Coumarin derivatives: an updated patent review (2015-2016)

References

• Bourgaud F, Hehn A, Larbat R, et al. Biosynthesis of coumarins in plants: a major pathway still to be unravelled for cytochrome P450 enzymes. Phytochem Rev. 2006;5(2–3):293–308.
   Google Scholar
• Lake BG. Coumarin metabolism, toxicity and carcinogenicity: relevance for human risk assessment. Food Chem Toxicol. 1999;37(4):423–453.
   PubMed Web of Science ®Google Scholar
• Marshall ME, Mohler JL, Edmonds K, et al. An updated review of the clinical development of coumarin (1, 2-benzopyrone) and 7-hydroxycoumarin. J Cancer Res Clin Oncol. 1994;120, (suppl 1):S39–S42.
   PubMed Web of Science ®Google Scholar
• Murray RDH. Naturally occuring plant coumarins. In: Kinghorn AD, Falk H, Kobayashi J, Editors. Progress in the chemistry of organic natural products. New York (NY): Springer; 1997. p. 2–105.
   Google Scholar
• Bairagi SH, Salaskar PP, Loke SD, et al. Medicinal significance of coumarins. Int J Pharm Res. 2012;4(2):16–19.
   Google Scholar
• Batra N, Batra S, Pareek A, et al. Diverse pharmacological activities of 3-substituted coumarins: a review. Int Res J Pharm. 2012;3(7):24–29.
   Google Scholar
• Wang H, Lu X, Yao H, et al. Research progress on application of coumarin and its derivatives. Chem Ind Times. 2009;23(8):40–43.
   Google Scholar
• Lacy A, O’Kennedy R. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. Curr Pharm Des. 2004;10:3797–3811.
   PubMed Web of Science ®Google Scholar
• Borges F, Roleira F, Milhazes N, et al. Simple coumarins and analogues in medicinal chemistry: occurrence, synthesis and biological activity. Curr Med Chem. 2005;12(8):887–916.
   PubMed Web of Science ®Google Scholar
• Kontogiorgis C, Detsi A, Hadjipavlou-Litina D. Coumarin-based drugs: a patent review (2008 – present). Expert Opin Ther Pat. 2012;22(4):437–454.
   PubMed Web of Science ®Google Scholar
• Katsori A-M, Hadjipavlou-Litina D. Coumarin derivatives: an updated patent review (2012-2014). Expert Opin Ther Pat. 2014;24(12):1323–1347.
   PubMed Web of Science ®Google Scholar
• Wang G, Liu G, Ling F, et al. Coumarin compound containing imidazolium-based functional groups and preparation method and application thereof. CN 105732601. 2016.
   Google Scholar
• Zhou C, Rao AS, Peng S, et al. Azolol compound based on coumarin useful in treatment of bacterial and fungal infection and its preparation. CN 105693705. 2016.
   Google Scholar
• Ombrato R, Garofalo B, Mangano G, et al. Aziende chimiche riunite, angelini francesco A.C.R.A.F. S.P.A. Preparation of heterocyclic compounds as antibacterial agents. WO 2016096631. 2016.
   Google Scholar
• Zhu H, Wang S, Yin Y, et al. Piperazine ring-containing coumarin derivatives and preparation method and application thereof in antibacterial drugs. CN 105218501. 2016.
   Google Scholar
• Zhou C, Kumar KV, Peng S. Coumarin azole compounds and preparation method and application thereof. CN 104910176. 2015.
   Google Scholar
• Wang G, Peng Z, Liu W, et al. Preparation of coumarin-thiazole-indolone type compound used for antibacterial drugs. CN 104829608. 2015.
   Google Scholar
• Wang G, Peng Z, He D, et al. Preparation of (E)-N’-arylmethylene-4-(coumarin-3-yl)thiazole-2-hydrazide compounds as antimicrobial agents. CN 104817552. 2015.
   Google Scholar
• Zhu H, Sun S, Li H, et al. Bacterial quorum-sensing inhibitor and antibacterial application thereof. CN 106117232. 2016.
   Google Scholar
• Zhu H, Qu X, Zeng H, et al. Application of coumarin compounds in manufacture of medicines for anti-HIV incubation treatment. CN 105708836. 2016.
   Google Scholar
• Xian L, Hanxian Z, Pengfei W, et al. Reactivation of latent HIV-1 in latently infected cells by coumarin compounds: hymecromone and scoparone. Curr HIV Res. 2016;14:1–7.
