New substituted benzimidazole derivatives: A patent review (2013-2014)

Expert Opinion on Therapeutic Patents

Volumn 25, Issue 5, 2015, Pages 595-612

  Wang, Miao ^a   Han, Xiaofeng ^a   Zhou, Zhiming ^a  

^a BEIJING INSTITUTE OF TECHNOLOGY   (China)

Author keywords

Anti Ebola virus activities; Anticancer activities; Antiviral activities; Benzimidazole derivatives; Ebola

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; ANTIVIRUS AGENT;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIHYPERTENSIVE ACTIVITY; ANTINEOPLASTIC ACTIVITY; DRUG DESIGN; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; NONHUMAN; PATENT; REVIEW; ANIMAL; CHEMISTRY; HEMORRHAGIC FEVER, EBOLA;

ANIMALS; ANTIVIRAL AGENTS; BENZIMIDAZOLES; DRUG DESIGN; HEMORRHAGIC FEVER, EBOLA; HUMANS; PATENTS AS TOPIC;

EID: 84928316597     PISSN: 13543776     EISSN: 17447674     Source Type: Journal    
DOI: 10.1517/13543776.2015.1015987     Document Type: Review

References (111)

1. Fei F, Zhou ZM. New substituted benzimidazole derivatives: A patent review (2010-2012). Expert Opin Ther Pat 2014;23:1157-79
2. Shah K, Chhabra S, Shrivastava SK, et al. Benzimidazole: A promising pharmacophore. Med Chem Res 2013;22:5077-104
3. Meng JP, Di RX, Zhou HC, et al. Development in benzimidazole drugs research. Chin J New Drugs 2009;18:1504-5
4. McKeown SR, Cowen RL, Williams KJ. Bioreductive drugs: From concept to clinic. Clin Oncol 2007;19:427-42
5. B?aszczak-S wiaitkiewicz 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
6. 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
7. 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
8. 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
9. Abou-Seri SM, Abouzid K, Abou Ei Ella DA. Molecular modeling study and synthesis of quinazolinonearylpiperazine derivatives as alpha1-adrenoreceptor antagonists. Eur J Med Chem 2011;46:647-58
10. 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
11. 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
12. 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
13. Goker H, Tebrizli E, Abbasoglu U. Benzimidazole-5(6)-carboxamides and evaluation of their antimicrobial activity. Farmaco 1996;51:53-8
14. Ozden S, Karatas H, Y?ld?z 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
15. Weidner-Wells MA, Ohemeng KA, Nguyen VN, et al. Amidino benzimidazole inhibitors of bacterial twocomponent systerms. Bioorg Med Chem Lett 2001;11:1545-8
16. Orhan Püsküllü M, Y?ld?z S, Goker H. Synthesis and antistaphylococcal activity of N-substituted-1H-benzimidazolesulphonamides. Arch Pharm (Weinheim) 2010;343:31-9
17. 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
18. 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
19. Pandey J, Tiwari VK, Verma SS, et al. Synthesis and antitubercular screening of imidazole derivatives. Eur J Med Chem 2009;44:3350-5
20. 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
21. 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
22. 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
23. Soria-Arteche O, Hernández-Campos A, Y-epez-Mulia L, et al. Synthesis and antiprotozoal activity of nitazoxanide-N-methylbenzimidazole hybrids. Bioorg Med Chem Lett 2013;22:6838-41
24. 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
25. Shen HC, Ding FX, Zhou CY, et al. Discovery of benzimidazole pyrrolidinyl amides as prolylcarboxypeptidase inhibitors. Bioorg Med Chem Lett 2011;21:1299-305
26. Kankala S, Kankala RK, Gundepaka P, et al. Regioselective synthesis of isoxazole-mercaptobenzimidazole hybrids and their in vivo analgesic and antiinflammatory activity studies. Bioorg Med Chem Lett 2013;23:1306-9
27. 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
28. 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
29. Herbert W, Gemma T, Alfred W, et al. Benzimidazoles for the treatment of cancer. EP2698367; 2014
30. Lelais G, Epple R, Michillys PY, et al. Compounds and compositions for modulating EGFR activity. WO184766; 2013
31. Chen Y, Chen Y. Novel therapeutic agents. WO113841; 2013
