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Novel anti-tumor compound

A technology of compounds and hydrates, applied in the direction of antineoplastic drugs, active ingredients of heterocyclic compounds, drug combinations, etc., can solve problems such as 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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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] The preparation of embodiment 1 compound I-1

[0104]

[0105] Throw T-160g, add 250ml methanol to dissolve, then slowly add NaBH 4 , keeping the temperature below 10° C., TLC monitored the complete reaction of the raw materials to obtain about 60.5 g, with a yield of 99.8%.

[0106]

[0107] Throw T-260g, add dichloromethane to dissolve, then add triethylamine, place below 0°C, add MeSO2Cl dropwise, TLC monitors the reaction of raw materials is complete. About 80 g was obtained after post-processing, and the yield was 96%.

[0108]

[0109] Throw in 13.6g of T-3, dissolve it with 100ml of DMF, then add 1.0eq of compound T-4 and 1.5eq of cesium carbonate, heat up to 100°C for reaction, and monitor the complete reaction of raw materials by HPLC. About 8 g of T-5 was obtained by column chromatography, with a yield of 42.37%.

[0110]

[0111] Throw 4g of T-5, dissolve it with 40ml of ethanol, add 40ml of water and 2eq of sodium hydroxide, stir at room tempe...

Embodiment 2

[0118] The preparation of embodiment 2 compound 1-2

[0119]

[0120] Throw 0.31g of T-6, add 20ml of DMF to dissolve, 1.5eq of methylamine hydrochloride, 3eq of triethylamine and 1.5eq of HBTU, stir and react at room temperature for 24h, TLC detects that the reaction is complete, pour the reaction into 200ml of water, acetic acid Extracted with ethyl ester, dried with anhydrous sodium sulfate, filtered, spin-dried, passed through the column to obtain 0.21 g of white solid, yield 71%

[0121]

[0122] Throw 0.21g of T-7, dissolve it with 5ml of methanol, add 2ml of concentrated hydrochloric acid, stir at room temperature for 3 hours, TLC detects that the raw materials have reacted completely, spin dry, add water to dissolve, adjust the pH value to 8-9, extract with ethyl acetate, and dry with anhydrous sodium sulfate , filtered and spin-dried to obtain 0.12 g of a white solid, with a yield of 80%.

[0123] 1 HNMR(DMSO-d6)δ:9.04(d,J=2Hz,1H),8.75(d,J=2Hz,1H),5.80~5.63(br...

Embodiment 3

[0125] The preparation of embodiment 3 compound 1-3

[0126]

[0127] Add compound T-58g, add 40ml of absolute ethanol, add 16ml of concentrated hydrochloric acid, stir at room temperature for 6 hours, TLC detects that the raw materials have reacted completely, spin dry, add water to dissolve, adjust the pH value to 8-9, extract with ethyl acetate, anhydrous sodium sulfate After drying, filtering and spin-drying, 5.4 g of white solid was obtained, with a yield of 85%.

[0128]

[0129] Throw C-12.9g, dissolve with 30ml of DMSO, then add 1.5eq of potassium carbonate, 0.1eq of potassium iodide, 1.2eq of bromoethane and 0.1eq of tetrabutylammonium bromide, stir the reaction at 60°C, after Workup yielded about 1.9 g, yield 60.1%.

[0130]

[0131]Throw 1.5g of C-2, dissolve it with 20ml of ethanol, add 20ml of water and 2eq of sodium hydroxide, stir at room temperature for 12h, TLC detects that the reaction is complete, add 200ml of water, adjust the pH value to 5-6, a l...

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Abstract

The invention provides a pyrazolopyridine derivative anti-tumor compound with excellent anti-tumor activity. The anti-tumor compound is shown as a formula I, wherein X represents -NH2, -NHOH, -NHX<1>, amino acid residue and the like (shown as the accompanying diagram); Y represents hydrogen atoms, alkyl groups, naphthenic bases, benzyl groups, aryl groups, heteroaryl, alkyl amino groups, -COX2 or -CONHX3, wherein the aryl group, the heteroaryl and the alkyl group are respectively, independently and randomly substituted by one or a plurality of materials from halogen, trifluoromethyl, amino groups, alkyl amino groups, hydroxyl, hydroxyalkyl, alkoxy, cyanogroup, nitryl, aryl groups and heteroaryl; the definitions of R1, R2, X1 and X2 are identical to the definitions in the specifications. The invention also provides a preparation method of an anti-tumor agent and application of the anti-tumor agent to lung cancer, colon cancer and ovarian cancer anti-tumor medicine.

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 application. 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/4545A61K31/55A61K31/46A61K31/5377A61P35/00
CPCC07D471/04
Inventor 张孝清宋志春包金远黄辉
Owner NANJING HUAWE MEDICINE TECH DEV
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