Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Patent
1997-12-18
1999-10-26
Nutter, Nathan M.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
525 543, 536 41, C08G 6508, C08G 6532
Patent
active
059730692
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to an oligomer or polymer (heterotelechelic oligomer or polymer) which has a sugar on one end and a different functional group on the other end, and a method for the production of said oligomer or polymer.
Prior Arts
Polyethyleneoxide has properties such as solubility in water and non-immunogenicity, and its applications in biology and medical engineering are noted, such as its use as a modifier of biologically active substances such as proteins and drugs.
For example, it is known that when protein is modified with, polyethylene glycol, its immunogenicity is markedly reduced (Protein Hybrid, Yuji Inada, Hirotomo Maeda and Kyoritsu Shuppan (1988)). When the polyethylene oxide is bonded to protein in this way, a function group to react with the protein terminal must be on the end of the polyethylene oxide. Generally, various functional groups such as carboxyl group, amino group, hydroxyl group and mercapto group are present on the surface of a protein, and the selection of the functional group when reacting with the polyethylene oxide often has a great influence on the physiological activation of that protein.
Currently, most of the polyethylene oxide derivatives which are being engineered have a hydroxyl group on both ends, or a non reactive alkoxy group on one end and a hydroxyl group on the other end. Since the hydroxyl group has low reactivity compared to the aldehyde group and the amino group, there have been attempts to convert it to another functional group (Synth. Commun., 22(16), 2417-2424 (1992); J. Bioact. Compat. Polym., 5(2) 227-231 (1990). The manner of the reaction or use of polyethylene oxide has been disadvantageously limited when it is utilized as a modifier of protein in the above-mentioned way.
Furthermore, the importance of the hetero bonding to link a protein having a certain function with a compound having another function such as an antibody via polyethylene oxide has recently been noted. In this case, the polyethylene oxide derivative having a different functional groups on both ends is important. The method using a polyethylene oxide having a hydroxyl group at both ends as the raw material is used in order to synthesize this type of heteropolyethylene oxide (Poly(ethylene glycol) Chemistry; JM/Harris, Plenum Press, 1992). The product obtained by this type of method is, however, a mixture of unreacted matter, side reaction matter and over reaction matter modified on its both ends, and, therefore, this product needs to be refined by column operation or the like so that the desired product may be isolated, which process causes a large problem with yield and purity.
To overcome these types of problems, the inventors recently polymerized polyethylene oxide with an alkali metal salt of amino or alcohol having a function group as an initiator, and discovered a method to synthesize heteropolyethylene oxide quantitatively having different functional groups on both ends such as amino group, aldehyde group, mercapto group, carboxyl group and hydroxyl group (Japanese Patent Application No. 5-009168; Tokugan 5-194977; Tokugan 6-94532; Tokugan 6-117262; and Tokugan 6-228465).
However, quantitative synthesis of heteropolyethylene oxide having a sugar residue on one end has not yet been performed. Because of the characteristic interaction and affinity between the type of sugar and each component in the body, a compound having a characteristic affinity for biological components and having high bioavailability can be attained if a sugar group can be quantitatively introduced to one end of polyethylene oxide and a reactive functional group to the other end; such a compound would be a material which can be expected to be applied to carriers for drug delivery which have targeting properties and to precursors of diagnostic materials and the like.
The objective of this invention is therefore to produce a (heterotelechelic) polyethylene oxide derivative and a polyoxyethylene-polyester derivative having a sugar residue on one end and a reactive functi
REFERENCES:
patent: 5037969 (1991-08-01), Minami et al.
patent: 5410016 (1995-04-01), Hubbell et al.
Kataoka Kazunori
Kato Masao
Nagasaki Yukio
Nakamura Teruo
Okano Teruo
Kazunori Kataoka
Nutter Nathan M.
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