2-Amino-4-arylthiazole compounds as TRPA1 antagonists (WO 2012085662): a patent evaluation

Bibliography

• Levine JD, Alessandri-Haber N. TRP channels: targets for the relief of pain. Biochim Biophys Acta 2007;1772:989-1003
   PubMed Web of Science ®Google Scholar
• Clapham DE, Julius D, Montell C, Schultz G. International Union of Pharmacology. XLIX. Nomenclature and structure-function relationships of transient receptor potential channels. Pharmacol Rev 2005;57:427-50
   PubMedGoogle Scholar
• Montell C. The TRP superfamily of cation channels. Sci STKE 2005;272:3-27
   Google Scholar
• Wu LJ, Sweet TB, Clapham DE. International Union of Basic and Clinical Pharmacology. LXXVI. Current progress in the mammalian TRP ion channel family. Pharmacol Rev 2010;62:381-404
   PubMed Web of Science ®Google Scholar
• Venkatachalam K, Montell C. TRP channels. Annu Rev Biochem 2007;76:387-417
   PubMed Web of Science ®Google Scholar
• Talavera K, Nilius B, Voets T. Neuronal TRP channels: thermometers, pathfinders and life-savers. Trends Neurosci 2008;31:287-95
   PubMed Web of Science ®Google Scholar
• Latorre R, Zaelzer C, Brauchi S. Structure-functional intimacies of transient receptor potential channels. Q Rev Biophys 2009;42:201-46
   PubMed Web of Science ®Google Scholar
• Voets T, Nilius B. Modulation of TRPs by PIPs. J Physiol 2007;582:939-44
   PubMed Web of Science ®Google Scholar
• Schmidt M, Dubin AE, Petrus MJ, Nociceptive signals induce trafficking of TRPA1 to the plasma membrane. Neuron 2009;64:498-509
   PubMed Web of Science ®Google Scholar
• Nilius B, Owsianik G. Transient receptor potential channelopathies. Pflugers Arch 2010;460:437-50
   PubMed Web of Science ®Google Scholar
• Jaquemar D, Schenker T, Trueb B. An ankyrin-like protein with transmembrane domains is specifically lost after oncogenic transformation of human fibroblasts. J Biol Chem 1999;274:7325-33
   PubMed Web of Science ®Google Scholar
• Story GM, Peier AM, Reeve AJ, ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell 2003;112:819-29
   PubMed Web of Science ®Google Scholar
• Lee G, Abdi K, Jiang Y, Nanospring behaviour of ankyrin repeats. Nature 2006;440:246-9
   PubMed Web of Science ®Google Scholar
• Nagata K, Duggan A, Kumar G, Garcia-Anoveros J. Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing. J Neurosci 2005;25:4052-61
   PubMed Web of Science ®Google Scholar
• Nassenstein C, Kwong K, Taylor-Clark T, Expression and function of the ion channel TRPA1 in vagal afferent nerves innervating mouse lungs. J Physiol 2008;586:1595-604
   PubMed Web of Science ®Google Scholar
• Brierley SM, Hughes PA, Page AJ, The ion channel TRPA1 is required for normal mechanosensation and is modulated by algesic stimuli. Gastroenterology 2009;137:2084-95
   PubMed Web of Science ®Google Scholar
• Weller K, Reeh PW, Sauer SK. TRPV1, TRPA1, and CB1 in the isolated vagus nerve–axonal chemosensitivity and control of neuropeptide release. Neuropeptides 2011;45:391-400
   PubMed Web of Science ®Google Scholar
• Kobayashi K, Fukuoka T, Obata K, Distinct expression of TRPM8, TRPA1, and TRPV1 mRNAs in rat primary afferent neurons with adelta/c-fibers and colocalization with trk receptors. J Comp Neurol 2005;493:596-606
   PubMed Web of Science ®Google Scholar
• Corey DP, Garcia-Anoveros J, Holt JR, TRPA1 is a candidate for the mechanosensitive transduction channel of vertebrate hair cells. Nature 2004;432:723-30
   PubMed Web of Science ®Google Scholar
• Atoyan R, Shander D, Botchkareva NV. Non-neuronal expression of transient receptor potential type A1 (TRPA1) in human skin. J Invest Dermatol 2009;129:2312-15
   PubMed Web of Science ®Google Scholar
