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Amide compound and application thereof in treating cancer

A compound and solvate technology, applied in the field of medicine, can solve problems such as obvious side effects and no optimal treatment plan

Pending Publication Date: 2019-10-08
HINOVA PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the treatment of castration-resistant prostate cancer is mainly based on docetaxel, mitoxantrone, prednisone and other drugs combined with chemotherapy, the side effects are obvious, and there is no optimal treatment plan

Method used

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  • Amide compound and application thereof in treating cancer
  • Amide compound and application thereof in treating cancer
  • Amide compound and application thereof in treating cancer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0144] Example 1: 5-chloro-N-(2-chloro-4-trifluoromethylphenyl)-2-aminobenzamide (1)

[0145]

[0146] The first step: 5-chloro-N-(2-chloro-4-trifluoromethylphenyl)-2-nitrobenzamide (1-1)

[0147] Under nitrogen protection, 5-chloro-2-nitrobenzoic acid (5.0g, 24.8mmol), triethylamine (5.0g, 24.8mmol) and 3-chloro-4-aminotrifluorotoluene (4.6g, 23.6mmol ) was added to 50mL xylene, heated to 110°C, and phosphorus trichloride (3.4g, 24.8mmol) was slowly added dropwise. At 110°C, stir for 2h. Cool to room temperature and spin dry under vacuum. Add 100mL of water, filter the solid with suction, wash the filter cake with water, beat with a small amount of ethyl acetate, filter the solid with suction, and dry to obtain a white solid 5-chloro-N-(2-chloro-4-(trifluoromethyl) Phenyl)-2-nitrobenzamide (8.2 g, 21.6 mmol). Yield: 87.2%. MS(ESI)m / e396.0(M+18) + . 1 H NMR (400MHz, CDCl 3 )δ8.63 (d, J=8.5Hz, 1H), 8.16 (d, J=8.4Hz, 1H), 7.99 (s, 1H), 7.71 (s, 1H), 7.69-7.57 (m, 3H)....

Embodiment 2

[0150] Example 2: 5-Chloro-N-(2-chloro-4-(trifluoromethyl)phenyl)-2-(methylsulfonamido)benzamide (2)

[0151] 2-Amino-5-chloro-N-(2-chloro-4-(trifluoromethyl)phenyl)benzamide (100.0mg, 0.28mmol) and 3mL pyridine were slowly added dropwise with methanesulfonyl chloride (65.6 mg, 0.57mmol). Heat to 40°C and stir overnight. Dichloromethane and water were added for extraction, and the organic layer was washed with 1N dilute hydrochloric acid, then with saturated brine, dried, spin-dried, and purified by silica gel column chromatography. 5-Chloro-N-(2-chloro-4-(trifluoromethyl)phenyl)-2-(methylsulfonamido)benzamide (60.0 mg, 0.14 mmol) was obtained as a white solid. Yield: 49.0%. MS(ESI)m / e427.0(M+H) + .

Embodiment 3

[0152] Example 3: 5-chloro-N-(2-chloro-4-trifluoromethylphenyl)-2-propionamidobenzamide (3)

[0153] In a 25ml round bottom flask, put 5-chloro-N-(2-chloro-4-trifluoromethylphenyl)-2-aminobenzamide (0.2mmol, 70mg), propionyl chloride (1.2eq, 23mg) , dichloromethane 1ml and TEA (2eq, 40mg), stirred at room temperature overnight, the reaction solution was washed with dilute hydrochloric acid, washed with saturated brine, dried, spin-dried, slurried with ice dichloromethane, filtered to obtain 10mg of white solid, yield 13%

[0154] MS m / z (ESI): 210.2.

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PUM

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Abstract

The invention discloses an amide compound and an application thereof in treating cancer, and belongs to the field of pharmaceutical chemistry. The invention discloses the application of amide compoundshown in formula I, or crystal form, or stereoisomer, or isotope body, or tautomer, or pharmaceutically-acceptable salt, or solvate, or pro-drug, or metabolite thereof in treating cancer. Experimental results show that the compound can inhibit the proliferation of prostate cancer cells, especially has an obvious inhibition effect on drug-resistant prostate cancer cell line (22RV1). At the same time, the compound can obviously inhibit the proliferation of multiple cancer cells. In addition, the compound has good pharmacokinetics, which has a potential therapeutic effect on cancer, especially prostate cancer, and provides a new choice for clinical screening and / or preparation of cancer drugs.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to an amide compound and its application in treating cancer, especially the application in treating prostate cancer. Background technique [0002] Cancer is one of the most dangerous diseases facing mankind. Cancer eventually leads to the death of the patient in most cases. Although modern medicine has made great efforts to treat cancer, cancer is still an unsolved problem. Prostate cancer is one of the most common malignant tumors in elderly men. Worldwide, the incidence of prostate cancer ranks second among all malignant tumors in men. In the United States, the incidence of prostate cancer ranks first among all male malignancies, and the death rate ranks second. In our country, its incidence rate has leapt to the third among malignant tumors of the genitourinary system in recent years. Prostate cancer has few clinical symptoms in the early stage, and most patients have reached the advan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/08C07C311/14C07C311/19C07D333/34C07D213/70C07D233/84C07D261/10C07D295/26C07C307/02C07C307/10C07C237/44C07D307/24C07D309/08A61P35/00A61P35/02
CPCA61P35/00A61P35/02C07C237/44C07C307/02C07C307/10C07C311/08C07C311/14C07C311/19C07C2601/02C07C2601/04C07C2601/08C07C2601/14C07D213/70C07D233/84C07D261/10C07D295/26C07D307/24C07D309/08C07D333/34A61K31/167A61K31/277A61K31/426A61K31/4409A61K31/455C07C231/12C07C237/40C07C237/42C07C335/22C07D213/81C07D213/82
Inventor 杜武温坤任闻艾朝武李海波陈江李宇李兴海陈元伟
Owner HINOVA PHARM INC
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