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Application of O-(piperidinyl) ethyl derivative of Cleistanone in preparing drugs for resisting chronic obstructive pulmonary diseases

An ethyl derivative and a chronic obstructive technology, which is applied in the field of preparation of O-ethyl derivatives of Cleistanone, can solve the problems of difficulty in obtaining satisfactory curative effects, slow progress in drug treatment research, and different pathogenic mechanisms.

Inactive Publication Date: 2014-10-15
由日升
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no drug that can curb the progressive development of COPD, and the research progress of its drug treatment is quite slow. At present, the drug for treating asthma is often used in clinical practice to treat COPD. Because the pathogenesis of COPD is different from that of asthma, it is difficult to obtain satisfactory curative effect.

Method used

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  • Application of O-(piperidinyl) ethyl derivative of Cleistanone in preparing drugs for resisting chronic obstructive pulmonary diseases
  • Application of O-(piperidinyl) ethyl derivative of Cleistanone in preparing drugs for resisting chronic obstructive pulmonary diseases
  • Application of O-(piperidinyl) ethyl derivative of Cleistanone in preparing drugs for resisting chronic obstructive pulmonary diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 Preparation of Compound Cleistanone

[0021] The preparation method of the compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. , pages 4108–4111, August 2011).

[0022]

Embodiment 2

[0023] Example 2 Synthesis of O-Bromoethyl Derivatives (II) of Cleistanone

[0024] Compound I (440 mg, 1.00 mmol) was dissolved in 10 mL of benzene, and tetrabutylammonium bromide (TBAB) (0.04 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 6 mL of 50% sodium hydroxide solution. The mixture was stirred at 25 °C for 24 h. After 24 hours, the reaction solution was poured into ice water, extracted twice with dichloromethane immediately, and the organic phase solutions were combined. Then the organic phase solution was washed with water and saturated brine three times successively, then dried with anhydrous sodium sulfate, and finally concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1, v / v), and the yellow concentrated elution band was collected to obtain compound II as a yellow solid (344 mg, 63%).

[0025] 1H NMR (500MHz, DMSO-d 6...

Embodiment 3

[0029] Example 3 Synthesis of O-(piperidinyl)ethyl derivative (III) of cleistanone Cleistanone

[0030]Compound II (273 mg, 0.5 mmol) was dissolved in 20 mL of acetonitrile, anhydrous potassium carbonate (345 mg, 2.5 mmol), potassium iodide (84 mg, 0.5 mmol) and piperidine (852 mg, 10 mmol) were added thereto, and the mixture was heated to reflux for 16 h. After the reaction, the reaction solution was poured into 20 mL of ice water, extracted three times with an equal amount of dichloromethane, and the organic phases were combined. The combined organic phases were successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:0.5, v / v), and the yellow concentrated elution band was collected to obtain the yellow color of the O-(piperidinyl)ethyl derivative ...

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry and particularly to an O-(piperidinyl) ethyl derivative of Cleistanone, a preparation method for the O-(piperidinyl) ethyl derivative of the Cleistanone and the application of the O-(piperidinyl) ethyl derivative of the Cleistanone in preparing drugs for resisting chronic obstructive pulmonary diseases. The invention synthesizes a novel O-(piperidinyl) ethyl derivative of the Cleistanone and discloses the preparation method thereof. Pharmacological experiment results show that the O-(piperidinyl) ethyl derivative of the Cleistanone has the function of resisting chronic obstructive pulmonary diseases and has the value of developing drugs for resisting chronic obstructive pulmonary diseases.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to O-(piperidinyl)ethyl derivatives of cleistanone, a preparation method and uses thereof. Background technique [0002] Chronic obstructive pulmonary disease (chronic obstructive pulmonary disease, COPD) is a common chronic disease worldwide, currently ranking fourth in the global cause of death, according to the World Health Organization forecast, by 2020, COPD will be in the global disease Ranked fifth and third among causes of death. [0003] COPD is a disease characterized by not fully reversible airflow limitation associated with an abnormal inflammatory response of the lungs to noxious gases or noxious particles, with chronic inflammation throughout the airways, lung parenchyma, and pulmonary vessels. The cells involved in COPD include inflammatory cells such as neutrophils, T lymphocytes, and macrophages. When the cells are activated, they release v...

Claims

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Application Information

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IPC IPC(8): A61K31/58A61P11/00A61P29/00
Inventor 黄蓉吴俊艺吴俊华
Owner 由日升
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