Algin oligosaccharides and the derivatives thereof as well as the manufacture and the use of the same

Patent metadata

Field	Value
Publication number	US-9493496-B2
Application number	US-201414482610-A
Country	US
Kind code	B2
Filing date	Sep 10, 2014
Priority date	Mar 24, 2004
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

The invention provides an alginate oligosaccharide and its derivatives with the degree of polymerization ranging from 2 to 22. The alginate oligosaccharide is composed of β-D-mannuronic acid linked by 1,4 glycosidic bonds. The derivatives with the reduced terminal in position 1 of carboxyl radical can be prepared by oxidative degradation. The invention also provides a process for preparing the alginate oligosaccharide and its derivatives, which includes the procedure that an alginate solution is reacted for 2 to 6 h in an autoclave at pH 2˜6 and the temperature of 100˜120° C., and adjusted pH to 7 after the reaction is stopped, after which the resultant oligosaccharide is oxidized in the presence of an oxidant to obtain an oxidative product. The alginate oligosaccharide and its derivatives of the invention can be used in the manufacture of a medicament for the prophylaxis and treatment of AD and diabetes.

First claim

We claim:

1. An alginate oligosaccharide or its derivatives represented by formula (I) or pharmaceutically-acceptable salts thereof, said oligosaccharide is composed of β-D-mannuronic acid linked by 1,4 glycosidic bonds, as shown by the following formula (I):

characterized in that the reduced terminal in position 1 of said alginate oligosaccharide is carboxyl radical, as shown by the following formula (II):

wherein, n represents a integer of 0 or 1 to 19.

2. A pharmaceutical composition containing an effective amount of the alginate oligosaccharide or its derivatives according to claim 1 , and pharmaceutically-acceptable carriers.

3. The pharmaceutical composition according to claim 2 , characterized in that the composition is any one of a medicament for the prophylaxis and treatment of AD, an amyloid-β protein fibrils forming inhibitor, a medicament for the prophylaxis and treatment of diabetes, an islet amyloid protein fibrils forming inhibitor and a fibrils disaggregating promoter.

4. Alginate oligosaccharide derivatives or their pharmaceutically-acceptable salts made by the following process:
an alginate solution is reacted for about 2 to 6 h in an autoclave at pH 2-6 and the temperature of about 100˜120° C.,
adjusted pH to about 7 after the reaction is stopped, and
an oxidant is added and reacted for 15 min to 2 h at the temperature of 100˜120° C.,
wherein the alginate oligosaccharide derivatives are composed of β-D-mannuronic acid linked by 1,4 glycosidic bonds, wherein the reduced terminal in position 1 is carboxyl radical, as shown by the following formula II:

wherein, n represents 0 or an integer of 1 to 19.

Assignees

• Ocean Univ China

Inventors

• Geng Meiyu
• Guan Huashi
• Xin Xianliang
• Yang Zhao
• Sun Guangqiang

Classifications

• A61P5/50

  for increasing or potentiating the activity of insulin · CPC title

• A61P3/10

  for hyperglycaemia, e.g. antidiabetics · CPC title

• A61P25/28

  for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia · CPC title

• A61K31/734

  Alginic acid · CPC title

• A61K31/715 Primary

  Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters · CPC title