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2-pyridyl thiazole derivative and application thereof

An alkyl and compound technology, applied in the field of 2-pyridyl thiazole derivatives, can solve problems such as lethal exfoliative dermatitis, injury, skin allergic reaction, liver and kidney function, etc., achieve prevention of hyperuricemia, excellent treatment and/or Effect

Active Publication Date: 2021-06-25
WUHAN OPTICS VALLEY YATAI PHARM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]Clinical uric acid-lowering drugs, namely: xanthine oxidase inhibitors are represented by allopurinol and febuxostat. Studies have shown that although allopurinol is First-line drug for hyperuricemia and gout, but it can cause skin allergic reaction and liver and kidney function damage, severe cases may cause fatal exfoliative dermatitis and other hypersensitivity syndrome, febuxostat has a significant effect, but still shows some Obvious adverse reactions, such as abnormal liver function, diarrhea, headache, rash, cardiotoxicity, etc.

Method used

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  • 2-pyridyl thiazole derivative and application thereof
  • 2-pyridyl thiazole derivative and application thereof
  • 2-pyridyl thiazole derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Compound 1: Synthesis of 2-(2-cyanopyridin-4-yl)-4-methylthiazole-5-carboxylic acid

[0070]

[0071] Step 1: Add ethyl 4-methylthiazole-5-carboxylate (3.2g, 21.1mmol), 4-bromopyridine-2-carbonitrile (3.0g, 16.3mmol), [1,1' - bis(diphenylphosphino)ferrocene]palladium dichloride (0.27g, 0.33mmol), sodium bicarbonate (3.4g, 34mmol), cuprous bromide (0.23g, 1.6mmol) and isobutyric acid Solution (0.04g), then add toluene (100ml), under nitrogen protection, heated to 110°C under stirring for 6 hours, cooled to room temperature, filtered the reaction solution, spin-dried, crude product with petroleum ether: ethyl acetate (10:1) Purified by column to obtain ethyl 2-(2-cyanopyridin-4-yl)-4-methylthiazole-5-carboxylate (A1-3) (3 g, 67.1%) as a white solid.

[0072] Step 2: Add ethyl 2-(2-cyanopyridin-4-yl)-4-methylthiazole-5-carboxylate (A1-3) (0.20g, 0.73mmol) to the reaction flask, then add cesium carbonate (0.24g, 0.73mmol) and dimethyl sulfoxide (5.0ml), heated to 90°C ...

Embodiment 2

[0077] Compound 2: Synthesis of 2-(2-cyanopyridin-4-yl)thiazole-5-carboxylic acid

[0078]

[0079] (compound 2)

[0080] In addition to the A1-1 (4-methylthiazole-5-ethyl carboxylate) in step 1

[0081] Replaced with ethyl thiazole-5-carboxylate Except that, according to the same steps and methods as in Example 1, compound 2 was synthesized.

[0082] LCMS (MS-ESI, m / z): (M+1) = 232.0

[0083] 1 H NMR (400MHz, DMSO-d 6,ppm): δ8.36(d,J=5.7Hz,1H),7.95(d,J=2.3Hz,1H),7.81(dd,J=5.7,2.2Hz,1H),7.46(s,1H) ,2.59(s,3H)

Embodiment 3

[0085] Compound 3: Synthesis of 2-(2-cyanopyridin-4-yl)-4-ethylthiazole-5-carboxylic acid

[0086]

[0087] Except for replacing A1-1 in step 1: ethyl 4-methylthiazole-5-carboxylate with ethyl 4-ethylthiazole-5-carboxylate, the compound was synthesized according to the same steps and methods as in Example 1 3.

[0088] LCMS (MS-ESI, m / z): (M+1) = 260.0

[0089] 1 H NMR (400MHz, DMSO-d 6 ,ppm): δ8.41(d,J=5.7Hz,1H),7.99(d,J=2.3Hz,1H),7.83(dd,J=5.7,2.2Hz,1H),7.46(s,1H) ,3.01(q,J=7.2Hz,2H),1.29(t,J=7.2Hz,3H).

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PUM

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Abstract

The invention develops a pyridine derivative shown as a general formula (I), a pharmaceutically acceptable salt of the pyridine derivative, and application of the pyridine derivative as a xanthine oxidase (XO) inhibitor. The derivative can be applied to drugs for preventing and / or treating hyperuricemia and gout.

Description

technical field [0001] The present invention relates to a novel compound having xanthine oxidase inhibitory activity and a preparation method thereof. In particular, the present invention relates to a compound effective as a therapeutic drug and / or preventive drug for diseases involving hyperuricemia and gout xanthine oxidase. - pyridylthiazole derivatives. Background technique [0002] Xanthine oxidase (Xanthine Oxidase, XO) is an enzyme with low specificity, which can not only catalyze hypoxanthine to xanthine, and then generate uric acid, but also directly catalyze xanthine to generate uric acid. [0003] Xanthine oxidase inhibitors (Xanthine oxidase inhibitors, XOI) reduce blood uric acid levels by inhibiting uric acid synthesis. Therefore, xanthine oxidase inhibitors are effective for the treatment of hyperuricemia and various diseases caused by it. For example, urate crystals precipitate in tissues, organs and joints caused by persistent hyperuricemia, causing gouty ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04C07D417/14A61P19/06A61K31/4439A61K31/501
CPCC07D417/04C07D417/14A61P19/06
Inventor 黄阳滨伍世平王火箭刘礼飞周远亮李平岑玉杰张春丽
Owner WUHAN OPTICS VALLEY YATAI PHARM RES INST CO LTD
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