메뉴 건너뛰기




Volumn 42, Issue 7, 1999, Pages 1178-1192

Orally active isoxazoline glycoprotein IIb/IIIa antagonists with extended duration of action

Author keywords

[No Author keywords available]

Indexed keywords

3 [[3 [4 (AMINOIMINOMETHYL)PHENYL] 4,5 DIHYDRO 5 ISOXAZOLYL]ACETAMIDO] N [(3,5 DIMETHYL 4 ISOXAZOLYL)SULFONYL]ALANINE; FIBRINOGEN RECEPTOR ANTAGONIST; ISOXAZOLINE DERIVATIVE; ROXIFIBAN;

EID: 0033535522     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980348t     Document Type: Article
Times cited : (45)

References (49)
  • 1
    • 0027990555 scopus 로고
    • Pharmacology of current and future antithrombotic therapies
    • Muller, T. H.; Binder, K.; Guth, B. D. Pharmacology of Current and Future Antithrombotic Therapies. Cardiol. Clin. 1994, 12, 411-442.
    • (1994) Cardiol. Clin. , vol.12 , pp. 411-442
    • Muller, T.H.1    Binder, K.2    Guth, B.D.3
  • 2
    • 0029838529 scopus 로고    scopus 로고
    • Antiplatelet therapy
    • Schafer, A. I. Antiplatelet Therapy. Am. J. Med. 1996, 101, 199-209.
    • (1996) Am. J. Med. , vol.101 , pp. 199-209
    • Schafer, A.I.1
  • 4
    • 0024551590 scopus 로고
    • Platelet receptor recognition domain on alpha chain of human fibrinogen: Structure-function analysis
    • Hawiger, J.; Kloczewiak, M.; Bednarek, M.; Timmons, S. Platelet Receptor Recognition Domain on alpha Chain of Human Fibrinogen: Structure-Function Analysis. Biochemistry 1989, 28, 2909-2914.
    • (1989) Biochemistry , vol.28 , pp. 2909-2914
    • Hawiger, J.1    Kloczewiak, M.2    Bednarek, M.3    Timmons, S.4
  • 7
    • 77956773679 scopus 로고    scopus 로고
    • GPIIb/IIIa antagonists
    • Samanen, J. GPIIb/IIIa Antagonists. Annu. Rep. Med. Chem. 1996, 31, 91-100.
    • (1996) Annu. Rep. Med. Chem. , vol.31 , pp. 91-100
    • Samanen, J.1
  • 12
    • 0342872079 scopus 로고    scopus 로고
    • Profound and sustained inhibition of platelet aggregation by Fradafiban, a nonpeptide platelet glycoprotein IIb/IIIa antagonist, and its orally active prodrug, Lefradafiban
    • Muller, T. H.; Weisenberger, H.; Brickl, R.; Narjes, H.; Himmelsbach, F.; Krause, J. Profound and sustained inhibition of platelet aggregation by Fradafiban, a nonpeptide platelet glycoprotein IIb/IIIa antagonist, and its orally active prodrug, Lefradafiban. Circulation 1997, 96, 1130-1138.
    • (1997) Circulation , vol.96 , pp. 1130-1138
    • Muller, T.H.1    Weisenberger, H.2    Brickl, R.3    Narjes, H.4    Himmelsbach, F.5    Krause, J.6
  • 14
    • 0029879229 scopus 로고    scopus 로고
    • Platelet glycoprotein IIb/IIIa receptor antagonists in coronary artery disease
    • Lefkovits, J.; Topol, E. J. Platelet glycoprotein IIb/IIIa receptor antagonists in coronary artery disease. Eur. Heart J. 1996, 17, 9-18.
    • (1996) Eur. Heart J. , vol.17 , pp. 9-18
    • Lefkovits, J.1    Topol, E.J.2
  • 17
    • 0029853372 scopus 로고    scopus 로고
    • New thoughts on strategies for modulating platelet function through the inhibition of surface receptors
    • (b) Nurden, A. T. New Thoughts on Strategies for Modulating Platelet Function Through the Inhibition of Surface Receptors. Haemostasis 1996, 26 (Suppl. 4), 78-88.
