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

5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride 구조식 이미지
카스 번호:
138982-67-9
상품명:
5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride
동의어(영문):
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
분자식:
C21H24Cl2N4O2S
포뮬러 무게:
467.41186
MOL 파일:
138982-67-9.mol

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

녹는점
300°C
저장 조건
2-8°C
용해도
DMSO: >10mg/mL
물리적 상태
solid
Merck
14,10171
CAS 데이터베이스
138982-67-9(CAS DataBase Reference)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
안전지침서 24/25
유엔번호(UN No.) UN1230 - class 3 - PG 2 - Methanol, solution
WGK 독일 3
RTECS 번호 NM3241200
HS 번호 38220010
그림문자(GHS):
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H317 알레르기성 피부 반응을 일으킬 수 있음 피부 과민성 물질 구분 1 경고 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H373 장기간 또는 반복 노출되면 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킬 수 있음 특정 표적장기 독성 - 반복 노출 구분 2 경고 P260, P314, P501
예방조치문구:
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P333+P313 피부자극성 또는 홍반이 나타나면 의학적인 조치·조언를 구하시오.

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

화학적 성질

Pale Tan Powder

Originator

Geodon,Pfizer,USA

용도

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]

용도

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

용도

antipsychotic;Dopamine D2/serotonin 5-HT2 antagonist

정의

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 free base. The slurry was warmed to 65°C and held for 18 hours. The slurry was cooled to room temperature. The product was filtered and washed with 2x5-gallon portions of deionized water, and then air dried at 50°C for 30 hours. The dried product contained 4.4% water and the x-ray diffraction method confirmed that the desired product was obtained.

상표명

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

생물학적 활성

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).

Biochem/physiol Actions

Ziprasidone is an atypical antipsychotic; FDA approved for the treatment of schizophrenia.

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

원자재

준비 용품


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

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

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