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Synthesis and Characterization of Novel Analogues of Lopinavir
Corresponding Author(s) : Peketi Rajesh Reddy
Asian Journal of Chemistry,
Vol. 33 No. 1 (2021): Vol 33 Issue 1
Abstract
The present work describes the identification, origin, synthesis, characterization and control of four novel analogues of lopinavir viz. leucine analogue of lopinavir, isoleucine analogue of lopinavir, methyl analogue of lopinavir and dihydroxy analogue of lopinavir.
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- A. Chandwani and J. Shuter, Ther. Clin. Risk Manag., 4, 1023 (2008); https://doi.org/10.2147/tcrm.s3285
- C. Flexner, N. Engl. J. Med., 338, 1281 (1998); https://doi.org/10.1056/NEJM199804303381808
- International Conference on Harmonization (ICH) Guidelines. Q3A (R) Impurities in New Drug Substances, ICH Guidelines: Geneva, Switzerland (2002).
- International Conference on Harmonization (ICH) Guidelines, Q2B Validation of Analytical Procedure: Methodology, ICH Guidelines: Geneva, Switzerland (1996).
- H.L. Sham, D.A. Betebenner, T. Herrin, G. Kumar, S. Vasavanonda, A. Saldivar, A. Molla, D.J. Kempf, J.J. Plattner and W. Norbeck, Bioorg.Med. Chem. Lett., 11, 1351 (2001); https://doi.org/10.1016/S0960-894X(01)00243-8
- S.R. Chitturi, Ch. Bharathi, A.V. Reddy, K.C. Reddy, H.K. Sharma, V.K. Handa, R. Dandala and V.H. Bindu, J. Pharm. Biomed. Anal., 48,1430 (2008); https://doi.org/10.1016/j.jpba.2008.09.015
- H.L. Sham, C. Zhao, L. Li, D.A. Betebenner, S. Vasavanonda, D.J.Kempf, A. Saldivar, J.J. Plattner and D.W. Norbeck, Bioorg. Med. Chem.Lett., 12, 3101 (2002); https://doi.org/10.1016/S0960-894X(02)00643-1
- H.L. Sham, D.A. Betebenner, X. Chen, A. Saldivar, S. Vasavanonda, D.J. Kempf, J.J. Plattner and D.W. Norbeck, Bioorg. Med. Chem. Lett.,12, 1185 (2002); https://doi.org/10.1016/S0960-894X(02)00134-8
- A.V. Raghava Reddy, Sci. Pharm., 83, 49 (2015); https://doi.org/10.3797/scipharm.1407-14
- H.L. Sham, D.A. Betebenner, W. Rosenbrook, T. Herrin, A. Saldivar, S. Vasavanonda, J.J. Plattner and D.W. Norbeck, Bioorg. Med. Chem. Lett.,14, 2643 (2004); https://doi.org/10.1016/j.bmcl.2004.02.089
- A.S. Lakshmi Devi, Y.S. Rao, Y. Suresh, M.Y. Reddy, G. Jyothi, B. Rajababu, V.S. Prasad and V.U. Rao, Magn. Reson. Chem., 45, 424 (2007); https://doi.org/10.1002/mrc.1968
- U. Seshachalam, B. Haribabu and K. Chandrasekhar, Biomed. Chromatogr., 21, 716 (2007); https://doi.org/10.1002/bmc.810
- V.R.R. Ambati, S. Garaga, R. Dandala and S. Meenakshisunderam, Process for the Preparation of Substantially Pure (2S,3S,5S)-5-Amino2-N,N-dibenzylamino-3-hydroxy-1,6-diphenylhexane, US Patent No 8236991B (2007).
- E.J. Stoner, A.J. Cooper, D.A. Dickman, L. Kolacz Kowski, J.E. Lallaman, J.H. Liu, P.A. Oliver-Shaffer, K.M. Patel, J.B. Paterson, D.J. Plata, D.A. Riley, H.L. Sham, P.J. Stengel and J.H. Tien, Org. Process Res. Dev., 4, 264 (2000);https://doi.org/10.1021/op990202j
- H.L. Sham, D.W. Norbeck, X. Chen and D.A. Betebenner, Retroviral Protease Inhibiting Compounds, US Patent 5,914,332 (1995).
