PL EN


Preferences help
enabled [disable] Abstract
Number of results
Journal
2004 | 2 | 1 | 141-187
Article title

Heterocyclic inflammation inhibitors

Content
Title variants
Languages of publication
EN
Abstracts
EN
Non steroidal anti-inflammatory drugs are the most widely used medicines for relief of pain. These drugs have some side effects, particularly toxicity in the gastrointestinal tract and kidneys. Various approaches have been used for obtaining safer anti-inflammatory drugs. In this review we have summarized the recent developments in the following areas; (i) mode of action of NSAIDs (ii) Role of COX-1 & COX-2 in inflammation, (iii) Different approaches used to improve gastric tolerance i.e. chemical manipulation, formulation & co-administration, development of non specific (COX-1 & COX-2 inhibitors) and specific (COX-2 inhibitors) inflammation inhibitors, and development of inflammation inhibitors having a mode of action other than COX-1 & COX-2 inhibition. We have also focused on the safety of COX-2 inhibitors and the synthesis of heterocyclic compounds and their role as inflammation inhibitors.
Publisher
Journal
Year
Volume
2
Issue
1
Pages
141-187
Physical description
Dates
published
1 - 3 - 2004
online
1 - 3 - 2004
References
  • [1] M.E. Wolff (Ed.): Burger’s Medicinal Chemistry. Part III, John Willy and sons, New York, 1981, pp. 1205–1271.
  • [2] D. Ratnasinghe, P.J. Daschner, M.R. Anver, B.H. Kasprzak, P.R. Taylor, G.C. Yeh and J.A. Tangrea: “Cyclooxygenase-2, P-glycoprotein-170 and drug resistance; is Chemoprevention against multidrug resistance possible”, Anticancer Research, Vol. 21(3C), (2001), pp. 2141–2147.
  • [3] W.A. Brown, S.A. Spinner, W.C. Malcontent, D. Vogiagis and P.E. O’Brien: “Non steroidal anti-inflammatory drugs with activity against either cyclooxygenase 1 or cyclooxygenase 2 inhibit colorectal cancer in a DMH rodent model by inducing apoptosis and inhibiting cell proliferation”, Gut, Vol. 48(5), (2001), pp. 660–666. http://dx.doi.org/10.1136/gut.48.5.660[Crossref]
  • [4] J.A. Mitchell and T.D. Warner: “Cyclo-oxygenase-2, Pharmacology, physiology, biochemistry and relevance to NSAID therapy”, Br. J. Pharmacol., Vol. 128(6), (1999), pp. 1121–1132. http://dx.doi.org/10.1038/sj.bjp.0702897[Crossref]
  • [5] G. Singh: “Recent consideration in non steroidal anti-inflammatory drug gastropathy”, Am. J. Med., Vol. 105(1B), (1998), pp. 31S-38S. http://dx.doi.org/10.1016/S0002-9343(98)00072-2
  • [6] L.A. Garc’aa Rodr’aguez: “Variability in risk of gastrointestinal complications with different non steroidal anti-inflammatory drugs”, Am. J. Med., Vol. 104, (1998), pp. 30S-34S. http://dx.doi.org/10.1016/S0002-9343(97)00208-8[Crossref]
  • [7] M. Schattenkirchner: “An updated safety profile of etodolac in several thousand patients”, Eur. J. Rheumatol. Inflamm., Vol. 10, (1990), pp. 56–65.
  • [8] H.A. Friendel, H.D. Langtry and M.M. Buckley: “Nabumetone. A reappraisal of its pharmacology and therapeutic use in rheumatic disease”, Drugs, Vol. 45, (1993), pp. 131–156.
  • [9] G.K. Mcevoy (Ed.): AHFS drug information, American society of hospital pharmacists Inc., Bethesda, 1992, pp. 1041–1126.
  • [10] W.L. Xie et al.: “Expression of a nitrogen-responsive gene encoding prostaglandin synthase regulated by m-RNA splicing”, Proc. Natl. Acad. Sci. USA, Vol. 88(7), (1991), pp. 2692–2696. http://dx.doi.org/10.1073/pnas.88.7.2692[Crossref]
  • [11] M. Feldman and A.T. McMahan: “Do cyclooxygenase-2 inhibitors provide benefits similar to those of traditional nonsteroidal anti-inflammatory drugs, with less gastrointestinal toxicity?”, Ann. Intern Med., Vol. 132(2), (2000), pp. 134–143.
  • [12] R.J. Flower: “Drugs which inhibit prostaglandin biosynthesis”, Pharmacol. Rev., Vol. 26(1), (1974), pp. 33–67.
  • [13] C.J. Hawkey: “COX-2 inhibitors”, Lancet, Vol. 353, (1999), pp. 307–314. http://dx.doi.org/10.1016/S0140-6736(98)12154-2[Crossref]
  • [14] A. Bertolini, A. Ottani and M. Sandrini: “Selective COX-2 Inhibitors and dual acting anti-inflammatory drugs: Critical remarks”, Current Medicinal Chemistry, Vol. 9(10), (2002), pp. 1033–1043. http://dx.doi.org/10.2174/0929867024606650[Crossref]
  • [15] L.S. Simon: “COX-2 inhibition. An advance or only pharmaceutical hype”, Arthritis care; Research, Vol. 45, (2001), pp. 209–215. http://dx.doi.org/10.1002/1529-0131(200106)45:3<209::AID-ART250>3.0.CO;2-A[Crossref]
  • [16] J.A. Oviedo and M. Wolfe: “Clinical potential of cyclooxygenase-2 inhibitors”, Bio Drugs, Vol. 15, (2001), pp. 563–572.
  • [17] V. Granados-Soto, R. Alonso-Lopez, R. Asomoza-Espinosa, M.O. Rufino, L.D. Gomes-Lopes and S.H. Ferrira: “Participation of COX, 1L-1β and TNFα in formalin-induced inflammatory pain”, Proceedings of the Western Pharmacology Society, Vol. 44, (2001), pp. 15–17.
