US4647447A
Expired / Lapsed
US
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Diagnostic media
Assignee: Bayer Pharma AG
•
Filing: 1984-01-23
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Granted: 1987-03-03
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Expires: 2004-01-23
Abstract
Abstract A diagnostic medium contains at least one physiologically well tolerated complex salt comprising an anion of a complexing acid and one or more central ion or ions of an element with an atomic number of 21 to 29, 42, 44 or 57 to 83 and, optionally, one or more physiologically biocompatible cation or cations of an inorganic and/or organic base or amino acid, optionally, with additives customary in galenic formulations, dissolved or suspended in an aqueous medium.
Inventors
- 👤 Heinz Gries
- 👤 Douwe Rosenberg
- 👤 Hanns-Joachim Weinmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 12:39
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/3804; C07F9/3839; C07F9/386; A; A61; A61K; A61K49/00; A61K49/04; A61K49/06; A61K49/08; A61K49/085; A61K49/10; A61K49/101; A61K49/103; A61K49/105; A61K49/14; A61K49/16; A61K49/18; A61K49/1806; A61K49/1812; C07C; C07C323/00; C07C323/23; C07C323/24; C07C323/25; C07D; C07D257/00; C07D257/02; C07F9/3808; C07F9/3817
Claims Analysis
Total Claims: 72
Claim 1
Independent Claim
321 words
A method of performing an NMR diagnostic procedure in a patient in need of the same comprising administering to the patient an effective amount of an NMR diagnostic medium and then exposing the patient to an NMR measurement step to which the diagnostic medium is responsive thereby imaging at least a portion of the patient's body, wherein the diagnostic medium comprises a physiologically compatible salt of (a) an anion of a complexing acid and (b) at least one central ion of an element with an atomic number of 21 to 29, 42, 44 or 57 to 83 chelated therewith, wherein the salt is of the formula I or II ##STR8## or N(CH.sub.2 X).sub.3, (II) wherein X is --COOY, --PO 3 HY or --CONHOY; Y is a hydrogen atom, a metal ion equivalent or a physiologically biocompatible cation of an inorganic or organic base or amino acid; A is --CHR 2 --CHR 3 --, --CH 2 --CH 2 --(ZCH 2 --CH 2 ) m --, ##STR9## each R 1 is a hydrogen atom or methyl; R 2 and R 3 together represent a trimethylene group or a tetramethylene group or individually are hydrogen, C 1-8 -alkyl, phenyl or benzyl, W is --NN--, --NHCOCH 2 -- or --NHCS--; m is the number 1, 2 or 3 Z is an oxygen atom, a sulfur atom, >NCH 2 X, or >NCH 2 CH 2 OR 4 R 4 is C 1-8 -alkyl V is one of the X groups or is --CH 2 OH, or --CONH(CH 2 ) n X, n is a number from 1 to 12; if R 1 , R 2 and R 3 are hydrogen atoms, both V's together are the group ##STR10## w is a number 1, 2 or 3; provided that at least two of the substituents Y are metal ion equivalents of an element with an atomic number of 21 to 29, 42, 44 or 57 to 83.
Claim 2
Independent Claim
321 words
A method of performing an NMR diagnostic procedure in a patient in need of the same comprising administering to the patient an effective amount of an NMR diagnostic medium and then exposing the patient to an NMR measurement step to which the diagnostic medium is responsive thereby imaging at least a portion of the patient's body, wherein the diagnostic medium comprises a physiologically compatible salt of (a) an anion of a complexing acid and (b) at least one central ion of an element with an atomic number of 21 to 29, 42, 44 or 57 to 83 chelated therewith, wherein the salt is of the formula I or II ##STR8## or N(CH.sub.2 X).sub.3, (II) wherein X is --COOY, --PO 3 HY or --CONHOY; Y is a hydrogen atom, a metal ion equivalent or a physiologically biocompatible cation of an inorganic or organic base or amino acid; A is --CHR 2 --CHR 3 --, --CH 2 --CH 2 --(ZCH 2 --CH 2 ) m --, ##STR9## each R 1 is a hydrogen atom or methyl; R 2 and R 3 together represent a trimethylene group or a tetramethylene group or individually are hydrogen, C 1-8 -alkyl, phenyl or benzyl, W is --NN--, --NHCOCH 2 -- or --NHCS--; m is the number 1, 2 or 3 Z is an oxygen atom, a sulfur atom, >NCH 2 X, or >NCH 2 CH 2 OR 4 R 4 is C 1-8 -alkyl V is one of the X groups or is --CH 2 OH, or --CONH(CH 2 ) n X, n is a number from 1 to 12; if R 1 , R 2 and R 3 are hydrogen atoms, both V's together are the group ##STR10## w is a number 1, 2 or 3; provided that at least two of the substituents Y are metal ion equivalents of an element with an atomic number of 21 to 29, 42, 44 or 57 to 83.
