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Technique for synthesizing atovaquone

A synthesis process, a technology of atovaquone, is applied in the technical field of chemical synthesis of drugs, can solve the problems of slow reaction speed, low purity of pure atovaquone, long reaction time, etc., and achieves low cost, high purity, The effect of saving synthesis cost

Active Publication Date: 2010-06-02
CHONGQING KOOPPER CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In this synthetic route, two-step reactions of condensation and hydrolysis are required, and no catalyst is added during condensation, the reaction speed is slow and the reaction time is long, and, due to the addition of more reaction reagents, the final prepared atovaquone is pure Product purity is not high

Method used

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  • Technique for synthesizing atovaquone
  • Technique for synthesizing atovaquone
  • Technique for synthesizing atovaquone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 2-Ethoxy-1,4-naphthoquinone (II) (4.30g, 0.02mol), 4-(4-chlorophenyl)cyclohexyl-1-carboxylic acid (I) (4.9g, 0.02mol), Silver nitrate (1.05g, 0.0062mol), acetonitrile 40ml joins in the 500ml four-necked flask, is heated to reflux while stirring with the rotating speed of 300rpm, adds dropwise 80ml ammonium persulfate aqueous solution (12.0g, 0.0525mol) in 1 hour, Reflux and stir for 3 hours, then cool to 0°C, maintain for 30 minutes, filter to obtain a yellow powdery solid, dissolve the crystallized product with 30ml of chloroform, filter off the insoluble matter, distill off the chloroform under reduced pressure, and recrystallize with 40ml of acetonitrile to obtain Atovaquone (III) yellow needle crystal (0.6g), melting point 216°C-219°C (melting point of atovaquone in reference literature is 216°C-219°C), yield 7.8%.

Embodiment 2

[0023] 2-Ethoxy-1,4-naphthoquinone (II) (10.20g, 0.05mol), 4-(4-chlorophenyl)cyclohexyl-1-carboxylic acid (I) (11.94g, 0.05mol), Silver nitrate (1.05g, 0.025mol), acetonitrile 150ml joins in the 500ml four-necked flask, is heated to reflux while stirring with the rotating speed of 200rpm, adds dropwise 160ml ammonium persulfate aqueous solution (34.2g, 0.15mol) in 50min, reflux After stirring for 4 hours, cool to 0°C, maintain for 30 minutes, filter to obtain a yellow powdery solid, dissolve the crystallized product with 80ml of chloroform, filter off the insoluble matter, distill off the chloroform under reduced pressure, and recrystallize with 90ml of acetonitrile to obtain Tovaquinone (III) yellow needle-like crystals (1.38g), yield 7.5%.

Embodiment 3

[0025] The synthesis process steps and process conditions are the same as in Example 1, except that the amount of ammonium persulfate aqueous solution added is: 80ml ammonium persulfate aqueous solution (9.1g, 0.04mol), and the final yield is 7.65%.

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PUM

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Abstract

The invention discloses a synthesis technology of Atovaquone. When a silver nitrate catalyst exists, 2-ethoxyl-1, 4-naphthoquinone and 4-(4-chlorophenyl) cyclohexyl-1-methanoic acid which are used asraw material react in acetonitrile solvent, and reaction reagent is added into a reaction vessel, the mixed solution is stirred and heated until refluxing is generated; when the refluxing is dripped down, the water solution of ammonium persulfate is added in, and the quantity of the ammonium persulfate is 2 to 3 times of the mole number of the 2-ethoxyl-1, 4-naphthoquinone; after the reaction is completed, the mixed solution is performed through cooling crystallization and filtration, and is filtered again by using the dissolving crystalization product of chloroform; filter liquor is collected, decompressed and evaporated to obtain the chloroform which is recrystallized to obtain yellow acicular crystal of the Atovaquone by using the acetonitrile. The synthesis route only comprises one-step reaction, the synthesizing cost is saved, the yield rate is high, and the prepared Atovaquone has high purity quotient.

Description

technical field [0001] The invention relates to a process for chemically synthesizing medicines, in particular to a process for synthesizing Atovaquone. Background technique [0002] Atovaquone (I) (2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthalenedione, English name: Atovaquone, CAS number: 95233-18 -4) is a homologue of coenzyme Q, which has anti-several protozoan activity, and its action site is the binding point of cytochrome bcl (binding point III) for Plasmodium. Dihydrolactate dehydrogenase is an important enzyme in pyridine biosynthesis. It connects mitochondria for electron transfer through coenzyme Q, so this product prevents pyridine synthesis by inhibiting electron transfer. Some metabolic enzymes participate in mitochondrial electron transfer through coenzyme Q, therefore, the inhibition of electron transfer by this product actually inhibits the activity of these enzymes. [0003] [0004] Currently, atovaquone is generated by the condensatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C50/32C07C46/00
Inventor 王宇廖家华李倩刘青
Owner CHONGQING KOOPPER CHEM IND
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