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Novel nitric oxide synthase inhibitors: a patent review

, BPharm MSc & , BPharm MSc PhD
Pages 537-560 | Published online: 22 Feb 2011

Bibliography

  • Thomas DD, Ridnour LA, Isenberg JS, The chemical biology of nitric oxide: implications in cellular signaling. Free Radical Biol Med 2008;45(1):18-31
  • Moncada S, Palmer RM, Higgs EA. Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol Rev 1991;21(2):109-42
  • Martin IN, Woodward JJ, Winter MB, Design and synthesis of C5 Methylated L-arginine analogues as active site probes for nitric oxide synthase. J Am Chem Soc 2007;129:12563-70
  • Dawson VL, Dawson TM, Lomdon ED, Nitric oxide mediates glutamate neurotoxicicty in primary cortical cultures. Proc Natl Acad Sci 1991;88:6368-71
  • Kerwin JF, Lancaster JR, Feldamn PL. Nitric oxide: a new paradigm for second messengers. J Med Chem 1995;38:4343-62
  • Knowles RG, Moncada S. Nitric oxide synthases in mammals. Biochem J 1994;298(2):249-58
  • Cary SPL, Winger JA, Derbyshire ER, Nitric oxide signaling: no longer simply on or off. Trends Biochem Sci 2006;31(4):231-9
  • Hoffman BB, Taylor P. Goodman and gilman's. The pharmacological basis of therapeutics. Chapter 6: Neurotransmission. McGraw-Hill, New York; 2001. p. 148
  • Roman LJ, Mattasek P, Masters BSS. Intrinsic and extrinsic modulation of nitric oxide synthase activity. Chem Rev 2002;102:1179-89
  • Marletta MA. Nitric oxide synthase structure and mechanism. J Biol Chem 1993;268:12231-4
  • Steur DJ. Mammalian nitric oxide synthase. Biochemica et Biophysica Acta (BBA) Bioenergetics 1999;1411:217-30
  • Alderton WK, Cooper CE, Knowles RG. Nitric oxide synthases: structure function and inhibition. Biochem J 2001;357:593-615
  • Knowles RG, Palacios M, Palmer MRJ, Formation of nitric oxide from L-Arginine in the central nervous system: a transduction mechanism for stimulation of the soluble guanylate cyclase. Proc Natl Acad Sci 1989;86:5159-62
  • Uehara T, Nakamura T, Yao D, S-Nitrosylated protein-disulphide isomerase links protein misfolding to neurodegeneration. Nature 2006;441(7092):513-17
  • Kim SF, Huri DA, Snyder SH. Inducible nitric oxide synthase binds, S-nitrosylates, and activates cyclooxygenase-2. Science 2005;310(5756):1966-70
  • Rosen GM, Tsai P, Pou S. Mechanism of free-radical generation by nitric oxide synthase. Chem Rev 2002;102(1):191-200
  • Wang Y, Newton DC, Robb GB, RNA diversity has profound effects on the translation of neuronal nitric oxide synthase. Proc Natl Acad Sci USA 1999;96:12150-5
  • Brenman JE, Chao DS, Gee SH, Interaction of nitric oxide synthase with the postsynaptic density protein PSD-95 and alpha1-syntrophin mediated by PDZ domains. Cell 1996;84:757-67
  • Silvagno F, Xia H, Bredt DS. Neuronal nitric-oxide synthase-mu, an alternatively spliced isoform expressed in differentiated skeletal muscle. J Biol Chem 1996;271:11204-8
  • Magee T, Fuentes AM, Garban H, Cloning of a novel neuronal nitric oxide synthase expressed in penis and lower urinary tract. Biochem Biophys Res Commun 1996;226:145-51
  • Ogura T, Yokoyama T, Fujisawa, Structural diversity of neuronal nitric oxide synthase mRNA in the nervous system. Biochem Biophys Res Commun 1993;193:1017-22
