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Oxime compounds, preparation method and application thereof

A compound and pharmaceutical technology, applied in the field of medicine, can solve problems such as damage, mutagenesis, and side effects

Inactive Publication Date: 2011-12-28
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chemotherapy is faster, but the cure rate is very low
At the same time, it is clinically found that many anticancer drugs have obvious damage and side effects on the normal body, such as mutagenesis and genotoxicity

Method used

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  • Oxime compounds, preparation method and application thereof
  • Oxime compounds, preparation method and application thereof
  • Oxime compounds, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0060] Intermediate IV-1

[0061]

[0062] Add 13.9 g of intermediate III-1 to a reaction flask equipped with a stirring, condenser, and thermometer, dissolve it with 40 mL of dichloromethane, and add 17.8 g of NBS while stirring. React under light at room temperature for 6 hours (the plate layer shows that the reaction is complete). with 3 x 30mL 35% Na 2 S 2 o 3 The reaction liquid was washed with aqueous solution, and the dichloromethane layer was fully dried with anhydrous sodium sulfate, filtered, and the dichloromethane was evaporated under reduced pressure to obtain a light yellow oily product (HPLC: 97.2%). Rf = 0.35 [single site, developing solvent: v (dichloromethane): v (methanol) = 6: 1]. 1 H NMR (DMSO-d 6 , 400MHz) δ: 2.324 (s, 1H, -OH), 7.572-7.961 (m, 4H, phenyl-H).

[0063] Referring to the method of Reference Example 2, intermediates IV-2 to IV-7 can be synthesized.

[0064]

[0065]

Embodiment 1

[0067] (5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2-(4H)-onyl)-(2-chlorophenyl)methanone oxime (compound 1)

[0068]

[0069] Add 2.2g of intermediate IV-1 into a reaction flask equipped with stirring, condenser and thermometer, dissolve it with 10mL of anhydrous methanol, and add 2.76g of anhydrous potassium carbonate while stirring. 1.6 g of 5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2-(4H)-one was added to the reaction system in batches. After the addition was completed, the reaction was continued for 3.5h under reflux (the plate showed that the reaction was complete). Filter out the solid matter, evaporate anhydrous methanol to dryness, wash the reaction solution with 3×10 mL water, extract with dichloromethane, dry thoroughly with anhydrous sodium sulfate, filter, and evaporate dichloromethane under reduced pressure to obtain a black oil. Column separation [mobile phase: v (dichloromethane): v (methanol) = 9: 1], Rf = 0.45, gave a light yellow solid (HPLC: 99.3%). 1 H NMR...

Embodiment 3

[0075] (5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2-(4H)-onyl)-(2,5-dichlorophenyl)-O-ethyl ketone oxime (compound 3)

[0076]

[0077] Add 2.2 g of intermediate IV-3 to a reaction flask equipped with stirring, a condenser, and a thermometer, dissolve it with 20 mL of ethyl acetate, and add 1.0 g of sodium hydroxide while stirring. 1.6 g of 5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2-(4H)-one was added to the reaction system in batches. After the addition was completed, the reaction was continued for 8h under reflux (the plate showed that the reaction was complete). Filter off the solid matter, wash the reaction solution with 3×20 mL of water, dry it thoroughly with anhydrous sodium sulfate, filter, and evaporate the ethyl acetate under reduced pressure to obtain a yellow oil, which is separated by column [mobile phase: v (dichloromethane): v(methanol)=6:1], Rf=0.50, a white solid was obtained (HPLC: 99.8%).

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Abstract

The invention discloses oxime compounds with a structure as shown in formula I and pharmaceutically acceptable salt thereof. In the formula I, R1 is halogen; R2, R3 and R4 are simultaneously or respectively hydrogen, C1-C4 alkyl, C1-C4 alkoxy, halogen, nitryl, nitrile and phyenyl; R5 is hydrogen, C1 to C4 straight-chain or branch chain alkyl, and phenyl substituted by halogen, nitryl, nitrile, C1to C4 alkyl, C1 to C4 alkoxy, amido and alkanolamide. The invention also discloses a preparation method for the compounds, a medicinal composition using the compounds or the pharmaceutically acceptable salt thereof as an active effective component, and application of the compounds or the pharmaceutically acceptable salt thereof in serving as anti-tumor medicament, particularly in preparing medicament for treating breast cancer, lung cancer and gastric cancer.

Description

technical field [0001] The invention belongs to the technical field of medicine, more specifically, relates to a class of compounds with anti-tumor effect and their preparation method and application. Background technique [0002] Cancer has become a major chronic disease that seriously endangers human health. According to statistics, there are 9 million people who suffer from cancer every year in the world, and 6 million patients die from cancer. Almost one cancer patient dies every second. The annual incidence of cancer in my country is about 1.2 million, the number of cancer deaths is as high as more than 900,000, and the number of patients waiting for treatment exceeds 1.5 million, and there is an increasing trend year by year. Therefore, cancer has become the second largest killer after cardiovascular disease. Clinically, tumors are treated in three major ways: surgery, radiotherapy, and chemotherapy. Although the chemotherapy method is quicker, the cure rate is very...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61P35/00A61K31/4365C07D495/04
Inventor 刘颖刘冰妮刘默刘登科黄长江支爽龙丽陈旭汤立达
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH