Stable no-delivering compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrate esters or chalcogen analogues thereof

Reexamination Certificate

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Reexamination Certificate

active

07745656

ABSTRACT:
Disclosed are novel NO-releasing compounds which comprise a stabilized S-nitrosyl group and a free alcohol or a free thiol group. Also disclosed is a method of preparing the NO-releasing compounds. The method comprises reacting a polythiol or a thioalcohol with a nitrosylating agent. Also disclosed are medical devices coated with the disclosed compounds, methods of delivering NO to treatments sites in a subject by utilizing the medical devices and methods of sterilizing surfaces.

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Askew, S.C., et al., “Catalysis by Cu2+of nitric oxide release from S-nitrosothiols (RSNO),”J.Chem. Soc. Perkin Trans. 2:741-745 (1995).
Batsanov, A.S., et al., “Stereocontrol in cyclisation of dioxolanyl radicals,”J. Chem Soc. Perkin Trans. 1:1281-1294 (1995).
Goldstein, S. and Czapski, G., “Mechanism of the Nitrosation of Thiols and Amines by Oxygenated •NO Solutions: the Nature of the Nitrosating Intermediates,”J. Am. Chem. Soc. 118:3419-3425 (1996).
Gorren, A.C.F., et al., “Decomposition of S-Nitrosoglutathione in the Presence of Copper Ions and Glutathione,”Arch. of Biochem. and Biophys. 330(2):219-228 (1996).
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Vanin, A.F., et al., “Iron Catalyzes both Decomposition and Synthesis of S-Nitrosothiols: Optical and Electron Paramagnetic Resonance Studies,”Nitric Oxide: Biol. and Chem., 1(3):191-203 (1997).
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Bauer, J.A., et al., “Chemical Stabilization of a Vasoactive S-Nitrosothiol with Cyclodextrins Without Loss of Pharmacologic Activity,”Pharmaceutical Research8(10):1329-1333 (1991).
Dicks, A.P., et al., “The reaction of S-nitrosothiols with thiols at high thiol concentrations,”Can. J. Chem. 76:789-794 (1998).
Le, M., et al., “The Decomposition of S-Nitrosated Dithiols: A Model for Vicinal Nitrosothiols in Enzymes,”Bioorganic & Medicinal Chemistry Letters7(11):1393-1398 (1997).
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