New Method of Palladium Metal Trapping through Resins in Antiviral Drug: Valacyclovir HCl
Author(s)
Keshava Navin Kumar Reddy,
Murugulla Adharvana Chari*,
Mayur D. Khunt,
V. V. N. K. V. Prasada Raju,
Bojja Ramachandra Reddy,
Vurimidi Himabindu,
Ghanta Mahesh Reddy
Affiliation(s)
Research and Development, Integrated Product Development, Innovation Plaza, Dr. Reddy’s Laboratories Ltd., Bachupally, Quthubullapur, India. Dr. MACS Bio-Pharma Pvt. Ltd., Western Hills, Kukatpally, Hyderabad, India. Department of Chemistry, Institute of Science and Technology, J. N. T. University, Kukatpally, Hyderabad, India.
Research and Development, Integrated Product Development, Innovation Plaza, Dr. Reddy’s Laboratories Ltd., Bachupally, Quthubullapur, India. Dr. MACS Bio-Pharma Pvt. Ltd., Western Hills, Kukatpally, Hyderabad, India. Department of Chemistry, Institute of Science and Technology, J. N. T. University, Kukatpally, Hyderabad, India.
ABSTRACT
This process describes a novel technique for effective trapping of “Pd” metal through resins during the process development of L-valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl) methoxy] ethyl ester, and mono hydrochloride known as a Valacyclovir hydrochloride (1). This technique is suitable for large-scale production of 1 and it is described here Pd metal trapping by using different resins.
Cite this paper
K. Reddy, M. Chari, M. Khunt, V. Raju, B. Reddy, V. Himabindu and G. Reddy, "New Method of Palladium Metal Trapping through Resins in Antiviral Drug: Valacyclovir HCl," International Journal of Organic Chemistry, Vol. 3 No. 4, 2013, pp. 251-255. doi: 10.4236/ijoc.2013.34036.
K. Reddy, M. Chari, M. Khunt, V. Raju, B. Reddy, V. Himabindu and G. Reddy, "New Method of Palladium Metal Trapping through Resins in Antiviral Drug: Valacyclovir HCl," International Journal of Organic Chemistry, Vol. 3 No. 4, 2013, pp. 251-255. doi: 10.4236/ijoc.2013.34036.
References
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[1] L. M. Beauchamp, G. F. Orr, P. de Miranda, T. Brunette and T. A. Krenitsky, “Amino Acid Ester Prodrugs of Acyclovir,” Antiviral Chemistry and Chemotherapy, Vol. 3, No. 3, 1992, pp. 157-164. [2] R. J. Crooks and A. Murray, Antiviral Chemistry & Chemotherapy, Vol. 5, No. S1, 1994, pp. 31-37. [3] C. M. Perry and D. Faulds, “Valacyclovir,” Drugs, Vol. 52, No. 5, 1996, pp. 754-772.
http://dx.doi.org/10.2165/00003495-199652050-00009 [4] L. H. Wang, M. Schultz, S. Weller, M. L. Smiley and M. R. Blu, “Valacyclovir Compared with Acyclovir for Improved Therapy for Herpes Zoster in Immunocompetent Adults,” Antimicrobial Agents and Chemotherapy, Vol. 39, No. 7, 1995, pp. 1546-1553.
http://dx.doi.org/10.1128/AAC.39.7.1546 [5] D.-K. Kim, N. Lee, G. J. Im, H.-T. Kim and H. K. Key, “Synthesis and Evaluation of 2-Amino-6-fluoro-9-(2-hydroxyethoxymethyl) Purine Esters as Potential Prodrugs of Acyclovir,” Bioorganic & Medicinal Chemistry, Vol. 6, 1998, pp. 2525-2530.
