Medical application of 2-(trifluoromethyl)benzenesulfonamide derivatives

A use and pharmaceutical technology, applied in the field of medical use of 2-trifluoromethylbenzenesulfonamide derivatives, can solve problems such as unreported

Active Publication Date: 2019-01-22
ZHEJIANG HISUN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, JP02001483A discloses a series of 2-trifluoromethylbenzenesulfonamide derivatives, which are used in agricultural fungicides, but are used in the preparation of drugs that inhibit URAT1, or in the preparation of treatments and / or preventions of abnormal uric acid levels. Use in medicines for characteristic disorders has not been reported

Method used

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  • Medical application of 2-(trifluoromethyl)benzenesulfonamide derivatives
  • Medical application of 2-(trifluoromethyl)benzenesulfonamide derivatives
  • Medical application of 2-(trifluoromethyl)benzenesulfonamide derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] Compound 2-amino-6-cyanobenzothiazole 1-A (700mg, 4mmol) was dissolved in 7ml of anhydrous THF, cooled to about -20°C, and LDA / THF solution (4.8mL, 1mmol / ml, 1.2eq), after the addition, continue to stir at this temperature for 0.5h, add 2-trifluoromethylbenzene-1sulfonyl chloride (1.17g, 4.8mmol, 1.2eq), after the addition, continue to stir at 0°C for 2 hours . Extracted with ethyl acetate, the crude product was separated and purified by silica gel column chromatography, the eluent was petroleum ether: ethyl acetate (V / V) = 1:3, to obtain compound 1 (1.2 g, yield 82%).

[0031] MS m / z(ESI):384[M+1]; 1 HNMR (400MHz, d-DMSO) 13.9 (s, br, 1H), 8.27-8.35 (m, 2H), 7.83-7.97 (m, 4H), 7.43 (d, J=7.2Hz, 1H).

Embodiment 2

[0033]

[0034] The compound 2-amino-6-cyanobenzoxazole 2-A (636mg, 4mmol) was dissolved in 7ml of anhydrous THF, cooled to about -20°C, and LDA / THF solution (4.8mL, 1mmol / ml , 1.2eq), continue stirring at this temperature for 0.5h after addition, add 2-trifluoromethylbenzene-1sulfonyl chloride (1.17g, 4.8mmol, 1.2eq), continue stirring at 0°C for 2 Hour. Extracted with ethyl acetate, the crude product was separated and purified by silica gel column chromatography, the eluent was petroleum ether:ethyl acetate (V / V)=1:3, to obtain compound 2 (1.15g, yield 78%).

[0035] MS m / z(ESI):368[M+1]; 1 HNMR (400MHz, d-DMSO) 8.34 (d, J = 8.0Hz, 1H), 8.10 (s, 1H), 7.96 (d, J = 8.0Hz, 1H), 7.82-7.91 (m, 2H), 7.74 ( d,J=8.0Hz,1H),7.43(d,J=8.0Hz,1H).

Embodiment 3

[0037]

[0038] The compound 2-amino-4-methyl-6-cyanobenzothiazole 3-A (756mg, 4mmol) was dissolved in 8ml of anhydrous THF, cooled to about -20°C, and LDA / THF solution (4.8mL , 1mmol / ml, 1.2eq), after the addition, continue to stir at this temperature for 0.5h, add 2-trifluoromethylbenzene-1 sulfonyl chloride (1.17g, 4.8mmol, 1.2eq), after the addition, at 0 ℃ Stirring was continued for 2 hours. Extracted with ethyl acetate, the crude product was separated and purified by silica gel column chromatography, the eluent was petroleum ether:ethyl acetate (V / V)=1:2, to obtain compound 3 (1.25g, yield 79%).

[0039] MS m / z(ESI):398[M+1]; 1 HNMR (400MHz, d-DMSO) 13.76 (s, br, 1H), 8.28 (d, J = 8.0Hz, 1H), 8.20 (s, 1H), 7.99 (d, J = 8.0Hz, 1H), 7.86- 7.91(m,2H),7.70(s,1H),2.43(s,3H).

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PUM

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Abstract

The invention relates to the field of medicines related to hyperuricemia and gout and specifically to the application of 2-(trifluoromethyl)benzenesulfonamide derivatives as URAT1 inhibitors, particularly as therapeutic agents for diseases associated with the abnormal levels of uric acid. The 2-(trifluoromethyl)benzenesulfonamide derivatives of the invention are compounds as shown in a formula (I)which is described in the specification. In the formula (I), R1 and X are as defined in the claims of the specification.

Description

technical field [0001] The invention relates to the field of drugs related to the treatment of hyperuricemia and gout. Specifically, it relates to a medical application of 2-trifluoromethylbenzenesulfonamide derivatives. Background technique [0002] Gout is a chronic metabolic disease characterized by hyperuricemia and pain caused by deposition of monosodium uric acid (MSU) in joints and other parts. The main reason is purine metabolism disorder and / or uric acid excretion disorder. It is estimated that there are more than 20 million gout patients worldwide. Currently, the drugs used to treat gout are very limited: 1) emergency medicine: colchicine tablets, non-steroidal anti-inflammatory drugs (NSAIDs) and glucocorticoids for pain relief; 2) inhibition of uric acid production: allopurinol, side effects febuxostat, ineffective in some patients; 3) Drugs that promote uric acid excretion: benzbromarone, etc., are prone to liver damage and are not suitable for patients with r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/58C07D277/82A61K31/428A61K31/423A61P19/06
CPCC07D263/58C07D277/82A61K31/423A61K31/428A61P9/00A61P9/12A61P13/04A61P13/12A61P19/06A61P43/00C07D277/68
Inventor 王亚平郑国君刘礼飞石磊周结波丁芳
Owner ZHEJIANG HISUN PHARMA CO LTD
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