Modified amino acids and compositions comprising the same for delivering active agents
AssigneeEmisphere Technologies, Inc.
InventorsAndrea Leone-Bay, Koc-Kan Ho, Jeffery Bruce Press, Nai-Fang Wang
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Abstract
The present invention provides modified amino acids for delivering active agents, and particularly biologically or chemically active agents. The preferred modified amino acids of the present invention include N-acylated or sulfonated amino acids. These modified amino acids are used as carriers to facilitate the delivery of a cargo to a target. Such modified amino acids are well suited to form non-covalent mixtures with biologically-active agents for oral administration to animals. Methods for the preparation and administration of the modified amino acids and compositions including the same are also provided.
Claims30
A compound selected from the group consisting of ##STR11## and salts thereof.
A poly amino acid comprising at least one residue derived from at least one compound selected from the group consisting of ##STR12## and salts thereof.
A composition comprising
- (a) an active agent;
- and
- (b) a compound selected from the group consisting of ##STR13## and salts thereof.
A composition comprising
- (a) an active agent;
- and
- (b) a poly amino acid comprising at least one residue derived from an amino acid selected from the group consisting of ##STR14## and salts thereof.
A method for preparing a compound having the formula ##STR15## wherein Y is ##STR16## R.sup.1 is C.sub.3 -C.sub.24 alkyl, C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkyne, cycloalkyl, or aromatic;
- R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl, or C.sub.2 -C.sub.4 alkenyl;
- and
- R.sup.3 is C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.10 cycloalkyl, aryl, thienyl, pyrrolo, or pyridyl, where R.sup.3 is optionally substituted by one or more C.sub.1 -C.sub.5 alkyl group, C.sub.2 -C.sub.4 alkenyl group, F, Cl, OH, SO.sub.2, COOH and SO.sub.3 H;
- said method comprising
- (a) reacting in water and the presence of a base, a compound having the formula ##STR17## with a compound having the formula
- R.sup.3 --Y--X,
- wherein Y, R.sup.1, R.sup.2, and R.sup.3 are as above and X is a leaving group.
A composition for oral delivery of a biologically active agent, said composition comprising
- (a) a biologically active agent;
- and
- (b) an oral delivery effective amount of at least one compound selected from the group consisting of ##STR18## a poly amino acid derived from at least one compound selected from the group consisting of compounds V, XXXI, and XXXIII, and salts thereof,
- wherein said biologically active agent comprises at least one peptide, mucopolysaccharide, carbohydrate, or lipid.
Dependencies are inferred from the claim text.