3-hydroxy-2(1H)-pyridinone chelating agents

Details 3-hydroxy-2(1H)-pyridinone chelating agents 3-hydroxy-2(1H)-pyridinone chelating agents

1997-04-22

1999-04-06

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

546 6, 546256, 5462681, 546296, C07D40112, C07D40512, C07D40312

Patent

active

058920293

ABSTRACT:
Disclosed is a series of improved chelating agents and the chelates formed from these 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 3-hydroxy-2-pyridinone (3,2-HOPO) moieties with a substituted carbamoyl group ortho to the hydroxy group of the hydroxypyridinone ring. The electron-withdrawing carbamoyl group increases the acidity, as well as the chemical stability towards oxidation and reduction, of the hydroxypyridinones. In the metal complexes of the chelating agents, the amide protons form very strong hydrogen bonds with the adjacent HOPO oxygen donor, making these complexes very stable at physiological conditions. The terminal N-substituents provide a certain degree of lipophilicity to the 3,2-HOPO, increasing oral activity.

REFERENCES:
patent: 4698431 (1987-10-01), Raymond et al.
patent: 5624901 (1997-04-01), Raymond et al.

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