TAK-79. Anti-HIV chemokine CCR5 antagonist

Drugs of the Future

Volumn 25, Issue 3, 2000, Pages 252-258

  Kanzaki, N ^a   Shiraishi, M ^b   Iizawa, Y ^b   Baba, M ^b   Nishimura, O ^b   Fujino, M ^b  

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; N [4 [[[6,7 DIHYDRO 2 (4 METHYLPHENYL) 5H BENZOCYCLOHEPTEN 8 YL]CARBONYL]AMINO]BENZYL] N,N DIMETHYL 2H TETRAHYDROPYRAN 4 AMINIUM CHLORIDE; N,N DIMETHYL N [4[[[2 (4 METHYLPHENYL) 6,7 DIHYDRO 5H BENZOCYCLOHEPTEN 8 YL]CARBONYL]AMINO]BENZYL]TETRAHYDRO 2H PYRAN 4 AMINIUM CHLORIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; DRUG INHIBITION; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; NONHUMAN; REVIEW; VIRUS REPLICATION;

EID: 0034049303     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.2000.025.03.568833     Document Type: Review

References (30)

1. Shiraishi, M., Kitayoshi, T., Aramaki, Y., Honda, S., Oda, T. (Takeda Chemical Industries, Ltd.). Anilide deriv., production and use thereof. JP1999263764, WO 9932468.
2. Nishimura, O., Baba, M., Sawada, H., Kanzaki, N., Kuroshima, K., Shiraishi, M., Aramaki, Y. (Takeda Chemical Industries, Ltd.). Pharmaceutical composition for antagonizing CCR5 comprising anilide derivative. WO 9932100.
3. Shiraishi, M., Aramaki, Y., Seto, M. et al. TAK-779, a small molecule CCR5 antagonist: Design, synthesis, and in vitro activity of anilide derivatives. 19th Intersci Conf Antimicrob Agents Chemother (Sept 26-29, San Francisco) 1999, Abst F911.
4. Shiraishi, M., Aramaki, Y., Seto, M. et al. Discovery of small molecule CCR5 antagonists. 19th Symp Med Chem and 8th Annu Meet Div Med Chem Jpn (Nov 17-19, Tokyo) 1999, Abst 2P-06.
5. Shiraishi, M., Aramaki, Y., Seto, M. et al. Discovery of novel, potent and selective small molecule CCR5 antagonists as anti-HIV agents: Synthesis and biological evaluation of anilide derivatives with a quaternary ammonium moiety. J Med Chem, submitted.
6. Havlir, D.V., Richman, D.D. Viral dynamics of HIV: Implications for drug development and therapeutic strategies. Ann Intern Med 1996, 124: 984-94.
7. Carpenter, C.C.J., Fischl, M.A., Hammer, S.M. et al. Antiretroviral therapy for HIV infection in 1998: Updated recommendations of the International AIDS Society-USA Panel. JAMA - J Am Med Assoc 1998, 280: 78-86.
8. Deeks, S.G., Smith, M., Holodniy, M., Kahn, J.O, HIV-1 protease inhibitors. A review for clinicians. JAMA - J Am Med Assoc 1997, 277: 145-53.
9. Deng, H., Liu, R., Ellmeier, W. et al. Identification of a major co-receptor for primary isolates of HIV-1. Nature 1996, 381: 661-6.
10. Dragic, T., Litwin, V., Allaway, G.P. et al. HIV-1 entry into CD4+ cells is mediated by the chemokine receptor CC-CKR-5. Nature 1996, 381: 667-73.
11. Alkhatib, G., Combadiere, C., Broder, C.C., Feng, Y., Kennedy, P.E., Murphy, P.M., Berger, E.A. CC CKR5: A RANTES, MIP-1α, MIP-1β receptor as a fusion cofactor for macrophage-tropic HIV-1. Science 1996, 272: 1955-8.
12. Choe, H., Farzan, M., Sun, Y. et al. The β-chemokine receptors CCR3 and CCR5 facilitate infection by primary HIV-1 isolates. Cell 1996, 85: 1135-48.
13. Doranz, B.J., Rucker, J., Yi, Y. et al. A dual-tropic primary HIV-1 isolate that uses tusin and the β-chemokine receptors CKR-5, CKR-3, and CKR-2b as fusion cofactors. Cell 1996, 85: 1149-58.
