Phosphonic acid derivatives and use thereof

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Claims

2. The compound according to claim 1, in which R.sub.1 is selected from the group which consists of an alkyl group having 1 to 12 carbon atoms; a 5-, 6- or 7-membered alicyclic alkyl group; and an alkyl group having 1 to 5 carbon atoms substituted by an aromatic hydrocarbon group having 6 to 12 carbon atoms.

Referenced Cited
U.S. Patent Documents
4379146 April 5, 1983 Greenlee et al.
4432972 February 21, 1984 Karanewsky et al.
Other references
  • Proc. Natl. Acad. Sci. USA-"Phosphorus-containing Inhibitors of Antiotensin-converting Enzyme", vol. 79, pp. 2176-2180, Apr. 1982. Biochemistry, "Phosphonamidates as Transition-State analogue Inhibitors of Thermolysin", 22, 4618-4624, 1982. Biochemical and Biophysical Res. Comm., "Inhbitions of Biological Actions of Big Endothelin-1 by Phosphoramidon" vol. 172, No. 2, pp. 390-395, 1990. Grobelny et al, "Binding Enregetics of Phosphorus-containingInhibitors of Thermolysin", Biochemistry, vol. 28, No. 12 pp. 4948-4951, 1989. Wakimasu, Rule 132 Declaration, Paper #10, File Wrapper of U.S. Patent No. 5,330,978 (admissions). Morgan et al, "Differential Binding Energy: A Detailed Evaluation of the Influence of Hydrogen-Bonding and Hydrophobic Groups on the Inhibition of Thermolysin by Phosphorus containing Inhibitors", Journal of the American Chemical Society, vol. 113, No. 1, 1991. Kam et al, "Inhibition of Thermolysin and Carboxypeptidase A by Phosphamidates", Biochemistry, vol. 18, No. 14, pp. 3032-3038, 1979. Mookhtiar, K.A., et al. "Phosphonamidate Inhibitors of Human Neutrophil Collagenase", Biochemistry, vol. 26, No. 7 (1987) (pp. 1962-1965). McMahon et al., "Phosphoramidon Blocks The Pressor Activity of Porcine Big Endothelin-1-(1-39) In Vivo and Conversion of Big Endothelin-1-(1-39), 2 Endothelin-1-(1-21) In Vitro", Proceedings National Academy of Science, vol. 88 (Feb. 1991), pp. 703-777. Rich, H. David, "Peptidase Inhibitors" in Comprehensive Medicinal Chemistry The Rational Design, Mechanistic Study & Therapeutic Application of Chemical Compounds, vol. 2 (Pergamon Press PLC), pp. 391-496 (not continuous), 1990. Carey, et al., "Reaction and Synthesis": Chapter 11 entitled Multistep Synthesis at pp. 539-553, Advanced Organic Chemicstry, Second Ed. Part B (New York Plenum Press, 1983). Merz, et al., "Free Perturbation Simulations of the Inhibition of Thermolysin: Prediction of the Free Energy of Binding of a New Inhibitor", J. Am. Chem. Soc., vol. 111, No. 15 (1989), pp. 5649-5658.
Patent History
Patent number: RE35886
Type: Grant
Filed: Jul 12, 1996
Date of Patent: Sep 1, 1998
Assignee: Takeda Chemical Industries, Ltd. (Osaka)
Inventors: Mitsuhiro Wakimasu (Osaka), Masaaki Mori (Tsukuba), Akira Kawada (Tsukuba)
Primary Examiner: Johann Richter
Assistant Examiner: Joseph Murray
Attorneys: David G. Conlin, George W. Neuner
Application Number: 8/680,295