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EP0130934B1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Complexing agents, complexes and complex salts

Assignee: Bayer Pharma AG
•
Filing: 1984-06-28
•
Granted: 1987-08-05
•
Expires: 2004-06-28
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Abstract

Abstract 1. Compounds of the general formula I see diagramm : EP0130934,P14,F1 where R**1 represents a COOX group or the group see diagramm : EP0130934,P14,F2 R**2 and R**3 are the same or different and represent a hydrogen atom, a lower straight or branched chain hydrocarbon group, a phenyl or a benzyl group, or R**2 and R**3 together represent a trimethylene or tetramethylene group, R**4 represents a straight or branched chain mono- or polyhydroxyalkyl group, R**5 represents a hydrogen atom, a lower straight or branched chain optionally mono- or polyhydroxylated hydrocarbon group, Q represents the group -N-(CH2 )j -R**x , where j is a number 1 to 4 and R**x represents a COOX group or, when j > 1, the group see diagramm : EP0130934,P14,F3 where k and m are the same or different and represent the numbers 0 or 2, I represents the numbers 1 or 2 and n and w are the same or different and represent the numbers 0 or 1, where n and w only represent the number 1 when k and m represent the number 2, and X represents hydrogen and/or metal ion equivalents, as well as their salts with physiologically acceptable bases.

Inventors

  • 👤 Heinz Dr. Gries
  • 👤 Franz-Josef Dr. Renneke
  • 👤 Hanns-Joachim Dr. Weinmann

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-23 20:10
CPC Classifications
A; A61; A61K; A61K49/00; A61K49/06; A61K49/18; A61K49/1806; A61K49/1812; A61K49/0002; A61K51/00; A61K51/02; A61K51/04; A61K51/0474; A61K51/0478; A61K51/048; A61P; A61P39/00; A61P39/02; A61K2123/00; Y; Y10; Y10T; Y10T436/00; Y10T436/24

Claims Analysis

Total Claims: 42
Claim 1
Independent Claim 191 words
Compounds of the general formula I where R 1 represents a COOX group or the group R 2 and R 3 are the same or different and represent a hydrogen atom, a lower straight or branched chain hydrocarbon group, a phenyl or a benzyl group, or R 2 and R 3 together represent a trimethylene or tetramethylene group, R 4 represents a straight or branched chain mono- or polyhydroxyalkyl group, R 5 represents a hydrogen atom, a lower straight or branched chain optionally mono- or polyhydroxylated hydrocarbon group, Q represents the group -N-(CH 2 )j-R x , where j is a number 1 to 4 and R" represents a COOX group or, when j > 1, the group where k and m are the same or different and represent the numbers 0 or 2, I represents the numbers 1 or 2 and n and w are the same or different and represent the numbers 0 or 1, where n and w only represent the number 1 when k and m represent the number 2, and X represents hydrogen and/or metal ion equivalents, as well as their salts with physiologically acceptable bases.
Claim 2
Dependent Claim 191 words
Compounds of the general formula I where R 1 represents a COOX group or the group R 2 and R 3 are the same or different and represent a hydrogen atom, a lower straight or branched chain hydrocarbon group, a phenyl or a benzyl group, or R 2 and R 3 together represent a trimethylene or tetramethylene group, R 4 represents a straight or branched chain mono- or polyhydroxyalkyl group, R 5 represents a hydrogen atom, a lower straight or branched chain optionally mono- or polyhydroxylated hydrocarbon group, Q represents the group -N-(CH 2 )j-R x , where j is a number 1 to 4 and R" represents a COOX group or, when j > 1, the group where k and m are the same or different and represent the numbers 0 or 2, I represents the numbers 1 or 2 and n and w are the same or different and represent the numbers 0 or 1, where n and w only represent the number 1 when k and m represent the number 2, and X represents hydrogen and/or metal ion equivalents, as well as their salts with physiologically acceptable bases.
