Urate transporter URAT1 inhibitors: a patent review (2012 - 2015)

References

• Abramson R, Lipkowitz M. Evolution of the uric acid transport mechanisms in vertebrate kidney. Basic Principles in Transport. 1990;3:115–153.
   Google Scholar
• Terkeltaub R. Update on gout: new therapeutic strategies and options. Nat Rev Rheumatol. 2010;6:30–38.
   PubMed Web of Science ®Google Scholar
• Hediger MA, Johnson RJ, Miyazaki H, et al. Molecular physiology of urate transport. Physiology (Bethesda, Md). 2005;20:125–133.
   PubMed Web of Science ®Google Scholar
• Khanna D, Fitzgerald JD, Khanna PP, et al. 2012 American College of Rheumatology guidelines for management of gout. Part 1: systematic nonpharmacologic and pharmacologic therapeutic approaches to hyperuricemia. Arthritis Care Res (Hoboken). 2012;64:1431–1446.
   PubMed Web of Science ®Google Scholar
• Zhang W, Doherty M, Bardin T, et al. EULAR evidence based recommendations for gout. Part II: Management. Report of a task force of the EULAR Standing Committee for International Clinical Studies Including Therapeutics (ESCISIT). Ann Rheum Dis. 2006;65:1312–1324.
   PubMed Web of Science ®Google Scholar
• Shahid H, Singh JA. Investigational drugs for hyperuricemia. Expert Opin Investig Drugs. 2015;24:1013–1030.
   PubMed Web of Science ®Google Scholar
• Fam AG. Difficult gout and new approaches for control of hyperuricemia in the allopurinol-allergic patient. Curr Rheumatol Rep. 2001;3:29–35.
   PubMedGoogle Scholar
• Curiel RV, Guzman NJ. Challenges associated with the management of gouty arthritis in patients with chronic kidney disease: a systematic review. Semin Arthritis Rheum. 2012;42:166–178.
   PubMed Web of Science ®Google Scholar
• Shin HJ, Takeda M, Enomoto A, et al. Interactions of urate transporter URAT1 in human kidney with uricosuric drugs. Nephrology (Carlton). 2011;16:156–162.
   PubMed Web of Science ®Google Scholar
• Castrejon I, Toledano E, Rosario MP, et al. Safety of allopurinol compared with other urate-lowering drugs in patients with gout: a systematic review and meta-analysis. Rheumatol Int. 2015;35:1127–1137.
   PubMed Web of Science ®Google Scholar
• Sachs L, Batra KL, Zimmermann B. Medical implications of hyperuricemia. Med Health R I. 2009;2:353–355.
   Google Scholar
• Pittman JR, Bross MH. Diagnosis and management of gout. Am Fam Physician. 1999;59:1799–1806, 1810.
   PubMed Web of Science ®Google Scholar
• Mandal AK, Mount DB. The molecular physiology of uric acid homeostasis. Annu Rev Physiol. 2015;77:323–345.
   PubMed Web of Science ®Google Scholar
• Anzai N, Jutabha P, Amonpatumrat-Takahashi S, et al. Recent advances in renal urate transport: characterization of candidate transporters indicated by genome-wide association studies. Clin Exp Nephrol. 2012;16:89–95.
   PubMed Web of Science ®Google Scholar
• Li Z, Ding H, Chen C, et al. Novel URAT1 mutations caused acute renal failure after exercise in two Chinese families with renal hypouricemia. Gene. 2013;512:97–101.
   PubMed Web of Science ®Google Scholar
• Dehghan A, Kottgen A, Yang Q, et al. Association of three genetic loci with uric acid concentration and risk of gout: a genome-wide association study. Lancet. 2008;372:1953–1961.
   PubMed Web of Science ®Google Scholar
• Phipps-Green AJ, Merriman ME, Topless R, et al. Twenty-eight loci that influence serum urate levels: analysis of association with gout. Ann Rheum Dis. 2016;75:124–130.
   PubMed Web of Science ®Google Scholar
• Kottgen A, Albrecht E, Teumer A, et al. Genome-wide association analyses identify 18 new loci associated with serum urate concentrations. Nat Genet. 2013;45:145–154.
   PubMed Web of Science ®Google Scholar
• Flynn TJ, Phipps-Green A, Hollis-Moffatt JE, et al. Association analysis of the SLC22A11 (organic anion transporter 4) and SLC22A12 (urate transporter 1) urate transporter locus with gout in New Zealand case-control sample sets reveals multiple ancestral-specific effects. Arthritis Res Ther. 2013;15:R220.
