Rotigotine

CAT#: H471031

CAS#: 99755-59-6

Description: Rotigotine is a non-selective dopamine receptor agonist with preference for D3 receptors over D2 and D1. As such, it is an effective anti-Parkinsonian agent. Racemic rotigotine is about 50 times as potent as quinpirole, the gold standard D2 agonist.

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Synthetic Routes

Rotigotine - Synthetic Route 1

Rotigotine route01

Synthetic reference

Webster, Robert; Boyer, Alistair; Fleming, Matthew J.; Lautens, Mark. Practical Asymmetric Synthesis of Bioactive Aminotetralins from a Racemic Precursor Using a Regiodivergent Resolution. Organic Letters. Volume 12. Issue 23. Pages 5418-5421. 2010.

Rotigotine - Synthetic Route 2

Rotigotine route02

Synthetic reference

Khunt, Mayur Devjibhai; Varma, Shrikant; Patil, Nilesh Sudhir; Pagire, Haushabhau Shivaji; Pradhan, Nitin Sharadchandra. Process for preparation of highly pure rotigotine and pharmaceutically acceptable salts thereof. Assignee Actavis Group PTC Ehf, Iceland. WO 2010073124. (2010).

Rotigotine - Synthetic Route 3

Rotigotine route03

Synthetic reference

Lu, Jun; Zhang, Yanfei; Yang, Jin; Mao, Dongyan; Shen, Zongxuan. A preparation method of rotigotine and its derivatives. Assignee Suzhou Chireach Biomedical Technology Co., Ltd., Peop. Rep. China. CN 101717392. (2010).

Rotigotine - Synthetic Route 4

Rotigotine route04

Synthetic reference

Park, Do Young; Kim, Kyung-Hee; Cheon, Cheol-Hong. Enantioselective Synthesis of β-Aminotetralins via Chiral Phosphoric Acid-catalyzed Reductive Amination of β-Tetralones. Advanced Synthesis & Catalysis. Volume 360. Issue 3. Pages 462-467. 2018.

Rotigotine - Synthetic Route 5

Rotigotine route05

Synthetic reference

Cobley, Christopher J.; Evans, George; Fanjul, Tamara; Simmonds, Shaun; Woods, Amy. New catalytic route for the synthesis of an optically active tetralone-derived amine for rotigotine. Tetrahedron Letters. Volume 57. Issue 9. Pages 986-989. 2016.

Rotigotine - Synthetic Route 6

Rotigotine route06

Synthetic reference

He, Xungui; Guo, Jianping; Wang, Yanling; Tang, Wensheng; Zhang, Xingzhong; Wang, Xuezhang; Wang, Yuan. A process for preparing rotigotine and its pharmaceutically acceptable salts. Assignee 2Y-Chem, Ltd., Peop. Rep. China. WO 2011026318. (2011).

Rotigotine - Synthetic Route 7

Rotigotine route07

Synthetic reference

Pomares, Marta; Marquillas, Francisco. Process for the preparation of (6S)-(-)-5,6,7,8-tetrahydro-6-[propyl-(2-thienyl)ethyl]amino-1-naphthol (rotigotine) using improved alkylation and hydrolysis steps. Assignee Interquim, S.A., Spain. WO 2010066755. (2010).

Rotigotine - Synthetic Route 8

Rotigotine route08

Synthetic reference

Kandula, Mahesh. Compositions and methods for treatment of neurologic diseases. WO 2013168033. (2013).

Rotigotine - Synthetic Route 9

Rotigotine route09

Synthetic reference

Wang, Keliu; Wang, Meihai. Process for preparation of rotigotine. Assignee Shandong Lubei Pharmaceutical Limited, Peop. Rep. China. CN 103058985. (2013).

Rotigotine - Synthetic Route 10

Rotigotine route010

Synthetic reference

Irudayaraj, Victor Paul Raj; Subramani, Senthilkumar; Govindaraj, Vedhachalam; Jayavelu, Jeyakanthan; Jayaraman, Boopathy; Ray, Uttam Kumar; Vittal, Tangirala. Novel process for preparation of rotigotine and intermediates thereof from ( S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-naphthalenamine hydrochloride and 2-thiopheneacetyl chloride via demethylation of (2S)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-propyl-2-(thien-2-yl)ethanamide with aluminum chloride. Assignee Solara Active Pharma Sciences Limited, India. US 20190248758. (2019).