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5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride Produkt Beschreibung

5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride Struktur
138982-67-9
CAS-Nr.
138982-67-9
Englisch Name:
5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride
Synonyma:
CP-88059-1;Ziprasidong Hcl;ZIPRASIDONE HCL;Ziprasidone HCl hydrate;ZIPRASIDONE INTERMEDIATE;ZIPRASIDONE HYDROCHLORIDE;ZIPRASIDONE HCL MONOHYDRATE;ZIPRASITONE HCl MONOHYDRATE;Geodon Hydrochloride Hydrate;Ziprasidone Hydrochloride (200 mg)
CBNumber:
CB0166832
Summenformel:
C21H24Cl2N4O2S
Molgewicht:
467.41186
MOL-Datei:
138982-67-9.mol

5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride Eigenschaften

Schmelzpunkt:
300°C
storage temp. 
2-8°C
Löslichkeit
DMSO: >10mg/mL
Aggregatzustand
solid
Merck 
14,10171
CAS Datenbank
138982-67-9(CAS DataBase Reference)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
S-Sätze: 24/25
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  3
RTECS-Nr. NM3241200
HS Code  38220010
Bildanzeige (GHS)
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H317 Kann allergische Hautreaktionen verursachen. Sensibilisierung der Haut Kategorie 1A Warnung P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H373 Kann die Organe schädigen bei längerer oder wiederholter Exposition. Spezifische Zielorgan-Toxizität (wiederholte Exposition) Kategorie 2 Warnung P260, P314, P501
Sicherheit
P260 Dampf/Aerosol/Nebel nicht einatmen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P333+P313 Bei Hautreizung oder -ausschlag: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften

Pale Tan Powder

Originator

Geodon,Pfizer,USA

Verwenden

Ziprasidone Hydrochloride is the hydrochloride salt of a benzisothiazolylpiperazine analog structurally related to the atypical antipsychotic drug tiospirone that antagonizes both central serotonin 5-HT2A (Ki = 0.42 nM) and dopamine D2 (Ki = 4.8 nM) receptors. It is also a potent agonist at 5-HT1A receptors (Ki = 3.4 nM), increasing cortical dopamine release which may offset negative effects associated with dopamine D2 antagonism, and an inverse agonist at 5-HT1B and 5-HT1D receptors (pKis = 8.8 and 8.6, respectively).[Cayman Chemical]

Verwenden

Combined serotonin (5HT2) and dopamine (D2) receptor antagonist. Used as an antipsychotic.

Verwenden

antipsychotic;Dopamine D2/serotonin 5-HT2 antagonist

Definition

ChEBI: The hydrochloride hydrate salt of ziprasidone.

Manufacturing Process

Preparation of 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro- 1,3-dihydro-2H-indol-2-one
A 20-gallon glass lined tank, under a nitrogen atmosphere, was charged with 33.5 liters of water and 9.4 kilograms (kg) of sodium carbonate (dense, 89.1 moles, 3.4 eq.). The resulting mixture was stirred to give a solution. To the solution 6.4 kg of 2-chloroethyl-6-chloro-oxindole (27.8 moles, 1.06 eq.) was charged, followed by 6.7 kg of 3-piperazinyl-1,2-benzisothiazole hydrochloride (26.2 moles, 1.0 eq.). This was stirred and heated to reflux (100°C). After 11 hours the reaction was sampled for high pressure liquid chromatography (HPLC) assay. The reflux was continued for another 2 hours then the reaction was cooled to 25°C and the slurry stirred for 1 hour. The product was observed and found to be essentially free from lumps and gummy matter. The product was collected by filtration. A 14 liter water was added to the tank and cooled to 12°C and then used to wash the product. The cake was pulled as dry as possible, and the product was returned to the tank along with 40 liters of isopropyl alcohol (IPO). This was cooled and then stirred for 2 hours and the product was collected by filtration. The cake was washed with 13.4 liters of fresh IPO, then dried under vacuum at 30° to 40°C. After drying, 17.3 kg of the title compound was obtained. This was in excess of the theoretical weight yield due to some residual carbonate in the crude product.
Recrystallization of 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6- chloro-1,3-dihydro-2H-indol-2-one
To a clean and dry 100-gallon glass lined tank was charged 9.0 kg of the material obtained above and 86 gallons of tetrahydrofuran (THF). The slurry was heated to reflux and held for 1 hour. The hazy solution was then filtered through a 14" sparkler precoated with filter aid and backed with a Fulflo filter to a clean, dry, and "spec free" glass-lined tank on a lower level. The batch was concentrated by vacuum distillation. Another 8.3 kg of the material obtained in above was dissolved in 83 gallons of THF in the upper tank. This was filtered to the lower tank. The tank lines and sparkler were rinsed with 10 gallons of THF. The batch was concentrated to about 22 gallons, then cooled to 5°C and stirred for 1 hour. The product was collected by filtration. Then 20 gallons of fresh IPO were cooled in the tank and used to rinse the product cake. The product was collected and dried under vacuum at 45°C; yielding 9.05 kg of product (83.8% yield for the coupling and recrystallization. The product matched the spectra of a standard NMR and showed the correct retention time by HPLC with 99.7% assay. Another way for preparation of 5-(2-(4-(1,2-benzisothiazol-3-yl)-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2-H- indol-2-one.
A clean and dry 20-gallon glass lined tank was charged with 19 L of water and 4.44 kg of sodium carbonate, after the carbonate had dissolved 4.29 kg (17.5 moles) of 5-(2-chloroethyl)-6-chloro-oxindole and 3.62 kg (16.5 moles) of 1- (1,2-benzisothiazol-3-yl)piperazine were added. The aqueous slurry was heated to reflux and the temperature maintained for 14 hours. When the reaction was complete the solution was cooled to 20°C and filtered. The wet product was reslurried in 23 L of isopropyl alcohol at room temperature for 2 hours. The product was collected by filtration on 2 large Buchner funnels, each was washed with 3.4 L of fresh isopropyl alcohol. The product was vacuum dried at 30° to 40°C. until no isopropyl alcohol remained, giving 5.89 kg (86.4% yield) of the desired free base which matched a standard sample by high performance liquid chromatography (HPLC).
A clean and dry 20-gallon reactor was charged with 17.4 gallons of deionized water and 4.44 L of concentrated hydrochloric acid, to give a 0.77 M solution. To the solution was added 4.44 kg of the anhydrous 5-(2-(4-(1,2- benzisothiazol-yl)-1-piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one

