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Volumn 45, Issue 20, 2002, Pages 4419-4432

Unique overlap in the prerequisites for thrombin inhibition and oral bioavailability resulting in potent oral antithrombotics

Author keywords

[No Author keywords available]

Indexed keywords

LISINOPRIL; THROMBIN; THROMBIN INHIBITOR;

EID: 0037179611     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm011110z     Document Type: Article
Times cited : (32)

References (50)
  • 1
    • 0032060853 scopus 로고    scopus 로고
    • Angiotensin II AT1 receptor antagonists: Clinical development and future perspectives
    • Burnier, M.; Brunner, H. R. Angiotensin II AT1 receptor antagonists: clinical development and future perspectives. Therapie 1998, 53, 279-284.
    • (1998) Therapie , vol.53 , pp. 279-284
    • Burnier, M.1    Brunner, H.R.2
  • 2
    • 0033178872 scopus 로고    scopus 로고
    • Nonpeptide ligands for peptide and protein receptors
    • Freidinger, R. M. Nonpeptide ligands for peptide and protein receptors. Curr. Opin. Chem. Biol. 1999, 3, 395-406.
    • (1999) Curr. Opin. Chem. Biol. , vol.3 , pp. 395-406
    • Freidinger, R.M.1
  • 3
    • 0033052520 scopus 로고    scopus 로고
    • Recent advances in the chemistry of cholecystokinin receptor ligands (agonists and antagonists)
    • De Tullio, P.; Delarge, J.; Pirotte, B. Recent advances in the chemistry of cholecystokinin receptor ligands (agonists and antagonists). Curr. Med. Chem. 1999, 6, 433-455.
    • (1999) Curr. Med. Chem. , vol.6 , pp. 433-455
    • De Tullio, P.1    Delarge, J.2    Pirotte, B.3
  • 4
    • 0034069082 scopus 로고    scopus 로고
    • Vasopressin receptor antagonism-a therapeutic option in heart failure and hypertension
    • Burrell, L. M.; Risvanis, J.; Johnston, C. I.; Naitoh, M.; Balding, L. C. Vasopressin receptor antagonism-a therapeutic option in heart failure and hypertension. Exp. Physiol. 2000, 85, 259S-265S.
    • (2000) Exp. Physiol. , vol.85
    • Burrell, L.M.1    Risvanis, J.2    Johnston, C.I.3    Naitoh, M.4    Balding, L.C.5
  • 5
    • 0032699523 scopus 로고    scopus 로고
    • Corticotropin-releasing factor antagonists in affective disorders
    • Owens, M. J.; Nemeroff, C. B. Corticotropin-releasing factor antagonists in affective disorders. Exp. Opin. Invest. Drugs 1999, 8, 1849-1858.
    • (1999) Exp. Opin. Invest. Drugs , vol.8 , pp. 1849-1858
    • Owens, M.J.1    Nemeroff, C.B.2
  • 6
    • 0029040711 scopus 로고
    • Non-peptide inhibitors of human leukocyte elastase. 4. Design, synthesis, and in vitro and in vivo activity of a series of beta-carbolinone-containing trifluoromethyl ketones
    • Veale, C. A.; Damewood, J. R., Jr.; Steelman, G. B.; Bryant, C.; Gomes, B.; Williams, J. Non-peptide inhibitors of human leukocyte elastase. 4. Design, synthesis, and in vitro and in vivo activity of a series of beta-carbolinone-containing trifluoromethyl ketones. J. Med. Chem. 1995, 38, 86-97.
    • (1995) J. Med. Chem. , vol.38 , pp. 86-97
    • Veale, C.A.1    Damewood J.R., Jr.2    Steelman, G.B.3    Bryant, C.4    Gomes, B.5    Williams, J.6
  • 7
    • 0024578332 scopus 로고
    • Renin inhibitors: Specific modulators of the renin-angiotensin system
    • Luther, R. R.; Stein, H. H.; Glassman, H. N.; Kleinert, H. D. Renin inhibitors: specific modulators of the renin-angiotensin system. Arzneim.-Forsch. 1989, 39, 1-5.
    • (1989) Arzneim.-Forsch. , vol.39 , pp. 1-5
    • Luther, R.R.1    Stein, H.H.2    Glassman, H.N.3    Kleinert, H.D.4
  • 8
    • 0031729333 scopus 로고    scopus 로고
