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US 6,586,426 B1Granted
β-sheet mimetics and use thereof as protease inhibitors
AssigneeMolecumetics, Ltd.
InventorMichael Kahn
Life of this patent
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Abstract
There are disclosed β-sheet mimetics and methods relating to the same for imparting or stabilizing the β-sheet structure of a peptide, protein or molecule. In one aspect, the β-sheet mimetics are covalently attached at the end or within the length of the peptide or protein. The β-sheet mimetics have utility as protease inhibitors generally, including activity as serine protease inhibitors such as thrombin, elastase and Factor X.
Claims15
A bicyclic ring compound having the structure:
- wherein
- R1, R2 and R3 are independently selected from amino acid side chain moieties and derivatives thereof;
- A is —C(═O)—, —(CH2)1-4—, —C(═O)(CH2)1-3—, —(CH2)1-2O— or —(CH2)1-2S—;
- B is CH;
- C is —C(═O)—, —(CH2)1-3—, —O—, —S—, —O—(CH2)1-2— or —S(CH2)1-2—;
- Y and Z represent the remainder of the molecule;
- and
- any two adjacent CH groups of the bicyclic ring may form a double bond;
- with the provisos that (i) R1 is not hydrogen, (ii) when R1 is benzyl, R2 and R3 are both hydrogen, and A is —CH2CH2—, then C is not —CH2—, (iii) when R1 is methyl, R2 and R3 are both hydrogen, and A is —CH2O—, then C is not —CH2—, and (iv) when R1 is benzyl, R2 and R3 are both hydrogen, and A is —CH2—, then C is not —S—.
6 more elements
Dependencies are inferred from the claim text.