Generic placeholder image

Mini-Reviews in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

Mini-Review Article

Inhibitory Activities of Pyrazolo-Oxazine Heterocyclic Derivatives

Author(s): Thoraya A. Farghaly* and Kamal M. Dawood

Volume 22, Issue 9, 2022

Published on: 18 January, 2022

Page: [1256 - 1267] Pages: 12

DOI: 10.2174/1389557522666211229114446

Price: $65

conference banner
Abstract

Despite several reports and reviews addressing the biological significance of pyrazoles and oxazines, no comprehensive work on the pyrazolo oxazine fused ring system has been published so far. We report all biological evaluations on pyrazolo-oxazine derivatives in this mini-review to provide an avenue for medicinal and pharmacological researchers to conduct further in-depth exploration.

Keywords: Pyrazolo-oxazine, antimicrobial, anticancer, analgesic activity, anti-hepatitis (HCV), inhibitory activity.

Graphical Abstract

[1]
Reddy, E.K.; Battula, S.; Anwar, S.; Sajith, A.M. Drug re-purposing approach and potential therapeutic strategies to treat COVID-19. Mini Rev. Med. Chem., 2021, 21(6), 704-723.
[http://dx.doi.org/10.2174/1389557520666201113105940] [PMID: 33185159]
[2]
Mahmoud, H.K.; Farghaly, T.A.; Abdulwahab, H.G.; Al-Qurashi, N.T.; Shaaban, M.R. Novel 2-indolinone thiazole hybrids as sunitinib analogues: Design, synthesis, and potent VEGFR-2 inhibition with potential anti-renal cancer activity. Eur. J. Med. Chem., 2020, 208, 112752.
[http://dx.doi.org/10.1016/j.ejmech.2020.112752] [PMID: 32947227]
[3]
Al-Hussain, S.A.; Farghaly, T.A.; Zaki, M.E.A.; Abdulwahab, H.G.; Al-Qurashi, N.T.; Muhammad, Z.A. Discovery of novel indolyl-1,2,4-triazole hybrids as potent vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitors with potential anti-renal cancer activity. Bioorg. Chem., 2020, 105, 104330.
[http://dx.doi.org/10.1016/j.bioorg.2020.104330] [PMID: 33038552]
[4]
Hosseinzadeh, Z.; Ramazani, A.; Razzaghi-Asl, N. Anti-cancer nitrogen-containing heterocyclic compounds. Curr. Org. Chem., 2018, 22, 2256-2279.
[http://dx.doi.org/10.2174/1385272822666181008142138]
[5]
Farghaly, T.A.; Abdallah, M.A.; Mahmoud, H.K. The utility of hydrazonoyl halides in the synthesis of bioactive heterocyclic compounds. Curr. Org. Synth., 2017, 14, 430-461.
[http://dx.doi.org/10.2174/1570179413666160624105624]
[6]
Sun, Z.G.; Zhao, L.H.; Li, Z.N.; Zhu, H.L. Development and challenges of the discovery of HER2 inhibitors. Mini Rev. Med. Chem., 2020, 20(20), 2123-2134.
[http://dx.doi.org/10.2174/1389557520666200729162118] [PMID: 32727326]
[7]
Singh, G.; Chandra, P.; Sachan, N. Chemistry and pharmacological activities of pyrazole and pyrazole derivatives: A review. Int. J. Pharm. Sci. Rev. Res., 2020, 65, 201-214.
[http://dx.doi.org/10.47583/ijpsrr.2020.v65i01.030]
[8]
Brullo, C.; Rapetti, F.; Bruno, O. Pyrazolyl-ureas as interesting scaffold in medicinal chemistry. Molecules, 2020, 25(15), 3457.
[http://dx.doi.org/10.3390/molecules25153457] [PMID: 32751358]
[9]
