Synthesis of labeled metabolites

US6709645B1 · kind B1 · utility

Assignee

• The Regents of the University of California · US

Inventors

• Rodolfo A. Martinez · Santa Fe, US
• Louis A. Silks · Los Alamos, US
• Clifford J. Unkefer · Los Alamos, US
• Robert W. Atcher · Kensington, US

Key dates

• Filing date: Apr 18, 2003
• Grant date: Mar 23, 2004
• Expiry date: Apr 18, 2023

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07B2200/05
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present invention is directed to labeled compounds, for example, isotopically enriched mustard gas metabolites including: [1,1′,2,2′-13C4]ethane, 1,1′-sulfonylbis[2-(methylthio); [1,1′,2,2′-13C4]ethane, 1-[[2-(methylsulfinyl)ethyl]sulfonyl]-2-(methylthio); [1,1′,2,2′-13C4]ethane, 1,1′-sulfonylbis[2-(methylsulfinyl)]; and, 2,2′-sulfinylbis([1,2-13C2]ethanol of the general formula where Q1 is selected from the group consisting of sulfide (—S—), sulfone (—S(O)—), sulfoxide (—S(O2)—) and oxide (—O—), at least one C* is 13C, X is selected from the group consisting of hydrogen and deuterium, and Z is selected from the group consisting of hydroxide (—OH), and —Q2—R where Q2 is selected from the group consisting of sulfide (—S—), sulfone(—S(O)—), sulfoxide (—S(O2)—) and oxide (—O—), and R is selected from the group consisting of hydrogen, a C1 to C4 lower alkyl, and amino acid moieties, with the proviso that when Z is a hydroxide and Q1 is a sulfide, then at least one X is deuterium.