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Carbamate compound and application thereof in antitumor drug

A technology of phenylcarbamate and compound, applied in the field of medicine, can solve the problems of low oral bioavailability, affecting drug absorption and utilization, etc.

Active Publication Date: 2013-01-30
NANJING SANHOME PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a multi-target drug, Sorafenib has the function of inhibiting a wide range of tyrosine kinase receptors including VEGFR and PDGFR, but the oral bioavailability of Sorafenib is low, which affects the absorption and utilization of the drug

Method used

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  • Carbamate compound and application thereof in antitumor drug
  • Carbamate compound and application thereof in antitumor drug
  • Carbamate compound and application thereof in antitumor drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Example 1: Benzyl-4-(2-(methylcarbamoyl)pyridin-4-oxyl)phenylcarbamate (SH-007)

[0089]

[0090] Weigh 0.710g (0.003 mol) of 4-(4-aminophenoxy)-N-methylpicolinamide into a 100 ml three-neck round bottom flask, add 20 ml of dichloromethane and stir to dissolve, then add 0.4 ml of triethyl amine, under ice bath, slowly add 0.4ml of benzyl chloroformate dropwise, after the dropwise addition, react at room temperature for 1 h, wash with water, extract the organic layer, and separate by column chromatography (eluent: petroleum ether / ethyl acetate = 1: 1), a white solid was obtained. Melting point: 119.2-120.2°C.

[0091] 1 H NMR (CDCl 3 ) δ (ppm): 8.37 ~ 8.35 (d, 1H, pyridine- H ), 8.01 (s, 1H, N H CO), 7.70 (s, 1H, pyridine- H ), 7.47 ~ 7.34 (m, 7H, Ar- H, ), 7.05 ~ 7.02 (d, 2H, Ar- H ), 6.95 ~ 6.92 (m, 1H, pyridine- H ), 6.79 (s, 1H, N H CO), 5.22 (s, 2H, C H 2 ), 3.01 ~ 3.00 (d, 3H, CH 3 ).

[0092] ESI-MS m / z: 378 (M+1) + , calculated value: 378

Embodiment 2

[0093] Example 2: Benzyl-2-methyl-4-(2-(methylcarbamoyl)pyridin-4-oxyl)phenylcarbamate (SH-019)

[0094]

[0095] Using the method of Example 1, 4-(4-aminophenoxy)-N-picolinamide is replaced with 4-(4-amino-3-methylphenoxy)-N-picolinamide, The target compound was obtained as off-white solid. Melting point: 144.4-144.7°C.

[0096] 1 H NMR (CDCl 3 ) δ (ppm): 8.37 ~ 8.35 (d, 1H, pyridine- H ), 8.04 (s, 1H, N H CO), 7.87 ~ 7.84 (s, 1H, N H CO), 7.70 ~ 7.69 (s, 1H, pyridine- H ), 7.44 ~ 7.33 (m, 5H, Ar- H ), 6.96 ~ 6.90 (m, 3H, Ar- H , pyridine- H ), 6.46 (s, 1H, Ar- H ), 5.22 (s, 2H, C H 2 ), 3.01 ~ 3.00 (d, 3H, C H 3 ), 2.25 (s, 3H, C H 3 ).

[0097] ESI-MS m / z: 392 (M+1) + , calculated value: 392.

Embodiment 3

[0098] Example 3: Benzyl-2-chloro-4-(2-(methylcarbamoyl)pyridin-4-oxyl)phenylcarbamate (SH-020)

[0099]

[0100] Using the method of Example 1, 4-(4-amino-3-chlorophenoxy)-N-methylpicolinamide is replaced by 4-(4-aminophenoxy)-N-methylpicolinamide to obtain this The target compound, a brownish-yellow solid. Melting point: 133.4-134.7°C.

[0101] 1 H NMR (CDCl 3 ) δ (ppm): 8.40 ~ 8.38 (d, 1H, pyridine- H ), 8.27 ~ 8.25 (d, 1H, N H CO), 8.00 (s, 1H, N H CO), 7.70 ~ 7.69 (d, 1H, pyridine- H ), 7.45 ~ 7.35 (m, 5H, Ar- H ), 7.17 (s, 1H, Ar- H ), 7.14 ~ 7.13 (d, 1H, Ar- H ), 7.04 ~ 7.02 (m, 1H, Ar- H ), 6.96 ~ 6.94 (m, 1H, pyridine- H ), 5.24 (s, 2H, C H 2 ), 3.01 ~ 3.00 (d, 3H, C H 3 ).

[0102] ESI-MS m / z: 412 (M+1) + , calculated value: 412.

[0103]

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Abstract

The present invention relates to a carbamate compound. The compound can block the formation of tumor new vessels by inhibiting a VEGF receptor and can also inhibit the Raf / MEK / ERK signal conduction path so as to achieve the effect of treatment of cancer. The present invention also relates to a preparation method of the compounds and application thereof in treatment or prevention of tumors, or in preparing a pharmaceutical composition for treating or preventing tumors.

Description

technical field [0001] The invention belongs to the field of medicine, and specifically relates to carbamate compounds and a preparation method thereof, and also relates to the application of such compounds in treating cancer. Background technique [0002] Tumors are diseases characterized by the uncontrolled proliferation and spread of abnormal cells. The body's internal factors (hormones, immune status, genetic variation) and external factors (chemical, optical factors and viruses) may be carcinogenic factors. With the deterioration of the environment and the continuous increase of people's work pressure, cancer has gradually become the cause of human death. One of the main killers. According to the statistics of the American Cancer Society, in 2007, 7.6 million people died of malignant tumors in the world; 12.3 million new cancer cases and nearly 45 million existing cases. Cancer has become the number one cause of death in developed countries, accounting for 21.6% of the...

Claims

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Application Information

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IPC IPC(8): C07D213/81A61K31/44A61P35/00A61P35/02
Inventor 王勇张仓张小猛唐海涛张文萍
Owner NANJING SANHOME PHARMACEUTICAL CO LTD
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