    • New antithrombotic agents
    • Weitz, J. I.; Hirsh, J. New antithrombotic agents. Chest 1998, 114, 715S-727S.
    • (1998) Chest , vol.114
    • Weitz, J.I.1    Hirsh, J.2
  • 9
    • 0032505039 scopus 로고    scopus 로고
    • Clinical potential of antithrombotic drugs in coronary syndromes
    • Turpie, A. G. Clinical potential of antithrombotic drugs in coronary syndromes. Am. J. Cardiol. 1998, 82, 11L-14L.
    • (1998) Am. J. Cardiol. , vol.82
    • Turpie, A.G.1
  • 10
    • 0030693694 scopus 로고    scopus 로고
    • Small-molecule direct thrombin inhibitors
    • Wiley, M.; Fisher, M. J. Small-molecule direct thrombin inhibitors. Exp. Opin. Ther. Pat. 1997, 7, 1265-1282.
    • (1997) Exp. Opin. Ther. Pat. , vol.7 , pp. 1265-1282
    • Wiley, M.1    Fisher, M.J.2
  • 11
    • 0033378391 scopus 로고    scopus 로고
    • Strategies and progress towards the ideal orally active thrombin inhibitor
    • Rewinkel, J. B. M.; Adang, A. E. P. Strategies and progress towards the ideal orally active thrombin inhibitor. Curr. Pharm. Des. 1999, 5, 1043-1075.
    • (1999) Curr. Pharm. Des. , vol.5 , pp. 1043-1075
    • Rewinkel, J.B.M.1    Adang, A.E.P.2
  • 12
    • 0034126830 scopus 로고    scopus 로고
    • A new generation of orally active antithrombotics: Comparing strategies in the GPIIb/IIIa, thrombin and factor Xa areas
    • Adang, A. E. P.; Rewinkel, J. B. M. A new generation of orally active antithrombotics: comparing strategies in the GPIIb/IIIa, thrombin and factor Xa areas. Drugs Future 2000, 25, 369-383.
    • (2000) Drugs Future , vol.25 , pp. 369-383
    • Adang, A.E.P.1    Rewinkel, J.B.M.2
  • 14
    • 0033535401 scopus 로고    scopus 로고
    • 1-Aminoisoquinoline as benzamidine isoster in the design and synthesis of orally active thrombin inhibitors
    • Rewinkel, J. B. M.; Lucas, H.; van Galen, P. J. M. 1-Aminoisoquinoline as benzamidine isoster in the design and synthesis of orally active thrombin inhibitors. Bioorg. Med. Chem. Lett. 1999, 9, 685-690.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 685-690
    • Rewinkel, J.B.M.1    Lucas, H.2    Van Galen, P.J.M.3
  • 15
    • 0033519182 scopus 로고    scopus 로고
    • Solution-phase and solid-phase synthesis of novel transition state inhibitors of coagulation enzymes incorporating a piperidinyl moiety
    • Adang, A. E. P.; Peters, C. A. M.; Gerritsma, S.; de Zwart, E.; Veeneman, G. Solution-phase and solid-phase synthesis of novel transition state inhibitors of coagulation enzymes incorporating a piperidinyl moiety. Bioorg. Med. Chem. Lett. 1999, 9, 1227-1232.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 1227-1232
    • Adang, A.E.P.1    Peters, C.A.M.2    Gerritsma, S.3    De Zwart, E.4    Veeneman, G.5
  • 18
    • 0025328906 scopus 로고
    • Highly active and selective anticoagulants: D-Phe-Pro-Arg-H, a free tripeptide aldehyde prone to spontaneous inactivation, and its stable N-methyl derivative, D.-MePhe-Pro-Arg-H
    • Bajusz, S.; Szell, E.; Bagdy, D.; Barabas, E.; Horvath, G.; Dioszegi, M.; Fittler, Z.; Szabo, G.; Juhasz, A. Highly active and selective anticoagulants: D-Phe-Pro-Arg-H, a free tripeptide aldehyde prone to spontaneous inactivation, and its stable N-methyl derivative, D.-MePhe-Pro-Arg-H. J. Med. Chem. 1990, 33, 1729-1735.
    • (1990) J. Med. Chem. , vol.33 , pp. 1729-1735
    • Bajusz, S.1    Szell, E.2    Bagdy, D.3    Barabas, E.4    Horvath, G.5    Dioszegi, M.6    Fittler, Z.7    Szabo, G.8    Juhasz, A.9
  • 20
    • 0027167091 scopus 로고
    • Inhibition of thrombin and other trypsin-like serine proteinases by cyclotheonamide A
