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Volumn 42, Issue 2, 1999, Pages 305-311

Vasopeptidase inhibitors: Incorporation of geminal and spirocyclic substituted azepinones in mercaptoacyl dipeptides

Author keywords

[No Author keywords available]

Indexed keywords

ANTIHYPERTENSIVE AGENT; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; HEXAHYDRO 6 [(2 MERCAPTO 1 OXO 3 PHENYLPROPYL)AMINO] 2,2 DIMETHYL 7 OXO 1H AZEPINE 1 ACETIC ACID; MEMBRANE METALLOENDOPEPTIDASE; METALLOPROTEINASE INHIBITOR; OMAPATRILAT; UNCLASSIFIED DRUG;

EID: 0032906160     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980542f     Document Type: Article
Times cited : (42)

References (26)
  • 1
    • 0344212055 scopus 로고    scopus 로고
    • Cardiac inhibition of angiotensin converting enzyme: Role of kinins
    • (a) Linz, W.; Wiemer, G.; Scholkens, B. A. Cardiac inhibition of angiotensin converting enzyme: role of kinins. Endothelial Cell Res. Ser. 1998, 2, 223-235.
    • (1998) Endothelial Cell Res. Ser. , vol.2 , pp. 223-235
    • Linz, W.1    Wiemer, G.2    Scholkens, B.A.3
  • 2
    • 0031958949 scopus 로고    scopus 로고
    • Role of bradykinin in the reduction of left ventricular hypertrophy induced by angiotensin-converting enzyme inhibitors in spontaneously hypertensive rats
    • (b) Sugimoto, K.; Fujimura, A. Role of bradykinin in the reduction of left ventricular hypertrophy induced by angiotensin-converting enzyme inhibitors in spontaneously hypertensive rats. Jpn. J. Pharmacol. 1998, 76, 431-434.
    • (1998) Jpn. J. Pharmacol. , vol.76 , pp. 431-434
    • Sugimoto, K.1    Fujimura, A.2
  • 3
    • 0031029540 scopus 로고    scopus 로고
    • Effect of neutral endopeptidase 24.11 inhibition on myocardial ischemia/reperfusion injury: The role of kinins
    • (c) Yang, X.-P.; Liu, Y.-H.; Peterson, E.; Carretero, O. A. Effect of neutral endopeptidase 24.11 inhibition on myocardial ischemia/reperfusion injury: the role of kinins. J. Cardiovasc. Pharmacol. 1997, 29, 250-256.
    • (1997) J. Cardiovasc. Pharmacol. , vol.29 , pp. 250-256
    • Yang, X.-P.1    Liu, Y.-H.2    Peterson, E.3    Carretero, O.A.4
  • 4
    • 0026730011 scopus 로고
    • Bradykinin-mediated effects of ACE inhibition
    • (d) Gavras, I. Bradykinin-mediated effects of ACE inhibition. Kidney Int. 1992, 42, 1020-1029.
    • (1992) Kidney Int. , vol.42 , pp. 1020-1029
    • Gavras, I.1
  • 5
    • 0002904225 scopus 로고    scopus 로고
    • Neutral endopeptidase inhibitors and combined inhibitors of neutral endopepti-dase and angiotensin-converting enzyme
    • Van Zwieten, P. A., Greenlee, W. J., Eds.; Harwood Academic Publishers: Amsterdam
    • (a) Robl, J. A.; Trippodo, N. C.; Petrillo, E. W. Neutral endopeptidase inhibitors and combined inhibitors of neutral endopepti-dase and angiotensin-converting enzyme. In Antihypertensive Drugs; Van Zwieten, P. A., Greenlee, W. J., Eds.; Harwood Academic Publishers: Amsterdam, 1997; pp 113-212.
    • (1997) Antihypertensive Drugs , pp. 113-212
    • Robl, J.A.1    Trippodo, N.C.2    Petrillo, E.W.3
  • 6
    • 0006826135 scopus 로고    scopus 로고
    • Design and pharmacology of dual angiotensin-converting enzyme and neutral endopeptidase inhibitors
    • (b) De Lombaert, S.; Chatelain, R. E.; Fink, C. E.; Trapani, A. J. Design and pharmacology of dual angiotensin-converting enzyme and neutral endopeptidase inhibitors. Curr. Pharm. Des. 1996, 2, 443-462.
    • (1996) Curr. Pharm. Des. , vol.2 , pp. 443-462
    • De Lombaert, S.1    Chatelain, R.E.2    Fink, C.E.3    Trapani, A.J.4
  • 7
    • 0029809157 scopus 로고    scopus 로고
    • Recent advances in the development of dual angiotensin-converting enzyme and neutral endopeptidase inhibitors
    • (c) Fink, C. A. Recent advances in the development of dual angiotensin-converting enzyme and neutral endopeptidase inhibitors. Exp. Opin. Ther. Patents 1996, 6, 1147-1164.
