Acylated enol derivatives of .alpha.-ketoesters and .alpha.-keto

Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – 4 to 5 amino acid residues in defined sequence

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530331, 514 18, 514851, C07K 500

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059488867

ABSTRACT:
This invention relates to acylated enol derivatives of .alpha.-ketoesters and .alpha.-ketoamides. The compounds of this invention are either prodrugs of known elastase inhibitors or are elastase inhibitors in their own right and are useful in the treatment of various inflammatory diseases, including cystic fibrosis and emphysema.

REFERENCES:
patent: 4277395 (1981-07-01), Bey et al.
patent: 4518528 (1985-05-01), Rasnick
patent: 4623639 (1986-11-01), Hassall et al.
patent: 4629724 (1986-12-01), Ryono et al.
patent: 4636489 (1987-01-01), Seemuller et al.
patent: 4643991 (1987-02-01), Digenis et al.
patent: 4855303 (1989-08-01), Hoover
patent: 4873221 (1989-10-01), Trainor
patent: 4880780 (1989-11-01), Trainor et al.
patent: 4910190 (1990-03-01), Bergeson et al.
patent: 4935405 (1990-06-01), Hoover et al.
patent: 5055450 (1991-10-01), Edwards et al.
patent: 5114927 (1992-05-01), Schirlin
patent: 5162307 (1992-11-01), Digenis et al.
patent: 5221665 (1993-06-01), Skiles et al.
patent: 5478811 (1995-12-01), Peet et al.
patent: 5496927 (1996-03-01), Kolb et al.
patent: 5510333 (1996-04-01), Angelastro et al.
Skiles et al., J. Med. Chem. 1992, 35, pp. 641-662, Inhibition of Human Leukocyte Elastase (HLE) by N-Substituted Peptidyl Trifluoromethyl Ketones1.
Skiles et al., J. Med. Chem. 1992, 35, pp. 4795-4808, Inhibition of Human Leukocyte Elastase by N-Substituted Peptides Containing alpha, alpha-Difluorostatone Residues at P1.
Williams et al., publication, Biologic Characterization of ICI 200,880 and ICI 200,355, Novel Inhibitors of Human Neutrophil Elastase 1,2.
Kawase et al., Tetrahedron Letters, vol. 34, No. 5, pp. 859-862, 1993, "Unexpected Product from the Dakin-West Reaction of N-Acylprolines using Trifluoroacetic Anhydride: A Novel Access to 5-Trifluoromethyl-oaxzoles".
Kawase et al., J. Chem. Soc., Chem. Commun., 1992, pp. 1076-1077, "Unusual Ring Expansion observed during the Dakin-West Reaction of Tetrahydroisoquinoline-1-carboxlic Acids using Trifluoroacetic Anhydride: an Expedient Synthesis of 3-Benzazepine Derivatives bearing a Trifluoromethyl Group".
Imperiali et al, Biochemistry 25, 3760-3767, (1986).
kiles et al, Journal of Medicinal Chemistry, vol. 35, No. 4, pp. 641-661 (1992).
Repine et al, J Med Chem. 34, pp. 1935-1943 (1991).
Ueda et al, Biochem. J. 265 pp. 539-545 (1990).
Eleventh American Peptide Symposium--Jul. 9-14, 1989.
Sham et al, FEB 05016, vol. 220, No. 2, pp. 299-301 (1987).
Travis et al, Am. Rev. Respir, Dis. 143:1412-1415, (1991).
Petrillo et al, Annual Reports in Medicinal Chemistry 25, pp. 51-60.
Powers et al, Chemical Abstracts, vol. 108:33954r, 1988, Mechanism-based inhibitors of human leukocyte elastase.
Chemical Abstract vol. 111, No. 9, Aug. 28, 1989, Lafuma et al. p. 17.
Chemical Abstract vol. 111, No. 21, Nov. 20, 1989, Galzigna et al, p. 343.
Steinmeyer et al, Forsch./Drug Res. 41, (I) Nr. (1991).
McWherter et al, Biochemistry 28, pp. 5708-5713 (1989).
Reilly et al, Biochemica et Biophysica Acta. 621 pp. 147-157, (1980).
Najajima et al, Journal of Biological Chemistry, vol. 254, pp. 4027-4031 (1979).
Rice et al, Science, vol. 249, pp. 178-181.
Travis, The American Journal of Medicine, vol. 84, Supl. 6A pp. 37-42 (1988).
Peet et al., J. Med. Chem. 33, pp. 394-407 (1990).
Doherty et al, Int. J. Immunopharmac vol. No. 7, pp. 787-795, (1990).
Mehdi et al, Biochemical and Biophysical Research Communications, vol. 166, No. 2, pp. 595-600 (1990).
Shah et al, Orally Active .beta.-Latham Inhibitors of Human Leukocyte Elastase-1. J. Med Chem, 35, pp. 3745-3754 (1992).
Snider, Eur, J. Respir. 69, suppl 146, 17-35 (1986).
Malech et al, Medical Intelligence vol. 317, No. 11, pp. 687-694.
Fletcher et al, Am Rev Respir Dis 1990, 141:672-677.
Hassall et al, Febs 2444, vol. 183, No. 2, (1985).
Angelastro et al, J. Org. Chem. 54, pp. 3913-3916, (1989).
Angelastro et al, Journal of Medicinal Chemistry, 37, pp. 4538-4553 (1994).
Angelastro et al, Bioorganic & Medicinal Chemistry Letters, vol. 3, No. 4, pp. 525-530 (1993).
Mehdi, Bioorganic Chemistry, 21, pp. 249-259 (1993).
Angelastro et al., Tetrahedron Letters, vol. 33, No. 23, pp. 3265-3268 (1992).
Burkhart et al., Tetrahedron Letters, vol. 31, No. 10, pp. 1385-1388 (1990).
Angelastro et al, Bioorganic & Medicinal Chemistry Letters, vol. 2, No. 10, pp. 1235-1238 (1992).
J. Med. Chem. 33, pp. 11-13 (1990) Communications to the Editor.
Bundgaard, Hans, "Design of Bioreversible Drug Derivatives and the Utility of the Double Prodrug Concept", Bioreversible Carriers In Drug Design Theory and Application, Chapter 2, pp. 62-65.
Janusz, M. et al, J. Immonol. (1991), vol. 146, pp. 3922-3928.
Janusz, M. et al, J. Pharmacol. Exp. Ther., (1995), vol. 275, pp. 1233-1238.
Zhaozhao Li et al, J. of Medicinal Chemistry, vol. 36, No. 22, pp. 3742-3480, Oct. 29, 1993.
Isabel Charles et al, J. of the Chemical Society, Perkin Transactions 1. No. 5, pp. 1139-1146, May 1980.
Burkhart et al., J. Med. Chem., 38, 223-233, 1995.

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