  • [18] R.V. Martinez, M. Reval, D. Irene, M.D. Campos, J.A. Terron, R.A.M. Dominguez and F.J. Lopez-Munoz: “Involvement of peripheral cyclooxygenase-1 and cyclooxygenase-2 in inflammatory pain”, Journal of Pharmacy and Pharmacology, Vol. 54, (2002), pp. 405–412. http://dx.doi.org/10.1211/0022357021778475[Crossref]
  • [19] B. Nilsson, S. Friman and J. Svanvik: “Inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 regulates the microcirculation of the inflamed gall bladder”, Portland Press proceedings, Vol. 16, (2000), pp. 193; Chem. Abstr., Vol. 136, (2000), 277219z.
  • [20] O.J. Igwe, J.N. Murray and A.S. Moolwaney: “Interleukin 1-induced cyclooxygenase and nitric oxide synthase gene expression in the rat dorsal root ganglia is modulated antioxidants”, Neuroscience (Oxford), Vol. 105, (2001), pp. 971–985. [Crossref]
  • [21] T. Brzozowski, P.C. Konfurek, S.J. Konfurek, D. Schuppan, D. Drozdowicz, S. Kwiecien, J. Majka, T. Nakamura and E.G. Hahn: “Effect of local application of growth factors on gastric ulcer healing and mucosal expression of cyclooxygenase-1 and −2”, Digestion, Vol. 64, (2001), pp. 15–29. http://dx.doi.org/10.1159/000048835[Crossref]
  • [22] C.G. Egan, J.C. Lockhart, W.R. Ferrell, S.M. Day and J.S. Mclean: “Pathophysiological basis of acute inflammatory hyperemia in the rat knee: roles of cyclo-oxygenase-1 and −2”, Journal of Physiology (Cambridge), Vol. 539, (2002), pp. 579–587. http://dx.doi.org/10.1113/jphysiol.2001.013473[Crossref]
  • [23] J.L. Wallace, W. Mc Knight, B.K. Reuter, N. Vergnolle: “NSAID- induced gastric damage in rats: Requirement for inhibition of both cyclooxygenase 1 and 2”, Gastroenterology, Vol. 119, (2000), pp. 706–714. http://dx.doi.org/10.1053/gast.2000.16510[Crossref]
  • [24] B.M. Peskar: “Roles of cyclooxygenase isoforms in gastric mucosal defense”, Journal of Physiology (Paris), Vol. 95, (2001), pp. 3–9. http://dx.doi.org/10.1016/S0928-4257(01)00003-1[Crossref]
  • [25] B.F. Mc Adam, I.A. Mardini, A. Habib, A. Burke, J.A. Lawson, S. Kapoor and G.A. Fitz Gerald: “Effect of regulated expression of human cyclooxygenase isoform on eicosanoid and isocicosanoid production in inflammation”, J. Clin. Invest., Vol. 105, (2000), pp. 1473–1482. http://dx.doi.org/10.1172/JCI9523[Crossref]
  • [26] A.S. Kalgutkar and L.J. Marnett: “Amide derivatives for antiangiogenic and/or antitumorigenic use”, Chem. Abstr., Vol. 133, (2000), 99537c.
  • [27] A.S. Kalgutkar and L.J. Marnett: “Converting COX-inhibiting compounds to derivatives that are selective COX-2 inhibitors as non steroidal, anti-inflammatory drugs”, Chem. Abstr., Vol. 133, (2000), 99555j.
  • [28] W.C. Black, C. Bayly, M. Belley, C.C. Chan, S. Charleson, D. Denis, J.Y. Gauthier, R. Gordon, D. Guay, S. Kargman, C.K. Lau, Y. Leblanc, J. Mancini, M. Ouellet, D. Percival, P. Roy, K. Skorey, P. Tagari, P. Vickers, E. Wong, L. Xu and P. Prasit: “From Indomethacin to a selective COX-2 inhibitors. Development of indolalkanoic acids as potent and selective cyclooxygenase-2 inhibitors”, Bioorganic & Medicinal Chemistry Letters, Vol. 6, (1996), pp. 725–730. http://dx.doi.org/10.1016/0960-894X(96)00100-X[Crossref]
  • [29] C. Rordorf, N. Kellett, S. Mair, S. Milosavljev, J. Branson and G. Scott: “Gastroduodenal tolerability of lumiracoxib vs placebo and naproxen: a pilot endoscopic study in healthy male subjects”, Alimentary Pharmacology and Therapeutics, Vol. 18, (2003), pp. 533–541. http://dx.doi.org/10.1046/j.1365-2036.2003.01691.x[Crossref]
  • [30] A.S. Taha, N. Hudson, C.J. Hawkey, A.J. Swannell, P.N. Trye, J. Cottrell, S.G. Mass, T.J. Simon, R.D. Sturrock and R.N. Russell: “Famotidine for the prevention of gastric and duodenal ulcers caused by nonsteroidal anti-inflammatory drugs”, N. Engl. J. Med., Vol. 334, (1996), pp. 1435–1439. http://dx.doi.org/10.1056/NEJM199605303342204[Crossref]
  • [31] G.K. Mcevoy (Ed.): AHFS drug information, American society of hospital pharmacists Inc., Bethesda, 1992, pp. 1759–1763.
  • [32] J.E. Low: “Method of preventing ulcer formation caused by non steroidal anti-inflammatory drugs employing tetrazol-benzothiophene carboxamide compounds”, Chem. Abstr., Vol. 123, (1995), 102781f.
  • [33] C.S. Lai and T.M. Wang: “Protected forms of a conjugate combination of non-steroidal anti-inflammatory drugs (NSAIDs) and cyclooxygenase 2 (COX-2) inhibitors and their therapeutic use”, Chem. Abstr., Vol. 136, (2002), 15235f.
  • [34] S.A. Cooper: “Analgesic and anti-inflammatory compositions containing COX-2 inhibitors”, Chem. Abstr., Vol. 136, (2002), 42872t.
  • [35] P.C. Isakson, G.D. Anderson and S.A. Gregory: “Treatment of inflammation and inflammation related disorders with a combination of COX-2 inhibitors and a 5-lipoxygenase inhibitor”, Chem. Abstr., Vol. 133, (2000), 321880n.
