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N-substituted benzothiophenesulfonamide derivatives

A technology of benzothiazole and derivatives, which is applied in the field of chymotrypsin inhibitors, can solve the problem of no chymotrypsin inhibitors being found, and achieve the effect of strong inhibitory activity

Inactive Publication Date: 2003-11-26
TOAEIYO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, until now, no clinically applicable chymotrypsin inhibitors have been found

Method used

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  • N-substituted benzothiophenesulfonamide derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Methyl 4-(5-chloro-3-methylbenzo[b]thiophen-2-sulfonylamino)-3-methanesulfonylbenzoate

[0064] In a mixed solvent of 20 mL of THF and 3 mL of DMF, 985 mg of methyl 4-amino-3-methanesulfonyl benzoate was dissolved, and then 170 mg of sodium hydride (oily, 60%) was added at 0°C. After stirring at this temperature for 20 minutes, 1.28 g of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene was added at 0°C, followed by stirring at room temperature for 1 hour. Furthermore, 150 mg of sodium hydride (oily, 60%) was added at room temperature, and then the mixture was stirred at this temperature for 2 hours. After confirming the disappearance of the reactant, saturated ammonium chloride aqueous solution was added at 0°C to terminate the reaction, and then extraction was performed with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation, and the residue was purified by silica gel chr...

Embodiment 2

[0069] Ethyl 4-(5-chloro-3-methylbenzo[b]thiophene-2-sulfonylamino)-3-methanesulfonylbenzoate

[0070] In the same manner as in Example 1, 559 mg of ethyl 4-amino-3-methanesulfonylbenzoate was used to obtain 529 mg of the title compound as a colorless powder.

[0071] Melting point: 167-169°C

[0072] 1 H-NMR(CDCl 3 ): δ 1.36 (3H, t, J = 7.1 Hz), 2.70 (3H, s), 3.06 (3H, s), 4.36 (2H, q, J = 7.1 Hz), 7.47 (1H, dd, J = 2.0, 8.8 Hz), 7.74 (1H, d, J = 8.8 Hz), 7.78 (1H, d, J = 2.0 Hz), 7.86 (1H, d, J = 8.8 Hz), 8.19 (1H, dd, J = 2.0, 8.8 Hz), 8.50 (1H, d, J=2.0 Hz), 9.83 (1H, brs).

[0073] IRν max (KBr): 3224, 2985, 1716, 1608, 1500, 1358, 1300, 1142cm -1 .

Embodiment 3

[0075] Tert-Butyl 4-(5-chloro-3-methylbenzo[b]thiophen-2-sulfonamido)-3-methanesulfonylbenzoate

[0076] According to the same method as in Example 1, 128 mg of tert-butyl 4-amino-3-methanesulfonylbenzoate was used to obtain 148 mg of the title compound as a colorless powder.

[0077] Melting point: 236-238°C

[0078] 1 H-NMR(CDCl 3 ): δ 1.54 (9H, s), 2.52 (3H, s), 3.28 (3H, s), 7.55-7.80 (4H, m), 8.00 (1H, s), 8.25-8.30 (1H, m).

[0079] IRν max (KBr): 3467, 2974, 2327, 1705, 1662, 1597, 1477, 1396, 1296, 1130, 1099cm -1 .

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Abstract

The present invention relates to an N-substituted benzothiophenesulfonamide derivative or a salt thereof and applications thereof. Furthermore, it provides an agent for preventing or treating cardiac or circulatory disease caused by abnormal increase of production of angiotensin II or endothelin I based on chymase activity, wherein the agent has a selective inhibitory action on chymase.

Description

Technical field [0001] The present invention relates to a medicament, particularly an N-substituted benzothiazole sulfonamide derivative or a salt thereof capable of selectively inhibiting chymotrypsin, and to a chymotrypsin inhibitor containing the above-mentioned active ingredient. Because these compounds have a selective inhibitory effect on chymotrypsin, they can be used as agents for the prevention and treatment of the following diseases: Angiotensin II (hereinafter referred to as AngII) or endothelin I (hereinafter referred to as ET-1) based on chymotrypsin activity Hypertension, cardiac hypertrophy, heart failure, myocardial infarction, arteriosclerosis, diabetic or non-diabetic kidney disease, diabetic retinopathy, and percutaneous transluminal coronary angioplasty (hereinafter referred to as PTCA) caused by abnormal increase in Restenosis, intimal hypertrophy after bypass transplantation, ischemic reperfusion disorder, chronic rheumatism, keloids, psoriasis, allergies, in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/381A61K31/4025A61K31/4178A61K31/422A61K31/427A61P9/10A61P43/00C07D333/62C07D409/12C07D413/12C07D417/12
CPCA61K31/381A61K31/422C07D333/62C07D409/12A61K31/427C07D417/12C07D413/12A61K31/4025A61K31/4178A61P43/00A61P9/08A61P9/10
Inventor 佐藤正次山田秀宜风山真一森田孝博正木秀和高桥敦男龙井晃长谷川健志
Owner TOAEIYO
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