Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-06-07
1999-06-22
Wilson, James O.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514 49, 514 50, 514 51, 514885, 544317, A01N 4354, A61K 3170, C07D23902
Patent
active
059143312
ABSTRACT:
A method and composition for the treatment of HIV and HBV infections in humans is disclosed that includes administering an effective amount of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane, a pharmaceutically acceptable derivative thereof, including a 5' or N.sup.4 alkylated or acylated derivative, or a pharmaceutically acceptable salt thereof, in a pharmaceutically acceptable carrier.
A process for the resolution of a racemic mixture of nucleoside enantiomers is also disclosed that includes the step of exposing the racemic mixture to an enzyme that preferentially catalyzes a reaction in one of the enantiomers.
REFERENCES:
patent: 4000137 (1976-12-01), Dvonch et al.
patent: 4336381 (1982-06-01), Nagata et al.
patent: 4861759 (1989-08-01), Hiroaki et al.
patent: 4879277 (1989-11-01), Mitsuya et al.
patent: 4900828 (1990-02-01), Belica et al.
patent: 4916122 (1990-04-01), Chu et al.
patent: 4963533 (1990-10-01), de Clercq et al.
patent: 5011774 (1991-04-01), Farina et al.
patent: 5041449 (1991-08-01), Belleau et al.
patent: 5041499 (1991-08-01), Belleau et al.
patent: 5047407 (1991-09-01), Belleau et al.
patent: 5059690 (1991-10-01), Zahler et al.
patent: 5071983 (1991-12-01), Koszalka et al.
patent: 5179104 (1993-01-01), Chu et al.
patent: 5185437 (1993-02-01), Koszalka et al.
patent: 5204466 (1993-04-01), Liotta et al.
patent: 5210085 (1993-05-01), Liotta et al.
patent: 5234913 (1993-08-01), Furman, Jr. et al.
patent: 5248776 (1993-09-01), Chu et al.
patent: 5270315 (1993-12-01), Belleau et al.
patent: 5276151 (1994-01-01), Liotta
patent: 5444063 (1995-08-01), Schinazi
patent: 5466805 (1995-11-01), Belleau et al.
patent: 5466806 (1995-11-01), Belleau et al.
patent: 5486520 (1996-01-01), Belleau et al.
patent: 5532246 (1996-07-01), Belleau et al.
patent: 5538975 (1996-07-01), Dionne
patent: 5539116 (1996-07-01), Liotta et al.
patent: 5587480 (1996-12-01), Belleau et al.
patent: 5618820 (1997-04-01), Dionne
patent: 7686617 (1996-07-01), Cheng et al.
patent: 7718806 (1991-06-01), Cheng
patent: 7785545 (1991-10-01), Cheng
Abobo, et al., "Pharmacokinetics of 2',3'-Dideoxy-5-fluoro-3'-thiacytidine in Rats," J. of Pharmaceutical Sciences, 83(1):96-99 (1994).
Agranat and Biedermann, "Intellectual Property and Chirality: Patentability of Enantiomers of Racemic Drugs in a Racemic Switch Scenario," 8th Chirality Conference, Edinburgh, UK (Jul. 2, 1996).
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, 140(2): 735-742 (1986).
Baschang, et al., "The enantiomers of 1.beta.-adenyl-2.alpha.-hydroxy-3.beta.-(hydroxymethyl)cyclobutane," Tetrahedron:Asymmetry, 3(2):193-6 (1992).
Belleau, B., et al., "Design and Activity of a Novel Class of Nucleoside Analogs Effective Against HIV-1," International Conference on AIDS, Montreal, Quebec, Canada, Jun. 4-9, 1989.
Borthwick, et al., "Synthesis and Enzymatic Resolution of Carbocyclic 2'-Ara-Fluoro-Guanosine: A Potent New Anti-Herpetic Agent," J. Chem. Soc. Commun., vol. 10. pp. 656-658 (1988).
Carter, et al., "Activities of (-)-Carbovir and 3'-Azido-3'-Deoxythymidine Against Human Immunodeficiency Virus In Vitro," Antimicrobial Agents and Chemotherapy, 34(6): 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, 267(20):13938-13942 (1992).
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., 29(42):5349-5352 (1988).
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., 37(19):3543-3548 (1988).
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., 32:612 (1989).
Condreay, et al., "Evaluation of the Potent Anti-Hepatitis B Virus Agent Novel In Vivo Model," Antimicrobial Agents and Chemotherapy, 616-619 (1992).
Connolly and Hammer, "Minireview: Antiretroviral Therapy:Reverse Transcriptase Inhibition," Antimicrobial Agents and Chemotherapy, 36(2):245-254 (1992).
Cretton, E., et al., "Catabolism of 3'-Azido-3'-Deoxythymidine in Heptaocytes and Liver Microsomes, with Evidence of Formation of 3'-Amino-3'-Deoxythymidine, a Highly Toxic Catabolite for Human Bone Marrow Cells," Moelcuilar Pharmacology, 39:258-266 (1991).
