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Details for Patent: 5,695,739

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Details for Patent: 5,695,739

Title: Derivatized DTPA complexes, pharmaceutical agents containing these compounds, their use, and processes for their production
Abstract:Compounds of a general Formula I ##STR1## wherein Z.sup.1 and Z.sup.2 in each case independently mean the residue wherein m and n means the numbers 0-20, k, l, q and r means the numbers 0 and 1, and R means a hydrogen atom, an optionally OR.sup.1 -substituted C.sub.1 -C.sub.6 -alkyl residue, or a CH.sub.2 COOR.sup.1 group with R.sup.1 meaning a hydrogen atom, a C.sub.1 -C.sub.6 -alkyl residue, or a benzyl group, X means a hydrogen atom and/or a metal ion equivalent of an element of atomic number 21-29, 42, 44 or 57-83, with the provisos that at least two the substituents X stand for a metal ion equivalent; that one of the substituents Z.sup.1 and Z.sup.2 stands for a hydrogen and the other is not H; that--if n and 1 each mean the number 0--k and r do not simultaneously mean the number 1; that --(O).sub.r --R is not --OH; and that Z.sup.1 and Z.sup.2 are not --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --COOCH.sub.2 C.sub.6 H.sub.5 or --CH.sub.2 --C.sub.6 H.sub.4 --O--(CH.sub.2).sub.5 --COOCH.sub.2 C.sub.6 H.sub.5, as well as their salts with inorganic and/or organic bases, amino acids or amino acid amides, are valuable pharmaceutical agents, e.g., for NMR or X-ray imaging.
Inventor(s): Schmitt-Willich; Heribert (Berlin, DE), Platzek; Johannes (Berlin, DE), Gries; Heinz (Berlin, DE), Schumann-Giampieri; Gabrielle (Berlin, DE), Weinmann; Hanns-Joachim (Berlin, DE), Vogler; Hubert (Berlin, DE), Deutsch; Julius (Berlin, DE), Conrad; Jurgen (Berlin, DE)
Assignee: Schering Aktiengesellschaft (Berlin, DE)
Filing Date:Nov 30, 1994
Application Number:08/351,126
Claims:1. A method of enhancing an X-ray image comprising administering to a patient a compound of the formula ##STR4## wherein one of Z.sup.1 and Z.sup.2 is H and the other is --(CH.sub.2).sub.m --(C.sub.6 H.sub.4).sub.q --(O).sub.k --(CH.sub.2).sub.n --(C.sub.6 H.sub.4).sub.l --(O).sub.r --R,

wherein

m and n independently are 0-20,

k, l, q and r each independently is 0 or 1,

R is hydrogen, optionally OR.sup.1 -substituted C.sub.1 -C.sub.6 -alkyl or CH.sub.2 COOR.sup.1,

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

X is, in each case, a hydrogen atom or a metal ion equivalent of an element of atomic number 21-29, 42, 44 or 57-83;

with the provisos that at least two X groups represent a metal ion equivalent of atomic number 21-29, 42, 44 or 57-83; that when n and l each are 0, then k and r are not each simultaneously 1; that --(O).sub.r -R is not --OH; that Z.sup.1 and Z.sup.2 are not --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --COOCH.sub.2 C.sub.6 H.sub.5, or --CH.sub.2 --C.sub.6 H.sub.4 --O--(CH.sub.2).sub.5 --COOCH.sub.2 C.sub.6 H.sub.5 and that at least one of q or l is 1;

or a physiologically acceptable salt thereof with an inorganic and/or organic base, an amino acid or an amino acid amide.

2. A method of claim 1, wherein the hepatobiliary system is imaged.

3. A method of claim 1, wherein the renal system is imaged.

4. A method of claim 1, wherein Z.sup.1 is hydrogen and Z.sup.2 is --(CH.sub.2).sub.m --(C.sub.6 H.sub.4).sub.q --(O).sub.k --(CH.sub.2).sub.n --(C.sub.6 H.sub.4).sub.l --(O).sub.r --R.

5. A method of claim 1, wherein Z.sup.2 is hydrogen and Z.sup.1 is --(CH.sub.2).sub.m --(C.sub.6 H.sub.4).sub.q --(O).sub.k --(CH.sub.2).sub.n --(C.sub.6 H.sub.4).sub.l --(O).sub.r --R.

