Dipyridoxyl phosphate chelating compound intermediates useful as

Details Dipyridoxyl phosphate chelating compound intermediates useful as Dipyridoxyl phosphate chelating compound intermediates useful as

1990-08-20

1993-06-29

Rotman, Alan L.

Drug, bio-affecting and body treating compositions

In vivo diagnosis or in vivo testing

Magnetic imaging agent

546 5, 546 6, 546 22, 546 24, 546261, A61K 4904, C07F 958, C07F 102, C07F 1300

Patent

active

052232433

ABSTRACT:
N,N'-bis-(pyridoxal-5-phosphate)-alkylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal-5-phosphate)-1,2-cycloalkylenediamine-N,N'diacetic acids, and N,N'-bis-(pyridoxal-5-phosphate)-1,2-arylenediamine-N,N'diacetic acids, the corresponding monophosphate compounds and monoacetic acid compounds, and their salts and esters form stable, highly soluble chelates with paramagnetic metal ions, and are highly effective NMRI contrast agents. Preferred contrast agents are paramagnetic ion chelates of N,N'-bis-(pyridoxal-5-phosphate)ethylenediamine-N,N'-diacetic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-cyclohexylenediamine-N,N'-diacet ic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-arylenediamine-N,N'-diacetic acid, and the soluble calcium salts thereof.
Novel intermediates for forming these compounds are N,N'-bis(pyridoxal-5-phosphate)alkylenediimines, N,N'-bis(pyridoxal-5-phosphate)alkylenediamines, N,N'-bis(pyridoxal-5-phosphate)-1,2-cycloalkylenediimines, N,N'-bis(pyridoxal-5-phosphate)-1,2-cycloalkylenediamines, N,N'-bis(pyridoxal-5-phosphate)-1,2-arylenediamines, and the corresponding monophosphate compounds.

REFERENCES:
patent: 4992555 (1991-02-01), Rocklage et al.
patent: 5091169 (1992-02-01), Rocklage et al.
patent: 5130431 (1992-07-01), Rocklage et al.
patent: 5130437 (1992-07-01), Rocklage et al.
Bowers-Komro and McCormick, "Single- and Double-Headed Analogs of Pyridoxamine 5'-Phosphate as Probes for Pyridoxamine 5'-Phosphate Utilizing Enzymes", Bioorganic Chemistry 15, (1987), pp. 224-236.

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