   Web of Science ®Google Scholar
• Trkovnik M, Cacic M, Rizvani J, Preparation of a coumarin derivative as an antiviral agent, pharmaceutical composition thereof and its use. WO 2016156888. 2016.
   Google Scholar
• Yuan Y, Xu J; inventors, et al. Compositions and methods for treating herpesvirus infection. WO 2015081199. 2015.
   Google Scholar
• Hao S, Wang D, Wei Y, et al. N-Acyl-N-m-fluorobenzyl-8-amino coumarin compounds and their preparation and herbicidal use. CN 104592183. 2015.
   Google Scholar
• Qin B, Pan Y, Li X, et al., Preparation of coumarins as nematicides. CN 104829601. 2015.
   Google Scholar
• Pan L, Li XZ, Sun DA, et al. Design and synthesis of novel coumarin analogs and their nematicidal activity against five phytonematodes. Chin Chem Lett. 2016;27(3):375–379.
   Web of Science ®Google Scholar
• Jackson A, Wynn DG, Newington I, et al. Preparation of 18F-labeled coumarin derivatives useful as in vivo imaging agent for MAO-B. WO 2016097339. 2016.
   Google Scholar
• De Monte C, Ascenzio M, Guglielmi P, et al. Opening new scenarios for human MAO inhibitors. Cent Nerv Syst Agents Med Chem. 2016;16(2):98–104.
   PubMedGoogle Scholar
• Chen D, Yin X, Shi X, et al. Application of coumarin compounds in preparation of anti-hepatitis B virus medicine. CN 105520937. 2016.
   Google Scholar
• Fu H, Wang K, Zhang B, et al. Process for preparation of coumarin derivative for treating cerebral ischemia. CN 105524034. 2016.
   Google Scholar
• Dong C, Wang G, Huang J, et al. Triazolyl-tacrine-coumarin derivatives as acetylcholinesterase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of Alzheimer’s disease. CN 105503840. 2016.
   Google Scholar
• Ruan B, Cheng H, Li H, et al. Preparation of stilbene coumarin derivatives as human monoamine oxidase inhibitors. CN 104892556. 2015.
   Google Scholar
• Schwiebert Ε, Streiff J, Dixon J, et al., Coumarin derivatives and methods of use in treating cystic fibrosis, chronic obstructive pulmonary disease, and misfolded protein disorders. WO 2014152213. 2014.
   Google Scholar
• Wang G, Peng Z, Li J, et al. Preparation of 1,2,4-triazine-coumarin compounds useful as a-glucosidase inhibitor for the treatment of diabetes. CN 105601624 A. 2016.
   Google Scholar
• Wang G, Wang J, He D, et al. Synthesis, in vitro evaluation and molecular docking studies of novel coumarin-isatin derivatives as α-glucosidase inhibitors. Chem Biol Drug Des. 2017;89(3):456–463.
   PubMed Web of Science ®Google Scholar
• Huo L, Wei J, Chen R, et al. Application of 3-phenylcoumarin robustic acid as antioxidant for treating diabetes. CN 105287511 A. 2016.
   Google Scholar
• Wang G, Peng Z, He D, et al. Coumarin-isatin type compound useful in treatment of diabetes mellitus and its preparation. CN 105237521 A. 2016.
   Google Scholar
• Rane RA, Karunanidhi S, Jain K, et al. A recent perspective on discovery and development of diverse therapeutic agents inspired from isatin alkaloids. Curr Top Med Chem (Sharjah, United Arab Emirates). 2016;16:1262–1289.
   PubMed Web of Science ®Google Scholar
• Rahim F, Malik F, Ullah H, et al. Isatin based Schiff bases as inhibitors of α-glucosidase: synthesis, characterization, in vitro evaluation and molecular docking studies. Bioorg Chem. 2015;60:42–48.
   PubMed Web of Science ®Google Scholar
• Qi L-W, Liu EH, Chu C, et al. Anti-diabetic agents from natural products–an update from 2004 to 2009. Curr Top Med Chem. 2010;10:434–457, and references cited there.
   PubMed Web of Science ®Google Scholar
• Khan KM, Rahim F, Wadood A, et al. Synthesis and molecular docking studies of potent α-glucosidase inhibitors based on biscoumarin skeleton. Eur J Med Chem. 2014;81:245–252.
