Psoralen sensitizers for viral inactivation

Details Psoralen sensitizers for viral inactivation Psoralen sensitizers for viral inactivation

1997-11-21

1999-07-06

Fan, Jane

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549282, 548526, C07D40512

Patent

active

059199350

ABSTRACT:
The present invention relates to novel, halogenated psoralen compounds that are useful for inactivating vital contaminants in blood-derived products, particularly blood-derived products that contain platelets or red blood cells. The psoralen compounds of the present invention have the following formula: The side chain S which is a attached to the carbon at position 8 of the psoralen moiety contains a quartemary ammonium group which comprises a central nitrogen atom, a linking group L, and an aromatic ring structure. The linking group L joins the central nitrogen atom of the quartenary ammonium group to the psoralen moiety. The linking group L comprises a carbon chain having 2 to 12 carbon atoms and an oxygen atom which links the carbon chain to the psoralen moiety. The psoralen compounds of the present invention also comprise one or more halogens attached to the psoralen moiety. Preferably the halogens are attached to the carbon atom at position 3 or 5 of the psoralen moiety. In one class of these novel psoralen compounds, the central nitrogen atom of the quartenary ammonium group is a component of the aromatic ring structure. In another class, the central nitrogen atom is attached to three substituent groups, R.sup.1, R.sup.2, and R.sup.3 wherein R.sup.3 has the following structure: --R.sup.5 --CH.dbd.CH--R.sup.6 wherein R.sup.5 is a carbon chain comprising 1 to 3 carbon atoms, and wherein R.sup.6 is the aromatic ring, The present invention also relates to methods of making and using the novel psoralen compounds.

REFERENCES:
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patent: 5418130 (1995-05-01), Platz et al.
patent: 5587490 (1996-12-01), Goodrich et al.
"The design and development of selective photoactivated drugs for sterilization of blood products", by Goodrich, et al., Drugs of the Future, 1997, 22(2), pp. 159-171.
"Electron Transfer Chemistry of Psoralen and Coumarin Derivatives by Means of Radiolytic and Electrochemical Experiments", by Chen, et al., J. Phys. Chem. A., vol. 101, No. 11, 1997, pp. 2124-2130.
"New Psoralen Derivatives for Selective Viral Inactivation in Platelet Concentrates", by Platz, et al., The Spectrum, Fall 1995, vol. 8, Issue 3, pp. 11-20.
"Synthesis, Evaluation and Mechanistic Studies of Halogenated Psoralen and Acridine Photosensitizers: A Dissertation", by Tongqian Chen, 1995.

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