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Preparation method of antipsychotic drug lurasidone

A diketone and compound technology, applied in the field of preparation of the antipsychotic drug lurasidone, can solve the problems of by-products, high solvent toxicity, and difficulty in industrial production, and achieve the effects of mild reaction conditions, simple operation, and easy purification

Inactive Publication Date: 2013-12-18
广东永正药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the solvent used in this method is more toxic and environmentally unfriendly. At the same time, when the synthetic target product is refluxed in toluene with potassium carbonate as a base, it is easy to produce some by-products. The existence of by-products makes the purification of the target product difficult to operate. After refining, it will have a great impact on the yield. In US 2011263848A1 and US2011263847A1, the existing problems have been optimized accordingly, but there are still by-products, and the experimental operation is cumbersome, and it is not easy to carry out industrial production

Method used

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  • Preparation method of antipsychotic drug lurasidone
  • Preparation method of antipsychotic drug lurasidone
  • Preparation method of antipsychotic drug lurasidone

Examples

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Embodiment Construction

[0017] The following examples are intended to illustrate the present invention in detail, but not to limit the present invention.

[0018] 1. (1R,2R)-1,2-cyclohexanedimethanol dimesylate formula (III)

[0019]

[0020] Add 500.0g (1R,2R)-1,2-cyclohexanedimethanol to a 10L three-necked flask, add 1052.5g triethylamine and 835.0g methanesulfonyl chloride to 7500ml dichloromethane in sequence, and react for 8 hours after adding. Add 3750ml of purified water to the reaction system, stir and wash, separate the liquid and discard the water layer, wash the organic phase with dilute hydrochloric acid, then wash with saturated sodium bicarbonate in turn, wash with saturated brine, separate the liquid, and use anhydrous sodium sulfate for the organic phase dry. Anhydrous sodium sulfate was filtered off, and concentrated to dryness under reduced pressure. Diethyl ether was added thereto, filtered with suction, and the filter cake was air-dried at 60°C to obtain 889.4 g of off-white ...

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Abstract

The invention relates to preparation methods of (3aR,4S,7R,7aS)-2-{(1R,2R)-2-[4-(1,2-benzisothiazole-3-yl)piperazinyl-1-methyl]cyclohexyl methyl}hexahydro-1H-4,7-methano-isoindole-1,3-dione (a compound represented by a formula I) and intermediates thereof. A hydrochloride (lurasidone hydrochloride) of the compound represented by the formula (I) can be used as a drug for treatment of psychosis.

Description

technical field [0001] The present invention relates to a kind of (3aR,4S,7R,7aS)-2-{(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)piperazine-1-methyl ]Cyclohexylmethyl}hexahydro-1H-4,7-methylisoindole-1,3-dione (compound of formula I) and its intermediates. Background technique [0002] Lurasidone hydrochloride (Lurasidone hydrochloride, trade name Latuda) is a new type of antipsychotic drug with dual effects developed by Japan's Sumitomo Pharmaceutical Company. affinity. It has obvious curative effect on positive and latent symptoms of mental patients. JP 2006169155 reported the synthesis route of formula (I), using (1R,2R)-1,2-cyclohexanedimethanol dimethanesulfonate compound of formula (III) as starting material, heating and refluxing in toluene to obtain Methanesulfonic acid quaternary ammonium salt formula (V), the obtained quaternary ammonium salt and (3aR,4S,7R,7aS)-4,7-methylene-1H-isoindole-1,3-2H-dione formula (VI) Reaction, reflux in toluene with potassium carbonate ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12C07D487/10C07C309/65C07C303/28
Inventor 陆荣政李宏曾祥萍
Owner 广东永正药业有限公司
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