Enantiomerically pure .beta.-d-dioxolane nucleosides

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

544276, 544277, C07D47300, A61K 31505

Patent

active

057671222

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: 5011774 (1991-04-01), Farina
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: 5071983 (1991-12-01), Koszalka et al.
patent: 5122517 (1992-06-01), Vince et al.
patent: 5179104 (1993-01-01), Chu 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: 5539116 (1996-07-01), Liotta et al.
Balzarini, J., et al., "Potent and Selective Anti-HTLV-III/LAV Activity of 2',3'-; . . . " Biochemical and Biophysical Research Communications, 140(2):735-742 (1986).
Borthwick, et al., "Synthesis and Enzymatic Resolution of Carbocylic 2'-Ara-Fluoro-Guanosine: A Potent New Anti-Herpetic Agent," J. Chem. Soc. Chem. Commun., vol. 10, pp. 656-658 (1988).
Carter, et al., "Activities of (-)-Carbovir and 3'-Azido-3'-Deoxythymidine Against . . . ," Antimicrobial Agents and Chemotherapy, 34(6):1297-1300 (1990).
Chang, Chien-Neng, et al., "Deoxycytidine Deaminase-resistant Steroisomer . . . ," J. Bio. Chem., 357(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) . . . ," Tetrahedron Lett. 5349 (1988).
Chu, et al., "Comparative Activity of 2',3'-Saturated and Unsaturated Pyrimidine and Purine Nucleosides . . . ," Biochem. Pharm. 37(19):3543-3548 (1988).
Chu, et al., "Structure-Activity Relationships of Pyrimidine Nucleosides as Antiviral Agents . . . ," J. Med. Chem. 32:612 (1989) No. 3.
Cretton, E., et al., "Catabolism of 3'-Azido-3'-Deoxythymidine in Heptaocytes and Liver Microsomes . . . ," Molecuilar Pharmacology, 39:258-266 (1991).
Cretton, E., et al., "Pharmokinetics of 3'-Azido-3'Dexoythymidine . . . ," Antimicrobial Agents and Chemotherapy, 35(5):801-807 (1991).
Furman, et al., "The Anti-Hepatitis B Virus Activities, Cytotoxicities, and Anabolic Profiles . . . ," Antim. Agents and Chemo., 36(12):2686-2692 (1992).
Gerlt, John A., Chemical Abstracts, 107:149790 (1987).
Gosselin, G., "Enantiomeric 2',3'-Deoxycytidine Derivatives are Potent Human Immunodeficiency Virus Inhibitors in Cell Cultures," C.R. Acad. Sci. Paris Sci. Vie. 317:85-89 (1994).
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," Journal of Organic Chem., 57:5563-5565 (1992).
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., vol. 36 (1993) p. 181-195.
Kim, Hea O., et al., "Asymmetric Synthesis of 1,3-Dioxolane-Pyrimidine Nucleosides and Their Anti-HIV Activity," J. Med. Chem., 35:1987-1995 (1992).
Kim, H.O., et al., "L-.beta.-(2S,4S)-and L-.alpha.-(2S,4R)-Dioxolanyl Nucleosides as Potential Anti-HIV Agents: . . . ," 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 . . . ," J.Med.Chem. 1993, 36, 30-37.
Krenitsky, T.A., et al., "3'-Amino-2',3'-Dideoxyribonucleosides of Some Pyrimidines: Synthesis and Biological Activities," J. Med. Chem., 26 (1983) pp. 891-895.
Lee, Bonita, et al., "In Vitro and In Vivo Comparison of the Abilities of Purine and . . . ," Antimicrobial Agents and Chemotherapy, 33(3):336-339 (1989).
Lin, et al., "Potent and Selective In Vitro Activity of 3'-Deoxythmindine-2-Ene-. . . ," Biochem. Pharm., 36(17):2716 (1987).
Mahmoudian, et al., "Enzymatic Production of Optically Pure (2'R-cis)-2;-Deoxy-3'-Tiacytidine (3TC, Lamivudine): A Potent Anti-HIV Agent," Enzyme Microb. Technol., 15:749-755, Glaxo Group Research Ltd., publisher (1993).