Claim 3
Dependent Claim
19 words
A method of claim 1 wherein the concentration of salt in the medium is 1 μmole to 1 mole.
Claim 4
Dependent Claim
19 words
A method of claim 1 wherein the concentration of salt in the medium is 1 μmole to 5 mmole.
Claim 5
Dependent Claim
19 words
A method of claim 1 wherein the concentration of salt in the medium is 250 mmole to 1 mole.
Claim 6
Dependent Claim
23 words
A method of claim 1 wherein the salt in the medium is the monosodium/mono-N-methylglucamine mixed salt of the gadolinium(III) complex of diethylenetriaminepentaacetic acid.
Claim 7
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the disodium salt of the gadolinium(III) complex of diethylenetriaminepentaacetic acid.
Claim 8
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the di-N-methylglucamine salt of the iron(III) complex of diethylenetriaminepentaacetic acid.
Claim 9
Dependent Claim
23 words
A method of claim 1 wherein the salt in the medium is the disodium salt of the iron (III) complex of diethylenetriaminepentaacetic acid.
Claim 10
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the disodium salt of the manganese(II) complex of diethylenetriaminepentaacetic acid.
Claim 11
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the di-N-methylglucamine salt of the bismuth(III) complex of diethylenetriaminepentaacetic acid.
Claim 12
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the di-N-methylglucamine salt of the manganese(II) complex of trans-1,2-cyclohexenediaminetetraacetic acid.
Claim 13
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the disodium salt of the ytterbium(III) complex of diethylenetriaminepentaacetic acid.
Claim 14
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the N-methylglucamine salt of the gadolinium(III) complex of 1,4,7,10-tetraazacyclododecanetetraacetic acid.
Claim 15
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the disodium salt of the manganese(II) complex of trans-1,2-cyclohenediaminetetraacetic acid.
Claim 16
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the disodium salt of the bismuth(III) complex of diethylenetriaminepentaacetic acid.
Claim 17
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the di-N-methyglucamine salt of the gadolinium(III) complex of 13,23-dioxo-15,18,21-tris-(carboxymethyl)-12,15,18,21,24-pentaazapentatriacontanedioic acid.
Claim 18
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the sodium salt of the gadolinium(III) complex of 1,4,7,10-tetraazacyclododecanetetraacetic acid.
Claim 19
Dependent Claim
21 words
A method of claim 1 wherein the salt in the medium comprises liposomes charged with the gladolinium(III) complex of diethylenetriaminepentaacetic acid.
Claim 20
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the disodium salt of the holmium(III) complex of diethylenetriaminepentaacetic acid.
Claim 21
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the disodium salt of the lanthanum(III) complex of diethylenetriaminepentaacetic acid.
Claim 22
Dependent Claim
26 words
A method of claim 1 wherein the salt in the medium is the disodium salt of the di-N-methylglucamine salt of the ytterbium(III) complex of diethylenetriaminepentaacetic acid.
Claim 23
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the disodium salt of the sumarium(III) complex of diethylenetriaminepentaacetic acid.
Claim 24
Dependent Claim
22 words
A method of claim 1 wherein the salt in the medium is the disodium salt of the gadolinium(III) complex of 13,23-dioxo-15,18,21-tris-(carboxymethyl)-12,15,18,21,24-pentaazapentatriacontanedioic acid.
Claim 25
Dependent Claim
106 words
In a method of imaging body tissue in a patient, comprising subjecting the patient to NMR tomography, the improvement comprising, prior to performing the NMR tomography, administering to the patient an effective amount of a pharmaceutical agent for affecting the relaxation times of atoms in body tissues undergoing NMR diagnosis, whereby image contrast is enhanced, said agent comprising an amount, effective to affect such relaxation times, of a paramagnetic, physiologically compatible salt of a physiologically compatible chelate complex of an ion of a lanthanide element of atomic numbers 57-70, or of a transition metal of atomic numbers 21-29, 42, or 44; and a pharmaceutically acceptable carrier.
