Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1995-05-16
1997-03-11
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
540465, C07D25900, C07D25700
Patent
active
056102933
ABSTRACT:
The present invention is directed to low molecular weight mimics of superoxide dismutase (SOD) represented by the formula: ##STR1## wherein R, R', R.sub.1, R'.sub.1, R.sub.2, R'.sub.2, R.sub.3, R'.sub.3, R.sub.4, R'.sub.4, R.sub.5, R'.sub.5, R.sub.6, R'.sub.6, R.sub.7, R'.sub.7, R.sub.8, R'.sub.8, R.sub.9, and R'.sub.9 and X, Y, Z and n are as defined herein, useful as therapeutic agents for inflammatory disease states and disorders, ischemic/reperfusion injury, stroke, atherosclerosis, hypertension and all other conditions of oxidant-induced tissue damage or injury.
REFERENCES:
patent: 3930867 (1976-01-01), Bigelow
patent: 4001212 (1977-01-01), Richman
patent: 4702998 (1987-10-01), Tanaka et al.
patent: 4885363 (1989-12-01), Tweedle et al.
patent: 5049667 (1991-09-01), Schaefer et al.
patent: 5096724 (1992-03-01), Zenner et al.
patent: 5247077 (1993-09-01), Parker et al.
patent: 5274147 (1993-12-01), Kersehner et al.
patent: 5326861 (1994-07-01), Madison et al.
Bradshaw et al. J. Heterocyclic. Chem., 26, pp. 1431-1435., 1989.
McCord, Free Radicals Biol. Med. 2, 307 (1986).
Bannister et al., Crit. Rev. Biochem., 22, 111 (1987).
Newton et al., J. Coord. Chem. 17 pp. 265-277 1988.
Petkau Cancer Treatment Review 1986 13 17-44.
Newton, J.E. et al., Synthesis and Characterization of the Mn(II) Complex of [15]aneN.sub.5, J. Coord. Chem., vol. 19, pp. 265-277 (1988).
Weiss, R. H. et al., Catalytic Efficacies of Agents that Dismutate Superoxide, J. Cell. Biochem., Suppl. 15C,216, abstract CC110 (1991).
Petkau, A., Scientific Basis for the Clinical Use of Superoxide Dismutase, Cancer Treat. Rev., vol. 13, pp. 17-44 (1986).
McCord, J. M. Superoxide Dismutase: Rationale for Use in Reperfusion Injury and Inflammation, J. Free Radicals Biol. Med., vol. 2, pp. 307-310 (1986).
Bannister, J.V.et al., Aspects of the Structure, Function, and Applications of Superoxide Dismutase, CRC Crit. Rev. Biochem. vol. 22, pp. 111-180 (1987).
Richman, J.E. et al., Nitrogen Analogs of Crown Ethers, J. Am. Chem. Soc. vol. 96, pp. 2268-2270 (1974).
Atkins, T.J. et al., Macrocyclic Polyamines: 1,4,7,10,13,16-Hexaazacyclo-octadecane, Org. Synth., vol. 58, pp. 86-98 (1978).
Riley, D.P. et al., Stopped-Flow Kinetic Analysis for Moinitoring Superoxide Decay in Aqueous Systems, Anal. Biochem., vol. 196, pp. 344-349 (1991).
Bull, C. et al., The Mechanism of Fe-EDTA Catalyzed Superoxide Dismutation, J. Am. Chem. Soc., vol. 105, pp. 5290-5300 (1983).
Kimura, E. et al., Further Studies on Superoxide Dismutase Activities of Macrocyclic Polyamine Complexes of Copper (II), Biochim. Biophys. Acta, vol. 745, pp. 37-43 (1983).
Kimura, E. et al., Superoxide Dismutase Activity of Macrocyclic Polyamine Complexes, Biochim. Biophys. Acta, vol. 678, pp. 172-179 (1981).
Rush, J. D. et al., The Superoxide Dismutase Activities of Two Higher-Valent Manganese Compl4exes, Mn.sup.IV Desferrioxamine and Mn.sup.III Cyclam, Arch. Biochem. Biophys., vol. 289, pp. 1-6 (1991).
Fretland, D.J. et al., Superoxide Dismutase (SOD) Modulates Acetic Acid-Induced Colitis in Rodents, Gastroenterology, vol. 100, p. A581 (1990).
Gryglewski, R. J. et al., Superoxide Anion is Involved in the Breakdown of Endothelium-Derived Vascular Relaxing Factor, Nature, vol. 320, pp. 454-456 (1986).
Alexander, M.D., Manganese (II) Complexes of a Macrocyclic Ligand, Inorg. Nucl. Chem. Letters, vol. 6, pp. 445-448 (1970).
