Cysteine proteinase inhibitors and inhibitor precursors
US5317086A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Mar 9, 1992 |
| Grant date | May 31, 1994 |
| Priority date | — |
| Expiry date | Mar 9, 2012 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C323/41
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Compounds are provided that are useful in inhibiting cysteine or serine proteinases. The compounds define a peptide backbone with a sulfur atom substituted in the backbone. A leaving group is associated, or bonded, to a carbon atom adjacent to the sulfur atom. The leaving group is displaceable either by hydrolysis under physiological conditions (with the hydrolyzed compound forming an aldehyde enzyme inhibitor) or by an active-site nucleophile of a cysteine or serine proteinase. When the leaving group is displaced by hydrolysis, then the compound functions as a protected derivative of the aldehyde functional group and is stabilized against oxidation or degradation, yet allows for release of the aldehyde moiety at the pharmacological site of action. The peptide sulfide analogues bearing a leaving group displaced by the active-site nucleophile covalently bond cysteine or serine proteinases and thus irreversibly inhibit these enzymes.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.