http://dx.doi.org/10.1016/S0968-0896(98)80026-6 [6] A. S. Jadhav, D. B. Pathare and M. S. Shingare, “Development and Validation of Enantioselective High Performance Liquid Chromatographic Method for Valacyclovir, an Antiviral Drug in drug Substance,” Journal of Pharmaceutical and Biomedical Analysis, Vol. 43, No. 4, 2007, pp. 1568-1572.
http://dx.doi.org/10.1016/j.jpba.2006.11.018 [7] J. Soul-Lawton, E. Seaber, N. On, R. Wootton, P. Rolan and J. Posner, “Absolute Bioavailability and Metabolic Disposition of Valacyclovir, the L-valyl Ester of Acyclovir, Following Oral Administration to Humans,” Antimicrobial Agents and Chemotherapy, Vol. 39, No. 12, 1995, p. 2759. [8] L. M. Beauchamp and N. C. Raleigh, “Synthesis of Amino Acid Esters and Pharmaceutical Acceptable Salts and Treatment of Viral Infections,” US Patent No. 4957924. [9] W. P. Bieger, et al., “Immunotoxocolgy of Metals,” Zur Deutshcen Auszahe, 1996. [10] K. Bonnig, et al., “Quantitative Analysis of the Corrosion rates of Palladium Alloys,” Dtsche Azhnarztliche Zeitschrift, Vol. 45, No. 8, 1990, pp. 508-510. [11] Y. Kawata, et al., “Cytotoxicity of Pd-Co Dental Alloys,” Journal of Dental Research, Vol. 60, No. 8, 1981, pp. 1403-1409.
http://dx.doi.org/10.1177/00220345810600080301 [12] T. Z. Liu, et al., “Palladium Exacerbates Hydroxyl Radical Mediated DNA Damage,” Free Radical Biology and Medicine, Vol. 23, No. 1, 1997, pp. 155-161.
http://dx.doi.org/10.1016/S0891-5849(96)00553-9 [13] C. K. Pillai, et al., “Interaction of Palladium with DNA,” Biochimica et Biophysica Acta, Vol. 474, No. 1, 1977, pp. 11-16. http://dx.doi.org/10.1016/0005-2787(77)90209-X [14] G. M. Kolesova, et al., “Effect of Palladium Compounds on Mitrochondrial Enzymatic Systems,” Voprosy Meditsinskoi Khimii, Vol. 25, No. 5, 1979, pp. 537-540. [15] J. D. Spikes, et al., “Enzyme Inhibition by Palladium,” Biochemical and Biophysical Research Communications, Vol. 35, No. 3, 1969, pp. 420-422.
http://dx.doi.org/10.1016/0006-291X(69)90516-6 [16] M. D. Shultz, et al., “Palladium—A New Inhibitor of Cellulase Enzyme Activity,” Biochemical and Biophysical Research Communications, Vol. 209, No. 3, 1995, pp. 1046-1052. http://dx.doi.org/10.1006/bbrc.1995.1603 [17] A. M. Al-Roubaie, “Condition of the Periodontion of Teeth with Silver-Palladium Bridge,” Fogorvosi Szemle, Vol. 79, No. 7, 1986, pp. 207-212. [18] D. Downey, “Contact Mucositis Due to Palladium,” Contact Dermatitis, Vol. 21, No. 1, 1989, p. 54.
http://dx.doi.org/10.1111/j.1600-0536.1989.tb04688.x [19] J. A. Marcusson, “Contact Allergies to Palladium Chloride,” Contact Dermatitis, Vol. 34, No. 5, 1996, pp. 320323.
http://dx.doi.org/10.1111/j.1600-0536.1996.tb02215.x [20] J. Vilaplana, C. Romaguera and F. Cornellana, “Contact Dermatitis and Adverse Oral Mucous Membrane Reactions Related to the Use of Dental Prostheses,” Contact Dermatitis, Vol. 30, No. 2, 1994, pp. 80-84. [21] A. Henston-Pettersen, “Casting Alloy Side Effects,” Advances in Dental Research, Vol. 6, No. 1, 1992, pp. 38-43.