Claim 3
Dependent Claim 59 words
Compound of the general formula la wherein X, R 1 , R Z , R 3 , R 4 and R 5 have the meanings given in claim 1 and y represents 0 or, in the case that R 2 and R 3 are hydrogen atoms, also 1 or 2 as well as their salts with physiologically acceptable bases.
Claim 4
Dependent Claim 19 words
Compounds of general formula I and la according to claims 1 and 2, characterised in that X represents hydrogen.
Claim 5
Dependent Claim 63 words
N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3,4-trihydroxybutyl-carbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3--dihydroxypropyl-carbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl--N 3 ,N 9- bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis[2-hydroxy-1-(hydroxymethyl)-ethylcarbamoylmethyll-3,6,9-triazaundecane dicarboxylic acid, N 6- carboxymethyl-N 3 ,N 9- bis[bis(2-hydroxyethyl)-carbamoylmethyl]-3,6,9--triazaundecane dicarboxylic acid, N 6- carboxymethyl-N 3 ,N 9 -bis(2,3,4,5,6-pentahydroxyhexyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis[2,3-dihydroxypropyl-1-(hydroxymethyl)carbamoylmethyl]--3,6,9-triazaundecane dicarboxylic acid.
Claim 6
Dependent Claim 63 words
N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3,4-trihydroxybutyl-carbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3--dihydroxypropyl-carbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl--N 3 ,N 9- bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis[2-hydroxy-1-(hydroxymethyl)-ethylcarbamoylmethyll-3,6,9-triazaundecane dicarboxylic acid, N 6- carboxymethyl-N 3 ,N 9- bis[bis(2-hydroxyethyl)-carbamoylmethyl]-3,6,9--triazaundecane dicarboxylic acid, N 6- carboxymethyl-N 3 ,N 9 -bis(2,3,4,5,6-pentahydroxyhexyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis[2,3-dihydroxypropyl-1-(hydroxymethyl)carbamoylmethyl]--3,6,9-triazaundecane dicarboxylic acid.
Claim 7
Dependent Claim 6 words
Trans-1,2-diamino-N,N'-bis(carboxymethyl)--N-N'-bis(2,3-dihydroxypropylcarbamoylmethyl)-cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N-N'-bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)cyclohexane, trans-1,2-diamino--N,N'-bis(carboxymethyl)-N,N'-bis[bis(2-hydroxyethyl)carbamoylmethyl]cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N-N'-bis(2-hydro- xyethylcarbamoylmethyl)cyclohexane, trans-1,2--diamino-N,N'-bis(carboxymethyl)-N-N'-bis[2-hydroxy-1-(hydroxymethyl)ethylcarbamoylmethyl]cyclohexane.
Claim 8
Dependent Claim 6 words
Trans-1,2-diamino-N,N'-bis(carboxymethyl)--N-N'-bis(2,3-dihydroxypropylcarbamoylmethyl)-cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N-N'-bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)cyclohexane, trans-1,2-diamino--N,N'-bis(carboxymethyl)-N,N'-bis[bis(2-hydroxyethyl)carbamoylmethyl]cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N-N'-bis(2-hydro- xyethylcarbamoylmethyl)cyclohexane, trans-1,2--diamino-N,N'-bis(carboxymethyl)-N-N'-bis[2-hydroxy-1-(hydroxymethyl)ethylcarbamoylmethyl]cyclohexane.
Claim 9
Dependent Claim 37 words
N3,N6-bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6-diazaoctane dicarboxylic acid, N 3 ,N 6 -bis[2-hydroxy-1-(hydroxymethyl)ethylcarbamoylmethyl)-3,6-diazaoctane dicarboxylic acid, N3,N6-bis(2,3-dihydroxypropylcarbamoylmethyl)--3,6-diazaoctane dicarboxylic acid, N 3 ,N 6- bis[bis-(2-hydroxyethyl)carbamoylmethyl)-3,6-diazaoc- tane dicarboxylic acid, N 3 ,N 6 -bis[2,3-dihydroxypropyl-1-(hydroxymethyl)carbamoylmethyl]-3,6-diaza- octane dicarboxylic acid, N 3 ,N 6- bis(2-hydroxy- ethylcarbamoylmethyl]-3,6-diazaoctane dicarboxylic acid.
