Synthetic compounds which bind to H. pylori, and uses thereof

Details Synthetic compounds which bind to H. pylori, and uses thereof Synthetic compounds which bind to H. pylori, and uses thereof

1993-03-15

1996-08-06

Robinson, Douglas W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 175, 536 179, 536 182, 5361231, 530300, 530322, 530350, 530363, C07H 1500, C07H 1506, C07H 1700, C07K 100

Patent

active

055435050

ABSTRACT:
The present invention provides a compound having the structure: ##STR1## wherein A is selected from the group consisting of (i) an amino acid bearing an .omega.-amino group or an .omega.--(C.dbd.O)-- group, (ii) an amino acid residue of a peptide, which residue bears an .omega.-amino group or an .omega.-(C.dbd.O)-- group, and (iii) an amino acid residue of a protein, which residue bears an .omega.-amino group or an .omega.-(C.dbd.O)-- group; wherein R.sub.1 is H, OH, NH.sub.2 or NHR.sub.4, where R.sub.4 is SO.sub.2 Ph, a linear or branched chain alkyl or acyl group, or an aryl group; wherein M is a saccharide wherein n is an integer from 0 to 18, and where n is greater than 1, each M is independently the same or different; wherein p is either 0 or 1; wherein R.sub.2, R.sub.3, R.sub.5 and R.sub.6 are independently the same or different and are H or OH, with the proviso that R.sub.2 and R.sub.3 are not both OH, and R.sub.5 and R.sub.6 are not both OH; wherein X and Y are independently the same or different and are H.sub.2 or O; and wherein k is an integer greater than or equal to 1, with the proviso that when A is an amino acid bearing an .omega.-amino group or an .omega.-(C.dbd.O)-- group, k is equal to 1.

REFERENCES:
Alper, Joseph, "New Bind for Ulcer Bacterium" Science, vol. 262, 1817 (17 Dec. 1993); U.S.A. (Exhibit B).
Altman, Lawrence K., "Stomach Microbe Offers Clues for Cancer as Well as Ulcers," The New York Times, C3 (Feb. 22, 1994); U.S.A. (Exhibit C).
Bernstein, Michael A., and Hall, Laurance D., "A general synthesis of model glycoproteins: coupling of alkenyl glycosides to proteins, using reductive ozonolysis followed by reductive amination with sodium cyanoborohydride," Carbohydrate Research, 78, C1-C3 (1980); The Netherlands (Exhibit D).
Boren, Thomas, Falk, Per, Roth, Kevin A., Larson, Goran, Normark, Staffan, "Attachment of Helicobacter pylori to Human Gastric Epithelium Mediated by Blood Group Antigens" Science, vol. 262, 1892-1895 (17 Dec. 1993); U.S.A. (Exhibit E).
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Falk, Per, Roth, Kevin A. Boren, Thomas, Westblom, T. Ulf, Gordon, Jeffrey T. and Normark, Staffan, "An in vitro adherence assay reveals that Helicobacter pylori exhibits cell lineage-specific tropism in the human gastric epithelium," Proc. Natl. Acad. Sci. U.S.A., vol. 90, 2035-2039 (Mar. 1993); U.S.A. (Exhibit H).
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Mahajan, R., Dixit, S., Khare, N. K. and Khare, A., "Synthesis of Neoglycoproteins as artificial Antigens," Carbohydrate Chemistry, vol. 13(1), 63-73 (1994); U.S.A. (Exhibit J).
Chemical Abstracts, vol. 109, No. 15, issued 1988, Ogawa eet al., "Glyco-sphingolipids Bearing a Lewis b Type Antigenic Determinant and a Process for their Preparation", p. 752, column 2, abstract No. 129595w, Jpn. Kokai Tokkyo Koho JP 63 51, 396.

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