Dawood, K.M. Benzofuran derivatives: A patent review. Expert Opin. Ther. Pat., 2013, 23(9), 1133-1156.
[http://dx.doi.org/10.1517/13543776.2013.801455] [PMID: 23683135]
[10]
Dawood, K.M. An update on benzofuran inhibitors: A patent review. Expert Opin. Ther. Pat., 2019, 29(11), 841-870.
[http://dx.doi.org/10.1080/13543776.2019.1673727] [PMID: 31560232]
[11]
Dawood, K.M.; Abbas, A.A. Inhibitory activities of indolizine derivatives: A patent review. Expert Opin. Ther. Pat., 2020, 30(9), 695-714.
[http://dx.doi.org/10.1080/13543776.2020.1798402] [PMID: 32684068]
[12]
Patel, B.; Zunk, M.; Grant, G.; Rudrawar, S. Design, synthesis and bioactivity evaluation of novel pyrazole linked phenylthiazole derivatives in context of antibacterial activity. Bioorg. Med. Chem. Lett., 2021, 39, 127853.
[http://dx.doi.org/10.1016/j.bmcl.2021.127853] [PMID: 33609657]
[13]
Liu, H.; Chu, Z-W.; Xia, D-G.; Cao, H-Q.; Lv, X-H. Discovery of novel multi-substituted benzo-indole pyrazole Schiff base derivatives with antibacterial activity targeting DNA gyrase. Bioorg. Chem., 2020, 99, 103807.
[http://dx.doi.org/10.1016/j.bioorg.2020.103807] [PMID: 32272364]
[14]
Verma, V.; Singh, K.; Kumar, D.; Narasimhan, D. QSAR studies of antimicrobial activity of 1,3-disubstituted-1H-naphtho[1,2-e][1,3]oxazines using topological descriptors. Arab. J. Chem., 2017, 10, S747-S756.
[http://dx.doi.org/10.1016/j.arabjc.2012.11.021]
[15]
Manjula, M.K.; Rai, K.M.L.; Gaonkar, S.L.; Raveesha, K.A.; Satish, S. Synthesis of new series of 5,6-dihydro-4H-1,2-oxazines via hetero Diels-Alder reaction and evaluation of antimicrobial activity. Eur. J. Med. Chem., 2009, 44(1), 280-288.
[http://dx.doi.org/10.1016/j.ejmech.2008.02.027] [PMID: 18420309]
[16]
Muhammad, Z.A.; Alshehrei, F.; Zayed, M.E.M.; Farghaly, T.A.; Abdallah, M.A. Synthesis of novel bis-pyrazole derivatives as antimicrobial agents. Mini Rev. Med. Chem., 2019, 19(15), 1276-1290.
[http://dx.doi.org/10.2174/1389557519666190313095545] [PMID: 30864524]
[17]
Althagafi, I.; El-Metwaly, N.M.; Elghalban, M.G.; Farghaly, T.A.; Khedr, A.M. Synthesis of pyrazolone derivatives and their nanometer Ag(I) complexes and physicochemical, DNA binding, antitumor and theoretical implementations. Bioinorg. Chem. Appl., 2018, 2018, 2727619.
[http://dx.doi.org/10.1155/2018/2727619] [PMID: 29861710]
[18]
Somu, C.; Mohan, C.D.; Ambekar, S. Dukanya; Rangappa, S.; Baburajeev, C.P.; Sukhorukov, A.; Mishra, S.; Shanmugam, M.K.; Chinnathambi, A.; Awad Alahmadi, T.; Alharbi, S.A.; Rangappa, K.S. Identification of a novel 1,2 oxazine that can induce apoptosis by targeting NF-κB in hepatocellular carcinoma cells. Biotechnol. Rep. (Amst.), 2020, 25, e00438.
[http://dx.doi.org/10.1016/j.btre.2020.e00438] [PMID: 32140443]
[19]
Carramiñana, V.; Ochoa de Retana, A.M.; de Los Santos, J.M.; Palacios, F. First synthesis of merged hybrids phosphorylated azirino[2,1-b]benzo[e][1,3]oxazine derivatives as anticancer agents. Eur. J. Med. Chem., 2020, 185, 111771.
[http://dx.doi.org/10.1016/j.ejmech.2019.111771] [PMID: 31671309]
[20]
