186204-37-5

Basic information

• Product Name: (3aR,7aR)-4'-(1,2-Benzisothiazol-3-yl)octahydrospiro[2H-isoindole-2,1'-piperaziniuM] Methanesulfonate
• Synonyms: (3aR,7aR)-4'-(1,2-Benzisothiazol-3-yl)octahydrospiro[2H-isoindole-2,1'-piperaziniuM] Methanesulfonate;4-(Benzo[d]isothiazol-3-yl)-1-((3aR,7aR)-hexahydro-1H-isoindol-2(3H)-yl)piperazin-1-iuM-1-sulfonate;(3aR,7aR), octahydro-[2H-isoindole-2-spiro-1'-piperazinium], 4'-(1,2-benzisothiazol-3-yl), methanesulfonate (1:1);4-(1,2-Benzothiazol-3-yl)-1-[(3aR,7aR)-octahydro-2H-isoindol-2-yl]piperazin-1-ium-1-sulfonate;Spiro[2H-isoindole-2,1'-piperazinium], 4'-(1,2-benzisothiazol-3-yl)octahydro-, (3aR,7aR)-, methanesulfonate (1:1);(3aR,7aR)-4'-(Benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1'-piperazin]-1'-ium methanesulfonate;(3aR,7aR)-4'-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole- 2,1'-piperazin]-2-ium methanesulfonate
• CAS NO: 186204-37-5
• Molecular Formula: C19H26N4O3S2
• Molecular Weight: 422.56474
• Mol File: 186204-37-5.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3aR,7aR)-4'-(1,2-Benzisothiazol-3-yl)octahydrospiro[2H-isoindole-2,1'-piperaziniuM] Methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,7aR)-4'-(1,2-Benzisothiazol-3-yl)octahydrospiro[2H-isoindole-2,1'-piperaziniuM] Methanesulfonate(186204-37-5)
• EPA Substance Registry System: (3aR,7aR)-4'-(1,2-Benzisothiazol-3-yl)octahydrospiro[2H-isoindole-2,1'-piperaziniuM] Methanesulfonate(186204-37-5)

Safety Data

• Hazardous Substances Data: 186204-37-5(Hazardous Substances Data)

Usage

Uses

(3aR,7aR)-4''-(1,2-Benzisothiazol-3-yl)octahydro-spiro[2H-isoindole-2,1''-piperazinium] Methanesulfonate (B197865) is a useful synthetic intermediate for Lurasidone Hydrochloride (L474920), an antipsychotic used for treatment of schizophrenia.

InChI:InChI=1S/C19H26N4O3S2/c24-28(25,26)23(22-13-15-5-1-2-6-16(15)14-22)11-9-21(10-12-23)19-17-7-3-4-8-18(17)27-20-19/h3-4,7-8,15-16H,1-2,5-6,9-14H2/t15-,16-/m0/s1

Upstream product

• 133070-64-1 3-(piperazin-1-yl)-1,2-benzisothiazole hydrochloride 
• 186204-35-3 (1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate 
• 87691-87-0 3-(1-piperazinyl)-1,2-benzisothiazole 
• 87691-88-1 3-(1-piperazinyl)-1,2-benzisothiazole hydrochloride 

Downstream Products

• 1260022-13-6 N-{[(1R,2R)-2-{[4-(1,2-benzisothiazol-3-yl)-piperazin-1-yl]methyl}cyclohexyl]methyl}biphenyl-3-sulfonamide 
• 139563-25-0 lurasidone hydrochloride 
• 367514-88-3 (3aR,4S,7R,7aS)-2-[((1R,2R)-2-{[4-(l1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl)methyl]hexahydro-1H-4,7-methanisoindol-1,3-dione hydrochloride 
• 194861-74-0 [14C]-Lurasidone 
• 194861-74-0 lurasidone 

Relevant articles and documents

Preparation method of lurasidone

The invention relates to a preparation method of lurasidone. The preparation method comprises the following steps of: reacting a compound as shown in a formula (I) with a compound as shown in a formula (II) under the action of an organic solvent A and a catalyst A, and performing quenching with a weak base solution to obtain a lurasidone crude product. According to the preparation method, the organic solvent A is selected from N-methyl pyrrolidone, N, N-dimethylformamide or a mixture of N-methyl pyrrolidone and N, N-dimethylformamide, preferably N-methyl pyrrolidone; the catalyst A is cesium carbonate; the weak base solution is selected from a cesium carbonate solution, a potassium carbonate solution or a sodium carbonate solution, preferably the potassium carbonate solution. The method is simple to operate, high in product yield, short in reaction time, low in cost and suitable for actual industrial production.

DEUTERATED LURASIDONE

This invention relates to deuterated forms of hexahydro-4,7-methano-1H-isoindole-1,3(2H)-diones, and pharmaceutically acceptable salts thereof. In one aspect, the invention provides a compound of Formula (I): or a pharmaceutically acceptable salt thereof. This invention also provides compositions comprising a compound of this invention, including pharmaceutical compositions comprising the compound and a pharmaceutically acceptable carrier. This invention also provides the use of such compounds and compositions in methods of treating diseases and conditions that are beneficially treated by administering a compounds that modulates the activity of a receptor selected from the group consisting of central dopamine Type 2 (D2) receptor and serotonin Type 2 (5HT2A) receptor. Some exemplary embodiments include a method of treating a disease or condition selected from schizophrenia and depressive episodes associated with bipolar I disorder, the method comprising the step of administering to a subject in need thereof a pharmaceutically acceptable composition of the present invention.

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.