Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-09-17
2000-05-09
Rotman, Alan L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
544238, 549331, 549477, 514278, C07D491107, C07D49102, C07D30700
Patent
active
060606002
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
PCT/US94/09533, filed Sep. 7, 1994.
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 (Feb. 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 4-Substituted 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 e
REFERENCES:
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).
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, Abstract, published Aug. 3, 1992; Yoji, Shirokura.
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 (Feb. 1994).
Roggo, B. E., et al., "3-Alkanoyl-5-Hydroxymethyl Tetronic Acid Homologues and Resistomycin: New Inhibitors of HIV-1 Protesase, II. Structure Determination" J. of Antibiotics, vol. 47, No. 2, pp. 143-147 (Feb. 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).
Chemical Abstracts, vol. 98: 119144p, p. 20 (1983).
Chemical Abstracts, vol. 90: 185907a, p. 575 (1979).
Chemical Abstracts, vol. 90: 114925u, p. 28 (1979).
Chemical Abstracts, vol. 55, col. 16687, paragraph f.
Fell, S.C.M. et al. "Synthesis of 4-Substituted Tetronic Acids: Multicolanic Acid." J. Chem. Soc., Chem. Commun., vol. 2, pp. 81-82 (1979).
Chemical Abstracts, vol. 34, Alicyclic Compounds (1963), Col. 2378, paragraph f.
Chemical Abstracts, vol. 118: 45729r, p. 457 (1993).
Sibi M.P. et al., "A Convenient Synthesis of 3-alkyltetronic acids from 3-acyletronic acids." Synthetic Communications, vol. 22, No. 6, pp. 809-816 (1992).
Arai K., et al. "Metabolites of Penicillium italicum Wehmer: Isolation and Structures of New Metabolites Including Naturally Occurring 4-ylidene-acyltetronic Acids, Italicinic Acid and Italicic Acid." Chem Pharm. Bull., vol. 37, No. 12, pp. 3229-3235 (1989).
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Gudgeon, J.A., et al, "The Structures and Biosynthesis of Multicolanic, Multicolic and Multicolosic Acis, Novel Tetronic Acid Metabolites of Penicillium Multicolor." Bioorganic Chemistry, vol. 8, pp. 311-322 (1979).
Gudgeon, J.A., et al, "Use of singly and doubly labeled carbon-13-acetate in the elucidation of the structures and biosynthesis of multicolic and multicolosic acids, new tetronic acids from Penicillium multicolor." J. Chem. Soc., Chem. Commun., vol. 16, pp. 636-8 (1974).
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Chemical Abstracts, vol. 63, col. 13064, paragraph "a," (1965).
Aristoff Paul A.
Chruscial Robert A.
Howe W. Jeffrey
Maggiora Linda L.
Skulnick Harvey I.
Pharmacia & Upjohn Company
Rotman Alan L.
Wootton Thomas A.
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