- E. Ramu and B.V. Rao, Tetrahedron Asymm., 20, 2201 (2009); https://doi.org/10.1016/j.tetasy.2009.09.003
References
A. Chandwani and J. Shuter, Ther. Clin. Risk Manag., 4, 1023 (2008); https://doi.org/10.2147/tcrm.s3285
C. Flexner, N. Engl. J. Med., 338, 1281 (1998); https://doi.org/10.1056/NEJM199804303381808
International Conference on Harmonization (ICH) Guidelines. Q3A (R) Impurities in New Drug Substances, ICH Guidelines: Geneva, Switzerland (2002).
International Conference on Harmonization (ICH) Guidelines, Q2B Validation of Analytical Procedure: Methodology, ICH Guidelines: Geneva, Switzerland (1996).
H.L. Sham, D.A. Betebenner, T. Herrin, G. Kumar, S. Vasavanonda, A. Saldivar, A. Molla, D.J. Kempf, J.J. Plattner and W. Norbeck, Bioorg.Med. Chem. Lett., 11, 1351 (2001); https://doi.org/10.1016/S0960-894X(01)00243-8
S.R. Chitturi, Ch. Bharathi, A.V. Reddy, K.C. Reddy, H.K. Sharma, V.K. Handa, R. Dandala and V.H. Bindu, J. Pharm. Biomed. Anal., 48,1430 (2008); https://doi.org/10.1016/j.jpba.2008.09.015
H.L. Sham, C. Zhao, L. Li, D.A. Betebenner, S. Vasavanonda, D.J.Kempf, A. Saldivar, J.J. Plattner and D.W. Norbeck, Bioorg. Med. Chem.Lett., 12, 3101 (2002); https://doi.org/10.1016/S0960-894X(02)00643-1
H.L. Sham, D.A. Betebenner, X. Chen, A. Saldivar, S. Vasavanonda, D.J. Kempf, J.J. Plattner and D.W. Norbeck, Bioorg. Med. Chem. Lett.,12, 1185 (2002); https://doi.org/10.1016/S0960-894X(02)00134-8
A.V. Raghava Reddy, Sci. Pharm., 83, 49 (2015); https://doi.org/10.3797/scipharm.1407-14
H.L. Sham, D.A. Betebenner, W. Rosenbrook, T. Herrin, A. Saldivar, S. Vasavanonda, J.J. Plattner and D.W. Norbeck, Bioorg. Med. Chem. Lett.,14, 2643 (2004); https://doi.org/10.1016/j.bmcl.2004.02.089
A.S. Lakshmi Devi, Y.S. Rao, Y. Suresh, M.Y. Reddy, G. Jyothi, B. Rajababu, V.S. Prasad and V.U. Rao, Magn. Reson. Chem., 45, 424 (2007); https://doi.org/10.1002/mrc.1968
U. Seshachalam, B. Haribabu and K. Chandrasekhar, Biomed. Chromatogr., 21, 716 (2007); https://doi.org/10.1002/bmc.810
V.R.R. Ambati, S. Garaga, R. Dandala and S. Meenakshisunderam, Process for the Preparation of Substantially Pure (2S,3S,5S)-5-Amino2-N,N-dibenzylamino-3-hydroxy-1,6-diphenylhexane, US Patent No 8236991B (2007).
E.J. Stoner, A.J. Cooper, D.A. Dickman, L. Kolacz Kowski, J.E. Lallaman, J.H. Liu, P.A. Oliver-Shaffer, K.M. Patel, J.B. Paterson, D.J. Plata, D.A. Riley, H.L. Sham, P.J. Stengel and J.H. Tien, Org. Process Res. Dev., 4, 264 (2000);https://doi.org/10.1021/op990202j
H.L. Sham, D.W. Norbeck, X. Chen and D.A. Betebenner, Retroviral Protease Inhibiting Compounds, US Patent 5,914,332 (1995).
E. Ramu and B.V. Rao, Tetrahedron Asymm., 20, 2201 (2009); https://doi.org/10.1016/j.tetasy.2009.09.003