358
Views
32
CrossRef citations to date
0
Altmetric
Review

New substituted benzimidazole derivatives: a patent review (2013 – 2014)

, & , PhD (Professor)

Bibliography

  • Fei F, Zhou ZM. New substituted benzimidazole derivatives: a patent review (2010-2012). Expert Opin Ther Pat 2014;23:1157-79
  • Shah K, Chhabra S, Shrivastava SK, et al. Benzimidazole: a promising pharmacophore. Med Chem Res 2013;22:5077-104
  • Meng JP, Di RX, Zhou HC, et al. Development in benzimidazole drugs research. Chin J New Drugs 2009;18:1504-5
  • McKeown SR, Cowen RL, Williams KJ. Bioreductive drugs: from concept to clinic. Clin Oncol 2007;19:427-42
  • Błaszczak-Świątkiewicz K, Mirowski M, Kaplińska K, et al. New benzimidazole derivatives with potential cytotoxic activity study of their stability by RP-HPLC. Acta Biochim Pol 2012;59:279-88
  • Abdel-Aziz HA, Saleh TS, El-Zahabi HS. Facile synthesis and in-vitro antitumor activity of some pyrazolo[3,4-b]pyridines and pyrazolo[1,5-a]pyrimidines linked to a thiazolo[3,2-a]benzimidazole moiety. Arch Pharm (Weinheim) 2010;343:24-30
  • Hedidi M, Bentabed-Ababsa G, Derdour A, et al. Synthesis of C,N’-linked bis-heterocycles using a deprotometalation-iodination-N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells. Bioorg Med Chem 2014;22:3498-507
  • Nofal ZM, Srour AM, El-Eraky WI, et al. Rational design, synthesis and QSAR study of vasorelaxant active 3-pyridinecarbonitriles incorporating 1H-benzimidazol-2-yl function. Eur J Med Chem 2013;60:14-21
  • Abou-Seri SM, Abouzid K, Abou Ei Ella DA. Molecular modeling study and synthesis of quinazolinone-arylpiperazine derivatives as alpha1-adrenoreceptor antagonists. Eur J Med Chem 2011;46:647-58
  • Wang JL, Zhang J, Zhou ZM, et al. Design, synthesis and biological evaluation of 6-substituted aminocarbonyl benzimidazole derivatives as nonpeptidic angiotensin II AT1 receptor antagonists. Eur J Med Chem 2012;49:183-90
  • Zhang J, Wang JL, Zhou ZM, et al. Design, synthesis and biological activity of 6-substituted carbamoyl benzimidazoles as new nonpeptidic angiotensin II AT1 receptor antagonists. Bioorg Med Chem 2012;20:4208-16
  • Zhang J, Wang JL, Yu WF, et al. Nonpeptidic angiotensin II AT1 receptor antagonists derived from 6-substituted aminocarbonyl and acylamino benzimidazoles. Eur J Med Chem 2013;69:44-54
  • Goker H, Tebrizli E, Abbasoglu U. Benzimidazole-5(6)-carboxamides and evaluation of their antimicrobial activity. Farmaco 1996;51:53-8
  • Ozden S, Karatas H, Yıldız S, et al. Synthesis and potent antimicrobial activity of some novel 4-(5,6-Dichloro-1H-benzimidazole-2-yl)-N-substituted benzamides. Arch Pharm (Weinheim) 2004;337:556-62
  • Weidner-Wells MA, Ohemeng KA, Nguyen VN, et al. Amidino benzimidazole inhibitors of bacterial two-component systerms. Bioorg Med Chem Lett 2001;11:1545-8
  • Orhan Püsküllü M, Yıldız S, Goker H. Synthesis and antistaphylococcal activity of N-substituted-1H-benzimidazole-sulphonamides. Arch Pharm (Weinheim) 2010;343:31-9
  • Biava M, Porretta GC, Poce G, et al. 1,5-Diaryl-2-ethyl pyrrole derivatives as antimycobacterial agents: design, synthesis, and microbiological evaluation. Eur J Med Chem 2009;44:4734-8