Brady, S.F. et al., Practical Synthesis of Cyclic Peptides, with an Example of Dependence of Cyclization Yield upon Linear Sequence, J. Org. Chem., vol. 44, pp. 3101-3105 (1979).
Tabushi, I. et al., Preparation of C-Alkylated Macrocyclic Polyamines, Tetrahedron Letters, No. 12, pp. 1049-1052 (1977).
Fujioka, H. et al., The Effects of Size and Donor Atoms of Macrocyclic Polyamines Binding to Mg.sup.2+ and Ca.sup.2+, Chem .Letters., pp. 737-740 (1982).
Krakowiak, K.E. et al., Preparation of Triaza-, Tetraaza- and Peraza-Crown Compounds Containing Aminoalkyl Side Groups or Unsubstituted Ring Nitrogen Atoms, J. Org. Chem., vol. 55, pp. 3364-3368 (1990).
Bradshaw, J.S. et al., A Simple Crab-Like Cyclization Procedure to Prepare Polyaza-Crowns and cyclams With One or Two Unsubstituted Macroring Nitrogen Atoms or With a Hydroxy Group, J. Heterocyclic Chem., vol. 26, pp. 1431-1435 (1989).
Krakowiak, K.E. et al., Novel Syntheses of Monofunctionalized Triaza-Crowns and Cyclams With a Secondary Amine Group on a Side Chain, Tetrahedron Letters, vol. 30, No. 22, pp. 2897-2900 (1989).
Krakowiak, K.E. et al., Preparation and Structural Properties of Large-Cavity Peraza Macrocycles Containing Pyridine, Phenanthroline, or Piperazine Subcyclic Units, J. Org. Chem., vol. 56, pp. 2675-2890 (1991).
Rush Archives of Biochem and Biophys. 289(1) pp. 1-6 1991.
Kimura et al. Biochimica et Biophysica Acta 678 (1981) 172-179.
Kimura et al. Biochimica et Biophysica Acta 1983 37-43
Bell et al. JACS 1983 105 5290-5300.
Riley et al. Analytical Biochem. 196 344-349 1991.
Newton, et al. Chemical Abstracts, vol. 110 1989 AB 146606P.
Krakowiak, J. Org Chem. 1990 3364-3367.
Gryglewski et al. Nature vol. 320 1986 pp. 454-456.
Alexander et al. Inorg. Nucl. Chem Letters vol. 6 pp. 445-448, 1976.
Brady, et al. J. Org Chem. 44(18) 1979 pp.3101-3105.
Tabushi et al. Tetrahedron Letters 12 pp. 1049-1052, 1111.
Fujioka Chemistry Letters pp. 737-740 1982.
Atkins, et al Org Synth. vol. 58 pp. 344-341 1978.
Richman et al. JACS vol. 96 1974 pp. 2268-2270.
Krakowiak et al. Tetrahedron Letters 30(22) pp. 2897-2900 1989.
Bradshaw et al. J Heterocyclic Chem 26 1431 (1989).
Jackels, et al. Inorg. Chem. 1992 31 234-239.
Bencini et al. Inorg. Chem. 1990 29 1716-1718.
Fretland et al., Gastroenterology, 100, A581 (1990).
Akaike et al. J. Clin. Invest. 85, 1996 739-745.
Trenam J. of Dermatology (1991) 125 325-329.
Cremer et al J of Heart Transplantation Aug. 1989 pp.330-335.
Michelson Life Chemistry Reviews 1987 6 1-142.
Bando et al. J Heart Lung Transplant 10(2) 1991 pp. 304-307.
Marklund Adv Clin Enzymol. 135-144, 1986.
Oberley, Free Radical Biology and Medicine 5 pp. 113-124. 1988.
Storhoff et al. Coord. Chem. Rev 23 (1977) 1-29.
Wisner et al. Gut 1988 29 1516-1523.
Lindoy, L. F., The Chemistry of Macrocyclic Ligand Complexes, Cambridge University Press, pp. 16-17 and 40-43 (1989).
Jackels, S.C. et al., "Agueous Proton NMR Relaxation Enhancement by Manganese (II) Macrocyclic Complexes: Structure-Relaxivity Relationships", Inorg. Chem., 31, 234-239 (1992).
Aston Karl W.
Lennon Patrick J.
Modak Anil S.
Neuman William L.
Riley Dennis P.
Monsanto Company
Shah Mukund J.
Sripada Pavanaram K.
LandOfFree
Methods of preparing manganese complexes of nitrogen-containing does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Methods of preparing manganese complexes of nitrogen-containing , we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Methods of preparing manganese complexes of nitrogen-containing will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-444638