    • (1996) Exp. Opin. Ther. Patents , vol.6 , pp. 1147-1164
    • Fink, C.A.1
  • 8
    • 0002987505 scopus 로고
    • Dual inhibitors of angiotensin-converting enzyme and neutral endopeptidase: Design and therapeutic rationale
    • Laragh, J. H., Brenner, B. M., Eds.; Raven Press Ltd.: New York
    • (d) Flynn, G. A.; French, J. F.; Dage, R. C. Dual inhibitors of angiotensin-converting enzyme and neutral endopeptidase: design and therapeutic rationale. In Hypertension: Pathophysiology, Diagnosis, and Management, 2nd ed.; Laragh, J. H., Brenner, B. M., Eds.; Raven Press Ltd.: New York, 1995; pp 3099-3114.
    • (1995) Hypertension: Pathophysiology, Diagnosis, and Management, 2nd Ed. , pp. 3099-3114
    • Flynn, G.A.1    French, J.F.2    Dage, R.C.3
  • 11
    • 0000326308 scopus 로고    scopus 로고
    • Supine mean arterial blood pressure (MAP) lowering and oral tolerance of BMS-186716, a new dual metalloprotease inhibitor of angiotensin-converting enzyme (ACE) and neutral endopeptidase (NEP), in healthy male subjects
    • (a) Liao, W.; Delaney, C.; Smith, R.; Lubin, S.; McNulty, S.; Davis, K.; Meier, A.; Uderman, H. Supine mean arterial blood pressure (MAP) lowering and oral tolerance of BMS-186716, a new dual metalloprotease inhibitor of angiotensin-converting enzyme (ACE) and neutral endopeptidase (NEP), in healthy male subjects (abst.). Clin. Pharmacol. Ther. 1997, 61, 229.
    • (1997) Clin. Pharmacol. Ther. , vol.61 , pp. 229
    • Liao, W.1    Delaney, C.2    Smith, R.3    Lubin, S.4    McNulty, S.5    Davis, K.6    Meier, A.7    Uderman, H.8
  • 12
    • 0001643315 scopus 로고    scopus 로고
    • Effects of BMS-186716, a new dual metalloprotease inhibitor, on pharmacodynamic markers of neutral endopeptidase (NEP) and angiotensin-converting enzyme (ACE), in healthy male subjects
    • (b) Vesterqvist, O.; Liao, W.; Manning, J. A.; Uderman, H.; Delaney. C.; Beierle, F.; Swanson, B. N. Effects of BMS-186716, a new dual metalloprotease inhibitor, on pharmacodynamic markers of neutral endopeptidase (NEP) and angiotensin-converting enzyme (ACE), in healthy male subjects (abst.). Clin. Pharmacol. Ther. 1997, 61, 230.
    • (1997) Clin. Pharmacol. Ther. , vol.61 , pp. 230
    • Vesterqvist, O.1    Liao, W.2    Manning, J.A.3    Uderman, H.4    Delaney, C.5    Beierle, F.6    Swanson, B.N.7
  • 18
    • 0028925678 scopus 로고
    • Dual metalloprotease inhibitors. V. Utilization of bicyclic azepinonethiazolidines and azepinonetetrahydrothiazines in constrained peptidomimetics of mercaptoacyl dipeptides
    • (f) Slusarchyk, W. A.; Robl, J. A.; Taunk, P. C.; Asaad, M. M.; Bird, J. E.; DiMarco, P. Y. Dual metalloprotease inhibitors. V. utilization of bicyclic azepinonethiazolidines and azepinonetetrahydrothiazines in constrained peptidomimetics of mercaptoacyl dipeptides. BioMed. Chem. Lett. 1995, 5, 753-758.
    • (1995) BioMed. Chem. Lett. , vol.5 , pp. 753-758
    • Slusarchyk, W.A.1    Robl, J.A.2    Taunk, P.C.3    Asaad, M.M.4    Bird, J.E.5    DiMarco, P.Y.6
  • 19
    • 0030032034 scopus 로고    scopus 로고
    • Dual metalloprotease inhibitors 6. Incorporation of bicyclic and substituted monocyclic azepinones as dipeptide surrogates in angiotensin-converting enzyme/neutral endopeptidase inhibitors
    • Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Brown, B. B.; Ryono, D. E.; Bird, J. E.; Asaad, M. M.; Schaeffer, T. R.; Trippodo, N. C. Dual metalloprotease inhibitors 6. Incorporation of bicyclic and substituted monocyclic azepinones as dipeptide surrogates in angiotensin-converting enzyme/neutral endopeptidase inhibitors. J. Med. Chem. 1996, 39, 494-502.
    • (1996) J. Med. Chem. , vol.39 , pp. 494-502
    • Robl, J.A.1    Cimarusti, M.P.2    Simpkins, L.M.3    Brown, B.B.4    Ryono, D.E.5    Bird, J.E.6    Asaad, M.M.7    Schaeffer, T.R.8    Trippodo, N.C.9
  • 20
    • 0030577486 scopus 로고    scopus 로고
    • Synthetic routes for the generation of 7,7-dialkyl azepin-2-ones
