Fenofibrate acid salt, preparation method, pharmaceutical composition and application

A technology for fenofibrate acid and medicine, applied in the field of medicine, can solve the problems of low absorption and utilization rate, complicated process, insoluble fenofibrate in water, etc., and achieve the effects of improved bioavailability and easy absorption

Inactive Publication Date: 2012-01-04
TETRANOV PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these technologies are not only complicated in process, but also unsatisfactory in effect, and cannot fundamentally solve the problem that fenofibrate is insoluble in water and has low absorption and utilization rate in the human body

Method used

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  • Fenofibrate acid salt, preparation method, pharmaceutical composition and application
  • Fenofibrate acid salt, preparation method, pharmaceutical composition and application
  • Fenofibrate acid salt, preparation method, pharmaceutical composition and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Fenofibric acid piperidine salt, its structural formula is:

[0032] .

[0033] The preparation method of fenofibric acid piperidine salt: dissolve 3.18g fenofibrate acid (10 mmol) in 20ml ethanol, add 0.8g piperidine (10mmol), heat and reflux for 0.5 hours, cool to room temperature, and gradually precipitate The white precipitate was filtered, collected, washed with ethanol, and dried in vacuo to obtain 3.18 g of fenofibric acid piperidine salt as a white solid, with a yield of 80%. Melting point 148-149°C, NMR analysis data 1 H NMR (400MHz, d 6 -DMSO): δ7.68-7.61 (m, 6H), 6.90 (bs, 2H), 2.89 (bs,4H ), 1.58-1.47 (m, 12H).

Embodiment 2

[0035] Fenofibric acid 2-methylpiperidinium salt, its structural formula is:

[0036] .

[0037] The preparation method of fenofibric acid 2-methylpiperidine salt: dissolve 3.18g fenofibric acid (10 mmol) in 20ml ethanol, add 0.94g 2-methylpiperidine (10mmol), heat and reflux for 0.5 Hours, cooled to room temperature, a white precipitate gradually precipitated, filtered, collected and washed with ethanol, dried in vacuo to obtain 3.05 g of fenofibric acid 2-methylpiperidine salt white solid, yield 74%. Melting point 135-136°C, nuclear magnetic analysis data 1 H NMR (400MHz, d 6 -DMSO): δ7.69-7.58 (m, 6H), 6.91 (d, J=8.8Hz, 2H), 3.10 (d, J=12.4Hz, 1H), 2.95-2.91 (m, 1H), 2.73- 2.66 (m, 1H), 1.68-1.64 (m, 3H), 1.59-1.51 (m, 7H), 1.41-1.27 (m, 2H), 1.13 (d, J=6.4Hz, 3H).

Embodiment 3

[0039] Fenofibric acid 3-methylpiperidinium salt, its structural formula is:

[0040] .

[0041] The preparation method of fenofibric acid 3-methylpiperidine salt: dissolve 3.18g fenofibric acid (10 mmol) in 20ml ethanol, add 0.94g 3-methylpiperidine (10mmol), heat and reflux for 0.5 Hours, cooled to room temperature, a white precipitate gradually precipitated, filtered, collected the precipitate and washed with ethanol, dried in vacuo to obtain 3.25 g of fenofibric acid 3-methylpiperidine salt as a white solid, with a yield of 79%. Melting point 131°C, nuclear magnetic analysis data1 H NMR (400MHz, d 6 -DMSO): δ 7.69-7.58 (m, 6H), 6.90 (d, J=8.8Hz, 2H), 3.08 (d, J=12Hz, 1H), 3.01 (d, J=10Hz, 1H), 2.63- 2.56 (m, 1H), 2.31 (t, J=12Hz, 1H), 1.69-1.63 (m, 4H), 1.48 (s, 6H), 0.81 (d, J=6.4Hz, 3H).

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Abstract

The invention discloses fenofibrate acid salt, a preparation method, a pharmaceutical composition and application. The structural general formula of the fenofibrate acid salt is shown as an equation or an equation in the specification, wherein X represents methylene, O, CH3-N or CH3-CH; R1 represents methyl; m represents 0, 1, 2, 3 or 4; R2 represents H or methyl; and R3 represents HOCH2CH2OCH2CH2-, HOCH2CH2CH2-, HOCH2CH(OH)CH2-, HOCH2CH2-, HOCH2C(CH3)2-, (HOCH2)2CCH3- or HOCH2CH(CH3CH2)-. Compared with the current fenofibrate, the solubility of the fenofibrate acid salt provided by the invention in water is obviously increased; the solubility in 1 ml of pure water is more than 1 mg; the highest solubility is above 100 mg, therefore, the fenofibrate acid salt is easily absorbed by human bodies; and the bioavailability is also relatively and obviously increased.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a salt of fenofibrate, a preparation method, a pharmaceutical composition and an application. Background technique [0002] Hyperlipidemia is a type of disease that seriously threatens human health, including high cholesterol, high triglycerides, high low-density lipoprotein, etc. These three diseases cause a series of common clinical diseases, such as coronary heart disease, angina pectoris, myocardial infarction Wait. Hyperlipidemia is a common and frequently-occurring disease. With the aging population in China, hyperlipidemia will increase year by year. [0003] Fenofibrate tablets have been recorded in the Chinese Pharmacopoeia and are currently the drug of choice for the treatment of hyperlipidemia. Fenofibrate drugs can effectively reduce low-density lipoprotein and ultra-low-density lipoprotein levels, increase high-density lipoprotein levels, and reduce triglyceride l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/037C07D295/023C07C59/90C07C51/41C07D211/12C07C215/40C07C213/08A61K31/205A61P3/06
Inventor 吴豫生邹大鹏李敬亚牛成山刘伦郭瑞云
Owner TETRANOV PHARMA CO LTD
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