    • (1996) Haemostasis , vol.26 , Issue.4 SUPPL. , pp. 78-88
    • Nurden, A.T.1
  • 18
    • 0030728315 scopus 로고    scopus 로고
    • Advances in antiplatelet therapy in coronary artery disease: Importance of the platelet GPIIb/IIIa receptor
    • (c) Timmis, G. C.; Khurana, S. Advances in Antiplatelet Therapy in Coronary Artery Disease: Importance of the Platelet GPIIb/IIIa Receptor. J. Intervent. Cardiol. 1997, 10, 327-333.
    • (1997) J. Intervent. Cardiol. , vol.10 , pp. 327-333
    • Timmis, G.C.1    Khurana, S.2
  • 19
    • 0030455738 scopus 로고    scopus 로고
    • Platelets in health and disease: Platelet GPIIb-IIIa structure and function: Recent advances in antiplatelet therapy
    • Mousa, S. A.; Bennett, J. A. Platelets in health and disease: platelet GPIIb-IIIa structure and function: recent advances in antiplatelet therapy. Drugs Future 1996, 21, 1141-1154.
    • (1996) Drugs Future , vol.21 , pp. 1141-1154
    • Mousa, S.A.1    Bennett, J.A.2
  • 23
    • 0011747059 scopus 로고    scopus 로고
    • Discovery of novel non-peptide antiplatelet GPIIb/IIIa receptor antagonist, DMP 754: Receptor binding affinity and specificity
    • (a) Mousa, S. A.; Bozarth, J.; Forsythe, M.; Xue, C.-B.; Wityak, J.; Olson, R.; Thoolen, M.; Reilly, T. Discovery of Novel Non-peptide Antiplatelet GPIIb/IIIa Receptor Antagonist, DMP 754: Receptor Binding Affinity and Specificity. Circulation 1996, 94, I-513, 3006.
    • (1996) Circulation , vol.94
    • Mousa, S.A.1    Bozarth, J.2    Forsythe, M.3    Xue, C.-B.4    Wityak, J.5    Olson, R.6    Thoolen, M.7    Reilly, T.8
  • 25
    • 0343933141 scopus 로고    scopus 로고
    • Discovery of novel non-peptide antiplatelet GPIIb/IIIa receptor antagonist, DMP 754: Comparitive platelet binding affinity profiles with DMP 728 and c7E3
    • Mousa, S. A.; Bozarth, J.; Forsythe, M.; Xue, C.-B.; Wityak, J.; Olson, R.; Thoolen, M.; Reilly, T. Discovery of Novel Non-peptide Antiplatelet GPIIb/IIIa Receptor Antagonist, DMP 754: Comparitive Platelet Binding Affinity Profiles with DMP 728 and c7E3. Thrombosis Hemostasis 1997, 2707 (Suppl.), 663.
    • (1997) Thrombosis Hemostasis , vol.2707 , Issue.SUPPL. , pp. 663
    • Mousa, S.A.1    Bozarth, J.2    Forsythe, M.3    Xue, C.-B.4    Wityak, J.5    Olson, R.6    Thoolen, M.7    Reilly, T.8
  • 26
    • 0030065819 scopus 로고    scopus 로고
    • Design, synthesis and in vitro activities of a series of benzimidazole/benzoxazole glycoprotein IIb/IIIa inhibitors
    • Xue, C.-B.; Rafalski, M.; Roderick, J.; Eyermann, C. J.; Mousa, S.; Olson, R. E.; DeGrado, W. F. Design, Synthesis and In Vitro Activities of a Series of Benzimidazole/Benzoxazole Glycoprotein IIb/IIIa Inhibitors. Bioorg. Med. Chem. Lett. 1996, 6, 339-344.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 339-344
    • Xue, C.-B.1    Rafalski, M.2    Roderick, J.3    Eyermann, C.J.4    Mousa, S.5    Olson, R.E.6    DeGrado, W.F.7
  • 27
    • 0030970551 scopus 로고    scopus 로고
    • Design, synthesis and in vitro activities of benzamide-core glycoprotein IIb/IIIa antagonists: 2,3-diaminopropionic acid derivatives as surrogates of aspartic acid
    • Xue, C.-B.; Roderick, J.; Jackson, S.; Rafalski, M.; Rockwell, A.; Mousa, S.; Olson, R. E.; DeGrado, W. F. Design, Synthesis and In Vitro Activities of Benzamide-Core Glycoprotein IIb/IIIa Antagonists: 2,3-Diaminopropionic Acid Derivatives as Surrogates of Aspartic Acid. Bioorg. Med. Chem. 1997, 5, 693-705.