  • Fujisawa H, Ogura T, Kurashima Y, Expression of two types of nitric oxide synthase mRNA in human neuroblastoma cell lines. J Neurochem 1994;63:140-5
  • Brenman JE, Xia H, Chao DS, Regulation of neuronal nitric oxide synthase through alternative transcripts. Dev Neurosci 1997;19:224-31
  • Kolesnikov YA, Pan YX, Babey AM, Functionally differentiating two neuronal nitric oxide synthase isoforms through antisense mapping: evidence for opposing NO actions on morphine analgesia and tolerance. Proc Natl Acad Sci USA 1997;94:8220-5
  • Eliasson MJ, Blackshaw S, Schell MJ, Neuronal nitric oxide synthase alternatively spliced forms: prominent functional localizations in the brain. Proc Natl Acad Sci USA 1997;97:3396-401
  • Hemmens B, Woschitz S, Pitters E, The protein inhibitor of neuronal nitric oxide synthase: characterization of its action on pure nitric oxide synthases. FEBS Lett 1998;430:397-400
  • Christopherson KS, Hillier BJ, Lim WA, PSD-95 assembles a ternary complex with the N-methyl-d-aspartic acid receptor and a bivalent neuronal NO synthase PDZ domain. J Biol Chem 1999;274:27467-73
  • Boughton SNK, Tinker AC. Inhibitors of nitric oxide synthase in inflammatory arthritis. IDrugs 1998;1:321-33
  • Endres M, Laufs U, Liao JK, Targeting eNOS for stroke protection. Trends Neurosci 2004;27(5):283-9
  • Braam B, Verhaar MC. Understanding eNOS for pharmacological modulation of endothelial function: a translational view. Curr Pharm 2007;13(17):1727-40
  • Larson AA, Kovacs KJ, Cooper JC, Transient changes in the synthesis of nitric oxide result in long-term as well as short-term changes in acetic acid-induced writhing in mice. Pain 2000;86:103-11
  • Tafi A, Angeli L, Venturini G, Computational studies of competitive inhibitors of nitric oxide synthase (NOS) enzymes: towards the development of powerful and isoform-selective inhibitors. Curr Med Chem 2006;13(16):1929-46
  • Salerno L, Sorrenti V, Di Giacomo C, Progress in the development of selective nitric oxide synthase (NOS) inhibitors. Curr Pharm Des 2002;8(3):177-200
  • Vallance P, Leiper J. Blocking nO synthesis: how, where and why? Nat Rev Drug Discov 2002;1(12):939-50
  • Muscara MN, Wallace JL. Nitric oxide V. Therapeutic potential of nitric oxide donors and inhibitors. Am J Physiol 1999;276:1313-16
  • Ogden JE, Moore PK. Inhibition of nitric oxide synthase-potential for a novel class of therapeutic agent. Trends Biotech 1995;13:70-8
  • Griffith OW, Kilbourn RG. Nitric oxide synthase inhibitors: amino acids. Methods Enzymol 1996;268:375-92
  • Southan GJ, Szabo C. Selective pharmacological inhibition of distinct nitric oxide synthase isoforms. Biochem Pharmacol 1996;51(4):383-94
  • Wilcock DM, Lewis MR, Van Nostrand WE, Progression of amyloid pathology to Alzheimer's disease pathology in an amyloid precursor protein transgenic mouse model by removal of nitric oxide synthase 2. J Neurosci 2008;28(7):1537-45
  • Babbedge RC, Bland-Ward PA, Hart SL, Inhibition of rat cerebellar nitric oxide synthase by 7-nitro indazole and related substituted indazoles. Br J Pharmacol 1993;1(10):225-8
  • Babu BR, Griffith OW. Design of the isoform-selective inhibitors of nitric oxide synthase. Curr Opin Chem Biol 1998;2:491-500