Riyadh, S.M.; Farghaly, T.A.; Abdallah, M.A.; Abdalla, M.M.; Abd El-Aziz, M.R. New pyrazoles incorporating pyrazolylpyrazole moiety: Synthesis, anti-HCV and antitumor activity. Eur. J. Med. Chem., 2010, 45(3), 1042-1050.
[http://dx.doi.org/10.1016/j.ejmech.2009.11.050] [PMID: 20022411]
[21]
Hwang, J.Y.; Kim, H-Y.; Park, D-S.; Choi, J.; Baek, S.M.; Kim, K.; Kim, S.; Seong, S.; Choi, I.; Lee, H-G.; Windisch, M.P.; Lee, J. Identification of a series of 1,3,4-trisubstituted pyrazoles as novel hepatitis C virus entry inhibitors. Bioorg. Med. Chem. Lett., 2013, 23(23), 6467-6473.
[http://dx.doi.org/10.1016/j.bmcl.2013.09.039] [PMID: 24125883]
[22]
Zhou, D.; Harrison, B.L.; Shah, U.; Andree, T.H.; Hornby, G.A.; Scerni, R.; Schechter, L.E.; Smith, D.L.; Sullivan, K.M.; Mewshaw, R.E. Studies toward the discovery of the next generation of antidepressants. Part 5: 3,4-Dihydro-2H-benzo[1,4]oxazine derivatives with dual 5-HT1A receptor and serotonin transporter affinity. Bioorg. Med. Chem. Lett., 2006, 16(5), 1338-1341.
[http://dx.doi.org/10.1016/j.bmcl.2005.11.054] [PMID: 16332439]
[23]
Yang, G.; Zheng, H.; Shao, W.; Liu, L.; Wu, Z. Study of the in vivo antiviral activity against TMV treated with novel 1-(t-butyl)-5-amino-4-pyrazole derivatives containing a 1,3,4-oxadiazole sulfide moiety. Pestic. Biochem. Physiol., 2021, 171, 104740.
[http://dx.doi.org/10.1016/j.pestbp.2020.104740] [PMID: 33357562]
[24]
Raić-Malić, S.; Tomasković, L.; Mrvoš-Sermek, D.; Prugovečki, B.; Cetina, M.; Grdiša, M.; Pavelić, K.; Mannschreck, A.; Balzarini, J.; De Clercq, E.; Mintas, M. Spirobipyridopyrans, spirobinaphthopyrans, indolinospiropyridopyrans, indolinospironaphthopyrans and indolinospironaphtho-1,4-oxazines: Synthesis, study of X-ray crystal structure, antitumoral and antiviral evaluation. Bioorg. Med. Chem., 2004, 12(5), 1037-1045.
[http://dx.doi.org/10.1016/j.bmc.2003.12.010] [PMID: 14980617]
[25]
Khan, M.F.; Alam, M.M.; Verma, G.; Akhtar, W.; Akhter, M.; Shaquiquzzaman, M. The therapeutic voyage of pyrazole and its analogs: A review. Eur. J. Med. Chem., 2016, 120, 170-201.
[http://dx.doi.org/10.1016/j.ejmech.2016.04.077] [PMID: 27191614]
[26]
Abdel-Aziz, M. Abuo-Rahma, Gel-D.; Hassan, A.A. Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities. Eur. J. Med. Chem., 2009, 44(9), 3480-3487.
[http://dx.doi.org/10.1016/j.ejmech.2009.01.032] [PMID: 19268406]
[27]
Beyhan, N.; Kocyigit-Kaymakcioglu, B.; Gümrü, S.; Aricioglu, F. Synthesis and anticonvulsant activity of some 2-pyrazolines derived from chalcones. Arab. J. Chem., 2017, 10, S2073-S2081.
[http://dx.doi.org/10.1016/j.arabjc.2013.07.037]
[28]
Viegas-Junior, C.; Danuello, A.; da Silva Bolzani, V.; Barreiro, E.J.; Fraga, C.A.M. Molecular hybridization: A useful tool in the design of new drug prototypes. Curr. Med. Chem., 2007, 14(17), 1829-1852.
[http://dx.doi.org/10.2174/092986707781058805] [PMID: 17627520]
[29]
El-Tammany, E.H.; Hamed, A.A.; Sowellim, S.Z.A.; Radwan, A.S. Azoniaallene salts as versatile building blocks in the synthesis of antibacterial and antifungal heterocyclic compounds. Nat. Sci., 2012, 4, 1013-1021.
