Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1992-08-25
1999-07-20
Dees, Jose' G.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
544276, 544277, A61K 31505, C07D47300
Patent
active
059256435
ABSTRACT:
A method and composition for the treatment of humans infected with HIV that includes the administration of an HIV treatment amount of an enantiomerically pure .beta.-D-dioxolanyl purine nucleoside of the formula: ##STR1## wherein R is OH, Cl, NH.sub.2, or H, or a pharmaceutically acceptable salt or derivative of the compound, optionally in a pharmaceutically acceptable carrier or diluent.
REFERENCES:
patent: 4000137 (1976-12-01), Dvonoch et al.
patent: 4336381 (1982-06-01), Nagata et al.
patent: 4861759 (1989-08-01), Mitsuya et al.
patent: 4879277 (1989-11-01), Mitsuya et al.
patent: 4880784 (1989-11-01), Robins et al.
patent: 4916122 (1990-04-01), Chu et al.
patent: 4963533 (1990-10-01), de Clerq et al.
patent: 5041449 (1991-08-01), Belleau et al.
patent: 5047407 (1991-09-01), Belleau et al.
patent: 5059690 (1991-10-01), Zahler et al.
patent: 5122517 (1992-06-01), Vince et al.
patent: 5204466 (1993-04-01), Liotta et al.
patent: 5210085 (1993-05-01), Liotta et al.
patent: 5444063 (1995-08-01), Schinazi
Balzarini, J., et al., "Potent and Selective Anti-HTLV-III/LAV Activity of 2',3'-Dideoxycytidinene the 2',3'-Unsaturated Derivative of 2',3'-Dideoxycytidine," Biochemical and Biophysical Research Communications, vol. 140, No. 2, pp. 735-742 (1986).
Belleau, B., et al., "Design and Activity of a Novel Class of Nucleotide Analogs Effective Against HIV-1," 5th International Conference on AIDS, Montreal, Quebec, Canada, Jun. 4-9, 1989.
Carter, et al., "Activities of (-)-Carbovir and 3'-Azido-3'-Deoxythymidine Against Human Immunodeficiency Virus in Vitro," Antimicrobial Agents and Chemotherapy, vol. 34, No. 6, pp. 1297-1300 (1990).
Chang, Chien-Neng et al., "Deoxycytidine Deaminase-resistant Steroisomer Is the Active Form of (+)-2',3'-Dideoxy-3'-thiacytidine in the Inhibition of Hepatitis B Virus Replication," The Journal of Biological Chemistry, vol. 357, No. 20, pp. 13938-13942.
Chu, et al., "Structure-Activity Relationships of Pyrimidine Nucleosides as Antiviral Agents for Human Immunodeficiency Virus Type 1 in Peripheral Blood Mononuclear Cells," J. Med. Chem. vol. 32, p. 612 (1989).
Chu, et al., "Comparative Activity of 2',3'-Saturated and Unsaturated Pyrimidine and Purine Nucleosides Against Human Immunodeficiency Virus Type 1 in Peripheral Blood Mononuclear Cells," Biochem. Pharm., vol. 37, No. 19, pp. 3543-3548 (1988).
Chu, C.K., et al., "An Efficient Total Synthesis of 3'-Azido-3'-Deoxythiymidine (AZT) and 3'-Azido-2',3'-Dideoxyuridine (AZDDU, CS-87) from D-Mannitol," Tetrahedron Lett. 1988, 5349.
Cretton, E., et al., "Pharmokinetics of 3'-Azido-3'-Dexoythymidine and its Catabolites and Interactions with Probenecid in Rhesus Monkeys," Antimicrobial Agents and Chemotherapy, pp. 801-807 (1991).
Furman, et al., "The Anti-Hepatitis B Virus Activities, Cytotoxicities, and Anabolic Profiles of the (-) and (+) Enantiomers of Antimicrobial Agents and Chemotherapy, vol. 36, No. 12, pp. 2686-2692.
Jeong, L., et al., "Asymmetric Synthesis and Biological Evaluation of .beta.-L-(2R,5S)-and .alpha.-L-(2R-5R)-1,3-Oxathiolane-Pyrimidine and -Purine Nucleosides and Potential Anti-HIV Agents," J. Med. Chem. vol. 36 (1993).
Lin, et al., "Potent and Selective In Vitro Activity of 3'-Deoxythmindine-2-Ene-(3'-Deoxy-2',3'-Didehydrothymidine) Against Human Immunodeficiency Virus," Biochem. Pharm. vol. 36, No. 17, p. 2716 (1987).