  • [36] A.K. Tiwari and A. Mishra: “Synthesis and anti-inflammatory activities of N4, N5-di-substituted 3-methyl-1H-pyrazolo[3,4-c] pyridazines”, Bioorg. Med. Chem., Vol. 9, (2001), pp. 715–718. http://dx.doi.org/10.1016/S0968-0896(00)00285-6[Crossref]
  • [37] T. Niho, I. Yamamoto, H. Mochizuki, I. Kimura, A. Imai and T. Nakase: “Pyrazine and quinoxaline derivatives and their use as antiulcer agents”, Chem. Abstr., Vol. 124, (1996), 202307v.
  • [38] M. Fujitake, N. Mikami, H. Kasukawa, Y. Suwabe and A. Ota: “Preparation of pyrazine derivatives as blood platelet aggregation inhibitors and anti-inflammatory agents”, Chem. Abstr., Vol. 115, (1991), 71654v.
  • [39] T. Kaneko, R. Clark, N. Ohi, F. Ozaki, T. Kawahara, A. Kamada, K. Okano, H. Yokohama, K. Muramoto, T. Arai, M. Ohkuro, O. Takenaka and J. Sonoda: “Preparation of pyrazinobenzothiazine derivatives and analogs for the treatment of inflammation and autoimmune disease”, Chem. Abstr., Vol. 128, (1998), 204878p.
  • [40] K. Abe, F. Tafusa, J. Namikawa and Y. Manabe: “Preparation of heterocyclylaminophenols as inflammation inhibitors”, Chem. Abstr., Vol. 113, (1990), 231408g.
  • [41] T.A. Kelly and R.J. Sorcek: “Novel N-(pyridine-4-yl) nitrogen heterocyclic compounds useful in the treatment of inflammatory disease”, Chem. Abstr., Vol. 134, (2001), 131536n.
  • [42] T. Sohda, H. Makino, A. Baba and T. Yamane: “Thienopyridine derivatives as anti-inflammatory and antiarthritis agents”, Chem. Abstr., Vol. 132, (2000), 49954x.
  • [43] E.E. Knauss and P. Kumar: “Synthesis and anti-inflammatory activity of 5-(1,2-dihydropyridyl)2-tetrazoleacetic acids, esters and amides”, Eur. J. Med. Chem., Vol. 28, (1993), pp. 881–885. http://dx.doi.org/10.1016/0223-5234(93)90040-L[Crossref]
  • [44] R.M. Weier, P.W. Collins, M.A. Stealey, T.A. Barta and R.M. Huff: “4,5-Substituted imidazolyl compounds for the treatment of inflammation”, Chem. Abstr., Vol. 125, (1996), 33647u.
  • [45] I.K. Khanna, R.M. Weier, P.W. Collins, Y. Yu, X. Xu, R.M. Huff, R.A. Partis and F.J. Koszyk: “1,2-Substituted imidazolyl compounds for the treatment of inflammation”, Chem. Abstr., Vol. 125, (1996), 33646t.
  • [46] H. Yamada, T. Sugai, N. Kinoshita, Y. Goto, T. Sawara, N. Sueda, M. Yanai and K. Yamada: “Benzimidazole derivatives as asthma inhibitors and compositions containing benzimidazole derivatives”, Chem. Abstr., Vol. 126, (1997), 282801f.
  • [47] A.E. Braendstroem, P.L. Lindberg and G.E. Sunden: “Preparation of 2-(pyridine-2-yl methyl sulfinyl)-benziidazoles as gastric acid secretion inhibitors”, Chem. Abstr., Vol. 116, (1992), 174146f.
  • [48] T. Saito, N. Kawabe, T. Tanaka, E. Oomori and Y. Morya: “Preparation of aminopyridine derivatives as inflammation inhibitors”, Chem. Abstr., Vol. 126, (1997). 89267h.
  • [49] Y. Yoshikawa, H. Saito, Y. Ochi and K. Hatayama: “Preparation of 3-sulfonamidopyridine derivatives as anti-inflammatory antipyretic and antiallergy agents”, Chem. Abstr., Vol. 119, (1993), 117119n.
  • [50] K. Yoshikawa, M. Hasegawa, M. Suzuki, Y. Shimazaki, M. Ohtani, S. Saito and M. Goi: “Preapartion of nitrosulfonamidopyridine derivatives as anti-inflammatory antipyretic and analgesic”, Chem. Abstr., Vol. 128, (1998), 61428d.
  • [51] X. Collins, J.M. Robert, M. Duflos, G. Wielgosz, B.G. Le, C. Robin-Dubigenon, N. Grimaud, F. Lang and J.Y. Petit: “Synthesis of N-pyridinyl (methyl)-1,2-dihydro-4-hydroxy-2-oxoquinoline-3-carboxamides and analogs and their anti-inflammatory activity in mice and rats”, J. Pharm. Pharmacol., Vol. 53, (2001), pp. 417–423. http://dx.doi.org/10.1211/0022357011775505[Crossref]
  • [52] D.J. Hogenkamp, P. Nguyen and B. Shao: “Preparation of aryl substituted pyridines, pyrimidines, pyrazines and triazines with anticonsulsant and sodium channel blocking activity”, Chem. Abstr., Vol. 135, (2001), 257270k.
  • [53] Shibata and H. Sakatani: “Preparation of substituted pyrimidine derivatives as analgesics and anti-inflammatory agents”, Chem. Abstr., Vol. 122, (1995), 290883s.
  • [54] S. Paul, M. Gupta and R. Gupta: “Environmentally desirable synthesis without the use of organic solvent: Synthesis of 6-aryl-2 [(carboxymethyl) thio]-5-cyanopyrimidin-4(3H) one”, Indian J. Heterocyclic Chem., Vol. 9, (2000), pp. 313–314.
  • [55] N. Kinton, P. Meghani and S. Thom: “Preparation of pyrmidinediones and thioxypyrimidinones as P2-purinoceptor 7-transmembrane (TM) G-protein coupled receptor antagonists”, Chem. Abstr., Vol. 131, (1999), 19017f.
