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2-nitrophenylsulfonamide derivatives, and preparation method and medical application thereof

A nitro, pharmaceutical technology, applied in the field of 2-nitrophenylsulfonamide derivatives, can solve many problems such as

Inactive 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

Currently published patents on URAT1 inhibitors include WO2011046800, WO2011159839, WO2014183555A1, etc., but not many actually enter the clinic

Method used

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  • 2-nitrophenylsulfonamide derivatives, and preparation method and medical application thereof
  • 2-nitrophenylsulfonamide derivatives, and preparation method and medical application thereof
  • 2-nitrophenylsulfonamide derivatives, and preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-A

[0048] Synthesis of Example 1-A Compound 1 (Synthetic Method 1)

[0049]

[0050] Synthesis of Intermediate A

[0051] Dissolve 4-aminobenzonitrile (11.8g, 100mmol) in 100ml of acetic acid, add potassium thiocyanate (29.1g, 300mmol) and cool to about 10°C, slowly add liquid bromine (16g, 100mmol) dropwise, after the addition is complete Warm to room temperature and stir for 1 hour. The temperature was raised to 60° C., and the reaction was continued for 6 hours. Concentrate under reduced pressure, evaporate most of the acetic acid, add 100mL water, 200ml ethyl acetate, stir for 0.5 hours, filter with suction, wash with water, dry to obtain intermediate A 2-amino-6-cyanobenzothiazole (12.4g, yield 71%).

[0052] Synthesis of Compound 1 (Synthetic Method 1)

[0053] Dissolve compound A 2-amino-6-cyanobenzothiazole (700mg, 4mmol) in 10ml of pyridine, add 70mg of DMAP, cool to about 0°C with ice water, slowly add 2-nitrobenzene-1-sulfonyl chloride (1.06 g, 4.8mmol, 1.2eq),...

Embodiment 1-B

[0056] Synthesis of Example 1-B Compound 1 (Synthesis Method 2)

[0057]

[0058] Dissolve compound A 2-amino-6-cyanobenzothiazole (700mg, 4mmol) in 7ml toluene, add K 2 CO 3 (1.1g, 8mmol), 2-nitrobenzene-1-sulfonyl chloride (1.06g, 4.8mmol, 1.2eq), heated to reflux for about 10 hours after addition, to compound A 2-amino-6-cyanobenzo Thiazole disappears. 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 1 N-(6-cyanobenzothiazole)-2 -yl-(2-nitrophenyl)sulfonamide (1.12 g, yield 78%).

Embodiment 1-C

[0059] Synthesis of Example 1-C Compound 1 (Synthetic Method 3)

[0060]

[0061] Compound A 2-amino-6-cyanobenzothiazole (700mg, 4mmol) was dissolved in 7ml of anhydrous THF, cooled to about -20°C, and LDA / THF solution (4.8mL, 1mol / L, 1.2eq ), continue stirring at this temperature for 0.5 h after the addition, add 2-nitrobenzene-1-sulfonyl chloride (1.06 g, 4.8 mmol, 1.2 eq), and continue stirring at 0 ° C for 2 hours after the addition. 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 1N-(6-cyanobenzothiazole)-2- Amyl-(2-nitrophenyl)sulfonamide (1.22 g, yield 85%).

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Abstract

The invention relates to the field of medicines related to hyperuricemia and gout and specifically to 2-nitrophenylsulfonamide derivatives as shown in a general formula (I) which is described in the specification, application of the derivatives as URAT1 inhibitors, particularly as therapeutic agents for diseases associated with abnormal uric acid levels, and a preparation method for the derivatives. Each substituent in the general formula (I) is as defined in 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 2-nitrophenylsulfonamide derivative, its preparation method and medical application. 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 pa...

Claims

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Application Information

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IPC IPC(8): C07D277/82C07D263/58A61K31/423A61K31/428A61K45/06A61P9/12A61P19/06A61P19/02A61P29/00A61P9/00A61P9/10A61P13/12A61P17/06A61P39/02A61P13/04A61P5/20
CPCC07D277/82A61K31/423A61K31/428A61K45/06C07D263/58
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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