    • (1997) Bioorg. Med. Chem. , vol.5 , pp. 693-705
    • Xue, C.-B.1    Roderick, J.2    Jackson, S.3    Rafalski, M.4    Rockwell, A.5    Mousa, S.6    Olson, R.E.7    DeGrado, W.F.8
  • 28
    • 0029938704 scopus 로고    scopus 로고
    • Non-peptide glycoprotein IIb/IIIa inhibitors. 9. Centrally constrained alpha-sulfonamides are useful tools for exploring platelet receptor function
    • Egbertson, M. S.; Bednar, B.; Bednar, R. A.; Hartman, G. D.; Gould, R. J.; Lynch, R. J.; Vassallo, L. M.; Young, S. D. Non-peptide Glycoprotein IIb/IIIa Inhibitors. 9. Centrally Constrained Alpha-Sulfonamides Are Useful Tools for Exploring Platelet Receptor Function. Bioorg. Med. Chem. Lett. 1996, 6, 1415-1420.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 1415-1420
    • Egbertson, M.S.1    Bednar, B.2    Bednar, R.A.3    Hartman, G.D.4    Gould, R.J.5    Lynch, R.J.6    Vassallo, L.M.7    Young, S.D.8
  • 33
    • 8244255012 scopus 로고    scopus 로고
    • Nonpeptide glycoprotein IIb/IIIa inhibitors. 15. Antithrombotic efficacy of L-738,167, a long-acting GPIIb/IIIa antagonist, correlates with inhibition of adenosine diphosphate-induced platelet aggregation but not with bleeding time prolongation
    • Cook, J. J.; Sitko, G. R.; Holahan, M. A.; Stranieri, M. T.; Glass, J. D.; Askew, B. C.; McIntyre, C. J.; Claremon, D. A.; Baldwin, J. J.; Hartman, G. D.; Gould, R. J.; Lynch, J. J., Jr. Nonpeptide Glycoprotein IIb/IIIa Inhibitors. 15. Antithrombotic Efficacy of L-738,167, a Long-Acting GPIIb/IIIa Antagonist, Correlates With Inhibition of Adenosine Diphosphate-Induced Platelet Aggregation But Not With Bleeding Time Prolongation. J. Pharmacol. Exp. Ther. 1997, 287, 677-689.
    • (1997) J. Pharmacol. Exp. Ther. , vol.287 , pp. 677-689
    • Cook, J.J.1    Sitko, G.R.2    Holahan, M.A.3    Stranieri, M.T.4    Glass, J.D.5    Askew, B.C.6    McIntyre, C.J.7    Claremon, D.A.8    Baldwin, J.J.9    Hartman, G.D.10    Gould, R.J.11    Lynch J.J., Jr.12
  • 34
    • 6844236353 scopus 로고    scopus 로고
    • Fibrinogen receptor (GPIIb-IIIa) antagonists derived from 5,6-bicyclic templates. Amidinoindoles, amidinoindazoles, and amidinobenzofurans containing the N-α-sulfonamide carboxylic acid function as potent platelet aggregation inhibitors
    • Su, T.; Naughton, M. A.; Smyth, M. S.; Rose, J. W.; Arfsten, A. E.; McCowan, J. R.; Jakubowski, J. A.; Wyss, V. L.; Ruterbories, K. J.; Sall, D. J.; Scarborough, R. M. Fibrinogen Receptor (GPIIb-IIIa) Antagonists Derived from 5,6-Bicyclic Templates. Amidinoindoles, Amidinoindazoles, and Amidinobenzofurans Containing the N-α-Sulfonamide Carboxylic Acid Function as Potent Platelet Aggregation Inhibitors. J. Med. Chem. 1997, 40, 4308-4318.
