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

A technology for compounds and compositions, applied in the directions of active ingredients of heterocyclic compounds, pharmaceutical combinations, medical preparations containing active ingredients, etc.

Inactive Publication Date: 2009-03-11
KOREA RES INST OF BIOSCI & BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, there are no reports or disclosures about novel oxopiperidine compounds showing possible inhibition of HDAC activity and anticancer activity in any of the above-cited documents, which publications are hereby incorporated by reference.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0228] Example 1. Preparation of 3-[1-(2,4-dimethoxybenzyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-N-hydroxyl propionamide ( 1e)

[0229]

[0230] Step 1. Preparation of Allyl-(2,4-Dimethoxybenzyl)amine (1b)

[0231] 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 neutralizing the reaction mixture 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 compound formed was purified by column chromatography on silica gel using a solvent mixture of methanol and chloroform (1:9) as eluent to give 276 mg of allyl-(2,4-dimethoxybenzyl)amine (1b) ( Yield: 40%).

[0232] 1 H-NMR (300MHz, CDCl 3 )δ 7.12(d, J=8.1Hz, 1H), 6.44-6.39(m, 2H), 5.99-5.86(m, 1H...

Embodiment 2

[0242] Example 2. Preparation of 3-(1-benzyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-N-hydroxyl-propionamide (2e)

[0243] 3-(1-Benzyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-N-hydroxy-propionamide (2e) was prepared analogously to that described in Example 1 above (See Table 1).

Embodiment 3

[0244] Example 3. Preparation of N-hydroxy-3-(2-oxo-1-phenethyl-2,5-dihydro-1H-pyrrol-3-yl)-propionamide (3e)

[0245] N-Hydroxy-3-(2-oxo-1-phenethyl-2,5-dihydro-1H-pyrrol-3-yl)-propionamide (3e ) (see Table 1).

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Abstract

The present invention is related to novel use of 2-oxo-heterocyclic compounds having anticancer activity and the process for preparing them and a pharmaceutical composition comprising the same. The present invention provides a pharmaceutical composition for preventing and treating the cancer disease comprising lung cancer, bone cancer, pancreatic cancer, skin cancer, cancer of the head and neck, cutaneous or intraocular melanoma, uterine cancer, ovarian cancer, rectal cancer or cancer of the anal region, stomach cancer, colon cancer, breast cancer, gynecologic tumors, Hodgkin's disease, cancer of the esophagus, cancer of the small intestine, cancer of the endocrine system, sarcomas of soft tissues, cancer of the urethra, cancer of the penis, prostate cancer, chronic or acute leukemia, solid tumors of childhood, lymphocytic lymphonas, cancer of the bladder, cancer of the kidney or ureter, or neoplasms of the central nervous system, therefore, it can be used as the therapeutics for treating and preventing cancer diseases.

Description

technical field [0001] The present invention relates to novel uses of 2-oxo-heterocyclic compounds having anticancer activity and pharmaceutical compositions comprising said compounds. Background technique [0002] Cancer is characterized by the formation of groups of cells called tumors caused by abnormal, uncontrolled cell growth, infiltration into adjacent tissues, and extensive metastasis to other organs, a process called neoplasia. Worldwide, more than 20 million people suffer from cancer each year, of whom 6 million die from the disease each year. The origin of cancer is divided into internal factors such as genetic factors, immune factors, etc., and external factors such as various chemical substances, radiation, viruses, and the like. Cancer may result when the balance between oncogenes and tumor suppressor genes is disrupted by the above factors. [0003] Histone is a nuclear protein that binds to nuclear DNA. Histone acetylation occurs at the ε-amino group of the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/4015A61P35/00A61K31/45A61K31/4402A61K31/4462
CPCA61K31/4015A61K31/454A61K31/4545C07D207/38C07D211/86C07D223/10C07D417/06
Inventor 金桓默韩均熙朴成圭李昌雨韩相配李奇勋高永熹梁镇赫朴范雨李香雨韩正焕柳东圭李真河千泰奎金容基李熙允李峰镛金点熔金知德刘景雅金宣怜
Owner KOREA RES INST OF BIOSCI & BIOTECH
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