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Ibuprofen derivative as well as preparation method and application thereof

A technology of derivatives and medicines, applied in the field of pharmaceutical compositions containing the ibuprofen derivatives, ibuprofen derivatives and their preparation, can solve the problems of short half-life and poor stability of ibuprofen, and achieve anti-inflammatory Antipyretic and analgesic weak, weak effect, good pharmacokinetic properties

Pending Publication Date: 2022-04-22
NANJING HERON PHARMA SCI & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The present invention obtains a kind of ibuprofen derivative N20 and its right-handed enantiomer N20 (S) by derivatizing the carboxyl group of racemic ibuprofen or S-ibuprofen, which overcomes the problem of ibuprofen Problems with short half-life, poor stability, irritation and compatibility

Method used

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  • Ibuprofen derivative as well as preparation method and application thereof
  • Ibuprofen derivative as well as preparation method and application thereof
  • Ibuprofen derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The synthesis of embodiment 1 compound N20

[0040]

[0041]At room temperature, weigh ibuprofen (2.1g, 10mmol), add DMF (10mL) and stir to dissolve, then add 4-chloromethyl-5-methyl-1,3-dioxol-2-one (1.5g, 10mmol), then the reaction flask was moved to an ice bath for stirring, and sodium carbonate (0.57g, 5mmol) was added to the reaction flask in 5 batches, and the addition was completed. The reaction was moved to room temperature and the reaction was stirred overnight. After the reaction was detected by TLC, 100ml of water, 50mL of ethyl acetate, and 0.5g of sodium thiosulfate were added to the reaction bottle, and the liquid was separated by shaking. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, suction filtered, and concentrated. Sand making, 2.0 g of light yellow oil was obtained by flash column chromatography, the yield was 64%.

[0042] 1 H NMR (400MHz, CDCl 3 )δ7.181-7.087(m,4H),4.810(m,2H),3.724(q,J=7,.2Hz),2.447...

Embodiment 2

[0044] Embodiment 2: the synthesis of compound N20 (S)

[0045]

[0046] The experimental method is the same as in Example 1, except that ibuprofen is replaced by S-ibuprofen.

[0047] 1 H NMR (400MHz, CDCl 3 )δ7.181-7.087(m,4H),4.810(m,2H),3.724(q,J=7,.2Hz),2.447(d,J=7.2Hz),2.107(s,3H),1.911- 1.776(m,1H),1.498(d,J=7.2Hz),0.894(d,J=6.6Hz).

[0048] ESI-MS m / z=341.1,[M+Na] + .

Embodiment 3

[0049] The synthesis of embodiment 3 compound N20 (S)

[0050] At room temperature, weigh S-ibuprofen (2.1g, 10mmol), add ethyl acetate (10mL) and stir to dissolve, then add 4-chloromethyl-5-methyl-1,3-dioxole -2-ketone (1.5g, 10mmol), then move the reaction flask to ice bath and stir, add sodium bicarbonate (0.57g, 5mmol) to the reaction flask in 5 batches, and the addition is complete. The reaction was moved to room temperature and the reaction was stirred overnight. After the reaction was detected by TLC, 100ml of water, 50mL of ethyl acetate, and 0.5g of sodium thiosulfate were added to the reaction bottle, and the liquid was separated by shaking. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, suction filtered, and concentrated. Sand making, 2.0 g of light yellow oil was obtained by flash column chromatography, the yield was 64%.

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Abstract

The invention relates to an ibuprofen derivative as well as a preparation method and application thereof. The ibuprofen derivative N20 and the dextrorotatory enantiomer N20 (S) thereof are obtained by derivatizing carboxyl of racemic ibuprofen or S-ibuprofen, and the problems of short half-life period, poor stability, irritation, compatibility and the like of ibuprofen are solved. In-vitro plasma and in-vivo rat tests show that the compound has good pharmacokinetic properties.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to an ibuprofen derivative, a preparation method and application thereof, and a pharmaceutical composition containing the ibuprofen derivative. Background technique [0002] Ibuprofen (Ibuprofen), chemically named 2-(4-isobutylphenyl) propionic acid, is a kind of aryl propionic acid non-steroidal anti-inflammatory drug, which was first listed in the UK in 1968. It is a kind of Non-selective cyclooxygenase inhibitor, it inhibits cyclooxygenase and reduces the synthesis of prostaglandins to produce analgesic and anti-inflammatory effects; it exerts antipyretic effect through the hypothalamic thermoregulation center. Because of its good anti-inflammatory, analgesic and antipyretic effects, and less adverse reactions, it is considered to be one of the safest non-steroidal anti-inflammatory drugs (NSAIDs), and has been widely used clinically. [0003] Contain a chiral carbon in the i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/40A61K31/365A61P29/00A61P19/02A61P25/06A61P25/04A61P25/02
CPCC07D317/40A61P29/00A61P19/02A61P25/06A61P25/04A61P25/02C07B2200/07
Inventor 吕田陈星燃闵涛王佳琳
Owner NANJING HERON PHARMA SCI & TECH CO LTD
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