    • (1997) J. Med. Chem. , vol.40 , pp. 4308-4318
    • Su, T.1    Naughton, M.A.2    Smyth, M.S.3    Rose, J.W.4    Arfsten, A.E.5    McCowan, J.R.6    Jakubowski, J.A.7    Wyss, V.L.8    Ruterbories, K.J.9    Sall, D.J.10    Scarborough, R.M.11
  • 35
    • 33847797810 scopus 로고
    • Improved synthesis of sulfamoyl chlorides
    • Kloek, J. A.; Leschinsky, K. L. Improved synthesis of sulfamoyl chlorides. J. Org. Chem. 1976, 41, 4028-4029.
    • (1976) J. Org. Chem. , vol.41 , pp. 4028-4029
    • Kloek, J.A.1    Leschinsky, K.L.2
  • 36
    • 3242715546 scopus 로고
    • Preparation and properties of some N-substituted sulfamic acids
    • Audrieth, L. F.; Sveda, M. Preparation and properties of some N-substituted sulfamic acids. J. Org. Chem. 1944, 9, 89-101.
    • (1944) J. Org. Chem. , vol.9 , pp. 89-101
    • Audrieth, L.F.1    Sveda, M.2
  • 37
    • 0344643825 scopus 로고    scopus 로고
    • note
    • The isoxazolinylacetamides 12-45 of the present study are designated "a" when racemic at the isoxazoline C5 center and (S) at the diaminopropionate (DAP) center; the (A)-C5,(S)-DAP isomere "b"; the (S)-C5,(S)-DAP isomers "c"; the (R)-C5,(R)-DAP isomers "d"; and the (S)-C5,(A)-DAP isomers "e".
  • 38
    • 0019521001 scopus 로고
    • Potential inhibitors of asparagine biosynthesis. 5. Electrophilic amide analogues of (S)-2,3-diaminopropionic acid
    • Mokotoff, M.; Logue, L. W. Potential inhibitors of asparagine biosynthesis. 5. electrophilic amide analogues of (S)-2,3-diaminopropionic acid. J. Med. Chem. 1981, 24, 554-559.
    • (1981) J. Med. Chem. , vol.24 , pp. 554-559
    • Mokotoff, M.1    Logue, L.W.2
  • 40
    • 0030917144 scopus 로고    scopus 로고
    • Flow cytometric measurement of kinetic and equilibrium binding parameters of arginine-glycine-aspartic acid ligands in binding to glycoprotein IIb/IIIa on platelets
    • Bednar, B.; Cunningham, M. E.; McQueney, P. A.; Egbertson, M. S.; Askew, B. C.; Bednar, R. A.; Hartman, G. D.; Gould, R. J. Flow Cytometric Measurement of Kinetic and Equilibrium Binding Parameters of Arginine-Glycine-Aspartic Acid Ligands in Binding to Glycoprotein IIb/IIIa on Platelets. Cytometry 1997, 28, 58-65.