    • Robl, J. A.; Sieber-McMaster, E.; Sulsky, R. Synthetic routes for the generation of 7,7-dialkyl azepin-2-ones. Tetrahedron Lett. 1996, 37, 8985-8988.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8985-8988
    • Robl, J.A.1    Sieber-McMaster, E.2    Sulsky, R.3
  • 21
    • 0345074309 scopus 로고    scopus 로고
    • 3Al in toluene solution failed to give the desired adduct cleanly
    • 3Al in toluene solution failed to give the desired adduct cleanly.
  • 22
    • 0001396585 scopus 로고
    • 4: A nonbasic and highly selective Grignard analogue
    • 4: A nonbasic and highly selective Grignard analogue. Tetrahedron 1986, 42, 2931-2935. We also found it convenient to perform this reaction using dichloromethane as solvent which usually affords better reaction homogeneity.
    • (1986) Tetrahedron , vol.42 , pp. 2931-2935
    • Reetz, M.T.1    Kyung, S.H.2    Hullmann, M.3
  • 23
    • 0001164135 scopus 로고
    • Iminophosphorane-mediated transformation of tertiary alcohols into tert-alkylamines and their N-phosphorylated derivatives
    • Koziara, A.; Zwierzak, A. Iminophosphorane-mediated transformation of tertiary alcohols into tert-alkylamines and their N-phosphorylated derivatives. Tetrahedron Lett. 1987, 28, 6513-6516.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6513-6516
    • Koziara, A.1    Zwierzak, A.2
  • 24
    • 0028215536 scopus 로고
    • A synthetic route for the generation of C-7 substituted azepinones
    • Robl, J. A.; Cimarusti, M. P. A synthetic route for the generation of C-7 substituted azepinones. Tetrahedron Lett. 1994, 35, 1393-1396.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 1393-1396
    • Robl, J.A.1    Cimarusti, M.P.2
  • 25
    • 0029619616 scopus 로고
    • Cardiovascular effects of the novel dual inhibitor of neutral endopeptidase and angiotensin converting enzyme BMS-182657 in experimental hypertension and heart failure
    • See: Trippodo, N. C.; Robl, J. A.; Asaad, M. M.; Bird, J. E.; Panchal, B. C.; Schaeffer, T. R.; Fox, M.; Giancarli, M. R.; Cheung, H. S. Cardiovascular effects of the novel dual inhibitor of neutral endopeptidase and angiotensin converting enzyme BMS-182657 in experimental hypertension and heart failure. J. Pharmacol. Exp. Ther. 1995, 275, 745-752, as well as refs 3 and 4 for a description of the AI pressor response assay and the 1-K DOCA salt rat assay. The SHR assay was performed as described in ref 4 utilizing the telemetry techniques outlined by Bazil, M. K.; Krulan, C.; Webb, R. L. Telemetric monitoring of cardiovascular parameters in conscious spontaneously hypertensive rats. J. Cardiovasc. Pharmacol. 1993, 22, 897-905.
    • (1995) J. Pharmacol. Exp. Ther. , vol.275 , pp. 745-752
    • Trippodo, N.C.1    Robl, J.A.2    Asaad, M.M.3    Bird, J.E.4    Panchal, B.C.5    Schaeffer, T.R.6    Fox, M.7    Giancarli, M.R.8    Cheung, H.S.9
  • 26
    • 0027380169 scopus 로고
    • Telemetric monitoring of cardiovascular parameters in conscious spontaneously hypertensive rats
    • See: Trippodo, N. C.; Robl, J. A.; Asaad, M. M.; Bird, J. E.; Panchal, B. C.; Schaeffer, T. R.; Fox, M.; Giancarli, M. R.; Cheung, H. S. Cardiovascular effects of the novel dual inhibitor of neutral endopeptidase and angiotensin converting enzyme BMS-182657 in experimental hypertension and heart failure. J. Pharmacol. Exp. Ther. 1995, 275, 745-752, as well as refs 3 and 4 for a description of the AI pressor response assay and the 1-K DOCA salt rat assay. The SHR assay was performed as described in ref 4 utilizing the telemetry techniques outlined by Bazil, M. K.; Krulan, C.; Webb, R. L. Telemetric monitoring of cardiovascular parameters in conscious spontaneously hypertensive rats. J. Cardiovasc. Pharmacol. 1993, 22, 897-905.
    • (1993) J. Cardiovasc. Pharmacol. , vol.22 , pp. 897-905
    • Bazil, M.K.1    Krulan, C.2    Webb, R.L.3


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