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WO1996016679B1 - Paramagnetic complexes of n-alkyl-n-hydroxylamides of organic acids and emulsions containing same for magnetic resonance imaging (mri) - Google Patents

Paramagnetic complexes of n-alkyl-n-hydroxylamides of organic acids and emulsions containing same for magnetic resonance imaging (mri)

Info

Publication number
WO1996016679B1
WO1996016679B1 PCT/US1995/014508 US9514508W WO9616679B1 WO 1996016679 B1 WO1996016679 B1 WO 1996016679B1 US 9514508 W US9514508 W US 9514508W WO 9616679 B1 WO9616679 B1 WO 9616679B1
Authority
WO
WIPO (PCT)
Prior art keywords
group
hydroxyl
physiologically acceptable
metal ion
acceptable emulsion
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1995/014508
Other languages
French (fr)
Other versions
WO1996016679A1 (en
Filing date
Publication date
Priority claimed from US08/346,885 external-priority patent/US5614170A/en
Application filed filed Critical
Priority to JP8518809A priority Critical patent/JPH11500413A/en
Priority to EP95942846A priority patent/EP0794801A1/en
Priority to AU44060/96A priority patent/AU4406096A/en
Publication of WO1996016679A1 publication Critical patent/WO1996016679A1/en
Publication of WO1996016679B1 publication Critical patent/WO1996016679B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Abstract

Emulsions of paramagnetic contrast agents, and processes of making and using them are disclosed. The emulsions contain water, a dispersed oil phase and a complex of a paramagnetic metal ion and an organic acid chelator, for example DTPA (diethylenetriaminepentaacetic acid), having a C10-C30 saturated aliphatic group and a hydroxyl group bonded to the nitrogen atom. The emulsions are very stable and therapeutically acceptable for intravenous administration to enhance MRI imaging.

Claims

AMENDED CLAIMS
[received by the International Bureau on 28 May 1996 (28.05.96); original claims 1, 8 and 20 amended; remaining claims unchanged (3 paqes)] 1. A complex of a paramagnetic metal ion and an organic chelator having the formula -OC-CH2 CH2-CO-M
\ /
N-CH2-CH2- (N-CH2-CH2)n-N
/ I \
M-OC-CH2 CH2 CH2-CO-M
I CO-M wherein from 2 to 5 M groups are hydroxyl, n=0 to 2, and at least one remaining M group is NR1R2, each Rx is a C10-
C30 saturated aliphatic group and R2 is hydroxyl.
8. A physiologically acceptable emulsion for enhancement of MRI imaging comprising water, a dispersed oil phase and a complex of a paramagnetic metal ion and an organic chelator having the formula
M-OC-CH2 CH2-CO-M
\ /
N-CH2-CH2- (N-CH2-CH2)n-N
M-OC-CH2 / \ CH2-CO-M
Figure imgf000004_0001
wherein from 2 to 5 M groups are hydroxyl, n=0 to 2, and at least one remaining M group is NRJRJ, each Rx is a C10- C30 saturated aliphatic group and R2 is hydroxyl.
9. The physiologically acceptable emulsion of claim 8 wherein said metal ion is a lanthanide element of atomic numbers 58-70 or a transition metal of atomic numbers 21- 29, 42 or 44.
10. The physiologically acceptable emulsion of claim 8 wherein said metal ion is selected from a group consisting Gd(III) , Mn(II) , iron and dysprosium.
11. The physiologically acceptable emulsion of claim 8 wherein said organic chelator is an acid selected from the group consisting of ethylenediaminetetraacetic acid and diethylenetriaminepentaacetic acid.
12. The physiologically acceptable emulsion of claim 8 wherein each Rj is C14-C22. 20. A physiologically acceptable emulsion for enhancement of MRI imaging comprising water, a dispersed oil phase selected from the group consisting of an oil and fluorochemical, and mixtures thereof, a surfactant, and a complex of a paramagnetic metal ion and an organic chelator having the formula
M-0C-CH2 CH2-CO-M
\ /
N-CH2-CH2- (N-CH2-CH2)n-N
/ I \
M-OC-CH2 CH2 CH2-CO-M
I
CO-M wherein from 2 to 5 M groups are hydroxyl, n=0 to 2 and at least one remaining M group is NR1R2, each Rx is a C10-C30 saturated aliphatic group and R2 is hydroxyl .
PCT/US1995/014508 1994-11-30 1995-11-09 Paramagnetic complexes of n-alkyl-n-hydroxylamides of organic acids and emulsions containing same for magnetic resonance imaging (mri) Ceased WO1996016679A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP8518809A JPH11500413A (en) 1994-11-30 1995-11-09 Paramagnetic complexes of N-alkyl-N-hydroxylamides of organic acids and emulsions containing them for magnetic resonance imaging (MRI)
EP95942846A EP0794801A1 (en) 1994-11-30 1995-11-09 Paramagnetic complexes of n-alkyl-n-hydroxylamides of organic acids and emulsions containing same for magnetic resonance imaging (mri)
AU44060/96A AU4406096A (en) 1994-11-30 1995-11-09 Paramagnetic complexes of N-alkyl-N-hydroxylamides of organicacids and emulsions containing same for magnetic resonance imaging (MRI)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/346,885 US5614170A (en) 1994-11-30 1994-11-30 Paramagnetic complexes of N-alkyl-N-hydroxylamides of organic acids and emulsions containing same for magnetic resonance imaging (MRI)
US08/346,885 1994-11-30

Publications (2)

Publication Number Publication Date
WO1996016679A1 WO1996016679A1 (en) 1996-06-06
WO1996016679B1 true WO1996016679B1 (en) 1996-08-01

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/014508 Ceased WO1996016679A1 (en) 1994-11-30 1995-11-09 Paramagnetic complexes of n-alkyl-n-hydroxylamides of organic acids and emulsions containing same for magnetic resonance imaging (mri)

Country Status (6)

Country Link
US (1) US5614170A (en)
EP (1) EP0794801A1 (en)
JP (1) JPH11500413A (en)
AU (1) AU4406096A (en)
CA (1) CA2205232A1 (en)
WO (1) WO1996016679A1 (en)

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US7279150B2 (en) * 2002-01-24 2007-10-09 Barnes-Jewish Hospital Chelating agents with lipophilic carriers
US6869591B2 (en) * 2002-03-26 2005-03-22 Barnes-Jewish Hospital Paramagnetic particles that provide improved relaxivity
WO2005122891A1 (en) 2004-06-09 2005-12-29 Kereos, Inc. Lipophilic derivatives of chelate monoamides
FR2883562B1 (en) 2005-03-24 2009-02-27 Guerbet Sa LIPOPHILIC CHELATES AND THEIR USE IN IMAGING
LU503039B1 (en) * 2022-11-11 2024-05-13 Teresa Carlomagno Novel photocleavable spin-labels
CN115947672B (en) * 2023-01-04 2024-02-27 成都威斯津生物医药科技有限公司 Compounds, liposomes and drug carriers for drug delivery

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