Claim 26
Dependent Claim
106 words
In a method of imaging body tissue in a patient, comprising subjecting the patient to NMR tomography, the improvement comprising, prior to performing the NMR tomography, administering to the patient an effective amount of a pharmaceutical agent for affecting the relaxation times of atoms in body tissues undergoing NMR diagnosis, whereby image contrast is enhanced, said agent comprising an amount, effective to affect such relaxation times, of a paramagnetic, physiologically compatible salt of a physiologically compatible chelate complex of an ion of a lanthanide element of atomic numbers 57-70, or of a transition metal of atomic numbers 21-29, 42, or 44; and a pharmaceutically acceptable carrier.
Claim 27
Dependent Claim
20 words
A method of claim 24 wherein the concentration of said salt in the agent is 1 μmole to 1 mole.
Claim 28
Dependent Claim
231 words
In a method of imaging body tissue in a patient, comprising subjecting the patient to NMR tomography, the improvement comprising, prior to performing the NMR tomography, administering to the patient an effective amount of a pharmaceutical agent for affecting the relaxation times of atoms in body tissues undergoing NMR diagnosis whereby image contrast is enhanced, said agent comprising an amount effective to affect such relaxation times of a paramagnetic, physiologically compatible salt of a complex of an ion and a ligand; and a pharmaceutically acceptable carrier; wherein the complexed ion is an ion of a lanthanide element of atomic numbers 57-70, or of a transition metal of atomic numbers 21-29, 42, or 44; and wherein the ligand is that of a complexing agent which (a) is an aminopolycarboxylic acid which is nitrilotriacetic acid, N-hydroxyethyl-N,N',N'-ethylenediaminetriacetic acid, N,N,N',N",N"-diethylenetriaminepentaacetic acid or N-hydroxyethyliminodiacetic acid; (b) of the formula ##STR11## wherein R 1 and R 1 ' are identical or different and each is hydrogen or alkyl of 1-4 carbon atoms and p is an integer of 0-4; or (c) an aminopolycarboxylic acid of the formula ##STR12## wherein m is an integer of 1 to 4, n is an integer of 0 to 2, and R 5 is C 4-12 -alkyl, C 4-12 -alkenyl, C 4-12 -cycloalkyl, C 4-12 -cycloalkenyl, C 7-12 -hydrocarbon aralkyl, C 8-12 -hydrocarbon alkenyl, C 6-12 -hydrocarbon aryl or --CH 2 COOH.
Claim 29
Dependent Claim
231 words
In a method of imaging body tissue in a patient, comprising subjecting the patient to NMR tomography, the improvement comprising, prior to performing the NMR tomography, administering to the patient an effective amount of a pharmaceutical agent for affecting the relaxation times of atoms in body tissues undergoing NMR diagnosis whereby image contrast is enhanced, said agent comprising an amount effective to affect such relaxation times of a paramagnetic, physiologically compatible salt of a complex of an ion and a ligand; and a pharmaceutically acceptable carrier; wherein the complexed ion is an ion of a lanthanide element of atomic numbers 57-70, or of a transition metal of atomic numbers 21-29, 42, or 44; and wherein the ligand is that of a complexing agent which (a) is an aminopolycarboxylic acid which is nitrilotriacetic acid, N-hydroxyethyl-N,N',N'-ethylenediaminetriacetic acid, N,N,N',N",N"-diethylenetriaminepentaacetic acid or N-hydroxyethyliminodiacetic acid; (b) of the formula ##STR11## wherein R 1 and R 1 ' are identical or different and each is hydrogen or alkyl of 1-4 carbon atoms and p is an integer of 0-4; or (c) an aminopolycarboxylic acid of the formula ##STR12## wherein m is an integer of 1 to 4, n is an integer of 0 to 2, and R 5 is C 4-12 -alkyl, C 4-12 -alkenyl, C 4-12 -cycloalkyl, C 4-12 -cycloalkenyl, C 7-12 -hydrocarbon aralkyl, C 8-12 -hydrocarbon alkenyl, C 6-12 -hydrocarbon aryl or --CH 2 COOH.
Claim 30
Dependent Claim
23 words
A method of claim 26 wherein the administration is orally or intravasally and is performed about 15-60 minutes before performing the NMR tomography.
Claim 31
Dependent Claim
15 words
A method of claim 27 wherein the dosage of complex salt is 1-100 μmol/kg intravenously.
Claim 32
Dependent Claim
14 words
A method of claim 26, wherein the pharmaceutical agent has a pH of 6.5-7.5.
Claim 33
Dependent Claim
12 words
A method of claim 26, wherein the pharmaceutical agent is blood isotonic.
Claim 34
Dependent Claim
25 words
A method of claim 26, wherein the pharmaceutical agent comprises the paramagnetic complex salt dissolved or suspended in water in a concentration of 5-250 mmol/l.
