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Synthesis method of crisaborole

A synthetic method and compound technology, applied in the field of drug synthesis, can solve the problems of lack of therapeutic drugs for allergic dermatitis, etc., and achieve the effects of high yield, simple operation and high purity

Inactive Publication Date: 2017-07-07
湖南中智优库科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, there is no effective treatment for atopic dermatitis

Method used

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  • Synthesis method of crisaborole
  • Synthesis method of crisaborole
  • Synthesis method of crisaborole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] To benzo[c][1,2]oxaborolane-1,5(3H)-diol (0.51g, 3.42mmol) and 4-chlorobenzonitrile (0.44g, 3.21mmol) in DMF (10mL ) solution, cesium carbonate (2.45g, 7.52mmol) was added, and the mixture was heated to 80°C to react overnight. DMF was removed under reduced pressure, the residue was diluted with EtOAc (50 mL), then washed with water (10 mL) and saturated brine (10 mL), dried over sodium sulfate, filtered, concentrated, and purified to obtain 0.45 g of product with a yield of 87.7% , with a purity of 99.6%.

Embodiment 2

[0060] To benzo[c][1,2]oxaborolane-1,5(3H)-diol (0.46g, 3.05mmol) and 4-chlorobenzonitrile (0.47g, 3.40mmol) in DMF (10mL ) solution, cesium carbonate (2.29g, 7.03mmol) was added, and the mixture was heated to 90°C to react overnight. DMF was removed under reduced pressure, the residue was diluted with EtOAc (50 mL), then washed with water (10 mL) and saturated brine (10 mL), dried over sodium sulfate, filtered, concentrated, and purified to obtain 0.46 g of product with a yield of 92% , with a purity of 99.2%.

Embodiment 3

[0062] To benzo[c][1,2]oxaborolane-1,5(3H)-diol (0.3g, 2.0mmol) and 4-chlorobenzonitrile (0.41g, 3.0mmol) in DMF (10mL ) solution, potassium carbonate (1.95g, 6.0mmol) was added, and the mixture was heated to 95°C for 48h. DMF was removed under reduced pressure, the residue was diluted with EtOAc (50 mL), then washed with water (10 mL) and saturated brine (2×10 mL), dried over sodium sulfate, filtered, concentrated, and purified to give the product 0.26 g with a yield of 85 %, the purity is 98%.

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Abstract

The invention provides a synthesis method of crisaborole, belongs to the technical field of drug synthesis, and relates to a synthesis method of a novel boron-containing anti-inflammatory preparation, namely crisaborole. 4-halobenzonitrile and benzo[c][1,2] oxaborolane-1,5(3H)-diol are reacted in an organic solvent in the presence of alkali, and the crisaborole is obtained. The synthesis methoid is simple, and the crisaborole is high in yield and high in purity. (The reaction formula is shown in the description).

Description

technical field [0001] The invention belongs to the technical field of drug synthesis and relates to a synthesis method of a novel boron-containing anti-inflammatory preparation crisaborole. The synthesis method of the invention is simple, and the obtained crisaborole has high yield and high purity. Background technique [0002] Atopic dermatitis is a common relapsing chronic inflammatory skin disease. Patients usually present with chronic rashes characterized by inflammation and itching, usually in skin folds, and symptoms usually last for more than 14 days. It is estimated that about 25 million people in the United States suffer from atopic dermatitis (eczema), of which 8% to 18% are infants and children. Currently, there is no effective treatment for atopic dermatitis. The crisaborole drug is mainly used to treat children and adults with mild to moderate allergic dermatitis (eczema, eczema). The long-term safety study of crisaborole shows that the intermittent use of cr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04
CPCC07F5/04
Inventor 赵新华
Owner 湖南中智优库科技有限公司
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