Claim 10
Dependent Claim 37 words
N3,N6-bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6-diazaoctane dicarboxylic acid, N 3 ,N 6 -bis[2-hydroxy-1-(hydroxymethyl)ethylcarbamoylmethyl)-3,6-diazaoctane dicarboxylic acid, N3,N6-bis(2,3-dihydroxypropylcarbamoylmethyl)--3,6-diazaoctane dicarboxylic acid, N 3 ,N 6- bis[bis-(2-hydroxyethyl)carbamoylmethyl)-3,6-diazaoc- tane dicarboxylic acid, N 3 ,N 6 -bis[2,3-dihydroxypropyl-1-(hydroxymethyl)carbamoylmethyl]-3,6-diaza- octane dicarboxylic acid, N 3 ,N 6- bis(2-hydroxy- ethylcarbamoylmethyl]-3,6-diazaoctane dicarboxylic acid.
Claim 11
Dependent Claim 13 words
Use of the compounds according to claims 3 to 6 as complex formers.
Claim 12
Dependent Claim 263 words
Process for the preparation of compounds of general formula I according to claim 1, characterised in that one reacts in a known manner a) for the preparation of compounds in which R 1 represents the group R 4 either a compound of the general formula II where R 2 and R 3 have the meanings given in claim 1 and Q' has the meaning given in claim 1 for Q, however instead of the group the group is meant and k, n, I, w and m have the meanings given in claim 1, with an aminoalcohol of the general formula or a compound of the general formula III where R 2 and R 3 have the meanings given in claim 1, R 6 represents a lower alkyl group and Q" has the meaning given in claim 1, but instead of the group the group is meant with R 6 having the above given meaning, and k, n, I, w and m having the meanings given in claim 1, with an aminoalcohol of the general formula or b) for the preparation of compounds of formula I in which R' represents a carboxyl group, a compound of the general formula where Y and Z are each oxygen or Y represents a hydroxy group and Z represents an OR 6 grouping, and R 2 , R 3 , R 6 , k, n, w and m have the above given meanings, with an aminoalcohol of the general formula R 4 and if desired from the acids the salts, metal complexes or metal complex salts are prepared.
Claim 13
Dependent Claim 21 words
Compounds according to claims 1 and 2, characterised in that at least one of the substituents X represents an alkali-metal ion.
Claim 14
Dependent Claim 37 words
Compounds according to claims 1, 2 and 9, characterised in that at least one part of the substituents X are ion-equivalents of metals of atomic numbers 20 to 32, 42 to 44, 49 or 57 to 83.
Claim 15
Dependent Claim 59 words
Gadolinium complexes of N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3,4-trihydroxybutyl--carbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6- carboxymethyl-N 3 ,N 9- bis(2,3-dihydroxypropyl- -carbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N6-carboxymethyl-N3,N9-bis(2,3-dihydroxypropyl- -N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N6-carboxymethyl-N3,N9-bis[2-hydroxy-1-(hydroxymethyl)-ethylcarbamoylmethyll-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis[bis(2-hydroxyethyl)- -carbamoylmethyl]-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3,4,5,6-pentahy- droxyhexyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, and N 6 -carboxymethyl-N 3 ,N 9- bis[2,3-dihydroxypropyl--1-(hydroxymethyl)carbamoylmethyl-3,6,9-triazaundecane dicarboxylic acid.
Claim 16
Dependent Claim 59 words
Gadolinium complexes of N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3,4-trihydroxybutyl--carbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6- carboxymethyl-N 3 ,N 9- bis(2,3-dihydroxypropyl- -carbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N6-carboxymethyl-N3,N9-bis(2,3-dihydroxypropyl- -N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N6-carboxymethyl-N3,N9-bis[2-hydroxy-1-(hydroxymethyl)-ethylcarbamoylmethyll-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis[bis(2-hydroxyethyl)- -carbamoylmethyl]-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3,4,5,6-pentahy- droxyhexyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, and N 6 -carboxymethyl-N 3 ,N 9- bis[2,3-dihydroxypropyl--1-(hydroxymethyl)carbamoylmethyl-3,6,9-triazaundecane dicarboxylic acid.
