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Synthesis of enantiopure angiotensin II type 2 receptor [AT(2)R] antagonist EMA401
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. Uppsala University, Science for Life Laboratory, SciLifeLab.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry. Uppsala University, Science for Life Laboratory, SciLifeLab.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preclinical PET Platform. Uppsala University, Science for Life Laboratory, SciLifeLab.
2015 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 71, no 38, 6881-6887 p.Article in journal (Refereed) Published
Abstract [en]

We report a facile synthesis of the angiotensin II type 2 receptor antagonist EMA401, which recently passed phase II clinical trials, in high overall yield. The synthesis of the key phenylalanine intermediate involved the formation of an a-nitro cinnamic ester and its reduction followed by a Pictet-Spengler cyclization, which furnished the tetrahydroisoquinoline core structure. Next, EMA401 was separated from its enantiomer EMA402 by four recrystalizations of a diastereomeric salt in 98% ee. All steps were performed on gram scale with emphasis on avoiding column purification and using readily available low cost starting materials and reagents.

Place, publisher, year, edition, pages
2015. Vol. 71, no 38, 6881-6887 p.
Keyword [en]
EMA401, Angiotensin II type 2 receptor, Synthesis, Enantiopure
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-262404DOI: 10.1016/j.tet.2015.07.018ISI: 000359874300032OAI: oai:DiVA.org:uu-262404DiVA: diva2:855439
Available from: 2015-09-21 Created: 2015-09-15 Last updated: 2017-12-04Bibliographically approved

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Wannberg, JohanLarhed, Mats

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Organic Pharmaceutical ChemistryDepartment of Medicinal ChemistryScience for Life Laboratory, SciLifeLabPreclinical PET Platform
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