  • Pekiner C, Kelicen P, Uma S, Two nitric oxide synthase inhibitors: pyridoxal aminoguanidine and 8-quinolinecarboxylic hydrazide selectively inhibit basal but not agonist stimulated release of nitric oxide in rat aorta. Pharmacol Res 2002;46:317-20
  • Handy RLC, Wallace P, Gaffen ZA, The antinociceptive effect of 1-(2-trifluoromethylphenyl) imidazole (TRIM), a potent inhibitor of neuronal nitric oxide synthase in vitro, in the mouse. Br J Pharmacol 1995;116:2349-50
  • Zhang ZG, Reif D, MacDonald WX, ARL 17477, a potent and selective neuronal NOS inhibitor decreases infarct volume after transient middle cerebral artery occlusion in rats. J Cereb Blood Flow Metab 1996;16:599-604
  • Neuraxon, Inc. Substituted indole compounds having NOS inhibitory activity. US20060258721; 2006
  • Neuraxon, Inc. Substituted indole compounds having NOS inhibitory activity. WO2007063418; 2007
  • Neuraxon, Inc. 1,5 and 3,6-substituted indole compounds having NOS inhibitory activity. WO2007118314; 2007
  • Neuraxon, Inc. 3,5-Substituted indole compounds having NOS and norepinephrine reuptake inhibitory activity. WO2009062318; 2009
  • Neuraxon, Inc. Indole compounds and methods for treating visceral pain. WO2009062319; 2009
  • Hevel JM, Marletta MA. Nitric oxide synthase assays. Methods Enzymol 1994;133:250-8
  • Neuraxon, Inc. Substituted benzimidazole compounds with dual NOS inhibitory activity and mu-opoid agonist activity. WO2007017764; 2007
  • Neuraxon, Inc. Quinolone and tetrahydroquinolone and related compounds having NOS inhibitory activity. US20080234237; 2008
  • Neuraxon, Inc. Benzoxazines, benzothiazines, and related compounds having NOS inhibitory activity. WO2010000073; 2010
  • Northwestern University. Heteroaromatic selective inhibitors of neuronal nitric oxide synthase. WO20050107369; 2005
  • Northwestern University. Heteroaromatic selective inhibitors of neuronal nitric oxide synthase. WO2005026111; 2005
  • NOS inhibitors for the treatment of motor deficit disorders. WO2008036294; 2008
  • North Western University. Potent and highly selective heteroaromatic inhibitors of neuronal nitric oxide synthase. US20080108814; 2008
  • Ji H, Li H, Martasek P, Discovery of Highly Potent and Selective Inhibitors of Neuronal Nitric Oxide Synthase by Fragment Hopping. J Med Chem 2009;52:779-97
  • Lawton GR, Ranaivo HR, Chic LK, Analogues of 2-aminopyridine-based selective inhibitors of neuronal nitric oxide synthase with increased bioavailability. Bioorg Med Chem 2009;17:2371-80
  • Xue F, Fang J, Lewis WW, Potent and selective neuronal nitric oxide synthase inhibitors with improved cellular permeability. Bioorg Med Chem 2010;20:544-57
  • Northwestern University. Potent and selective neuronal nitric oxide synthase inhibitors with improved membrane permeability. US201001902320; 2010
  • Northwestern University. Aminopyridine dimer compounds, compositions and related methods for neuronal nitric oxide synthase inhibition. US20100203613; 2010
  • Haung H, Martasek P, Roman LJ, N-nitroarginine-containing dipeptide amides. Potent and highly selective inhibitors of neuronal nitric oxide synthase. J Med Chem 1999;42:3147-53
  • Northwestern University. Selective neuronal nitric oxide synthase inhibitors. US20030119751; 2003
