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Tafluprost

Tafluprost 구조식 이미지
카스 번호:
209860-87-7
상품명:
Tafluprost
동의어(영문):
TafL;MK2452;uprost;AFP-168;aflupros;TAFLUPROST;209860-87-7;Tafluprost fandachem;Tafluprost USP/EP/BP;He has fluprostaglandin
CBNumber:
CB3401660
분자식:
C25H34F2O5
포뮬러 무게:
452.53
MOL 파일:
209860-87-7.mol

Tafluprost 속성

끓는 점
552.9±50.0 °C(Predicted)
밀도
1.186
저장 조건
Sealed in dry,2-8°C
산도 계수 (pKa)
14.48±0.70(Predicted)

안전

Tafluprost C화학적 특성, 용도, 생산

개요

Glaucoma is second only to cataracts as a causative factor of blindness. By 2010, it is estimated that approximately 60 million people worldwide will be afflicted by glaucoma, so effective treatments should garner a large market. PG analogs have been widely used for lowering IOP by increasing uveoscleral outflow through agonism of the prostanoid FP receptor, and currently marketed versions include latanoprost, unoprostone isopropyl ester, bimatoprost, and travoprost. Compared to the carboxylic acid of latanaprost (Ki=4.7 nM), the carboxylic acid of tafluprost displayed a 10-fold greater affinity for the prostanoid FP receptor (Ki=0.4 nM). The synthesis of tafluprost begins with a Wittig condensation of the protected bicyclic lactone carbaldehyde with a dimethyl phosphonate ketone derivative.
Compared to the carboxylic acid of latanaprost (Ki 4.7 nM), the carboxylic acid of tafluprost displayed a 10-fold greater affinity for the prostanoid FP receptor (Ki 0.4 nM). The synthesis of tafluprost begins with a Wittig condensation of the protected bicyclic lactone carbaldehyde with a dimethyl phosphonate ketone derivative. The bottom appendage is then completed by the fluorination of the ketone with morpholino-sulfur trifluoride. Hydrolysis of the benzoate ester protecting group liberates the hydroxy group, and reduction of the lactone is accomplished with aluminum hydride to generate the lactol. Condensation of this intermediate with the phosphonium salt of the acid side chain generates the free acid, or active ingredient, which is subsequently esterified with 2-iodopropane in the presence of DBU. .

Originator

Santen/Asahi Glass (Japan)

용도

Tafluprost is a novel prostanoid used in the treatment of glaucoma and is the first prostanoid to be released in a preservative free-formula.

정의

ChEBI: A prostaglandin Falpha that is prostaglandin F2alpha in which the carboxylic acid function has been converted to the corresponding isopropyl ester and the 3-hydroxy-1-octenyl side- hain is substituted by 3,3-difluoro-4-phenoxybut-1-enyl. Used for treatment of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

상표명

Taflotan

Chemical Synthesis

The synthesis was initiated from the Corey aldehyde 131. Horner-Emmons condensation of the bicyclic carbaldehyde 131 with the dimethyl phosphonate 132 using NaH in DMF gave enone 133 in 90% yield. Fluorination of the enone 133 was accomplished upon reaction with morpholino-sulfur trifluoride (134) in chloroform to yield the corresponding difluorinated compound 135. Hydrolysis of the benzoate ester group of 135 with K2CO3 in methanol at room temperature afforded alcohol 136 in 71% yield from 133. Reduction of the lactone group of 136 with diisobutyl aluminum hydride (DIBAL) in THF/toluene gave lactol 137 in 83% yield. Lactol 137 was condensed with the phosphonium ylide prepared by deprotonation of phosphonium salt 138 with sodium bis(trimethylsilyl)amide (NaHMDS) in THF/toluene to give the prostaglandin F2-alpha derivative 139 in excellent Z/E selectivity (99:1). The synthesis was completed by esterification of compound 139 with isopropyl iodide and DBU in acetone to provide tafluprost (XVIII) in 72% yield.

Tafluprost 준비 용품 및 원자재

원자재

준비 용품


Tafluprost 공급 업체

글로벌( 183)공급 업체
공급자 전화 팩스 이메일 국가 제품 수 이점
Shanghai finete Pharmaceutical Co., Ltd.
+86-18221039705
- sales@finetechpharm.com CHINA 139 55
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 9150 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26782 60
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3623 58
career henan chemical co
+86-0371-55982848
sales@coreychem.com China 29953 58
Zhejiang ZETian Fine Chemicals Co. LTD
18957127338
stella@zetchem.com China 2008 58
Biochempartner
0086-13720134139
candy@biochempartner.com CHINA 968 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
HubeiwidelychemicaltechnologyCo.,Ltd
18627774460
faith@widelychemical.com CHINA 743 58

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