  • [56] J.W. Lee, B.Y. Lee, C.S. Kim, S.K. Lee and S.J. Lee: “Preparation of novel pyrimidine derivatives as gastric acid secretion inhibitors”, Chem. Abstr.,Vol. 132, (2000), 347584h.
  • [57] B.J. Benson, X. Chen, G.J. Cianciolo, J. Diaz, K.S. Ishaq, S.L. Morris-Natschke, R.J. Uhing and H. Wong: “Preparation of hydroxyalkyl ammonium-pyrimidines or purines and nucleoside derivatives, useful as inhibitors of inflammatory cytokines”, Chem. Abstr., Vol. 124, (1996), 261623t.
  • [58] G. Myakushkene, E. Udrenaite, P. Gaidyalis and P. Vainilavichyus: “Synthesis and anti-inflammatory activity of 4,6-diphenyl-2-pyrimidine carboxylic acid amides”, Pharm. Chem. J., Vol. 33, (1999), pp. 24–26. http://dx.doi.org/10.1007/BF02508412[Crossref]
  • [59] P.J. Vainilavichyus, V. Yu. Syadyaryavichyute, P.G. Gaidyalis and L.F. Gumbaragite: “Synthesis and anti-inflammatory activity of 4-substituted-2-isopropylthiopyrimidines”, Khim-Farm. Zh., Vol. 27, (1993), pp. 17–19.
  • [60] A. Ranise, O. Bruno, F. Bondavalli, S. Schenone, M. D’Amico, M. Falciani, W. Filippelli and F. Rossi: “5-Substituted-2,3-dihydro-6-mercapto-1,3-diphenyl-2-thioxo-4(3H)-pyrimidinones and their 6-(acylthio)derivatives with platelet antiaggregating anti-inflammatory, antiarrhythmic, antihyperlipidemic and other activities”, Farmaco, Vol. 49, (1994), pp. 551–558.
  • [61] R.K. Sahu, A. Magan, B. Gupta, S.M. Sondhi, R.C. Srimal and G.K. Patnaik: “Reactions of 4-isothiocyanato-4-methyl-2-pentanone with amines having functional groups at β position and anti-inflammatory evaluation of resulting heterocyclic compounds”, Phosphorus, Sulfur and Silicon, Vol. 88, (1994), pp. 45–51.
  • [62] S.M. Sondhi, R.P. Verma, N. Singhal, R. Shukla, R. Raghubir and M.P. Dubey: “Antiinflammatory and analgesic activity evaluation of some thiocarbamate thiourea, bisthiourea, acridine acridone and pyrimidine derivatives”, Indian Drugs, Vol. 36, (1999), pp. 50–54.
  • [63] S.M. Sondhi, M. Johar, N. Singhal, S.G. Dastidar, R. Shukla and R. Raghubir: “Synthesis and anticancer, anti-inflammatory and analgesic activity evaluation of some sulpha drug and acridine derivatives”, Monatsh Chem., Vol. 131, (2000), pp. 511–520. http://dx.doi.org/10.1007/s007060050332[Crossref]
  • [64] S.M. Sondhi, A. Magan, R.K. Sahu, V.K. Mahesh, R. Shukla and G.K. Patnaik: “Evaluation of some anti-inflammatory pyrimidobenzimidazoles synthesized via Noval Tin (II) Chloride-Hydrochloride acid assisted water addition and reduction of 4,4,6-trimethyl-1(2-nitroaryl)-1,4-dihydropyrimidine-2(3H)-thiones”, Synthesis, Vol. 11, (1994), pp.1175–1180. http://dx.doi.org/10.1055/s-1994-25667[Crossref]
  • [65] S.M. Sondhi, V.K. Sharma, R.P. Verma, N. Singhal, R. Shukla, R. Raghubir and M.P. Dubey: “Synthesis, anti-inflammatory and analgesic activity evaluation of some mercaptopyrimidine and pyrimidobenzimidazole derivatives”, Synthesis, Vol. 5, (1999), pp. 878–884. http://dx.doi.org/10.1055/s-1999-3472[Crossref]
  • [66] S.M. Sondhi, R.P. Verma, N. Singhal, V.K. Sharma, R. Shukla and G.K. Patnaik: “Antiinflammatory and analgesic activity evaluation of heterocyclic compounds synthesized by the reaction of 4-isothiocyanato-4-methyl-2-pentanone with amines”, Phosphorus Sulphur & Silicon, Vol. 118, (1996), pp. 7–19.
  • [67] S.M. Sondhi, M. Johar, S. Rajvanshi, S.G. Dastidar, R. Shukla, R. Raghubir and J.W. Lown: “Anticancer, anti-inflammatory and analgesic activity evaluation of heterocyclic compounds synthesized by the reaction of 4-isothiothiocyanato-4-methylpentan-2-one with substituted o-phenylenediamines, o-diaminopyridine and (un) substituted o-diaminopyrimidines”, Aust. J. Chem., Vol. 54, (2001), pp. 69–74. http://dx.doi.org/10.1071/CH00141[Crossref]
  • [68] S.M. Sondhi, N. Singhal, R.P. Verma, S.K. Arora, R. Shukla and R. Raghubir: “Synthesis and anti-inflammatory and anticancer activity evaluation of some condensed pyrimidines”, Monatsh Chem., Vol. 131, (2000), pp. 501–509. http://dx.doi.org/10.1007/s007060050331[Crossref]
  • [69] S.M. Sondhi, M. Johar, R. Shukla, R. Raghubir, N. Bharti and A. Azam: “Synthesis, anti-inflammatory, analgesic and antiamoebic activity evaluation of some pyrimidobenzimidazole and pyrimidopyridoimidazole derivatives”, Aust. J. Chem., Vol. 54, (2001), pp. 461–467. http://dx.doi.org/10.1071/CH01055[Crossref]
  • [70] S.M. Sondhi, S. Rajvanshi, M. Johar, N. Bharti, A. Azam and A.K. Singh: “Antiinflammatory, analgesic and antiamoebic activity evaluation of pyrimido [1,6-a] benzimidazole derivatives synthesized by the reaction of ketoisothiocyanates with mono and diamines”, Eur. J. Med. Chem., Vol. 37, (2002), pp. 835–843. http://dx.doi.org/10.1016/S0223-5234(02)01403-4[Crossref]
  • [71] S.S. Bhagwat, C.H. Lee, R.J. Perner and Y.C. Gu: “Preparation of 6,7-disubstituted 4-aminopyrido [2,3-d] pyrimidines as adenosine kinase inhibitors”, Chem. Abstr., Vol. 135, (2001), P152822p.
