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Anti-inflammatory COX/LOX inhibitor, and preparation method and application thereof

A technology of inhibitor and synthesis method, which is applied in the directions of anti-inflammatory agents, medical preparations containing active ingredients, pharmaceutical formulas, etc., can solve the problems of poor selectivity of NSAIDs, limited wide application, intestinal toxicity and side effects, etc., and achieves a simple preparation method. Easy to operate, reduce ear swelling, less gastrointestinal irritation

Active Publication Date: 2019-03-29
SECOND AFFILIATED HOSPITAL OF COLLEGE OF MEDICINEOF XIAN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional NSAIDs such as aspirin, ibuprofen and diclofenac are non-selective COX inhibitors; however, traditional NSAIDs have poor selectivity, and long-term use has some side effects such as intestinal toxicity and nephrotoxicity, which limits their wide application in clinical practice

Method used

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  • Anti-inflammatory COX/LOX inhibitor, and preparation method and application thereof
  • Anti-inflammatory COX/LOX inhibitor, and preparation method and application thereof
  • Anti-inflammatory COX/LOX inhibitor, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1 preparation

[0039] (1) The synthesis method is as follows:

[0040] Take pyrrole (10mmol), CH 2 CH 3 OCH 2Add Br (11mmol) and sodium hydride (12mmol) to 20mL dimethylformamide, stir at 40°C for 5 hours to obtain a reaction solution; add saturated aqueous sodium chloride solution and ethyl acetate to extract the reaction solution , the organic phase was concentrated and purified by column, and the purified solution was collected and distilled under reduced pressure to obtain 1.14 g (9.1 mmol) of 1-(ethoxymethyl)-1H-pyrrole, with a yield of 91%.

[0041] (2) The synthesis method is as follows:

[0042] Take 1-(ethoxymethyl)-1H-pyrrole (5mmol), (6mmol), zinc chloride (4mmol), join in 10mL dichloromethane, stir 6 hours at room temperature, obtain reaction liquid; Add saturated sodium chloride aqueous solution, ethyl acetate extraction in described reaction liquid, organic phase After concentration, the column was purified, and the purified soluti...

Embodiment 2

[0046] Embodiment 2 preparation

[0047] (1) The synthesis method is as follows:

[0048] Take pyrrole (10mmol), methyl iodide (11mmol), sodium hydroxide (11mmol), join in 20mL dimethyl sulfoxide, stir at room temperature for 5 hours, obtain reaction solution; Add saturated sodium chloride to the reaction solution The aqueous solution and ethyl acetate were extracted, the organic phase was concentrated and purified by column, and the purified solution was collected and distilled under reduced pressure to obtain 753 mg (9.3 mmol) of N-methylpyrrole, with a yield of 93%.

[0049] (2) The synthesis method is as follows:

[0050] Take N-methylpyrrole (5mmol), (6mmol), aluminum chloride (4mmol), join in 10mL methylene chloride, stir 4 hours at room temperature, obtain reaction solution; Add saturated sodium chloride aqueous solution, ethyl acetate extraction in described reaction solution, organic After the phase was concentrated, the column was purified, and the purified...

Embodiment 3

[0054] Example 3 Preparation

[0055] (1) The synthesis method is as follows:

[0056] Take pyrrole (10mmol), benzyl bromide (12mmol), and potassium carbonate (15mmol), add them to 25mL of tetrahydrofuran, and stir at room temperature for 6 hours to obtain a reaction solution; add saturated aqueous sodium chloride solution, acetic acid After extraction with ethyl ester, the organic phase was concentrated and then purified by column. The collected purified solution was distilled under reduced pressure to obtain 1.49 g (9.5 mmol) of N-benzylpyrrole with a yield of 95%.

[0057] (2) The synthesis method is as follows:

[0058] Take N-benzylpyrrole (5mmol), (6mmol), zinc chloride (4mmol), join in 10mL chloroform, stir 4 hours at room temperature, obtain reaction solution; Add saturated sodium chloride aqueous solution, ethyl acetate extraction in described reaction solution, after the organic phase concentrates After column purification, the purified liquid was collected...

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Abstract

The invention provides an anti-inflammatory COX / LOX inhibitor, and a preparation method and an application thereof. The inhibitor is a compound represented by formula I, or a pharmaceutically acceptable salt thereof. The novel anti-inflammatory COX / LOX inhibitor can significantly reduce the ear swelling degree of mice in an administrated group in xylene-induced ear swelling test, so the compound has an anti-inflammatory effect, and the anti-inflammatory effect of the compound is equivalent with that of aspirin; and additionally, pharmacological tests show that the compound has small irritationto the gastrointestinal tract. The preparation method of the novel anti-inflammatory COX / LOX inhibitor has the advantages of simplicity, easiness in operation, and effectiveness in the reduction of the production cost to realize industrial production.

Description

technical field [0001] The field of the invention belongs to the field of medicine, and in particular relates to a COX / LOX inhibitor for anti-inflammation and its preparation method and application. Background technique [0002] Non-steroidal anti-inflammatory drugs (NSAIDs) are a class of drugs widely used for anti-inflammatory, antipyretic and analgesic, and are often used clinically to treat inflammation of bone and joint (OA), muscle and soft tissue. Traditional NSAIDs such as aspirin, ibuprofen and diclofenac are non-selective COX inhibitors; however, traditional NSAIDs have poor selectivity, and long-term use has some side effects such as intestinal toxicity and nephrotoxicity, which limits their wide application in clinical practice . Therefore, the development of new NSAIDs that can reduce the side effects of traditional NSAIDs and have good activity has become the main direction of the development of these drugs. [0003] Dual inhibitors produce synergistic anti-i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14A61P29/00A61K31/4439
CPCA61P29/00C07D401/14
Inventor 王晓舟杨蓉王庆丰
Owner SECOND AFFILIATED HOSPITAL OF COLLEGE OF MEDICINEOF XIAN JIAOTONG UNIV
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