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Piperazine substituted pyrimidine compounds and applications thereof

A technology for compounds and pyrimidines, applied in the field of pharmaceutical preparation, can solve problems such as poor absorption, low bioavailability of compounds, and effects on curative effects.

Inactive Publication Date: 2014-10-01
黄传满
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has been reported in the literature that XL-418 has strong anti-tumor activity and can be used to treat solid tumors such as lung cancer and prostate cancer (BMCL2012, 22, 2693-2697). 21); however, the bioavailability of the above-mentioned compounds is not high, and the absorption in the body is poor, which affects the curative effect in the human body

Method used

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  • Piperazine substituted pyrimidine compounds and applications thereof
  • Piperazine substituted pyrimidine compounds and applications thereof
  • Piperazine substituted pyrimidine compounds and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 Synthesis of 2-piperazine-3-trifluoromethyl-pyridine (compound 2)

[0022] Add 2-chloro-3-trifluoromethyl-pyridine (3.0g, 16.5mmol), anhydrous piperazine (12g, 139mmol) and n-butanol (10mL) into the reaction flask, stir, heat to reflux for 6 hours, cool , concentrated, extracted with dichloromethane (150mL), washed twice with water (30mL), dried over anhydrous sodium sulfate, and concentrated to give a light yellow oil, which was quickly passed through the column (eluent: dichloromethane / Methanol=20 / 1), 2.8 g of light yellow oily substance 2-piperazine-3-trifluoromethyl-pyridine was obtained, and a low-melting solid was obtained the next day, yield: 73.6%.

[0023] 1 H-NMR (CDCl 3 , 400MHz): δ8.46~8.44(m, 1H), 7.89~7.87(m, 1H), 7.02~6.99(m, 1H), 3.47~3.31(m, 4H), 3.09~3.06(m, 4H) .

Embodiment 2

[0024] Example 2 Synthesis of 3-bromo-4-[4-(3-trifluoromethyl-pyridine)-2-piperazine)-pyrazolopyrimidine (compound 3)

[0025] Add 3-bromo-4-chloropyrazolopyrimidine (140mg, 0.60mmol), 2-piperazine-3-trifluoromethyl-pyridine (166mg, 0.72mmol), triethylamine (0.5mL) and Dioxane (10mL), the oil bath was slowly warmed to 80°C, stirred for 3 hours, cooled to room temperature, concentrated to dryness, added water (10mL), shaken, filtered with suction, washed with water, and dried to obtain a white solid 3-bromo -4-[4-(3-trifluoromethyl-pyridine)-2-piperazine)-pyrazolopyrimidine 193 mg, yield: 75.1%.

[0026] 1 H-NMR (DMSO-d6, 400MHz): δ14.06(br, 1H), 8.57(d, 1H), 8.37(s, 1H), 8.13(d, 1H), 7.27~7.24(m, 1H), 3.95~3.92(m, 4H), 3.40~3.37(m, 4H).

Embodiment 3

[0027] Example 3 Synthesis of 1-isopropyl-3-bromo-4-[4-(3-trifluoromethyl-pyridine)-2-piperazine)-pyrazolopyrimidine (compound 4)

[0028] Add 3-bromo-4-[4-(3-trifluoromethyl-pyridine)-2-piperazine)-pyrazolopyrimidine (170mg, 0.40mmol), anhydrous potassium carbonate (110mg, 0.80mmol) into the reaction flask ) and DMF (3mL), heated to 55°C and stirred for half an hour, added bromoisopropane (98mg, 0.80mmol), and reacted at this temperature for 3 hours, cooled, added water (10mL), shaken, suction filtered, washed with water , dried to obtain 151 mg of off-white solid 1-isopropyl-3-bromo-4-[4-(3-trifluoromethyl-pyridine)-2-piperazine)-pyrazolopyrimidine, yield: 80.3%.

[0029] 1 H-NMR (DMSO-d6, 400MHz): δ8.57(d, 1H), 8.39(s, 1H), 8.13(d, 1H), 7.27~7.24(m, 1H), 5.09~5.06(m, 1H) ), 3.97~3.94(m, 4H), 3.39~3.37(m, 4H), 1.46(d, 6H).

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Abstract

The invention provides piperazine substituted pyrimidine compounds represented by the formula I and applications thereof. The pyrimidine compounds represented by the formula I have a prominent inhibiting effect on human lung cancer cells, human stomach cancer cells, human prostatic cancer cells, human colon cancer cells, human kidney cancer cells, and myeloma cells, and can be used to prepare drugs for treating human lung cancer, human stomach cancer, human prostatic cancer, human colon cancer, human kidney cancer, and myeloma.

Description

technical field [0001] The invention relates to piperazine-substituted pyrimidine compounds and uses thereof, belonging to the technical field of medicine preparation. Background technique [0002] Malignant tumor is a major disease that endangers people's life and health. Tens of millions of people die from cancer every year in the world. The research and development of anti-tumor drugs has a long way to go. The development of new, efficient and low-toxic anti-tumor drugs has become a top priority. [0003] Pyrimidine compounds have shown good pharmacological activity in medical research and can be used for the treatment of various tumors. It has been reported in the literature that XL-418 has strong anti-tumor activity and can be used to treat solid tumors such as lung cancer and prostate cancer (BMCL2012, 22, 2693-2697). 21); however, the bioavailability of the above-mentioned compounds is not high, and the absorption in the body is poor, which affects the curative effec...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61P35/00
CPCC07D487/04
Inventor 黄传满解美娜
Owner 黄传满
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