  • [72] A. Vidal, M.L. Ferrandiz, A. Ubeda, A. Acero-Alarcon, J. Sepulveda-Arques and M.J. Alcaraz: “Effect of imidazo [1,2-a] pyrimidine derivatives on leukocyte function”, Inflammation Res., Vol. 50, (2001), pp. 317–320. http://dx.doi.org/10.1007/PL00000250[Crossref]
  • [73] S. Laneri, A. Sacchi, M. Gallitelli, F. Arena, E. Lurachi, E. Abignente, W. Filippelli and F. Rossi: “Research on heterocyclic compounds-Part XXXIX. 2-Methyl-imidazo [1,2-a] pyrimidine-3-caroboxylic derivatives:Synthesis and anti-inflammatory activity”, Eur. J. Med. Chem., Vol. 33, (1998), pp. 163–170. http://dx.doi.org/10.1016/S0223-5234(98)80005-6[Crossref]
  • [74] C.J. Shishoo, T. Ravikumar, K.S. Jain, I.S. Rathod, T.P. Gandhi, M.C. Satia: “Synthesis of novel 1,2-(un) substituted-3-amino-5-aryl-6-arylaminopyrazolo [3,4-d] pyrimidin-4(5H) ones and their biological activities”, Indian J. Chem. Sec. B., Vol 38, (1999), pp. 1075–1085.
  • [75] M. Inoe, Y. Shoji, T. Okamura, K. Hashimoto, M. Obara and T. Yasuda: “Preparation of pyrazolo [1,5-a] pyrimidine derivatives as analgesics”, Chem. Abstr., Vol. 124, (1996), 317190u.
  • [76] C.J. Shishoo, U.S. Pathak, I.S. Rathod, K.S. Jain, C.G. Nargund, A.D. Taranalli, H. Patel, V. Kumar and V.S. Shirsath: “Synthesis and pharmacological evaluation of some novel 5-aryl-6-arylamine-1-phenylpyrazolo [3,4-d] pyrimidin-4(5H)-ones as analgesic and anti-inflammatory agents”, Indian J. Chem. Sec. B., Vol. 38, (1999), pp. 684–695.
  • [77] B. Tozkoparan, M. Ertan, B. Krebs, M. Laegs, P. Kelicen and R. Demirdamar: “Condensed heterocyclic compounds: Synthesis and anti-inflammatory activity of novel thiazolo [3,2-a] pyrimidines”, Arch. Pharm., Vol. 331, (1998), pp. 201–206. http://dx.doi.org/10.1002/(SICI)1521-4184(199806)331:6<201::AID-ARDP201>3.0.CO;2-T[Crossref]
  • [78] B. Tozkoparan, M. Ertan, P. Kelicen and R. Demirdamar: “Synthesis and antiinflammatory activity of some thiazolo [3,2-a] pyrimidines derivatives”, Farmaco, Vol. 54, (1999), pp. 588–593. http://dx.doi.org/10.1016/S0014-827X(99)00068-3[Crossref]
  • [79] S.S. Bhagwat, C.H. Lee, M.D. Cowart, J.A. Mckie, A.L. Grillot, A.O. Stewart, G.Z. Zheng and R.J. Perner: “Preparation of 5,7-disubstituted-4-aminopyrido [2,3-d] pyrimidines as adenosine kinase inhibitors”, Chem. Abstr., Vol. 132, (2000), 308351k.
  • [80] P. Molina, E. Aller, A. Lorenzo, P. Lopez-Cremades, I.U.A. Rioja, M.C. Terencio and M.J. Alcaraz: “Solid phase synthesis and inhibitory effects of some pyrido [1,2-c] pyrimidine derivatives on leukocyte functions and experimental inflammation”, J. Med. Chem., Vol. 44, (2001), pp 1011–1014. http://dx.doi.org/10.1021/jm000997g[Crossref]
  • [81] S. Oomura, N. Takenawa and S. Kamya: “A pyrimidine derivative for treatment of inflammatory bowel diseases”, Chem. Abstr., Vol. 123, (1995), 965b.
  • [82] E. Abignente, F. Arena, P. de Caprariis, E. Luraschi, A. Sacchi, E. Lampa, L. Berrino and D. Donnoli: “Research on heterocyclic compounds XXVIII. Imidazo [1,2-c] pyrimidines”, Farmaco, Vol. 46, (1991), pp. 1099–1110.
  • [83] E. Abignente, A. Sacchi, S. Laneri, F. Rossi, M. D’Amico, L. Berrino, V. Calderaro and C. Parrillo: “Research on heterocyclic compounds XXVII. Synthesis and Cyclooxygenase-indipendent anti-inflammatory and analgesic activity of imidazo-[1,2-a] pyrimidine derivatives”, Eur. J. Med. Chem., Vol. 29, (1994), pp. 279–286. http://dx.doi.org/10.1016/0223-5234(94)90097-3[Crossref]
  • [84] N.A. Santagati, A. Caruso, V.M.C. Cutuli and F. Caccamo: “Synthesis and pharmacological evaluation of thieno [2,3-d] pyrimidine-2,4-dione and 5H pyrimido [5,4]indole-2,4-dione derivatives”, Farmaco, Vol. 50 (1995), pp. 689–695.
  • [85] G. Romeo, F. Russo, A. Caruso, V. Cutuli and M. Amico-Roxas: “Synthesis of new thieno [2,3-d] pyrimidine-2,4-[1H,3H]diones with analgesic and anti-inflammatory activities”, Arzneim-Forsch, Vol. 48, (1998), pp. 167–172.
