US5208324A
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US
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Paramagnetic compounds
Assignee: GE Healthcare AS
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Filing: 1989-01-26
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Granted: 1993-05-04
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Expires: 2009-01-26
Abstract
Abstract There are provided paramagnetic compounds comprising a paramagnetic metal species chelated by a chelating moiety bound by an amide group to a linker group itself bound by an ester group to a macromolecule, wherein said linker group provides a carbon chain of at least 2 atoms between said amide group and said ester group. The novel compounds are particularly suitable as contrast agents, e.g. in magnetic resonance imaging.
Inventors
- 👤 Jo Klaveness
- 👤 Pal Rongved
- 👤 Per Strande
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 14:22
CPC Classifications
A; A61; A61K; A61K49/00; A61K49/06; A61K49/08; A61K49/085; A61K49/10; A61K49/12; A61K49/126; A61P; A61P39/00; A61P39/02; A61P9/00; A61P9/06; Y; Y10; Y10T; Y10T436/00; Y10T436/24
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
72 words
A paramagnetic compound comprising a paramagnetic metal species chelated by a chelating moiety bound by an amide group to a linker group itself bound by an ester group to a macromolecule selected from the group consisting of polymeric and polymerised carbohydrates and polymerised sugar alcohols, and physiologically tolerable derivatives thereof, wherein said linker group provides a carbon chain of from 2 to 11 atoms between said amide group and said ester group.
Claim 2
Dependent Claim
72 words
A paramagnetic compound comprising a paramagnetic metal species chelated by a chelating moiety bound by an amide group to a linker group itself bound by an ester group to a macromolecule selected from the group consisting of polymeric and polymerised carbohydrates and polymerised sugar alcohols, and physiologically tolerable derivatives thereof, wherein said linker group provides a carbon chain of from 2 to 11 atoms between said amide group and said ester group.
Claim 3
Dependent Claim
79 words
A compound as claimed in claim 1 wherein said linker group is a residue of an amino acid of formula I HOOC-CH.sub.2 -(CHR).sub.n -NH.sub.2 (I) wherein, n is an integer of from 1 to 10, and each R, which may be the same or different, represents a hydrogen atom or a hydroxyl, C 1-6 hydroxyalkyl, or C 1-4 alkyl group, with the proviso that R on the carbon attached to the amine group does not represent a hydroxyl group.
Claim 4
Dependent Claim
26 words
A compound as claimed in claim 2 wherein in formula I n is an integer of from 1 to 10 and R represents a hydrogen atom.
Claim 5
Dependent Claim
21 words
A compound as claimed in claim 1 wherein said linker group is a residue of a beta or gamma amino acid.
Claim 6
Dependent Claim
16 words
A compound as claimed in claim 1 wherein said linker group is a residue of beta-alanine.
Claim 7
Dependent Claim
23 words
A compound as claimed in claim 1 wherein said chelating moiety is a residue of an amino polycarboxylic acid or polycarboxylic acid derivative.
Claim 8
Dependent Claim
174 words
A compound as claimed in claim 1 wherein said chelating moiety is a residue of a compound of formula II ##STR2## wherein each of the groups Z is a group --CHR 1 X or the groups Z are together a group --(CHR 1 ) 2 --A'--(CHR 1 ) 2 --, where A' is O, S, N--CHR 1 X or N--(CHR 1 ) p --N(CHR 1 X) 2 where p is 2,3 or 4; Y is a group --(CHR 1 ) 2 --N(CHR 1 X) 2 or a group --CHR 1 X; each X, which may be the same or different, is a carboxyl group or an amide, ester or carboxylate salt derivative thereof or a group R 1 ; each R 1 , which may be the same or different, is a hydrogen atom, a hydroxyalkyl group or an optionally hydroxylated alkoxy group; with the proviso that at least two nitrogens carry a --CHR 1 X moiety wherein X is a carboxyl group or a derivative thereof as defined above, or a salt thereof.
Claim 9
Dependent Claim
24 words
A compound as claimed in claim 1 wherein said chelating moiety is a residue of a compound selected from DTPA, DOTA, and salts thereof.
Claim 10
Dependent Claim
13 words
A compound as claimed in claim 1 wherein said macromolecule is a polysaccharide.
Claim 11
Dependent Claim
17 words
A compound as claimed in claim 1 wherein said macromolecule is a dextran or a derivative thereof.
Claim 12
Dependent Claim
21 words
A compound as claimed in claim 10 wherein said macromolecule has a weight average molecular weight of from 40,000 to 500,000.
Claim 13
Dependent Claim
20 words
A compound as claimed in claim 1 wherein said paramagnetic metal is of atomic number 21-29, 42, 44 or 57-71.
Claim 14
Dependent Claim
16 words
A compound as claimed in claim 12 wherein said paramagnetic metal is Gd, Dy or Cr.
Claim 15
Dependent Claim
99 words
A process for the preparation of a macromolecular paramagnetic compound as claimed in claim 1 which process comprises admixing in a solvent an at least sparingly soluble paramagnetic metal compound, together with a macromolecular chelating agent comprising a chelating moiety bound by an amide group to a linker group itself bound by an ester group to a macromolecule selected from the group consisting of polymeric and polymerised carbohydrates and polymerised sugar alcohols, and physiologically tolerable derivatives thereof, wherein said linker group provides a carbon chain of from 2 to 11 atoms between said amide group and said ester group.
Claim 16
Dependent Claim
74 words
A macromolecular chelating compound comprising a chelating moiety bound by an amide group to a linker group itself bound by an ester group to a macromolecule selected from the group consisting of polymeric and polymerised carbohydrates and polymerised sugar alcohols, and physiologically tolerable derivatives thereof, wherein said linker group provides a carbon chain of from 2 to 11 atoms between said amide group and said ester group, or a salt of metal chelate thereof.
Claim 17
Dependent Claim
74 words
A macromolecular chelating compound comprising a chelating moiety bound by an amide group to a linker group itself bound by an ester group to a macromolecule selected from the group consisting of polymeric and polymerised carbohydrates and polymerised sugar alcohols, and physiologically tolerable derivatives thereof, wherein said linker group provides a carbon chain of from 2 to 11 atoms between said amide group and said ester group, or a salt of metal chelate thereof.
Claim 18
Dependent Claim
79 words
A process for the preparation of a chelating compound as claimed in and claim 15 which process comprises reacting a hydroxyl group containing macromolecule with an amino acid or a salt thereof, said amino acid having a carbon chain of at least two atoms between its carboxyl and amine groups; reacting the product so obtained with a carboxyl group-, or reactive carboxyl derivative-containing chelating agent; and, optionally, converting the product so obtained into a salt or metal chelate thereof.
Claim 19
Dependent Claim
10 words
A compound as claimed in claim 1 which is GdDTPA-beta-alanine-dextran.
Claim 20
Dependent Claim
42 words
A method of image generation, which method involves administering to a human or non-human animal body an effective amount of a macromolecular metal chelate as claimed in claim 1 and generating a magnetic resonance, image of at least part of said body.
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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) | 1996-05-03 | 1996-11-02 | 1997-05-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-05-03 | 2000-11-02 | 2001-05-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-05-03 | 2004-11-02 | 2005-05-04 | $7700.00 | Window Closed / Lapsed |