775
Views
193
CrossRef citations to date
0
Altmetric
Reviews

Sulfonamides: a patent review (2008 – 2012)

, &
Pages 747-758 | Published online: 15 Jun 2012

Bibliography

  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168-81
  • Smith RE, Ashiya M. Antihypertensive therapies. Nat Rev Drug Discov 2007;6:597-8
  • Supuran CT, Casini A, Scozzafava A. Development of sulfonamide carbonic anhydrase inhibitors. In: Supuran CT, Scozzafava A, Conway J, editors. Carbonic anhydrase - its inhibitors and activators. CRC Press; Boca Raton (FL), USA, 2004. p. 67-148
  • Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146-89
  • Supuran CT. Carbonic anhydrases as drug targets – an overview. Curr Top Med Chem 2007;7:825-33
  • Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. Anticancer and antiviral sulfonamides. Curr Med Chem 2003;10:925-53
  • Supuran CT, Briganti F, Tilli S, Carbonic anhydrase inhibitors. Sulfonamides as antitumor agents? Bioorg Med Chem 2001;9:703-14
  • Casini A, Scozzafava A, Supuran CT. Sulfonamide derivatives with protease inhibitory action as anticancer, antiinflammatory and antiviral agents. Expert Opin Ther Patents 2002;12:1307-27
  • Supuran CT. Indisulam - an anticancer sulfonamide in clinical development. Expert Opin Investig Drugs 2003;12:283-7
  • Cecchi A, Hulikova A, Pastorek J, Carbonic anhydrase inhibitors. Design of fluorescent sulfonamides as probes of tumor-associated carbonic anhydrase IX that inhibit isozyme IX-mediated acidification of hypoxic tumors. J Med Chem 2005;48:4834-41
  • Weber A, Casini A, Heine A, Unexpected nanomolar inhibition of carbonic anhydrase by COX-2-selective celecoxib: new pharmacological opportunities due to related binding site recognition. J Med Chem 2004;47:550-7
  • Carta F, Supuran CT, Scozzafava A. Novel therapies for glaucoma: a patent review 2007-2011. Expert Opin Ther Patents 2012;22:79-88
  • Fabrizi F, Mincione F, Somma T, A new approach to antiglaucoma drugs: carbonic anhydrase inhibitors with or without NO donating moieties. Mechanism of action and preliminary pharmacology. J Enzyme Inhib Med Chem 2012;27:138-47
  • Basnyat B, Gertsch JH, Johnson EW, Efficacy of low-dose acetazolamide (125 mg BID) for the prophylaxis of acute mountain sickness: a prospective, double-blind, randomized, placebo-controlled trial. High Alt Med Biol 2003;4:45-52
  • Matthews E, Portaro S, Ke Q, Acetazolamide efficacy in hypokalemic periodic paralysis and the predictive role of genotype. Neurology 2011;77:1960-4
  • Temperini C, Innocenti A, Mastrolorenzo A, Carbonic anhydrase inhibitors. Interaction of the antiepileptic drug sulthiame with twelve mammalian isoforms: kinetic and X-Ray crystallographic studies. Bioorg Med Chem Lett 2007;17:4866-72
  • De Simone G, Di Fiore A, Menchise V, Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: solution and X-ray crystallographic studies. Bioorg Med Chem Lett 2005;15:2315-20
  • Abbate F, Coetzee A, Casini A, Carbonic anhydrase inhibitors. X ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride. Bioorg Med Chem Lett 2004;14:337-41
  • Di Fiore A, Pedone C, D’Ambrosio K, Carbonic anhydrase inhibitors. Valdecoxib binds to a different active site region of the human isoform II as compared to the structurally related, cyclooxygenase II “selective” inhibitor celecoxib. Bioorg Med Chem Lett 2006;16:437-42
  • Dogne JM, Supuran CT, Pratico D. Adverse cardiovascular effects of the coxibs. J Med Chem 2005;48:2251-7
  • Supuran CT, Casini A, Mastrolorenzo A, Scozzafava A. COX-2 selective inhibitors, carbonic anhydrase inhibition and anticancer properties of sulfonamides belonging to this class of pharmacological agents. Mini Rev Med Chem 2004;4:625-32
  • Temperini C, Cecchi A, Scozzafava A, Supuran CT; Carbonic anhydrase inhibitors. Sulfonamide diuretics revisited – old leads for new applications ? Org Biomol Chem 2008;6:2499-506
  • Temperini C, Cecchi A, Scozzafava A, Supuran CT; Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide and furosemide x-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem 2009;17:1214-21