Claim 17
Dependent Claim 22 words
Lanthanum-, dysprosium-, holmium-, terbium-, ytterbium-, cerium-, samarium-, bismuth-, chromium- and iron complex of N 6- carboxymethyl--N 3 ,N 9- bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid.
Claim 18
Dependent Claim 22 words
Lanthanum-, dysprosium-, holmium-, terbium-, ytterbium-, cerium-, samarium-, bismuth-, chromium- and iron complex of N 6- carboxymethyl--N 3 ,N 9- bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid.
Claim 19
Dependent Claim 21 words
Manganese complex of trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'- -bis(2,3-dihydroxypropylcarbamoylmethyl)cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'- -bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'- -bis[bis(2-hydroxyethyl)-carbamoylmethyl)cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'- -bis(2-hydroxyethylcarbamoylmethyl)cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'- -bis[2-hydroxy-1-(hydroxymethyl)ethylcarbamoylmethyl]cyclohexane, and N 3 ,N 6- bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6-diazaoctane dicarboxylic acid.
Claim 20
Dependent Claim 21 words
Manganese complex of trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'- -bis(2,3-dihydroxypropylcarbamoylmethyl)cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'- -bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'- -bis[bis(2-hydroxyethyl)-carbamoylmethyl)cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'- -bis(2-hydroxyethylcarbamoylmethyl)cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'- -bis[2-hydroxy-1-(hydroxymethyl)ethylcarbamoylmethyl]cyclohexane, and N 3 ,N 6- bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6-diazaoctane dicarboxylic acid.
Claim 21
Dependent Claim 16 words
Sodium salt of the calcium complex of N 6- -carboxymethyl-N 3 ,N 9- bis(2,3-dihydroxypropylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid.
Claim 22
Dependent Claim 16 words
Sodium salt of the calcium complex of N 6- -carboxymethyl-N 3 ,N 9- bis(2,3-dihydroxypropylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid.
Claim 23
Dependent Claim 31 words
Complexes of N 6- carboxymethyl-N 3 ,N 9- bis-(2,3-dihydroxypropylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid with 111 In, 113m In, 67 Cu, 67 Ga, 169 Yb , 1 5 3 G d and 99m Tc.
Claim 24
Dependent Claim 31 words
Complexes of N 6- carboxymethyl-N 3 ,N 9- bis-(2,3-dihydroxypropylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid with 111 In, 113m In, 67 Cu, 67 Ga, 169 Yb , 1 5 3 G d and 99m Tc.
Claim 25
Dependent Claim 16 words
Mono-N-methylglucamin salt of the zinc complex of N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid.
Claim 26
Dependent Claim 16 words
Mono-N-methylglucamin salt of the zinc complex of N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid.
Claim 27
Dependent Claim 13 words
Diagnostic agent containing a compound according to claims 11 to 13 and 15.
Claim 28
Dependent Claim 11 words
Pharmaceutical preparations containing a compound according to claims 14 and 16.
