iotroxic acid

Originator

Biliscopin,Schering,W. Germany,1978

The Uses of iotroxic acid

Diagnostic aid (radiopaque medium).

Definition

ChEBI: Iotroxic acid is an organic molecular entity.

Manufacturing Process

(a) Condensation in dimethylacetamide: To a suspension of 51.5 g of anhydrous 3-amino-2,4,6-triiodo-benzoic acid (0.1 mol) in 100 ml of dimethylacetamide were slowly added dropwise, while stirring, 15.5 g of 3,6,9-trioxaundecanediacid dichloride (0.06 mol), during which the temperature gradually rose to about 50°C and the whole passed into solution. After being stirred overnight, the solution was added dropwise to 1 liter of a 0.28 N solution of sodium hydroxide, and then 200 ml of 2 N hydrochloric acid were cautiously added. The precipitate was filtered off with suction, washed with water and dried. The yield was practically quantitative.
(b) Condensation in dioxan: 15.5 g of 3,6,9-trioxaundecane diacid dichloride were added dropwise at about 95°C to a solution of 51.5 g of anhydrous 3- amino-2,4,6-triiodo-benzoic acid in 52 ml of anhydrous dioxan. After further stirring and heating for 3 hours, the solution was cooled, stirred dropwise into 500 ml of a 0.4 N solution of sodium hydroxide, and further worked up as described in paragraph (a). The yield was practically quantitative.
(c) Purification: To the crude product obtained as described under paragraph (a) or (b) in 300 ml of methanol was slowly added a quantity (about 15 ml) of a 12 N solution of sodium hydroxide such that a test portion diluted with water had a pH-value of 8 to 9. After stirring the mixture overnight, the sodium salt of 3,6,9-trioxaundecane-1,11-dioyl-bis-(3-carboxy-2,4,6-triodoanilide) which crystallized out was filtered off with suction, was hed with methanol and dried. Yield: 92 g (90% of the theoretical yield).
A solution of the salt in 900 ml of water was treated with active carbon, and concentrated hydrochloric acid was added until the pH-value was 1. The precipitate was filtered off with suction, washed with water, and dried at 50°C.
The yield of pure 3,6,9-trioxaundecane-1,11-dioyl-bis-(3-carboxy-2,4,6- triiodo-anilide) was 80 g (80% of the theoretical yield). The substance melted at 175°C with sintering.

Therapeutic Function

Diagnostic aid (radiopaque medium)

Flammability and Explosibility

Not classified