  • Temperini C, Cecchi A, Scozzafava A, Supuran CT; Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with twelve mammalian isozymes and x-ray crystallographic studies for the indapamide- isozyme II adduct. Bioorg Med Chem Lett 2008;18:2567-73
  • Temperini C, Cecchi A, Scozzafava A, Supuran CT; Carbonic anhydrase inhibitors. Comparison of chlorthalidone and indapamide X-ray crystal structures in adducts with isozyme II: when three water molecules and the keto-enol tautomerism make the difference. J Med Chem 2009;52:322-8
  • Supuran CT. Diuretics: from classical carbonic anhydrase inhibitors to novel applications of the sulfonamides. Curr Pharm Des 2008;14:641-8
  • . Patel A; ADVANCE Collaborative GroupMacMahon S, Chalmers J, Effects of a fixed combination of perindopril and indapamide on macrovascular and microvascular outcomes in patients with type 2 diabetes mellitus (the ADVANCE trial): a randomised controlled trial. Lancet 2007;370:829-40
  • Piecha G, Adamczak M, Chudek J, Wiecek A. Indapamide decreases plasma adiponectin concentration in patients with essential hypertension. Kidney Blood Press Res 2007;30:187-94
  • Bukowski RM, Yasothan U, Kirkpatrick P. Pazopanib. Nat Rev Drug Discov 2010;9:17-18
  • Sugrue MF. The pharmacology of antiglaucoma drugs. Pharmacol Ther 1989;43:91-138
  • Mincione F, Menabuoni L, Supuran CT. Clinical applications of the carbonic anhydrase inhibitors in ophthalmology. In: Supuran CT, Scozzafava A, Conway J, editors. Carbonic anhydrase – its inhibitors and activators. CRC Press; Boca Raton (FL): 2004. p. 243-54
  • Mincione F, Scozzafava A, Supuran CT. Antiglaucoma carbonic anhydrase inhibitors as ophthalomologic drugs. In: Supuran CT, Winum JY, editors. Drug design of zinc-enzyme inhibitors: functional, structural, and disease applications. Wiley; Hoboken, 2009. p. 139-54
  • Supuran CT, Scozzafava A. Carbonic anhydrase inhibitors and their therapeutic potential. Expert Opin Ther Patents 2000;10:575-600
  • Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467-74
  • Supuran CT. Carbonic anhydrase inhibition/activation: trip of a scientist around the world in the search of novel chemotypes and drug targets. Curr Pharm Des 2010;16:3233-45
  • Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146-89
  • Steele RM, Batugo MR, Benedini F, Nitric oxide-donating carbonic anhydrase inhibitors for the treatment of open-angle glaucoma. Bioorg Med Chem Lett 2009;19:6565-70
  • Mincione F, Benedini F, Biondi S, Synthesis and crystallographic analysis of new sulfonamides incorporating NO-donating moieties with potent antiglaucoma action. Bioorg Med Chem Lett 2011;21:3216-21
  • Supuran C, Benedini F, Biondi S, Ongini E. Nitrate esters of carbonic anhydrase inhibitors. WO071421; 2008
  • Huang Q, Rui EI. Inhibitors of carbonic anhydrase. WO007814; 2009
  • Daumantas M, Virginija D, Jurgita M, Benzimidazo[1,2-c][1,2,3]Thiadiazol-7-sulfonamides as inhibitors of carbonic anhydrase and the intermediates for production thereof. WO2008016288; 2008
  • Baranauskiene L, Hilvo M, Matuliene J, Inhibition and binding studies of carbonic anhydrase isozymes I, II and IX with benzimidazo[1,2-c][1,2,3]thiadiazole-7-sulphonamides. J Enzyme Inhib Med Chem 2010;25:863-70
  • Chang JN, Hughes PM, Devries GW. Carbonic anhydrase inhibitor sustained release intraocular drug delivery systems. US2011034448; 2011
  • Gant TG. Sulfonamide inhibitors of carbonic anhydrase II. WO059846; 2011
  • Seal S, Patil SD, Haldar MK, Malik S. Functionalized nanoceria composition for ophthalmic treatment. US0268662; 2011
  • Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767-77
  • Alterio V, Hilvo M, Di Fiore A, Crystal structure of the extracellular catalytic domain of the tumor-associated human carbonic anhydrase IX. Proc Natl Acad Sci USA 2009;106:16233-8
  • Whittington DA, Waheed A, Ulmasov B, Crystal structure of the dimeric extracellular domain of human carbonic anhydrase XII, a bitopic membrane protein overexpressed in certain cancer tumor cells. Proc Natl Acad Sci USA 2001;98:9545-50
  • Ebbesen P, Pettersen EO, Gorr TA, Taking advantage of tumor cell adaptations to hypoxia for developing new tumor markers and treatment strategies. J Enzyme Inhib Med Chem 2009;24(S1):1-39
