Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2008-07-22
2008-07-22
Balasubram, Venkataraman (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C544S317000, C536S026800
Reexamination Certificate
active
11390861
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 N4alkylated 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), 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: 4916122 (1990-04-01), Chu et al.
patent: 4963533 (1990-10-01), de Clercq 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: 5204466 (1993-04-01), Liotta et al.
patent: 5210085 (1993-05-01), Liotta et al.
patent: 5234913 (1993-08-01), Furman et al.
patent: 5618820 (1997-04-01), Dionne
patent: 5814639 (1998-09-01), Liotta et al.
patent: 5914331 (1999-06-01), Liotta et al.
patent: 6114343 (2000-09-01), Liotta et al.
patent: 6350753 (2002-02-01), Belleau et al.
patent: 6642245 (2003-11-01), Liotta et al.
patent: 6703396 (2004-03-01), Liotta et al.
patent: 2002/0143194 (2002-10-01), Liotta et al.
patent: 2004/0038350 (2004-02-01), Liotta et al.
patent: 2004/0171124 (2004-09-01), Liotta et al.
patent: 2005/0004148 (2005-01-01), Liotta et al.
patent: 2005/0215527 (2005-09-01), Liotta et al.
patent: 0337713 (1989-10-01), None
patent: 0375329 (1990-06-01), None
patent: 0382526 (1990-08-01), None
patent: 0433898 (1991-06-01), None
patent: 0494119 (1992-07-01), None
patent: 0574487 (1992-09-01), None
patent: 0515144 (1992-11-01), None
patent: 0515156 (1992-11-01), None
patent: 0515157 (1992-11-01), None
patent: 0526253 (1993-02-01), None
patent: WO 90/12023 (1990-10-01), None
patent: WO 91/11186 (1991-08-01), None
patent: WO 92/15308 (1992-09-01), None
patent: WO 92/18517 (1992-10-01), None
patent: WO 92/21676 (1992-12-01), None
Annunziata, R., et al., “Diastereoselective addition of a silylketene acetal to chiral α-thioaldehydes,”Tetrahedron Letters, 1990:6733 (1990).
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,”Biochem. Biophys. Res. Commun., 140(2):735-742 (1986).
Bartlett, P.A., et al., “Asymmetric synthesis via acetal templates. 3. On the stereochemistry observed in the cyclization of chiral acetals of polyolefinic aldehydes: Formation of optimally active homoallylic alcohols,”J. Amer. Chem. Soc., 105:2088-2089 (1983).
Belleau, B., et al., “Design and Activity of a Novel Class of Nucleoside Analogs Effective Against HIV-1,”V Intl. Conf. on AIDS, Montreal, Quebec, Canada, Jun. 4-9, 1989, p. 516, Abstract T.C.0.1.
Borthwick, et al., “Synthesis and enzymatic resolution of carbocyclic 2′-ara-fluoro-guanosine: a potent new anti-herpetic agent,”J. Chem. Soc. Commun., 1988:10656-10658 (1988).
Carter, S.O., et al., “Activities of (-)-Carbovir and 3′-Azido-3′-Deoxythymidine Against Human Immunodeficiency Virus In Vitro,”Antimicrob. Agents Chemother.,, 34(6):1297-1300 (Jun. 1990).
Chang, C.-N. et al., “Deoxycytidine deaminase-resistant stereoisomer is the active form of (±)-2′,3′-dideoxy-3′-thiacytidine in the inhibition of hepatitis B virus replication,”J. Biol. Chem., 267(20): 13938-13942 (1992).
Choi, W.B., et al., “In situ complexation directs the stereochemistry of N-glycosylation in the synthesis of thialanyl and dioxolanyl nucleoside analogs,”J. Am. Chem. Soc., 113(24): 9377-9379 (1991).
Chu, C.K., et al., “A general synthetic method for 2′,3′-dideoxynucleosides: Total synthetic approach,”Nucleosides&Nucleotides, 8(5&6):903-906 (1989).
Chu, C.K., et al., “An efficient total synthesis of 3′-azido-3′-deoxythymidine (AZT) and 3′-azido-2′,3′-dideoxyuridine (AZDDU, CD-87) from D-mannitol,”Tetrahedron Lett., 1988:5349 (1988).
Chu, K.C., 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, K.C., 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).
Connolly, K.J., and Hammer, S.M., “Antiretroviral therapy: reverse transcriptase inhibition,”Antimicrob. Agents Chemother., 36(2):245-254 (Feb. 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,”Molecular 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,”Antimicrob. Agents Chemother., 35(5):801-807 (1991).
Doong, S.-L., et al., “Inhibition of the replication of hepatitis B virus in vitro by 2′,3′-dideoxy-3′-thiacytidine and related analogues,”Proc. Natl. Acad. Sci. USA, 88(919):8495-8499 (Oct. 1, 1991).
Evans, D. A., et al., “New procedure for the direct generation of titanium enolates. Diastereoselective bond constructions with representative examples,”J. Am. Chem. Soc., 112:8215-8216 (1990).
Furman, P.A., et al., “The Anti-Hepatitis B Virus Activities, Cytotoxicities, and Anabolic Profiles of the (−) and (+) Enantiomers ofcis-5-Fluoro-1-{2-(Hydroxymethyl)-1,3-oxathiolane-5-yl}-Cytosine”Antimicrob. Agents Chemother., 36(12):2686-2692 (Dec. 1992).
Herdewijn, P., et al., “Resolution of Aristeromycin Enantiomers,”J. Med. Chem., 28:1385-1386 (1985).
Jeong, L.S., et al., “Asymmetric synthesis and biological evaluation of β-L-(2R,5S)- and α-L-(2R,5R)-1,3-oxathiolane-pyrimidine and -purine nucleosides and potential anti-HIV agents,”J. Med. Chem., 36(2):181-195 (1993).
Katlama, C., et al. (Dept. Infectious Diseases, Hospital Pitla, Salpetriere, Paris, France), “Long term follow-up of patients treated with 3TC for asymptomatic or mildly symptomatic HIV infection,” 6thIntl. Antiviral Symp. (Nice, France), oral presentation Jun. 8, 1994, Abstract C33.
Krenitsky, “An enzymic synthesis of purine D-arabinonucleosides,”Carbohydrate Res., 97:139-146 (1981).
Lin, T.S., et al., “Potent and Selective In Vitro Activity of 3′-Deoxythmindine-2-Ene-(3′-Deoxy-2′,3′-Didehydrothymidine) Against Human Immunodeficiency Virus,”Biochem. Pharm.,36(17):2713-2718 (Sep. 1, 1987).
Mahmoudian, et al., “Enzymatic production of optically pure (1′R-cis)-2-deoxy-3′-thiacytidine (3TC, Lamivudine): a potent anti-HIV agent,”Enzyme Microb. Technol.(Glaxo Group Research Ltd.), 15:749-755 (Sep. 1993).
Merigan, T.C., and Skowron, G., “Safety and tolerance of dideoxycytidine as a single agent. Results of early-phase studies in patients with acquired immunodeficiency syndrome (AIDS) or advanced AIDS-related complex. Study Group of the AIDS Clinical Trials Group of the National Institute of Allergy and Infectious Diseases,”Am. J. Med., 88(5B):11S-15S (May 21, 1990).
Mitsuya, H., et al., “3′-azido-3′-deoxythymidine (BW A 509U):
Choi Woo-Baeg
Liotta Dennis C.
Schinazi Raymond F.
Balasubram Venkataraman
Emory University
King & Spalding
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