  • Gill C, Janesh G, Shaikh M, et al. Clubbed [1, 2, 3] triazoles by fluorine benzimidazole: a novel approach to H37Rv inhibitors as a potential treatment for tuberculosis. Bioorg Med Chem Lett 2008;18:6244-7
  • Pandey J, Tiwari VK, Verma SS, et al. Synthesis and antitubercular screening of imidazole derivatives. Eur J Med Chem 2009;44:3350-5
  • Karuvalam Ranjith P, Rajeesh P, Haridas KR, et al. Design and synthesis of positional isomers of 5 and 6-bromo-1-[(phenyl)sulfonyl]-2-[(4-nitrophenoxy)methyl]-1Hbenzimidazoles as possible antimicrobial and antitubercular agents. Bioorg Med Chem Lett 2013;23:5228-34
  • Saify ZS, Kamran Azim M, Ahmad W, et al. New benzimidazole derivatives as antiplasmodial agents and plasmepsin inhibitors: synthesis and analysis of structure–activity relationships. Bioorg Med Chem Lett 2012;22:1282-6
  • Camacho J, Barazarte A, Gamboa N, et al. Synthesis and biological evaluation of benzimidazole-5-carbohydrazide derivatives as antimalarial, cytotoxic and antitubercular agents. Biorg Med Chem 2011;19:2023-9
  • Soria-Arteche O, Hernández-Campos A, Yépez-Mulia L, et al. Synthesis and antiprotozoal activity of nitazoxanide-N-methylbenzimidazole hybrids. Bioorg Med Chem Lett 2013;22:6838-41
  • Yan Y, Liu ZJ, Zhang JJ, et al. A reverse method for diversity introduction of benzimidazole to synthesize H+/K+-ATP enzyme inhibitors. Bioorg Med Chem Lett 2011;21:4189-92
  • Shen HC, Ding FX, Zhou CY, et al. Discovery of benzimidazole pyrrolidinyl amides as prolylcarboxypeptidase inhibitors. Bioorg Med Chem Lett 2011;21:1299-305
  • Kankala S, Kankala RK, Gundepaka P, et al. Regioselective synthesis of isoxazole-mercaptobenzimidazole hybrids and their in vivo analgesic and anti-inflammatory activity studies. Bioorg Med Chem Lett 2013;23:1306-9
  • Vangavaragu JR, Valasani KR, Gan XQ, et al. Identification of human presequence protease (hPreP) agonists for the treatment of Alzheimer’s disease. Eur J Med Chem 2014;76:506-16
  • Hu E, Kunz RK, Chen N, et al. Design, optimization, and biological evaluation of novel keto-benzimidazoles as potent and selective inhibitors of phosphodiesterase 10A (PDE10A). J Med Chem 2013;56:8781-92
  • Herbert W, Gemma T, Alfred W, et al. Benzimidazoles for the treatment of cancer. EP2698367; 2014
  • Lelais G, Epple R, Michillys PY, et al. Compounds and compositions for modulating EGFR activity. WO184766; 2013
  • Chen Y, Chen Y. Novel therapeutic agents. WO113841; 2013
  • Rivero RA, Tedesco R, Luengo JI. Benzimidazole boronic acid derivatives as PI3 kinase inhibitors. US0157977; 2013
  • Staehle W, Schultz M, Schiemann K. N-(benzimimdazol-2-yl)-cyclopropane carboxamides as lysophosphatidic acid antagonists. WO020622; 2013
  • Zhou Y, Zhang LR, Zhou J, et al. Use of benzo five-membered nitrogen heterocyclic piperazine or piperidine derivatives. WO079155; 2014
  • Ge J, Ma JY, Xiang YG, et al. Benzimidazole derivatives, preparation method and medicinal use thereof. CN103709154; 2014
  • Hachtel S, Wohlfart P, Weston J, et al. Benzimidazole-carboxylic acid amide derivatives as APJ receptor modulators. WO044738; 2014
  • Zhou ZM, Xu D, He X, et al. Chiral ((4-methyl-2-propyl-1H-benzimidazole-6-amide)-1-radical) methyl diphenyl compound, as well as preparation method and application thereof. CN102491971; 2012
