Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Reexamination Certificate
1999-03-08
2002-07-09
Fonda, Kathleen K. (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
C536S017200, C536S017900, C536S018500, C514S024000, C514S025000
Reexamination Certificate
active
06417339
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to dendrimers based on saccharides, a process for the preparation of the same as well as use thereof.
BACKGROUND OF THE INVENTION
When organic compounds are synthesized, the products are often obtained as mixtures such as racemic mixtures, i.e., as mixtures of enantiomers. Enantiomers may differ only little regarding physical properties but differ substantially with respect to their physiological effects. Thus, one enantiomer may be toxic whereas the other enantiomer may have a therapeutic effect. Therefore, the separation of enantiomers is desirable. Many attempts have been made to achieve this goal. However, the prevailing results are not satisfactory.
It is an object of the present invention to provide a product by which mixtures of products, particularly racemates, can be separated effectively.
According to the invention, this is achieved by the subject matter defined in the claims.
SUMMARY OF THE INVENTION
The present invention relates to a dendrimer comprising an initiator core having at least two functional groups and at least two saccharides.
Dendrimers are three-dimensional, highly ordered oligomeric compounds and polymeric compounds, respectively, which form on the basis of an initiator core that has several reactive groups. Substances are attached to these groups. Dendrimers of the first generation are obtained in this way. It is possible to bind to the substances of the first-generation dendrimers further substances and/or further initiator cores that can then be linked with further substances. In this connection, dendrimers of the second generation are obtained. Dendrimers of higher generations are obtained when this reaction sequence is repeated.
The term “initiator core having at least two functional groups” relates to cyclic compounds having at least two functional groups, e.g., hydroxy groups, amino groups, carboxylic acid groups, metallo-organic groups and/or halide groups, particularly 3, 4, 5 or 6 functional groups. Examples of initiator cores are cyclic initiator core saccharides, i.e., cyclic saccharides, that are used as the initiator core and cyclic aliphatic compounds. Representatives of cyclic initiator core saccharides are cyclic monosaccharides in all stereoisomeric and enantiomeric forms, e.g., cyclic pentoses and hexoses, such as &agr;- and &bgr;-D-glucose and derivatives thereof. Representative cyclic aliphatic compounds include cycloalkanes, such as trihydroxycycloalkanes, e.g., 1,3,5-trihydroxycycloalkanes, preferably 1,3,5-trihydroxycyclohexane, inositols, more preferably myo-inositol, as well as derivatives thereof.
REFERENCES:
patent: 4410688 (1983-10-01), Denkewalter et al.
patent: 6008203 (1999-12-01), Magnani et al.
patent: 0601 417 (1994-06-01), None
patent: 0 649 854 (1995-04-01), None
patent: WO 95/05182 (1995-02-01), None
patent: WO 95/25763 (1995-09-01), None
D.R. Bundle, et al.,Carbohydrate Chemistry, Ed. J. Thiem, 1990.
Chem. Absracts, vol. 125, No. 26, 1996, No. 125:329642b.
Patent Abstracts of Japan, C-1025, Feb. 10, 1993, vol. 17, No. 67, JP 4-273889 A, Sep. 30, 1992.
Patent Abstracts of Japan, C-1190, Apr. 13, 1994, vol. 18, No. 209, JP 6-9675, Jan. 18, 1994.
Aoi, K., et al., Globular Carbohydrate Macromolecule Sugar Balls . 1. Synthesis of Novel Sugar-Persubstituted Poly(amido amine) Dendrimers, Macromolecule 28:5391-5393 (1995).
Ashton, P.R., A Convergent Synthesis of a Carbohydrate-Containing Dendrimer, Angew. Chem. Int. Ed. Eng. 36(7):732-735 (1997).
Ashton, P.R., A Convergent Synthesis of Carbohydrate-Containing Dendrimers, Chem Eur. J. 2(2):1115-1128 (1996).
Ballou, C.E., The Absolute Configuration of the myo-Inositol 1- Phosphates and Confirmation of the Bornesitol Configurations1, J. Am. Chem. Soc. 82:3333-3335 (1960).
Lindhorst, T.K., Glycocoating of Oligovalent Amines: Synthesis of Thiourea-Bridged Cluster Glycosides from Glycosyl Isothiocyanates, Angew. Chem. Int. Ed. 35(17): 1953-1956 (1996).
Menzler, S., Beta-Galactosidase Catalysed Synthesis of Branched Oligosaccharide Analogues, Biotechnology Letters 11(2):269-272 (1997).
Roy, R., Glycodendrimers: A New Class of Biopolymers, Polymer News 21:226-232 (1996).
Roy, R., Synthesis of Hyper-Branched Dendritic Lactosides, Tetrahedron Letters 36(25):4377-4380 (1995).
Roy, R., Solid-Phase Synthesis of Dendritic Sialoside Inhibitors of Influenza A Virus Haemagglutinin, J. Chem. Soc. 1869-1872 (1993).
Toyokuni, T., Synthetic Carbohydrate Vaccines Based on Tumour-Associated Antigens, Chem. Soc. Rev. 231-242 (1995).
Zanini, D., Syntheses and Biological Properties of Glyco-Dendrimers, Plym Mater. Sci. Eng. 73:82-83 (1995).
Zanini, D., Synthesis of novel Dendritic Glycosides, Tetrahedron Letters 36(41):7383-7386 (1995).
Zanini, D., Novel Dendritic &agr;-Sialosides: Synthesis of Glycodendrimers Based on a 3,3-Iminobis(propylamine) Core, J. Org. Chem. 61:7348-7354 (1996).
Zanini, D., Chemoenzymatic Synthesis and Lectin Binding Properties of Dendritic N-Acetyllactosamine, Bioconjugate Chem. 8:187-192 (1997).
Gschrey Markus
Mier Walter
Von der Lieth Willi
Wiessler Manfred
Deutsches Krebsforschungzentrum Stiftung des Offentlichen Rechts
Fonda Kathleen K.
Halluin Albert P.
Howrey Simon Arnold & White , LLP
Kung Vilao T.
LandOfFree
Dendrimers based on saccharides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Dendrimers based on saccharides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Dendrimers based on saccharides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2844372