Naproxen eugenol ester medicinal compound and preparation method of naproxen eugenol ester medicinal compound

A technology of naproxen eugenol ester and eugenol ester, which is applied in the field of naproxen eugenol ester medicinal compound and its preparation, can solve problems such as eugenol irritation, and achieve reduced irritation, excellent analgesic activity, and gastrointestinal The effect of low toxicity

Inactive Publication Date: 2012-09-12
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the irritation and volatility of eugenol, its application is limited to a certain extent.
At present, the preparation and preparation method of eugenol esters using aspirin and ibuprofen as raw materials have applied for patents, but the eugenol esters prepared from naproxen have not been reported yet.

Method used

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  • Naproxen eugenol ester medicinal compound and preparation method of naproxen eugenol ester medicinal compound
  • Naproxen eugenol ester medicinal compound and preparation method of naproxen eugenol ester medicinal compound
  • Naproxen eugenol ester medicinal compound and preparation method of naproxen eugenol ester medicinal compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] This example is the synthesis process of naproxen eugenol ester:

[0034] In a 250mL three-necked flask equipped with a stirrer and a thermometer, add 10g of naproxen and dissolve it in 80mL of dichloromethane, add 10mL of oxalyl chloride with an addition funnel, and react in an ice water bath at -5~0℃ for 3 hours. The excess oxalyl chloride is removed to obtain naproxenyl chloride.

[0035] Dissolve 5.5 g of eugenol in dichloromethane and 80 mL of the solution, add naproxen’s acid chloride with an addition funnel, react in an ice-water bath -5°C for 4 hours, filter, recover the dichloromethane, and dissolve the concentrated solution in dichloromethane. Wash once with saturated potassium carbonate solution and 3 times with distilled water. Dry the organic phase with anhydrous sodium sulfate overnight. Filter under reduced pressure and recover the solvent. Repeatedly recrystallize with ethyl acetate to obtain white solid crystals. The melting point is 120℃-121. ℃, that is, n...

Embodiment 2

[0037] This example is the synthesis process of naproxen eugenol ester:

[0038] In a 250mL three-necked flask equipped with a stirrer and a thermometer, add 12g of naproxen and dissolve it in 100mL of tetrahydrofuran, add 15mL of oxalyl chloride with an addition funnel, and react in an ice water bath at 0°C for 5 hours. The excess oxalyl chloride is evaporated under reduced pressure , Get naproxen acid chloride.

[0039] Dissolve 8.2 g of eugenol in 100 mL of tetrahydrofuran solution, add naproxen’s acid chloride with an addition funnel, react for 8 hours in an ice-water bath at 0°C, filter, and recover tetrahydrofuran. The concentrated solution is dissolved in dichloromethane and washed with saturated potassium carbonate solution. Once, washed with distilled water 3 times, the organic phase was dried overnight with anhydrous sodium sulfate, filtered under reduced pressure and the solvent was recovered, and recrystallized with ethyl acetate repeatedly to obtain white solid crystal...

Embodiment 3

[0041] This example is the synthesis process of naproxen eugenol ester:

[0042] In a 250mL three-necked flask equipped with a stirrer and a thermometer, add 11g of naproxen and dissolve it in 00mL of dichloromethane, add 12mL of oxalyl chloride with an addition funnel, and react in an ice water bath at -5℃ for 4 hours. Of oxalyl chloride to obtain naproxenyl chloride.

[0043] Dissolve 7 g of eugenol in 100 mL of dichloromethane solution, add naproxen’s acid chloride with an addition funnel, react for 6 hours in an ice-water bath at -5°C, filter, and recover dichloromethane. The concentrated solution is dissolved in dichloromethane and saturated Wash with potassium carbonate solution once, wash with distilled water 3 times, dry the organic phase with anhydrous sodium sulfate overnight, filter under reduced pressure and recover the solvent, recrystallize with ethyl acetate repeatedly to obtain white solid crystals, the melting point is 120℃-121℃, Namely naproxen eugenol ester....

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Abstract

The invention discloses a naproxen eugenol ester medicinal compound and belongs to propionic acid, 2-(6-methoxy group) naphthalin and 2-methoxyl group-4-(2- allyl) phenyl ester. According to the compound, naproxen is used as raw materials, the acylation is carried out, the naproxen with eugenol are subjected to esterification reaction in dissolvent, and the compound is prepared through recrystallization and purification. Through being used as efficient medicinal ingredients, the compound can be prepared into solid preparations, liquid preparations, injections, ophthalmic preparations, ointments, suppositories, film agents, aerosol or external preparations for clinical diseases of anti-inflammatory, antipyretic and analgesics and the like, particularly for diseases caused by infection.

Description

technical field [0001] The invention discloses a naproxen eugenol ester medicinal compound and a preparation method thereof, which is a non-steroidal anti-inflammatory drug naproxen and eugenol ester-forming compound with antipyretic, analgesic and antibacterial effects and a preparation method thereof , and pharmaceutical preparations in dosage forms such as solid preparations, liquid preparations, injections, ophthalmic preparations, ointments, suppositories, film preparations, aerosols or external preparations made of the compound as an effective pharmaceutical ingredient, which belong to the field of medical technology . Background technique [0002] Naproxen is a non-steroidal anti-inflammatory drug (nonsteroidal anti-inflammatory drugs, NSAIDs), by inhibiting prostaglandin cyclooxygenase (COX), preventing arachidonic acid from converting into prostaglandins (PGs) to exert anti-inflammatory and anti-inflammatory effects. Pain and antipyretic effect, widely used clinica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/734C07C67/14A61K31/216A61P29/00A61P31/04
Inventor 梁迪滕利荣杨晓虹王文娜谢冰雪田野孟庆繁逯家辉
Owner JILIN UNIV
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