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US 5,489,692 AGranted
Pyrrolinone-based compounds
AssigneeThe Trustees of the University of Pennsylvania
InventorsRalph Hirschmann, Amos B. Smith, III, Paul Sprengeler, Ryan C. Holcomb, Terence Keenan, John L. Wood, Mark Guzman
Life of this patent
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Abstract
Novel pyrrolinone-based compounds mimic or inhibit the biological and/or chemical activity of peptides, including peptide .beta.-strand conformations. Certain compounds contain functionalized pyrrolinone units in place of one or more amino acids of a target peptide.
Claims13
A compound having structure:
- ##STR14## wherein:
- R.sub.A1 is H, a C-terminal amino acid, a C-terminal peptide, an amine protecting group, an amide protecting group, a group that improves the pharmacokinetic properties of the compound, or a group that improves the pharmacodynamic properties of the compound;
- R.sub.B1 is OR.sub.D, NR.sub.D R.sub.D, a N-terminal amino acid, a N-terminal peptide, a carboxyl protecting group, a group that improves the pharmacokinetic properties of the compound, or a group that improves the pharmacodynamic properties of the compound;
- each R.sub.C is, independently, an amino acid side chain;
- R.sub.D is H, an amine protecting group, or alkyl having 1 to about 7 carbon atoms;
- R.sub.E is H or an amine protecting group, or R.sub.A1 and R.sub.E, together are a group that improves the pharmacokinetic properties of the compound or a group that improves the pharmacodynamic properties of the compound;
- each Q is, independently, OH or .dbd.O;
- x is 0 or 1;
- and
- n is 1-200.
7 more elements
A compound having structure:
- ##STR15## wherein:
- each R.sub.C is, independently, an amino acid side chain;
- R.sub.D is H, an amine protecting group, or alkyl having 1 to about 7 carbon atoms;
- R.sub.NP is H or an amine protecting group;
- R.sub.AP is H or a carboxyl protecting group;
- and
- y and z are, independently, 1-200.
4 more elements
A compound having structure:
- ##STR16## wherein:
- each R.sub.C is, independently, an amino acid side chain;
- R.sub.D is H, an amine protecting group, or alkyl having 1 to about 7 carbon atoms;
- R.sub.NP is H or an amine protecting group;
- R.sub.AP is H or a carboxyl protecting group;
- and
- y is 2-200.
4 more elements
A compound having structure:
- ##STR17## wherein:
- each R.sub.C is, independently, an amino acid side chain;
- R.sub.D is H, an amine protecting group, or alkyl having 1 to about 7 carbon atoms;
- R.sub.NP is H or an amine protecting group;
- R.sub.AP is H or a carboxyl protecting group;
- and
- z is 2-200.
4 more elements
A process for preparing a compound having structure:
- ##STR18## comprising the steps of:
- providing a first synthon having structure:
- ##STR19## contacting said first synthon with a second synthon having structure:
- ##STR20## for a time and under reaction conditions effective to form said compound;
- wherein:
- each R.sub.C is, independently, an amino acid side chain;
- R.sub.D is H, an amine protecting group, or alkyl having 1 to about 7 carbon atoms;
- R.sub.NP is H or an amine protecting group;
- R.sub.AP is H or a carboxyl protecting group;
- and
- y and z are, independently, 0-200.
8 more elements
Dependencies are inferred from the claim text.