Inhibitors of dipeptidyl-aminopeptidase type IV
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Nov 30, 2004
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Oct 15, 1997
filing date -
Oct 22, 1991
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Abstract
An inhibitory compound having the structure: Group I-Group II. Group I has the structure: ##STR1## where H represents a hydrogen; C represents a carbon; O represents an oxygen; N represents a nitrogen; each R, independently, is chosen from the group consisting of the R groups of an amino acid, including proline; each broken line, independently, represents a bond to an H or a bond to one R group, and each H' represents that bond or a hydrogen; and p is an integer between 0 and 4 inclusive. Alternatively Group I has the structure: ##STR2## where n is between 0 and 3 inclusive, each G2 and G3 independently is H or C1-3 (one to three carbon atoms) alkyl, G1 is NH3 (H3 represents three hydrogens), ##STR3## (H2 represents two hydrogens), or ##STR4## where G5 and G6 can be NH, H, or C1-3 alkyl or alkenyl with one or more carbons substituted with a nitrogen. G1 bears a charge, and G1 and Group II do not form a covalently bonded ring structure at pH 7.0. Group I may also have the structure: ##STR5## where one or two of the a, b, c, d, e, and f group is N, and the rest are C, and each S1-S6 independently is H or C1-C3 alkyl. Group I may also include a five membered unsaturated ring having two nitrogen atoms. Group II has the structure: ##STR6## where T is a group of the formula: ##STR7## where each D1 and D2, independently, is a hydroxyl group or a group which is capable of being hydrolysed to a hydroxyl group in aqueous solution at physiological pH; a group of the formula: ##STR8## where G is either H, fluorine (F) or an alkyl group containing 1 to 20 carbon atoms and optional heteroatoms which can be N, S (sulfur), or O; or a phosphonate group of the formula: ##STR9## where each J, independently, is O-alkyl, N-alkyl, or alkyl. Each O-alkyl, N-alkyl or alkyl includes 1-20 carbon atoms and, optionally, heteroatoms which can be N, S, or O. T is generally able to form a complex with the catalytic site of a DP IV. ##STR10## and each R1, R2, R3, R4, R5, R6, R7, and R8, separately is a group which does not significantly interfere with site specific recognition of the inhibitory compound by DP IV, and allows a complex to be formed with DP IV. In another aspect, the invention features an inhibitor of DP-IV, having the structure: ##STR11## wherein m is an integer between 0 and 10, inclusive; A and A' are L-amino acid residues such that the A in each repeating bracketed unit can be a different amino acid residue; the C bonded to B is in the L-configuration; the bonds between A and N, A and C, and between A and N are peptide bonds; and each X.sup.1 and X.sup.2 is, independently, a hydroxyl group or a group capable of being hydrolysed to a hydroxyl group at physiological pH.
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Inventor Name | Address | # of filed Patents | Total Citations |
---|---|---|---|
Bachovchin, William W | Melrose, MA | 92 | 965 |
Flentke, George R | Boston, MA | 4 | 173 |
Plaut, Andrew G | Boston, MA | 26 | 649 |
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Fee | Large entity fee | small entity fee | micro entity fee |
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Surcharge after expiration - Late payment is unavoidable | $700.00 | $350.00 | $175.00 |
Surcharge after expiration - Late payment is unintentional | $1,640.00 | $820.00 | $410.00 |
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