  • [86] D. Bozsing, P. Sohar, G. Gigler and G. Kovacs: “Synthesis and pharmaceutical study of new 3,4-dihydro-2H,6H-pyrimido [2,1-b] [1,3] thiazines”, Eur. J. Med. Chem., Vol. 31, (1996), pp. 663–668. http://dx.doi.org/10.1016/0223-5234(96)85874-0[Crossref]
  • [87] J. Bantick, M. Perry and P. Thorne: “Preparation of pyrimidine fused compounds as antiallergic and anti-inflammatory agents”, Chem. Abstr., Vol. 128, (1998), 140714x.
  • [88] A.N. Gaidukevich, G.P. Kazakov, A.A. Kravchenko, L.A. Porokhnyak, V.V. Pinchuk and D.L. Velikii: “Synthesis and biological activity of acridinyl-9-thioacetic acids and their derivatives”, Khim. Pharm. Zh., Vol. 21, (1987), pp. 1067–1070.
  • [89] I.B. Taraporewala and J.M. Kauffman: “Synthesis and structure activity relationships of anti-inflammatory 9,10-dihydro-9-oxo-2-acridinealkanoic acids and 4-(2-carboxyphenyl)amino benzene alkanoic acids”, J. Pharm. Sci., Vol. 79, (1990), pp. 173–178. http://dx.doi.org/10.1002/jps.2600790219[Crossref]
  • [90] W.E. Bondinell, Y.A. Reader and T.W.F. Ku: “Substituted bisacridines and related compounds as CCR5 receptor ligands, anti-inflammatory agents and antiviral Agents”, Chem. Abstr., Vol. 129, (1998), 122582u.
  • [91] S.M. Sondhi, N. Singhal, R.P. Verma, R. Raghubir, A.K. Goel and G. K. Patnaik: “Syntheis, anti-inflammatory and analgesic activity evaluation of some 2-(9-acridinylamino)pyridines and 2-(9-acridinylamino/imino)thiazolines”, Indian J. Chem. Sec. B., Vol. 36, (1997), pp. 620–624.
  • [92] S.M. Sondhi, V.K. Sharma, N. Singhal, R.P. Verma, R. Shukla, R. Raghubir and M.P. Dubey: “Synthesis and anti-inflammatory activity evaluation of some acridinyl amino antipyrine, acridinyl amino anthraquinone, acridino thiourea and thiazolino thiourea derivatives”, Phosphorus, Sulphur and Silicon, Vol. 156, (2000), pp. 21–33.
  • [93] S.M. Sondhi, M. Johar, R. Shukla, R. Raghubir and S.G. Dastidar: “Synthesis of sulphadrug acridine derivatives and their evaluation for anti-inflammatory, analgesic and anticancer activity”, Indian J. Chem. Sec. B., Vol. 41, (2002), 2659–2666.
  • [94] S.M. Sondhi, A. Magan, V.K. Mahesh, R.C. Srimal and A.K. Goel: “Synthesis, isomer identification by 2D-NMR and anti-inflammatory evaluation of some 9H-imidazolo [1,2-a] benzimidazole and perhydroimidazolo [1,2-d], [1,2,4] dithiazepine derivatives”, Indian J. Chem., Vol. 33B, (1994), pp. 1144–1149.
  • [95] L. Revesz: “Preparation of 2-substituted 4,5-diaryl imidazoloes as antiinflammatories and immunosuppressants”, Chem. Abstr., Vol. 130, (1999), 125072j.
  • [96] L.K. Labanauskas, A.B. Brukstus, P.G. Gaidelis, V.A. Buchinskaite, E.B. Udrenaite and V.K. Dauksas: “Synthesis and anti-inflammatory activity of some new 1-acylderivatives of 5,6-diethoxy-2-(methylthio)benzimidazole”, Pharm. Chem. J., Vol. 34, (2000), pp. 353–355. http://dx.doi.org/10.1023/A:1005213306544[Crossref]
  • [97] J.F. Eggler: “Preparation of benzisothiazoles derivatives as inhibitors of 5-lipoxygenase biosynthesis”, Chem. Abstr., Vol. 124, (1996), 117304x.
  • [98] T.A. Kelly and R.J. Sorcek: “Novel N-(pyridin-4-yl)nitrogen heterocyclic compounds useful in the treatment of inflammatory disease”, Chem. Abstr., Vol. 134, (2001), 131536n.
  • [99] T. Sohda, H. Makino, A. Baba and T. Yamane: “Thienopyridine derivatives as anti-inflammatory and antiarthritis agents”, Chem. Abstr., Vol. 132, (2000), 49954x.
  • [100] M. Kato, S. Nishida, H. Kita Sato, N. Sakata and S. Kawai: “Cyclooxygenase-1 and cyclooxygenase-2 selectivity of non-steroidal anti-inflammatory drugs: investigation using human peripheral monocytes”, Journal of Pharmacy and Pharmacology, Vol. 53, (2001), pp. 1679–1685. http://dx.doi.org/10.1211/0022357011778070[Crossref]
  • [101] Y. Hu and G. Cheng: “Establishment of screening models for selective cyclooxygenase-2 inhibitors”, Yaoxue Xuebao, Vol. 35, (2000), pp. 343–346.
  • [102] P. Kay-Mugford, S.J. Bori, J. LaMarre and P. Conlon: “In vitro effects of nonsteroidal anti-inflammatory drugs on cyclooxygenase activity in dogs”, Am. J. Vet. Res., Vol. 61, (2000), pp. 802–810. http://dx.doi.org/10.2460/ajvr.2000.61.802[Crossref]
  • [103] J.R. Vane and R.M. Botting: “Mechanism of action of anti-inflammatory drugs”, Int. J. Tissue React., Vol. 20, (1998), pp. 3–15.
  • [104] Z. Sui and M. Wachter: “Aryl phenyl hydrazides as selective COX-2 inhibitors for the treatment of inflammation”, Chem. Abstr., Vol. 133, (2000), 38226f.