   PubMed Web of Science ®Google Scholar
• Wu W, Av D, Sk N. Remote communication through solute carriers and ATP binding cassette drug transporter pathways: an update on the remote sensing and signaling hypothesis. Mol Pharmacol. 2011;79:795–805.
   PubMed Web of Science ®Google Scholar
• Enomoto A, Kimura H, Chairoungdua A, et al. Molecular identification of a renal urate anion exchanger that regulates blood urate levels. Nature. 2002;417:447–452.
   PubMed Web of Science ®Google Scholar
• Vazquez-Mellado J, Jimenez-Vaca AL, Cuevas-Covarrubias S, et al. Molecular analysis of the SLC22A12 (URAT1) gene in patients with primary gout. Rheumatology (Oxford). 2007;46:215–219.
   PubMed Web of Science ®Google Scholar
• Reginato AM, Mount DB, Yang I, et al. The genetics of hyperuricaemia and gout. Nat Rev Rheumatol. 2012;8:610–621.
   PubMed Web of Science ®Google Scholar
• Diaz-Torne C, Perez-Herrero N, Perez-Ruiz F. New medications in development for the treatment of hyperuricemia of gout. Curr Opin Rheumatol. 2015;27:164–169.
   PubMed Web of Science ®Google Scholar
• Hamada T, Ichida K, Hosoyamada M, et al. Uricosuric action of losartan via the inhibition of urate transporter 1 (URAT 1) in hypertensive patients. Am J Hypertens. 2008;21:1157–1162.
   PubMed Web of Science ®Google Scholar
• Nindita Y, Hamada T, Bahrudin U, et al. Effect of losartan and benzbromarone on the level of human urate transporter 1 mRNA. Arzneimittelforschung. 2010;60:186–188.
   PubMed Web of Science ®Google Scholar
• Perez-Ruiz F, Hingorani V, Welp J, et al. Efficacy and safety of a range of doses of RDEA594, a novel uricosuric agent, as a single agent in hyperuricemic gout patients: multicenter, randomized, double-blind, placebo-controlled, phase 2 experience. Ann Rheum Dis. 2010;69(Suppl 2):121.
   Google Scholar
• Lesinurad Summary Review. US Food and Drug Administration Center for Drug Evaluation and Research. Available from: http://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/207988Orig207981s207000SumR.pdf.
   Google Scholar
• Miner JN, Tan P. FRI0389 RDEA3170, a novel, high affinity URAT1 inhibitor binds to a central domain within URAT1. Ann Rheum Dis. 2013;71(Suppl 1):446.
   Google Scholar
• Tan P, Hyndman D, Miner JN. Identification of specific amino acids in the uric acid transporter URAT1 required for uricosuric-mediated inhibition. Arthritis Rheum. 2011;63(Suppl 10):1592.
   Google Scholar
• Miner JN, Ostertag T, Hyndman D, et al. RDEA684, a novel, potent and efficacious inhibitor of human urate transporter, urat1, with a favorable pharmacokinetic profile, and no mitochondrial toxicity. Ann Rheum Dis. 2010;69(Suppl 3):122.
   Google Scholar
• Yang JX, Yang C, Bowlin S, et al. 0623170, a potent URAT1 inhibitor with a favorable pharmacokinetic and toxicity profile. Drug Metab Rev. 2011;43:85–86.
   Web of Science ®Google Scholar
• Bassett DR, Mikkelsen WM, Buckingham RB, et al. Effects of halofenate and probenecid on serum lipids and uric acid in hyperlipidemic, hyperuricemic adults. Clin Pharmacol Ther. 1977;22:340–351.
   PubMed Web of Science ®Google Scholar
• Lavan BE, McWherter C, Choi YJ. FRI0403 Arhalofenate, a novel uricosuric agent, is an inhibitor of human uric acid transporters. Ann Rheum Dis. 2013;71(Suppl 3):450–451.
   Google Scholar
• Choi YJ, Larroca V, Lucman A, et al. Arhalofenate is a novel dual-acting agent with uricosuric and anti-inflammatory properties. Arthritis Rheum. 2012;64(Suppl 10):1632.
   PubMed Web of Science ®Google Scholar
• Dalbeth N, Stamp L. Hyperuricaemia and gout: time for a new staging system? Ann Rheum Dis. 2014;73:1598–1600.
   PubMed Web of Science ®Google Scholar
• Edwards NL, So A. Emerging therapies for gout. Rheum Dis Clin North Am. 2014;40:375–387.