Claim 35
Dependent Claim
28 words
A method of claim 26, wherein in the pharmaceutical agent, the complex salt is a salt of the complexed ion with an inorganic or organic acid or base.
Claim 36
Dependent Claim
42 words
A method of claim 26, wherein in the pharmaceutical agent, the inorganic or organic acid or base is hydrochloric acid, sulfuric acid, acetic acid, citric acid, aspartic acid, glutamic acid, sodium hydroxide, glucamine, N-methylglucamine, N,N-dimethylglucamine, ethanolamine, diethanolamine, morpholine, lysine, ornithine or arginine.
Claim 37
Dependent Claim
30 words
A method of claim 26, wherein in the pharmaceutical agent, the complexing agent is an aminopolycarboxylic acid which is nitrilotriacetic acid, N,N,N',N'-ethylenediaminetetraacetic acid, N-hydroxyethyl-N,N',N'-ethylenediaminetriacetic acid, N,N,N',N",N"-diethylenetriaminepentaacetic acid or N-hydroxyethyliminodiacetic acid.
Claim 38
Dependent Claim
46 words
A method of claim 26, wherein in the pharmaceutical agent, the complexing agent is of the formula ##STR13## wherein R 1 and R 1 ' are identical or different and each is hydrogen or alkyl of 1-4 carbon atoms and p is an integer of 0-4.
Claim 39
Dependent Claim
70 words
A method of claim 26, wherein in the pharmaceutical agent, the complexing agent is an aminopolycarboxylic acid of the formula ##STR14## wherein m is an integer of 1 to 4, n is an integer of 0 to 2, and R 5 is C 4-12 -alkyl, C 4-12 -alkenyl, C 4-12 -cycloalkyl, C 4-12 -cycloalkenyl, C 7-12 -hydrocarbon aralkyl, C 8-12 -hydrocarbon alkenyl, C 6-12 -hydrocarbon aryl or --CH 2 COOH.
Claim 40
Dependent Claim
24 words
A method of claim 26, wherein in the pharmaceutical agent, the complexed ion is an ion of a lanthanide element of atomic numbers 57-70.
Claim 41
Dependent Claim
27 words
A method of claim 26, wherein in the pharmaceutical agent, the complexed ion is an ion of a transition metal of atomic numbers 21-29, 42, or 44.
Claim 42
Dependent Claim
24 words
A method of claim 34, wherein in the pharmaceutical agent, the complexed ion is an ion of a lanthanide element of atomic numbers 57-70.
Claim 43
Dependent Claim
27 words
A method of claim 34, wherein in the pharmaceutical agent, the complexed ion is an ion of a transition metal of atomic numbers 21-29, 42, or 44.
Claim 44
Dependent Claim
24 words
A method of claim 35, wherein in the pharmaceutical agent, the complexed ion is an ion of a lanthanide element of atomic numbers 57-70.
Claim 45
Dependent Claim
27 words
A method of claim 35, wherein in the pharmaceutical agent, the complexed ion is an ion of a transition metal of atomic numbers 21-29, 42, or 44.
Claim 46
Dependent Claim
24 words
A method of claim 36, wherein in the pharmaceutical agent, the complexed ion is an ion of a lanthanide element of atomic numbers 57-70.
Claim 47
Dependent Claim
27 words
A method of claim 36, wherein in the pharmaceutical agent, the complexed ion is an ion of a transition metal of atomic numbers 21-29, 42, or 44.
Claim 48
Dependent Claim
25 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the di-N-methylglucamine salt of the manganese(II) complex of ethylenediaminetetraacetic acid.
Claim 49
Dependent Claim
25 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the N-methylglucamine salt of the gadolinium(III) complex of ethylenediaminetetraacetic acid.
Claim 50
Dependent Claim
25 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the di-N-methylglucamine salt of the gadolinium(III) complex of diethylenetriaminepentaacetic acid.
Claim 51
Dependent Claim
25 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the di-N-methylglucamine salt of the dysprosium(III) complex of diethylenetriaminepentaacetic acid.
Claim 52
Dependent Claim
25 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the di-N-methylgucamine salt of the holmium(III) complex of diethylenetriaminepentaacetic acid.
Claim 53
Dependent Claim
25 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the disodium salt of the manganese(II) complex of ethylenediaminetetraacetic acid.
Claim 54
Dependent Claim
23 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the complex [Ni.sub.2 (C.sub.6 H.sub.18 N.sub.4).sub.3 ]Cl.sub.4.2H.sub.2 O.