  • Northwestern University. NOS inhibitors for treatment of motor deficit disorders. WO2008036294; 2008
  • Northwestern University. Selective neuronal nitric oxide synthase inhibitors. US7470815: 2008
  • Hah JM, Roman LJ, Martasek P, Reduced amide bond isosteric peptidomimetics. (4S)-N-(4-Amino-5-[aminoalkyl]aminopentyl)-N′-nitroguanidines, potent and highly selective inhibitors of neuronal nitric oxide synthase. J Med Chem 2001;44:2667-70
  • Hah JM, Martasek P, Roman LJ, Aromatic reduced amide bond peptidomimetics as selective inhibitors of neuronal nitric oxide synthase. J Med Chem 2003;46:1661-9
  • Schmidt HH, Walter U. NO at work. Cell 1994;78:919-25
  • Titheradge MA. Nitric oxide in septic shock. Biochim Biophys Acta 1991;1411:437-55
  • Hobbs AJ, Higgs A, Moncada S. Inhibition of nitric oxide synthase as a potential therapeutic target. Annu Rev Pharmacol Toxicol 1999;39:191-220
  • Mete A, Connolly S. Inhibitors of the NOS enzymes: a patent review. IDrugs 2003;6:57-65
  • Moncada S, Higgs EA. Molecular mechanisms and therapeutic strategies related to nitric oxide. FASEB J 1995;9:1319-30
  • Garvey EP, Oplinger JA, Furfine ES, 1400W is a slow, tight binding and highly selective inhibitor of inducible nitric-oxide synthase in vitro and in vivo. J Biol Chem 1997;272:4959-63
  • Young RJ, Beams RM, Carter K, Inhibition of inducible nitric oxide synthase by acetamidine derivatives of hetero-substituted lysine and homolysine. Bioorg Med Chem Lett 2000;10:597-600
  • Alderton WK, Angell AD, Craig C, GW274150 and GW273629 are potent and highly selective inhibitors of inducible nitric oxide synthase in vitro and in vivo. Br J Pharmacol 2005;145:301-12
  • Beaton H, Hamley P, Nicholls DJ, 3,4-Dihydro-1-isoquinolinamines: a novel class of nitric oxide synthase inhibitors with a range of isoform selectivity and potency. Bioorg Med Chem Lett 2001;11:1023-6
  • Tinker AC, Beaton HG, Boughton-Smith N, 1,2-Dihydro-4-quinazolinamines: potent, highly selective inhibitors of inducible nitric oxide synthase which show anti-inflammatory activity in vivo. J Med Chem 2003;46:913-16
  • Nishina K, Mikawa K, Kodoma S, ONO1714, a new inducible nitric oxide synthase inhibitor, attenuates sepsis-induced diaphragmatic dysfunction in hamsters. Anesth Analg 2001;92:959-66
  • Hansel RT, Kharitonov SA, Donnelly LE, A selective inhibitor of inducible nitric oxide synthase inhibits exhaled breath nitric oxide in healthy volunteers and asthmatics. FASEB J 2003;16:1298-300
  • Habisch HJ, Gorren AC, Liang H, Pharmacological interference with dimerization of human neuronal nitric-oxide synthase expressed in adenovirus-infected DLD-1 cells. Mol Pharmacol 2003;63:682-9
  • Altana Pharma AG. Imidazo(4,5-B)pyridine-derivatives as inducible NO-synthase inhibitors. WO2005030768; 2005
  • Altana Pharma AG. Imidazopyridine-derivatives as inducible NO-synthase inhibitors. WO2005030770; 2005
  • Altana Pharma AG. Imidazolyl-substituted azabenzophenone compounds. WO2007039578; 2007
  • Altana Pharma AG. Imidazole-substituted benzophenone compounds. WO2007039580; 2007
  • Altana Pharma AG. Imidazolyl-substituted diazabenzophenone compounds. WO2007039581; 2007
  • Altana Pharma AG. Oxazolo[4,5-B]pyridine compounds as nitric oxide synthase inhibitors. WO2007045622; 2007