   PubMed Web of Science ®Google Scholar
• Ahn SO, Horiba N, Ohtomo S, et al. SAT0356 The therapeutic efficacy of the novel uricosuric agent UR-1102 for hyperuricemia and gout. Ann Rheum Dis. 2014;72(Suppl 3):A704.
   Google Scholar
• Warrell Jr RP, Klukovits A, Barnes K, et al. Profound hypouricemia induced in human subjects by novel bifunctional inhibitors of xanthine oxidase and URAT1. Arthritis Rheum. 2014;66:S366.
   Web of Science ®Google Scholar
• A clinical proof-of-concept study investigating the biochemical effect of RLBN1001 in patients with gout. Available from: http://adisinsight.springer.com/trials/700260269
   Google Scholar
• Noveck R, Wang Z, Forsthoefel A, et al. Levotofisopam has uricosuric activity and reduces serum urate levels in patients with gout. Arthritis Rheum. 2012;64(Suppl 10):818.
   Google Scholar
• Ardea Biosciences, Inc. Thioacetate compounds, compositions and methods of use. WO2011159839. 2012.
   Google Scholar
• Ardea Biosciences, Inc. Phenylthioacetate compounds, compositions and methods of use. WO2011159840. 2012.
   Google Scholar
• Pfizer Inc. New salt and medical use. WO2013057722. 2013.
   Google Scholar
• Norinder U, Ek ME. QSAR investigation of NaV1.7 active compounds using the SVM/Signature approach and the Bioclipse modeling platform. Bioorg Med Chem Lett. 2013;23:261–263.
   PubMed Web of Science ®Google Scholar
• Pfizer Inc. Sulfonamide derivatives as urat-1 inhibitors. WO2014170792. 2014.
   Google Scholar
• Pfizer Inc. Sulfonamides for the treatment of gout. WO2014170793. 2014.
   Google Scholar
• Wellstat Therapeutics Co. Benzoic acid compounds for reducing uric acid. WO2012033720. 2012.
   Google Scholar
• Wellstat Therapeutics Co. 3-Benzyloxyphenyloxoacetic acid compounds for reducing Uric acid. WO2012125533. 2012.
   Google Scholar
• Sato Pharmaceutical Co., Ltd. Ring-fused compound. WO2012102405. 2012.
   Google Scholar
• Sato Pharmaceutical Co., Ltd. Difluoromethylene compound. WO2014017643. 2014.
   Google Scholar
• J-Pharma Co., Ltd. Developing potent urate transporter inhibitors: compounds designed for their uricosuric action. WO2012048058. 2012.
   Google Scholar
• Teijin Pharma Co., Ltd. Pyridine derivative. WO2014077285. 2014.
   Google Scholar
• Teijin Pharma Co., Ltd. Preparation of (2-imidazolyl)pyrazine derivative and (2-pyrrolyl)pyrazine derivative, salt or solvate thereof, pharmaceutical composition, urate transporter 1 (URAT1) inhibitor, and therapeutic agent or preventive agent. WO2015174417. 2015.
   Google Scholar
• Teijin Pharma Co., Ltd. Preparation of imidazole derivatives as urate transporter 1 (URAT1) inhibitors. JP2015214527. 2015.
   Google Scholar
• Teijin Pharma Co., Ltd. Preparation of pyrazine-substituted imidazoles as urate transporter 1 (URAT1) inhibitors. JP2015214523. 2015.
   Google Scholar
• Teijin Pharma Co., Ltd. Preparation of 2-(5-chloropyridin-3-yl)-1-(2,5-dichlorobenzyl)-4-methyl-1H-imidazole-5-carboxylic acid crystals, URAT1 inhibitors, and pharmaceutical compositions containing them. WO2015174411. 2015.
   Google Scholar
• Taisho Pharmaceutical Co., Ltd. Composition for regulating URAT1 activity. WO2013018706. 2013.
   Google Scholar
• Kissei Pharmaceutical Co., Ltd. Fused heterocyclic compounds as xanthine oxidase inhibitors and pharmaceuticals containing them for treatment of hyperuricemia and its related disorders. WO2013027801. 2013.
   Google Scholar
• Shanghai HengRui Pharm Co., Ltd., Jiangsu HengRui Medicin Co. Cycloalkyl acid derivative, preparation method thereof, and pharmaceutical application thereof. WO2014183555. 2014.
