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Volumn 16, Issue 4-5, 2002, Pages 221-228

Synthesis and pharmacological profile of 6-methyl-3-isopropyl-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide derivatives: Non-steroidal anti-inflammatory agents with reduced ulcerogenic effects in the rat

Author keywords

Non steroidal anti inflammatory; Piroxicam; Rat; Synthesis; Ulcerogenic

Indexed keywords

ASSAYS; ORGANIC COMPOUNDS; PH EFFECTS; SPECTRUM ANALYSIS; SYNTHESIS (CHEMICAL);

EID: 0036743318     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0928-0987(02)00046-5     Document Type: Article
Times cited : (27)

References (29)
  • 1
    • 1542525701 scopus 로고    scopus 로고
    • Intramolecular anionic Friedel-Crafts equivalents. An expeditious synthesis of 4H-1,2-benzothiazin-4-one 1,1-dioxides from N-arylsulfonylated amino acids
    • Bakker, W.I.I., Familoni, O.B., Padfield, J., Snieckus, V., 1997. Intramolecular anionic Friedel-Crafts equivalents. An expeditious synthesis of 4H-1,2-benzothiazin-4-one 1,1-dioxides from N-arylsulfonylated amino acids. Synlett. 1079-1080.
    • (1997) Synlett. , pp. 1079-1080
    • Bakker, W.I.I.1    Familoni, O.B.2    Padfield, J.3    Snieckus, V.4
  • 2
    • 0032777898 scopus 로고    scopus 로고
    • The analgesic NSAID lornoxicam inhibits cyclooxygenase (COX)-1/-2, inductible nitric oxide synthase (iNOS), and the formation of interleukin (IL)-6 in vitro
    • Berg J., Fellier H., Christoph T., Grarup J., Stimmeder D. The analgesic NSAID lornoxicam inhibits cyclooxygenase (COX)-1/-2, inductible nitric oxide synthase (iNOS), and the formation of interleukin (IL)-6 in vitro. Inflamm. Res. 48:1999;369-379.
    • (1999) Inflamm. Res. , vol.48 , pp. 369-379
    • Berg, J.1    Fellier, H.2    Christoph, T.3    Grarup, J.4    Stimmeder, D.5
  • 3
    • 0023244957 scopus 로고
    • Analogues and derivatives of tenoxicam. Synthesis and anti-inflammatory activity of analogues with different residues on the ring nitrogen and the amide nitrogen
    • Binder D., Hromatka O., et al. Analogues and derivatives of tenoxicam. Synthesis and anti-inflammatory activity of analogues with different residues on the ring nitrogen and the amide nitrogen. J. Med. Chem. 30:1987;678-682.
    • (1987) J. Med. Chem. , vol.30 , pp. 678-682
    • Binder, D.1    Hromatka, O.2
  • 4
    • 85045552781 scopus 로고
    • A convenient method for the preparation of enantiomerically pure 2-substituted N-tosylaziridines
    • Craig, D., Berry, M.B., 1992. A convenient method for the preparation of enantiomerically pure 2-substituted N-tosylaziridines. Synlett. 41-44.
    • (1992) Synlett. , pp. 41-44
    • Craig, D.1    Berry, M.B.2
  • 5
    • 0026653597 scopus 로고
    • Effects of non-steroidal anti-inflammatory drugs on endogenous GI prostaglandins and therapeutic strategies for prevention and treatment of non-steroidal anti-inflammatory drug-induced damage
    • Cryer B., Feldman M. Effects of non-steroidal anti-inflammatory drugs on endogenous GI prostaglandins and therapeutic strategies for prevention and treatment of non-steroidal anti-inflammatory drug-induced damage. Arch. Intern. Med. 152:1992;115.
    • (1992) Arch. Intern. Med. , vol.152 , pp. 115
    • Cryer, B.1    Feldman, M.2
  • 7
    • 0026072975 scopus 로고
    • Chemistry of oxaziridines 16. A short, highly enantioselective synthesis of the AB-ring segments of γ-rhodomycinone and α-citromycinone using (+)-[(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine
