121785-72-6

Usage

Uses

The 21S-stereoisomer

Upstream product

• 120267-95-0 Boc-Arg(Z)2-OH 
• 1448301-07-2 C₂₃H₃₅N₇O₇S 

Relevant academic research and scientific papers

Argatroban refining method

The invention relates to an argatroban refining method which comprises the following steps: decoloring a crude product of argatroban, and removing residual metallic palladium in the crude product of argatroban so as to obtain residues; dissolving the residues into ethanol, adjusting the pH value to be 6-7 by using a sodium bicarbonate solution, filtering, and removing glacial acetic acid left inthe residues so as to obtain white filter cakes; further dissolving the white filter cakes into a solvent, slowly cooling to a room temperature, keeping the temperature for 1-1.5 hours at 0-5 DEG C, and crystallizing so as to obtain a hydrate crude product; finally mixing the hydrate crude product, water and ethanol, carrying out stirring backflow for 1-1.5 hours, cooling to a room temperature, keeping the temperature for 0-5 DEG C for 1.1.5 hours, removing possible salts in the hydrate crude product, and purifying the refined argatroban till the purity is 99.5% or greater.

Efficient Diastereoselective Three-Component Synthesis of Pipecolic Amides

An efficient Ugi-type three-component reaction (U-3CR) for the synthesis of pipecolic amides is reported. The U-3CR between electronically diverse isocyanides, carboxylic acids and 4-substituted Δ1-piperideines proceeds in a highly diastereoselective fashion. The Δ1-piperideines are obtained by NCS-mediated oxidation of the corresponding 4-substituted piperidines, which in turn are generated by an efficient two-step procedure involving the alkylation of 4-picoline and subsequent catalytic hydrogenation of the pyridine ring. We demonstrate the utility of this U-3CR, in combination with the convertible isocyanide 2-bromo-6-isocyanopyridine, in the synthesis of the anticoagulant argatroban.

USE OF 21 (S) ARGATROBAN FOR TREATING THROMBOSIS AND INHIBITING PLATELET AGGREGATION

This invention refers to the preparation of a direct thrombin inhibitor, especially the application of a thrombin inhibitor of 21 (s) Argatroban. The chemical name of 21(S) Argatroban is: (2R, 4R) -1- { (2S) -5- [ ( Aminoiminomethyl) amino] -1-oxo-2-{ [ (3S) -1, 2, 3, 4-tetrahydro-3-methyl-8- quinolinyl] sulf onyl] amino] pentyl] -4-methyl-2-piperidine carboxylic acid, and the supplies which can be accepted in medicine. The 21(S) prolongation of coagulation time of whole blood (CT) is twice as long as 21 (R) 's, prolongation of recalcif ication time (RT) is three times of 21 (R) 's, extending prothrombin time (PT) is twice as 21 (R) 's, prolongation of thrombin time (TT) is little stronger than 21 (R) and prolongation of kaolin partial thromboplastin time (APTT) is twice as 21(R). Anticoagulation action of 21(S) Argatroban is 2-3 times of 21(R). Therefore, the 21 (S) isomer of Argatroban can be used as a new generation of direct thrombin inhibitor.