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

Expert Opinion on Therapeutic Patents

Volumn 23, Issue 1, 2013, Pages 119-147

  De Petrocellis, Luciano ^a   Schiano Moriello, Aniello ^b  

^a CNR   (Italy)

^b Istituto di Chimica Biomolecolare   (Italy)

Author keywords

2 amino 4 arylthiazoles; Antagonist; Pain; TRPA1

Indexed keywords

CHEMBRIDGE 5861528; N (4 ISOPROPYLPHENYL) 2 (1,2,3,6 TETRAHYDRO 1,3 DIMETHYL 2,6 DIOXO 7H PURIN 7 YL)ACETAMIDE; PROTEIN INHIBITOR; THIAZOLE DERIVATIVE; TRANSIENT RECEPTOR POTENTIAL ANKYRIN 1 ANTAGONIST; TRANSIENT RECEPTOR POTENTIAL CHANNEL A1; UNCLASSIFIED DRUG;

AREA UNDER THE CURVE; ARTICLE; CHO CELL; CHRONIC PAIN; DIABETIC NEUROPATHY; DISEASE ASSOCIATION; DRUG SOLUBILITY; IC 50; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; INFLAMMATORY DISEASE; MAXIMUM PLASMA CONCENTRATION; NEUROPATHIC PAIN; NONHUMAN; OSTEOARTHRITIS; PAIN; RHEUMATOID ARTHRITIS;

ANIMALS; CALCIUM CHANNELS; DRUG DESIGN; HUMANS; INFLAMMATION; NERVE TISSUE PROTEINS; PAIN; PATENTS AS TOPIC; THIAZOLES; TRANSIENT RECEPTOR POTENTIAL CHANNELS;

EID: 84871515396     PISSN: 13543776     EISSN: 17447674     Source Type: Journal    
DOI: 10.1517/13543776.2013.736496     Document Type: Article

References (97)

