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Aminopyridine compound

A technology of aminopyridine and compounds, applied in the field of new aminopyridine compounds, can solve the problems of no specific disclosure, etc., and achieve the effect of excellent toxicity

Inactive Publication Date: 2012-09-12
UBE IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the above-mentioned documents, the compound of the present invention refers to a sulfonamide having an aromatic ring group substituted with a specific substituent or a 5-6 membered ring heteroaromatic ring group, and pyridylaminoacetic acid and its ester as partial structures. Compounds, none of which are specifically disclosed

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0776] (6-{[5-(1,1-dimethylpentyl)thiophen-2-ylmethyl](pyridin-3-ylsulfonyl base)aminomethyl}pyridin-2-ylamino)acetic acid (Exemplary Compound No. 673)

[0777] 1-(a): [tert-butoxycarbonyl (6-{[5-(1,1-dimethylpentyl)thiophene-2- Methyl](pyridin-3-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]tert-butyl acetate

[0778](tert-butoxycarbonyl {6-[(pyridin-3-ylsulfonyl) aminomethyl] pyridin-2-yl} amino) tert-butyl acetate obtained in the same manner as Reference Example 1-(f) Add 1.27g (6.00mmol) of [5-(1,1-dimethylpentyl)thiophen-2-yl]methanol obtained in Reference Example 4-(c) to 4.0ml of tetrahydrofuran solution of 422mg (0.880mmol), 395 µl (1.60 mol) of tri-n-butylphosphine and 276 mg (1.60 mmol) of N,N,N',N'-tetramethylazodicarbonamide were stirred at room temperature for 16 hours. After completion of the reaction, water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride sol...

Embodiment 2

[0787] (6-{[5-(1,1-dimethylpentyl)thiophen-2-ylmethyl](pyridin-2-ylsulfonyl base)aminomethyl}pyridin-2-ylamino)acetic acid (Exemplary Compound No. 666)

[0788] 2-(a): [tert-butoxycarbonyl (6-{[5-(1,1-dimethylpentyl)thiophene-2- Methyl](pyridin-2-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]tert-butyl acetate

[0789] 3.16 g (6.60 mmol) tetrahydrofuran 30ml solution, add 1.27g (6.00mmol) of [5-(1,1-dimethylpentyl)thiophen-2-yl]methanol obtained in Reference Example 4-(c), three-n- - 2.96ml (12.0mol) of butylphosphine and 2.07g (12.0mmol) of N,N,N',N'-tetramethylazodicarbonamide, stirred at room temperature for 16 hours. After completion of the reaction, water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (elution solvent; toluen...

Embodiment 3

[0798] (6-{(4-fluorobenzenesulfonyl)[5-(1,1-dimethylpentyl)thiophen-2-ylmethyl] Aminomethyl}pyridin-2-ylamino)acetic acid (Exemplary Compound No. 642)

[0799] 3-(a): [tert-butoxycarbonyl (6-{(4-fluorobenzenesulfonyl)[5-(1,1-dimethyl ylpentyl)thiophen-2-ylmethyl]aminomethyl}pyridin-2-yl)amino]tert-butyl acetate

[0800] 436 mg (0.880 mmol) of (tert-butoxycarbonyl {6-[(4-fluorobenzenesulfonyl) aminomethyl] pyridin-2-yl} amino) tert-butyl acetate obtained in Reference Example 3 in 4.0 ml of tetrahydrofuran Add 170mg (0.800mmol) of [5-(1,1-dimethylpentyl)thiophen-2-yl]methanol and 395μl of tri-n-butylphosphine (1.60 mol) and N, N, N', N'-tetramethyl azodicarbonamide 276 mg (1.60 mmol), stirred at room temperature for 16 hours. After completion of the reaction, water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated und...

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PUM

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Abstract

A compound represented by general formula (I) or a pharmacologically acceptable salt thereof, a medicinal composition comprising the same, and a medicinal composition for the treatment or prevention of respiratory diseases or glaucoma.

Description

technical field [0001] The present invention relates to a novel aminopyridine compound or a pharmacologically acceptable salt thereof which can be used as medicine. In more detail, the aminopyridine compound related to the present invention can be used as a therapeutic agent for respiratory diseases such as asthma and chronic obstructive pulmonary disease (hereinafter abbreviated as COPD) or eye diseases (especially glaucoma) due to its EP2 agonist effect. Therapeutic and / or prophylactic use. Background technique [0002] Prostaglandin E administered by inhalation was reported in asthmatic patients 2 (hereinafter abbreviated as PGE 2 ) suppress immediate and delayed asthmatic responses (refer to Non-Patent Document 1). In addition, known PGE 2 It acts as an agonist on receptors such as EP1, EP2, EP3, and EP4, and among them, it has been pointed out that the agonist action on the EP2 receptor is closely related to the bronchodilation effect (see Non-Patent Document 2). ...

Claims

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Application Information

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IPC IPC(8): C07D213/74A61K31/44A61K31/4427A61K31/4436A61K31/4439A61K31/444A61P11/00A61P11/06A61P11/08A61P27/06A61P43/00C07D401/12C07D405/12C07D409/12C07D409/14C07D417/12
CPCA61P11/00A61P11/06A61P11/08A61P27/06A61P43/00C07D213/74C07D401/12C07D405/12C07D409/12C07D409/14C07D417/12A61K31/4436
Inventor 岩村亮田中正幸胜部哲嗣柴川信彦重富学冈成荣治神田智子德永裕仁藤原宽
Owner UBE IND LTD
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