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Methylnaltrexone bromide

CAT#: H318250

CAS#: 73232-52-7

Description: Methylnaltrexone, used in form of methylnaltrexone bromide (INN, USAN, BAN), is one of the newer agents of peripherally-acting μ-opioid antagonists that act to reverse some of the side effects of opioid drugs such as constipation without affecting analgesia or precipitating withdrawals. Because Methylnaltrexone is a quaternary ammonium cation, it cannot cross the blood–brain barrier, and so has antagonist effects throughout the body, counteracting effects such as itching and constipation, but without affecting opioid effects in the brain such as analgesia.

Synthetic Routes

Methylnaltrexone bromide - Synthetic Route 1

Synthetic reference

Meng, Wenxue; Long, Daobing; Xiong, Dewang. Preparation method of methylnaltrexone bromide and intermediate thereof. Assignee Chongqing Landtower Pharmaceutical Co., Ltd., Peop. Rep. China. CN 107021978. (2017).

Methylnaltrexone bromide - Synthetic Route 2

Synthetic reference

Dlubala, Alain. Process for preparing N-alkylnaltrexone halides. Assignee Sanofi-Aventis, Fr. WO 2008034973. (2009).

Methylnaltrexone bromide - Synthetic Route 3

Synthetic reference

Weigl, Ulrich; Schaer, Pascal; Stutz, Alfred. Method for producing N-methylnaltrexone bromide. Assignee Cilag A.-G., Switz. WO 2008138605. (2008).

Methylnaltrexone bromide - Synthetic Route 4

Synthetic reference

Wang, Jianping; Jia, Jianbo; Zhang, Yixin; Dou, Guohua; Lu, Weigang. Method for preparation of methylnaltrexone bromide with Naltrexone hydrochloride. Assignee Shandong Xinhua Pharmaceutical Co., Ltd., Peop. Rep. China. CN 103626782. (2014).

Methylnaltrexone bromide - Synthetic Route 5

Synthetic reference

Guo, Zhao. Method for preparation of methylnaltrexone bromide. Assignee Nanjing Cuccess Pharmaceutical Co., Ltd., Peop. Rep. China. CN 101845047. (2010).

Methylnaltrexone bromide - Synthetic Route 6

Synthetic reference

Wang, Peter X.; Halvachs, Robert E.; Roesch, Kevin R.; Buehler, Henry J.; Haar, Joseph P. Process for the preparation of quaternary N-alkyl morphinan alkaloid salts. Assignee Mallinckrodt Inc., USA; Cantrell, Gary, L. WO 2008109156. (2008).

Methylnaltrexone bromide - Synthetic Route 7

Synthetic reference

Sun, Huafu; Dan, Chunyan; Luo, Jie; Ye, Wenrun; Lin, Bo; Zhang, Daolin; Liao, Wei. Method for preparation of morphinan bromide quaternary ammonium salt. Assignee Chongqing Pharmaceutical Research Institute Co., Ltd., Peop. Rep. China. WO 2012010106. (2012).

Methylnaltrexone bromide - Synthetic Route 8

Synthetic reference

Cantrell, Gary L.; Halvachs, Robert E. Preparation of quaternary salts of morphinan alkaloids. Assignee Mallinckrodt Inc., USA. WO 2004043964. (2004).

Methylnaltrexone bromide - Synthetic Route 9

Synthetic reference

Eipert, Martin; Lauterbach, Erik, Heinz; Heller, Sabrina; Dinkel, Thomas; Hake, Stephanie. Process for the preparation of quaternary N-alkyl morphine or morphinan alkaloid derivatives. Assignee Siegfried Ltd., Switz. EP 2019105. (2009).

Methylnaltrexone bromide - Synthetic Route 10

Synthetic reference

Yi, Chongqin; Tan, Zulei; Yang, Yang; Ji, Lei; Huang, Qi. Method for preparing methylnaltrexone bromide. Assignee Peking University Founder Group Co., Ltd., Peop. Rep. China; PKU Care Pharmaceutical R&D Center; PKU HealthCare Industry Group Co., Ltd. CN 106317064. (2017).