1. Levine JD, Alessandri-Haber N. TRP channels: targets for the relief of pain. Biochim Biophys Acta 2007;1772:989-1003 (Pubitemid 47176368)
2. 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
3. Montell C. The TRP superfamily of cation channels. Sci STKE 2005;272:3-27
4. 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
5. Venkatachalam K, Montell C. TRP channels. Annu Rev Biochem 2007;76:387-417
6. Talavera K, Nilius B, Voets T. Neuronal TRP channels: thermometers, pathfinders and life-savers. Trends Neurosci 2008;31:287-95
7. Latorre R, Zaelzer C, Brauchi S. Structure-functional intimacies of transient receptor potential channels. Q Rev Biophys 2009;42:201-46
8. Voets T, Nilius B. Modulation of TRPs by PIPs. J Physiol 2007;582:939-44 (Pubitemid 47104330)
9. Schmidt M, Dubin AE, Petrus MJ, et al. Nociceptive signals induce trafficking of TRPA1 to the plasma membrane. Neuron 2009;64:498-509
10. Nilius B, Owsianik G. Transient receptor potential channelopathies. Pflugers Arch 2010;460:437-50
11. 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
12. Story GM, Peier AM, Reeve AJ, et al. ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell 2003;112:819-29 (Pubitemid 36378884)
13. Lee G, Abdi K, Jiang Y, et al. Nanospring behaviour of ankyrin repeats. Nature 2006;440:246-9 (Pubitemid 43372106)
14. 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 (Pubitemid 40563380)
15. Nassenstein C, Kwong K, Taylor-Clark T, et al. Expression and function of the ion channel TRPA1 in vagal afferent nerves innervating mouse lungs. J Physiol 2008;586:1595-604 (Pubitemid 351404963)
16. Brierley SM, Hughes PA, Page AJ, et al. The ion channel TRPA1 is required for normal mechanosensation and is modulated by algesic stimuli. Gastroenterology 2009;137:2084-95
17. 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
18. Kobayashi K, Fukuoka T, Obata K, et al. 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 (Pubitemid 41780630)
19. Corey DP, Garcia-Anoveros J, Holt JR, et al. TRPA1 is a candidate for the mechanosensitive transduction channel of vertebrate hair cells. Nature 2004;432:723-30 (Pubitemid 39656287)
20. 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
21. Kwan KY, Glazer JM, Corey DP, et al. TRPA1 modulates mechanotransduction in cutaneous sensory neurons. J Neurosci 2009;29:4808-19
22. Bautista DM, Movahed P, Hinman A, et al. Pungent products from garlic activate the sensory ion channel TRPA1. Proc Natl Acad Sci USA 2005;102:12248-52 (Pubitemid 41291160)
23. Bautista DM, Jordt SE, Nikai T, et al. TRPA1 mediates the inflammatory actions of environmental irritants and proalgesic agents. Cell 2006;124:1269-82
24. Macpherson LJ, Dubin AE, Evans MJ, et al. Noxious compounds activate TRPA1 through covalent modification of cysteines. Nature 2007;445:541-5 (Pubitemid 46197634)
25. Trevisani M, Siemens J, Materazzi S, et al. 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 (Pubitemid 47293977)
26. Taylor-Clark TE, Undem BJ, Macglashan DW Jr, et al. Prostaglandin-induced activation of nociceptive neurons via direct interaction with TRPA1. Mol Pharmacol 2008;73:274-81 (Pubitemid 351159199)
27. Hinman A, Chuang HH, Bautista DM, Julius D. TRP channel activation by reversible covalent modification. Proc Natl Acad Sci USA 2006;103:19564-8 (Pubitemid 46026070)
28. Bandell M, Story GM, Hwang SW, et al. Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. Neuron 2004;41:849-57 (Pubitemid 38429729)
29. Bessac BF, Sivula M, von Hehn CA, et al. TRPA1 is a major oxidant sensor in murine airway sensory neurons. J Clin Invest 2008;118:1899-910 (Pubitemid 351632392)
30. 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 (Pubitemid 351432345)
31. Takahashi N, Mizuno Y, Kozai D, et al. Molecular characterization of TRPA1 activation by cysteine-reactive inflammatory mediators. Channels 2008;2:287-98
32. 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 (Pubitemid 351348185)
33. McNamara CR, Mandel-Brehm J, Bautista DM, et al. TRPA1 mediates formalin-induced pain. Proc Natl Acad Sci USA 2007;104:13525-3034.
34. Bassoli A, Borgonovo G, Caimi S, et al. Taste-guided identification of high potency TRPA1 agonists from Perilla frutescens. Bioorg Med Chem 2009;17:1636-9
35. Obata K, Katsura H, Mizushima T, et al. TRPA1 induced in sensory neurons contributes to cold hyperalgesia after inflammation and nerve injury. J Clin Invest 2005;115:2393-401 (Pubitemid 41266201)
