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Anticoagulant compounds

A compound and solvate technology, applied in the field of anticoagulant oligosaccharides, can solve problems such as decreased bioavailability and inability to absorb

Inactive Publication Date: 2009-09-16
ENDOTIS PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Despite the pharmacokinetic advantages of using LMWHs, they are not absorbed when given orally, so they can only be given parenterally
Therefore, despite their good antithrombic properties, heparin and LMWH face decreased bioavailability after oral administration

Method used

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  • Anticoagulant compounds
  • Anticoagulant compounds
  • Anticoagulant compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0588] This example was prepared from Example 2 according to method T (yield: 39%).

[0589] 1 H NMR (400MHz, CD 3 OD, ppm), δ: 5.46-5.38 (width s, 1H, H-1), 5.00-4.84 (m, 3H, H-1).

[0590] ESI-MS, negative mode, m / z: 925.7 [M+2DBA-4H] 2- , 861.1 [M+DBA-3H] 2- , 796.5 [M-2H] 2-

Embodiment 2

[0592] This example was prepared according to method P (yield: 91%).

[0593] 1 H NMR (400MHz, CD 3 OD, ppm), δ: 5.40 (d, 1H, J=3.6Hz, H-1Glc III ), 5.18 (d, 1H, J=3.4Hz, H-1Glc V ), 4.96(s, 1H, H-1ManUA II ), 4.92 (d, 1H, J=3.4Hz, H-1Glc I ), 4.77 (1H, H-1Glc IV ).

[0594] ESI-MS, negative mode, m / z: 1061.2 [M+2DBA-4H] 2- , 996.6[M+DBA-3H] 2- .

Embodiment 3

[0596] This example was prepared according to method P (yield: 85%).

[0597] 1 H NMR (400MHz, CD 3 OD, ppm), δ: 5.39-5.34 (wide s, 1H, H-1), 5.15 (d, 1H, J=3.2Hz, H-1), 5.00 (s, 1H, H-1), 4.94- 4.87 (m, 2H, H-1), 4.72 (1H, H-1).

[0598] ESI-MS, negative mode, m / z: 1061.2 [M+2DBA-4H] 2- , 996.6[M+DBA-3H] 2- .

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Abstract

The present invention is concerned with anticoagulants ( i.e. substances that stop blood from clotting). More specifically, the present invention is concerned with orally available antithrombic oligosaccharides.

Description

[0001] All documents cited are hereby incorporated by reference in their entirety. technical field [0002] The present invention relates to anticoagulants (ie substances that prevent blood from clotting). In particular, the present invention relates to orally administered anticoagulant oligosaccharides. Background technique [0003] Heparin is an anticoagulant and is a natural sulfated polysaccharide belonging to the glycosaminoglycan family. Heparin acts as a regulator to prevent massive clotting of the blood, thereby avoiding clot formation. The anticoagulant activity of heparin is reflected by its accelerated inhibition of several proteases in the blood-coagulation cascade, including factor Xa and thrombin. [0004] Heparin and heparin-derived drugs inhibit factor Xa activity by attaching to specific binding domains of antithrombin (AT). Once heparin or heparin-derived drugs adhere to specific binding regions of antithrombin, they induce conformational changes in anti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H11/00C07H3/06A61K31/702A61P7/02
CPCC07H3/06C07H11/00A61P7/02A61P9/00A61P9/10A61K31/702
Inventor M·佩蒂图G·迪布勒克O·凯罗勒S·扎梅尔
Owner ENDOTIS PHARMA
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