    • (1997) Cytometry , vol.28 , pp. 58-65
    • Bednar, B.1    Cunningham, M.E.2    McQueney, P.A.3    Egbertson, M.S.4    Askew, B.C.5    Bednar, R.A.6    Hartman, G.D.7    Gould, R.J.8
  • 41
    • 0030997245 scopus 로고    scopus 로고
    • Disposition of L-738,167, a potent and long acting fibrinogen receptor antagonist in dogs: Dose-dependent pharmacokinetics
    • Prueksaritanont, T.; Gorham, L. M.; Naue, J. A.; Hamill, T. G.; Askew, B. C.; Vyas, K. P. Disposition of L-738,167, A Potent and Long Acting Fibrinogen Receptor Antagonist in Dogs: Dose-dependent Pharmacokinetics. Drug Metab. Dispos. 1997, 25, 355-361.
    • (1997) Drug Metab. Dispos. , vol.25 , pp. 355-361
    • Prueksaritanont, T.1    Gorham, L.M.2    Naue, J.A.3    Hamill, T.G.4    Askew, B.C.5    Vyas, K.P.6
  • 43
    • 0023757437 scopus 로고
    • Angiotensin-converting enzyme inhibitors. Relationship between pharmacodynamics and pharmacokinetics
    • Belz, G. G.; Kirch, W.; Kleinbloesem, C. H. Angiotensin-Converting Enzyme Inhibitors. Relationship Between Pharmacodynamics and Pharmacokinetics. Clin. Pharmacokinet. 1988, 15, 295-318.
    • (1988) Clin. Pharmacokinet , vol.15 , pp. 295-318
    • Belz, G.G.1    Kirch, W.2    Kleinbloesem, C.H.3
  • 44
    • 0023408263 scopus 로고
    • Relationships between CSF drug concentrations, receptor binding characteristics, and pharmacokinetic and pharmacodynamic properties of selected 1,4-substituted benzodiazepines
    • Colburn, W. A.; Jack, M. L. Relationships Between CSF Drug Concentrations, Receptor Binding Characteristics, and Pharmacokinetic and Pharmacodynamic Properties of Selected 1,4-Substituted Benzodiazepines. Clin. Pharmacokinet. 1987, 13, 179-190.
    • (1987) Clin. Pharmacokinet. , vol.13 , pp. 179-190
    • Colburn, W.A.1    Jack, M.L.2
  • 45
    • 4244125838 scopus 로고    scopus 로고
    • XV454, a novel non-peptide antiplatelet agent with comparable platelet alphaIIb beta3 binding kinetics to c7E3 and long lasting antiplatelet efficacy after single intravenous or oral administration in nonhuman primates
    • Mousa, S.; Forsythe, M.; Bozarth, J.; Youssef, A.; Wityak, J.; Olson, R.; Sielecki, T. XV454, A novel non-peptide antiplatelet agent with comparable platelet alphaIIb beta3 binding kinetics to c7E3 and long lasting antiplatelet efficacy after single intravenous or oral administration in nonhuman primates. Circulation 1997, 96, I-168, 928.
    • (1997) Circulation , vol.96
    • Mousa, S.1    Forsythe, M.2    Bozarth, J.3    Youssef, A.4    Wityak, J.5    Olson, R.6    Sielecki, T.7
  • 48
    • 0019521001 scopus 로고
    • Potential inhibitors of L-asparagine biosynthesis. 5. Electrophilic amide analogues of (S)-2,3-diaminopropionic
    • Mokotoff, M.; Logue, L. W. Potential Inhibitors of L-Asparagine Biosynthesis. 5. Electrophilic Amide Analogues of (S)-2,3-Diaminopropionic Acid. J. Med. Chem. 1981, 24, 554-559.
    • (1981) Acid. J. Med. Chem. , vol.24 , pp. 554-559
    • Mokotoff, M.1    Logue, L.W.2
  • 49
    • 0015339599 scopus 로고
    • Sulfamoyl azides, hydrolysis rates and hypotensive activity
    • Matier, W. L.; Comer, W. T.; Deitchman, D. Sulfamoyl azides, Hydrolysis rates and hypotensive activity. J. Med. Chem. 1972, 15, 538-541.
    • (1972) J. Med. Chem. , vol.15 , pp. 538-541
    • Matier, W.L.1    Comer, W.T.2    Deitchman, D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.