367514-88-3

Basic information

• Product Name: Lurasidone hydrochloride
• Synonyms: Lurasidonhydrochloride;Lurasidonhydrochlorid;(3aR,4S,7R,7aS)-2-[[(1R,2R)-2-[[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]methyl]cyclohexyl]methyl]hexahydro-4,7-methano-1H-isoindole-1,3(2H)-dione hydrochloride;(1R,2S,3R,4S)-N-[(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinylMethyl]-1-cyclohexylMethyl]-2,3-bicyclo[2.2.1]heptanedicarboxyiMide hydrochloride;Latuda, SM 13496;Lurasidone Hydrochlorid;(3aR,4S,7R,7aS)-2-[(1R,2R)-2-[4-(1,2-Benzisothiazol-3-yl)piperazin-1-ylMethyl]cyclohexylMethyl]hexahydro-1H-4,7-Methanoisoindole-1,3-dione hydrochloride;4,7-Methano-1H-isoindole-1,3(2H)-dione, 2-[[(1R,2R)-2-[[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]methyl]cyclohexyl]methyl]hexahydro-, hydrochloride (1:1), (3aR,4S,7R,7aS)-
• CAS NO: 367514-88-3
• Molecular Formula: C₂₈H₃₆N₄O₂S*ClH
• Molecular Weight: 492.684
• EINECS: 200-659-6
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 367514-88-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 198-205°C
• Flash Point: 9℃
• Appearance: /
• Storage Temp.: Refrigerator
• CAS DataBase Reference: Lurasidone hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Lurasidone hydrochloride(367514-88-3)
• EPA Substance Registry System: Lurasidone hydrochloride(367514-88-3)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 1
• Hazardous Substances Data: 367514-88-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 367514-88-3 differently. You can refer to the following data:
1. Lurasidone is an atypical antipsychotic, inhibits Dopamine D2, 5-HT2A, 5-HT7, 5-HT1A and noradrenaline α2C with IC50 of 1.68 nM, 2.03 nM, 0.495 nM, 6.75 nM and 10.8 nM, respectively
2. An antipsychotic used for treatment of schizophrenia.

Definition

ChEBI: A hydrochloride obtained by reaction of lurasidone with one equivalent of hydrochloric acid. An atypical antipsychotic agent used for the treatment of schizophrenia.

Upstream product

• 87691-87-0 3-(1-piperazinyl)-1,2-benzisothiazole 
• 7647-01-0 hydrogenchloride 
• 194861-74-0 lurasidone 
• 133070-64-1 3-(piperazin-1-yl)-1,2-benzisothiazole hydrochloride 
• 129-64-6 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 
• 186204-37-5 (3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate 
• 14805-29-9 (3aR,4S,7R,7aS)?4,7?methylene?1H?isoindole?1,3(2H)-dione 
• 2746-19-2 (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 542-92-7 cyclopenta-1,3-diene 
• 3205-34-3 (1S,2S)-(–)-1,2-di(hydroxymethyl)cyclohexane 
• 173658-50-9 (1S,2S)-cyclohexane-1,2-dimethanol bis(methanesulfonate) 
• 14166-28-0 exo-bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride 
• 1384511-83-4 3-[bis(hydroxyethyl)]amino-1,2-benzisothiazole 
• 23031-78-9 3-aminobenzisothiazole 

Downstream Products

• 139563-25-0 (3aR,4S,7R,7aS)-2-{(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)piperazin-1-ylmethyl]cyclohexylmethyl}hexahydro-1H-4,7-methanisoindol-1,3-dione dihydrochloride 

Relevant articles and documents

Method for preparing lurasidone and salt thereof

The invention relates to a method for preparing lurasidone and a salt thereof. The method comprises the following steps: reacting (R,R)-1,2-bis(methanesulfonyloxymethyl)cyclohexane and 3-(1-piperazinyl)-1,2-benzoisothiazole hydrochloride in acetonitrile in the presence of potassium carbonate to obtain an intermediate I; reacting the intermediate I with (3aR,4S,7R,7aS)-4,7-methylene-1H-isoindole-1,3(2H)-dione in DMF in the presence of potassium carbonate to prepare lurasidone free alkali; and reacting the lurasidone free alkali with hydrochloric acid in isopropanol to obtain lurasidone hydrochloride. The invention also relates to lurasidone and the salt thereof prepared by using the method, and application of lurasidone and the salt thereof in medicines for resisting psychosis, especially schizophrenia. The method disclosed by the invention has one or more advantages in a group consisting of simple process, high product yield, few impurities and the like.

Lurasidone key intermediate preparation method

The present invention relates to a lurasidone key intermediate preparation method, and belongs to the technical field of compound synthesis. According to the method, when 4,-(1,2-benzisothiazol-3-yl)-(3aR,7aR)-octahydrospiro(2H-isoindole-2,1-piperazine)methanesulfonate is generated, 4-(1,2-benzisothiazol-3-yl)-1-piperazine is adopted as a raw material, the 4-(1,2-benzisothiazol-3-yl)-1-piperazine, (1R,2R)-1,2-bis(methanesulfonyloxymethyl)cyclohexane and potassium carbonate are subjected to a reaction in a solvent toluene, and a cyclodextrin phase transfer catalyst is added to the reaction system. According to the present invention, by using the cyclodextrin as the phase transfer catalyst, the incomplete reaction problem is solved, and the yield is substantially improved.

Method for preparing lurasidone with high purity and high yield

The invention provides a method for preparing lurasidone with high purity and high yield. On the basis of an existing lurasidone preparation method, a small quantity of specific protic solvent is added in the preparation process of (R,R)-3a,7a-9H-isoindole-2-1'-[4'-(1,2-benzisothiazole-3-yl)] piperazine mesylate, so that the reaction rate is greatly increased, the time is shortened to 3 h from 23 h in the prior art, the yield is increased from 82% to 90%, the total yield is up to 71%, and the prepared finished product has the consistent quality with original drugs.