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|Title:||1,4,7,10-Tetraazacyclododecane butyltriols, processes for their production and pharmaceutical agents containing them|
|Abstract:||1,4,7,10-Tetraazacyclodedecane butyltriols of general formula I.sub.A ##STR1## in which R.sup.1 means hydrogen or a metal ion equivalent independent of one another and R.sup.2 means a butyltriol radical as well as their salts with organic or inorganic bases or amino acids are valuable pharmaceutical agents.|
|Inventor(s):||Platzek; Johannes (Berlin, DE), Gries; Heinz (Berlin, DE), Weinmann; Hanns-Joachim (Berlin, DE), Schuhmann-Giampieri; Gabriele (Berlin, DE), Press; Wolf-Rudiger (Berlin, DE)|
|Assignee:||Schering Aktiengesellschaft (Berlin, DE)|
|Filing Date:||Jul 23, 1999|
|Claims:||1. A 1,4,7,10-tetraazacyclododecane butyltriol of formula I.sub.A ##STR8## |
each R.sup.1 is hydrogen or a metal ion equivalent, independent of one another and
R.sup.2 is butyltriol
or a salt thereof with an organic or inorganic base or an amino acid.
2. A compound according to claim 1, wherein all R.sup.1 's are hydrogen atoms.
3. A compound according to claim 1, wherein at least two of substituents R.sup.1 are metal ion equivalents of at least one element of the atomic numbers 21-29, 42, 44 or 57-83 or at least one radionuclide of an element of the atomic numbers 27, 29, 31, 32, 37-39, 43, 49, 62, 64, 70 or 77.
4. 10-(2,3,4-trihydroxybutyl)-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclod odecane, a compound of claim 1.
5. The gadolinium complex of 10-(2,3,4-trihydroxybutyl)-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclod odecane.
6. A compound of claim 1, wherein R.sup.2 is 2,3,4-trihydroxybutyl.
7. A compound of claim 3, wherein R.sup.2 is 2,3,4-trihydroxybutyl.
8. A compound of claim 7, wherein said metal ion equivalents are of at least one element of atomic numbers 21-29, 42, 44 or 58-70.
9. A pharmaceutical composition comprising a compound of claim 3 and a pharmaceutically acceptable carrier.
10. A method of conducting NMR, X-ray, ultrasound or radioimaging or radiotherapy comprising administering a composition of claim 9 effective therefor.
11. A process for the production of a 1,4,7,10-tetraazacyclododecane butyltriol of claim 1 comprising reacting a compound of formula II ##STR9##
X stands for a nitrogen protecting group or CH.sub.2 COOY group with Y meaning hydrogen, an ammonium cation, an alkali metal or a protecting group,
with a substrate introducing the radical R.sup.2 in protected form,
and wherein the optionally contained nitrogen protecting groups X are removed and the --NH-- groups thus released are alkylated with an acetic acid derivative of general formula III
in which Hal stands for chlorine, bromine or iodine,
the (hydroxy and optionally acid) protecting groups are removed and the resulting compounds of general formula I.sub.A with R.sup.1 meaning hydrogen with a metal oxide or metal salt are converted into the metal complexes of general formula I.sub.A with R.sup.1 meaning a metal ion equivalent and then, optionally, still existing acidic hydrogen atoms are substituted by cations of inorganic and/or organic bases, amino acids or amino acid amides.
12. A pharmaceutical composition comprising a compound of claim 5 and a pharmaceutically acceptable carrier.
13. A method of conducting NMR, X-ray, ultrasound or radioimaging or radiotherapy comprising administering a composition of claim 12 effective therefor.
14. The gadolinium complex of 10-[2-hydroxy-2,2-bis(hydroxymethyl)ethyl]-1,4,7-triscarboxymethyl-1,4,7,1 0-tetraazacyclododecane or 10-[1,1,1-tris(hydroxymethyl)methyl]-1,4,7-triscarboxymethyl-1,4,7,10-tetr aazacyclododecane, each a compound of claim 1.
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