[http://dx.doi.org/10.4236/ns.2012.412130]
[30]
Zou, R.M.; Beylin, V.G.; Groziak, M.P.; Wotring, L.L.; Townsend, L.B. Synthetic approaches to the guanosine and xanthosine analogues 5-amino-3-beta-D-ribofuranosylpyrazolo[3,4-e][1,3]oxazin-7-one and 3-beta-D-ribofuranosylpyrazolo[3,4-e][1,3]oxazine-5,7-dione and studies of their antitumor potential. J. Med. Chem., 1991, 34(7), 1951-1959.
[http://dx.doi.org/10.1021/jm00111a005] [PMID: 2066967]
[31]
Daidone, G.; Bajardi, M.L.; Roccaro, A.; Raffa, D.; Caruso, A.; Cutuli, V.; Di Pietro, E. Researches on antiinflammatory agents. Studies on some 1-methyl- or 1-phenyl-6-(2-substitutedphenyl)- pyrazolo[3,4-d]-1,3-oxazin-4(1H)-ones. Farmaco, 1991, 46(7-8), 945-957.
[PMID: 1793477]
[32]
Erian, A.W.; El-Gohary, S.; Manhi, F.M.; Ali, F.A. A novel synthesis of fused pyrazole systems as antimicrobial agents. Pharmazie, 1998, 53(11), 748-751.
[PMID: 9853356]
[33]
Radhika, S.; Gary, S.L.; Maktoob, A.; Alfred, J.W.; Gary, E.M.; Edward, L.E. Two-dimensional NMR studies of marine natural products. IV. Isolation of the cembranoid diterpene jeunicin from the mollusc planaxis sulcatus: Assignment of the proton and carbon NMR spectra by two-dimensional techniques. Heterocycl. Chem., 1986, 23, 529-535.
[34]
Jarvest, R.L.; Pinto, I.L.; Ashman, S.M.; Dabrowski, C.E.; Fernandez, A.V.; Jennings, L.J.; Lavery, P.; Tew, D.G. Inhibition of herpes proteases and antiviral activity of 2-substituted thieno[2,3-d]oxazinones. Bioorg. Med. Chem. Lett., 1999, 9(3), 443-448.
[http://dx.doi.org/10.1016/S0960-894X(99)00004-9] [PMID: 10091699]
[35]
Gütschow, M.; Kuerschner, L.; Neumann, U.; Pietsch, M.; Löser, R.; Koglin, N.; Eger, K. 2-(diethylamino)thieno1,3ŏxazin-4-ones as stable inhibitors of human leukocyte elastase. J. Med. Chem., 1999, 42(26), 5437-5447.
[http://dx.doi.org/10.1021/jm991108w] [PMID: 10639285]
[36]
Gütschow, M.; Neumann, U. Novel thieno[2,3-d][1,3]oxazin-4-ones as inhibitors of human leukocyte elastase. J. Med. Chem., 1998, 41(10), 1729-1740.
[http://dx.doi.org/10.1021/jm9708341] [PMID: 9572899]
[37]
Jarvest, R.L.; Connor, S.C.; Gorniak, J.G.; Jennings, L.J.; Serafinowska, H.T.; West, A. Potent selective thienoxazinone inhibitors of herpes proteases. Bioorg. Med. Chem. Lett., 1997, 7, 1733-1738.
[http://dx.doi.org/10.1016/S0960-894X(97)00300-4]
[38]
Boehm, R. New pyrazole compounds. Part 2. Pharmazie, 1990, 45, 282-283.
[39]
Townsend, L.B.; Beylin, V.G.; Wotring, L.L. Synthesis, biochemical and chemotherapeutic activity of some azolo[1,3]oxazine nucleosides. Nucleosides Nucleotides Nucleic Acids, 1985, 4, 29-66.
[http://dx.doi.org/10.1080/07328318508077829]
[40]
Venkatesan, A.M.; Mansour, T. Preparation of bicyclic 6- alkylidene-penems as β-lactamase inhibitors for use against bacterial infections or diseases. WO Patent 2003093279A1, 2003.
[41]
Kato, T.; Katagiri, N. 3-(β-D-Ribofuranosyl)pyrazolo[3,4- e][1,3]oxaziro-5,7-dione as a virucide.U.S. Patent 4656260,
[42]