Trademarks

Geodon (Pfizer).

Therapeutic Function

H-Indol-2-one, 5-(2-(4-(1,2-benzisothiazol-3-yl)-1- piperazinyl)ethyl)-6-chloro-1,3-dihydro-, monohydrochloride monohydrate

Biologische Aktivität

Atypical antipsychotic that displays combined serotonin and dopamine receptor antagonism. Displays high affinity at 5-HT 2A receptors with a 5-HT 2A /D 2 affinity ratio greater than any other clinically available atypical antipsychotics (pK i values are 9.38, 8.88, 8.69, 8.47, 8.32, 8.14, 7.98, 7.49, 7.33 and 6.28 for 5-HT 2A , 5-HT 2C , 5-HT 1D , 5-HT 1A , D 2 , D 3 , α 1 , D 4 , H 1 and D 1 receptors respectively).

5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 258)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 20898 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8909 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29954 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6369 58
BOC Sciences
1-631-485-4226
1-631-614-7828 inquiry@bocsci.com United States 19752 58
Chongqing Chemdad Co., Ltd
+86-13650506873
sales@chemdad.com CHINA 37282 58
Alchem Pharmtech,Inc.
8485655694
sales@alchempharmtech.com United States 63726 58
CONIER CHEM AND PHARMA LIMITED
86-18523575427
sales@conier.com CHINA 47498 58

138982-67-9()Verwandte Suche:


  • Ziprasidone (hydrochloride hydrate)
  • 5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one hydrochloride hyd
  • Ziprasidone for system suitability 2
  • Ziprasidone for system suitability 1
  • ZIPRASIDONE HCL
  • ZIPRASIDONE HYDROCHLORIDE
  • ZIPRASIDONE HYDROCHLORIDE MONOHYDRATE
  • 5-[2-[4-(1,2-BENZISOTHIAZOL-3YL)-1-PIPERAZINYL]ETHYL]-6-CHLORO-1,3-DIHYDRO-2H-INDOL-2-ONE, HYDROCHLORIDE MONOHYDRATE
  • CP-88059-1
  • 5-[2-[4-(1,2-benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2h-indol-2-one hydrochloride
  • Ziprasidong Hcl
  • 5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one, Hydrochloride Monohydrate, CP-88059-1
  • 2H-Indol-2-one, 5-2-4-(1,2-benzisothiazol-3-yl)-1-piperazinylethyl-6-chloro-1,3-dihydro-, monohydrochloride, monohydrate
  • ZIPRASIDONE INTERMEDIATE
  • ZIPRASIDONE HCL MONOHYDRATE
  • ZIPRASITONE HCl MONOHYDRATE
  • CP-88059, Geodon, 5-[2-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one monohydrate hydrochloride
  • Ziprasidone monohydrate hydrochloride
  • 5-[2-[4-(1,2-Benzisothiazol-3-y1)-1-piperazinyl]ethyl]-6-chlom-1,3-dihydro-2H-indol-2-one
  • 2H-Indol-2-one, 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-, hydrochloride, hydrate (1:1:1)
  • Ziprasidone Hydrochloride Monohydrate Also see: G364400
  • Ziprasidone Hydrochloride (200 mg)
  • Geodon Hydrochloride Hydrate
  • 5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one hydrochloride hydrat
  • Ziprasidone Hydrochloride Mohydrate
  • Ziprasidone hydrochloride monohydrate, 99%, a novel and potent dopamine and serotonin (5-HT) receptor antagonist
  • 5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one hydrochloride hydrate
  • 5-(2-(4-(1,2-Benzisothiazol-3-yl)Piperazin-1-yl)Ethyl)-6-Chloroindolin-2-One Hydrochloride Hydrate
  • Ziprasidone HCl hydrate
  • Ziprasidone hydrochloride monohydrate CRS
  • Ziprasidone Hydrochloride Monohydra
  • Ziprasidone hydrochloride solution
  • 5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride USP/EP/BP
  • Ziprasidone Hydrochloride Monohydrate DISCONTINUED
  • 2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1
  • 3-dihydro-2H-indol-2-one hydrochloride
  • 138982-67-9
  • C21H21ClN4OSH2OHCl
  • C21H21ClN4OSClHH2O
  • C21H21ClN4OSHClC21H22Cl2N4OS
  • C21H24Cl2N4O2S
  • C21H21ClN4OSHClC21H22Cl2N4
  • C21H21ClN4OSHCl
  • C21H21ClN4OS
  • C21H21ClN4OSHClH2O
  • C21H22Cl2N4OS
  • Other APIs
  • APIs
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Heterocycles
  • Pfizer compounds
  • Sulfur & Selenium Compounds
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