Mitsuya, H., et al., "Rapid in Vitro Systems for Assessing Activity of Agents Against HTLV-III/LAV," AIDS: Modern Concepts and Therapeutic Challenges, S. Broder, Ed. (Marcel-Dekker, New York, 1987), p. 303.
Mitsuya, J., et al., 3'-Azido-3'-Deoxythymidine (BW A 509U): An Antiviral Agent that Inhibitis the Infectivity and Cytopathic Effect of Human T-Lymphotropic Virus Type III/Lymphadenopathy-Associated Virus In Vitro, Proc. Natl. Acad. Sci., USA, vol. 82, pp. 7097-7100 (1985).
Norbeck, D., et al., "A New 2',3'-Dideoxynucleoside Prototype with In Vitro Activity Against HIV," Tetrahedron Lett. 1989, 6263.
Okabe, M., et al., "Synthesis of the Dideoxynucleosides ddC and CNT from Glutamic Acid, Ribonolactone, and Pyrimidine Bases," J. Org. Chem. 1989.
Richman, D. D., et al., "The Toxicity of Azidothymidine (AZT) in the Treatment of Patients with AIDS and AIDS-Related Complex," N. Eng. J. Med. 1987, 317:192.
Satsumabayashi, S. et al., "The Synthesis of 1,3-Oxathiolane-5-one Derivatives," Bull. Chem. Soc. Japan, 1972, 45:913.
Schinazi, R.F., et al., "Activities of the Four Optical Isomers of 2',3'-Dideoxy-3'-Thiacytidine (BCH-189) against Human Immunodeficiency Virus Type 1 in Human Lymphocytes," Antimicrobial Agents and Chemotherapy 36(3) 672-676 (1992).
Schinazi, R.F., et al., "Insights nito HIV Chemotherapy," AIDS Research and Human Retroviruses 8(6) (1992) 963-990.
Schinazi, R.F., et al., "Pharmacokinetics and Metabolism of Racemic 2',3'-Dideoxy-5-Fluoro-3'-Thiacytidine in Rhesus Monkeys," Antimicrobial Agents and Chemotherapy 36(11) 2432-2438 (1992).
Schinazi, R.F., et al., "Selective Inhibition of Human Immunodeficiency Viruses by Racemates and Enantiomers of Antimicrobial Agents and Chemotherapy 36(11) 2423-2431 (1992.
Schinazi, R.F., et al., "Substrate Specificity of Escherichia coli Thymidine Phosphorylase for Pyrimidine Nucleoside with an Anti-Human Immunodeficiency Virus Activity," Biochemical Pharmacology 44(2) (1992) 199-204.
Storer, Richard, et al., "The Resolution and Absolute Stereochemistry of the Enantiomers of Anti-HIV Agents," Nucleosides &Nucleotides, 12(2), 225-236 (1993).
Vorbruggen et al, "Nucleoside Synthesis with Trimethylsilyl Triflate and Perchlorate as Catalysts," Chem. Ber. 1981, 114:1234-1255.
Wilson, L.J., et al. "A General Method for Controlling Glycosylation Stereochemistry in the Synthesis of 2'-Deoxyribose Nucleosides," Tetrahedron Lett. 1990, 1815.
Zhu, Zhou, et al., "Cellular Metabolism of 3'-Azido-2',3'-Dideoxyuridine with Formation of 5'-O-Diphophoshexase Derivatives by Previously Unrecognized Metabolic Pathways of 2'-Deoxyuridine Analogs," Molecular Pharmacology, vol. 38, pp. 929-938.
Saari et al, J. Med. Chem. 1992, 35, 3792-3802.
Gerlt, Chem. Abst. 107:14979 (1987).
Boutelje et al, Chem Abst 108:128048 (1987).
Norin, Chem Abst 108:146380 (1987).
Ohno et al. Chem Abst 112:194612 (1989).
Belleau et al, 112CA:198359W 1990.
Kim, H.O., et al., "L-.beta.-(2S,4S)-and L-.alpha.-(2S-4R)-Dioxolanyl Nucleosides as Potential Anti-HIV Agents: Asymmetric Synthesis and Structure-Activity Relationships," J. Med. Chem., 1993, 36, 519-528.
Kim, H.O., et al., "1,3-Dioxolanylpurine Nucelosides (2R,4R) and (2R,4S) with Selective Anti-HIV-1 Activity in Human Lymphocytes," J. Med. Chem. 1993, 36, 30-37.
Wilson, L.J., et al., "The Synthesis and Anti-HIV Activity of Pyrimidine Dioxolanyl Nucleosides," Bioorganic & Medicinal Chemistry Letters, 1993, 3, 169-174.
Dees Jos,e G.
Emory University
Haley Jacqueline
Knowles Sherry M.
Qazi Sabiha N.
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