  • Svastova E, Hulikova A, Rafajova M, Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH. FEBS Lett 2004;577:439-45
  • Dubois L, Lieuwes NG, Maresca A, Imaging of CA IX with fluorescent labelled sulfonamides distinguishes hypoxic and (re)-oxygenated cells in a xenograft tumor model. Radiother Oncol 2009;92:423-8
  • Ahlskog JKJ, Dumelin CE, Trussel S, In vivo targeting of tumor-associated carbonic anhydrases using acetazolamide derivatives. Bioorg Med Chem Lett 2009;19:4851-6
  • Lou Y, McDonald PC, Oloumi A, Targeting tumor hypoxia: suppression of breast tumor growth and metastasis by novel carbonic anhydrase IX inhibitors. Cancer Res 2011;71:3364-76
  • Pacchiano F, Carta F, McDonald PC, Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis. J Med Chem 2011;54:1896-902
  • McDonald PC, Winum JY, Supuran CT, Dedhar S. Recent developments in targeting carbonic anhydrase IX for cancer therapeutics. Oncotarget 2012;3:84-97
  • Ozensoy Guler O, De Simone G, Supuran CT. Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII. Curr Med Chem 2010;17:1516-26
  • Alterio V, Vitale RM, Monti SM, Carbonic anhydrase inhibitors. X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX. J Am Chem Soc 2006;128:8329-35
  • Carta F, Garaj V, Maresca A, Sulfonamides incorporating 1,3,5-triazine moieties selectively and potently inhibit carbonic anhydrase transmembrane isoforms IX, XII and XIV over cytosolic isoforms I and II: solution and X-ray crystallographic studies. Bioorg Med Chem 2011;19:3105-19
  • Garaj V, Puccetti L, Fasolis G, Carbonic anhydrase inhibitors. Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II and IX with sulfonamides incorporating 1,2,4-triazine moieties. Bioorg Med Chem Lett 2004;14:5427-33
  • Garaj V, Puccetti L, Fasolis G, Carbonic anhydrase inhibitors. Novel sulfonamides incorporating 1,3,5-triazine moieties as inhibitors of the cytosolic and tumor-associated carbonic anhydrase isozymes I, II and IX. Bioorg Med Chem Lett 2005;15:3102-8
  • Owa T, Ozawa Y, Taro S. Joint use of sulfonamide based compound with angiogenesis inhibitor. EP2364699; 2011
  • Zimmerman C, Babich JW, Joyal J, Inhibitors of carbonic anhydrase IX. WO089383; 2009
  • Supuran C, Scozzafava A, Pastorekova S, Pastorek J. CA IX-specific inhibitors. US7829065; 2010
  • Supuran C, Scozzafava A, Pastorekova S, Pastorek J. CA IX-specific inhibitors. US7833734; 2010
  • Supuran C, Scozzafava A, Pastorekova S, Pastorek J. CA IX-specific inhibitors. US7833737; 2010
  • Supuran C, Scozzafava A, Pastorekova S, Pastorek J. CA IX-specific inhibitors. US7833738; 2010
  • Supuran C, Scozzafava A, Pastorekova S, Pastorek J. CA IX-specific inhibitors. US7833739; 2010
  • Supuran C, Scozzafava A, Pastorekova S, Pastorek J. CA IX-specific inhibitors. US7833514; 2010
  • Supuran C, Dedhar S, McDonald P, Carta F. Novel sulfonamide compounds for inhibition of metastatic tumor growth. WO021963; 2012
  • Abbate F, Casini A, Owa T, Carbonic anhydrase inhibitors. E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. Bioorg Med Chem Lett 2004;14:217-23
  • Scozzafava A, Menabuoni L, Mincione F, Carbonic anhydrase inhibitors. Part 74. Synthesis of water-soluble, topically effective, intraocular pressure-lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: is the tail more important than the ring? J Med Chem 1999;42:2641-50
  • Scozzafava A, Menabuoni L, Mincione F, Carbonic anhydrase inhibitors. Perfluoroalkyl/aryl-substituted derivatives of aromatic/heterocyclic sulfonamides as topical intraocular pressure lowering agents with prolonged duration of action. J Med Chem 2000;43:4542-51
  • Scozzafava A, Menabuoni L, Mincione F, Carbonic anhydrase inhibitors. Synthesis of sulfonamides incorporating dtpa tails and of their zinc complexes with powerful topical antiglaucoma properties. Bioorg Med Chem Lett 2001;11:575-82
  • Scozzafava A, Menabuoni L, Mincione F, Supuran CT; Carbonic anhydrase inhibitors. A general approach for the preparation of water soluble sulfonamides incorporating polyamino-polycarboxylate tails and of their metal complexes possessing long lasting, topical intraocular pressure lowering properties. J Med Chem 2002;45:1466-76
