Novel peptidyl carbamate inhibitors of the enzyme elastase

Details Novel peptidyl carbamate inhibitors of the enzyme elastase Novel peptidyl carbamate inhibitors of the enzyme elastase

1988-10-27

1991-04-16

Lee, Mary C.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

514 19, 514381, 514423, 548251, 548536, A61K 3764, C07K 508

Patent

active

050082450

ABSTRACT:
Compounds selected from the group consisting of a compound of the formula ##STR1## and compound of the formula ##STR2## wherein x is 1 or 2,

REFERENCES:
patent: 4643991 (1987-02-01), Digenis et al.
Digenis, George A., Agha, Bushra, J., Tsuji, Kiyoshi, Kato, Masayuki and Shinogi, Masaki; "Peptidyl Carbamates Incorporating Amino Acid Isosteres as Novel Elastase Inhibitors" Journal of Medicinal Chemistry, 1986, 29, 1468.
Zimmerman, Morris, Morman, Harriet, Mulvey Dennis, Jones, Howard, Frankshun, Robert and Ashe, Bonnie M.; "Inhibition of Elastase and Other Serine Proteases by Heterocyclic Acylating Agents", Journal Biol. Chemistry, vol. 255, No. 20, pp. 9848-9851, 1980.
Janoff, Aaron and Dearing, Rosemarie: "Prevention of Elastase-Induced Experimental Emphysema by Oral Administration of a Synthetic Elastase Inhibitor", American Review of Respiratory Disease, vol. 121, 1980.
Tsuji, K., Agha, B. J., Shinogi, M. and Digenis, G. A.: "Peptidyl Carbamate Esters: A New Class of Specific Elastase Inhibitors", Biochem. & Biophys. Comm., vol. 122, No. 2, 1984, pp. 571-576.
Scofield, Rolfe, E., Werner, P. and Wold, Finn: "p-Nitrophenyl Carbamates as Active-Site-Specific Reagents for Serine Proteases", Biochemistry 16 (11) (1977).
Ashe, Bonnie M., Clark, Robert L., Jones, Howard and Zimmerman, Morris: "Selective Inhibition of Human Leukocyte Elastase and Bovine a-Chymotrypsin by Novel Heterocycles", Journal of Biological Chemistry, No. 22, Issue of Nov. 25, pp. 11603-11606, 1981.
Dorn, Conrad P., Zimmerman, Morris, Yang, Shu Shu, Yurewicz, Edward C., Ashe, Bonnie M., Frankshun, Robert and Jones, Howard: "Proteinase Inhibitors. I. Inhibitors of Elastase", Journal of Medicinal Chemistry, 1977, vol. 20, No. 11.
Doyle, B. B., Traub, W., Lorenzi, G. P., Brown, III, F. R. and Blout, E. R.: "Synthesis and Structural Investigation of Poly(L-Alanyl-L-Alanyl-Glycine)", J. Mol. Biol. (1970) 51, 47 59.
Vlasak, J., Rypacek, F., Drobnik, J. and Saudek, V.: "Properties and Reactivity of Polysuccinimide" Institute of Macromolecular Chemistry, Czechoslovak Academy of Sciences, 162 06 Prague 6, Czechoslovakia, (1979).
Brown, Harold H.: "A Study of 2,4,6-Trinitrobenzenesulfonic Acid for Automated Amino Acid Chromatography", Clinical Chemistry, vol. 14, No. 10, 1968, pp. 967-978.
Neri, Paolo, Antoni, Guido, Benvenuti, Franco, Cocola, Francesco and Gazzei, Guido: "Synthesis of .alpha.,.beta., -Poly [(2-Hydroxyethyl)-DL-Aspartamide], a New Plasma Expander", Journal of Medicinal Chemistry, 1973, vol. 16, No. 8.
Tsuji, K., Agha, B. J., Shinogi, M., Digenis, G. A.: "Peptidyl Carbamate Esters: A New Class of Specific Elastase Inhibitors", Biochemical and Biphysical Research Communications, vol. 122, No. 2, 1984, Jul. 31, 1984, pp. 571-576.
Tuhy, Peter M. and Powers, James C.: "Inhibition of Human Leukocyte Elastase by Peptide Chloromethyl Ketones", Feb. 1975.
Powers, James C., Gupton, B. Frank, Harley, A. Dale, Nishino, Norikazu and Whitley, Ronald J.: "Specificity of Porcine Pancreatic Elastase, Human Leukocyte Elastase and Cathepsin G", Inhibition with Peptide Chloromethyl Ketones, Biochemica et Biophysica Act. 485 (1977) 156-166.
Yoshimura, Toshiaki, Barker, Larry N. and Powers, James C.: "Specificity and Reactivity of Human Leukocyte Elastase, Porcine Pancreatic Elastase, Human Granulocyte Cathepsin G. and Bovine Pancreatic Chymotrypsin with Arylsulfonyl Fluorides" J. Biol. Chem. 257, 5077-5084 (1972).
Groutas, William C., Abrams, William R., Theodorakis, Michael C., Kasper, Annette M., Rude, Steven A.Badger, Robert C., Ocain, Timothy D., Miller, Kevin E., Moi, Min K., Brubaker, Michael J., Davis, Kathy S. and Zandler, Melvin E.: "Amino Acid Derived Latent Isocyanates: Irreversible Inactivation of Porcine Pancreatic Elastase and Human Leuokocyte Elastase", J. Med. Chem. 1985 28, 204-209.

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