Cretton, E., et al., "Pharmokinetics of 3'-Azido-3'-Dexoythymidine and its Catabolites and Interactions with Probenecid in Rhesus Monkeys," Antimicrobial Agents and Chemotherapy, 35(5):801-807 (1991).
Doong, Shin-Lian., et al., "Inhibition of the Replication of Hepatitis B Virus in vitro by 2',3'-Dideoxy-3'-Thiacytidine and Related Analogues," Natl. Acad, Sci. USA, 88:8495-8499 (1991).
Feorino, et al., "Prevention of activation of HIV-1 antiviral agents in OM-10.1 cells," Antiviral Chem. & Chemotherapy, 4(1):55-63 (1993).
Frick, et al., "Pharmacokinetics, Oral Bioavailability, and Metabolic Disposition in Rats of Nucleoside Analog Active against Human Immunodeficiency Virus and Hepatitis B Virus," Antimicrobial Agents and Chemotherapy, 37(11):2285-2292 (1993).
Furman, et al., "The Anti-Hepatitis B Virus Activities, Cytotoxicities, and Anabolic Profiles of the (-) and (+) Enantiomers of Antimicrobial Agents and Chemotherapy, 36(12):2686-2692 (1992).
Herdewijn, et al., "Resolution of Aristeromycin Enantiomers," J. Med. Chem., 1985, vol. 28, 1385-1386.
Hoong, et al., "Enzyme-Mediated Enantioselective Preparation of Pure Enantiomers of the Antiviral Agent 2',3'-Dideoxy-5-fluoro-3'-thiacytidine (FTC) and Related Compounds," J. Org. Chem., 57:5563-5565 (1992).
Ito, et al., "Chirally Selective Synthesis of Sugar Moiety of Nucleosides by Chemicoenzymatic Approach: L-and D-Riboses, Showdomycin, and Cordycepin," J. Am. Chem. Soc., 103:6739-6741 (1981).
Jansen, et al., "High-Capacity In Vitro Assessment of Anti-Hepatitis B Virus Compound Selectivity by a Virion-Specific Polymerase Chain Reaction Assay," Antimicrobial Agents and Chemotherapy, 441-447 (1993).
Jeong, L., et al., "Asymmetric Synthesis and Biological Evaluation of .beta.-L-(2R,5S)-and a-L-(2R-5R)-1,3-Oxathiolane-Pyrimidine and -Purine Nucleosides and Potential Anti-HIV Agents," J. Med. Chem., 36(2):181-195 (1993).
Krenitsky, T.A., et al., "3'-Amino-2',3'-Dideoxyribonucleosides of Some Pyrimidines: Synthesis and Biological Activities," J. Med. Chem., vol. 26 (1983).
Krenitsky, et al., "Enzymic Synthesis of Purine D-arabinonucleosides," Carbohydrate Research, 97:139-146 (1981).
Lin, et al., "Potent and Selective In Vitro Activity of 3'-Deoxythmindine-2-Ene-(3'-Deoxy-2',3'Didehyrothymidine Against Human Immunodeficiency Virus," Biochem. Pharm., 36(17):2713-2718 (1987).
Mahnoudian, et al., "Enzymatic Production of Optically Pure (2'R-cis)-2'-deoxy-3'-thiacytidine (3TC, Lamivudine): A Potent Anyi-HIV Agent," Enzyme Microb. Technol., Sep. 1993, vol. 15, 749-755, published by the Glaxo Group Research.
Mitsuya, H., et al., 3'-Azido-3'-Deoxythmidine (BW A 509U): An Antiviral Agent that Inhibits the Infectivity and Cytopathic effect of Human T-Lymphotropic Virus Type III/Lymphadenopathy-Associated Virus In Vitro, Proc. Natl. Acad. Sci., USA, 82:7096-7100 (1985).
Mitsuya, H., et al., "Molecular Targets for AIDS Therapy," Science, vol. 249, pp. 1533-1544 (1990).
Mitsuya, H., et al., "Rapid in Vitro Systems for Assessing Activty of Agents Against HTLV-III/LAV," AIDS:Modern Concepts and Therapeutic Challenges, S. Broder, Ed. pp. 303-333, Marcel-Dekker, New York (1987).
Norbeck, D., et al., "A New 2',3'-Dideoxynucleoside Prototype with In Vitro Activity Against HIV," Tetrahedron Lett., 30(46):6263-6266 (1989).
Ohno, et al., "Synthetic Studies on Biologicall
Choi Woo-Baeg
Liotta Dennis C.
Schinazi Raymond F.
Emory University
Haley Jacqueline
Knowles Sherry M.
Wilson James O.
LandOfFree
Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluoro does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluoro, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluoro will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1708283