Glycomed, Inc.

Narasinga Rao

John H Musser

Mark Brian Anderson

Peng Cho Tang

John Joseph Naleway

Daniel E Levy

Ole Hindsgaul

Margaret Moreland

Brian K Brandley

Michael Tiemeyer

Morten P Meldal

Stuart J Swiedler

Hans Schweingruber

Klaus Bock

Jing Rong Cui

Triterpenoid acid derivatives are described that exhibit dual pharmacophobic activities, specifically selectin ligand and leukotriene biosynthetic inhibitory activities, and that thus have significant applications for the treatment or prevention of certain diseases including cancer and diseases associated with the inflammatory process as well as applications for the diagnosis of disease.

Derivatives of triterpenoid acids and uses thereof.

Compounds that possess selectin binding activity are described that have a three-dimensionally stable configuration for sialic acid and fucose, or analogs, derivatives, or mimics of these groups, such that sialic acid and fucose or their mimics are separated by a linker that permits binding between those groups and the selecting, such compounds being represented by the following general structural formula I: ##STR1##

Sialyl lewis-x mimetics containing naphthyl backbones

Glycopeptides having the following structure are described: ##STR1## wherein: X.sub.1 is hydrogen, an acetyl group, an acyl group or amino acid; R is .alpha.-L-fucose, .alpha.-D-fucose, .beta.-L-fucose or .beta.-D-fucose, wherein R is O-glucosidically linked to A.sub.1 ; A.sub.1 is serine, threonine, tyrosine, hydroxyproline, asparagine, glutamine, homeoserine and hydroxylysine; A.sub.2 is a glycine, an L-amino acid, a D-amino acid or a modified amino acid; A.sub.3 is L or D aspartic acid, glycine or glutamic acid; and X.sub.2 is a hydroxyl, an amine or an amino acid.

Library of glyco-peptides useful for identification of cell adhesion

Sialyl Lewis.sup.x mimetics containing phenyl backbones

Derivatives of triterpenoid acids and uses thereof

2-Chloromethyl-3-(tri-O-benzyl-.alpha.-L-C-fucopyranoside)-1-propene and methods of making the same are described. Methods of combining this substituted fucopyranose with triterpenoid acid also are described.

Substituted fucopyranosides

Methods of treating diseases using triterpenoid acid derivatives

Ligands that bind to human selectin receptors are disclosed. The ligands are formulated with excipient carriers to form compositions which are administered to treated condition such as inflammation. The ligands have the structural formula III ##STR1## or molecules which have hydrogen bond donor groups equivalent to the circled groups with respect to their ability to form hydrogen bonds with a selectin under physiological conditions.

Methods of treating inflammation using selection binding compounds

Triterpenoid acid derivatives have been found to have structures similar to natural ligands to the extent that these derivatives bind to natural selectin receptors including endothelial leukocyte adhesion molecule-1 (ELAM-1) and leukocyte/endothelial cell adhesion molecule-1 (LECAM-1). The molecules can be administered to the patients by themselves or in pharmaceutical formulations in order to alleviate inflammation and/or treat other abnormalities associated with the excessive binding of leukocytes to endothelial receptors.

Derivatives of triterpenoid acids as inhibitors of cell-adhesion

Triterpenoid acid derivatives have been found to have structures similar to natural ligands to the extent that these derivatives bind to natural selectin receptors including endothelial leukocyte adhesion molecule-1 (ELAM-1) and leukocyte/endothelial cell adhesion molecule-1 (LECAM-1). The molecules can be administered to the patients by themselves or in pharmaceutical formulations; in order to alleviate inflammation and/or treat other abnormalities associated with the excessive binding of leukocytes to endothelial receptors.

Derivatives of anthraquinone and anthracene are synthesized and formulated into pharmaceutical formulations. When the formulations are administered the derivatives act as ligands binding to an interrupting the biological chain of events associated with selectin receptors in the human body.

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Alameda, CA, United States of America

Narasinga Rao