32. Rivero RA, Tedesco R, Luengo JI. Benzimidazole boronic acid derivatives as PI3 kinase inhibitors. US0157977; 2013
33. Staehle W, Schultz M, Schiemann K. N-(benzimimdazol-2-yl)-cyclopropane carboxamides as lysophosphatidic acid antagonists. WO020622; 2013
34. Zhou Y, Zhang LR, Zhou J, et al. Use of benzo five-membered nitrogen heterocyclic piperazine or piperidine derivatives. WO079155; 2014
35. Ge J, Ma JY, Xiang YG, et al. Benzimidazole derivatives, preparation method and medicinal use thereof. CN103709154; 2014
36. Hachtel S, Wohlfart P, Weston J, et al. Benzimidazole-carboxylic acid amide derivatives as APJ receptor modulators. WO044738; 2014
37. 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
38. Ojima I. Benzimidazoles and uses thereof. WO116823; 2013
39. Weibel DB, Eun YJ, Zhou MQ. Antimicrobial compositions and methods of use thereof. US0018079; 2013
40. Wang BX, Jiang YL, Zhou WL. 4Hpyrrolo[ 1, 2-a] benzimidazole derivative and synthesizing method and application thereof. CN102924460; 2013
41. Chen Y, Nichols D, Renslo A, et al. Compositions, methods of use, and methods of treatment. WO103760; 2013
42. Waters C, Sambanthamoorthy K, Neiditch M, et al. Benzimidazole inhibition of biofilm formation. US0345261; 2013
43. Zhang SM. Flavonoids or isoflavonoids compounds and uses thereof. WO121590; 2014
44. Chen Q, Lopez OD, Bender JA, et al. Hepatitis C virus inhibitors. US0121957; 2013
45. Scott RW, Vitale JP, Matthews KS, et al. Synthesis of antiviral compound. US20130324740; 2013
46. Qiu YL, Wang C, Peng XW, et al. Novel benzimidazole derivatives. WO052369; 2013
47. Feng S, Gao L, Hong D, et al. Novel indazoles for the treatment and prophylaxis of respiratory syncytial virus infection. WO009302; 2014
48. Gomtsian A, Dekhtyar T, Frank KE, et al. Cyanoguanidines and their use as antiviral agents. WO005129; 2014
49. Cockerill S, Pilkington C, Lumley J, et al. Pharmaceutical compounds. WO068769; 2013
50. De Grado WF, Wang JZ, Wang J, et al. Inhibitors targeting drus-resistant influenza A. WO086131; 2013
51. Luo XJ. Method for preparing benzimidazole heterocyclic compound. CN103087044; 2013
52. Gurjar MK, Maikap GS, Tripathy NK, et al. Pyridone derivatives as acid secretion inhibitors and process for preparation thereof. WO080422; 2014
53. Yang YJ, Li ZL. Synthesis method of Lansoprazole and Lansoprazole synthesized thereby. CN103288799; 2013
54. Eckhardt M, Langkopf E, Wagner H. Indanyloxydihydrobenzofuranylacetic acids. US0148462; 2014
55. Apgar JM, Biftu T, Chen P, et al. Novel benzimidazole tetrahydrofuran derivatives. WO031441; 2014
56. Apgar JM, Biftu T, Chen P, et al. Novel benzimidazole derivatives. WO031445; 2014
57. Devita RJ, Yu Y, Liu J, et al. Compounds as DGAT-1 inhibitors. WO130370; 2013
58. Kasal S, Igawa H, Takahashi M, et al. Benzimidazole derivatives as MCH receptor antagonists. WO105676; 2013
59. Kamenecka TM, Griffin PR. N-biphenylmethylbenzimidazole modulators of PPARG. WO078240; 2013
60. Kamenecka TM, Griffin PR. N-biphenylmethylbenzimidazole modulators of PPARG. WO078233; 2013
61. Liu J, Balkovec JM, Krikorian AD, et al. Imidazole derivatives. WO074387; 2013
62. Wang HY, Zhu WL, Cai HY, et al. Application of 2,4,6-triisopropylbenzene compounds in preparation of medicines for treating diabetes. CN103040815; 2013
63. Hua EB, Jia SL, Wang QY. Benzimidazole derivative, and preparation method and application thereof. CN102942562; 2013
64. Gharat LA, Muthukaman N, Deshmukh S, et al. Tricyclic compounds as mPGES-1 inhibitors. WO153535; 2013
65. Hadida-Ruah SS, Grootenhuis PDJ, Miller MT, et al. Benzoxazines as modulators of ion channels. WO067248; 2013
66. Bagal SK, Brown AD, Kemp MI, et al. Benzimidazole and imidazopyridine derivatives as sodium channel modulators. WO114250; 2013
67. Pae AN, Min SJ, Roh EJ, et al. Benzimidazole derivatives as mitochondrial function modulators. US0114067; 2014
68. Ceccarelli SM, Jagasia R, Jakobroetne R, et al. Benzimidazoles as CNS active agents. WO053409; 2014
69. Geneste H, Ochse M, Drescher K, et al. Novel inhibitor compounds of phosphodiesterase type 10A. US0116233; 2013
