Synthetic method of lurasidone

A technology of lurasidone and a synthesis method, which is applied in the field of organic synthesis, can solve the problems of low synthesis efficiency, high cost, high consumption of raw materials, etc., and achieves the effects of reduced production cost, short reaction steps, and simple post-treatment process.

Active Publication Date: 2013-02-20
SHANGHAI BIRCH CHEM TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In view of the above-mentioned shortcomings of the prior art, the object of the present invention is to provide a synthetic method of lurasidone with a simple route and suitable for industrial production, which is used to solve the problem of low synthesis efficiency, high consumption of raw materials and high cost in the prior art. advanced questions

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  • Synthetic method of lurasidone
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Experimental program
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Effect test

Embodiment 1

[0038] On a 1-liter four-neck flask, install a mechanical stirrer, a thermometer, and under nitrogen protection, add 62 grams of (R,R')-1,2-bis(methylsulfonyl-2oxymethyl)cyclohexane at room temperature (0.21mol), 44.6 grams of 3-(1-piperazinyl)-1,2-benzisothiazole (0.2mol), 500 milliliters of DMF, and 53 grams of Na 2 CO 3 (0.5mol). Then heat and stir, and react at 80° C. for 16 hours.

[0039] Then cool down to below 40°C, add 38.3g of bicyclo[2,2,1]heptane-2,3-dicarboximide (0.22mol) in batches to the reaction liquid, then raise the temperature to 80°C, and react 18 Hour. Cool to room temperature, filter, and distill off most of the DMF (about 450ml) from the filtrate at 70°C under reduced pressure. Cool to below 40°C, add 600ml of water to disperse the residual solid, filter at room temperature, and wash 3 times with 100ml of water to obtain a crude product. The crude product was dispersed in acetone for recrystallization, and dried to obtain 62 g of light yellow solid...

Embodiment 2

[0043] On the 3-liter four-neck flask, install a mechanical stirrer, a thermometer, and under nitrogen protection, add 187 grams of (R,R')-1,2-bis(methylsulfonyl-2oxymethyl)cyclohexane at room temperature (0.62mol, 1.02eq), 134 grams of 3-(1-piperazinyl)-1,2-benzisothiazole (0.6mol, 1.0eq), 2000 milliliters of ethylene glycol dimethyl ether, and 207 grams of K 2 CO 3 (1.5mol, 2.5eq). Then heat and stir, and react at 80° C. for 18 hours until the raw material bis(methylsulfonyl-2oxymethyl)cyclohexane disappears.

[0044] Then cool to below 40°C, add 109g of bicyclo[2,2,1]heptane-2,3-dicarboximide (0.66mol, 1.1eq.) in batches to the reaction liquid, and then heat up to 80°C , reacted for 16 hours. Cool and filter to remove inorganic salts and alkalis, distill most of the ethylene glycol dimethyl ether (about 1800ml) out of the filtrate at 60°C under reduced pressure, then cool to 40°C, add 1200ml of water to disperse the residual solid, filter at room temperature, wash with 4...

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Abstract

The invention relates to the field of organic synthesis and particularly relates to a synthetic method of lurasidone (lurasidone, CAS#; 367514-87-2). The synthetic method of lurasidone includes the following steps: adding (R,R')-1,2-di(methylsulfonyl-di-oxyl-methyl) cyclohexane, 3-(1-piperazine-base)-1,2-benzo-isothiazolone and alkali into organic solvent, reacting for 6-20 hours under the temperature of 50-150 DEG C, adding bicycle[2,2,2]heptane-2,3-dicarboximide, reacting for 6-20 hours under the temperature of 50-150 DEG C to obtain reaction liquid containing lurasidone, and purifying the reaction liquid to obtain lurasidone. The process line still has the advantages of being high in yield, short in reaction step, simple in post-processing process, good in solvent recycling effect and the like after being amplified, thereby being capable of synthetizing lurasidone in one step.

Description

technical field [0001] The present invention relates to the field of organic synthesis, in particular to a method for synthesizing lurasidone (CAS#; 367514-87-2). Background technique [0002] Lurasidone hydrochloride (CAS#;367514-88-3) is a new type of drug for the treatment of schizophrenia developed by Sumitomo Pharmaceutical Co., Ltd., which was approved by the US Food and Drug Administration (FDA) on October 28, 2010. . Its mechanism of action may be related to the antagonism of dopamine D2 and 5-hydroxytryptamine 2A (5-HT2A) receptors. [0003] Currently, there is only one synthetic method of lurasidone reported. The corresponding patent US5780632 reports the combination of 3-(1-piperazinyl)-1,2-benzisothiazole and (R,R')-1,2- Two (methylsulfonyl-2 oxymethyl) cyclohexane as raw material, first in Na 2 CO 3 and acetonitrile system for N-alkylation substitution, and then with bicyclo[2,2,1]heptane-2,3-dicarboximide in K 2 CO 3 , 18 crown 6 and xylene system for N-a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12
Inventor 孙光福吴汉成
Owner SHANGHAI BIRCH CHEM TECH CO LTD
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