36. Katsura H, Obata K, Mizushima T, et al. Antisense knock down of TRPA1, but not TRPM8, alleviates cold hyperalgesia after spinal nerve ligation in rats. Exp Neurol 2006;200:112-23 (Pubitemid 44080752)
37. Nilius B, Appendino G, Owsianik G. The transient receptor potential channel TRPA1: from gene to pathophysiology. Pflugers Arch 2012; Epub ahead of print 38. 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
38. Karashima Y, Damann N, Prenen J, et al. Bimodal action of menthol on the transient receptor potential channel TRPA1. J Neurosci 2007;27:9874-84 (Pubitemid 47403994)
39. De Petrocellis L, Vellani V, Schiano-Moriello A, et al. 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 (Pubitemid 351724325)
40. De Petrocellis L, Ligresti A, Schiano Moriello A, et al. Effects of cannabinoids and cannabinoid-enriched Cannabis extracts on TRP channels and endocannabinoid metabolic enzymes. Br J Pharmacol 2011;163:1479-94
41. Holzer P. Transient receptor potential (TRP) channels as drug targets for diseases of the digestive system. Pharmacol Ther 2011;131:142-70
42. Andersson DA, Gentry C, Alenmyr L, et al. TRPA1 mediates spinal antinociception induced by acetaminophen and the cannabinoid Delta9-tetrahydrocannabiorcol. Nat Commun 2011;2:551
43. Avonto C, Taglialatela-Scafati O, Pollastro F, et al. 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
44. 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 (Pubitemid 47100541)
45. Zuborg S, Yurgionas B, Jira JA, et al. Direct activation of TRPA1 by Ca2+. Nat Neurosci 2007;10:277-9
46. Wang YY, Chang RB, Waters HN, et al. The nociceptor ion channel TRPA1 is potentiated and inactivated by permeating calcium ions. J Biol Chem 2008;283:32691-703
47. 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
48. Hu H, Bandell M, Petrus MJ, et al. Zinc activates damage-sensing TRPA1 ion channels. Nat Chem Biol 2009;5:183-90
49. Jordt SE, Bautista DM, Chuang HH, et al. Mustard oils and cannabinoids excite sensory nerve fibres through the TRP channel ANKTM1. Nature 2004;427:260-5 (Pubitemid 38112043)
50. Macpherson LJ, Xiao B, Kwan KY, et al. An ion channel essential for sensing chemical damage. J Neurosci 2007;27:11412-15 (Pubitemid 47621302)
51. McMahon SB, Wood JN. Increasingly irritable and close to tears: TRPA1 in inflammatory pain. Cell 2006;124:1123-5
52. Materazzi S, Nassini R, Andre E, et al. Cox-dependent fatty acid metabolites cause pain through activation of the irritant receptor TRPA1. Proc Natl Acad Sci USA 2008;105:12045-50
53. 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
54. Park CK, Xu ZZ, Liu T, et al. 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
55. Shigetomi E, Tong X, Kwan KY, et al. TRPA1 channels regulate astrocyte resting calcium and inhibitory synapse efficacy through GAT-3. Nat Neurosci 2011;15:70-80
56. Wang YY, Chang RB, Liman ER, et al. TRPA1 is a component of the nociceptive response to CO2. J Neurosci 2010;30:12958-63
57. Petrus M, Peier AM, Bandell M, et al. A role of TRPA1 in mechanical hyperalgesia is revealed by pharmacological inhibition. Mol Pain 2007;3:40
58. Eid SR, Crown ED, Moore EL, et al. HC-030031, a TRPA1 selective antagonist, attenuates inflammatory- and neuropathy-induced mechanical hypersensitivity. Mol Pain 2008;4:48
59. da Costa DS, Meotti FC, Andrade EL, et al. 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
60. del Camino D, Murphy S, Heiry M, et al. TRPA1 contributes to cold hypersensitivity. J Neurosci 2010;30:15165-74
61. McGaraughty S, Chu KL, Perner RJ, et al. TRPA1 modulation of spontaneous and mechanically evoked firing of spinal neurons in uninjured, osteoarthritic, and inflamed rats. Mol Pain 2010;6:14
62. Fernandes ES, Russell FA, Spina D, et al. 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
63. Patapoutian A, Tate S, Woolf CJ. Transient receptor potential channels: targeting pain at the source. Nature Rev Drug Discov 2009;8:55-68
64. Caceres AI, Brackmann M, Elia MD, et al. A sensory neuronal ion channel essential for airway inflammation and hyper-reactivity in asthma. Proc Natl Acad Sci USA 2009;106:9099-104
65. Nassini R, Materazzi S, Vriens J, et al. The 'headache tree' via umbellulone and TRPA1 activates the trigeminovascular system. Brain 2012;135:376-90
66. Kremeyer B, Lopera F, Cox JJ, et al. A gain-of-function mutation in TRPA1 causes familial episodic pain syndrome. Neuron 2010;66:671-80
