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Aryl carboxylic acid imatinib derivative as well as preparation and application thereof

A technology of aryl carboxylic acid and imatinib, which is applied in the field of derivatives with anti-tumor activity and their preparation, can solve the problems of no anti-tumor application, poor anti-chronic myeloid leukemia activity, and the like, and achieves structural Novel, obvious inhibitory effect, mild synthesis conditions

Inactive Publication Date: 2013-05-29
安徽安生生物化工科技有限责任公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chinese patent CN1800195A synthesized carboxylic acid non-steroidal anti-inflammatory drugs and glucosamine compounds in anti-inflammation, but no application in anti-tumor
Among them, the patent CN102212057A uses the combination principle to combine imatinib intermediate 2-[N-(2-methyl-5-aminophenyl)amino]-4-(3-pyridyl)pyrimidine and carboxylic acid non-steroidal compounds A series of imatinib analogs are obtained by linking with amide bonds, but the anti-chronic myelogenous leukemia activity of these compounds is not very good, all of which are lower than imatinib

Method used

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  • Aryl carboxylic acid imatinib derivative as well as preparation and application thereof
  • Aryl carboxylic acid imatinib derivative as well as preparation and application thereof
  • Aryl carboxylic acid imatinib derivative as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 (E)-3-(4-trifluoromethylphenyl)-N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidine-2-amino))benzamide

[0026]

[0027] Weigh 4-trifluoromethylbenzoic acid (2.67 g, 15 mmol) and dissolve it in 30 mL of dichloromethane, add oxalyl chloride (2.20 g, 18 mmol) dropwise under ice-cooling, stir at room temperature for 3 h, and 2- [N-(2-Methyl-5-aminophenyl)amino]-4-(3-pyridyl)pyrimidine (3.78 g, 13.5 mmol) was dissolved in 30 mL of dichloromethane and added to it. After 8 hours of reaction, the reaction was complete , filtered, collected the solid matter, and washed three times with dichloromethane to obtain 5.61 g of off-white solid with a yield of 84.2% and a melting point of 218-220 °C. The NMR data of the product are as follows: 1 H NMR (300 MHz, DMSO-d 6 )δ: 10.49 (s, 1H); 9.28 (s, 1H); 9.00 (s, 1H); 8.69-8.68 (t, 1H, J=4.4Hz); 8.54-8.45 (m, 2H); 8.16-8.12 (t, 3H, J=16.4Hz); 7.92-7.90 (d, 2H, J=8.4Hz); 7.55-7.50(m, 2H); 7.45-7.43(d, 1H, J=5.2Hz); 7.24- 7.22(d, 1...

Embodiment 2

[0028] Example 2 N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidine-2-amino))-(4-methylphenyl)formamide

[0029]

[0030] The operation steps are the same as in Example 1, except that 4-methylbenzoic acid is used instead of 4-trifluoromethylbenzoic acid. The target product is a light yellow solid with a yield of 84.7% and a melting point of 211-213 ℃. The NMR data of the product are as follows: 1 H NMR (300 MHz, DMSO-d 6 )δ: 10.14 (s, 1H); 9.27 (s, 1H); 9.07-8.94 (m, 1H); 8.73 (s, 1H); 8.54-8.49 (m, 2H); 8.10-7.01 (m, 2H) ;7.88-7.85(t, 1H, J=12.0Hz); 8.53-7.32(m, 5H); 7.23-7.20(d, 1H, J=10.4Hz); 2.38(s, 3H); 2.23(s, 3H ).

Embodiment 3

[0031] Example 3 N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidine-2-amino))-(4-nitrophenyl)formamide

[0032]

[0033] The operation steps are the same as in Example 1, except that 4-nitrobenzoic acid is used instead of 4-trifluoromethylbenzoic acid. The target product is a brown solid with a yield of 82.5% and a melting point of 253-258°C. The NMR data of the product are as follows: 1 H NMR (400 MHz, DMSO-d 6 )δ: 10.63 (s, 1H); 9.45 (s, 1H); 9.22 (s, 1H); 9.08-9.01 (m, 3H); 8.72-8.70 (d, 2H, J=8.4Hz); 8.11-7.01 (m, 3H); 7.62-7.50 (m, 3H); 7.26-7.25 (d, 1H, J=6.4Hz); 2.26 (s, 3H).

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Abstract

The invention provides a derivative which is shown in the formula (I) in the specification and is obtained by reacting an aryl carboxylic acid derivative with 2-[N-(2-methyl-5-amino phenyl)amino]-4-(3-pyridine)pyrimidine. The derivative has the anti-tumor activity and has a better suppression function to a chronic myeloblastic leukemia cell strain K562, a non-small cell lung cancer cell strain A549 and a galactophore cancer cell strain MDA-MB-45.

Description

technical field [0001] The present invention relates to a kind of pharmaceutical compound, specifically is made up of aryl carboxylic acid compound and imatinib intermediate 2-[N-(2-methyl-5-aminophenyl)amino]-4-(3 Derivatives with antitumor activity obtained by reaction of -pyridyl)pyrimidine and preparation method thereof. technical background [0002] The combination principle mainly refers to the combination of the structures of two drugs in one molecule, or the compatibility of the pharmacophore of the two in one molecule, which is called a hybrid molecule, and the newly formed hybrid molecule may have the properties of both. , to strengthen the pharmacological effects and reduce their corresponding toxic and side effects; or to make the two complement each other, exert their respective pharmacological activities, and complete the treatment process synergistically (Drug Design, 2001: 88-91). Aryl carboxylic acid compounds are a large class of non-steroidal anti-inflamm...

Claims

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Application Information

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IPC IPC(8): C07D401/04A61K31/506A61P35/00A61P35/02
Inventor 姚日生陆小琴阮班锋邓胜松段红玉张遥
Owner 安徽安生生物化工科技有限责任公司
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