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Synthesis of tirofiban hydrochloride

A technology of propionate and condensation reaction, applied in the direction of organic chemistry, organic chemistry method, etc., can solve the problems of complicated reaction operation, triphenylphosphine oxide by-products, etc., and achieve the effect of simple operation

Active Publication Date: 2020-06-05
WISDOM PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this route is more suitable for industrialization, the Mitsunobu reaction operation is complicated, and a large amount of triphenoxyphosphine by-products will be produced during post-reaction treatment.

Method used

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  • Synthesis of tirofiban hydrochloride
  • Synthesis of tirofiban hydrochloride
  • Synthesis of tirofiban hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0032] 1. Preparation of (S)-2-(n-butylsulfonylamino)-3-(4-(4-(pyridin-4-yl) butyl oxygen) phenyl) propionic acid ethyl ester (formula III, R 1 =Et,R 2 = ).

[0033] (S)-3-(4-chlorophenyl)-2-(n-butylsulfonylamino)-propionic acid ethyl ester (139.0g, 0.40mol), 4-pyridinebutanol (181.5g, 1.20mol) , CuI (3.80g, 19.95mmol), K 3 PO 4 (127.4g, 0.60mol) and N 1 ,N 2 - bis(naphthalene-1-ylmethyl) oxalamide (14.8g, 39.96mmol) was added to the reaction flask, followed by nitrogen replacement three times, then anhydrous DMSO (500mL) was added to the reaction flask, and the reaction system was again nitrogen Replace three times. Subsequently, the reaction system was heated to 100° C. for 24 h under stirring. After the reaction was over, the system was naturally cooled to room temperature. The reaction system was diluted with ethyl acetate (1.5 L), then filtered through celite. The filtrate was desolvated under reduced pressure to remove the organic solvent. The residue was add...

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Abstract

The invention relates to a method for preparing tirofiban hydrochloride. The method comprises the following steps: carrying out a condensation reaction between 4-pyridine butanol or 4-(pyridine-4-yl)-butyl-3- alkynyl-1-ol and (S)-3-(4-halogenated phenyl)-2-(n-butylsulfonylamino)-propionate in the presence of a copper reagent / alkali / additive / solvent to generate (S)-2-(n-butylsulfonylamino)-3-(4-(4-(pyridine-4-yl)butoxy)phenyl)-propionate or (S)-2-(n-butylsulfonylamino)-3-(4-((4-(pyridine-4-yl)-butyl-3-alkynyl-1-yl)oxo) phenyl) propionate.

Description

technical field [0001] The present invention relates to the synthesis of tirofiban hydrochloride. Background technique [0002] Tirofiban Hydrochloride Monohydrate (Tirofiban Hydrochloride Monohydrate, trade name Aggrastat) chemical name is (N-n-butylsulfonyl-O-4-(4-piperidinyl) butyl)-L-tyrosine hydrochloride monohydrate Hydrate, a reversible non-peptide platelet GPIIb / IIa receptor antagonist, was developed by the international pharmaceutical giant Merck in the 1990s and successfully approved by the US FDA in May 1998. Currently, the platelet antagonist The agent has been widely marketed and used in Switzerland, China, Germany and the Netherlands. The drug is suitable for patients with unstable angina or non-Q wave myocardial infarction to prevent cardiac ischemic events. Cardiac ischemic complications associated with sudden occlusion of treated coronary arteries. The structural formula of tirofiban hydrochloride is as follows: [0003] [0004] So far, multiple synt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/22C07D213/30
CPCC07D211/22C07D213/30C07B2200/07
Inventor 邱小龙李冰健左智伟张义森胡林刘文博邹平储玲玲张新刚王平
Owner WISDOM PHARM CO LTD
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