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Pyrazolopyridine derivative anti-tumor compound and preparation method and application thereof

A technology of compounds and hydrates, applied in the field of anti-tumor drugs, can solve problems such as inability to meet cancer patients

Active Publication Date: 2016-01-20
NANJING HUAWE MEDICINE TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing anti-tumor drugs are still far from meeting the growing needs of cancer patients, and anti-tumor drugs are still an important direction for research and development

Method used

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  • Pyrazolopyridine derivative anti-tumor compound and preparation method and application thereof
  • Pyrazolopyridine derivative anti-tumor compound and preparation method and application thereof
  • Pyrazolopyridine derivative anti-tumor compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] The preparation of embodiment 1 compound I-1

[0078] first step:

[0079]

[0080] Add 40g of raw material i into a 2L single-necked bottle, add 800mL of dichloromethane to dissolve it, then add 38.6g of triethylamine, add 32.6g of methanesulfonyl chloride dropwise at low temperature, and return to room temperature for reaction after dropping. After the reaction was completed, it was washed twice with 1 mol / L hydrochloric acid, once with saturated sodium chloride, dried over anhydrous sodium sulfate, and spin-dried to obtain 55 g of a brown-red oily liquid.

[0081] Step two:

[0082]

[0083] Add 64.6g of intermediate II and 180ml of DMF into a 2L single-necked bottle, add 41.6g of III after dissolving, then add 74g of cesium carbonate, and heat the oil bath until the external temperature is 105°C. After the reaction was completed, a large amount of water was added, extracted with ethyl acetate, spin-dried and separated by column chromatography to obtain 50 g ...

Embodiment 2

[0092] The preparation of embodiment 2 compound Ⅰ-2

[0093]

[0094] Add 1.0g of intermediate VI and 0.62g of cyclopropyl-piperazin-1-yl-methyl ketone into a 100mL one-necked bottle, then add 10mL of DMF and stir to dissolve, then add 2.05g of HBTU, 0.82g of triethylamine, and react at room temperature for 5h . After the reaction, the reaction solution was poured into water, extracted with ethyl acetate, dried with anhydrous sodium sulfate and spin-dried, and separated by column chromatography to obtain 1.1 g of solid.

[0095] 1 HNMR(DMSO-d6)δ:8.34(1H,s),8.05(1H,s),7.18~7.15(1H,m),6.97~6.92(1H,m),6.51~6.46(1H,q),3.67 ~3.60(8H, m), 2.54(3H, s), 2.11(3H, d, J=7.2Hz), 1.66~1.64(1H,m), 0.94~0.86(2H,m), 0.73~0.71(2H ,m).

[0096] m / z=505(M+H+)

[0097] The preparation of Examples 3-32 refers to the process route above in the specification, and the preparation process of the compound is similar to that of Example 1 and Example 2. Table 1 below shows the test data of the e...

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Abstract

The invention provides a pyrazolopyridine derivative anti-tumor compound with the excellent anti-tumor activity. The anti-tumor compound is shown by the formula I, wherein Y represents halogen, X represents -NHX2 or amino acid residues or the formula shown in the specification, and the definitions of R1, R2 and X2 are the same as those in the specification. The invention further provides a preparation method of the anti-tumor agent shown in the formula I and application of the pyrazolopyridine derivative anti-tumor compound in anti-tumor drugs of the lung cancer, the colon cancer and the ovarian cancer.

Description

technical field [0001] This field belongs to the field of antitumor drugs, and specifically relates to a pyrazolopyridine antitumor compound or a pharmaceutically acceptable salt thereof, a preparation method and application thereof. Background technique [0002] Tumor is still one of the most common and serious diseases that directly threaten human life in the world today, and its incidence rate is second only to cardiovascular diseases. At present, tumor chemotherapy has made some progress, which significantly prolongs the survival time of patients, but still has not achieved satisfactory curative effect. In recent years, the in-depth research on the molecular level of oncology and tumor lesions and the discovery of many new therapeutic targets have provided the possibility for the development of new anti-tumor drugs. With the continuous deepening of the research on the signal transduction pathway of tumor cells, the design and research of new anti-tumor drugs have attrac...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00A61K31/437A61K31/496A61K31/444A61K31/5377A61K31/506A61P35/00
CPCC07D471/04C07D519/00
Inventor 张孝清宋志春包金远蒋玉伟
Owner NANJING HUAWE MEDICINE TECH DEV
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