Lurasidone hydrochloride CAS 367514-88-3
Lurasidone hydrochloride 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;(3aR,4S,7R,7aS)-2-(((1R,2R)-2-((4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)methyl)cyclohexyl)methyl)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione hydrochloride;Lurasidone Hydrochloride Tablets;Exodiene Lurasidone;Lurasidone HCl / Lurasidone Hydrochloride;(3aR,4R,7S,7aS)-2-(((1R,2R)-2-((4-(benzo[d]isothiazol-3-yl) |
| CAS: | 367514-88-3 |
| MF: | C28H37ClN4O2S |
| MW: | 529.14 |
| EINECS: | 682-423-6 |
| Product Categories: | Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;367514-88-3;API |
| Mol File: | 367514-88-3.mol |
Lurasidone hydrochloride Chemical Properties
| Melting point | 198-205°C |
| Fp | 9℃ |
| storage temp. | Refrigerator |
| solubility | DMSO : 10 mg/mL (18.90 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble) |
| form | Powder |
| color | White to off-white |
| InChI | InChI=1/C28H36N4O2S.ClH/c33-27-24-18-9-10-19(15-18)25(24)28(34)32(27)17-21-6-2-1-5-20(21)16-30-11-13-31(14-12-30)26-22-7-3-4-8-23(22)35-29-26;/h3-4,7-8,18-21,24-25H,1-2,5-6,9-17H2;1H/t18-,19+,20-,21-,24+,25-;/s3 |
| InChIKey | PQXKDMSYBGKCJA-CVTJIBDQSA-N |
| SMILES | O=C1N(C(=O)[C@@]2([H])[C@]3([H])CC[C@@]([H])(C3)[C@@]12[H])C[C@@H]1CCCC[C@H]1CN1CCN(C2=NSC3=CC=CC=C23)CC1.Cl |&1:5,7,11,14,17,22,r| |
Safety Information
| Hazard Codes | F,T |
| Risk 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 |
| Storage Class | 11 - Combustible Solids |
| Chemical Properties | Off-White Solid |
| Uses | 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 |
| Uses | 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. |
| Biological Activity | Lurasidone is an atypical antipsychotic, used clinically for treatment of schizophrenia and bi-polar disorder. It has nanomolar activity as an antagonist at dopamine D2, serotonin 5-HT2A, 5-HT7, and α2C-adrenergic receptors and as an agonist at 5-HT1A receptors. |
| Synthesis | 186204-37-5 14805-29-9 367514-88-3 (3aR,7aR)-4'-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindol-2,1'-piperazin]-2-ium methanesulfonate (Intermediate 4, 28.8 kg, 66.2 mol) and (3aR,4S,7R,7aS)-rel-hexahydro-1H-4,7-bridged methylidene isoindole-1,3(2H)-dione (Intermediate 5. 12.0 kg, 72.8 mol) as raw material and potassium carbonate (11.0 kg, 79.7 mol) as base were suspended in toluene (270 L). The resulting suspension was heated and refluxed at 105 °C for 15 h. The reaction process was monitored by UPLC. Upon completion of the reaction, the reaction mixture was cooled to room temperature and quenched by the addition of water (90 L). The organic and aqueous phases were separated and the organic phase was concentrated to a smaller volume. Subsequently, the concentrated organic phase was treated with hydrochloric acid in isopropanol to afford the target product (3aR,4S,7R,7aS)-2-(((1R,2R)-2-((4-(benzo[d]isothiazol-3- yl)piperazin-1- yl)methyl)cyclohexyl)methyl)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione hydrochloride ( Lurasidone hydrochloride, 34.4 kg, yield 98.3%, HPLC purity 99.49%). |
| References | [1] Patent: WO2015/56205, 2015, A1. Location in patent: Page/Page column 14 [2] Patent: WO2013/121440, 2013, A1 |
Lurasidone hydrochloride Preparation Products And Raw materials
| Raw materials | (3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione-->Isopropyl alcohol-->Toluene-->Potassium carbonate-->(3aR,7aR)-4'-(1,2-Benzisothiazol-3-yl)octahydrospiro[2H-isoindole-2,1'-piperaziniuM] Methanesulfonate-->Hydrochloric acid |
