Drug – bio-affecting and body treating compositions – In vivo diagnosis or in vivo testing – Magnetic imaging agent
Reexamination Certificate
2007-05-03
2010-10-05
Jones, D L (Department: 1618)
Drug, bio-affecting and body treating compositions
In vivo diagnosis or in vivo testing
Magnetic imaging agent
C424S001110, C424S001530, C424S001650, C424S009100, C424S009360, C534S010000, C534S011000, C534S012000, C534S015000
Reexamination Certificate
active
07807140
ABSTRACT:
Polymeric chelating agents and metal chelates, particularly those of lanthanide metals and more specifically those of Gd(III), useful as contrast agents in magnetic resonance imaging (MRI) for therapeutic and diagnostic applications as well as clinical and biomedical research applications. The polymeric chelates are generated using ring-opening metathesis polymerization (ROMP). Polymers can have multiple sites for functionalization allowing for the synthesis of multimodal and targeted contrast agents. Hydroxypyridonate (HOPO)-based chelating moieties are integrated into a ROMP-derived polymer. More specifically, the HOPO-based chelating moiety is integrated into a benzonorbornadiene unit that constitutes the backbone of the polymer. The ROMP-derived polymer chelators can comprise multiple metal ions, particularly Gd(III) ions, in polymers of varying lengths to provide a series of agents with controlled relaxivites. Polymer chelates include those that are water-soluble.
REFERENCES:
patent: 5756688 (1998-05-01), Snow et al.
patent: 5880231 (1999-03-01), Grubbs et al.
patent: 6271315 (2001-08-01), Kiessling et al.
patent: 6291616 (2001-09-01), Kiessling et al.
patent: 2004/0248801 (2004-12-01), Kiessling et al.
patent: 2005/0008570 (2005-01-01), Raymond et al.
patent: WO 01/71309 (2001-09-01), None
International Search Report, Corresponding to International Application No. PCT/US07/68099, Mailed Sep. 3, 2008.
Written Opinion, Corresponding to International Application No. PCT/US07/68099, Mailed Sep. 3, 2008.
International Preliminary Report on Patentability, International Application No. PCT/US2007/068099, 6 pages, (2007).
Aime et al. (2005) “Gd(III)-Based Contrast Agents for MRI,”Inorg. Chem.57:173-237.
Aime et al. (2001) “Protein-Bound Metal Chelates,” In;The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging, Merbach et al. eds., John Wiley & Sons, Ltd., New York, pp. 193-241.
Allen et al. (2004) “Magnetic Resonance Contrast Agents for Medical and Molecular Imaging,”J. Met. Ions Biol. Syst. 42:1-38.
Allen et al. (2006) “Contrast Agents for Magnetic Resonance Imaging Synthesized with Ring-Opening Metathesis Polymerization,”J. Am. Chem. Soc.128(20):6534-6536.
Anelli et al. (2001) “Synthesis of MRI Contrast Agents I. Acrylic Ligands,” In;The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging, Merbach et al. eds., John Wiley & Sons, Ltd., New York, pp. 121-155.
Brigger et al. (2002) “Nanoparticles in Cancer Therapy and Diagnosis,”Adv, Drug Deliv. Rev.54:631-651.
Caravan et al. (1999) “Gadolinium(III) Chelates as MRI Contrast Agents: Structure, Dynamics, and Applications,”Chem. Rev.99:2293-2352.
Doble et al. ( 2003) “Toward Optimized High-Relaxivity MRI Agebnts: The Effect of Ligand Basicity on the Thermodynamic Stability of Hexadentate Hydroxypyridonate//Catecholate Gadolinium(III) Complexes,”Inorg. Chem.42:4930-4937.
Feutrill et al. (1970) “Demethylation of Aryl Methyl Ethers with Thioethoxide Ion in Dimethyl Formamide,”Tetrahedron Lett.16:1327-1328.
Holmes et al. (1984) “Solution Characterization of Carboxybenzoquinone and the Isolation of Derived Quinhydrones,”J. Org. Chem.49:4736-4738.
Jacques et al. (2001) “Synthesis of MRI Contrast Agents II. Macrocyclic Ligands,” In;The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging, Merbach et al. eds., John Wiley & Sons, Ltd., New York, pp. 157-191.
Love et al. (2002) “A Practical and Highly Active Ruthenium-Based Catalyst that Effects the Cross Metathesis of Acrylonitrile,”Angew Chem. Int Ed.41:4035-4037.
Pierre et al. (2005) “Dendrimeric Gadolinium Chelate with Fast Water Exchange and High Relaxivity at High Magnetic Field Strength,”J. Am. Chem. Soc.127:504-505.
Pontrello et al. (2005) Solid-Phase Synthesis of Polymers Using the Ring-Opening Metathesis PolymerizationJ. Am. Chem. Soc.127:14536-14537.
Raymond et al. (2005) “Next Generation, High Relaxivity Gadolinium MRI Agents,”Bioconjug. Chem. 16:3-8.
Reichert et al. (1999) “Metal Complexes as Diagnostic Tools,”Coord. Chem. Rev. 184:3-66.
Strong et al. (1999) “A General Synthetic Route to Defined, Biologically Active Multivalent Arrays,”J. Am. Chem. Soc.121:6193-6196.
Trnka et al. (2001) “The Development of L2X2Ru=CHR Olefin Metathesis Catalysts: An Organometallic Success Story,”Acc. Chem. Res.34:18-29.
Troth et al. (1999) “Gd(DTPA-bisamide)alkyl Copolymers: A Hint for the Formation of MRI Contrast Agents with Very High Relaxivity,”Chem. Eur. J.5(4):1202-1211.
Tweedle et al. (1999) “Magnetic Resonance Imaging (MRI) Contrast Agents,”Top. Biol. Inorg. Chem. 2:1-43.
Uzgiris et al. (2004) “Conformation and Structure of Polymeric Contrast Agents for Medicinal Imagin,”Biomacromolecules5:54-61.
Xu et al. (2004) “Gadolinium(III) 1,2-Hydroxypyridonate-Based Complexes: Toward MRI Contrast Agents of High Relaxivity,”Inorg. Chem. 43:5492-5494.
Xu et al. (1995) “Gadolinium Complex of Tris[(3-hydroxyl-1-methyl-2-oxo-1,2-didehydropyridine-4-carboxamido)ethyl]-amine: A New Class of Gadolinium Magnetic Resonance Relaxation Agents,”J. Am. Chem. Soc. 117:7245-7246.
Allen Matthew J.
Kiessling Laura L.
Raines Ronald T.
Greenlee Sullivan P.C.
Jones D L
Wisconsin Alumni Research Foundation
LandOfFree
Magnetic resonance imaging contrast agents synthesized using... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Magnetic resonance imaging contrast agents synthesized using..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Magnetic resonance imaging contrast agents synthesized using... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4167515