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Carboxyalkylcyclodextrin polysulfates used as pharmaceuticals

A cyclodextrin and sulfate technology, which can be used in drug combinations, antipyretics, pharmaceutical formulations, etc., can solve problems such as reduced anticoagulant activity

Inactive Publication Date: 2011-12-28
ARCARIOS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the introduction of different alkyl groups did not prolong the activated partial thromboplastin time (aPTT) in vitro, suggesting a reduced anticoagulant activity compared with CDPS

Method used

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  • Carboxyalkylcyclodextrin polysulfates used as pharmaceuticals
  • Carboxyalkylcyclodextrin polysulfates used as pharmaceuticals
  • Carboxyalkylcyclodextrin polysulfates used as pharmaceuticals

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Example 1 - Sulfation of Carboxyethyl-β-Cyclodextrin

[0065] Heat pyridine sulfonate (sulfur trioxide pyridine complex) to 70-80°C in a water bath. Pyridine sulfonate (1000 mL) was added to a sidearm vessel which was mechanically stirred and maintained at 80°C with a water bath. Carboxyethyl-β-cyclodextrin with a degree of substitution of 3 (100 g) from Cyclolab Ltd. (Hungary) was slowly added with rapid stirring. The mixture was maintained at 80°C with stirring for 2.5 hours, then water (500 mL) was added. The preparation of embodiment 2-carboxyethyl sulfate-beta-cyclodextrin sodium salt

[0066] The reaction mixture obtained in Example 1 was poured into methanol (7500 mL) containing sodium acetate (750 g) while stirring rapidly. The resulting precipitate was isolated by filtration using a Buchner funnel, washed with methanol (2000 mL), air-dried, and then dried under vacuum. Then, dissolve the precipitate (carboxyethylsulfate-β-cyclodextrin sodium salt) in water ...

Embodiment 3

[0067] Activated carbon treatment of embodiment 3-carboxyethyl cyclodextrin polysulfate sodium salt

[0068] 2-Carboxyethyl-β-cyclodextrin polysulfate sodium salt (hereinafter referred to as "CE-CDPS") obtained in Example 2 was dissolved in water at a rate of 300 mg / mL. Add activated carbon (10g) per 100g of cyclodextrin polysulfate sodium salt. The mixture was stirred at room temperature for 30 minutes and filtered several times, including finally using a 0.2 μm filter, to remove the charcoal. The filtered cyclodextrin compound solution was slowly added to 5 volumes of stirring methanol. The mixture was stirred for 10 minutes. The resulting product was isolated by filtration, washed with methanol, and dried under vacuum. The elemental analysis data are shown in Table 1.

Embodiment 4

[0069] Comparative Elemental Analysis of Example 4-β-Cyclodextrin Derivatives

[0070] 2,3,6-tri-O-methyl-β-cyclodextrin (ME-CD) and 2,6-di-O-methyl-3-sulfate-β-cyclodextrin (ME-CD- 3-S) was purchased from Cyclolab Ltd (Hungary). 2,3-Di-O-methyl-6-sulfate-β-cyclodextrin (ME-CD-6-S was supplied by Regis Technologies Inc. (Morton Grove, IL, USA). 2-Hydroxypropyl -β-cyclodextrin (HP-CDPS) was provided by Sigma Chemical Company, and 6-monodeoxy-6-monoamino-β-cyclodextrin (MA-CDPS) was from Cyclolab Ltd. The elemental analysis data are shown in Table 1, Compare with the data of the purified 2-carboxyethyl-β-cyclodextrin polysulfate sodium salt obtained in Example 3.

[0071]

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Abstract

This invention relates to novel ss-cyclodextrin polysulfate compounds comprising from one to three 2-carboxyethyl substituents, and at least two sulfates groups per glucopyranose unit, which are useful as active ingredients for the treatment and / or prophylaxis of degenerative joint diseases, osteoarthritis, articular rheumatism, arthrosis or degenerative arthritis, or for the treatment of heparin-induced thrombocytopenia, or for cartilage repair or connective tissue repair.

Description

technical field [0001] The present invention relates to carboxyalkyl beta-cyclodextrin polysulfates and salts thereof, processes for their preparation, pharmaceutical compositions comprising therapeutically effective amounts of these compounds and said carboxyalkyl-beta-cyclodextrin compounds as active ingredients alone Or in combination with other therapeutic agents for the treatment and / or prevention of degenerative joint diseases, especially osteoarthritis, or for the treatment of heparin-induced thrombocytopenia, or for methods of cartilage repair or connective tissue repair. Background technique [0002] Cyclodextrins are a class of cyclic oligosaccharides and polysaccharides containing 5 or more D-glucopyranoside units linked by 1,4-glycosidic bonds. The most typical cyclodextrin contains 6-8 glucopyranoside units in a ring, forming a cone. In this class, β-cyclodextrins have 7 glucopyranoside units per ring. Typical sulfation procedures result in sulfation of one, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16A61K31/724A61P7/02A61P31/12A61P31/18A61P19/02
CPCC08B37/0012A61P19/02A61P29/00A61P31/12A61P31/18A61P43/00A61P7/00A61P7/02A61P7/04A61K31/724
Inventor D·叶列沃特A·L·韦尔布鲁真
Owner ARCARIOS
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