6. A method of claim 1, wherein Z.sup.1 is --CH.sub.2 --C.sub.6 H.sub.4 --OCH.sub.3, --CH.sub.2 --C.sub.6 H.sub.5, --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --C.sub.6 H.sub.4 --OCH.sub.3, --CH.sub.2 --O--CH.sub.2 --C.sub.6 H.sub.5, --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --COOH, --CH.sub.2 --C.sub.6 H.sub.4 --OC.sub.2 H.sub.5, --CH.sub.2 --C.sub.6 H.sub.4 --OC.sub.4 H.sub.9 or --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --C.sub.6 H.sub.5.

7. A method of claim 1, wherein Z.sup.2 is --CH.sub.2 --C.sub.6 H.sub.4 --OCH.sub.3, --CH.sub.2 --C.sub.6 H.sub.5, --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --C.sub.6 H.sub.4 --OCH.sub.3, --CH.sub.2 --O--CH.sub.2 --C.sub.6 H.sub.5, --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --COOH, --CH.sub.2 --C.sub.6 H.sub.4 --OC.sub.2 H.sub.5, --CH.sub.2 --C.sub.6 H.sub.4 --OC.sub.4 H.sub.9 or --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --C.sub.6 H.sub.5.

8. A method of claim 1, wherein at least three X groups represent a Gd ion.

9. A method of claim 6, wherein at least three X groups represent a Gd ion.

10. A method of claim 7, wherein at least three X groups represent a Gd ion.

11. A method of claim 1, wherein said compound is:

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-methoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

europium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-methoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

iron(III) complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-methoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

bismuth complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-methoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-5-(4-methoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-[4-(4-methoxybenzyloxy)benzyl]und ecanedioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-benzylundecanedioic acid or a physiologically acceptable salt thereof;

ytterbium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-benzylundecanedioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-benzyloxymethylundecanedioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-carboxymethoxybenzyl)undecaned ioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-ethoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

europium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-ethoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

iron complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-ethoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-butoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

europium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-butoxybenzyl)undecanedioic acid or a physiologically salt thereof;

iron complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-butoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-benzyloxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

europium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-benzyloxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof; or

iron complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-benzyloxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof.

12. A method of claim 1, wherein at least one of k and r is 1.

13. A method of claim 12, wherein Z.sup.1 is CH.sub.2 --C.sub.6 H.sub.4 --OCH.sub.3, --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --C.sub.6 H.sub.4 --OCH.sub.3, --CH.sub.2 --O--CH.sub.2 --C.sub.6 H.sub.5, --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --COOH, --CH.sub.2 --C.sub.6 H.sub.4 --OC.sub.2 H.sub.5, --CH.sub.2 --C.sub.6 H.sub.4 --OC.sub.4 H.sub.9 or --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --C.sub.6 H.sub.5.

14. A method of claim 12, wherein Z.sup.2 is CH.sub.2 --C.sub.6 H.sub.4 --OCH.sub.3, --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --C.sub.6 H.sub.4 --OCH.sub.3, --CH.sub.2 --O--CH.sub.2 --C.sub.6 H.sub.5, --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --COOH, --CH.sub.2 --C.sub.6 H.sub.4 --OC.sub.2 H.sub.5, --CH.sub.2 --C.sub.6 H.sub.4 --OC.sub.4 H.sub.9 or --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --C.sub.6 H.sub.5.

15. A method of claim 12, wherein said compound is:

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-methoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

europium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-methoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

iron(III) complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-methoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

bismuth complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-methoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-5-(4-methoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-[4-(4-methoxybenzyloxy)benzyl]und ecanedioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-benzylundecanedioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-carboxymethoxybenzyl)undecaned ioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-ethoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

europium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-ethoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

iron complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-ethoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-butoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

europium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-butoxybenzyl)undecanedioic acid or a physiologically salt thereof;

iron complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-butoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-benzyloxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof;

europium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-benzyloxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof; or

iron complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-benzyloxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof.

16. A method of claim 1, wherein said compound is administered intravenously.

17. A method of claim 1, wherein said compound is:

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-ethoxybenzyl)undecanedioic acid or a physiologically acceptable salt thereof; or

gadolinium complex of 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-ethoxyphenylethyl)undecanedioi c acid or a physiologically acceptable salt thereof.

18. A method according to claim 1, wherein said compound is administered in a pharmaceutical composition comprising said compound and a pharmaceutically acceptable carrier.

19. A method according to claim 1, wherein R.sup.1 is H or C.sub.1 -C.sub.6 -alkyl.

20. A method according to claim 1, wherein said compound is administered in a dose of 1 .mu.mole/kg-5 mmole/kg.
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