Mitsuya, H., et al., "3'-Azido-3'-Deoxythymidine (BW A 509U): An Antiviral Agent that Inhibits . . . ," Proc. Natl. Acad. Sci., USA, 82:7097-7100 (1985).
Mitsuya, H., et al., "Rapid In Vitro Systems for Assessing . . . ," AIDS: Modern Concepts and Therapeutic Challenges, S. Broder, Ed. p. 303, Marcel-Dekker, New York (1987).
Norbeck, D., et al., "A New 2',3'-Dideoxynucleoside Prototype with In Vitro Activity Against HIV," Tetrahedron Lett., pp. 6263-6266 (1989).
Norin, Chemical Abstract, 108:146380 (1987).
Okabe, M., et al., "Synthesis of the Dideoxynucleosides ddC and CNT . . . ," J. Org. Chem., 53(20):4780-4786 (1988).
Ohno, Masaji, Chemical Abstracts, 104:149-258 (1989).
Pirkle, et al., Advances in Chromatography, Giddings, J.C., et al., eds., vol. 27, Chap 3, pp. 73-127, Marcel Dekler, New York (1987).
Richman, D. D., et al., "The Toxicity of Azidothymidine (AZT) in the Treatment of Patients with AIDS . . . , " N. Eng. J. Med., 317:192 (1987).
Saari, Walfred S., et al., "Synthesis and Evaluation of 2-Pyridinone Derivatives as HIV-1-Specific Reverse Transcriptase Inhibitors. 2. Analogues of 3-Aminopyridin-2(1H)-one," J. Med. Chem., 35:3792-3802 (1992).
Satsumabayashi, S. et al., "The Synthesis of 1,3-Oxathiolane-5-one Derivatives," Bull. Chem. Soc. Japan, 45:913 (1972).
Schinazi, R.F., et al., "Activities of the Four Optical Isomers of 2',3'-Dideoxy-3-Thiacytidine . . . ," Antimic. Agents & Chemo. 36(3):672-676 (1992).
Schinazi, R.F., et al., "Insights into HIV Chemotherapy," AIDS Research and Human Retroviruses 8(6):963-990 (1992).
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 . . . ," Antim. Agents and Chemo. 36(11):2423-2431 (1992).
Schinazi, R.F., et al., "Gubstrate Specificity of Escherichia Coli Thymidine Phosphorylase for Pyrimidine . . . ," Bioch. Pharm. 44(2):199-204 (1992).
Secrist, et al., "Resolution of Racemic Carbocyclic Analogues of Purine Nucleosides Through the Action of Adenosine Deaminase. Antiviral Activity of the Carbocyclic 2'-Deoxyguanosine Enantiomers," J. Med. Chem., 30:746-749 (1987).
Storer, R., et al., "The Resolution and Absolute Sterochemistry of the Enantiomeris of cis-1-2-(Hydromethyl)-1,3-Oxathiolan-5-yl)cytosine . . . ," Nucleosides & Nucleotides, 12(2):225-236 (1993).
Vorbruggen, et al, "Nucleoside Synthesis with Trimethysilyl Triflate and Perchlorate as Catalysts," Chem. Ber., 114:1234-1255 (1981).
Wilson, L.J., et al., "The Synthesis and Anti-HIV Activity of Pyrimidine Dioxolanyl Nucleosides," Bioorganic & Medicinal Chemistry Letters, 3(2):169-174 (1993).
Wilson, L.J., et al., "A General Method for Controlling Glycosylation Stereochemistry in the Synthesis . . . ," Tetrahedron Lett., 31(13):1815-1818 (1990).
Zhu, Zhou, et al., "Cellular Metabolism of 3'-Azido-2',3'-Dideoxyuridine with Formation of 5'-O-Diphoposhexase . . . " Molecular Pharmacology, 38:929-938 (1990).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Enantiomerically pure .beta.-d-dioxolane nucleosides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Enantiomerically pure .beta.-d-dioxolane nucleosides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Enantiomerically pure .beta.-d-dioxolane nucleosides will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1726321

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.