Composition for preventing or treating cancer containing novel trifluoromethylphenylpyrazole derivative as active ingredient

A trifluoromethyl, phenyl technology, applied in the field of compositions containing novel trifluoromethyl phenylpyrazole derivatives as active ingredients for preventing or treating cancer, can solve the problem of no therapeutic effect and reduce the efficiency of radiotherapy , serious side effects of normal cells, etc., to achieve the effect of reducing radioresistance and excellent apoptosis

Inactive Publication Date: 2022-07-08
KOREA INST OF RADIOLOGICAL & MEDICAL SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, many natural protein anticancer agents or peptide anticancer agents and chemically synthesized anticancer agents have been developed and used, but most of them not only exhibit severe side effects affecting normal cells in the body, but also depend on the type of cancer, or Even for the same type of cancer often does not have the same treatment effect depending on the patient
[0005] In particular, radiotherapy as a method of treating cancer is an essential treatment for various cancers, but the acquisition of radioresistance of cancer cells and damage to normal tissues during high-dose radiotherapy are continuously pointed out as reducing the efficacy of radiotherapy. efficiency problem

Method used

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  • Composition for preventing or treating cancer containing novel trifluoromethylphenylpyrazole derivative as active ingredient
  • Composition for preventing or treating cancer containing novel trifluoromethylphenylpyrazole derivative as active ingredient
  • Composition for preventing or treating cancer containing novel trifluoromethylphenylpyrazole derivative as active ingredient

Examples

Experimental program
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Effect test

Embodiment

[0110] Hereinafter, the present invention will be described in detail by way of examples. These embodiments are only for illustrating the present invention in more detail, and it will be apparent to those skilled in the art that the scope of the present invention is not limited by these embodiments according to the gist of the present invention.

preparation example

[0111] 3-(1-(4-(trifluoromethyl)phenyl)-1H-pyrazol-4-yl)aniline

[0112]

[0113] Step 1: Combine 4-iodotrifluorotoluene (1.00 g, 3.68 mmol), 4-chloro-1H-pyrazole (415 mg, 4.05 mmol), cesium carbonate (2.40 g, 7.36 mmol), CuI (105 mg, 0.55 mmol) ) was added to anhydrous toluene (35 mL) as a reaction solvent, followed by stirring at 110° C. for 24 hours. After the reaction product was confirmed by TLC, the reaction solution was diluted with EtOAc and washed with purified water. Anhydrous Na for organic layer 2 SO 4 It was dehydrated, concentrated under reduced pressure, and separated by silica gel column chromatography to obtain 1.12 g of the title compound (Compound 1). 1 H-NMR (300MHz, CDCl 3 ): δ8.23(s, 1H), 8.02(s, 1H), 7.89(2H, d, J=8.77Hz), 7.76(2H, d, J=8.77Hz); LC-MS (ESI, m / z)=247.0(M+H + ).

[0114] Step 2: The compound 1 obtained in step 1 (800 mg, 3.25 mmol) was put into a reaction vessel, and 3-aminophenylboronic acid (534 mg, 3.90 mmol), Pd(OAc) 2 (73...

preparation example 2

[0115] 2-(1-(4-(trifluoromethyl)phenyl)-1H-pyrazol-4-yl)benzaldehyde

[0116]

[0117] Compound 1 (800 mg, 3.25 mmol) obtained in Step 1 of Preparation Example 1 was placed in a reaction vessel, and (3-formylphenyl)boronic acid (585 mg, 3.90 mmol), Pd (PPh 3 ) 4 (375mg, 0.33mmol), Na 2 CO 3 (689 mg, 6.54 mmol) was added to dioxane (32 mL) followed by N 2(g) Treatment for 5 minutes. After stirring the reaction at 90°C for 8 hours, the product was confirmed by TLC and the solvent dioxane was removed by concentration under reduced pressure. The reaction concentrate was diluted with EtOAc and washed with purified water. Put the organic layer in anhydrous Na 2 SO 4 It was dehydrated, concentrated under reduced pressure, and separated by silica gel column chromatography to obtain 870 mg of the title compound (Compound 3). 1 H-NMR (300MHz, CDCl 3 ): δ9.85(s, 1H), 8.61(s, 1H), 8.21(s, 1H), 8.08(s, 1H), 7.95(1H, d, J=7.86Hz), 7.81(2H, d, J=8.74Hz), 7.67(2H,d,J=8.77Hz), 7....

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Abstract

The present invention relates to a composition for preventing or treating cancer containing a novel trifluoromethylphenylpyrazole derivative as an active ingredient, and more particularly, to a composition for preventing, alleviating or treating cancer and a radiosensitizer composition for treating cancer together with radiation therapy, the composition contains a novel sulfonamide derivative as an active ingredient, and the sulfonamide derivative comprises N, N-dimethyl-N '-(3-(1-(4-(trifluoromethyl) phenyl)-1H-pyrazol-4-yl) phenyl) azane sulfonamide. The novel sulfonamide derivative according to the present invention has an excellent apoptotic effect on cancer cells, and thus can be used as an effective anti-cancer agent, and can reduce radiation resistance of cancer cells, and thus can be used as a radiosensitizer composition during cancer treatment.

Description

technical field [0001] The present invention relates to a composition for preventing or treating cancer containing a novel trifluoromethylphenylpyrazole derivative as an active ingredient, and more particularly, to a composition for preventing, alleviating or treating cancer, and a composition for preventing, relieving or treating cancer. A radiosensitizer composition for the treatment of cancer, the composition containing a novel trifluoromethylphenylpyrazole derivative as an active ingredient, the trifluoromethylphenylpyrazole derivative including N,N-dimethyl -N'-(3-(1-(4-(trifluoromethyl)phenyl)-1H-pyrazol-4-yl)phenyl)azanesulfonamide. Background technique [0002] An effective and traditional treatment for diseases caused by the failure of normal genetic control, often referred to as cancer, is the removal and surgical excision of the tumor. However, in cases where the primary cancer has metastasized to other organs, surgery is not possible, so anticancer drug therapy ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12
CPCC07D231/12A61P35/00A61K31/415A61K31/4155A61K31/4439A61K31/454A61K41/0038A61N5/10A61N2005/1098C07D401/04C07D409/04
Inventor 金宰圣金阿英姜旻成郑官铃赵锡俊
Owner KOREA INST OF RADIOLOGICAL & MEDICAL SCI
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