Darunavir

CAT#: H315293

CAS#: 206361-99-1

Description: Darunavir is a drug used to treat HIV infection. It is in the protease inhibitor class. Prezista is an OARAC recommended treatment option for treatment-naïve and treatment-experienced adults and adolescents. Developed by pharmaceutical company Tibotec, darunavir is named after Arun K. Ghosh, the chemist who discovered the molecule at the University of Illinois at Chicago. It was approved by the Food and Drug Administration (FDA) on June 23, 2006. .

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Synthetic Routes

Darunavir - Synthetic Route 1

Darunavir route01

Synthetic reference

Ghosh, Arun K.; Leshchenko, Sofiya; Noetzel, Marcus. Stereoselective Photochemical 1,3-Dioxolane Addition to 5-Alkoxymethyl-2(5H)-furanone: Synthesis of Bis-tetrahydrofuranyl Ligand for HIV Protease Inhibitor UIC-94017 (TMC-114). Journal of Organic Chemistry. Department of Chemistry. University of Illinois at Chicago. Chicago, USA 60607. Volume 69. Issue 23. Pages 7822-7829. 2004

Darunavir - Synthetic Route 2

Darunavir route02

Synthetic reference

Moore, Gary L.; Stringham, Rodger W.; Teager, David S.; Yue, Tai-Yuen. Practical Synthesis of the Bicyclic Darunavir Side Chain: (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol from Monopotassium Isocitrate. Organic Process Research & Development. Clinton Health Access Initiative. West Chester, USA 19380. Volume 21. Issue 1. Pages 98-106. 2017

Darunavir - Synthetic Route 3

Darunavir route03

Synthetic reference

Surleraux, Dominique L. N. G.; Tahri, Abdellah; Verschueren, Wim G.; Pille, Geert M. E.; de Kock, Herman A.; Jonckers, Tim H. M.; Peeters, Anik; De Meyer, Sandra; Azijn, Hilde; Pauwels, Rudi; de Bethune, Marie-Pierre; King, Nancy M.; Prabu-Jeyabalan, Moses; Schiffer, Celia A.; Wigerinck, Piet B. T. P. Discovery and Selection of TMC114, a Next Generation HIV-1 Protease Inhibitor. Journal of Medicinal Chemistry. Tibotec BVBA. Mechelen, Belg. B-2800. Volume 48. Issue 6. Pages 1813-1822. 2005

Darunavir - Synthetic Route 4

Darunavir route04

Synthetic reference

Kanemitsu, Takuya; Inoue, Mizuho; Yoshimura, Nono; Yoneyama, Kazutoshi; Watarai, Rie; Miyazaki, Michiko; Odanaka, Yuki; Nagata, Kazuhiro; Itoh, Takashi. A Concise One-Pot Organo- and Biocatalyzed Preparation of Enantiopure Hexahydrofuro[2,3-b]furan-3-ol: An Approach to the Synthesis of HIV Protease Inhibitors. European Journal of Organic Chemistry. School of Pharmacy. Showa University. 1-5-8 Hatanodai, Shinagawa-ku, Tokyo, Japan 142-8555. Volume 2016. Issue 10. Pages 1874-1880. 2016

Darunavir - Synthetic Route 5

Darunavir route05

Synthetic reference

Rapolu, Rajesh Kumar; Areveli, Srinivas; Raju, V. V. N. K. V. Prasada; Navuluri, Srinivasu; Chavali, Murthy; Mulakayala, Naveen. An Efficient Synthesis of Darunavir Substantially Free from Impurities: Synthesis and Characterization of Novel Impurities. ChemistrySelect. R&D Center.Granules India Limited. Hyderabad, India 5000072. Volume 4. Issue 14. Pages 4422-4427. 2019

Darunavir - Synthetic Route 6

Darunavir route06

Synthetic reference

Gadakh, Sunita Khanderao; Rekula, Reddy Santhosh; Sudalai, Arumugam. Process for the preparation of syn azido epoxides as useful intermediates for the synthesis of amprenavir and saquinavir. Assignee Council of Scientific & Industrial Research, India. WO 2013105118. 2013

Darunavir - Synthetic Route 7

Darunavir route07

Synthetic reference

Thirumalai Rajan, Srinivasan; Eswaraiah, Sajja; Satyanarayana, Revu. Process for preparation of [(1S,2R)-3-[[(4-aminophenyl)sulfonyl] (2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl ester (darunavir) and its amorphous form. Assignee MSN Laboratories Private Limited, India. WO 2016207907. 2016

Darunavir - Synthetic Route 8

Darunavir route08

Synthetic reference

Moro, Ravi Vitthal; Herlekar, Pravin Shivdas. An improved process for the preparation of darunavir. IN 2015MU00282. 2016

Darunavir - Synthetic Route 9

Darunavir route09

Synthetic reference

Wigerinck, Piet Tom Bert Paul; Surleraux, Dominique Louis Nestor Ghislain; Verschueren, Wim Gaston; De Kock, Herman Augustinus; Aelterman, Wim Albert Alex. Process for the preparation of darunavir from N-benzylisobutylamine, a protected aminophenylethyloxirane, a hexahydrofurofuran derivative, and a nitrophenylsulfonyl compound. Assignee Tibotec Pharmaceuticals, Ire. WO 2010023322. 2010

Darunavir - Synthetic Route 10

Darunavir route010

Synthetic reference

Mizhiritskii, Michael; Marom, Ehud. Process for the preparation of darunavir and darunavir intermediates. Assignee MAPI Pharma HK Limited, Peop. Rep. China. WO 2011092687. 2011