14. Schuitemaker, H., Koot, M., Kootstra, N.A. et al. Biological phenotype of human immunodeficiency virus type 1 clones at different stages of infection: Progression of disease is associated with a shift from monocytotropic to T-cell-tropic virus population. J Virol 1992, 66: 1354-60.
15. Richman, D.D., Bozzette, S.A. The impact of the syncytium-inducing phenotype of human immunodeficiency virus on disease progression. J Infect Dis 1994, 169: 968-74.
16. Connor, R.I., Sheridan, K.E., Caradini, D., Choe, S., Landau, N.L. Change in coreceptor use correlates with disease progression in HIV-1-infected individuals. J Exp Med 1997, 185: 621-8.
17. Liu, R., Paxton, W.A., Choe, S. et al. Homozygous defect in HIV-1 coreceptor accounts for resistance of some multiply -exposed individuals to HIV-1 infection. Cell 1996, 86: 367-77.
18. Samson, M., Libert, F., Doranz, B.J. et al. Resistance to HIV-1 infection in caucasian individuals bearing mutant alleles of the CCR-5 chemokine receptor gene. Nature 1996, 382: 722-5.
19. Bjorndal, A., Deng, H., Jansson, M. et al. Coreceptor usage of primary human immunodeficiency virus type 1 isolates varies according to biological phenotype. J Virol 1997, 71: 7478-87.
20. Scarlatti, G., Tresoldi, E., Bjorndal, A. et al. In vivo evolution of HIV-1 co-receptor usage and sensitivity to chemokine-mediated suppression. Nat Med 1997, 3: 1259-65.
21. Cocchi, F., DeVico, A.L., Garzino-Demo, A., Arya, S.K., Gallo, R.C., Lusso, P. Identification of RANTES, MIP-1α, and MIP-1β as the major HIV-suppressive factors produced by CD8+ T cells. Science 1995, 270: 1811-5.
22. Proudfoot, A.E.I., Power, C.A., Hoogewerf, A.J., Montjovent, M.O., Borlat, F., Offord, R.E., Wells, T.N.C. Extension of recombinant human RANTES by the retention of the initiating methionine produces a potent antagonist. J Biol Chem 1996, 271: 2599-603.
23. Simmons, G., Clapham, P.R., Picard, L. et al. Potent inhibition of HIV-1 infectivity in macrophages and lymphocytes by a novel CCR5 antagonist. Science 1997, 276: 276-9.
24. Baba, M., Nishimura, O., Kanzaki, N. et al. A small-molecule, nonpeptide CCR5 antagonist with highly potent and selective anti-HIV-1 activity. Proc Natl Acad Sci USA 1999, 96: 5698-703.
25. Raport, C.J., Gosling, J., Schweickart, V.L., Gray, P.W., Charo, I. F. Molecular cloning and functional characterization of a novel human CC chemokine receptor (CCR5) for RANTES, MIP-1β, and MIP-1α. J Biol Chem 1996, 271: 17161-6.
26. Schols, D., Struyf, S., Van Damme, J., Esté, J.A., Henson, G., De Clercq, E. Inhibition of T-tropic HIV strains by selective antagonization of the chemokine receptor CXCR4. J Exp Med 1997, 186: 1383-8.
27. Donzella, G.A., Schols, D., Lin, S.W., Esté, JA, Nagashima, K.A., Maddon, P.J., Allaway, G.P., Sakmar, T.P., Henson, G., De Clercq, E., Moore, J.P. AMD3100, a small molecule inhibitor of HIV-1 entry via the CXCR4 co-receptor. Nat Med 1998, 4: 72-7.
28. Lee, B., Sharron, M., Blanpain C. et al. Epitope mapping of CCR5 reveals multiple conformational states and distinct but overlapping structures involved in chemokine and coreceptor function. J Biol Chem 1999, 274: 9617-26.
29. Sicillano, S.J., Kuhmann, S. E., Weng, Y. et al. A critical site in the core of the CCR5 chemokine receptor required for binding and infectivity of human immunodeficiency virus type 1. J Biol Chem 1999, 274: 1905-13.
30. Mack, M., Luckow, B., Nelson, P.J. et al. Aminooxypentane-RANTES induces CCR5 internalization but inhibits recycling: A novel inhibitory mechanism of HIV infectivity. J Exp Med 1998, 187: 1215-24.