   Google Scholar
• Peng J, Hu Q, Gu C, et al. Discovery of potent and orally bioavailable inhibitors of human uric acid transporter 1 (hURAT1) and binding mode prediction using homology model. Bioorg Med Chem Lett. 2016;26:277–282.
   PubMed Web of Science ®Google Scholar
• Shenyang Pharmaceutical University and Santa (ZhangJiakou) Pharmaceutical Co., Ltd. 2-ethyl-3-(4-hydroxy) benzoyl benzofuran compounds and compositions and preparation methods of compounds. CN102718735. 2014.
   Google Scholar
• Yuanqiang Z. H-Tetrazole-1-acetic acid compound containing nitrile grouping and preparation method and purpose thereof. CN104230833. 2014.
   Google Scholar
• Yuanqiang Z. Nitro containing and halogen benzene substituted 1H-tetrazole-1-acetic acid structure, and preparation method and use thereof. CN104262277. 2015.
   Google Scholar
• Yuanqiang Z. Nitro-containing tetrazoleacetic acid compounds as well as preparation method and application of nitro-containing tetrazoleacetic acid compounds. CN104292175. 2015.
   Google Scholar
• Yuanqiang Z. Tetrazoleacetic acid compounds containing halogenobenzene as well as preparation method and application of tetrazoleacetic acid compounds. CN104292176. 2015.
   Google Scholar
• Yuanqiang Z. Tetrazoleacetic acid compounds containing cyano and halobenzene substituent as well as preparation method and application of tetrazoleacetic acid compounds. CN104292177. 2015.
   Google Scholar
• Yuanqiang Z. Compounds containing tetrazoleacetic acids as well as preparation method and application of compounds. CN104292178. 2015.
   Google Scholar
• Yuanqiang Z. Tetrazoleacetic acid compound, as well as preparation method and applications thereof. CN104341367. 2015.
   Google Scholar
• Yuanqiang Z. Succinic acid amide derivatives containing phenylnaphthalene rings as well as preparation method and application thereof. CN104292123. 2015.
   Google Scholar
• Yuanqiang Z. Succinic acid amide derivatives containing nitrophenyl-substituted naphthalene rings as well as preparation method and application thereof. CN104292124. 2015.
   Google Scholar
• Yuanqiang Z. Nitro-substituted triazole sulfinyl malonate type compound, and preparation method and application thereof. CN104326993. 2015.
   Google Scholar
• Yuanqiang Z. Nitrile-substituted triazole sulfonyl malonate type compound, and preparation method and application thereof. CN104326994. 2015.
   Google Scholar
• Yuanqiang Z. Nitrile-substituted triazole malonate type compound, and preparation method and application thereof. CN104326995. 2015.
   Google Scholar
• Yuanqiang Z. Nitro-substituted triazole malonate type compound, and preparation method and application thereof. CN104326996. 2015.
   Google Scholar
• Yuanqiang Z. Alkoxy-substituted triazole malonate type compound, and preparation method and application thereof. CN104326997. 2015.
   Google Scholar
• Yuanqiang Z. Phenyl-substituted triazole malonate type compound, and preparation method and application thereof. CN104326998. 2015.
   Google Scholar
• Yuanqiang Z. Alkoxy-substituted triazole sulfinyl malonate type compound, and preparation method and application thereof. CN104326999. 2015.
   Google Scholar
• Yuanqiang Z. Phenyl-substituted triazole sulfinyl malonate type compound, and preparation method and application thereof. CN104327000. 2015.
   Google Scholar
• Yuanqiang Z. Cyano-substituted triazolesulfonylmalonic acid compounds as well as preparation method and application thereof. CN104341361. 2015.
   Google Scholar
• Yuanqiang Z. Triazolesulfonylmalonic acid compounds as well as preparation method and application thereof. CN104341362. 2015.
   Google Scholar
• Yuanqiang Z. Nitro-substituted triazolesulfonylmalonic acid compounds as well as preparation method and application thereof. CN104341363. 2015.
   Google Scholar
• Yuanqiang Z. Triazole malonic acid compounds as well as preparation method and application thereof. CN104341364. 2015.
   Google Scholar
• Yuanqiang Z. Halogenated triazole malonic acid compounds as well as preparation method and application thereof. CN104341365. 2015.
   Google Scholar
• Yuanqiang Z. Halotriazolesulfinylmalonic acid compounds as well as preparation method and application thereof. CN104370843. 2015.
   Google Scholar
• Yuanqiang Z. Triazolesulfinylmalonic acid compounds as well as preparation method and application thereof. CN104370841. 2015.
