Fluorine-containing macrocyclic metal complexes
AssigneeSchering Corporation
InventorsJohannes Platzek, Bernd Raduchel, Ulrich Niedballa, Hanns-Joachim Weinmann, Hans Bauer, Klaus Roth
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Abstract
The invention relates to new fluorine-containing macrocyclic metal complexes that consist of a complexing agent of formula I and at least one metal ion of an element of atomic numbers 21-29, 42, 44 or 57-83 ##STR1## in which n, R.sup.1, R.sup.2, R.sup.3 and A have a different meaning, agents containing these compounds, their use as NMR and x-ray diagnostic agents as well as process for the production of these compounds and agents.
Claims15
A fluorine-containing macrocyclic metal complex having at least one metal ion of an element of atomic numbers 21-29, 42, 44 or 57-83 and a complexing agent of formula I ##STR6## in which:
- n and m independently of one another, stand for the numbers 0 or 1;
- R.sup.1 independently of one another, stand for a hydrogen atom or a metal ion equivalent;
- R.sup.3 stands for a hydrogen atom, a straight-chain or branched C.sub.1 -C.sub.10 alkyl group, which optionally is substituted by 1-5 C.sub.1 -C.sub.6 alkoxy groups, hydroxy-C.sub.1 -C.sub.6 alkyl groups and/or hydroxy groups;
- R.sup.2 stands for a straight-chain or branched C.sub.1 -C.sub.10 alkylene group which is substituted by 1 to 3 --CF.sub.3 groups and which optionally is interrupted by 1 to 5 oxygen atoms and/or carbonyl groups and/or optionally is substituted by 1 to 5 hydroxy groups, C.sub.1 -C.sub.6 alkoxy-C.sub.1 -C.sub.6 alkyl groups, --OR.sup.4, --CO--NR.sup.5 R.sup.6, NR.sup.5 R.sup.6 and/or --NR.sup.5 --CO--R.sup.6 radicals,
- in which R.sup.4 stands for a straight-chain or branched C.sub.1 -C.sub.4 alkyl radical and R.sup.5, R.sup.6, independently of one another, have the meaning of R.sup.3 ;
- and
- A stands for a fluorine atom when m is 1 or A stands for a hydrogen atom or a second macrocyclic radical of formula II, ##STR7## in which:
- n, R.sup.1 and R.sup.3 have the indicated meanings, when m is 0;
- and
- salts thereof with inorganic and/or organic bases or amino acids;
- and C.sub.1 -C.sub.6 alkyl or C.sub.6 -C.sub.10 aryl or aralkyl esters or amides thereof;
- provided that at least two radicals R.sup.1 stand for a metal ion equivalent.
A process for the production of a fluorine-containing macrocyclic metal complex having at least one metal ion of an element of atomic numbers 21-29, 42, 44 or 57-83 and a complexing agent of formula I ##STR8## in which:
- n and m, independently of one another, stand for the numbers 0 or 1;
- R.sup.1 independently of one another, stand for a hydrogen atom or a metal ion equivalent;
- p1 R.sup.3 stands for a hydrogen atom, a straight-chain or branched C.sub.1 -C.sub.10 alkyl group, which optionally is substituted by 1-5 C.sub.1 -C.sub.6 alkoxy groups, hydroxy-C.sub.1 -C.sub.6 alkyl groups and/or hydroxy groups;
- p1 R.sup.2 stands for a straight-chain or branched C.sub.1 -C.sub.10 alkylene group which is substituted by 1 to 3 --CF.sub.3 groups and which optionally is interrupted by 1 to 5 oxygen atoms and/or carbonyl groups and/or optionally is substituted by 1 to 5 hydroxy groups, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl groups, --OR.sup.4, --CO--NR.sup.5 R.sup.6, --NR.sup.5 R.sup.6 and/or --NR.sup.5 --CO--R.sup.6 radicals,
- in which R.sup.4 stands for a straight-chain or branched C.sub.1 -C.sub.4 alkyl radical and R.sup.5, R.sup.6, independently of one another, have the meaning of R.sup.3 ;
- and
- A stands for a fluorine atom wherein m is 1 or A stands for a hydrogen atom or a second macrocyclic radical of formula II, ##STR9## in which n, R.sup.1 and R.sup.3 have the indicated meanings, wherein m is 0;
- and
- salts thereof with inorganic and/or organic bases or amino acids;
- and C.sub.1 -C.sub.6 alkyl or C.sub.6 -C.sub.10 aryl or aralkyl esters or amides thereof;
- provided that at least two radicals R.sup.1 stand for a metal ion equivalent;
- which process comprises reacting a complexing agent of formula IV ##STR10## in which n, m, R.sup.2 and R.sup.3 have the indicated meaning and A' stands for a fluorine atom when m is 1, or A' stands for a hydrogen atom or a second macrocyclic radical of formula V, ##STR11## when m is 0;
- with a metal salt or metal oxide of an element of atomic numbers 21-29, 42, 44 or 57-83 to produce the desired metal complexes.
Dependencies are inferred from the claim text.