Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 18
466
Views
5
CrossRef citations to date
0
Altmetric
Articles

An improved synthesis of latanoprost involving effective control on 15(S) diastereomer

, , , &
Pages 2350-2356 | Received 31 Mar 2019, Published online: 16 Jul 2019

References

  • Alexander, C. L.; Miller, S. J.; Abel, S. R. Prostaglandin Analog Treatment of Glaucoma and Ocular Hypertension. Ann. Pharmacother. 2002, 36, 504–511. doi: 10.1345/aph.1A178.
  • Collins, P. W.; Djuric, S. W. Synthesis of Therapeutically Useful Prostaglandin and Prostacyclin Analogs. Chem. Rev. 1993, 93, 1533. doi: 10.1021/cr00020a007.
  • Russo, A.; Riva, I.; Pizzolante, T.; Noto, F.; Quaranta, L. Latanoprost Ophthalmic Solution in the Treatment of Open Angle Glaucoma or Raised Intraocular Pressure: A Review. Clin. Ophthalmol. 2008, 2, 897–905. doi: 10.2147/OPTH.S3228.
  • (a) Prévost, S.; Thai, K.; Schützenmeister, N.; Coulthard, G.; Erb, W.; Aggarwal, V. K. Synthesis of Prostaglandin Analogues, Latanoprost and Bimatoprost, Using Organocatalysis via a Key Bicyclic Enal Intermediate. Org. Lett. 2015, 17, 504–507. (b) Corey, E. J.; Weinshenker, N. M.; Schaaf, T. K.; Huber, W. Stereo-Controlled Synthesis of dl-Prostaglandins F2.alpha and E2. J. Am. Chem. Soc. 1969, 91, 5675. doi: 10.1021/ja01030a077. (c) Vijendhar, K.; Srinivas, B.; Boodida, S. A Facile and Efficient Synthesis of (15R)-Latanoprost from Chiral Precursor Corey Lactone Diol. J. Chem. Sci. 2015, 127, 2023–2028. doi:10.1007/s12039-015-0963-2. (d) Stjernschantz, J.; Bahram, R. 5-Oxa Prostaglandin F2.sub.α Analogs. US 5,223,537, Jan. 29, 1993. (e) Hellberg, M. R.; Dean, T. R.; Zinke, P. W.; Selliah, R. D.; Bishop, J. E. Use of 9-Deoxy Prostaglandin Derivatives to Treat Glaucoma. US 5,698,733, Dec. 16, 1997. (f) Gutman, A.; Nisnevich, G.; Etinger, M.; Zaltzman, I.; Yudovich, L.; Pertsikov, B.; Tishin, B. Process for the Preparation of Prostaglandin Derivatives. US 7,166,730, Jan. 23, 2007.
  • (a) Resul, B. Method for Synthesis of Prostaglandin Derivatives. US5359095, Oct. 25, 1994. (b) Gutman, A.; Nisnevich, G. A New Process for the Preparation of Latanoprost. WO0155101A2, Aug. 02, 2001. (c) Yao, C.-H.; Yang, C.-M.; Chao, H.-H.; Lee, G.-R. Method for Preparing Prostaglandin F Analogue. US2009/0259066A1, Oct. 15, 2009. (d) Resul, B.; Stjernschantz, J.; No, K.; Liljebris, C.; Selen, G.; Astin, M.; Karlsson, M.; Bito, L. Z. Phenyl-Substituted Prostaglandins: Potent and Selective Antiglaucoma Agents. J. Med. Chem. 1993, 36, 243–248. doi: 10.1021/jm00054a008.
  • Martynow, J. G.; Jóźwik, J.; Szelejewski, W.; Achmatowicz, O.; Kutner, A.; Wiśniewski, K.; Winiarski, J.; Zegrocka-Stendel, O.; Gołębiewski, P. A New Synthetic Approach to High-Purity (15R)-Latanoprost. Eur. J. Org. Chem. 2007, 2007, 689–703. doi: 10.1002/ejoc.200600749.
  • Rao, D. V. L. N.; Kommana, P.; Narayana, C. L.; Srinivasu, G. Preparation of Prostaglandin Derivatives. WO2012/11128A1, Jan. 26, 2012.
  • (a) Dams, I.; Andrzej, K.; Michal, C. Process for Preparation of Prostaglandin F2 Alpha Analogues. US2015/0031898, Jan. 29, 2015. (b) Zhijun, T.; Bingming, H.; Lin, L.; Shunzhou, S.; Zhonghao, Z.; Yunman, Z.; Weiliang, G.; Xiaoming, J. Preparation Method for Prostaglandin Intermediate, CN102050808B. Mar. 12, 2014.
  • (a) Gutman, A.; Rukhman, I.; Tishin, B.; Yudovich, L.; Vilensky, A.; Pertsikov, B.; Nisnevich, G. Bimatoprost Crystalline Form I. US2009/163596, 2009. (b) Albert, M.; Berger, A.; Dominic De, S.; Knepper, K.; Sturm, H. Improved Process for the Production of Prostaglandins and Prostaglandin Analogs. EP2143712A1. Jan. 13, 2010. (c) Rao, K. N.; Bhausaheb, C.; Krishna, P. M. Improved Process for Prostaglandind and Analogues Thereof. WO2010109476A2, Sep. 30, 2010.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.