Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-07-28
1999-11-02
Owens, Amelia
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514274, 514278, 514312, 514314, 514336, 514382, 514395, 514397, 514462, 514471, 549265, 549313, 544316, 546 16, 546 17, 5462844, 548251, 5483047, 5483401, A61K 3134, A61K 31335, A61K 31415, A61K 31505
Patent
active
059771690
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention comprises novel substituted tetronic acid type compounds, 2,4-(3H,5H)-furandiones, that are useful for the inhibition of the HIV protease enzyme. The compounds may be useful for the treatment of a person with AIDS or AIDS related diseases. The compounds may be used in the attempt to retard the further replication of any retrovirus containing the aspartyl protease enzyme.
2. Information Disclosure
WO 93/04055, published Mar. 4, 1993, inventor Dolak, Lester, et al. A tetronic acid useful for the inhibition of HIV-protease.
EP 0,259,707-A2 published Mar. 16, 1988, assigned to Takeda Chemical; Terao, Shinji et al., Hydroxybutenolide Derivatives useful for scavenging active oxygen species.
JP 05043568-A (90JP-202268) published Feb. 23, 1993, assigned to Takeda Chemical, disclosing tetronic acids used to treat inflammatory diseases.
Rehse, K., et al., "Anticoagulant Activity of 3,5-Disubstituted Tetronic Acids," Arch. Pharm. (Weinheim) Vol. 311, pp. 986-992 (1978).
Rehse, K., and Wagenknecht, J., "Mass Spectrometric Investigation of Anticoagulant 3-(1-Arylpropyl)-tetronic Acids," Arch. Pharm. (Weinheim), Vol. 312, pp. 164-168 (1979).
Rehse, K., et al., "Protein Binding of Drugs Determined by Continuous Ultrafiltration, III: Protein Binding of Anticoagulant Tetronic Acids," Arch. Pharm. (Weinheim) Vol. 315, pp. 052-056 (1982).
EP 0,534,907-A1, (92JP-276543) published Mar. 31, 1993, assigned to Nippon Zoki Pharmaceutical disclosing 2-(5H)-furanones to treat auto-immune diseases.
J. Synthetic Org. Chem. Japan, Vol. 44, No. 2, pp. 127--(1986),
Vekemans, J., "An Efficient Synthesis of (S)-5-Hydroxymethyl-2(5H)-Furanone" Tetrahedron Letters, Vol. 28, No. 20, pp. 2299-2300 (1987),
J. Org. Chem., Vol. 46, pp. 2299--(1981),
Kokai Number Hei-4-211676, published Aug. 3, 1992; Yoji, Shirokura. A tetronic acid useful as a vasodilator.
Roggo, B. E., et al., "3-Alkanoyl-5-Hydroxymethyl Tetronic Acid Homologues and Resistomycin: New Inhibitors of HIV-1 Protease, I. Fermentation, Isolation and Biological Activity" J. of Antibiotics, Vol. 47, No. 2, pp. 136-142 (February 1994).
Roggo, B. E., et al., "3-Alkanoyl-5-Hydroxymethyl Tetronic Acid Homologues and Resistomycin: New Inhibitors of HIV-1 Protease, II. Structure Determination" J. of Antibiotics, Vol. 47, No. 2, pp. 143-147 (February 1994).
Lang, Marc and Roesel, Johannes, "HIV-1 Protease Inhibitors: Development, Status and Potential Role in the Treatment of AIDS," Archives of Pharmacy, Vol. 326, pp. 921-924 (1993). Undisclosed tetronic acid-type compounds thought to be possible HIV-1 protease inhibitor.
Chemical Abstracts, Vol. 98: 119144p (1983) page 20, anticoagulant activity of 3-arylalkyl-5-phenyl tetronic acids. 10 tetronic acid derivatives. Registry number of one compound is 80936-00-1, CA index name, 2(5H)- Furanone, 3-(1-(4-chlorophenyl)ethyl)-4-hydroxy-5-methyl- (9CI).
Chemical Abstracts, Vol. 90: 185907a (1979) page 575, Mass spectrometric investigation of anticoagulant 3-(1-arylpropyl) tetronic acids. Tetronic acid derivatives. Registry number of one compound, 69354-72-9, CA index name, 2(5H)- Furanone, 4-hydroxy-5-methyl-3-(1-phenylpropyl)- (9CI).