• Kwan KY, Glazer JM, Corey DP, TRPA1 modulates mechanotransduction in cutaneous sensory neurons. J Neurosci 2009;29:4808-19
   PubMed Web of Science ®Google Scholar
• Bautista DM, Movahed P, Hinman A, Pungent products from garlic activate the sensory ion channel TRPA1. Proc Natl Acad Sci USA 2005;102:12248-52
   PubMed Web of Science ®Google Scholar
• Bautista DM, Jordt SE, Nikai T, TRPA1 mediates the inflammatory actions of environmental irritants and proalgesic agents. Cell 2006;124:1269-82
   PubMed Web of Science ®Google Scholar
• Macpherson LJ, Dubin AE, Evans MJ, Noxious compounds activate TRPA1 through covalent modification of cysteines. Nature 2007;445:541-5
   PubMed Web of Science ®Google Scholar
• Trevisani M, Siemens J, Materazzi S, 4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1. Proc Natl Acad Sci USA 2007;104:13519-24
   PubMed Web of Science ®Google Scholar
• Taylor-Clark TE, Undem BJ, Macglashan DW Jr, Prostaglandin-induced activation of nociceptive neurons via direct interaction with TRPA1. Mol Pharmacol 2008;73:274-81
   PubMed Web of Science ®Google Scholar
• Hinman A, Chuang HH, Bautista DM, Julius D. TRP channel activation by reversible covalent modification. Proc Natl Acad Sci USA 2006;103:19564-8
   PubMed Web of Science ®Google Scholar
• Bandell M, Story GM, Hwang SW, Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. Neuron 2004;41:849-57
   PubMed Web of Science ®Google Scholar
• Bessac BF, Sivula M, von Hehn CA, TRPA1 is a major oxidant sensor in murine airway sensory neurons. J Clin Invest 2008;118:1899-910
   PubMed Web of Science ®Google Scholar
• Sawada Y, Hosokawa H, Matsumura K, Kobayashi S. Activation of transient receptor potential ankyrin 1 by hydrogen peroxide. Eur J Neurosci 2008;27:1131-42
   PubMed Web of Science ®Google Scholar
• Takahashi N, Mizuno Y, Kozai D, Molecular characterization of TRPA1 activation by cysteine-reactive inflammatory mediators. Channels 2008;2:287-98
   PubMed Web of Science ®Google Scholar
• Andersson DA, Gentry C, Moss S, Bevan S. TRPA1 is a sensory receptor for multiple products of oxidative stress. J Neurosci 2008;28:2485-94
   PubMed Web of Science ®Google Scholar
• McNamara CR, Mandel-Brehm J, Bautista DM, TRPA1 mediates formalin-induced pain. Proc Natl Acad Sci USA 2007;104:13525-30
   PubMed Web of Science ®Google Scholar
• Bassoli A, Borgonovo G, Caimi S, Taste-guided identification of high potency TRPA1 agonists from Perilla frutescens. Bioorg Med Chem 2009;17:1636-9
   PubMed Web of Science ®Google Scholar
• Obata K, Katsura H, Mizushima T, TRPA1 induced in sensory neurons contributes to cold hyperalgesia after inflammation and nerve injury. J Clin Invest 2005;115:2393-401
   PubMed Web of Science ®Google Scholar
• Katsura H, Obata K, Mizushima T, Antisense knock down of TRPA1, but not TRPM8, alleviates cold hyperalgesia after spinal nerve ligation in rats. Exp Neurol 2006;200:112-23
   PubMed Web of Science ®Google Scholar
• Nilius B, Appendino G, Owsianik G. The transient receptor potential channel TRPA1: from gene to pathophysiology. Pflugers Arch 2012; Epub ahead of print
   Web of Science ®Google Scholar
• Baraldi PG, Preti D, Materazzi S, Geppetti P. TRPA1 as emerging target for novel analgesics and anti-inflammatory agents. J Med Chem 2010;53:5085-107
   PubMed Web of Science ®Google Scholar
• Karashima Y, Damann N, Prenen J, Bimodal action of menthol on the transient receptor potential channel TRPA1. J Neurosci 2007;27:9874-84
   PubMed Web of Science ®Google Scholar
• De Petrocellis L, Vellani V, Schiano-Moriello A, Plant-derived cannabinoids modulate the activity of transient receptor potential channels of ankyrin type-1 and melastatin type-8. Pharmacol Exp Ther 2008;325:1007-15