70. Beshore DC, Culberson C, Johnson AW, et al. Azetidine benzimidazoles as PDE10 inhibitors. WO078214; 2014
71. Kuduk SD, Mccomas CC, Reger TS. Cyclobutyl benzimidazoles as PDE10 inhibitor. WO078216; 2014
72. Luo HR, Hong XC, Deng ZX, et al. Benzimidazole and derivative thereof, and medicinal composition and application thereof. CN103121969; 2013
73. Duncan KM, Chesworth R, Boriack-sjodin PA, et al. PRMT5 inhibitors containing a dihydroor tetrahydroisoquinoline and uses thereof. WO100730; 2014
74. Czardybon W, Brz-zka K, Galezowski M, et al. Novel benzimidazole derivatives as kinase inhibitors. WO096388; 2014
75. Rzymski T, Zarebski A, Dreas A, et al. Substituted tricyclic benzimidazoles as kinase inhibitors. WO072435; 2014
76. Dickman DA, Kumar DV, O'bryan C, et al. Factor VIIA inhibitor. US8729117; 2014
77. Brameld KA, Owens TA. Benzimidazole derivatives as ITK inhibitors. WO036016; 2014
78. Chaudhari SS, Thomas A, Adik BG, et al. Novel urea derivatives as TEC kinase inhibitors and uses thereof. WO024427; 2013
79. Boss C, Brotschi C, Gude M, et al. Benzimidazole-proline derivatives. WO182972; 2013
80. Brooks C, Cheung M, Eidam HS, et al. TRPV4 antagonists. WO012500; 2013
81. 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. Their study suggested that benzimidazoles may have the potential to be the first effective therapy against Ebola virus.
82. 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
83. 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
84. 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
85. 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
86. 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
87. 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
88. 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
89. Wang P, Zheng GJ, Wang YP, et al. Highly practical and cost-efficient synthesis of telmisartan: An antihypertensive drug. Tetrahedron 2012;68:2509-12
90. Husain A, Azim MS, Mitra M, et al. A review on Candesartan: Pharmacological and pharmaceutical profile. J Pharm Sci 2011;01:12-17
91. Wang P, Zheng GJ, Wang YP, et al. A novel and practica lsynthesis of substituted 2-ethoxybenzimidazole: Candesartan cilexetil. Tetrahedron 2010;66:5402-6
92. 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
93. Hernández-Luis F, Hernández-Campos A, Y-epez-Mulia L, et al. Synthesis and hydrolytic stability studies of albendazole carrier prodrugs. Bioorg Med Chem Lett 2001;11:1359-62
94. 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
95. 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
96. 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
97. 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
98. Zhang ZH, Yin L, Wang YM. An expeditious synthesis of benzimidazole derivatives catalyzed by Lewis acids. Catal Commun 2007;8:1126-31
99. 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
100. 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
101. 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. Their study is the new green process of the synthesis of benzimidazole compounds.
102. 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
103. Gogoi P, Dilip K. An efficient and onepot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon-nitrogen bonds in water. Tetrahedron Lett 2006;47:79-82
104. Lee J, Doucette A, Wilson NS, et al. Solid phase synthesis of chiral 2-amino-benzimidazoles. Tetrahedron Lett 2001;42:2635-8
105. Huang WL, Scarborough RM. A new "traceless" Solid-phase synthesis strategy: SYNTHESIS OF A BENZIMidazole library. Tetrahedron Lett 1999;40:2665-8
106. Tumelty D, Cao K, Holmes CP. Traceless solid-phase synthesis of substituted benzimidazoles via a basecleavable linker. Org Lett 2001;3:83-6
107. Xue D, Long YQ. Metal-free TEMPOpromoted C(sp3)-H amination to afford multisubstituted benzimidazoles. J Org Chem 2014;79:4727-34
108. 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
109. 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
110. 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
111. 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