Claim 29
Dependent Claim 266 words
Use of at least one physiologically compatible complex salt of the general formula I where R 1 represents a COOX group or the group R 2 and R 3 are the same or different and represent a hydrogen atom, a lower straight or branched chain hydrocarbon group, a phenyl or a benzyl group, or either R 2 or R 3 represents the group CH 2 COOX or R 2 and R 3 together represent a trimethylene or tetramethylene group, R 4 represents a straight or branched chain mono- or polyhydroxyalkyl group, R 5 represents a hydrogen atom, a lower straight or branched chain optionally mono- or polyhydroxylated hydrocarbon group, Q represents an oxygen or sulphur atom orthe group -N-(CH 2 )j-R x , where j is a number 1 to 4 and R x represents a hydrogen atom, a lower alkyl group of 1 to 4 carbon atoms, a COOX group or, when j > 1, the group where k and m are the same or different and represent the numbers 0 or 2, I represents the numbers 1 or 2 and n and w are the same or different and represent the numbers 0 or 1, where n and w only represent the number 1 when k and m represent the number 2, and X represents hydrogen and/or metal ion equivalents, as well as their salts with physiologically acceptable bases, characterised in that at least one part of the substituents X are ion-equivalents of metals of atomic numbers 20 to 32, 42 to 44, 49 or 57 to 83, in the preparation of diagnostic agents.
Claim 30
Dependent Claim 266 words
Use of at least one physiologically compatible complex salt of the general formula I where R 1 represents a COOX group or the group R 2 and R 3 are the same or different and represent a hydrogen atom, a lower straight or branched chain hydrocarbon group, a phenyl or a benzyl group, or either R 2 or R 3 represents the group CH 2 COOX or R 2 and R 3 together represent a trimethylene or tetramethylene group, R 4 represents a straight or branched chain mono- or polyhydroxyalkyl group, R 5 represents a hydrogen atom, a lower straight or branched chain optionally mono- or polyhydroxylated hydrocarbon group, Q represents an oxygen or sulphur atom orthe group -N-(CH 2 )j-R x , where j is a number 1 to 4 and R x represents a hydrogen atom, a lower alkyl group of 1 to 4 carbon atoms, a COOX group or, when j > 1, the group where k and m are the same or different and represent the numbers 0 or 2, I represents the numbers 1 or 2 and n and w are the same or different and represent the numbers 0 or 1, where n and w only represent the number 1 when k and m represent the number 2, and X represents hydrogen and/or metal ion equivalents, as well as their salts with physiologically acceptable bases, characterised in that at least one part of the substituents X are ion-equivalents of metals of atomic numbers 20 to 32, 42 to 44, 49 or 57 to 83, in the preparation of diagnostic agents.
Claim 31
Dependent Claim 68 words
Use of the gadolinium complexes of N6-carboxymethyl-N3,N9-bis(2,3,4-trihydroxybutyl--carbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6- carboxymethyl-N 3 ,N 9- bis(2,3-dihydroxypropyl- -carbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N6-carboxymethyl-N3,N9-bis(2,3-dihydroxypropyl- -N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6- carboxymethyl-N 3 ,N 9- bis[2-hydroxy-1-hydroxymethyl)-ethylcarbamoylmethyl]-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis[bis(2-hydroxyethyl)- -carbamoylmethyl]-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3,4,5,6-pentahy- droxyhexyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, and N 6 -carboxymethyl-N 3 ,N 9 -bis[2,3-dihydroxypropyl--1-(hydroxymethyl)carbamoylmethyl]-3,6,9-triazaundecane dicarboxylic acid, in the preparation of diagnostic agents.
Claim 32
Dependent Claim 68 words
Use of the gadolinium complexes of N6-carboxymethyl-N3,N9-bis(2,3,4-trihydroxybutyl--carbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6- carboxymethyl-N 3 ,N 9- bis(2,3-dihydroxypropyl- -carbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N6-carboxymethyl-N3,N9-bis(2,3-dihydroxypropyl- -N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, N 6- carboxymethyl-N 3 ,N 9- bis[2-hydroxy-1-hydroxymethyl)-ethylcarbamoylmethyl]-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis[bis(2-hydroxyethyl)- -carbamoylmethyl]-3,6,9-triazaundecane dicarboxylic acid, N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3,4,5,6-pentahy- droxyhexyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid, and N 6 -carboxymethyl-N 3 ,N 9 -bis[2,3-dihydroxypropyl--1-(hydroxymethyl)carbamoylmethyl]-3,6,9-triazaundecane dicarboxylic acid, in the preparation of diagnostic agents.
