N,N'-bis-(pyridoxal)ethylenediamine-N,N'-diacetic acid derivatives

US5130437A · kind A · utility

Assignee

• Salutar, Inc. · US

Inventors

• Scott M. Rocklage · Saratoga, US
• Steven C. Quay · Edmonds, US

Key dates

• Filing date: Sep 6, 1990
• Grant date: Jul 14, 1992
• Expiry date: Sep 6, 2010

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07F13/005
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Manganese(II) chelates of N,N'-bis-(pyridoxal)alkylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal)-1,2-cycloalkylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal)-1,2-arylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal)alkylenediamine-N-acetic acids, N,N'-bis-(pyridoxal)-1,2-cycloalkylenediamine-N-acetic acids, N,N'-(pyridoxal)-1,2-arylenediamine-N-acetic acids, and their salts are highly stable, superior NMRI contrast agents. They maintain the manganese(II) ion in the +2 valence state. Preferred contrast agents are manganese(II) ion chelates of N,N'-bis-(pyridoxal)ethylenediamine-N,N'-diacetic acid, N,N'-bis-(pyridoxal)trans-1,2-cyclohexylenediamine-N,N'-diacetic acid, and the salts and esters thereof. Novel chelate forming compounds are the N,N'-bis-(pyridoxal)-1,2-cycloalkylenediamine-N,N'-diacetic acids and N,N'-bis-(pyridoxal)-1,2-arylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal)alkylenediamine-N-acetic acids, N,N'-bis(pyridoxal)-1,2-cycloalkylenediamine-N-acetic acids, N,N'-bis-(pyridoxal)-1,2-arylenediamine-N-acetic acids, and their salts and esters.