Claim 55
Dependent Claim
25 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the N-methylglucamine salt of the gladolinium(III) complex of diethylenetriaminepentaacetic acid.
Claim 56
Dependent Claim
21 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the copper(II) chloride complex of 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane.
Claim 57
Dependent Claim
25 words
A method of claim 26 wherein in the pharmaceutical agent, the paramagnetic complex salt is the N-methylglucamine salt of the iron(II) complex of ethane-1-hydroxy-1,1-diphosphonic acid.
Claim 58
Dependent Claim
25 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the di-lysine salt of the gadolinium(III) complex of diethylenetriaminepentaacetic acid.
Claim 59
Dependent Claim
25 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the dimorpholine salt of the manganese(II) complex of ethylendediaminetetraacetic acid.
Claim 60
Dependent Claim
25 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the tri-diethanolamine salt of the manganese(II) complex of diethylenetriaminepentaacetic acid.
Claim 61
Dependent Claim
25 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the tri-N-methylglucamine salt of the manganese(II) complex of diethylenetriaminepentaacetic acid.
Claim 62
Dependent Claim
25 words
A method of claim 26, wherein in the pharmaceutical agent, the paramagnetic complex salt is the N-methylglucamine salt of the dysprosium(III) complex of ethylenediaminetetraacetic acid.
Claim 63
Dependent Claim
15 words
A method of claim 26, wherein in the pharmaceutical agent, the complex ion is gadolinium(III).
Claim 64
Dependent Claim
15 words
A method of claim 60, wherein in the pharmaceutical agent, the ligand is N,N,N',N",N"-diethylenetriaminepentaacetic acid.
Claim 65
Dependent Claim
37 words
A method of claim 61, wherein, in the pharmaceutical agent, the complex salt is a salt of the complexed ion with the cation of an inorganic base which is sodium or an organic base which is N-methylglucamine.
Claim 66
Dependent Claim
14 words
A method of claim 62, wherein in the pharmaceutical agent, said base is inorganic.
Claim 67
Dependent Claim
15 words
A method of claim 26, wherein in the pharmaceutical agent, the ligand is N,N,N',N",N"-diethylenetriaminepentaacetic acid.
Claim 68
Dependent Claim
126 words
In a method of imaging body tissue in a patient, comprising subjecting the patient to NMR tomography, the improvement comprising, prior to performing the NMR tomography, administering to the patient an effective amount of a pharmaceutical agent for affecting the relaxation times of atoms in body tissues undergoing NMR diagnosis, whereby image contrast is enhanced, said agent comprising an amount, effective to affect such relaxation times, of a paramagnetic, physiologically compatible salt of a complex of an ion and, as a ligand, an acyclic or cyclic complexing agent containing organic nitrogen, phosphorus, oxygen or sulfur, the complexed ion being an ion of a lanthanide element of atomic numbers 57-70, or of a transition metal of atomic numbers 21-29, 42, or 44; and a pharmaceutically acceptable carrier.
Claim 69
Dependent Claim
126 words
In a method of imaging body tissue in a patient, comprising subjecting the patient to NMR tomography, the improvement comprising, prior to performing the NMR tomography, administering to the patient an effective amount of a pharmaceutical agent for affecting the relaxation times of atoms in body tissues undergoing NMR diagnosis, whereby image contrast is enhanced, said agent comprising an amount, effective to affect such relaxation times, of a paramagnetic, physiologically compatible salt of a complex of an ion and, as a ligand, an acyclic or cyclic complexing agent containing organic nitrogen, phosphorus, oxygen or sulfur, the complexed ion being an ion of a lanthanide element of atomic numbers 57-70, or of a transition metal of atomic numbers 21-29, 42, or 44; and a pharmaceutically acceptable carrier.
Claim 70
Dependent Claim
20 words
The method of claim 65 wherein the salt is the di-N-methylglucamine salt of the nickel (II) complex of ethylenediaminetetraacetic acid.
Claim 71
Dependent Claim
20 words
A method of claim 65 wherein the salt is the diethanolamine salt of the cobalt (II) complex of ethylenediaminetetraacetic acid.
Claim 72
Dependent Claim
20 words
A method of claim 65 wherein the salt is the di-diethanolamine salt of the copper (II) complex of ethylenediaminetetraacetic acid.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-03-02 | 1990-09-01 | 1991-03-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-03-02 | 1994-09-01 | 1995-03-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-03-02 | 1998-09-01 | 1999-03-03 | $7700.00 | Window Closed / Lapsed |