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Synthesis method of metixene hydrochloride

A technology of Mesaisan hydrochloride and a synthesis method, which is applied in the field of synthesis technology of anti-shock paralysis drugs, can solve the problems of high price of molybdenum trisulfide, does not conform to green chemistry, is unfavorable to industrialization, and achieves low cost, low price and production cost. reduced effect

Inactive Publication Date: 2011-04-27
EAST CHINA NORMAL UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0002]Methasan hydrochloride is an anti-parkinsonian drug, also known as metixene hydrochloride (metixene hydrochloride) is an M receptor blocker used to treat Parkinson's Diseases, including the relief of drug-induced extrapyramidal syndrome. U.S. Patent US2905590, reported that its synthesis method is to condense thioxanthene and 3-chloromethyl-1-methylpiperidine under the action of alkali, and then pass through hydrochloric acid Acidification obtains Methasan hydrochloride, but this method uses toxic benzene and flammable sodium, which is not conducive to industrialization
The synthesis of 2-phenylthiobenzoic acid has been reported in many documents, but all use organic solvents, causing environmental pollution and not meeting the requirements of green chemistry
And 9-thioxanthone (3) was obtained in the process of thioxanthene (4) through carbonyl reduction, Takido, Toshio (Journal of Heterocyclic Chemistry (1995), 32 (2), 687-90.) reported the use of molybdenum trisulfide As a catalyst, it can be reduced in a hydrogen environment, but molybdenum trisulfide is expensive, and the reaction must be carried out in a hydrogen environment, which raises the requirements for the reaction equipment, which is not conducive to industrialization.

Method used

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  • Synthesis method of metixene hydrochloride
  • Synthesis method of metixene hydrochloride
  • Synthesis method of metixene hydrochloride

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Effect test

Embodiment 1

[0030] Synthesis of 2-phenylthiobenzoic acid (2)

[0031] KOH (54.5g, 972.7mmol) and 600ml H 2 O was made into a solution and cooled to room temperature. N 2 Under protection, the raw material thiosalicylic acid (30g, 389.1mmol) was added into a 1000ml three-neck flask, dissolved in the KOH solution prepared above and heated to 60°C and stirred for 30 minutes, N 2 Add cuprous bromide (1.675g, 11.6mmol) under protection, add iodobenzene, heat up to reflux, react for 20h, stop heating, cool the reaction solution to room temperature, add 100ml of concentrated hydrochloric acid dropwise, the time is 30min, and the pH value is 1 , a large number of yellow solids were generated, and the yellow solid was obtained by suction filtration, and the precipitate was washed with 2 × 500ml of water to obtain a white solid, which was dried to obtain the target product 2-phenylthiobenzoic acid (2) 85.5g, yield 95.5%

[0032] 1 HNMR (500MHz, CDCl 3 )8.2~8.4(d, 1H), 7.7~7.8(t, 2H), 7.5~7.6(t...

Embodiment 2

[0043] Synthesis of 2-phenylthiobenzoic acid (2)

[0044] KOH (54.5g, 972.7mmol) and 600ml H 2 O was made into a solution and cooled to room temperature. N 2 Under protection, the raw material thiosalicylic acid (1) (30g, 389.1mmol) was added into a 1000ml three-necked bottle, dissolved in the KOH solution prepared above and heated to 60°C and stirred for 30 minutes, N 2 Add cuprous iodide (2.2g, 11.6mmol) under protection, add iodobenzene, heat up to reflux, react for 20h, stop heating, cool the reaction solution to room temperature, add 100ml of concentrated hydrochloric acid dropwise, the time is 30min, and the pH value is 1 , a large number of yellow solids were generated, and the yellow solid was obtained by suction filtration, and the precipitate was washed with 2 × 500ml of water to obtain a white solid, which was dried to obtain the target product 2-phenylthiobenzoic acid (2) 85.5g, yield 95.5%

[0045] Synthesis of 9-thioxanthone (3)

[0046] N 2 Under protection...

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Abstract

A synthesis method of metixene hydrochloride relates to a synthesis process of an antiparkinsonian drug. The synthesis method comprises the following steps: taking thiosalicylic acid as a raw material to obtain 2-thiophenyl benzoic acid by coupling with iodobenzene; then dehydrating and cyclizing to obtain 9-thioxanthone; reducing a carbonyl to obtain thioxanthene; and finally allowing the thioxanthene to react with 3-chloromethyl-1-pipecoline to obtain the target product (5) metixene hydrochloride shown as a formula (5) below. The synthesis method has the advantages of available raw materials, low cost, short preparation course, simple operation and easy industrialization, and helps produce the metixene hydrochloride which is the antiparkinsonian drug.

Description

technical field [0001] A method for synthesizing mesai powder hydrochloride, relating to a synthesis process of an anti-parkinsonian drug, belonging to the technical field of pharmaceutical preparation Background technique [0002] Methasan hydrochloride is an anti-parkinsonian drug, also known as metixene hydrochloride (metixene hydrochloride) is a M receptor blocker, used for the treatment of Parkinson's disease, including the relief of drug-induced extrapyramidal syndrome. US Patent US2905590 reports that its synthetic method is to condense thioxanthene and 3-chloromethyl-1-methylpiperidine under the effect of alkali, and then obtain Methasan hydrochloride through hydrochloric acid acidification, but this method uses the large toxic Benzene and easily flammable sodium are not conducive to industrialization. The synthesis of 2-phenylthiobenzoic acid has been reported in many literatures, but all of them use organic solvents, which cause environmental pollution and do not ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/06A61P25/16
Inventor 胡文浩徐勤耀石炜杨琍苹
Owner EAST CHINA NORMAL UNIV
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