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Identification and Efficient Synthetic Method for Preparation of Cyclopentane-1,3-diol Impurity in Tafluprost Drug
Corresponding Author(s) : Muvvala Venkatanarayana
Asian Journal of Chemistry,
Vol. 33 No. 1 (2021): Vol 33 Issue 1
Abstract
In present work, the isolation, synthesis and characterization of the identified triol impurity present in tafluprost is described. This investigation helps to avoid formation of impurity by control the reaction and its leads to improving high yields of tafluprost. The source of impurity was identified, due to over-reduction of lactone with diisobutyl aluminum hydride (DIBAL-H).
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- G.E. Arth, J. Am. Chem. Soc., 75, 2413 (1953); https://doi.org/10.1021/ja01106a040
- R. Bloch and L. Gilbert, J. Org. Chem., 52, 4603 (1987); https://doi.org/10.1021/jo00229a031
- X.J. Zhang, T.B. Lai and R.Y.C. Kong, ed: I. Horváth, Biology of Fluoro-Organic Compounds, In: Fluorous Chemistry, Springer: Berlin, Heidelberg, vol. 308, p. 365 (2011).
- N. Gupta and Y.H. Yucel, Curr. Opin. Ophthalmol., 18, 110 (2007); https://doi.org/10.1097/ICU.0b013e3280895aea
- K. Abhijeet, J.R. Sarkar, K. Uday, P.K. Udayan, A.K. Roy and R.K.P. Chaudhary, Indian Dermatol. Online J., 9, 224 (2018).
- R. Andrea, P. Teodoro, N. Federico and Q. Luciano, Clin. Ophthalmol.,2, 897 (2008).
- G.M. Keating, Clin. Drug Investig., 36, 499 (2016); https://doi.org/10.1007/s40261-016-0413-z
- Y. Kuwayama and S. Komemushi, Nippon Ganka Gakkai Zasshi, 114,436 (2010) (In Japanese).
- A. Sutton, P. Gouws and A. Ropo, Int. J. Clin. Pharmacol. Ther., 46,400 (2008); https://doi.org/10.5414/CPP46400
- Y. Matsumura, N. Mori, T. Nakano, H. Sasakura, T. Matsugi, H. Hara and Y. Morizawa, Tetrahedron Lett., 45, 1527 (2004); https://doi.org/10.1016/j.tetlet.2003.12.029
- Guidance on Impurities Testing: Impurities in New Drug Substances, CPMP/ICH2737/99.ICH revision of CPMP/ICH/142/95 CPMP/ICH 2737/99 (2002).
References
G.E. Arth, J. Am. Chem. Soc., 75, 2413 (1953); https://doi.org/10.1021/ja01106a040
R. Bloch and L. Gilbert, J. Org. Chem., 52, 4603 (1987); https://doi.org/10.1021/jo00229a031
X.J. Zhang, T.B. Lai and R.Y.C. Kong, ed: I. Horváth, Biology of Fluoro-Organic Compounds, In: Fluorous Chemistry, Springer: Berlin, Heidelberg, vol. 308, p. 365 (2011).
N. Gupta and Y.H. Yucel, Curr. Opin. Ophthalmol., 18, 110 (2007); https://doi.org/10.1097/ICU.0b013e3280895aea
K. Abhijeet, J.R. Sarkar, K. Uday, P.K. Udayan, A.K. Roy and R.K.P. Chaudhary, Indian Dermatol. Online J., 9, 224 (2018).
R. Andrea, P. Teodoro, N. Federico and Q. Luciano, Clin. Ophthalmol.,2, 897 (2008).
G.M. Keating, Clin. Drug Investig., 36, 499 (2016); https://doi.org/10.1007/s40261-016-0413-z
Y. Kuwayama and S. Komemushi, Nippon Ganka Gakkai Zasshi, 114,436 (2010) (In Japanese).
A. Sutton, P. Gouws and A. Ropo, Int. J. Clin. Pharmacol. Ther., 46,400 (2008); https://doi.org/10.5414/CPP46400
Y. Matsumura, N. Mori, T. Nakano, H. Sasakura, T. Matsugi, H. Hara and Y. Morizawa, Tetrahedron Lett., 45, 1527 (2004); https://doi.org/10.1016/j.tetlet.2003.12.029
Guidance on Impurities Testing: Impurities in New Drug Substances, CPMP/ICH2737/99.ICH revision of CPMP/ICH/142/95 CPMP/ICH 2737/99 (2002).