67. Wei H, Chapman H, Saarnilehto M, et al. 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
68. Eberhardt MJ, Filipovic MR, Leffler A, et al. Methylglyoxal activates nociceptors through Transient Receptor PotentialChannel A1 (TRPA1): a possible mechanism of metabolic neuropathies. J Biol Chem 2012;287:28291-306
69. Muthuppalniappan M, Kumar S, Thomas A, et al. Phthalimide derivatives as TRPA1 modulators. WO2009118596; 2009
70. Chaudhari SS, Thomas A, Patil NP, et al. Imidazo [2,1-B] purine derivatives as TRPA1 modulators. WO2009144548; 2009
71. Kumar S, Thomas A, Waghmare NT, et al. Thienopyrimidinedione derivatives as TRPA1 modulators. WO2010109334; 2010
72. Chaudhari SS, Thomas A, Patil NP, et al. Furopyrimidinedione derivatives as TRPA1 modulators. WO2010109329; 2010
73. Kumar S, Thomas A, Margal S, et al. Isothiazolo-pyrimidinedione derivatives as TRPA1 modulators. WO2010109328; 2010
74. Muthuppalniappan M, Thomas A, Kumar S, et al. Quinazoline dione derivatives as TRPA1 modulators. WO2010004390; 2010
75. Chaudhari SS, Kumar S, Thomas A, et al. Fused Pyrimidine-dione derivatives as TRPA1 modulators. WO2010109287; 2010
76. Chen J, Kym PR. TRPA1: the species difference. J Gen Physiol 2009;133:623-5
77. Bang S, Kim KY, Yoo S, et al. Transient receptor potential A1 mediates acetaldehyde-evoked pain sensation. Eur J Neurosci 2007;26:2516-23 (Pubitemid 350050447)
78. 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 (Pubitemid 41384461)
79. Defalco J, Steiger D, Gustafson A, et al. Oxime derivatives related to AP18: agonists and antagonists of the TRPA1 receptor. Bioorg Med Chem Lett 2010;20:276-9
80. Chen J, Joshi SK, DiDomenico S, et al. Selective blockade of TRPA1 channel attenuates pathological pain without altering noxious cold sensation or body temperature regulation. Pain 2011;152:1165-72
81. Perner RJ, Kort ME, Didomenico SJ, et al. (Heteroaryl)alkenone oxime derivatives as TRPA1 antagonists useful in the treatment of various diseases. WO2009089083; 2009
82. Patapoutian A, Jegla TJ. Methods and compositions for treating hyperalgesia. WO2007098252; 2007
83. Klionsky L, Tamir R, Gao B, et al. Species-specific pharmacology of Trichloro(sulfanyl)ethyl benzamides as transient receptor potential ankyrin 1 (TRPA1) antagonists. Mol Pain 2007;3:39
84. Chen J, Lake MR, Sabet RS, et al. Utility of large-scale transiently transfected cells for cell-based highthroughput screens to identify transient receptor potential channel A1 (TRPA1) antagonists. J Biomol Screen 2007;12:61-9 (Pubitemid 46224920)
85. Chen J, Zhang X-F, Kort ME, et al. Molecular determinants of species-specific activation or blockade of TRPA1 channels. J Neurosci 2008;28:5063-71
86. Gijsen HJ, Berthelot D, De Cleyn MA, et al. Tricyclic 3,4-dihydropyrimidine-2- thione derivatives as potent TRPA1 antagonists. Bioorg Med Chem Lett 2012;22:797-800
87. Bilodeau MT, Egbertson M, Green A, et al. Novel TRPAl antagonists. International Patent. WO2011043954, 2011
88. Vallin KS, Sterky KJ, Nyman E, et al. N-1-Alkyl-2-oxo-2-aryl amides as novel antagonists of the TRPA1 receptor. Bioorg Med Chem Lett 2012;22:5485-92
89. Wei H, Haemaelaeinen MM, Saarnilehto M, et al. Attenuation of mechanical hypersensitivity by an antagonist of the TRPA1 ion channel in diabetic animals. Anesthesiology 2009;111:147-54
90. Ng H, Weigele M, Moran M, et al. Methods and compositions for treating disorders. US20090143377; 2009
91. Ng H, Hang J. Compositions useful to treating disorders relate to TRPA1. WO2010075353; 2010
92. Nagatomo K, Kubo Y. Caffeine activates mouse TRPA1 channels but suppresses human TRPA1 channels. Proc Natl Acad Sci USA 2008;105:17373-8
93. Baraldi PG, Romagnoli R, Saponaro G, et al. 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
94. Harada N, Hongu M, Tanaka T, et al. A. simple preparation of chloromethyl esters of the blocked amino acids. Synthetic Comm 1994;24:767-72 (Pubitemid 24121061)
95. Robinson RP, Reiter LA, Barth WE, et al. 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 (Pubitemid 26025531)
96. Sams AG, Mikkelsen GK, Larsen M, et al. Discovery of Phosphoric Acid Mono-{2-[(E/Z)-4-(3,3-dimethylbutyrylamino)- 3,5-difluorobenzoylimino]- 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
97. 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 (Pubitemid 34463031)