199191-69-0

Basic information

• Product Name: Ziprasidone mesilate
• Synonyms: 2H-INDOL-2-ONE, 5-[2-[4-(1,2-BENZISOTHIAZOL-3-YL)-1-PIPERAZINYL]ETHYL]-6-CHLORO-1,3-DIHYDRO-, MONOMETHANESULFONATE, TRIHYDRATE;5-[2-[4-(1,2-benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2h-indol-2-one mesilate;ziprasidone mesilate;ZIPRASIDONE MESYLATE;Ziprasidone Hcl / Mesilate 138982-67-9 /;Ziprasidone mesylate trihydrate;2H-Indol-2-one, 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-,monomethanesulfonate, trihydrate
• CAS NO: 199191-69-0
• Molecular Formula: C₂₁H₂₁ClN₄OS
• Molecular Weight: 563.09
• Mol File: 199191-69-0.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 836.3 °C at 760 mmHg
• Flash Point: 459.6 °C
• Appearance: /
• Vapor Pressure: 1.13E-29mmHg at 25°C
• CAS DataBase Reference: Ziprasidone mesilate(CAS DataBase Reference)
• NIST Chemistry Reference: Ziprasidone mesilate(199191-69-0)
• EPA Substance Registry System: Ziprasidone mesilate(199191-69-0)

Safety Data

• Hazardous Substances Data: 199191-69-0(Hazardous Substances Data)

Usage

Description

Ziprasidone mesilate, also known as the methanesulfonate trihydrate salt of ziprasidone, is a pharmaceutical compound with potent antipsychotic properties. It acts as a central antagonist for D2 and 5HT2 receptors, making it a valuable agent in the treatment of various psychiatric disorders.

Uses

Used in Pharmaceutical Industry:
Ziprasidone mesilate is used as an antipsychotic agent for the treatment of psychiatric disorders characterized by positive and negative symptoms, such as schizophrenia and bipolar disorder. Its action as a central D2 and 5HT2 receptor antagonist helps in managing these symptoms effectively.
Additionally, due to its receptor antagonist properties, ziprasidone mesilate may also be utilized in other applications within the pharmaceutical industry, such as the development of medications for other central nervous system disorders.

InChI:InChI=1/C21H21ClN4OS.CH4O3S.3H2O/c22-17-13-18-15(12-20(27)23-18)11-14(17)5-6-25-7-9-26(10-8-25)21-16-3-1-2-4-19(16)28-24-21;1-5(2,3)4;;;/h1-4,11,13H,5-10,12H2,(H,23,27);1H3,(H,2,3,4);3*1H2

Upstream product

• 160384-41-8 methyl 5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl}-4-chloro-2-nitrophenyl acetate 
• 87691-87-0 3-(1-piperazinyl)-1,2-benzisothiazole 
• 118289-55-7 6-chloro-5-(2-chloroethyl)-2-oxindole 
• 155167-99-0 5-(2-(4-(7-bromo-1,2-benzisothiazol-3-yl)piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one 
• 2634-33-5 1,2-benzisothiazol-3-one 
• 147124-32-1 dimethyl (4-chloro-2-nitrophenyl)malonate 
• 89-61-2 2,5-dichloronitrobenzene 
• 884305-06-0 6-chloro-5-(2-chloro-1-hydroxyethyl) indolin-2-one 
• 118307-04-3 6-chloro-5-(2-chloroacetyl) indolin-2-one 
• 87691-88-1 3-(1-piperazinyl)-1,2-benzisothiazole hydrochloride 
• 155167-98-9 7-bromo-3-piperazinyl-1,2-benzisothiazole 
• 155167-97-8 3,7-dibromo-1,2-benzisothiazole 
• 56341-37-8 6-chloro-2-oxindole 
• 160384-45-2 methyl (5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl}-4-chloro-2-nitrophenyl)-cyanoacetate 

Downstream Products

• 1028903-39-0 5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]-ethyl}-6-chloro-1,3-dihydro-2H-indol-2-one hydrobromide monohydrate 
• 188797-80-0 Ziprasidone sulfoxide 
• 195244-32-7 Dihydroziprasidone 

Relevant articles and documents

A key intermediate for the preparation of ziprasidone

The present invention relates to a ziprasidone key intermediate preparation method, wherein benzo[d]isothiazole-3-ol (or one) is adopted as a raw material, and reacts with a substituted sulfonyl chloride or anhydride under an alkaline condition to obtain benzo[d]isothiazole-3-substituted sulfonate, and the benzo[d]isothiazole-3-substituted sulfonate reacts with piperazine to prepare the ziprasidone key intermediate 3-(1-piperazinyl)-1,2-benzoisothiazole. The method of the present invention has characteristics of simple operation, easily available raw materials, less byproducts, simple post-treatment, less industrial three-waste and the like, and is especially suitable for industrial production.

A SHORT PROCESS FOR THE PREPARATION OF ZIPRASIDONE AND INTERMEDIATES THEREOF

A process for the preparation of oxindole derivative (Ziprasidone hydrochloride) of formula (I) comprising reacting compound of formula (II) with metal or metal compound mineral acid to give compound of formula (III) in a single step which is converted into compound of formula IV which is a key intermediate for the preparation of compound of compound of formula (I).

Process for the Preparation of Ziprasidone

The present invention relates to a process for preparing Ziprasidone of formula I, or a pharmaceutically acceptable salt or a solvate or a hydrate thereof; comprising the steps of reacting 1-(1,2-benzisothiazol-3-yl) piperazine of formula II or its salt: with 5-(2-haloethyl)-6-chloro-oxindole of formula III: wherein X is leaving groups like fluoro, chloro, bromo, iodo or sulphonyl; in the presence of a dispersing agent and a base in a solvent to form ziprasidone of formula I; and optionally converting the ziprasidone formed into a pharmaceutically acceptable acid addition salts of ziprasidone; or a solvate or a hydrate thereof.