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Method for separating single stereoisomer of Argatroban and polymorphic substance

An argatroban, separation technology, applied in the preparation of polymorph A and polymorph B, the application field of preparation of anticoagulant and antithrombotic drugs, can solve the problem of increased side effects and anticoagulant effect Advanced problems, to achieve the effect of saving energy consumption

Active Publication Date: 2012-01-25
BRIGHTGENE PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is now known that the anticoagulant effect of compound II is more than 4 times higher than that of compound I. Therefore, if the ratio of isomer I and isomer II cannot be strictly controlled, the risk of side effects will be greatly increased. probability

Method used

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  • Method for separating single stereoisomer of Argatroban and polymorphic substance
  • Method for separating single stereoisomer of Argatroban and polymorphic substance
  • Method for separating single stereoisomer of Argatroban and polymorphic substance

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Dissolve 10g argatroban (compound II content 35%) in 80ml methanol at 60°C, add 16ml pure water to the solution, mix well and slowly cool to room temperature, leave it overnight and then precipitate crystals, filter and collect It was dried to constant weight under vacuum to obtain 7.5 g of solid. HPLC analysis showed that the content of compound II was 45%.

Embodiment 2

[0044] Dissolve 1g argatroban (compound II content 35%) in 10ml methanol at 60°C, add 2ml absolute ethanol to the solution, mix well and slowly cool to room temperature, leave it for 1 hour and then precipitate crystals, filter After collection, it was dried to constant weight under vacuum to obtain 0.7 g of solid. HPLC analysis showed that the content of compound II was 41%.

Embodiment 3

[0046] Dissolve 1g argatroban (compound II content 35%) in 10ml methanol at 60°C, add 2ml anhydrous ether to the solution, mix well and slowly cool to room temperature, leave it for 1 hour and then precipitate crystals, filter After collection, it was dried to constant weight under vacuum to obtain 0.78 g of solid. HPLC analysis showed that the content of compound II was 39%.

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Abstract

The invention provides a new method for separating and purifying a single stereoisomer (namely, a compound II) of Argatroban from Argatroban.

Description

Technical field [0001] The present invention relates to a single stereoisomer of argatroban, a polymorph A and a polymorph B with a fixed composition of compound II, and their application in the preparation of anticoagulant and antithrombotic drugs. [0002] The present invention also relates to a new method for separating and purifying compound II from argatroban, and a method for preparing polymorph A and polymorph B. Background technique [0003] Argatroban is a chemically synthesized small molecule direct thrombin inhibitor that has better anticoagulant and antithrombotic effects than heparin. Argatroban is approved in Japan for the treatment of peripheral thrombosis and acute stroke, and is approved by the US FDA for the prevention and treatment of heparin-induced thrombocytopenia. [0004] The chemical name of Argatroban is: (2R,4R)-4-methyl-1-[N-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfon Acyl]-L-arginyl]-2-piperidine carboxylic acid [0005] Its structural formula is: ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/068C07K1/14
Inventor 袁建栋
Owner BRIGHTGENE PHARMA
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