Trifluridine impurity compound and preparation method thereof

A technology of trifluridine and compound, applied in the field of pharmaceutical synthesis, can solve the problems such as impurity compound I and its synthesis method which are not reported in literature, and achieve the effects of short route, high product purity and high reaction yield

Pending Publication Date: 2022-04-22
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] But there is no bibliographical report for this impurity compound I and its synthetic method

Method used

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  • Trifluridine impurity compound and preparation method thereof
  • Trifluridine impurity compound and preparation method thereof
  • Trifluridine impurity compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] At room temperature, compound SM-1 (17.81g, 0.05mol), trifluridine (41.47g, 0.14mol), and Novozyme435 (44.53g) were added to acetone (200ml), and the temperature was controlled at 25-30°C to react. After completion, add LiOH (3.60g, 0.15mol) purified water (20ml) solution at temperature control of 10-15°C. Concentrate under reduced pressure to dryness after deactivation, and finally obtain the target product I after beating with acetone (100ml), the yield is 75.6%, and the purity is 99.42%.

Embodiment 2

[0055] At room temperature, compound SM-1 (17.81g, 0.05mol), trifluridine (20.73g, 0.07mol), Novozyme435 (44.53g) was added to ethanol (200ml), and the temperature was controlled at 25-30°C to react. After completion, add KOH (8.42g, 0.15mol) purified water (30ml) solution at temperature control 15-20°C. After adding, continue to react at temperature control 15-20°C. Concentrate under reduced pressure to dryness after sexing, and finally obtain the target product I after beating with acetone (100ml), the yield is 72.3%, and the purity is 99.10%.

Embodiment 3

[0057] At room temperature, compound SM-1 (17.81g, 0.05mol), trifluridine (59.24g, 0.20mol), and Novozyme435 (44.53g) were added to acetone (200ml), and the temperature was controlled at 25-30°C to react. After completion, add KOH (8.42g, 0.15mol) purified water (30ml) solution at 15-20°C temperature control, continue to control temperature at 0-5°C for reaction, and adjust the pH of the reaction solution to neutral after the reaction is completed. Concentrate under reduced pressure to dryness after deactivation, and finally obtain the target product I after beating with acetone (100ml), the yield is 71.5%, and the purity is 99.16%.

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Abstract

The invention belongs to the technical field of medicine synthesis, and particularly relates to a trifluridine impurity compound and a preparation method thereof. The preparation method comprises the following steps: esterifying 1-((2S, 4S, 5R)-4-acetoxy-5-(acetoxymethyl) tetrahydrofuran-2-yl)-2, 4-dioxo-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylic acid serving as a raw material and hydroxyl at the 5-position of a glycosyl group of trifluridine under the action of Novozyme 435, and then removing a hydroxyl protecting group on the glycosyl group to prepare the trifluridine impurity compound. The synthesis method provided by the invention is simple, and the trifluridine impurity compound obtained by the method is high in purity and high in yield after recrystallization precipitation, and can be used as an impurity reference substance in a trifluridine finished product detection standard.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a trifluridine impurity compound and a preparation method thereof. Background technique [0002] Colorectal cancer (CRC), including colon cancer and rectal cancer, is one of the most common malignant tumors, and its morbidity and mortality rank third among digestive tract malignancies after gastric cancer and esophageal cancer. China is a low-incidence area in the world, but the incidence of colorectal cancer in my country has shown an obvious upward trend in recent years, and it has become one of the fastest-rising malignant tumors in my country. [0003] Due to the lack of obvious early symptoms of colorectal cancer and the lack of early screening measures, most patients have developed to the middle and late stages when they see a doctor. For the treatment of advanced colorectal cancer, the first choice is medical treatment based on chemotherapy. Among ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/073C07H1/00
CPCC07H19/073C07H1/00
Inventor 张贵民崔涛未健波
Owner LUNAN PHARMA GROUP CORPORATION
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