    • Lewis, S. D.; Ng, A. S.; Baldwin, J. J.; Fusetani, N.; Naylor, A. M.; Shafer, J. A. Inhibition of thrombin and other trypsin-like serine proteinases by cyclotheonamide A. Thromb. Res. 1991, 70, 173-190.
    • (1991) Thromb. Res. , vol.70 , pp. 173-190
    • Lewis, S.D.1    Ng, A.S.2    Baldwin, J.J.3    Fusetani, N.4    Naylor, A.M.5    Shafer, J.A.6
  • 22
    • 0028834594 scopus 로고
    • Chelation- and nonchelation-controlled addition of 2-(trimethylsilyl)thiazole to α-amino aldehydes: Stereoselective synthesis of the β-amino-α-hydroxy aldehyde intermediate for the preparation of the human immunodeficiency virus proteinase inhibitor Ro 31-8959
    • Dondoni, A.; Perrone, D.; Merino, P. Chelation- and nonchelation-controlled addition of 2-(trimethylsilyl)thiazole to α-amino aldehydes: stereoselective synthesis of the β-amino-α-hydroxy aldehyde intermediate for the preparation of the human immunodeficiency virus proteinase inhibitor Ro 31-8959. J. Org. Chem. 1995, 60, 8074-8080.
    • (1995) J. Org. Chem. , vol.60 , pp. 8074-8080
    • Dondoni, A.1    Perrone, D.2    Merino, P.3
  • 23
    • 27844466269 scopus 로고
    • N-methoxy-N-methylamides as effective acylating agents
    • Nahm, S.; Weinreb, S. M. N-methoxy-N-methylamides as effective acylating agents. Tetrahedron Lett. 1981, 22, 3815-3818.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3815-3818
    • Nahm, S.1    Weinreb, S.M.2
  • 24
    • 0000884941 scopus 로고
    • Imidates including cyclic imidates
    • Patai, S., Ed.; John Wiley & Sons: New York
    • Nielsen, D. G. Imidates including cyclic imidates. In The Chemistry of Amidines and Imidates; Patai, S., Ed.; John Wiley & Sons: New York, 1975; Vol. I, pp 385-489.
    • (1975) The Chemistry of Amidines and Imidates , vol.1 , pp. 385-489
    • Nielsen, D.G.1
  • 25
    • 33644528891 scopus 로고
    • 125I oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones
    • 125I oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J. Org. Chem. 1983, 48, 4155-4156.
    • (1983) J. Org. Chem. , vol.48 , pp. 4155-4156
    • Dess, D.B.1    Martin, J.C.2
  • 28
    • 0022342897 scopus 로고
    • Pharmacological characterization of a new highly effective synthetic thrombin inhibitor
    • Kaiser, B.; Hauptmann, J.; Weiss, A.; Markwardt, F. Pharmacological characterization of a new highly effective synthetic thrombin inhibitor. Biomed. Biochim. Acta 1985, 44, 1201-1210.
    • (1985) Biomed. Biochim. Acta , vol.44 , pp. 1201-1210
    • Kaiser, B.1    Hauptmann, J.2    Weiss, A.3    Markwardt, F.4
  • 35
    • 0033594506 scopus 로고    scopus 로고
    • Secondary structure peptide mimetics: Design, synthesis, and evaluation of β-strand mimetic thrombin inhibitors
    • Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, B. C.; Shea, J. P.; Kahn, M. Secondary structure peptide mimetics: Design, synthesis, and evaluation of β-strand mimetic thrombin inhibitors. J. Med. Chem. 1999, 42, 1367-1375.
    • (1999) J. Med. Chem. , vol.42 , pp. 1367-1375
    • Boatman, P.D.1    Ogbu, C.O.2    Eguchi, M.3    Kim, H.-O.4    Nakanishi, B.C.5    Shea, J.P.6    Kahn, M.7
  • 37
    • 0033526063 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationship of potent bicyclic lactam thrombin inhibitors
    • Bachand, B.; DiMaio, J.; Siddiqui, M. A. Synthesis and structure-activity relationship of potent bicyclic lactam thrombin inhibitors. Bioorg. Med. Chem. Lett. 1999, 9, 913-918.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 913-918
    • Bachand, B.1    DiMaio, J.2    Siddiqui, M.A.3
