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Claims for Patent: 4,364,921

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Claims for Patent: 4,364,921

Title: Novel triiodinated isophthalic acid diamides as nonionic X-ray contrast media
Abstract:New triiodinated isophthalic acid diamides of the formula ##STR1## wherein the amide residues --CO--N.R.sub.1 R.sub.2 and --CO--N.R.sub.3 R.sub.4 are different from each other and R.sub.1 is hydrogen or C.sub.1-6 alkyl, R.sub.2 is mono- or polyhydroxyalkyl, R.sub.3 is hydrogen or C.sub.1-6 alkyl, R.sub.4 is mono- or polyhydroxylalkyl, R.sub.5 is C.sub.1-6 alkyl or mono- or polyhydroxy-C.sub.1-6 -alkyl or C.sub.1-3 -alkoxy-C.sub.1-3 -alkyl, and R.sub.6 is hydrogen, C.sub.1-6 alkyl or mono- or polyhydroxyalkyl provide superior nonionic X-ray contrast media.
Inventor(s): Speck; Ulrich (Berlin, DE), Blaszkiewicz; Peter (Berlin, DE), Seidelmann; Dieter (Berlin, DE), Klieger; Erich (Berlin, DE)
Assignee: Schering, Aktiengesellschaft (Berlin & Bergkamen, DE)
Application Number:06/127,613
Patent Claims: 1. A triiodinated isophthalic acid diamide of the formula ##STR8## wherein the amide residues --CO--N.R.sub.1 R.sub.2 and --CO--N.R.sub.3 R.sub.4 are different from each other and

R.sub.1 is hydrogen or C.sub.1-6 alkyl,

R.sub.2 is mono- or polyhydroxyalkyl,

R.sub.3 is hydrogen or C.sub.1-6 alkyl,

R.sub.4 is mono- or polyhydroxyalkyl,

R.sub.5 is C.sub.1-6 alkyl or monohydroxy-C.sub.1-6 -alkyl or C.sub.1-3 -alkoxy-C.sub.1-3 -alkyl, and

R.sub.6 is hydrogen or C.sub.1-6 alkyl or mono-.

2. 5-Methoxyacetylamino-2,4,6-triiodoisophthalic acid [(2,3-dihydroxy-N-methylpropyl)-(2,3-dihydroxypropyl)]diamide, a compound of claim 1.

3. 5-(S-2-Hydroxypropionylamino)-2,4,6-triiodoisophthalic acid [(2,3-dihydroxy-N-methylpropyl)-(2,3-dihydroxypropyl)]diamide, a compound of claim 1.

4. 5-Methoxyacetylamino-2,4,6-triiodoisophthalic acid [(2,3-dihydroxy-N-methylpropyl)-(2-hydroxy-1-hydroxymethylethyl)]diamide, a compound of claim 1.

5. The compound of claim 1, wherein at least one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is dihydroxyalkyl.

6. A compound of claim 5, wherein at least one of R.sub.1 or R.sub.2 is dihydroxyalkyl and at least one of R.sub.3 and R.sub.4 is dihydroxyalkyl.

7. A compound of claim 5 or 6 wherein all alkyl moieties in R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have three carbon atoms.

8. A pharmaceutical composition for use as an X-ray contrast agent comprising a radiopaque amount of a compound of Claim 1 and a pharmaceutically acceptable carrier.

9. A method of conducting a radiological examination of a patient which comprises administering to the patient a radiopaque amount of a compound of claim 1.

10. 5-Acetylamino-2,4,6-triiodoisophthalic Acid [(2,3-dihydroxypropyl)-(2,3-dihydroxy-N-methyl-propyl)]diamide.

11. A compound of claim 1 wherein R.sub.5 is methoxymethyl 1-hydroxyethyl or methyl.

12. A compound of claim 1, wherein R.sub.1 and R.sub.3 each are H or CH.sub.3, and R.sub.2 and R.sub.4 each are --CH.sub.2 --CHOH--CH.sub.2 OH or ##STR9##

13. A composition of claim 8 wherein the carrier is pharmaceutically acceptable for angiography.

14. A method of claim 9, wherein the radiological examination is angiography.

15. A compound of claim 11, wherein R.sub.6 is H or C.sub.1-4 -alkyl.
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