   PubMed Web of Science ®Google Scholar
• De Petrocellis L, Ligresti A, Schiano Moriello A, Effects of cannabinoids and cannabinoid-enriched Cannabis extracts on TRP channels and endocannabinoid metabolic enzymes. Br J Pharmacol 2011;163:1479-94
   PubMed Web of Science ®Google Scholar
• Holzer P. Transient receptor potential (TRP) channels as drug targets for diseases of the digestive system. Pharmacol Ther 2011;131:142-70
   PubMed Web of Science ®Google Scholar
• Andersson DA, Gentry C, Alenmyr L, TRPA1 mediates spinal antinociception induced by acetaminophen and the cannabinoid Delta9-tetrahydrocannabiorcol. Nat Commun 2011;2:551
   PubMed Web of Science ®Google Scholar
• Avonto C, Taglialatela-Scafati O, Pollastro F, An NMR spectroscopic method to identify and classify thiol-trapping agents: revival of Michael acceptors for drug discovery? Angew Chem Int Ed Engl 2011;50:467-71
   PubMed Web of Science ®Google Scholar
• Doerner JF, Gisselmann G, Hatt H, Wetzel CH. Transient receptor potential channel A1 is directly gated by calcium ions. J Biol Chem 2007;282:13180-9
   PubMed Web of Science ®Google Scholar
• Zuborg S, Yurgionas B, Jira JA, Direct activation of TRPA1 by Ca2+. Nat Neurosci 2007;10:277-9
   PubMed Web of Science ®Google Scholar
• Wang YY, Chang RB, Waters HN, The nociceptor ion channel TRPA1 is potentiated and inactivated by permeating calcium ions. J Biol Chem 2008;283:32691-703
   PubMed Web of Science ®Google Scholar
• Andersson DA, Gentry C, Moss S, Bevan S. Clioquinol and pyrithione activate. TRPA1 by increasing intracellular Zn2+. Proc Natl Acad Sci USA 2009;106:8374-9
   PubMed Web of Science ®Google Scholar
• Hu H, Bandell M, Petrus MJ, Zinc activates damage-sensing TRPA1 ion channels. Nat Chem Biol 2009;5:183-90
   PubMed Web of Science ®Google Scholar
• Jordt SE, Bautista DM, Chuang HH, Mustard oils and cannabinoids excite sensory nerve fibres through the TRP channel ANKTM1. Nature 2004;427:260-5
   PubMed Web of Science ®Google Scholar
• Macpherson LJ, Xiao B, Kwan KY, An ion channel essential for sensing chemical damage. J Neurosci 2007;27:11412-15
   PubMed Web of Science ®Google Scholar
• McMahon SB, Wood JN. Increasingly irritable and close to tears: TRPA1 in inflammatory pain. Cell 2006;124:1123-5
   PubMed Web of Science ®Google Scholar
• Materazzi S, Nassini R, Andre E, Cox-dependent fatty acid metabolites cause pain through activation of the irritant receptor TRPA1. Proc Natl Acad Sci USA 2008;105:12045-50
   PubMed Web of Science ®Google Scholar
• Ji RR, Xu ZZ, Strichartz G, Serhan CN. Emerging roles of resolvins in the resolution of inflammation and pain. Trends Neurosci 2011;34:599-609
   PubMed Web of Science ®Google Scholar
• Park CK, Xu ZZ, Liu T, Resolvin D2 is a potent endogenous inhibitor for. TRPV1/A1, inflammatory pain, and spinal cord synaptic plasticity in mice: distinct roles of resolvin D1, D2, and E1. J Neurosci 2011;31:18433-8
   PubMed Web of Science ®Google Scholar
• Shigetomi E, Tong X, Kwan KY, TRPA1 channels regulate astrocyte resting calcium and inhibitory synapse efficacy through GAT-3. Nat Neurosci 2011;15:70-80
   PubMed Web of Science ®Google Scholar
• Wang YY, Chang RB, Liman ER, TRPA1 is a component of the nociceptive response to CO2. J Neurosci 2010;30:12958-63
   PubMed Web of Science ®Google Scholar
• Petrus M, Peier AM, Bandell M, A role of TRPA1 in mechanical hyperalgesia is revealed by pharmacological inhibition. Mol Pain 2007;3:40
   PubMed Web of Science ®Google Scholar
• Eid SR, Crown ED, Moore EL, HC-030031, a TRPA1 selective antagonist, attenuates inflammatory- and neuropathy-induced mechanical hypersensitivity. Mol Pain 2008;4:48