  • 38
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Delivery Rev. 1997, 23, 3-25.
    • (1997) Adv. Drug Delivery Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 39
    • 0033801280 scopus 로고    scopus 로고
    • Membrane transporters
    • Lee, V. H. L. Membrane transporters. J. Pharm. Sci. 2000, 11, S41-S50.
    • (2000) J. Pharm. Sci. , vol.11
    • Lee, V.H.L.1
  • 40
    • 0026452062 scopus 로고
    • Relative lipophilicities and structural-pharmacological considerations of various angiotensin-converting enzmyme (ACE) inhibitors
    • Ranadive, S. A.; Chen, A. X.; Serajuddin, A. T. M. Relative lipophilicities and structural-pharmacological considerations of various angiotensin-converting enzmyme (ACE) inhibitors. Pharm. Res. 1992, 9, 1480-1486.
    • (1992) Pharm. Res. , vol.9 , pp. 1480-1486
    • Ranadive, S.A.1    Chen, A.X.2    Serajuddin, A.T.M.3
  • 41
    • 0028905095 scopus 로고
    • Angiotensin-converting enzyme (ACE) inhibitor transport in human intestinal epithelial (Caco-2) cells
    • Thwaites, D. T.; Cavet, M.; Hirst, B. H.; Simmons, N. L. Angiotensin-converting enzyme (ACE) inhibitor transport in human intestinal epithelial (Caco-2) cells. Br. J. Pharmacol. 1995, 114, 981-986.
    • (1995) Br. J. Pharmacol. , vol.114 , pp. 981-986
    • Thwaites, D.T.1    Cavet, M.2    Hirst, B.H.3    Simmons, N.L.4
  • 43
    • 0029025244 scopus 로고
    • Peptidyl a-ketoheterocyclic inhibitors of human neutrophil eleastase. 2. Effect of varying the heterocyclic ring on in vitro potency
    • Edwards, P. D.; Wolanin, D. J.; Andisik, D. W.; Davis, M. W. Peptidyl a-ketoheterocyclic inhibitors of human neutrophil eleastase. 2. Effect of varying the heterocyclic ring on in vitro potency. J. Med. Chem. 1995, 38, 76-85.
    • (1995) J. Med. Chem. , vol.38 , pp. 76-85
    • Edwards, P.D.1    Wolanin, D.J.2    Andisik, D.W.3    Davis, M.W.4
  • 44
    • 0029561302 scopus 로고
    • Transport of peptidomimetic renin inhibitors across monolayers of a human intestinal cell line (Caco-2): Evidence for self-enhancement of paracellular transport route
    • Walter, E.; Kissel, T.; Raddatz, P. Transport of peptidomimetic renin inhibitors across monolayers of a human intestinal cell line (Caco-2): evidence for self-enhancement of paracellular transport route. Pharm. Res. 1995, 12, 1801-1805.
    • (1995) Pharm. Res. , vol.12 , pp. 1801-1805
    • Walter, E.1    Kissel, T.2    Raddatz, P.3
  • 45
    • 0017362472 scopus 로고
    • Evaluation of an amidolytic heparin assay method: Increased sensitivity by adding purified antithrombin III
    • Teien, A. N.; Lie, M. Evaluation of an amidolytic heparin assay method: increased sensitivity by adding purified antithrombin III. Thromb. Res. 1977, 10, 399-410.
    • (1977) Thromb. Res. , vol.10 , pp. 399-410
    • Teien, A.N.1    Lie, M.2
  • 48
    • 0033081529 scopus 로고    scopus 로고
    • Rapid automated molecular replacement by evolutionary search
    • Kissinger, C. R.; Gehlhaar, D. K.; Fogel, D. B. Rapid automated molecular replacement by evolutionary search. Acta Crystallogr. D 1999, 55, 484-491.
    • (1999) Acta Crystallogr. D , vol.55 , pp. 484-491
    • Kissinger, C.R.1    Gehlhaar, D.K.2    Fogel, D.B.3
  • 49
    • 0026347092 scopus 로고
    • Argatroban, a selective, potent thrombin inhibitor
    • Bush, L. R. Argatroban, a selective, potent thrombin inhibitor. Cardiovasc. Drug Rev. 1991, 9, 247-263.
    • (1991) Cardiovasc. Drug Rev. , vol.9 , pp. 247-263
    • Bush, L.R.1


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