Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1994-05-27
1995-06-27
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
540470, C07D25700, C07D25900
Patent
active
054281555
ABSTRACT:
The pH controlled selectivity of the sulfomethylation reaction is used to prepare a series of di-, tri-, tetra- and hexaazacyclomacrocycles with specified patterns of pendent side-chain chelating groups. The prepared mono and diacetic acid derivatives, together with monomethylenephosphonate and monomethylenephosphinate derivatives of [12]aneN4, [12]aneN3 and [9]aneN3, make these types of ligands easily available by a synthetic pathway that avoids the use of protective groups. The invention thus comprises a variety of compounds, methods and uses characterized by relatively high synthetic yields of polyazamacrocyclic ligands exhibiting a wide and predictable choice of metal ion binding constants water and lipid solubilities by reason of their substituent pendent groups.
REFERENCES:
patent: 3930867 (1976-01-01), Bigelow
patent: 3932451 (1976-01-01), Bigelow
patent: 3987128 (1976-10-01), Richman
patent: 3996276 (1976-12-01), Atkins
patent: 4038312 (1977-07-01), Atkins
patent: 4085106 (1978-04-01), Atkins
patent: 4130715 (1978-12-01), Atkins
patent: 4337154 (1982-06-01), Fukuchi
patent: 4352751 (1982-10-01), Wieder
patent: 4421671 (1983-12-01), Cusano
patent: 4432907 (1984-02-01), Wieder
patent: 4472509 (1984-09-01), Gansow
patent: 4639365 (1987-01-01), Sherry
patent: 4647447 (1987-03-01), Gries et al.
patent: 4731239 (1988-03-01), Gordon
patent: 4735796 (1988-04-01), Gordon
patent: 4889931 (1989-12-01), Rocklage et al.
patent: 4957939 (1990-09-01), Gries et al.
patent: 4963344 (1990-10-01), Gries et al.
patent: 4983376 (1991-01-01), Sherry
Cabbiness et al., "Macrocyclic Effect on the Stability of Copper(II) Tetramine Complexes", J. Am. Chem. Soc., 91(23):6540 (1969), published in USA.
Martin et al., "The Relationship between Metal-Donor Distance and Ring Size in Macrocyclic Complexes", J. Am. Chem. Soc., 96(12):4046 (1974), published in USA.
Richman et al., "Nitrogen Analogs of Crown Ethers", J. Am. Chem. Soc., 96(7):2268-70 (1974), published in USA.
Lettvin et al., "Communications: Gd(TTHA): An Aqueous Carbon-13 Relaxation Reagent," J. Mag. Res., 28:459-61 (1977), published in Europe.
White et al., "A Tris(dialkylamino)phosphine with Pyramidal Nitrogens," J. Amer. Chem. Soc., 101(17):4921 (1979), published in USA.
Desreux, "Nuclear Magnetic Resonance Spectroscopy of Lanthanide Complexes with a Tetraacetic Macrocycle. Unusual Conformation Properties," Inorganic Chemistry, 19:1319-24 (1980), published in USA.
Sherry, "A Proposal on Basic Chemical Research," submitted to the Robert A. Welch Foundation (1981), printed in USA.
Bryden et al., "Multinuclear NMR Study of Three Aqueous Lanthanide Shift Reagents: Complexes with EDTA and Two Macrocyclic Ligands," Chemical Abstracts, No. 97:206960z (1982), published in USA.
Desreux, letter dated Dec. 23, 1983 to Sherry, printed in Belgium.
Brasch et al., "Contrast-Enhanced NMR Imaging: Animal Studies Using Gadolinium-DTPA Complex,"American Journal of Roentgenology, 142:625-30 (1984), published in USA.
Chen et al., "Paramagnetic Metalloporphyrins as Potential Contrast Agents in NMR Imaging," Fed. Euro. Biochem. Soc., 168(1):70 (1984), published in Europe.
Goldstein et al., "Gadolinium DTPA (An NMR Proton Imaging Contrast Agent): Chemical Structure, Paramagnetic Properties and Pharmacokinetics," Physiol. Chem. & Phys. & Med. NMR, 16:97-104 (1984), published in USA.
Sherry, letter dated Apr. 4, 1984 to Schmidt, printed in USA.
Weinmann et al., "Characteristics of Gadolinium-DTPA Complex: A Potential NMR Contrast Agent," American Journal of Roentgenology, 142:619-24 (1984), printed in USA.
Wolf, "Contrast Enhancement in Biomedical NMR," Physiol. Chem. & Phys. & Med. NMR, 16:93-95 (1984), printed in USA.
Geraldes et al., "Nuclear Magnetic Resonance and Potentiometric Studies of the Protonation Scheme of a Triaza Triacetic Macrocycle and Its Complexes with Lanthanum and Lutetium," Inorganic Chemistry, 24(23):3876 (1985), printed in USA.
Geraldes et al., "Lanthanum-139 Nuclear Magnetic Resonance Studies of Polyaminocarboxylate-Lanthanum Complexes in Aqueous Solution," Journal of Magnetic Resonance, 66:274-82 (1986), published in USA.
Geraldes et al., "Magnetic Field Dependence of Solvent Proton Relaxation Rates Induced by Gd.sup.3+ and Mn.sup.2+ Complexes of Various Polyaza Macrocyclic Ligands: Implications for NMR Imaging," Magnetic Resonance in Medicine, 3:242-50 (1986), published in USA.
Sherry et al., "Nuclear Magnetic Resonance Structural Studies of an Axially Symmetric Lanthanide Ion Chelate in Aqueous Solution," Journal of Magnetic Resonance, 66:511-24 (1986), published in USA.
Chavez et al., "A Simplified Synthetic Route to Polyaza Macrocycles," J. Org. Chem, 54(12):2990-92 (1989), published in USA.
Sherry, "Lanthanide Chelates as Magnetic Resonance Imaging Contrast Agents," J. Less Common Metals, 149:133-41 (1989).
The Chemical Abstracts citation of European Patent Application EP 382,582, 16 Aug. 1990 to Parker et al.
Sherry A. Dean
Van Westrenen Jeroen
Board of Regents , The University of Texas System
Shah Mukund J.
Sripada Pavanaram K.
LandOfFree
Synthesis of polyazamacrocycles with more than one type of side- does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Synthesis of polyazamacrocycles with more than one type of side-, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of polyazamacrocycles with more than one type of side- will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-288595