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Novel 2-oxo-heterocyclic compounds and the pharmaceutical compositions comprising the same

A compound, oxo technology, applied in the direction of active ingredients of heterocyclic compounds, drug combinations, antipyretics, etc., can solve problems such as side effects, limit the use of conventional drugs, and cannot achieve satisfactory results, and achieve a strong inhibitory effect

Inactive Publication Date: 2009-09-02
KOREA RES INST OF BIOSCI & BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of conventional drugs for treatment can not achieve satisfactory results, and has various side effects, which limits the use of conventional drugs
[0011] For example, anti-inflammatory drugs such as aspirin or butazolin have been used to relieve the syndromes of OA and PA, however, it is difficult to keep these drugs administered because of their side effects, such as severe gastric Stimulation leading to gastritis, gastric ulcer, etc.

Method used

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  • Novel 2-oxo-heterocyclic compounds and the pharmaceutical compositions comprising the same
  • Novel 2-oxo-heterocyclic compounds and the pharmaceutical compositions comprising the same
  • Novel 2-oxo-heterocyclic compounds and the pharmaceutical compositions comprising the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0225] Example 1. Preparation of 3-[1-(2,4-dimethoxybenzyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-N-hydroxyl propionamide ( 1e)

[0226]

[0227] Step 1. Preparation of allyl-(2,4-dimethoxybenzyl)amine (1b )

[0228] Under stirring, 0.32 ml of allyl bromide (3.66 mM) and 0.7 ml of diisopropylethylamine (3.99 mM) were added to 500 mg of 2,4-dimethoxybenzyl dissolved in dichloromethane In the reaction solution of amine (3.33 mM), the solution was left alone at room temperature. After the reaction mixture was neutralized with 10% NaOH solution, the mixture was extracted with chloroform, washed with saturated NaCl solution, washed with MgSO 4 Dry, filter, and concentrate in vacuo. The formed compound was purified by silica gel column chromatography using a solvent mixture of methanol and chloroform (1:9) as eluent to obtain 276 mg of allyl-(2,4-dimethoxybenzyl)amine (1b) ( Yield: 40%).

[0229] 1 H-NMR (300MHz, CDCl 3 )δ7.12(d, J=8.1Hz, 1H), 6.44-6.39(m, 2H), 5.99-5.86(m, 1...

Embodiment 2

[0239] Example 2. Preparation of 3-(1-benzyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-N-hydroxyl-propionamide (2e)

[0240] 3-(1-Benzyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-N-hydroxy-propionamide (2e) was prepared in a similar manner to that described in Example 1 above 1 (see Table 1).

Embodiment 3

[0241] Example 3. Preparation of N-hydroxy-3-(2-oxo-1-phenethyl-2,5-dihydro-1H-pyrrol-3-yl)-propionamide (3e)

[0242] N-Hydroxy-3-(2-oxo-1-phenethyl-2,5-dihydro-1H-pyrrol-3-yl)-propionamide (3e) was prepared in a similar manner to that described in the above examples 1 (see Table 1).

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Abstract

PURPOSE: Provided are 2-oxo-piperidine derivatives having anti-inflammatory activity, a preparation method thereof and a composition for treating inflammatory disease containing the same compounds, which compounds have strong inhibiting activity on the formation of cytokine such as tumor necrosis factor-α(TNF-α) or nitrogen oxide(NO), so that the compound can be useful for treating inflammatory disease. CONSTITUTION: The 2-oxo-piperidine derivatives represented by formula (I) or pharmaceutically acceptable salts thereof are provided, wherein X is -OH, -NHOH or -NHOCH2Ph; n is an integer of 1 to 5; R is optional substituent, and hydrogen or R' substituted C1-C4 lower alkyl, alkenyl, alkynyl and aryl; and R' is a substituent selected from hydrogen, thiopenyl, naphthyl, pyrrole and furyl. The composition for treating inflammatory disease contains the 2-oxo-piperidine derivatives of formula (I) or pharmaceutically acceptable salts thereof as effective components.

Description

technical field [0001] The present invention relates to 2-oxo-heterocyclic compounds which are effective anti-inflammatory agents and pharmaceutical compositions comprising said compounds. Background technique [0002] Inflammation due to mechanical scars or various bacterial infections etc. is a normal reaction of the human body related to edema, pain etc. Usually, arthritic syndrome occurs only temporarily, but, when severe, it can cause long-term and eventual deformity. Joint disease can be divided into several groups of diseases, such as rheumatoid arthritis (RA), rheumatic inflammation associated with the disease, etc. Of these, specifically, arthritis is the most frequent and is a chronic disease characterized by inflammatory changes in the synovial lining of the joint capsule, which may progress to affect all joints of the body, at worst will cause disability. Progressive joint diseases such as rheumatoid arthritis cause joint disorders such as joint deformity and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/88A61K31/40A61P31/00A61P19/02A61P37/00A61P29/00A61P3/00
CPCA61H23/02A61H39/04A61H2201/1635A61H2201/1695
Inventor 高永熹韩均熙李昊宰朴范雨全孝坤金桓默朴成圭韩相配柳东圭千泰奎李真河李昌雨李奇勋李熙允
Owner KOREA RES INST OF BIOSCI & BIOTECH
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