  • Altana Pharma AG. Imidazopyridine-derivatives as inducible NO-synthase inhibitors. WO2005030769; 2005
  • Altana Pharma AG. Imidazopyridine-derivatives as inducible NO-synthase inhibitors. WO2005030771; 2005
  • Altana Pharma AG. Alkoxypyridine-derivatives. US7138399; 2006
  • Altana Pharma AG. Imidazopyridine-derivatives as inducible NO-synthase inhibitors. US20090036482; 2009
  • Altana Pharma AG. Aminopyridine-derivatives. US7781453; 2010
  • Aventis Pharmaceuticals, Inc. Coumarins as iNOS inhibitors. WO2005026143; 2005
  • Aventis Pharmaceutical, Inc. Coumarins as iNOS inhibitors. US7538233; 2009
  • Bredt DS, Snyder SH. Isolation of nitric oxide synthase, a calmodulin-requiring enzyme. Proc Natl Acad Sci 1990;87:682-5
  • Nycomed GMBH. Aminoazepine derivatives as highly efficient inhibitors of the inducible nitric oxide synthase. WO2008031788; 2008
  • Nycomed GMBH. Imidazopyridine derivatives useful as iNOS inhibitors. US7790710; 2010
  • Schering. N-heterocyclic derivatives as NOS inhibitors. US20060094725; 2006
  • Schering. 1-(Pyridazin-3-yl)-imidazole derivatives as inhibitors of nitric oxide synthase (NOS). US7202263; 2007
  • Berlex Laboratories, Inc. N-Heterocyclic derivatives as NOS inhibitors. WO0114371; 2003
  • Berlex Laboratories, Inc. N-Heterocyclic derivatives as NOS inhibitors. WO0114371; 2005
  • Berlex Laboratories, Inc. N-Heterocyclic derivatives as NOS inhibitors. US6841674; 2005
  • Damiani P, Burini G. Fluorometric determination of nitrite. Talanta 1986;33:649-52
  • Seoul national university foundation. Pharmaceutical composition, health food composition and iNOS inhibitors, containing theopederin derivatives. WO2008072937; 2007
  • Pharmacia Corp. Amidino compounds useful as nitric oxide synthase inhibitors. US6914158; 2004
  • Pharmacia Corp. 2-Amino-2-alkyl-4 hexenoic and hexynoic acid derivatives useful as nitric oxide synthase inhibitors. US20050256199; 2005
  • Pharmacia Corp. Combination therapy with inhibitors of inducible nitric oxide and alkylating agents. WO2005025620; 2005
  • Pharmacia Corp. Amidino compounds useful as nitric oxide synthase inhibitors. US7196118; 2007
  • Pharmacia Corp. 2-Amino-2-alkyl-5 heptenoic and heptynoic acid derivatives. WO2007203823; 2007
  • Erba Carlo Spa. New aryl- and heteroarylathenylene derivatives and process for their preparation. WO1991013055; 1991
  • Searle & CO; Currie Mark G. Amidino derivatives useful as nitric oxide synthase inhibitors. WO1995025717; 1995
  • Carre MC, Mahieuxe JC, Andre JC, Fluorometric nitrate analysis using 2,3-diaminonaphthalene: an improvement of the method. Analusis 1999;27:835-8
  • Kalypsys Incorporation. Inducible nitric oxide synthase dimerization inhibitors. US20060116515; 2006
  • Kalypsys Incorporation. Inducible nitric oxide synthase dimerization inhibitors. US2006060424; 2006
  • Kalypsys Incorporation. Salts of inducible nitric oxide synthase dimerization inhibitors. US20070197609; 2007
  • Kalypsys Incorporation. Imidazole derivatives as nitric oxide synthase dimerization inhibitor. WO2007062410; 2007
  • Kalypsys Incorporation. Methods of preparing 2-imidazol-1-yl-4-methyl-6-pyrrolidin-2-yl-pyrimidine and 4-(1-alkylpyrrolodin-2-yl)-2-(1H-imidazol-1-yl)-6methylpyrimidine derivatives. US20080293942; 2008
