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A novel scalable synthesis of pramipexoleŽivec, Matej, 1979- ; Anžič, Borut ; Gobec, Stanislav, 1970-Pramipexole is a dopamine D2 subfamily receptor agonist that is used for the treatment of Parkinson's disease. We report here on the successful application of the Fukuyama alkylation protocol to the ... development of a novel and scalable process for synthesis of pramipexole and its pharmaceutically acceptable salts. The synthesis consists of converting the crucial intermediate (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole to (6S)-N-(2-amino-4,5,6,7-tetrahydrobenzothiazole- 6-yl)-2-nitrobenzenesulfonamide, which is in turn monoalkylated to (6S)-N-(2-amino-4,5,6,7-tetrahydrobenzothiazole- 6-yl)-2-nitro-N-propylbenzenesulfonamide. Deprotection of the latter yields pramipexole base, which is finally converted to a crude pramipexole dihydrochloride monohydrate with a yield of over 50% over four steps. The process allows for the telescoping of the final three steps, has high conversion rates of intermediates, offers ease of purification, and preserves high optical purity throughout all of the stages.Source: Organic process research & development. - ISSN 1083-6160 (vol. 14, iss. 5, 2010, str. 1125-1129)Type of material - article, component partPublish date - 2010Language - englishCOBISS.SI-ID - 2858353
Author
Živec, Matej, 1979- |
Anžič, Borut |
Gobec, Stanislav, 1970-
Topics
pramipeksol |
Parkinsonova bolezen |
sinteza
source: Organic process research & development. - ISSN 1083-6160 (vol. 14, iss. 5, 2010, str. 1125-1129)
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Database name | Field | Year |
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Links to authors' personal bibliographies | Links to information on researchers in the SICRIS system |
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Živec, Matej, 1979- | 26493 |
Anžič, Borut | 12810 |
Gobec, Stanislav, 1970- | 15284 |
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