  • Ojima I. Benzimidazoles and uses thereof. WO116823; 2013
  • Weibel DB, Eun YJ, Zhou MQ. Antimicrobial compositions and methods of use thereof. US0018079; 2013
  • Wang BX, Jiang YL, Zhou WL. 4H-pyrrolo[1, 2-a] benzimidazole derivative and synthesizing method and application thereof. CN102924460; 2013
  • Chen Y, Nichols D, Renslo A, et al. Compositions, methods of use, and methods of treatment. WO103760; 2013
  • Waters C, Sambanthamoorthy K, Neiditch M, et al. Benzimidazole inhibition of biofilm formation. US0345261; 2013
  • Zhang SM. Flavonoids or isoflavonoids compounds and uses thereof. WO121590; 2014
  • Chen Q, Lopez OD, Bender JA, et al. Hepatitis C virus inhibitors. US0121957; 2013
  • Scott RW, Vitale JP, Matthews KS, et al. Synthesis of antiviral compound. US20130324740; 2013
  • Qiu YL, Wang C, Peng XW, et al. Novel benzimidazole derivatives. WO052369; 2013
  • Feng S, Gao L, Hong D, et al. Novel indazoles for the treatment and prophylaxis of respiratory syncytial virus infection. WO009302; 2014
  • Gomtsian A, Dekhtyar T, Frank KE, et al. Cyanoguanidines and their use as antiviral agents. WO005129; 2014
  • Cockerill S, Pilkington C, Lumley J, et al. Pharmaceutical compounds. WO068769; 2013
  • De Grado WF, Wang JZ, Wang J, et al. Inhibitors targeting drus-resistant influenza A. WO086131; 2013
  • Luo XJ. Method for preparing benzimidazole heterocyclic compound. CN103087044; 2013
  • Gurjar MK, Maikap GS, Tripathy NK, et al. Pyridone derivatives as acid secretion inhibitors and process for preparation thereof. WO080422; 2014
  • Yang YJ, Li ZL. Synthesis method of Lansoprazole and Lansoprazole synthesized thereby. CN103288799; 2013
  • Eckhardt M, Langkopf E, Wagner H. Indanyloxydihydrobenzofuranylacetic acids. US0148462; 2014
  • Apgar JM, Biftu T, Chen P, et al. Novel benzimidazole tetrahydrofuran derivatives. WO031441; 2014
  • Apgar JM, Biftu T, Chen P, et al. Novel benzimidazole derivatives. WO031445; 2014
  • Devita RJ, Yu Y, Liu J, et al. Compounds as DGAT-1 inhibitors. WO130370; 2013
  • Kasal S, Igawa H, Takahashi M, et al. Benzimidazole derivatives as MCH receptor antagonists. WO105676; 2013
  • Kamenecka TM, Griffin PR. N-biphenylmethylbenzimidazole modulators of PPARG. WO078240; 2013
  • Kamenecka TM, Griffin PR. N-biphenylmethylbenzimidazole modulators of PPARG. WO078233; 2013
  • Liu J, Balkovec JM, Krikorian AD, et al. Imidazole derivatives. WO074387; 2013
  • Wang HY, Zhu WL, Cai HY, et al. Application of 2,4,6-triisopropylbenzene compounds in preparation of medicines for treating diabetes. CN103040815; 2013
  • Hua EB, Jia SL, Wang QY. Benzimidazole derivative, and preparation method and application thereof. CN102942562; 2013
  • Gharat LA, Muthukaman N, Deshmukh S, et al. Tricyclic compounds as mPGES-1 inhibitors. WO153535; 2013
  • Hadida-Ruah SS, Grootenhuis PDJ, Miller MT, et al. Benzoxazines as modulators of ion channels. WO067248;2013
  • Bagal SK, Brown AD, Kemp MI, et al. Benzimidazole and imidazopyridine derivatives as sodium channel modulators. WO114250; 2013
  • Pae AN, Min SJ, Roh EJ, et al. Benzimidazole derivatives as mitochondrial function modulators. US0114067; 2014
  • Ceccarelli SM, Jagasia R, Jakobroetne R, et al. Benzimidazoles as CNS active agents. WO053409; 2014