   PubMed Web of Science ®Google Scholar
• Raju BC, Tiwari AK, Kumar JA, et al. alpha-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives. Biorg Med Chem. 2010;18:358–365.
   PubMed Web of Science ®Google Scholar
• Shen Q, Shao J, Peng Q, et al. Hydroxycoumarin derivatives: novel and potent α-glucosidase inhibitors. J Med Chem. 2010;53:8252–8259.
   PubMed Web of Science ®Google Scholar
• Wang S, Yan J, Wang X, et al. Synthesis and evaluation of the α-glucosidase inhibitory activity of 3-[4-(phenylsulfonamido)benzoyl]-2H-1-benzopyran-2-one derivatives. Eur J Med Chem. 2010;4:1250–1255.
   Web of Science ®Google Scholar
• Menteşe E, Karaali N, Akyüz G, et al. Synthesis and evaluation of α-glucosidase and pancreatic lipase inhibition by quinazolinone-coumarin hybrids. Chem Heterocyc Compound. 2016;52(12):1017–1024.
   Web of Science ®Google Scholar
• Yu P, Pan G, Sun H, et al. Preparation of coumarin substituted flavonoid derivatives for treating diabetes. CN 104945455 A. 2015.
   Google Scholar
• Zhang D, Du G, Wang Y, et al. Preparation of coumarin glycoside compounds for treating diabetic angiopathy. CN 104910119 A. 2015.
   Google Scholar
• Fu H, Wang K, Zhang H, et al. Coumarin derivative for treatment of pruritus and its preparation. CN 105566269 A. 2016.
   Google Scholar
• Uchiki M, Okada T, Sawada K, et al., Kokai Tokyo Koho Nippon Zoki Pharmaceutical Co Ltd assignee, Pharmaceuticals containing coumarin derivatives for treatment of arthropathy. JP 2015193610 A. 2015.
   Google Scholar
• Li F, Hu J, Wang J, A coumarin derivative as antioxidant and its preparation. CN 103601710 A (2014) and CN 103601711 A. 2014.
   Google Scholar
• Seo S-Y, Ashraf Z, Rafiq M, et al. Coumarin derivative as tyrosinase inhibitor and method for the preparation thereof. KR 2016085943 A. 2016.
   Google Scholar
• Carrico-Moniz D Coumarin derivatives for cancer therapy. U.S. 9388155 B1. 2016.
   Google Scholar
• Wang K, Li D, inventors; Faming Zhuanli Shenqing. Coumarin dimer (7-hydroxy-6,8-dimethoxy-3-((6-methoxy-2-oxo-2H-chromen-7-yl)oxy)-2H-chromen-2-one) and its preparation method and application. CN 105712963 A. 2016.
   Google Scholar
• Zhao J, Zhaon H, Blagg BSJ. Triazole modified coumarin and biphenyl amide-based HSP90 inhibitors. WO 2015192099 A1. 2015.
   Google Scholar
• Chen Y, Chem X, Liu M, et al. Preparation of coumarin-nucleus furazan derivatives with antitumor activity. CN 105153142 A. 2015.
   Google Scholar
• Zhu H, Wu X, Yin Y, et al., Preparation of coumarin-pyrazole fused compounds as anti-tumor agents. CN 105061441 A. 2015.
   Google Scholar
• Zhu H, Wu X, Yin Y et al. Coumarin-pyrazole fused compounds containing acetamino nitrogen heterocycles, their preparation method and their application in tumor cell inhibition. CN 105061440 A. 2015.
   Google Scholar
• Zhu H, Wu X, Yin Y, et al., Coumarin-pyrazole-sulfonylpiperazines in tumor cell inhibition and their preparation, pharmaceutical compositions and use in the treatment of cancer. CN 105061442 A. 2015.
   Google Scholar
• Zhu H, Wu X, Yin Y, et al., Preparation of coumarin-pyrazol compound containing carbonyl or oxime for use in medicine for inhibiting tumor cell. CN 104961743 A. 2015.
   Google Scholar
• Zhu H, Wu X, Yin Y, et al. Preparation of phenylsulfonyl or alkylsulfonyl-containing coumarin-pyrazole derivatives and their application in tumor suppression. CN 104926821 A. 2015.
   Google Scholar
• Wang D, Zhong Z, Xing J et al., Preparation of coumarins compound with antioxidation activity for use in neuroprotectant, antitumor, anticoagulant, antiradiation and antiinflammatory drugs. CN 104974123 A. 2015.