    • Davis F.A., Kumar A., Chen B.-C. Chemistry of oxaziridines 16. A short, highly enantioselective synthesis of the AB-ring segments of γ-rhodomycinone and α-citromycinone using (+)-[(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine. J. Org. Chem. 56:1991;1143-1145.
    • (1991) J. Org. Chem. , vol.56 , pp. 1143-1145
    • Davis, F.A.1    Kumar, A.2    Chen, B.-C.3
  • 8
    • 0031696493 scopus 로고    scopus 로고
    • Improvement in gastrointestinal tolerability of the selective cyclooxygenase (COX)-2 inhibitor, meloxicam, compared with piroxicam: Results of the safety and efficacy large-scale evaluation of COX-inhibiting therapies (SELECT) trial in osteoarthritis
    • Dequeker J., Hawkey C., et al. Improvement in gastrointestinal tolerability of the selective cyclooxygenase (COX)-2 inhibitor, meloxicam, compared with piroxicam: results of the safety and efficacy large-scale evaluation of COX-inhibiting therapies (SELECT) trial in osteoarthritis. Br. J. Rheumatol. 37:1998;946-951.
    • (1998) Br. J. Rheumatol. , vol.37 , pp. 946-951
    • Dequeker, J.1    Hawkey, C.2
  • 9
    • 0028860983 scopus 로고
    • Anti-inflammatory, analgesic, antipyretic and related properties of meloxicam, a new non-steroidal anti-inflammatory agent with favorable gastrointestinal tolerance
    • Engelhardt G., Homma D., Schlegel K., Utzmann R., Schnitzler C. Anti-inflammatory, analgesic, antipyretic and related properties of meloxicam, a new non-steroidal anti-inflammatory agent with favorable gastrointestinal tolerance. Inflamm. Res. 44:1995;423-433.
    • (1995) Inflamm. Res. , vol.44 , pp. 423-433
    • Engelhardt, G.1    Homma, D.2    Schlegel, K.3    Utzmann, R.4    Schnitzler, C.5
  • 11
    • 0002840747 scopus 로고
    • Synthesis of 9-fluorenylmethyloxycarbonyl-protected N-alkyl amino acids by reduction of oxazolidinones
    • Freindinger R.M., Hinkle J.S., Perlow D.S., Arison B.H. Synthesis of 9-fluorenylmethyloxycarbonyl-protected N-alkyl amino acids by reduction of oxazolidinones. J. Org. Chem. 48:1983;77-81.
    • (1983) J. Org. Chem. , vol.48 , pp. 77-81
    • Freindinger, R.M.1    Hinkle, J.S.2    Perlow, D.S.3    Arison, B.H.4
  • 12
    • 0035093929 scopus 로고    scopus 로고
    • Stereospecific synthesis of 2-alkyl-3-aryloxaziridines from prochiral and chiral N-arylidenealkylamines by use of the benzonitrile-hydrogen peroxide system
    • Kraïem J., Kacem Y., Khiari J., Ben Hassine B. Stereospecific synthesis of 2-alkyl-3-aryloxaziridines from prochiral and chiral N-arylidenealkylamines by use of the benzonitrile-hydrogen peroxide system. Synth. Commun. 31:2001;263-271.
    • (2001) Synth. Commun. , vol.31 , pp. 263-271
    • Kraïem, J.1    Kacem, Y.2    Khiari, J.3    Ben Hassine, B.4
  • 14
    • 0033071447 scopus 로고    scopus 로고
    • Synthesis and analgesic and anti-inflammatory activities of 1,2-benzothiazine derivatives
    • Lee E.B., Kwon S.K., Kim S.G. Synthesis and analgesic and anti-inflammatory activities of 1,2-benzothiazine derivatives. Arch. Pharm. Res. 22:1999;44-47.
    • (1999) Arch. Pharm. Res. , vol.22 , pp. 44-47
    • Lee, E.B.1    Kwon, S.K.2    Kim, S.G.3
  • 15
    • 0031859367 scopus 로고    scopus 로고
    • Gastrointestinal tolerability of meloxicam and piroxicam: A double-blind placebo-controlled study
    • Lipscomb G.R., Wallis N., Armstrong G., Rees W.D. Gastrointestinal tolerability of meloxicam and piroxicam: a double-blind placebo-controlled study. Br. J. Clin. Pharmacol. 46:1998;133-137.
    • (1998) Br. J. Clin. Pharmacol. , vol.46 , pp. 133-137
    • Lipscomb, G.R.1    Wallis, N.2    Armstrong, G.3    Rees, W.D.4
  • 16
    • 84951384024 scopus 로고
    • A simplified method of evaluating dose-effect experiments