  • Geneste H, Ochse M, Drescher K, et al. Novel inhibitor compounds of phosphodiesterase type 10A. US0116233; 2013
  • Beshore DC, Culberson C, Johnson AW, et al. Azetidine benzimidazoles as PDE10 inhibitors. WO078214; 2014
  • Kuduk SD, Mccomas CC, Reger TS. Cyclobutyl benzimidazoles as PDE10 inhibitor. WO078216; 2014
  • Luo HR, Hong XC, Deng ZX, et al. Benzimidazole and derivative thereof, and medicinal composition and application thereof. CN103121969; 2013
  • Duncan KM, Chesworth R, Boriack-sjodin PA, et al. PRMT5 inhibitors containing a dihydro- or tetrahydroisoquinoline and uses thereof. WO100730; 2014
  • Czardybon W, Brzόzka K, Galezowski M, et al. Novel benzimidazole derivatives as kinase inhibitors. WO096388; 2014
  • Rzymski T, Zarebski A, Dreas A, et al. Substituted tricyclic benzimidazoles as kinase inhibitors. WO072435; 2014
  • Dickman DA, Kumar DV, O’bryan C, et al. Factor VIIA inhibitor. US8729117; 2014
  • Brameld KA, Owens TA. Benzimidazole derivatives as ITK inhibitors. WO036016; 2014
  • Chaudhari SS, Thomas A, Adik BG, et al. Novel urea derivatives as TEC kinase inhibitors and uses thereof. WO024427; 2013
  • Boss C, Brotschi C, Gude M, et al. Benzimidazole-proline derivatives. WO182972; 2013
  • Brooks C, Cheung M, Eidam HS, et al. TRPV4 antagonists. WO012500; 2013
  • Bray M, Driscoll J, Huggins JW. Treatment of lethal Ebola virus infection in mice with a single dose of an S-adenosyl-L-homocysteine hydrolase inhibitor. Antiviral Res 2000;45:135-47
  • Chong CR, Chen XC, Shi LR, et al. A clinical drug library screen identifies astemizole as an antimalarial agent. Nat Chem Biol 2006;2:415-16
  • Vorperian VR, Zhou ZF, Mohammad S, et al. Torsade de pointes with an antihistamine metabolite: potassium channel blockade with Desmethylastemizole. J Am Coll Cardiol 1996;28:1556-61
  • Barrett IC, Kerr MA. The high-pressure SNAr reaction of N-p-fluorobenzyl-2- chlorobenzimidazole with amines; an approach to Norastemizole and analogues. Tetrahedron Lett 1999;40:2439-42
  • Bhalerao DS, Kondaiah GCM, Dwivedi N, et al. Novel approach to the synthesis of Omeprazole: an antipeptic ulcer agent. Synthetic Commun 2010;40:2983-7
  • Metz DC, Vakily M, Dixit T, et al. Review article: dual delayed release formulation of dexlansoprazole MR, a novel approach to overcome the limitations of conventional single release proton pump inhibitor therapy. Aliment Pharmacol Ther 2009;29:928-37
  • Vora JJ, Trivedi KP, Kshatriya RS. An improved synthesis of 2-mercapto-5-difluoromethoxy-1Hbenzimidazole: an important medicinal intermediate. Adv Appl Sci Res 2011;2:89-93
  • Ishizaki T, Horai Y. Review article: cytochrome P450 and the metabolism of proton pump inhibitors-emphasis on Rabeprazole. Aliment Pharmacol Ther 1999;13:27-36
  • Wang P, Zheng GJ, Wang YP, et al. Highly practical and cost-efficient synthesis of telmisartan: an antihypertensive drug. Tetrahedron 2012;68:2509-12
  • Husain A, Azim MS, Mitra M, et al. A review on Candesartan: pharmacological and pharmaceutical profile. J Pharm Sci 2011;01:12-17
  • Wang P, Zheng GJ, Wang YP, et al. A novel and practica lsynthesis of substituted 2-ethoxybenzimidazole: candesartan cilexetil. Tetrahedron 2010;66:5402-6
