Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1992-02-25
1993-12-07
Griffin, Ronald W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 185, 536 186, 536123, 5361231, 53612313, 536124, C07H 306, C07H 1306, C07H 1504
Patent
active
052684610
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention pertains to alkylated oligosaccharides, and more particularly, to alkyl-etherificated oligosaccharides wherein the hydroxy group located at the 1-position in the terminal sugar moiety of the oligosaccharide is alkyl-etherificated. The present invention also relates to alkylated oligosaccharides and the acetyl derivatives of the same which are useful as the raw material for producing lowly toxic surfactants or medicines.
BACKGROUND OF THE INVENTION
Heretofore, it has been known that alkylated sugars are useful as surfactants, and for this reason, the sugars employed as the raw materials have been limited to inexpensive ones. The prior art documents related to the alkylated sugars include: U.S. Pat. No. 3,219,656; U.S. Pat. No. 3,547,828; U.S. Pat. No. 3,839,318; Japanese Pat. Application First Publication No. 58-194901; B. W. LEW et al, J. Am. Oil. Chem. Soc. vol. 47, 163-167 (1970); and the like. These prior art documents pertain to glycosides which are products obtained from reactions between monosaccharides and alcohols. In these prior art documents, although it is disclosed that a small amount of the products obtained from the reactions between the alcohols and the oligosaccharide mainly produced by self-polymerization-reacting the sugars is by-produced, there are no descriptions about the structures, and stereo-and regio- chemistries of the by-product oligosaccharides.
In addition, the oligosaccharides employed as the raw materials of the present invention can be produced by various conventional methods for manufacturing the same. For example, .beta.(1.fwdarw.3) oligoglucose can be produced by decomposition of curdlan, laminarane or the like using the enzyme produced by microorganism belonging to the group Streptomyces, or by acid decomposition of curdlan, laminarane or the like.
In addition, a galactose type oligosaccharide having a lactose moiety, .beta.-D-galactosyl-.beta.(1.fwdarw.4)-D-galactosyl-.beta.(1.fwdarw.4)-D-g lucose can be produced by the method disclosed in A. Ballio et al. (Tetrahedron, 9, 125, 1960), J. H. Pazur et al. (J. Am. Chem. Soc., 80, 119, 1958), J. G. Collins et al. (Carbohydr. Res., 92, 136, 1981), or Japanese Pat. Application First Publication No. 2-79992 filed by the present applicants. In addition, .beta.-D-galactosyl-.beta.(1.fwdarw.4)-D-galactosyl-.beta.(1.fwdarw.4)-D-g alactosyl-.beta.(1.fwdarw.4)-D-glucose and the like can be produced by the methods disclosed in Japanese Patent Application First Publication No. 60-251896 filed by the present applicants.
However, in the documents described above, there is no description of an alkylated oligosaccharide wherein the oligosaccharide described above is alkylated, nor is a method for producing the same disclosed.
In addition, a number of reports have recently been published wherein the polysaccharide sulfates are useful as the medical agents for Acquired Immune Deficiency Syndrome (AIDS). For this reason, the sulfates of polysaccharides have attracted much attention.
However, these polysaccharides have several disadvantages. They have a strong tendency to act as an anticoagulant, and are difficult to administer due to their poor absorption within a living organism because of molecular weight in excess of ten thousand or more.
It is an object of the present invention to provide a novel alkylated oligosaccharide and the acetyl derivative of the same, having low decomposition properties in a living organism, and which are useful as the raw materials for producing medicines having improved absorption in a living organism.
DESCRIPTION OF THE INVENTION
In order to solve the above described disadvantages of the polysaccharide sulfates, it is an object of the present invention to provide a novel alkylated oligosaccharide and the acetyl derivative of the same having low decomposition-properties in a living organism, improved absorption within a living organism and which are useful as the raw materials for producing medicines.
The alkylated oligosaccharides and the acetyl derivatives
REFERENCES:
patent: 3723617 (1973-03-01), Sutton
patent: 4710491 (1987-12-01), Lockhoff et al.
patent: 4803263 (1989-02-01), Thiem et al.
patent: 4840815 (1989-06-01), Meyer et al.
patent: 4866165 (1989-09-01), Luders
patent: 4874852 (1989-10-01), Kinomura et al.
patent: 4889651 (1989-12-01), Broze
patent: 4939245 (1990-07-01), Rasche et al.
patent: 4959459 (1990-09-01), David et al.
patent: 4980462 (1990-12-01), Karlsson et al.
patent: 4990605 (1991-02-01), Lueders
patent: 5138046 (1992-08-01), Wuest et al.
Adachi Koichiro
Ikushima Naoya
Katsuraya Kaname
Shoji Tadao
Takahashi Nahoko
Dainippon Ink & Chemicals Inc.
Griffin Ronald W.
LandOfFree
Alkylated oligosaccharides and acetyl derivatives of the same does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Alkylated oligosaccharides and acetyl derivatives of the same, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Alkylated oligosaccharides and acetyl derivatives of the same will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2016646