Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Patent
1995-06-07
1999-06-22
Ford, John M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
544317, 544310, 544313, 544229, C07D23934, C07D23936, C07D23954
Patent
active
059144009
ABSTRACT:
The present invention relates to a method of preparing BCH-189 and various analogs of BCH-189 from inexpensive precursors with the option of introducing functionality as needed. This synthetic route allows the stereoselective preparation of the biologically active isomer of these compounds, .beta.-BCH-189 and related compounds. Furthermore, the steochemistry at the nucleoside 4' position can be controlled to produce enantiomerically-enriched .beta.-BCH-189 and its analogs.
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 Clerq et al.
patent: 5011774 (1991-04-01), Farina et al.
patent: 5041449 (1991-08-01), Belleau et al.
patent: 5059690 (1991-10-01), Zahler et al.
patent: 5204466 (1993-04-01), Liotta et al.
patent: 5539116 (1996-07-01), Liotta et al.
Balzarini, J., et al., Biochemical and Biophysical Research Communications, vol. 140, No. 2, pp. 735-742 (1986).
Bartlett, P.A., J. Am. Chem. Soc. 1983, 105:2088.
Belleau, B., et al., "Design and Activity of a Novel Class of Nucleoside 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 Stereoisomer Is the Active Form of (+)-2',3'-Didedoxy-3'-thiacytidine in the Inhibition of Hepatitis B Virus Replication," The Journal of Biological Chemistry, vol. 357, No. 20, pp. 13938-13942 (1992).
Chem. Ber., 114:1244 (1981).
Chu, C.K., Nucleosides & Nucleotides, 1989, 8:903.
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'-Deoxythiamidine (AZT) and 3'-Azido-2',3'-Dideoxyuridine (AZDDU, CS-87) from D-Mannitol, Tetrahedron Letters, 1988, p. 5349.
Cretton, E., et al., "Pharmakinetics of 3'-Azido-3'-Deoxythymidine and its Catabolites and Interactions with Probenecid in Rhesus Monkeys," Antimicrobial Agents and Chemotherapy, pp. 801-807 (1991).
Evans, D.A. et al. J. Am. Chem. Soc., 1990, 112:8215.
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 (1992).
Hoong, et al., Journal of Organic Chemistry, 1992, vol. 57, pp. 5563-5565.
Lin, et al., "Potent and Selective In Vitro Activity of 3'-Deoxythyminidin-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, H. et al., Proc. Natl. Acad. Sci. USA, vol. 82, pp. 7097-7100 (1985).
Mitsuya, H. et al., "Molecular Targets for AIDS Therapy," Science, vol. 249, pp. 1533-1544 (1990).
Nicolaou, K.C., J. Am. Chem. Soc., 1986, 108:2466.
Norbeck, D., et al., "A New 2',3'-Dideoxynucleoside Prototype with an In Vitro Activity Against HIV," Tetrahedron Lett. (1989),p. 6263.
Okabe, M. et al., "Synthesis of the Dideoxynucleosides ddC and CNT from Glutamic Acid, Ribonolactone, and Pyrimidine Bases," J. Org. Chem., 1989,53:4780.
Richman, 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.
Stasumabayashi, S. et al., "The Synthesis of 1,3-Oxathiolan-5-one Derivatives," Bull. Chem. Soc. Japan, 1972, 45, 913.
Schinazi, R.F. et al., Antimicrobial Agents and Chemotherapy 36(3) pp.672-676 (1992).
Schinazi, R.F. et al., "Insights into HIV Chemotherapy," AIDS Research and Human Retroviruses 8(6) (1992)pp. 963-990.
Schinazi, R.F. et al., Antimicrobial Agents and Chemotherapy, 36(11)pp. 2432-2438 (1992).
Schinazi, R.F. et al., "Substrate Specificity of Escherichia coli Thymidine Phosphorylase for Pyrimidine Nucleoside with and Anti-Human Immunodeficiency Virus Activity," Biochemical Pharmacology 44(2) (1992) 199-204.
Storer, Richard, et al., Nucleosides & Nucleotides, 12(2), 225-236 (1993).
Takano, A., et al., Chemistry Letters, 1983, p. 1593.
Vorbruggen et al., "Nucleoside Synthesis with Trimethysilyl 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, p. 1815.
Winslow, Dean L. et al., AIDS, vol. 8, No. 6, pp. 753-755 (1994).
Zhu, Zhou, et al., Molecular Pharmacology, vol. 38, pp. 929-938 (1990).
Choi Woo-Baeg
Liotta Dennis C.
Emory University
Ford John M.
Haley Jacqueline
Knowles Sherry M.
LandOfFree
Method and compositions for the synthesis of BCH-189 and related does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Method and compositions for the synthesis of BCH-189 and related, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method and compositions for the synthesis of BCH-189 and related will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1708821