    • Litchfield J.T., Wilcoxon F.A. A simplified method of evaluating dose-effect experiments. J. Pharmacol. Exp. Ther. 96:1949;99-113.
    • (1949) J. Pharmacol. Exp. Ther. , vol.96 , pp. 99-113
    • Litchfield, J.T.1    Wilcoxon, F.A.2
  • 17
    • 0015621734 scopus 로고
    • Potent anti-inflammatory N-heterocyclic 3-carboxamides of 4-hydroxy-2-methyl-2H-1,2-benzothiazine 1,1-dioxide
    • Lombardino J.G., Wiseman E.H., Chiaini J. Potent anti-inflammatory N-heterocyclic 3-carboxamides of 4-hydroxy-2-methyl-2H-1,2-benzothiazine 1,1-dioxide. J. Med. Chem. 16:1972;493-496.
    • (1972) J. Med. Chem. , vol.16 , pp. 493-496
    • Lombardino, J.G.1    Wiseman, E.H.2    Chiaini, J.3
  • 18
    • 0015708398 scopus 로고
    • The effect of E and A prostaglandin on gastric mucosal blood flow and acid secretion in the rat
    • Main I.H.M., Whittle B.J.R. The effect of E and A prostaglandin on gastric mucosal blood flow and acid secretion in the rat. Br. J. Pharmacol. 49:1973;428.
    • (1973) Br. J. Pharmacol. , vol.49 , pp. 428
    • Main, I.H.M.1    Whittle, B.J.R.2
  • 19
    • 0027005017 scopus 로고
    • Efficacy of non-steroidal anti-inflammatory drugs in the management of postoperative pain
    • Moote C. Efficacy of non-steroidal anti-inflammatory drugs in the management of postoperative pain. Drugs. 44:Suppl. 5 1992;14-30.
    • (1992) Drugs , vol.44 , Issue.SUPPL. 5 , pp. 14-30
    • Moote, C.1
  • 20
    • 0014136777 scopus 로고
    • Inhibition of gastric secretion by prostaglandins
    • Nezamin R.J.E., Philips J.P. Inhibition of gastric secretion by prostaglandins. Am. J. Digest. Dis. 12:1967;1073-1076.
    • (1967) Am. J. Digest. Dis. , vol.12 , pp. 1073-1076
    • Nezamin, R.J.E.1    Philips, J.P.2
  • 21
    • 0032885911 scopus 로고    scopus 로고
    • Rofecoxib
    • Scott L.J., Lamb H.M. Rofecoxib. Drugs. 58:1999;499-505.
    • (1999) Drugs , vol.58 , pp. 499-505
    • Scott, L.J.1    Lamb, H.M.2
  • 22
    • 0031680203 scopus 로고    scopus 로고
    • Preliminary study of the safety and efficacy of SC-58635, a novel cyclooxygenase-2 inhibitor
    • Simon L.S., et al. Preliminary study of the safety and efficacy of SC-58635, a novel cyclooxygenase-2 inhibitor. Arthritis Rheum. 41:1998;1591-1601.
    • (1998) Arthritis Rheum. , vol.41 , pp. 1591-1601
    • Simon, L.S.1
  • 23
    • 0012397313 scopus 로고
    • Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics
    • Snieckus V. Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics. Chem. Rev. 90:1990;879-933.
    • (1990) Chem. Rev. , vol.90 , pp. 879-933
    • Snieckus, V.1
  • 24
    • 0028926813 scopus 로고
    • New insights into the mode of action of anti-inflammatory drugs
    • Vane J.R., Botting R.M. New insights into the mode of action of anti-inflammatory drugs. Inflamm. Res. 44:1995;1-10.
    • (1995) Inflamm. Res. , vol.44 , pp. 1-10
    • Vane, J.R.1    Botting, R.M.2
  • 25
    • 0029928405 scopus 로고    scopus 로고
    • Mechanism of action of anti-inflammatory drugs
    • Vane J.R., Botting R.M. Mechanism of action of anti-inflammatory drugs. Scand. J. Rheumatol. 25:1996;9-25.
    • (1996) Scand. J. Rheumatol. , vol.25 , pp. 9-25
    • Vane, J.R.1    Botting, R.M.2
  • 28
    • 67249094291 scopus 로고
    • Carrageenan-induced oedema in hind paw of the rat as an assay for anti-inflammatory drugs
    • Winter C.A., Risley G.A., Nuss G.W. Carrageenan-induced oedema in hind paw of the rat as an assay for anti-inflammatory drugs. Proc. Soc. Exp. Biol. Med. 3:1962;544-547.
    • (1962) Proc. Soc. Exp. Biol. Med. , vol.3 , pp. 544-547
    • Winter, C.A.1    Risley, G.A.2    Nuss, G.W.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.