   Google Scholar
• Ardea Biosciences, Inc. Polymorphic, crystalline and mesophase forms of sodium 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-ylthio) acetate, and uses thereof. WO2011085009. 2011.
   Google Scholar
• Ardea Biosciences, Inc. Polymorphic forms of 2-(5-bromo-4-(4- cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-ylthio) acetic acid and uses thereof. WO2012092395. 2012.
   Google Scholar
• Crystal Pharmatech Co. Ltd., Suzhou Pengxu Pharmatech Co. Ltd. Novel salts and co-crystals of lesinurad. WO2015095703. 2015.
   Google Scholar
• Crystal Pharmatech Co. Ltd., Suzhou Pengxu Pharmatech Co. Ltd. Crystalline forms of lesinurad and its sodium salt. WO2015075561. 2015.
   Google Scholar
• Wempe MF, Jutabha P, Quade B, et al. Developing potent human uric acid transporter 1 (hURAT1) inhibitors. J Med Chem. 2011;54:2701–2713.
   PubMed Web of Science ®Google Scholar
• Uetake D, Ohno I, Ichida K, et al. Effect of fenofibrate on uric acid metabolism and urate transporter 1. Intern Med. 2010;49:89–94.
   PubMed Web of Science ®Google Scholar
• Tan PK, Hyndman D, Miner JN. SAT0521 Lesinurad, an inhibitor of the uric acid transporter URAT1 and a potential therapy for gout, requires URAT1 phenylalanine 365 for high affinity inhibition. Ann Rheum Dis. 2014;73(Suppl 2):780.
   PubMed Web of Science ®Google Scholar
• Patel YT. Development of a preclinical tool for evaluating uricosuric activity in the isolated perfused rat kidney [dissertation]. Brookville (NY): Long Island University; 2013.
   Google Scholar
• Human Cell Systems, Inc. Method of screening for therapeutic compounds for vascular disorders and hypertension based on URAT1 activity modulation. US8236488. 2012.
   Google Scholar
• Wempe MF, Quade B, Jutabha P, et al. Human uric acid transporter 1 (hURAT1): an inhibitor structure-activity relationship (SAR) study. Nucleos Nucleot Nucl. 2011;30:1312–1323.
   PubMed Web of Science ®Google Scholar
• Wempe MF, Lightner JW, Miller B, et al. Potent human uric acid transporter 1 inhibitors: in vitro and in vivo metabolism and pharmacokinetic studies. Drug Des Devel Ther. 2012;6:323–339.
   PubMed Web of Science ®Google Scholar
• Hosoyamada M, Takiue Y, Morisaki H, et al. Establishment and analysis of SLC22A12 (URAT1) knockout mouse. Nucleos Nucleot Nucl. 2010;29:314–320.
   PubMed Web of Science ®Google Scholar
• Sugihara S, Hisatome I, Kuwabara M, et al. Depletion of uric acid due to SLC22A12 (URAT1) loss-of-function mutation causes endothelial dysfunction in hypouricemia. Circ J. 2015;79:1125–1132.
   PubMed Web of Science ®Google Scholar
• Nakanishi T, Ohya K, Shimada S, et al. Functional cooperation of URAT1 (SLC22A12) and URATv1 (SLC2A9) in renal reabsorption of urate. Nephrol Dial Transplant. 2013;28:603–611.
   PubMed Web of Science ®Google Scholar
• Nanjing University. Application of curcumin in the preparation of medicament for uric acid transportor URAT1 inhibitor. CN100571692. 2009.
   Google Scholar
• Nanjing University. Application of Huaimi flavonoids extract in the preparation of medicament for uric acid transporter URAT1 inhibitor. CN101181345. 2011.
   Google Scholar
• An G, Liu W, Duan WR, et al. Population pharmacokinetics and exposure-uric acid analyses after single and multiple doses of ABT-639, a calcium channel blocker, in healthy volunteers. Aaps J. 2015;17:416–426.
   PubMed Web of Science ®Google Scholar
• The University of Tokyo, Tokyo University of Pharmacy and Life Sciences. Method for evaluating urate transport-related disease factor and inflammation-related disease factor. US20150080257. 2015.
   Google Scholar
• Eraly SA, Liu HC, Jamshidi N, et al. Transcriptome-based reconstructions from the murine knockout suggest involvement of the urate transporter, URAT1 (slc22a12), in novel metabolic pathways. Biochem Biophys Rep. 2015;3:51–61.
   PubMedGoogle Scholar