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A kind of preparation method of cyclopyridone compound

A kind of technology of cyclopyridone and compound, applied in the field of preparation of cyclopyridone compound, can solve the problems of complicated post-processing operation, large loss, long operation steps and the like

Active Publication Date: 2020-07-07
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] 1. The operation steps are long;
[0009] 2. The post-processing operation is cumbersome
[0010] 3. The synthesis of compound 9 requires chiral resolution, resulting in a large loss

Method used

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  • A kind of preparation method of cyclopyridone compound
  • A kind of preparation method of cyclopyridone compound
  • A kind of preparation method of cyclopyridone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] The preparation of embodiment 1 formula II compound (LG is a methoxyl group)

[0081] Add compound formula I (10.0g) and dichloromethane (100mL) into the reaction bottle, stir at 0°C, then add methyl trifluoromethanesulfonate (19.48g) dropwise, after the addition is complete, rise to room temperature and stir, react After completion, the reaction was quenched with aqueous sodium carbonate solution, extracted with dichloromethane, and the solvent was evaporated to dryness under reduced pressure to obtain 7.51 g of the compound of formula II with a yield of 66%.

Embodiment 2

[0082] The preparation of embodiment 2 formula IV compound (R 1 is benzyl, R 2 for methyl)

[0083] Add formula II (12g), formula III compound (10.8g), propylphosphoric anhydride (50% ethyl acetate solution) (70g) into the reaction flask, stir and react at 60°C; after the reaction is complete, add 500mL of water and stir, filter, 10.5 g of the compound of formula IV was obtained with a yield of 85% and a purity of 98%.

[0084] LC-MS: [M+1]=326.31;

[0085] 1 H NMR (400MHz, DMSO) δ8.06(d, J=7.8Hz, 1H), 7.59(d, J=7.2Hz, 2H), 7.35(dt, J=24.8, 7.1Hz, 3H), 6.56(d , J=7.8Hz, 1H), 5.12(s, 2H), 4.52(s, 2H), 4.03(t, J=5.4Hz, 2H), 3.72(t, J=5.4Hz, 2H).

Embodiment 3

[0086] The preparation of embodiment 3 formula II compound (LG is chlorine)

[0087]Add the compound formula I (3.0 g) into the reaction flask, add 20 ml of phosphorus oxychloride, raise the temperature to 80° C. for reaction after the addition, and evaporate the phosphorus oxychloride under reduced pressure to obtain the compound of formula II. Yield 80%.

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Abstract

The invention provides a preparation method of a fused-ring pyridone compound, and belongs to the field of pharmaceutical chemicals. The method comprises the following steps: performing a reaction ona morpholine ring compound with an activating reagent to obtain a morpholine ring compound with a leaving group; then adding a pyridone compound and performing a reaction under certain conditions to obtain a triazine compound; and adding a reducing agent, and performing a reaction under different conditions to respectively obtain a racemic fused-ring pyridone compound or a chiral fused-ring pyridone compound. The method has the characteristics of high product purity, high yield, low cost, simplicity in operation and the like.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a preparation method of a cyclopyridone compound. Background technique [0002] Xofluza (Baloxavir Marvoxil, formerly known as S-033188) is an innovative Cap-dependent endonuclease inhibitor, and one of the few new drugs in the world that can inhibit the proliferation of influenza virus. It was developed by Shionogi Pharmaceutical Co., Ltd. in Japan and obtained Accelerated approval, marketed in Japan. Xofluza can target the key link of influenza virus replication and inhibit it from obtaining the CAP structure at the 5' end of host mRNA from host cells, thereby inhibiting the transcription of influenza virus's own mRNA. Since there is no protease with a similar mechanism in the host cell, this drug will theoretically have no effect on the host cell. In 2015, Baloxavir marvoxil was recognized by Japan as a pioneer (Sakigake) drug for preventing influenza A and B. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/14
CPCC07D498/14Y02P20/55
Inventor 周自洪孙国栋曾丽华韩小东王仲清袁希许勇波曾洁滨罗忠华黄芳芳
Owner SUNSHINE LAKE PHARM CO LTD
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