  • Ojima M, Igata H, Tanaka M, et al. In vitro antagonistic properties of a new angiotensin type 1 receptor blocker, Azilsartan, in receptor binding and function studies. J Pharmacol Exp Ther 2011;336:801-8
  • Hernández-Luis F, Hernández-Campos A, Yépez-Mulia L, et al. Synthesis and hydrolytic stability studies of albendazole carrier prodrugs. Bioorg Med Chem Lett 2001;11:1359-62
  • Gokeulut C, Nolan AM, McKellar QA. Plasma disposition, faecal excretion and in vitro metabolism of oxibendazole following oral administration in horses. Res Vet Sci 2002;72:11-15
  • Dunn GL, Gallagher G, Davis LD, et al. Metabolites of methyl 5(6)-butyl-2-benzimidazolecarbamate (Parbendazole). Structure and synthesis. J Med Chem 1973;16:996-1002
  • Carlert S, Akesson P, Jerndal G, et al. In vivo dog intestinal precipitation of Mebendazole: a basic BCS class II drug. Mol Pharm 2012;9:2903-11
  • Lu J, Ge HG, Bai YJ. Solvent-free synthesis of 2-Substituted benzimidazoles under microwave-irradiation using PPA as a catalyst. Chin J Org Chem 2002;22:782-4
  • Zhang ZH, Yin L, Wang YM. An expeditious synthesis of benzimidazole derivatives catalyzed by Lewis acids. Catal Commun 2007;8:1126-31
  • Heravi MM, Sadjadi S, Oskooie HA, et al. Heteropolyacids as heterogeneous and recyclable catalysts for the synthesis of benzimidazoles. Catal Commun 2008;9:504-7
  • Zhang ZH, Li TS, Li JJ. A highly effective sulfamic acid/methanol catalytic system for the synthesis of benzimidazole derivatives at room temperature. Monatshefte für Chemie 2007;138:89-94
  • Lin SN, Yang LH. A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant. Tetrahedron Lett 2005;46:4315-19
  • Wang R, Lu XX, Yu XQ, et al. Acid-catalyzed solvent-free synthesis of 2-arylbenzimidazoles under microwave irradiation. J Mol Catal A 2007;266:198-201
  • Gogoi P, Dilip K. An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon-nitrogen bonds in water. Tetrahedron Lett 2006;47:79-82
  • Lee J, Doucette A, Wilson NS, et al. Solid phase synthesis of chiral 2-amino-benzimidazoles. Tetrahedron Lett 2001;42:2635-8
  • Huang WL, Scarborough RM. A new "traceless" Solid-phase synthesis strategy: synthesis of a benzimidazole library. Tetrahedron Lett 1999;40:2665-8
  • Tumelty D, Cao K, Holmes CP. Traceless solid-phase synthesis of substituted benzimidazoles via a base-cleavable linker. Org Lett 2001;3:83-6
  • Xue D, Long YQ. Metal-free TEMPO-promoted C(sp3)-H amination to afford multisubstituted benzimidazoles. J Org Chem 2014;79:4727-34
  • Lin JP, Zhang FH, Long YQ. Solvent/oxidant-switchable synthesis of multisubstituted quinazolines and benzimidazoles via metal-free selective oxidative annulation of arylamidines. Org Lett 2014;16:2822-5
  • Varala R, Nasreen A, Enugala R, et al. L-Proline catalyzed selective synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles. Tetrahedron Lett 2007;48:69-72
  • Hao LD, Zhao YF, Yu B, et al. Au catalyzed synthesis of benzimidazoles from 2-nitroanilines and CO2/H2. Green Chem 2014;16:3039-44
  • Yu B, Zhang HY, Zhao YF, et al. Cyclization of o-phenylenediamines by CO2 in the presence of H2 for the synthesis of benzimidazoles. Green Chem 2013;15:95-9

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.