  • Kalypsys Incorporation. Quinolones useful as inducible nitric oxide synthase inhibitors. WO2007117778; 2007
  • Kalypsys Incorporation. Isoquinolines useful as inducible nitric oxide synthase inhibitors. WO2008103615; 2008
  • Kalypsys Incorporation. Topical pharmaceutical formulation comprising an iNOS inhibitor for the treatment of disease. WO2008086176; 2008
  • Kalypsys Incorporation. 4-[heterocyclyl-methyl]-8-fluoro-quinolin-2-ones useful as nitric oxide synthase inhibitors. WO2009029625; 2009
  • Kalypsys Incorporation. Diarylamine-substituted quinolones useful as inducible nitric oxide synthase inhibitors. WO2009029617; 2009
  • Kalypsys Incorporation. Heterobicyclic-substituted quinolones useful as nitric oxide synthase inhibitors. WO2009029595; 2009
  • Luvone T, D'Acquisto F, Van Osselaer N, Evidence that inducible nitric oxide synthase is involved in LPS-induced plasma leakage in rat skin through the activation of nuclear factor-kappaB. Br J Pharmacol 1998;123:1325-30
  • Kalypsys Incorporation. Treatment of inflammation and related disorders by activation of the unfolded protein response. WO2007084868; 2007
  • Kalypsys Incorporation. Novel 2-oxo-1,2,3,4-tetrahydropyrimidines, bicyclic pyrimidine diones and imidazolidine-2,4-diones useful as inducible nitric oxide synthase inhibitors. WO2007101213; 2007
  • Pfizer, Inc. S-[2[(1-Iminoethyl)amino]ethyl]-2-methyl-L-cysteine maleate hydrochloride crystalline salt. US7767850; 2010
  • Pharmacia Corporation. Amidino compounds and salts thereof useful as nitric oxide synthase inhibitors. US6403830; 2002
  • AstraZeneca. Anti-inflammatory 3-Aryl-3-thiazolyl-alkylamines. WO2004041794; 2004
  • AstraZeneca. Novel compounds. WO2004009580; 2004
  • AstraZeneca. Heteroarylheteroallkylamine derivatives and their use as inhibitors of nitric oxide synthase. WO03011831; 2004
  • AstraZeneca. Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase. WO03011210; 2005
  • AstraZeneca. Compounds for the inhibition of nitric oxide synthase. US7276528; 2007
  • AstraZeneca. Substituted thiophene compounds. US7329686; 2008
  • Forstermann U, Schmidt HHHW, Kohlhaas KL, Induced RAW 264.7 macrophages express soluble and particulate nitric oxide synthase: inhibition by transforming growth factor-beta. Eur J Pharm 1992;225:161-5
  • Ignarro LJ. Nitric oxide as a unique signaling molecule in the vascular system: a historical overview. J Physiol Pharmacol 2002;53:503-14
  • Bonetti PO, Lerman LO, Lerman A. Endothelial dysfunction: a marker of atherosclerotic risk. Arterioscler Thromb Vasc Biol 2003;23:168-75
  • Heitzer T, Schlinzig T, Krohn K, Endothelial dysfunction, oxidative stress, and risk of cardiovascular events in patients with coronary artery disease. Circulation 2001;104:2673-8
  • Cai H, Harrison DG. Endothelial dysfunction in cardiovascular diseases: the role of oxidant stress. Circ Res 2000;87:840-4
  • Van der Schyf CJ, Youdim MB. Multifunctional drugs as neurotherapeutics. Neurotherapeutics 2009;6:1-201
  • Silverman RB. Design of selective neuronal nitric oxide synthase inhibitors for the prevention and treatment of neurodegenerative diseases. Acc Chem Res 2009;42(3):439-51

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