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
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
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 .
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 | 1994-11-30 | ||
| 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) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996016679A1 WO1996016679A1 (en) | 1996-06-06 |
| WO1996016679B1 true WO1996016679B1 (en) | 1996-08-01 |
Family
ID=23361430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1995/014508 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) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6028108A (en) * | 1998-10-22 | 2000-02-22 | America Home Products Corporation | Propofol composition comprising pentetate |
| US7279150B2 (en) * | 2002-01-24 | 2007-10-09 | Barnes-Jewish Hospital | Chelating agents with lipophilic carriers |
| CA2474386C (en) | 2002-01-24 | 2011-07-05 | Barnes-Jewish Hospital | Integrin targeted imaging agents |
| US6869591B2 (en) * | 2002-03-26 | 2005-03-22 | Barnes-Jewish Hospital | Paramagnetic particles that provide improved relaxivity |
| AU2005253962A1 (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 delivery of drugs |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3993581A (en) * | 1973-10-05 | 1976-11-23 | The Green Cross Corporation | Process for preparing stable oxygen transferable emulsion |
| JPS5331209B2 (en) * | 1973-10-05 | 1978-09-01 | ||
| US4187252A (en) * | 1977-08-26 | 1980-02-05 | Suntech, Inc. | Tetramethylpentane blood substitutes |
| US4110474A (en) * | 1977-08-26 | 1978-08-29 | Suntech, Inc. | Tetramethylpentane blood substitutes |
| US4186253A (en) * | 1978-10-10 | 1980-01-29 | The Green Cross Corporation | Perfusate for preserving organ to be transplanted and preserving method |
| US4252827A (en) * | 1979-05-23 | 1981-02-24 | The Green Cross Corporation | Oxygen-transferable fluorocarbon emulsion |
| US4647447A (en) * | 1981-07-24 | 1987-03-03 | Schering Aktiengesellschaft | Diagnostic media |
| US4957939A (en) * | 1981-07-24 | 1990-09-18 | Schering Aktiengesellschaft | Sterile pharmaceutical compositions of gadolinium chelates useful enhancing NMR imaging |
| CA1187882A (en) * | 1981-11-27 | 1985-05-28 | Kazumasa Yokoyama | Perfluoro compound and emulsion thereof |
| US4443480A (en) * | 1982-04-12 | 1984-04-17 | Children's Hospital Medical Center | Artificial blood and other gas transport agents |
| US4423077A (en) * | 1982-07-27 | 1983-12-27 | The University Of Pennsylvania | Perfluorochemical emulsion artificial blood |
| US4542147A (en) * | 1982-08-07 | 1985-09-17 | The Green Cross Corporation | Perfluoro-1-azatricyclic amine compound |
| US4534978A (en) * | 1982-12-28 | 1985-08-13 | The Green Cross Corporation | Perfluorocycloamines |
| DE3324235A1 (en) * | 1983-07-01 | 1985-01-10 | Schering AG, 1000 Berlin und 4709 Bergkamen | NEW COMPLEX ILLUMINATORS, COMPLEX AND COMPLEX SALTS |
| CA1257828A (en) * | 1984-04-16 | 1989-07-25 | William Mccormick | Perfluoro compound dispersions containing reduced amounts of surfactant and process of preparation |
| US4859451A (en) * | 1984-10-04 | 1989-08-22 | Salutar, Inc. | Paramagnetic contrast agents for MR imaging |
| US4826673A (en) * | 1985-01-09 | 1989-05-02 | Mallinckrodt, Inc. | Methods and compositions for enhancing magnetic resonance imaging |
| US4686024A (en) * | 1985-02-01 | 1987-08-11 | The Green Cross Corporation | Novel perfluoro chemicals and polyfluorinated compounds and process for production of the same |
| US5399340A (en) * | 1987-09-24 | 1995-03-21 | Schering Aktiengesellschaft | Use of amide complex compounds |
| US5064636A (en) * | 1989-10-19 | 1991-11-12 | Li King C P | Paramagnetic oil emulsions as enteric MRI contrast agents |
| US5120527A (en) * | 1989-10-19 | 1992-06-09 | King Chuen Peter Li | Paramagnetic oil emulsions as mri contrast agents |
| US5154914A (en) * | 1990-03-12 | 1992-10-13 | Research Corporation Technologies, Inc. | Methods of diagnostic image analysis using lipophilic contrast agents |
| US5217706A (en) * | 1990-11-21 | 1993-06-08 | Mallinckrodt Medical, Inc. | Complexes and compositions for magnetic resonance imaging |
| AU660033B2 (en) * | 1991-05-23 | 1995-06-08 | Imarx Pharmaceutical Corp. | Liposoluble compounds for magnetic resonance imaging |
| US5571498A (en) * | 1994-06-02 | 1996-11-05 | Hemagen/Pfc | Emulsions of paramagnetic contrast agents for magnetic resonance imaging (MRI). |
-
1994
- 1994-11-30 US US08/346,885 patent/US5614170A/en not_active Expired - Lifetime
-
1995
- 1995-11-09 AU AU44060/96A patent/AU4406096A/en not_active Abandoned
- 1995-11-09 JP JP8518809A patent/JPH11500413A/en active Pending
- 1995-11-09 EP EP95942846A patent/EP0794801A1/en not_active Withdrawn
- 1995-11-09 WO PCT/US1995/014508 patent/WO1996016679A1/en not_active Application Discontinuation
- 1995-11-09 CA CA002205232A patent/CA2205232A1/en not_active Abandoned
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