Chemical Abstracts, Vol. 90: 114925u (1979) page 28, Anticoagulant activity of 3-5-disubstituted tetronic acids. Tetronic acid derivatives. Registry number of one compound, 69354-71-8, CA index name, 2(5H)- Furanone, 3-(1-(4-chlorophenyl)propyl)-4-hydroxy-5-methyl-(9CI).
Chemical Abstracts, Vol. 55, Column 16687, paragraph f, disclosure of 3-(1-aminoethyl)-5-methyltetronic acid. Registry number 89910-36-1. CA index name, valeric acid, 2-(1-aminoethyl)-4-hydroxy-3-oxo, gamma. -lactone (6CI, 7CI).
Fell, S. C. M. et al. "Synthesis of 4Substituted Tetronic Acids: Multicolanic Acid." J. Chem. Soc., Chem. Commun., Vol. 2, pp. 81-2 (1979).
Chemical Abstracts, Vol. 34, Alicyclic Compounds (1963), Column 2378, paragraph f, disclosure of ethyl and methyl benzyltetronic acid. Registry number 91910-33-7. CA index name, valeric acid, 2 ethyl-4-hydroxy-3-oxo-5-pheny
REFERENCES:
Rehse, K., et al., Arch. Pharm., 311, pp. 986-992 (1978.
Rehse, K., et al., Arch. Pharm., 312, pp. 164-168 (1979).
Rehse, K., et al., Arch. Pharm., 315, pp. 052-056 (1982).
J. Synthetic Org. Chem., Japan, 44, 2, pp. 127-(1986).
Vekemans, J., et al., Tetrahedron Letters, 28, 20, pp. 2299-2300 (1987).
Roggo, B., et al., J. of Antibiotics, 47, 2, pp. 136-142 (1994).
Roggo, B., et al., J. of Antibiotics, 47, 2, pp. 143-147 (1994).
Lang, M., et al., Arch. Pharm., 326, pp. 921-924 (1993).
CA, 91:68274b (1979).
CA, 98:119144p (1983).
CA, 90:185907a (1979).
CA, 90:114925u (1979).
CA, 55:16687, f.
Fell, S.C.M. et al, J.C.S. Chem Comm., "Synthesis of 4-Substituted Tetronic Acids: Multicolanic Acid," pp. 81-2 (1979).
CA, 34:2378, f (1963).
CA, 118:45729r (1993).
Sibi, M.P. et al, Synthetic Communications, 22(6), "A Convenient Synthesis of 3-Alkyltetronic Acids from 3-Acyltetronic Acids," 809-816 (1992).
Arai, K., et al., Chem. Pharm. Bull., 37(12), "Metabolites of Penicillium italicum Wehmer: Isolation and Structures . . . " 3229-3235 (1989).
Wakabayashi, H., et al., Chemistry Letters, "Synthesis of Optically Active Litsenolide C," 875-878 (1987).
Buck, J., et al, J. Chem. Soc. Perkin Trans. 1, "Directed Metallations of 4-Ethylidenetetronic Acid O-Methyl Ether . . . ," 2399-2405 (1985).
Wanwagenen, B.C. et al. Tetrahedron, 42(4), "Native American Food and Medicidnal Plans 7 . . . ," 1117-1122 (1986).
CA, 97:109463g (1982).
Anderson, J.R., et al, J.C.S. Perkin I, 1, "Metabolites of the Higher Fungi. Part 19.sup.1 . . . " 215-221 (1982).
CA, 87:184299e (1977).
Damon, R.E., et al., Tetrahedron Letters, No. 32, "A General Synthesis of 2-Alkyl Tetronic Acids," 2749-2752 (1976).
Gudgeon, J.A., et al, Bioorganic Chemistry, 8, "The Structures and Biosynthesis of Multicolanic . . . " 311-322 (1979).
Gudgeon, J.A., et al, J.C.S. Chem. Commun., "Use of Singly and Doubly Labelled .sup.13 C-Acetate . . . ," 636-638 (1974).
Sudo, R., et al, J. Org. Chem., 32(6), "Synthesis of Carolic Acid," 1844-1846.
CA registry No. 6232-63-9 CA index name, 2,4(3H,5H)-Furandione,3-(2-iminoethyl)-5-methyl-(8CI, 9CI).
CA, 63:13064, a (1965).
Aristoff Paul A.
Bundy Gordon L.
Chrusciel Robert A.
Howe W. Jeffrey
Maggiora Linda L.
Owens Amelia
Wootton Thomas A.
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