  • Can D, Spingler B, Schmutz P, [(Cp-R)M(CO)3] (M = Re or 99mTc) Arylsulfonamide, -sulfamide, and -sulfamate conjugates for selective targeting of human carbonic anhydrase IX. Angew Chem Intl Ed Engl 2012; In press
  • Supuran CT, Scozzafava A, Ilies MA, Carbonic anhydrase inhibitors. Part 53. Synthesis of substituted-pyridinium derivatives of aromatic sulfonamides: the first non-polymeric membrane-impermeable inhibitors with selectivity for isozyme IV. Eur J Med Chem 1998;33:577-94
  • Scozzafava A, Briganti F, Ilies MA, Supuran CT; Carbonic anhydrase inhibitors. Synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus the cytosolic isozymes. J Med Chem 2000;43:292-300
  • Casey JR, Morgan PE, Vullo D, Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX. J Med Chem 2004;47:2337-47
  • Pacchiano F, Aggarwal M, Avvaru BS, Selective hydrophobic pocket binding observed within the carbonic anhydrase II active site accommodate different 4-substituted-ureido-benzenesulfonamides and correlate to inhibitor potency. Chem Commun (Cambridge) 2010;46:8371-3
  • Hewitson KS, Supuran CT. Carbonic anhydrase inhibitors for treating dandruff and related disorders. WO061185; 2010
  • Hewitson KS, Vullo D, Scozzafava A, Molecular cloning, characterization and inhibition studies of a beta-carbonic anhydrase from malassezia globosa, a potential antidandruff target. J Med Chem 2012;55:3513-20
  • Zaknoen S, Lawhon T. Methods and compositions for the treatment of cancer, tumors, and tumor-related disorders. WO070546; 2009
  • Mandal PK, Freiter EM, Bagsby AL, Efficient synthesis of apricoxib, CS-706, a selective cyclooxygenase-2 inhibitor, and evaluation of prostaglandin E2 production in inflammatory breast cancer cells. Bioorg Med Chem Lett 2011;21:6071-3
  • Supuran CT, Scozzafava A. Protein tyrosine kinase inhibitors as anticancer agents. Expert Opin Ther Patents 2004;14:25-53
  • Sun L, McMahon G. Inhibition of tumor angiogenesis by synthetic receptor tyrosine kinase inhibitors. Drug Dev Today 2000;5:344-53
  • Fabbro D, Parkinson D, Matter A. Protein tyrosine kinase inhibitors: new treatment modalities? Curr Opin Pharmacol 2002;2:374-81
  • Parkkila S, Innocenti A, Kallio H, The protein tyrosine kinase inhibitors imatinib and nilotinib strongly inhibit several mammalian alpha-carbonic anhydrase isoforms. Bioorg Med Chem Lett 2009;19:4102-6
  • Supuran CT, Parkkila S. Treatment of mammalian disorders mediated by alpha-carbonic anhydrase isoforms. WO139678; 2010
  • Schutz FA, Choueiri TK, Sternberg CN. Pazopanib: clinical development of a potent anti-angiogenic drug. Crit Rev Oncol Hematol 2011;77:163-71
  • Kumar R, Pandite AN. Pyrimidin derivatives for the treatment of multiple myeloma. WO020564; 2006
  • Di Lorenzo G, Buonerba C, Biglietto M, The therapy of kidney cancer with biomolecular drugs. Cancer Treat Rev 2010;36(Suppl 3):S16-20
  • Yau T, Chen PJ, Chan P, Phase I dose-finding study of pazopanib in hepatocellular carcinoma: evaluation of early efficacy, pharmacokinetics, and pharmacodynamics. Clin Cancer Res 2011;17:6914-23
  • Kasper B, Hohenberger P. Pazopanib: a promising new agent in the treatment of soft tissue sarcomas. Future Oncol 2011;7:1373-83
  • Amiri-Kordestani L, Tan AR, Swain SM. Pazopanib for the treatment of breast cancer. Expert Opin Investig Drugs 2012;21:217-25
  • Thakur A, Scheinman RI, Rao VR, Kompella UB. Pazopanib, a multitargeted tyrosine kinase inhibitor, reduces diabetic retinal vascular leukostasis and leakage. Microvasc Res 2011;82:346-50
  • McLaughlin MM, Wurzelmann JI, Xu CF. Treatment method. WO009016; 2011
  • Xu CF. Merthods and administration of treatment. WO039648; 2011
  • Gidwani RM, Hiremath C. 5-(4-(N-(2,3-dimethyl-2H-indazol-6-yl)-N-methylamino)pyrimidin-2-yl-amino)-2-methylbenzenesulfonamide. WO058179; 2011
  • Paul EM, Suttle AB. Merthods of administration and treatment. WO146458; 2011
  • Kumar R. Combination. WO150044; 2011
  • Kumar R. Combination of BRAF and VEGF inhibitors. WO036919; 2012
  • Damian-Iordache V, King A, McLaughlin MM, Suttle AB. Treatment method. WO085007; 2011

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.