Claim 33
Dependent Claim 30 words
Use of lanthanum, dysprosium-, holmium-, terbium-, ytterbium-, cerium-, samarium-, bismuth-, chromium- and iron complex of N 6- carboxymethyl--N 3 ,N 9 -bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid in the preparation of diagnostic agents.
Claim 34
Dependent Claim 30 words
Use of lanthanum, dysprosium-, holmium-, terbium-, ytterbium-, cerium-, samarium-, bismuth-, chromium- and iron complex of N 6- carboxymethyl--N 3 ,N 9 -bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid in the preparation of diagnostic agents.
Claim 35
Dependent Claim 29 words
Use of manganese complexes of trans- 1,2-diamino-N,N'-bis(carboxymethyl)-N,N'--bis(2,3-dihydroxypropylcarbamoylmethyl)-cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'--bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'- -bis[bis(2-hydroxyethyl)carbamoylmethyl]cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'--bis(2-hydroxyethylcarbamoylmethyl)cyclohexane, trans-1, 2-diamino-N, N'-bis(carboxymethyl)-N,N'- -bis[2-hydroxy-1-(hydroxymethyl)ethylcarbamoylmethyl]cyclohexane, and N 3 ,N 6 -bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6-diazaoctane dicarboxylic acid in the preparation of diagnostic agents.
Claim 36
Dependent Claim 29 words
Use of manganese complexes of trans- 1,2-diamino-N,N'-bis(carboxymethyl)-N,N'--bis(2,3-dihydroxypropylcarbamoylmethyl)-cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'--bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'- -bis[bis(2-hydroxyethyl)carbamoylmethyl]cyclohexane, trans-1,2-diamino-N,N'-bis(carboxymethyl)-N,N'--bis(2-hydroxyethylcarbamoylmethyl)cyclohexane, trans-1, 2-diamino-N, N'-bis(carboxymethyl)-N,N'- -bis[2-hydroxy-1-(hydroxymethyl)ethylcarbamoylmethyl]cyclohexane, and N 3 ,N 6 -bis(2,3-dihydroxypropyl-N-methylcarbamoylmethyl)-3,6-diazaoctane dicarboxylic acid in the preparation of diagnostic agents.
Claim 37
Dependent Claim 24 words
Use of sodium salt of the calcium complex of N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3-dihydroxypropylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid in the preparation of diagnostic agents.
Claim 38
Dependent Claim 24 words
Use of sodium salt of the calcium complex of N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3-dihydroxypropylcarbamoylmethyl)-3,6,9-triazaundecane dicarboxylic acid in the preparation of diagnostic agents.
Claim 39
Dependent Claim 36 words
Use of complexes of N 6- carboxymethyl-N 3 ,-N 9 -bis(2,3-dihydroxypropylcarbamoylmethyl)-3,6,-9-triazaundecane dicarboxylic acid with 111 In, 113m In, 67 CU , 67 Ga, 169 Yb, 153 Gd and 99m Tc in the preparation of diagnostic agents.
Claim 40
Dependent Claim 36 words
Use of complexes of N 6- carboxymethyl-N 3 ,-N 9 -bis(2,3-dihydroxypropylcarbamoylmethyl)-3,6,-9-triazaundecane dicarboxylic acid with 111 In, 113m In, 67 CU , 67 Ga, 169 Yb, 153 Gd and 99m Tc in the preparation of diagnostic agents.
Claim 41
Dependent Claim 24 words
Use of mono-N-methylglucamine salt of the zinc complex of N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3--dihydroxypropyl-N-methylcarbamoylmethyl)-3,6,-9-triazaundecane dicarboxylic acid in the preparation of diagnostic agents.
Claim 42
Dependent Claim 24 words
Use of mono-N-methylglucamine salt of the zinc complex of N 6 -carboxymethyl-N 3 ,N 9 -bis(2,3--dihydroxypropyl-N-methylcarbamoylmethyl)-3,6,-9-triazaundecane dicarboxylic acid in the preparation of diagnostic agents.

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