   PubMed Web of Science ®Google Scholar
• da Costa DS, Meotti FC, Andrade EL, The involvement of the transient receptor potential A1 (TRPA1) in the maintenance of mechanical and cold hyperalgesia in persistent inflammation. Pain 2010;148:431-7
   PubMed Web of Science ®Google Scholar
• del Camino D, Murphy S, Heiry M, TRPA1 contributes to cold hypersensitivity. J Neurosci 2010;30:15165-74
   PubMed Web of Science ®Google Scholar
• McGaraughty S, Chu KL, Perner RJ, TRPA1 modulation of spontaneous and mechanically evoked firing of spinal neurons in uninjured, osteoarthritic, and inflamed rats. Mol Pain 2010;6:14
   PubMed Web of Science ®Google Scholar
• Fernandes ES, Russell FA, Spina D, A distinct role for TRPA1, in addition to TRPV1, in TNFa-induced inflammatory hyperalgesia and Freund's complete adjuvant-induced monarthritis. Arthritis Rheum 2011;63:819-29
   PubMed Web of Science ®Google Scholar
• Patapoutian A, Tate S, Woolf CJ. Transient receptor potential channels: targeting pain at the source. Nature Rev Drug Discov 2009;8:55-68
   PubMed Web of Science ®Google Scholar
• Caceres AI, Brackmann M, Elia MD, A sensory neuronal ion channel essential for airway inflammation and hyper-reactivity in asthma. Proc Natl Acad Sci USA 2009;106:9099-104
   PubMed Web of Science ®Google Scholar
• Nassini R, Materazzi S, Vriens J, The 'headache tree' via umbellulone and TRPA1 activates the trigeminovascular system. Brain 2012;135:376-90
   PubMed Web of Science ®Google Scholar
• Kremeyer B, Lopera F, Cox JJ, A gain-of-function mutation in TRPA1 causes familial episodic pain syndrome. Neuron 2010;66:671-80
   PubMed Web of Science ®Google Scholar
• Wei H, Chapman H, Saarnilehto M, Roles of cutaneous versus spinal TRPA1 channels in mechanical hypersensitivity in the diabetic or mustard oil-treated non-diabetic rat. Neuropharmacology 2010;58:578-84
   PubMed Web of Science ®Google Scholar
• Eberhardt MJ, Filipovic MR, Leffler A, Methylglyoxal activates nociceptors through Transient Receptor Potential Channel A1 (TRPA1): a possible mechanism of metabolic neuropathies. J Biol Chem 2012;287:28291-306
   PubMed Web of Science ®Google Scholar
• Muthuppalniappan M, Kumar S, Thomas A, Phthalimide derivatives as TRPA1 modulators. WO2009118596; 2009
   Google Scholar
• Chaudhari SS, Thomas A, Patil NP, Imidazo [2,1-B] purine derivatives as TRPA1 modulators. WO2009144548; 2009
   Google Scholar
• Kumar S, Thomas A, Waghmare NT, Thienopyrimidinedione derivatives as TRPA1 modulators. WO2010109334; 2010
   Google Scholar
• Chaudhari SS, Thomas A, Patil NP, Furopyrimidinedione derivatives as TRPA1 modulators. WO2010109329; 2010
   Google Scholar
• Kumar S, Thomas A, Margal S, Isothiazolo-pyrimidinedione derivatives as TRPA1 modulators. WO2010109328; 2010
   Google Scholar
• Muthuppalniappan M, Thomas A, Kumar S, Quinazoline dione derivatives as TRPA1 modulators. WO2010004390; 2010
   Google Scholar
• Chaudhari SS, Kumar S, Thomas A, Fused Pyrimidine-dione derivatives as TRPA1 modulators. WO2010109287; 2010
   Google Scholar
• Chen J, Kym PR. TRPA1: the species difference. J Gen Physiol 2009;133:623-5
   PubMed Web of Science ®Google Scholar
• Bang S, Kim KY, Yoo S, Transient receptor potential A1 mediates acetaldehyde-evoked pain sensation. Eur J Neurosci 2007;26:2516-23
   PubMed Web of Science ®Google Scholar
• Xu H, Blair NT, Clapham DE. Camphor activates and strongly desensitizes the transient receptor potential vanilloid subtype 1 channel in a vanilloid-independent mechanism. J Neurosci 2005;25:8924-37
   PubMed Web of Science ®Google Scholar
