3-hydroxy-2(1H)-pyridinone chelating agents
Disclosed is a series of improved metal chelating agents, which are highly effective upon both injection and oral administration; several of the most effective are of low toxicity. These chelating agents incorporate within their structure 1-hydroxy-2-pyridinone (1,2-HOPO) and 3-hydroxy-2-pyridinone (3,2-HOPO) moieties with a substituted carbamoyl group ortho to the hydroxy or oxo groups of the hydroxypyridinone ring. The electron-withdrawing carbamoyl group increases the acidity of the hydroxypyridinones. In the metal complexes of the chelating agents, the amide protons form very strong hydrogen bonds with its adjacent HOPO oxygen donor, making these complexes very stable at physiological conditions. The terminal N-substituents provides a certain degree of lipophilicity to the 3,2-HOPO, increasing oral activity. Also disclosed is a method of making the chelating agents and a method of producing a known compound, 3-hydroxy-1-alkyl-2(1H)pyridinone, used as a precursor to the chelating agent, safely and in large quantities. 2 figs.
- Research Organization:
- Univ. of California (United States)
- DOE Contract Number:
- AC03-76SF00098
- Assignee:
- Univ. of California, Oakland, CA (United States)
- Patent Number(s):
- US 5,624,901/A/
- Application Number:
- PAN: 8-285,640; CNN: Grant AI 11744;Grant DK32999;Grant ES 02698
- OSTI ID:
- 504948
- Resource Relation:
- Other Information: PBD: 29 Apr 1997
- Country of Publication:
- United States
- Language:
- English
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