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

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

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

• 155167-99-0 5-(2-(4-(7-bromo-1,2-benzisothiazol-3-yl)piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one 
• 87691-87-0 3-(1-piperazinyl)-1,2-benzisothiazole 
• 118289-55-7 6-chloro-5-(2-chloroethyl)-2-oxindole 
• 160384-41-8 methyl 5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl}-4-chloro-2-nitrophenyl acetate 
• 195244-32-7 Dihydroziprasidone 
• 19398-61-9 2,5-dichlorotoluene 
• 7149-76-0 2,5-dichloro-4-nitrotoluene 
• 160384-38-3 2,5-Dichloro-4-(2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl)-nitrobenzene 
• 160384-37-2 2,5-Dichloro-4-(2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethenyl)-nitrobenzene 
• 160384-40-7 5-(2-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]ethyl)-4-chloro-2-nitrophenyl acetic acid 
• 160384-39-4 5-Chloro-4-(2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl)-2-(bis-(methoxycarbonyl)methyl)-nitrobenzene 
• 160384-45-2 methyl (5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl}-4-chloro-2-nitrophenyl)-cyanoacetate 
• 56341-37-8 6-chloro-2-oxindole 
• 118307-04-3 6-chloro-5-(2-chloroacetyl) indolin-2-one 

Downstream Products

• 195244-32-7 Dihydroziprasidone 
• 188797-80-0 Ziprasidone sulfoxide 
• 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 

Relevant articles and documents

Purification method and preparation method for ziprasidone mesilate

The invention discloses a purification method for ziprasidone mesilate. The purification method comprises the following steps: (1) taking a ziprasidone mesilate crude product, heating for dissolving the ziprasidone mesilate crude product into a mixed solvent formed by tetrahydrofuran and water, and adding carbon for decoloration, and separating out solids, wherein the volume ratio of tetrahydrofuran to water is 15 to (1-5); and (2) washing and drying the solids so as to obtain a ziprasidone mesilate pure product. The purification method is simple and safe to operate and relatively high in yield and purity, does not have special requirements on equipment and can meet the requirements on large-scale industrial production, the industrial production efficiency is improved, the materials are greatly saved, and the industrial production cost is lowered. The invention further discloses a preparation method of high-purity ziprasidone mesilate by virtue of the purification method.

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.

PROCESS FOR PURIFICATION OF ZIPRASIDONE

The present invention relates to a process for the preparation of pure ziprasidone. Thus, for example, ziprasidone tosylate was added to water and aqueous ammonia at room temperature, the contents were heated to 65 °C and maintained for 30 minutes, filtered, washed with water to obtain a wet solid, tetrahydrofuran was added to wet solid and maintained at reflux for 30 minutes. The separated solid was filtered and dried at 65 °C to obtain pure ziprasidone.

PROCESS FOR PREPARING ZIPRASIDONE

The present invention relates to improved process for preparing Ziprasidone an its acid addition salts thereof. The invention particularly provides a method f purifying Ziprasidone base thereby providing substantially pure Ziprasidone and i acid addition salts, hydrates, solvates etc.

AN IMPROVED 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 fiuoro, 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.

Polymorphic forms of ziprasidone sulphates

The present invention relates to novel polymorphic forms of Ziprasidone sulfates, as well as to a process for their preparation and pharmaceutical formulations containing it. The present polymorphic forms of Ziprasidone sulfates are characterized by small average particle sizes and high solubility bestowing the compounds an improved bioavailability.

Process for the preparation of ziprasidone

The present invention relates to an improved method for the preparation of ziprasidone comprising the steps of mixing 5-(2-chloroethyl)-6-chloro-1,3-dihydroindole-2(2H)-one with either a free base or salt form of 3-(1-piperazinyl)-1,2-benzoisothiazole in the presence of a base and an organic solvent characterized in that the organic solvent is a polar aprotic solvent or a mixture of polar aprotic solvents and that the reaction requires the addition of 0,1-0,8 Equivalents of an halide salt, preferably 0,3-0,6 Equivalents, more preferably 0,4-0,5 Equivalents.

A process for the preparation of ziprasidone

A process for the preparation of ziprasidone and a novel intermediate useful in its preparation. The process comprises the reduction of a compound (III) to give a compound (V) which is then reduced to compound (II). This is reacted with compound (IV) to give the desired compound.