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Compound with antiandrogen activity as well as preparation method and application of compound

An anti-androgen and compound technology, applied in the field of biomedicine, can solve problems such as limiting general application, and achieve the effect of good curative effect and good bioavailability

Inactive Publication Date: 2014-08-06
上海孚一生物科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in our research, we found that the solubility of structural formula II in ethanol is only 0.01%, which seriously limits its general application, so we have made further improvements to the structure

Method used

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  • Compound with antiandrogen activity as well as preparation method and application of compound
  • Compound with antiandrogen activity as well as preparation method and application of compound
  • Compound with antiandrogen activity as well as preparation method and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 10g of compound IV (33.6mmol) and 10g of compound V (51mmol) were added to 50ml of DMF under stirring between 20°C and 25°C, and stirred until dissolved, then 2.5g of sodium metal (0.1 mol). The reaction solution was stirred and reacted at room temperature for 24 hours, and then 2.5 ml of saturated ammonium chloride solution was added to the reaction solution to quench the sodium metal. The resulting reaction solution was poured into 250ml of ice water, stirred to precipitate precipitates, suction filtered, and the filter cake was vacuum-dried and then recrystallized in 200ml of ethanol to obtain 3.73g of product compound III with a yield of 27%.

Embodiment 2

[0023] Between 0°C and 5°C, 2.5g of sodium hydrogen (0.1mol) was added in batches to 20ml of DMF under stirring, and the solution formed by 10g of compound IV (33.6mmol) and 30ml of DMF was added dropwise to sodium hydrogen and In the suspension formed by DMF, 10 g of compound V (51 mmol) was added after the dropwise addition. The reaction solution was stirred at room temperature for 24 hours, and then 2.5 ml of saturated ammonium chloride solution was added to the reaction solution to quench the sodium hydrogen. The resulting reaction solution was poured into 250ml of ice water, stirred to precipitate the precipitate, filtered with suction, and the filter cake was vacuum-dried and then recrystallized in 200ml of ethanol to obtain 4.05g of compound III with a yield of 29.3%.

Embodiment 3

[0025] 10g of compound IV (33.6mmol) and 10g of compound V (51mmol) were added between 20°C and 25°C in 50ml of DMF under stirring, and after stirring until dissolved, 10g of potassium carbonate (72.4mmol) was added to the reaction solution ). The reaction solution was stirred at room temperature for 72 hours. The resulting reaction solution was poured into 250ml of ice water, stirred to precipitate precipitates, filtered with suction, and the filter cake was vacuum-dried and then recrystallized in 500ml of ethanol to obtain 11.29g of compound III with a yield of 81.6%. Melting point: 99℃~101℃. NMR confirmed the structure. H NMR (CDCl3, 400MHz) δ1.54(s, 6H, CH3), 1.77(m, 4H, CH2), 2.06(s, 3H, CH3), 3.39(m, 2H, CH2), 4.12(m, 4H , CH2), 7.91 (d, 1H, CH), 8.01 (dd, 1H, CH), 8.16 (d, 1H, CH). The solubility of compound III in ethanol reaches 2.5g / 100g.

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Abstract

The invention belongs to the technical field of biological medicines and particularly relates to a compound with antiandrogen activity as well as a preparation method and application of the compound. The compound provided by the invention has the chemical name as follows: 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5, 5-dimethyl-2, 4-dioxo-1-imidazolyl)butyl acetate. The preparation method comprises the step of enabling an intermediate compound IV and 4-bromobutyl acetate to react at the temperature of 10-60 DEG C under the catalysis of a catalyst to prepare the compound. The compound can be used for preparing antiandrogen drugs. The preparation method is simple; in addition, the obtained compound is high in bioavailability and antiandrogen activity.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to an anti-androgen active substance. Background technique [0002] Androgenetic alopecia (AGA) is a very common form of hair loss that can occur in both men and women. The reason why women also have AGA is that women also have androgens in their bodies. Not everyone will have AGA symptoms, suggesting that people without a family genetic background will be less likely to develop it. This is an androgen-dependent hereditary hair loss disorder that is progressive and, if left untreated, the symptoms of hair loss can become severe. AGA is one of the most common symptoms of hair loss. It can occur in all age groups, and both men and women can be affected. Although the patient has no obvious discomfort, he urgently requires treatment because it affects the appearance. [0003] Human cytoplasm contains 5α-reductase, which will react with testosterone to become dihydrote...

Claims

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Application Information

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IPC IPC(8): C07D233/78A61P5/28
CPCC07D233/72
Inventor 赵来春闵辉
Owner 上海孚一生物科技有限公司
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