   Google Scholar
• Blagg BSJ, Zhao H, inventors; The University of Kansas. Urea- and ether-substituted coumarin derivative as HSP90 inhibitors and their preparation. WO 2015070238 A2. 2015.
   Google Scholar
• Taipale M, Jarosz DF, Lindquist S. HSP90 at the hub of protein homeostasis: emerging mechanistic insights. Nat Rev Mol Cell Biol. 2010;11:515–528.
   PubMed Web of Science ®Google Scholar
• Hanahan D, Weinberg RA. Hallmarks of cancer: the next generation. Cell. 2011;144(5):646–674.
   PubMed Web of Science ®Google Scholar
• Draoui N, Feron O, Riant O, et al. Preparation of 3-carboxy-substituted coumarin derivatives with a potential utility for the treatment of cancer. WO 2014195507 A1. 2014.
   Google Scholar
• Schwiebert E, Streiff J, Dixon J, et al. Preparation of coumarin thiazolyl derivatives and methods of use in treating hyperproliferative diseases. WO 2014152278 A2. 2014.
   Google Scholar
• Schwiebert E, Streiff J, Dixon J, et al. Coumarin derivatives and methods of use in treating hyperproliferative diseases. US 20160038475 A1. 2016.
   Google Scholar
• Zhang G, Liu K, Zhang Y, et al. Theanine-coumarin carboxylic acid derivatives as NF-κB inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases. WO 2014048313 A1. 2014.
   Google Scholar
• Zhang G, Kun L, Zhang Y, et al., Theanine-coumarin carboxylic acid derivatives as EZH2 and NF-κB inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases. CN 103690531 A. 2014.
   Google Scholar
• Zhang G, Liu K, Zhang Y, et al. Theanine-coumarin carboxylic acid derivatives as EZH2 and NF-κB inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases. CN 103690530 A. 2014.
   Google Scholar
• Zhang G, Kun L, Zhang Y, et al. Application of ethyl 6-bromocoumarin-3-carboxylyl L-theanine and the like in preparation of product used for preventing and treating disease such as cancers. CN 103690528 A. 2014.
   Google Scholar
• Wang Y, Lu P, Yuan X et al. Coumarin derivatives as NEDD8-activating enzyme inhibitors and their preparation, pharmaceutical compositions and use in the treatment of cancer. CN 106008475 A. 2016.
   Google Scholar
• Yu B, Zhang J, Fan N, et al. Preparation of 7-amino-4-methylcoumarin-β-D-glucopyranoside as antitumor agent. CN 105968153 A. 2016.
   Google Scholar
• Oda K, Nishisono N, Yamaguchi Y, et al. Aromatase inhibitor containing coumarin derivatives, and medicament comprising same. JP2016138053A. 2016.
   Google Scholar
• Xiang H, Mo X, Luo G, et al. 3-Aryl-4-aromatic amine-coumarin derivatives as antitumor agents and their preparation, pharmaceutical compositions and use in the treatment of mammary cancer. CN105801544 A. 2016.
   Google Scholar
• Xiang H, Mo X, Luo G, et al. Preparation of 4-aromatic amino-coumarin derivative and their medicinal use as antitumor agent. CN105801543 A. 2016.
   Google Scholar
• Zhu H, Wang Z, Liu Y, et al., Design and Synthesis of coumarin piperazine compounds as antitumor agents. CN 105777690 A. 2016.
   Google Scholar
• Smyth T, Ramachandran VN, Smyth WF. A study of the antimicrobial activity of selected naturally occurring and synthetic coumarins. Int J Antimicrob Agents. 2009;33(5):421–426.
   PubMed Web of Science ®Google Scholar
• Jain P, Joshi H. Coumarin: chemical and pharmacological profile. J App Pharm Sci. 2012;2(6):236–240.
   Google Scholar
• Burke AS, FitzGerald GA. Analgesic-antipyretic and antiinflammatory agents; pharmacotherapy of Gout. In: Brunton L, Lazo J, Parker K, editors. Goodman & Gilman’s the pharmacological basis of therapeutics. 11 ed. New York: McGraw-Hill Education; 2005. p. 1211–1218.
   Google Scholar
• Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE, et al. Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities. Curr Pharm Des. 2004;10(30):3813–3833.
   PubMed Web of Science ®Google Scholar