  • [105] J. Berg, H. Fellier, T. Christoph, P. Kremminger, M. Hartman, H. Blaschke, F. Rovensky, R. Towart and D. Stimmeder: “Pharmacology of selective cyclooxygenase-1 inhibitor, HN-56249: a novel compounds exhibiting a marked preference for the human enzyme in intact cells”, Naunym-Schmiedeberg’s Arch. Pharmacol., Vol. 361, (2000), pp. 363–372. http://dx.doi.org/10.1007/s002109900192
  • [106] M. Pal, K.R. Yeleswarapu, R. Ramanujam, P. Misra, P.K. Mamnoor and S.R. Casturi: “Preparation of 3,4-diphenyl-2,5-dihydro-2-furanones as novel compounds having anti-inflammatory activity”, Chem. Abstr., Vol. 136, (2000), 5893e.
  • [107] C. Almansa, C. Gonzalez and M.C. Torres: “Novel imidazoles with anti-inflammatory activity and their preparation and use”, Chem. Abstr., 132, (2000), 308336j.
  • [108] I.K. Khanna, Yi. Yu, R.M. Huff, R.M. Weier, X. Xu, F.J. Koszyk, P.W. Collins, J.N. Cogburn, P.C. Isakson, C.M. Koboldt, J.L. Masferrer, W.E. Perkins, K. Seibert, A.W. Veenhuizen, J. Yuan, D.C. Yang, Y.Y. Zhang: “Selective cyclooxygenase-2-inhibitors: heteroaryl modified 1,2-diarylimidazoles are potent, orally active anti-inflammatory agents”, J. Med. Chem., Vol. 43, (2000), pp. 3168–3185. http://dx.doi.org/10.1021/jm0000719[Crossref]
  • [109] J.J. Talley, J.A. Sikorski, M.J. Graneto, J.S. Carter, B.H. Norma, B. Devadas and H.F. Lu: “Preparation of heterocycle substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors”, Chem. Abstr., Vol. 136, (2002), 69808p.
  • [110] S. Barkey, L. Goossens, T. Taverne, J. Cornet, V. Choesmel, C. Rouand, G. Gimeno, S. Yannic-Arnoult, C. Michaux, C. Charlier, R. Houssin and J.-P. Henichart: “Synthesis and activity of a new Methoxytetra-hydropyran derivatives as duel cyclooxygenase-2/5-Lipoxygenase inhibitor”, Bioorganic & Medicinal Chemistry Letters, Vol. 12, (2002), pp. 779–782. http://dx.doi.org/10.1016/S0960-894X(02)00013-6[Crossref]
  • [111] M.J. Graneto, S.J. Hartman, S. Metz, M.J. Talley, M.L. Vazquez, D.L. Brown, R.M. Weier, M.A. Stealey and X. Xu: “Preparation of heteroarylpyrazoles using dithietanses”, Chem. Abstr., Vol. 133, (2000), 4657g.
  • [112] M.R. Cuberes-Altisent, J.M. Berrocal-Romero, M.M. Contijoch-Llobet and J. Frigola-Constansa: “Diaryl pyrazoles as inhibitors of COX-2”, Chem. Abstr., Vol. 132, (2000), 12302g.
  • [113] K. Ando, T. Kato, A. Kawai and T. Nonomura: “Preparation of heterocyclyl sulfonylbenzene compounds as anti-inflammatory/analgesic agents”, Chem. Abstr., Vol. 132, (2000), 35714g.
  • [114] K. Ando, K. Kawamura, T. Kato, M.L. Minich, K.M. Lundy, H. Cheng, J. Li, B.S. Bronk, S.M. Sakya: “Synthesis and use of heteroaryl phenyl pyrazoles as anti-inflammatory/analgesic agents”, Chem. Abstr., Vol. 135, (2001), 19659z.
  • [115] K. Ando and K. Kawamura: “Preparation of sulfamoyal hetero aryl pyrazole compound as anti-inflammatory and analgesic agents”, Chem. Abstr., Vol. 135, (2001), 33472q.
  • [116] T. Ochi and T. Goto: “Antiinflammatory activity of a novel selective cyclooxygenase-2 inhibitor, FR 140423 on type II collagen-induced arthritis in Lewi’s rats”, Prostaglandins and other Lipid Mediators, Vol. 66, (2001), pp. 317–327. http://dx.doi.org/10.1016/S0090-6980(01)00171-X[Crossref]
  • [117] M.C. Carter, A. Naylor, M. Pass, J.J. Payne and N.A. Pegg: “Preparation of substituted pyrimidines as selective cyclooxygenase-2 inhibitors”, Chem. Abstr., Vol. 136, (2002), 216760x.
  • [118] J. Ishida, H. Yamamoto, N. Konishi, M. Morita, K. Nakamura, S. Miyata, T. Ochi, Y. Morita, E. Yoshimi and K. Kuroda: “Preparation of 3-aryl pyridines as cyclooxygenase inhibitors”, Chem. Abstr., Vol. 137, (2002), 109211b.
  • [119] R.M. Weier, L.F. Lee, R.A. Partis and F.J. Koszyk: “Preparation of 2,3-diarylpyridines as selective cyclooxygenase-2-inhibitors”, Chem. Abstr., Vol. 131, (1999), 73565w.
  • [120] D. Dube, R. Fortin, R. Friesen, Z. Wang and J.X. Gauthier: “Preparation of substituted pyridines as as cyclooxygenase inhibitors”, Chem. Abstr., Vol. 128, (1998), 140614q.
  • [121] C. Black, G. Hughes and Z. Wang: “Prepartion of pyridinyl-2-cyclopenten-1-ones as selective cyclooxygenase-2 inhibitors”, Chem. Abstr., Vol. 128, (1998), 13207j.
  • [122] K.L. McLaren, D.B. Smith and J.L. Tracy: “Preparation of benzofuran-2-carbonitriles and benzothiophene-2-carbonitriles as anti-inflammatory agents”, Chem. Abstr., Vol. 137, (2002), 20293y.
  • [123] H.S. Shin, M.S. Park and S.K. Kwon: “Anti-inflammatory evaluation and synthesis of benzothiazine derivatives as cycloxygenase-2-inhibitor”, Yakhak Hoechi, Vol. 44, (2000), pp. 272–278.
  • [124] G.J. Dear and K. Gohil: “Preparation of pyrazolo [1,5-b] pyridazines as selective inhibitors of COX-2”, Chem. Abstr., Vol. 136, (2002), 340687t.
