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Amine pyrimidine derivates, and production method thereof, and medicament composition and use

A technology of anilinopyrimidine and pyrimidine, applied in the field of aminopyrimidine derivatives

Inactive Publication Date: 2009-05-06
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Although many small molecule tyrosine kinase inhibitors have been discovered and have made great contributions to the field, research in the field continues to improve anticancer drugs

Method used

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  • Amine pyrimidine derivates, and production method thereof, and medicament composition and use
  • Amine pyrimidine derivates, and production method thereof, and medicament composition and use
  • Amine pyrimidine derivates, and production method thereof, and medicament composition and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Example 1. N-(4-(pyridin-3-yl)pyrimidin-2-yl)-N-(2-methyl-5-nitrophenyl)acetamide

[0092]

[0093] Place 307mg of 4-(pyridin-3-yl)-2-(2-methyl-5-nitroanilino)pyrimidine in a 50ml flask, add 30ml of acetic anhydride and 100mg of anhydrous sodium acetate, and heat to 70oC After stirring for 5 hours, the acetic anhydride was removed under reduced pressure, 20 ml of water was added and extracted with ethyl acetate, washed with water, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was removed to obtain N-(4-(pyridine-3 -yl)pyrimidin-2-yl)-N-(2-methyl-5-nitrophenyl)acetamide. 1 H NMR (300M, CDCl 3 ), δ (ppm) 9.12 (S, 1H, ArH), 8.65 (d, 1H, ArH), 8.62 (d, 1H, ArH), 8.17 (m, 1H, ArH), 8.10 (dd, 1H, ArH) , 8.02(d, 1H, ArH), 7.47(d, 1H, ArH), 7.43(d, 1H, ArH), 7.38(dd, 1H, ArH), 2.61(S, 3H, -COCH 3 ), 2.25 (S, 3H, -CH 3 ).FABMS: (M+H) + =350.

Embodiment 2

[0094] Example 2. N-(4-(pyridin-3-yl)pyrimidin-2-yl)-N-(2-methyl-5-aminophenyl)acetamide

[0095]

[0096] Place 349 mg of N-(4-(pyridin-3-yl)pyrimidin-2-yl)-N-(2-methyl-5-nitrophenyl)acetamide in a 100 ml flask, add 50 ml of methanol and 35 mg of 10% Pd / C, filtered after hydrogenation at normal pressure for 5 hours, and the solvent was spun off to obtain N-(4-(pyridin-3-yl)pyrimidin-2-yl)-N-(2-methyl-5 -aminophenyl)acetamide. 1 H NMR (300M, DMSO-d), δ (ppm) 9.27 (S, 1H, ArH), 8.82 (d, 1H, ArH), 8.72 (S, 1H, ArH), 8.46 (d, 1H, ArH), 7.97(d, 1H, ArH), 7.58(m, 1H, ArH), 6.95(d, 1H, ArH), 6.47(d, 1H, ArH), 6.39(dd, 1H, ArH), 2.32(S, 3H ,-COCH 3 ), 1.98 (S, 3H, -CH 3 ).FABMS: (M+H) + =320.

Embodiment 3

[0097] Example 3.N-[3-(acetyl-(4-pyridin-3-yl-pyrimidin-2-yl)amino)-4-methylphenyl]-3-acetamidobenzamide

[0098]

[0099] Dissolve 319 mg of N-(4-(pyridin-3-yl)pyrimidin-2-yl)-N-(2-methyl-5-aminophenyl)acetamide and 197 mg of 3-acetamidobenzoyl chloride in In 20 ml of anhydrous pyridine, stirred at room temperature for 12 hours, removed the solvent under reduced pressure, added ethyl acetate to dissolve, washed with saturated sodium bicarbonate solution, washed with water, washed with saturated brine, dried overnight with anhydrous sodium sulfate, spun to remove the solvent, and the column After chromatographic separation, N-[3-(acetyl-(4-pyridin-3-yl-pyrimidin-2-yl)amino)-4-methylphenyl]-3-acetamidobenzamide was obtained. 1 H NMR (300M, DMSO-D6), δ (ppm) 10.25 (S, 1H, N-H), 10.12 (S, 1H, N-H), 9.30 (d, 1H, ArH), 8.84 (d, 1H, ArH), 8.76(dd, 1H, ArH), 8.50(d, 1H, ArH), 8.02(m, 2H, ArH), 7.68(m, 2H, ArH), 7.59(m, 2H, ArH), 7.41(t, 1H , ArH), 7.32 (d, 1H, ArH), 7.80 (dd, 1H...

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Abstract

The invention discloses an aminopyrimidine derivative shown in general formula I, medicinal salt thereof, hydrate and solvate thereof, polycrystal and eutectic crystal thereof, a precursor or a derivative with the same biological function thereof, a preparation method thereof, a composition containing one or a plurality of the compounds, and application of the compound in treating diseases related to protein-tyrosine kinase, such as immunity imbalance and neoplastic diseases.

Description

technical field [0001] The present invention relates to aminopyrimidine derivatives represented by general formula I, their pharmaceutically acceptable salts, their hydrates and solvates, their polycrystals and cocrystals, their precursors or derivatives with the same biological function, and their preparation methods , a composition containing one or more of these compounds, and uses of such compounds in treating diseases associated with protein tyrosine kinases, such as immune disorders and tumor diseases. Background technique [0002] Currently, cancer is still one of the deadliest diseases. Chemotherapy is an important means to inhibit tumor growth and cancer cell proliferation, and make tumor regression. Most of the traditional chemotherapeutic drugs are cytotoxic drugs that directly attack DNA or inhibit its synthesis and function. They kill both cancer cells and normal cells. They are only effective for fast-growing tumors and have strong side effects. In order to in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D401/14A61K31/506A61P35/00
Inventor 冯志强陈晓光刘鹤孟畅左明新
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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