Ogawa, K.; Terada, T.; Honna, T. Syntheses of pyrazolo[1,2-a]pyrazole and pyrazolo[5,1-b][1,3]oxazine derivatives1). Chem. Pharm. Bull. (Tokyo), 1984, 32, 930-939.
[http://dx.doi.org/10.1248/cpb.32.930]
[43]
Kolasa, T.; Patel, M.V. Sulfonylphenylpyrazoles as COX-2 inhibitors. WO2001016138, 2001.
[44]
Merchan, F.L. Preparation of 4-oxo-1-phenyl-6-sulfonylamino-1H,4H-pyrazolo[3,4-d][1,3]oxazines. Synthesis, 1981, 12, 965.
[http://dx.doi.org/10.1055/s-1981-29660]
[45]
Dawood, K.M.; Farghaly, T.A.; Raslan, M.A. Heteroannulation routes to bioactive pyrazolooxazines. Curr. Org. Chem., 2020, 24, 1943-1975.
[http://dx.doi.org/10.2174/1570179417999200628035124]
[46]
Behbehani, H.; Dawood, K.M.; Farghaly, T.A. Biological evaluation of benzosuberones. Expert Opin. Ther. Pat., 2018, 28(1), 5-29.
[http://dx.doi.org/10.1080/13543776.2018.1389898] [PMID: 28994619]
[47]
Farghaly, T.A.; Gomha, S.M.; Dawood, K.M.; Shaaban, M.R. Synthetic routes to benzosuberone-based fused- and spiro- heterocyclic ring systems. RSC Advances, 2016, 6, 17955-17979.
[http://dx.doi.org/10.1039/C5RA26474J]
[48]
Muhammad, Z.A.; Farghaly, T.A.; Althagafi, I.; Al-Hussain, S.A.; Zaki, M.E.A.; Harras, M.F. Synthesis of antimicrobial azoloazines and molecular docking for inhibiting COVID-19. J. Heterocycl. Chem., 2021, 58(6), 1286-1301.
[http://dx.doi.org/10.1002/jhet.4257] [PMID: 34230687]
[49]
Dawood, K.M.; Farghaly, T.A. Thiadiazole inhibitors: A patent review. Expert Opin. Ther. Pat., 2017, 27(4), 477-505.
[http://dx.doi.org/10.1080/13543776.2017.1272575] [PMID: 27976971]
[50]
Dawood, K.M.; Abbas, A.A. Synthetic routes to bioactive bipyrazole derivatives. ChemistrySelect, 2021, 6, 279-305.
[http://dx.doi.org/10.1002/slct.202003436]
[51]
Shamroukh, A.H.; Rashad, A.E.; Abdel-Megeid, R.E.; Ali, H.S.; Ali, M.M. Some pyrazole and pyrazolo[3,4-d]pyrimidine derivatives: Synthesis and anticancer evaluation. Arch. Pharm. (Weinheim), 2014, 347(8), 559-565.
[http://dx.doi.org/10.1002/ardp.201400064] [PMID: 24801813]
[52]
Sweeney, M.J.; Davis, F.A.; Gutowski, G.E.; Hamill, R.L.; Hoffman, D.H.; Poore, G.A. Experimental antitumor activity of pyrazomycin. Cancer Res., 1973, 33, 2619-2623.
[53]
Nassar, I.F.; Atta-Allah, S.R.; Elgazwy, A-S.S.H. A convenient synthesis and molecular modeling study of novel pyrazolo[3,4-d]pyrimidine and pyrazole derivatives as anti-tumor agents. J. Enzyme Inhib. Med. Chem., 2015, 30(3), 396-405.
[http://dx.doi.org/10.3109/14756366.2014.940936] [PMID: 25068728]
[54]
Lei, H.; Sheng, X.; Zhao, Z.; Hao, M.; Lu, J. Application of 3, 5- dinitrophenyl-pyrazolo[3,4-d][1,3]-oxazine as tumor drug resistance reversal agent. CN Patent 112402425A, 2020.
[55]
El-Borai, M.A.; Rizk, H.F.; Sadek, M.R.; El-Keiy, M.M. An eco-friendly synthesis of heterocyclic moieties condensed with pyrazole system under green conditions and their biological activity. Green Sustain. Chem., 2016, 6, 88-100.
[http://dx.doi.org/10.4236/gsc.2016.62008]
[56]
Abdelrahman, E.F.; Shehta, W.; Assy, M.G.M.; Farhan, M.E. Synthesis of pyrano, pyrido, oxazino, and spiro pyrazole derivatives and their antimicrobial activity. Russ. J. Org. Chem., 2020, 56, 1832-1839.
