Synthesis technology for preparing oteracil potassium

A technology of potassium oxonate and potassium carbonate, which is applied in the field of synthesis of the pharmaceutical compound potassium oxonate, can solve problems such as the toxicity of the oxidant bromine and large environmental pollution, and achieve the effects of stable quality, high yield, and easy availability of raw materials

Inactive Publication Date: 2013-12-11
JIANGSU QINGJIANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] This method uses allantoin as a raw material through bromine oxidation. The raw material allantoin has been produced in a large scale in Chin

Method used

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  • Synthesis technology for preparing oteracil potassium
  • Synthesis technology for preparing oteracil potassium
  • Synthesis technology for preparing oteracil potassium

Examples

Experimental program
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Effect test

Embodiment 1

[0021] 1. Synthesis of Crude Potassium Oxonate

[0022] Add 1080 mL of distilled water to a 2L reaction flask, and add 275.0 g (4.00 mol) of potassium hydroxide in batches under stirring to obtain a 16.6% (w / w) potassium hydroxide solution. Cool in an ice bath to 5-10°C, add 79.0g (0.50 mol) of allantoin and 4.0g (0.024mol) of potassium iodide (keep the internal temperature ≤ 10°C), stir to dissolve most of it. Cool in an ice bath to 2-5°C, add 420.0 g of sodium hypochlorite solution (10% available chlorine) dropwise under stirring for about 4-5 hours. After dropping, keep the ice bath for 2h, and slowly rise to room temperature (about 2-3h). Stir at room temperature (20°C) for 8h. The end point of the reaction was detected by HPLC (chromatographic column: octadecylsilane bonded silica gel column as filler; mobile phase: methanol: water: phosphoric acid (5:95:0.1); retention time of allantoin was about 2.4min, oxazine The retention time of potassium acid potassium is about ...

Embodiment 2

[0032] Add 1200mL of distilled water into a 2L reaction flask, and add 275.0g (4.00mol) of potassium hydroxide in batches under stirring. Cool in an ice bath to 5-10°C, add 79.0g (0.50mol) of allantoin and 4.0g (0.024mol) of potassium iodide (keep the internal temperature ≤ 10°C), stir to dissolve most of it. Cool in an ice bath to 2-5°C, add 450.0 g of potassium hypochlorite solution (5% available chlorine) dropwise under stirring for about 4-5 hours. After dropping, keep the ice bath for 2h, and slowly rise to room temperature (about 2-3h). Stir at room temperature (20°C) for 12h. A small amount of insoluble matter in the reaction solution was filtered off to obtain a light yellow solution. The inner temperature of the ice bath is 10-12°C, acidify by adding 10% citric acid dropwise under stirring until the pH of the solution is 7, and a large amount of white precipitates are precipitated. Ice bath at 5°C, stirring for 2h. Filter with suction and wash the filter cake with...

Embodiment 3

[0034] Add 1200mL of distilled water into a 2L reaction flask, and add 275.0g (4.00mol) of potassium hydroxide in batches under stirring. Cool in an ice bath to 5-10°C, add 79.0g (0.50mol) of allantoin and 4.0g (0.024mol) of potassium iodide (keep the internal temperature ≤ 10°C), stir to dissolve most of it. Cool in an ice bath to 2-5°C, add 480.0 g of potassium hypobromite solution (5% available bromine) dropwise under stirring for about 4-5 hours. After dropping, keep the ice bath for 2h, and slowly rise to room temperature (about 2-3h). Stir at room temperature (20°C) for 8h. A small amount of insoluble matter in the reaction solution was filtered off to obtain a light yellow solution. The inner temperature of the ice bath is 10-12°C, acidify by adding 10% citric acid dropwise under stirring until the pH of the solution is 7, and a large amount of white precipitates are precipitated. Ice bath at 5°C, stirring for 2h. Filter with suction and wash the filter cake with di...

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Abstract

The invention provides a synthesis technology for preparing oteracil potassium. With short reaction steps, the technology avoids the adoption of toxic and harmful bromine as an oxidant. The synthesis technology is characterized by comprising the following step of dissolving allantoin in a potassium hydroxide or potassium carbonate aqueous solution, wherein potassium iodide is used as a catalyst, and a pypocholoride aqueous solution is used as an oxidant. The method provided by the invention has the advantages of simplicity in operation, mild reaction conditions, high yield, high product purity and the like, and is suitable for industrial production of oteracil potassium.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for synthesizing the drug compound potassium oxonate. Background technique [0002] Potassium oxonate, also known as oteracil potassium, chemical name: 1,4,5,6-tetrahydro-4,6-dioxo-1,3,5-triazine-2-carboxylate Potassium acid, the chemical structural formula is as follows: [0003] [0004] Potassium oxonate is one of the three components (tegafur, gimeracil, and potassium oxonate) of the antigastric cancer drug cefecone (S-1). Tegafur, as a commonly used anti-gastric cancer drug in clinical practice, has limitations such as incomplete oral absorption, short half-life of 5-20 minutes, rapid metabolism, and adverse reactions such as diarrhea. Tegafur is a prodrug of 5-fluorouracil, which has a good oral absorption effect and is gradually converted into 5-fluorouracil in the liver. Gimostel inhibits the degradation of 5-fluorouracil by inhibiting dihydropyrimidine dehydr...

Claims

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Application Information

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IPC IPC(8): C07D251/20
Inventor 隽海龙
Owner JIANGSU QINGJIANG PHARMA
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