Phosphorous-containing cysteine and serine protease inhibitors

Details Phosphorous-containing cysteine and serine protease inhibitors Phosphorous-containing cysteine and serine protease inhibitors

1996-07-10

1997-06-17

Richter, Johann

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

514110, 514119, 536 187, 544157, 548413, 558 73, 558 82, 558 83, 558 86, 558170, 558174, 562 15, A61K 3166, C07F 909, C07F 930, C07F 932

Patent

active

056397321

ABSTRACT:
The present invention is directed to novel phosphorous-containing inhibitors of cysteine or serine proteases. Methods for the use of the protease inhibitors are also described.

REFERENCES:
Dolle, R.E. et al., "Aspartyl .alpha.-((Diphenylphosphinyl)oxy) methyl Ketones as Novel Inhibitors of Interleukin-1.beta. Converting Enzyme. Utility of the Diphenylphosphinic Acid Leaving Group for the Inhibition of Cysteine Proteases", J. Med. Chem., 1995, 38, 220-222.
Harbeson, Scott L. et al., "Inhibition of Aminopeptidases by Peptides Containing Ketomethylene and Hydroxyethylene Amide Bond Replacements", J. Med. Chem., 1989, 32, 1378-1392.
Repine, Joseph T. et al., "Renin Inhibitors Containing .alpha.-Heteroatom Amino Acids as P.sub.2 Residues.sup.1 ", J. Med. Chem., 1992, 35, 1032-1042.
Rich, Daniel H. et al., "New Hydroxyethylamine HIV Protease Inhibitors That Suppress Viral Replication", J. Med. Chem., 1992, 35, 3803-3812.
Goel, O.P. et al., Org. Syn., 1993, Coll. vol. VIII, 68.
Montchamp, J. et al., "Double Arbuzov Reaction of in Situ Generated Bis(trimethylsiloxy)phosphine with Dielectrophiles: Methodology for the Synthesis of Cyclic Phosphinic Acids", J. Org. Chem., 1995, 60, 6076-6081.
Froestl, W. et al., "Phosphinic Acid Analogues of GABA. 2. Selective, Orally Active GABA.sub.B Antagonists", J. Med. Chem., 1995, 38, 3313-3331.
Adams, R.R. et al., "Heterocyclic Basic Compounds. IV. 2-Aminoalkylamino-pyrimidines.sup.1 ", J. Am. Chem. Soc., 1945, 67, 735-738.
Texier-Boullet, F. et al., "A Convenient Synthesis of Dialkyl 1-Hydroxyalkanephosphonates using Potassium or Caesium Fluoride without Solvent", Synthesis, 1982, 165.
Schlemmer, H. et al., "Phosphorus-31 Nuclear Magnetic Resonance Spectroscopy of the Phosphorylated Tetrapeptide Gly-Gly-Asp-Ala", Magn. Reson. Chem., 1988, 26(3), 260-3, abstract. (Note compound with registricy no. 117289-76-6.) (Database CAPLUS on STN International, Chemical Abstracts Service, (Columbus, OH), Accession No. 1988:611439.).
Sterling-Winthrop, Inc., "Preparation of Peptide Derivatives as Interleukin 1.beta.-converting Enzyme Inhibitors", JP 07025887 A2, Jpn. Kokai Tokkyo Koho, 1995, abstract. (Note listing of disclosed compounds.) (Database CAPLUS on STN, Chemical Abstracts Services, (Columbus, OH), Accession No. 1995:867576.).
Ramage, R. et al., "Application of Phosphinic Acids to Peptide Synthesis", Pept. Proc. Eur. Pept. Symp., 17th, (1983), Meeting Date 1982, 157-62, abstract. (Note compound with registry no. 88577-10-0.) (Database CAPLUS on STN, Chemical Abstracts Services, (Columbus, OH), Accession No. 1984:51966.).

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