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Tertiary amine-containing anthranilamide compound as well as preparation and application thereof

A technology of aminobenzamide and compound, which is applied in the field of medicine, can solve the problems of neutropenia and leukopenia, and achieve the effect of inhibiting proliferation, low toxicity and good pharmacokinetic performance

Active Publication Date: 2021-08-03
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the targets of CDK inhibitors on the market are all CDK4 / 6, which are all aimed at breast cancer, and they have adverse reactions such as neutropenia and leukopenia

Method used

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  • Tertiary amine-containing anthranilamide compound as well as preparation and application thereof
  • Tertiary amine-containing anthranilamide compound as well as preparation and application thereof
  • Tertiary amine-containing anthranilamide compound as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] pyridin-3-ylmethyl 4-(2-(ethyl(methyl)amino)benzamido)benzylcarbamate (Compound T1, R=NCH 3 (CH 2 CH 3 ), R 0 =H).

[0056] (1) Put pyridin-3-ylmethyl 4-aminobenzylcarbamate (1 mmol), o-iodobenzoic acid (1.2 mmol), HATU (1.2 mmol), DIPEA (1.3 mmol) into a 50ml round bottom flask and replace with argon . After adding 10ml of dry N,N-dimethylformamide as a solvent, triethylamine (2 mmol) was added dropwise and reacted at room temperature for 6 h. After the completion of the reaction monitored by TLC, the N,N-dimethylformamide was extracted and washed with water and ethyl acetate, the organic phase was collected and spin-dried, and the product pyridin-3-ylmethyl 4-(2-iodobenzamido)benzylcarbamate was obtained by column chromatography (Compound 2, R 1 =I,R 0 = H), productive rate 85%.

[0057] (2) Add pyridin-3-ylmethyl 4-(2-iodobenzamido)benzylcarbamate (1 mmol), N-methylethylamine (3 mmol), copper powder (0.01 mmol), cuprous bromide (0.01 mmol), carbonic acid Pot...

Embodiment 2

[0059] pyridin-3-ylmethyl 4-(2-(diethylamino)benzamido)benzylcarbamate (compound T2, R=N(CH 2 CH 3 ) 2 , R 0 =H).

[0060] The raw material N-methylethylamine in step (2) of Example 1 was replaced by diethylamine, and the rest of the steps were prepared in the same way as in Example 1, with a yield of 70%. 1 H NMR (400 MHz, DMSO- d 6 ) δ 13.01 (s, 1H), 8.64 – 8.25 (m, 2H), 8.08 (dd, J = 7.8, 1.6 Hz, 1H), 7.90 – 7.75 (m, 2H), 7.66 (d, J = 8.4 Hz,2H), 7.59 – 7.53 (m, 1H), 7.46 (d, J = 7.8 Hz, 1H), 7.40 (dd, J = 7.7, 4.9Hz, 1H), 7.35 – 7.29 (m, 1H), 7.26 (d, J = 8.4 Hz, 2H), 5.09 (s, 2H), 4.18(d, J = 6.1 Hz, 2H), 3.12 (q, J = 7.1 Hz, 4H), 0.96 (t, J = 7.1 Hz, 6H). 13 CNMR (101 MHz, DMSO- d 6) Δ 163.62, 156.15, 149.12, 149.06, 137.36, 135.70,134.69, 132.70, 132.28, 130.05, 129.85, 127.83, 125.05, 123.48,119.20, 63.13, 48.59, 42.506, 12.06, 12.06, 12.06, 12.06, 12.06, 12.06, 12.06, 12.06, 12.06, 12.06, 12.06, 12.06, 12.06, 12.06, 12.06, 12.06, 12.06, 12.06, 1...

Embodiment 3

[0062] pyridin-3-ylmethyl 4-(2-(dipropylamino)benzamido)benzylcarbamate (compound T3, R=N(CH 2 CH 2 CH 3 ) 2 , R 0 =H).

[0063] The raw material N-methylethylamine in step (2) of Example 1 was replaced by dipropylamine, and the remaining steps were prepared in the same way as in Example 1, with a yield of 75%. 1 H NMR (400 MHz, DMSO- d 6 ) δ 12.64 (s, 1H), 8.62 – 8.57 (m, 1H), 8.53 (dd, J = 4.7, 1.3 Hz, 1H), 8.01 (dd, J = 7.8, 1.6 Hz, 1H), 7.86 (t, J =6.1 Hz, 1H), 7.78 (d, J = 7.8 Hz, 1H), 7.66 (d, J = 8.4 Hz, 2H), 7.53 (td, J = 7.7, 7.3, 1.7 Hz, 1H), 7.46 – 7.37 (m, 2H), 7.30 – 7.21 (m, 3H), 5.09 (s,2H), 4.18 (d, J = 6.1 Hz, 2H), 3.07 – 2.96 (m, 4H), 1.41 (h, J = 7.4 Hz, 4H), 0.78 (t, J = 7.4 Hz, 6H). 13 C NMR (101 MHz, DMSO- d 6 ) Δ 164.01, 156.26, 149.63,149.23, 149.16, 137.73, 135.80, 134.77, 132.80, 132.16, 130.15, 129.60,127.89, 123.36, 123.50, 119.35, 56.80, 19.80, 1980, 19.56.80, 19.80, 19.80, 1980, 19.80, 1980, 19.80, 1980, 19.80, 1980, 1980,...

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Abstract

The invention provides a tertiary amine-containing anthranilamide compound as well as preparation and application thereof. The tertiary amine-containing anthranilamide compound can inhibit proliferation, migration and invasion of gastric cancer cells and induce apoptosis, and has a cycle arrest effect. The tertiary amine-containing anthranilamide compound has higher activity than 5-fluorouracil on the cellular level, has higher activity than capecitabine on the animal level, is effective in oral administration, has lower toxicity than capecitabine, and is safer and more effective. The compound has good pharmacokinetic performance and can be applied to preparation of anti-gastric cancer drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a tertiary amine-containing anthranilamide compound and its preparation and application. Background technique [0002] Tumor is the second killer that seriously threatens human life and health after cardiovascular and cerebrovascular diseases. In 2018, there were 18.1 million new cases of cancer worldwide and 9.6 million deaths from it. Among them, the incidence rate of gastric cancer ranks fifth, and the mortality rate ranks third. According to statistics, in 2018, there were 1.03 million new cases of gastric cancer worldwide and 783,000 deaths, which is equivalent to 1 case of gastric cancer in every 12 deaths caused by malignant tumors in the world. As a large gastric cancer country, China accounts for more than 40% of the total number of gastric cancer deaths in the world in the same period every year. The incidence of gastric cancer in China is second only to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/30C07D405/12A61P35/00A61K31/496A61K31/4406A61K31/444A61K31/4545A61K31/4427A61K31/4439A61K31/55A61K31/5377
CPCC07D213/30C07D405/12A61P35/00
Inventor 王震石桃冯益悦卢莹美李俊芳张红花
Owner NANHUA UNIV
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