  • [125] I.B. Campbell and A. Naylor: “Preparation of pyrazolopyridines as selective inhibitors of COX-2 inhibitors”, Chem. Abstr., Vol. 132, (2000), 321858a.
  • [126] P.J. Beswick, I.B. Campbell and A. Naylor: “Preparation of cyclo oxygenase-2-inhibiting-2, 3-diphenylimidazo [1,2-a] pyridine anti inflammatories”, Chem. Abstr., Vol. 126, (1997), 8117j.
  • [127] J.S. Carter, M.G. Obukowicz, B. Devadas, J.J. Talley, D.L. Brown, M.J. Graneto, S.R. Bertenshaw, D.J. Jr. Rogier, S.R. Nagarajan, C.E. Hanan, S.J. Hartmann, C.L. Ludwig, S. Metz and D.E. Korte: “Preparation of benzopyran carboxylates and quinoline carboxylates as selective cyclooxygenase-2-inhibitors”, Chem. Abstr., Vol. 133, (2000), 43440a.
  • [128] M.N. Riera: “Selective anti-inflammatory inhibitors of 2-cyclo-oxygenase”, Cienc, Tecnol. Pharm., Vol. 9, (1999), pp. 157–164.
  • [129] M.S. Borges, H.A. Capriles, F.F. Caballero and C.R. Perez: “Tolerability to new COX-2 inhibitors in NSAIDs-sensitive patients with cutaneous reactions”, Annals of Allergy, Asthma & Immunology, Vol. 87, (2001), pp. 201–204. http://dx.doi.org/10.1016/S1081-1206(10)62226-0[Crossref]
  • [130] C. Brideau, S.C. Van and C.C. Chan: “In vitro effects of cyclo oxygenase inhibitors in whole blood of horses, dogs and cats”, American Journal of Veterinary Research, Vol. 62, (2001), pp. 1755–1760. http://dx.doi.org/10.2460/ajvr.2001.62.1755[Crossref]
  • [131] U. Mahadevan, E.V. Jr. Loftus, W.J. Tremaine and W.J. Sandborn: “Safety of selective cyclooxygenase-2-inhibitors in inflammatory bowel disease”, American Journal of Gasteroenterology, Vol. 97, (2002), pp. 910–917. http://dx.doi.org/10.1111/j.1572-0241.2002.05608.x[Crossref]
  • [132] I. Tegeder, J. Pfeilschiffer and G. Geisslinger: “Cyclooxygenase-independent actions of cyclooxygenase inhibitors”, FASEB Journal, Vol. 15, (2001), pp. 2057–2072. http://dx.doi.org/10.1096/fj.01-0390rev[Crossref]
  • [133] G. Di Girolamo, A. Franchi, A.R. De Las Santos, M.L. Marti, M. Farina, D.G. Fernandez and A. Mortha: “Effect of nonsteroidal anti-inflammatory drugs on lipoxygenase and cyclooxygenase activities on human colon segments from patients with neoplasia”, Medicina (Buenas Aries, Argentina), Vol. 61(5/1), (2001), pp. 566–572.
  • [134] Y. Wu, R. Chen, J. Chen, A. Zhang and X. Pan: “IL-10 downregulates expression of cyclooxygenase-2 and its mediated PGE2 production in human mesangial cells”, Mianyixue Zazhi, Vol. 17, (2001), pp. 421–424.
  • [135] T. Sato, T.Taguchi, H. Nakano, T. Inoue and N. Kawasaki: “Preparation of 1,2-substituted benzimidazole derivatives as antiallergic agents”, Chem. Abstr., Vol. 133, (2000), 238002s.
  • [136] M.J. Suto, M.E. Goldman, L.M. Gayo, L.J. Ransome-Fong, M.S.S. Palanki and R.W. Sullivan: “Preparation of pyrimidinecarboxamides and Pyrazine carboxamides for treating inflammatory conditions”, Chem. Abstr., Vol. 126, (1997), 264109g.
  • [137] S. Yasufuka and A. Motonaga: “Preparation of imidazopyridine derivatives as inflammation inhibitors”, Chem. Abstr., Vol. 120, (1994), 164170c.
  • [138] T. Komatsu, Y. Kawaharra, T. Fuji, M. Takano and N. Hara: “Preparation of N-pyridylmethoxybenzyl)-N-hydroxy ureas as lipoxygenase inhibitors and thromboxane synthetase inhibitors”, Chem. Abstr., Vol. 125, (1996), 247620d.
  • [139] J. Varghese, R.R. Rydel and S. Michael: “Preparation of 4-benzyl-2-phenylpyrimidine phospholipase A2 inhibitors”, Chem. Abstr., Vol. 132, (2000), 347577h.
  • [140] R. Austin, A. Baxter, R. Bonnett, F. Hunt, F. Kinchin and P. Willis: “Preparation of novel thiazolopyrimidines as modulators of chemokine receptor activity”, Chem. Abstr., Vol. 132, (2000), 166252c.
  • [141] J.S. Skotnicki and S.C. Gilman: “Preparation of 1,2,3,4-tetrahydro acridines and analogs as inhibitors of interleukin I”, Chem. Abstr., Vol. 112, (1990), 118672e.
  • [142] M. Wachter and S.A. Beers: “Preparation of 2-substituted imidazoles useful in the treatment of inflammatory diseases”, Chem. Abstr., Vol. 130, (1999), 139340g.
  • [143] S.A. Beers, E. Malloy, M.P. Wachter and W. Wu: “Preparation of substituted imidazoles useful in the treatment of inflammatory diseases”, Chem. Abstr., Vol. 129, (1998), 330728y.
  • [144] D.A. Willoghby, A.R. Moore, N. Colville and R. Paul: “COX-1, COX-2 and COX-3 and the future treatment of Chronic inflammatory disease”, Lancet, Vol. 355(9204), (2000), pp. 646–648. http://dx.doi.org/10.1016/S0140-6736(99)12031-2[Crossref]
Document Type
Publication order reference
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_BF02476188
Identifiers
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.