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Novel pyrazolopyridine antineoplastic compound

A compound and selected technology, applied in the field of anti-tumor drugs, can solve the problems of unsatisfactory cancer patients

Inactive Publication Date: 2016-04-20
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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  • Novel pyrazolopyridine antineoplastic compound
  • Novel pyrazolopyridine antineoplastic compound
  • Novel pyrazolopyridine antineoplastic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] The preparation of embodiment 1 compound I-1

[0088]

[0089] Put in the raw material T-160g, add 250ml of methanol to dissolve it, and then slowly add 0.35 molar equivalent of NaBH 4 , keep the temperature below 10°C to obtain about 60.5g, yield 99.8%.

[0090]

[0091] Put in 260g of raw material T-260g, add 300ml of dichloromethane to dissolve it, then add 1.5 molar equivalent of triethylamine (TEA), place below 0°C, and dropwise add 1.5 molar equivalent (eq) of methanesulfonyl chloride. About 80 g was obtained after post-processing, and the yield was 96%.

[0092]

[0093] Put in 13.6g of raw material T-3, add 100ml of DMF, then add 1.0eq of T-4 and 1.5eq of cesium carbonate, and heat up to 100°C for reaction. About 8 g was obtained by post-processing column chromatography, and the yield was 42.37%.

[0094]

[0095] Put in 13.6g of raw material T-3, add 100ml of absolute ethanol, add 25ml of concentrated hydrochloric acid dropwise at low temperature...

Embodiment 2

[0096] The preparation of embodiment 2 compound 1-2

[0097] 3-Methyl-2-piperidin-4-yl-2H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

[0098]

[0099] Put in 1-10.5g of raw materials, add 10ml of absolute ethanol, add 1.5g of sodium hydroxide and dissolve it in water, and then add it to react at room temperature. After post-treatment, about 0.34 g was obtained, with a yield of 85%. 1 HNMR (DMSO-d 6 )δ9.45(br,1H),9.02(d,J=2Hz,1H),8.77(d,J=2Hz,1H),7.41(br,1H),5.19~5.11(m,1H),3.41~ 3.21(m,2H), 3.19~3.11(m,2H), 2.57(s,3H), 2.46~2.30(m,2H), 2.12~2.04(m,2H).m / z=261(M+H + ).

Embodiment 3

[0100] The preparation of embodiment 3 compound 1-3

[0101]

[0102] Add 10.29g of raw material I-7, 1.0eq of compound T-7, 1.5eq of amidation reaction catalyst HBTU, 1.5eq of TEA, and 10ml of DMF, and stir the reaction at room temperature for 24h. After post-treatment, about 0.21 g was obtained, with a yield of 46.67%. 1 HNMR (DMSO-d 6 )δ: 9.13(d, J=2Hz, 1H), 8.79(d, J=2Hz, 1H), 8.67(d, J=2Hz, 1H), 8.54(d, J=2Hz, 1H), 6.54(s ,1H),5.12(m,1H),4.42(m,2H),3.29~3.03(m,4H),2.60(s,3H),2.57(s,3H),2.46~2.30(m,2H), 2.12~2.04(m,2H),1.42(m,3H),.m / z=448(M+H + )

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Abstract

The invention provides a novel pyrazolopyridine antineoplastic compound with excellent antineoplastic activity. The antineoplastic compound is shown as the formula I, wherein M groups are freely selected from hydrogen atoms, alkyl groups and naphthenic groups, Y represents N atom site substituted or non-substituted nitrogen atom containing 5-8 membered rings, and the substituent group is a -X1 group or -CO2X2 or -COX3 or -CONHX4. The definitions of X1, X2, X3 and X4 are the same as definitions in the description. The invention further provides a preparation method of the antineoplastic compound and an application of the antineoplastic compound in antineoplastic drugs for lung cancer, colon cancer and ovarian cancer. The compound has good antineoplastic activity. The formula is shown in the description.

Description

technical field [0001] This field belongs to the field of anti-tumor drugs, and specifically relates to a novel anti-tumor compound or a pharmaceutically acceptable salt thereof and its preparation method and use. 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 attracted more and more at...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D519/00A61P35/00
CPCC07D471/04C07D519/00
Inventor 张孝清包金远宋志春翟洪
Owner NANJING HUAWE MEDICINE TECH DEV
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