiazole-3(2H)- Synthesis of ]ethyl}-N'-methylurea benzenesulfonate

[0160] Following the same procedure as the above method, benzenesulfonic acid (158 mg) was used to obtain crystals (610 mg) having a melting point of 153.5-156°C.

[0161] (3) N-{2-...

Embodiment 3

[0168] N-{2-[2-[(3-fluoro-4-hydroxyphenyl)imino]-4-(4-morpholinophenyl)-thiazol-3(2H)-yl]ethyl}-N '-methylurea

[0169]

[0170] (1) Phenyl chlorothionoformate was added to a toluene solution of 4-amino-2-fluorophenol, and 30 minutes later, 1N aqueous sodium hydroxide solution was added thereto. The mixture was stirred at room temperature for 3 hours, after which tert-butyl 2-(aminoethyl)carbamate was added and the mixture was stirred overnight to give 2-{[(3-fluoro-4-hydroxyanilino)thiocarbonyl ]Amino}ethylcarbamate tert-butyl ester.

[0171] (2) According to the steps similar to those in Example 1, use tert-butyl 2-{[(3-fluoro-4-hydroxyanilino)thiocarbonyl]amino}ethylcarbamate obtained in (1) above and α-bromo-4'-morpholino-acetophenone to give the title compound.

[0172] 1 H-NMR (DMSO-d6): δ2.46 (3H, d, J=4.7), 3.17-3.24 (6H, m), 3.72-3.76 (6H, m), 6.01 (1H, s), 6.63-6.66 (1H, m), 6.75-6.78 (1H, m), 6.87-6.93 (1H, m), 6.99 (2H, d, J=8.85) and 7.29 (2H, d, J=8.85). ...

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Abstract

Disclosed is a method for the prevention and / or treatment of a chronic obstructive pulmonary disease by administrating a 5-membered cyclic compound represented by the formula below or a pharmaceutically acceptable salt of the compound or a prodrug of the compound or salt: wherein X represents an oxygen or sulfur atom; R1 represents a hydrogen atom, a substituted or unsubstituted alkyl or the like; R2 represents a hydrogen atom, a substituted or unsubstituted alkyl or the like; Y1 represents a single bond, a substituted or unsubstituted alkylene or the like; the wavy line means an (E) or (Z) coordination; R3 represents a hydrogen atom, a substituted or unsubstituted aryl or the like; Y2 represents a substituted or unsubstituted alkylene or an alkenylene; R4 represents a hydrogen atom, a substituted or unsubstituted alkanoyl or the like; and R5 represents a hydrogen atom or a substituted or unsubstituted alkyl.

Description

technical field [0001] The present invention relates to the pharmaceutical use of the 5-membered ring compound described in WO02 / 02542 or a salt thereof or a pharmaceutical composition. More particularly, the present invention relates to a pharmaceutical use of a 5-membered ring compound or a salt thereof or a pharmaceutical composition for effectively preventing and / or treating chronic obstructive pulmonary disease (COPD). Background technique [0002] It has been reported in Patent Document 1 that a 5-membered ring compound is capable of suppressing a delayed asthmatic response, but there is no disclosure of an agent for the prevention and / or treatment of COPD, whose mechanism of activity and action is different from that of asthma. [0003] Chronic obstructive pulmonary disease is defined as a disease of airflow obstruction (obstructive ventilation disorder) caused by chronic bronchitis, emphysema or its complications, but in April 2001 the international guidelines GOLD (...

Claims

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Application Information

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IPC IPC(8): A61K31/5377A61K31/56A61K45/00A61P11/00C07D277/20C07D277/42
CPCA61K31/5377A61K31/56C07D277/42A61K9/10A61P11/00A61P11/02A61P11/06A61P27/16A61P37/08A61P43/00
Inventor 菅泽敏成中岛孝藤田一司金井利夫
Owner SUMITOMO DAINIPPON PHARMA CO LTD
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