[http://dx.doi.org/10.1134/S1070428020100267]
[57]
Borad, M.A.; Bhoi, M.N.; Rajani, D.P.; Rajani, S.D.; Patel, H.D. Synthesis and antimicrobial activities of 2-(4-substitutedphenyl)- 1,10B-dihydrospiro-[benzo[e]pyrazolo[1,5-c][1,3]oxazine-5,3′- indolin]-2′-one derivative from isatin. World J. Pharm. Pharm. Sci., 2014, 3, 805-821.
[58]
Bildirici, A.; Sener, I.T. Further derivatives of 4-benzoyl-1,5-diphenyl-1Hpyrazole-3-carboxylic acid and their antibacterial activities. Med. Chem. Res., 2007, 16, 418-426.
[http://dx.doi.org/10.1007/s00044-007-9082-z]
[59]
Cetin, A.; Bildirici, I. A study on synthesis and antimicrobial activity of 4-acyl-pyrazoles. J. Saudi Chem. Soc., 2018, 22, 279-296.
[http://dx.doi.org/10.1016/j.jscs.2016.05.008]
[60]
Abdou, W.M.; Barghash, R.F.; Bekheit, M.S. Carbodiimides - key mediators in the synthesis of novel cytotoxic and analgesic/antiinflammatory motifs based on a-amino-, enaminophosphonates, and azaphosphones. RSC Adv., 2013, 3, 1528-1540.
[http://dx.doi.org/10.1039/C2RA22769J]
[61]
Wang, Y.; Zhao, L.; Shen, H.; Wang, D.; Zhang, X.; Ye, J.; Ge, C.; Liu, X.; Zhang, J.; Chen, H. Preparation of benzo[e]pyrazolo[1,5- c][1,3]oxazine compound and its application as anti-hepatitis. CN Patent 106008552A2, 2016.
[62]
Mccomas, C. C.; Liverton, N. J.; Habermann, J.; Koch, U.; Narjes, F.; Li, P.; Peng, X.; Soll, R.; Wu, H. Heterocyclic-substituted benzofuran derivatives and methods of use thereof for the treatment of viral diseases. WO Patent 2013033901A1, 2013.
[63]
Jakobsen, P.; Horneman, A.M.; Persson, E. Inhibitors of the tissue factor/factor VIIa-induced coagulation: Synthesis and in vitro evaluation of novel 2-aryl substituted pyrid. Bioorg. Med. Chem., 2000, 8(12), 2803-2812.
[http://dx.doi.org/10.1016/S0968-0896(00)00207-8] [PMID: 11131171]
[64]
Ranatunge, R.R.; Garvey, D.S.; Janero, D.R.; Letts, L.G.; Martino, A.M.; Murty, M.G.; Richardson, S.K.; Young, D.V.; Zemetseva, I.S. Synthesis and selective cyclooxygenase-2 (COX-2) inhibitory activity of a series of novel bicyclic pyrazoles. Bioorg. Med. Chem., 2004, 12(6), 1357-1366.
[http://dx.doi.org/10.1016/j.bmc.2004.01.012] [PMID: 15018908]
[65]
Varano, F.; Catarzi, D.; Colotta, V.; Cecchi, L.; Filacchioni, G.; Galli, A.; Costagli, C. Structure-activity relationship studies of novel pyrazolo[1,5-c][1,3]benzoxazines: Synthesis and benzodiazepine receptor affinity. Arch. Pharm. (Weinheim), 1996, 329(12), 529-534.
[http://dx.doi.org/10.1002/ardp.19963291204] [PMID: 9038420]
[66]
Catarzi, D.; Cecchi, L.; Colotta, V.; Filacchioni, G.; Varano, F.; Martini, C.; Giousti, L.; Lucacchini, A. Synthesis of some 2-aryl-1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-ones as tools to define the essential pharmacophoric descriptors of a benzodiazepine receptor ligand. J. Med. Chem., 1995, 38(12), 2196-2201.
[http://dx.doi.org/10.1021/jm00012a020] [PMID: 7783151]
[67]