• Defalco J, Steiger D, Gustafson A, Oxime derivatives related to AP18: agonists and antagonists of the TRPA1 receptor. Bioorg Med Chem Lett 2010;20:276-9
   PubMed Web of Science ®Google Scholar
• Chen J, Joshi SK, DiDomenico S, Selective blockade of TRPA1 channel attenuates pathological pain without altering noxious cold sensation or body temperature regulation. Pain 2011;152:1165-72
   PubMed Web of Science ®Google Scholar
• Perner RJ, Kort ME, Didomenico SJ, (Heteroaryl)alkenone oxime derivatives as TRPA1 antagonists useful in the treatment of various diseases. WO2009089083; 2009
   Google Scholar
• Patapoutian A, Jegla TJ. Methods and compositions for treating hyperalgesia. WO2007098252; 2007
   Google Scholar
• Klionsky L, Tamir R, Gao B, Species-specific pharmacology of Trichloro(sulfanyl)ethyl benzamides as transient receptor potential ankyrin 1 (TRPA1) antagonists. Mol Pain 2007;3:39
   PubMed Web of Science ®Google Scholar
• Chen J, Lake MR, Sabet RS, Utility of large-scale transiently transfected cells for cell-based high-throughput screens to identify transient receptor potential channel A1 (TRPA1) antagonists. J Biomol Screen 2007;12:61-9
   PubMed Web of Science ®Google Scholar
• Chen J, Zhang X-F, Kort ME, Molecular determinants of species-specific activation or blockade of TRPA1 channels. J Neurosci 2008;28:5063-71
   PubMed Web of Science ®Google Scholar
• Gijsen HJ, Berthelot D, De Cleyn MA, Tricyclic 3,4-dihydropyrimidine-2-thione derivatives as potent TRPA1 antagonists. Bioorg Med Chem Lett 2012;22:797-800
   PubMed Web of Science ®Google Scholar
• Bilodeau MT, Egbertson M, Green A, Novel TRPAl antagonists. International Patent. WO2011043954, 2011
   Google Scholar
• Vallin KS, Sterky KJ, Nyman E, N-1-Alkyl-2-oxo-2-aryl amides as novel antagonists of the TRPA1 receptor. Bioorg Med Chem Lett 2012;22:5485-92
   PubMedGoogle Scholar
• Wei H, Haemaelaeinen MM, Saarnilehto M, Attenuation of mechanical hypersensitivity by an antagonist of the TRPA1 ion channel in diabetic animals. Anesthesiology 2009;111:147-54
   PubMed Web of Science ®Google Scholar
• Ng H, Weigele M, Moran M, Methods and compositions for treating disorders. US20090143377; 2009
   Google Scholar
• Ng H, Hang J. Compositions useful to treating disorders relate to TRPA1. WO2010075353; 2010
   Google Scholar
• Nagatomo K, Kubo Y. Caffeine activates mouse TRPA1 channels but suppresses human TRPA1 channels. Proc Natl Acad Sci USA 2008;105:17373-8
   PubMed Web of Science ®Google Scholar
• Baraldi PG, Romagnoli R, Saponaro G, 7-Substituted-pyrrolo[3,2-d]pyrimidine-2,4-dione derivatives as antagonists of the transient receptor potential ankyrin 1 (TRPA1) channel: a promising approach for treating pain and inflammation. Bioorg Med Chem 2012;20:1690-8
   PubMed Web of Science ®Google Scholar
• Harada N, Hongu M, Tanaka T, A. simple preparation of chloromethyl esters of the blocked amino acids. Synthetic Comm 1994;24:767-72
   Web of Science ®Google Scholar
• Robinson RP, Reiter LA, Barth WE, Discovery of the hemifumarate and (alpha-L-alanyloxy)methyl ether as prodrugs of an antirheumatic oxindole: prodrugs for the enolic OH group. J Med Chem 1996;39:10-18
   PubMed Web of Science ®Google Scholar
• Sams AG, Mikkelsen GK, Larsen M, Discovery of Phosphoric Acid Mono-{2-[(E/Z)-4-(3,3-dimethyl-butyrylamino)-3,5-difluoro-benzoylimino]-thiazol-3-ylmethyl} ester (Lu AA47070): a Phosphonooxymethylene prodrug of a potent and selective hA(2A) receptor antagonist. J Med Chem 2011;54:751-64
   PubMed Web of Science ®Google Scholar
• Mantyla A, Vepsalainen J, Jarvinena T, Nevalainen T. A novel synthetic route for the preparation of alkyl and benzyl chloromethyl phosphates. Tetrahedron Lett 2002;43:3793-4
   Web of Science ®Google Scholar