Thompson, A.M.; Blaser, A.; Anderson, R.F.; Shinde, S.S.; Franzblau, S.G.; Ma, Z.; Denny, W.A.; Palmer, B.D. Synthesis, reduction potentials, and antitubercular activity of ring A/B analogues of the bioreductive drug (6S)-2-nitro-6-[4-(trifluoromethoxy)benzyl]oxy-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824). J. Med. Chem., 2009, 52(3), 637-645.
[http://dx.doi.org/10.1021/jm801087e] [PMID: 19099398]
[68]
Abdel-Magid, A.F. Selective inhibitors of phosphodiesterase 4B (PDE-4B) may provide a better treatment for CNS, metabolic, autoimmune, and inflammatory diseases. ACS Med. Chem. Lett., 2017, 8(11), 1132-1133.
[http://dx.doi.org/10.1021/acsmedchemlett.7b00425] [PMID: 29152042]
[69]
Chappie, T.A.; Patel, N.C.; Verhoest, P.R.; Helal, C.J.; Sciabola, S.; Lachapelle, E.A.; Wager, T.T.; Hayward, M.M. 6,7-Dihydro- 5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide compounds. WO Patent 2017145013A1, 2017.
[70]
Stafford, J.A.; Veal, J.M.; Trzoss, L.L.; McBride, C. Chemical compounds as inhibitors of interleukin-1 activity. WO Patent 2018136890A1, 2018.
[71]
Bryan, M.C.; Drobnick, J.; Gobbi, A.; Katsumoto, T.; Rajapaksa, N.; Kiefer, J.R. Benzofurans as IRAK4 modulators. WO Patent 2018234343A1, 2018.
[72]
Mc Bride, C.; Trzoss, L. L.; Boloor, A.; Sokolova, N.; Pastor, R. M.; Staben, S. T.; Stivala, C.; Volgraf, M.; Bronner, S. M. Sulfonimidamide compounds as inhibitors of interleukin-1 activity. WO Patent 2020018975A1, 2020.
[73]
Stafford, J. A.; Veal, J. M.; Trzoss, L. L.; Mc Bride, C.; Pastor, R. M.; Staben, S. T.; Stivala, C.; Volgraf, M. Sulfonylurea compounds as inhibitors of interleukin-1 activity. WO Patent 2020018970A1, 2020.
[74]
Wohlfahrt, G.; Toermaekangas, O.; Salo, H.; Hoeglung, L.; Karjalainen, A.; Knuuttila, P.; Holm, P.; Rasku, S.; Vesalainen, A. Androgen receptor modulating compounds. WO Patent 2011051540A1, 2011.
[75]
Riva, C.; Graziani, D.; Longhi, M.; Callegari, E.; Frigerio, F.; Angelico, P. Heterocyclylmethylidene derivatives and their use as modulators of mGluR5 receptors. WO Patent 2019002571A1, 2019.
[76]
Green, J.; Hopkins, M.; Jones, B.; Kiryanov, A. A.; Kuehler, J.; Monenschein, H.; Murphy, S.; Nixey, T.; Sun, H. Piperidinyl- and piperazinyl-substituted heteroaromatic carboxamide as modulators of GPR6. WO Patent 2018183145A1, 2018.
[77]
Patel, S.; Hamilton, G.; Zhao, G.; Chen, H. Bicyclic amide compounds and methods of use thereof. WO Patent 2018100070A1, 2018.
[78]
Bonafoux, D.; Davis, H.M.; Frank, K.E.; Friedman, M.M.; Herold, J.M.; Hoemann, M.Z.; Huntley, R.; Osuma, A.; Sheppard, G.; Somal, G.K. Primary carboxamides as Btk inhibitors. WO Patent 2014210255A1, 2014.
[79]
Duncton, M.; O'Mahony, D. J. R.; Cox, M.; Estiarte-Martinez, M. L. A. Amides derivatives as ion-channel ligands, pharmaceutical compositions and methods of using the same. WO Patent 2009089057A1, 2009.
[80]
Roush, W.; Venkatraman, S.; Ghosh, S.; Shen, D.-M.; Katz, J.; Seidel, H.M. Compounds and compositions for treating conditions associated with NLRP activity. WO Patent 2020086732A1, 2020.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy