Suproclone
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| ECHA InfoCard | 100.071.330 |
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| Formula | C22H22ClN5O4S2 |
| Molar mass | 520.02 g·mol−1 |
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Suproclone is a sedative and anxiolytic drug in the cyclopyrrolone family of drugs, developed by the French pharmaceutical company Rhône-Poulenc.[1] Other cyclopyrrolone drugs include zopiclone, pagoclone and suriclone.
Suproclone is very similar in structure to the related drug suriclone, but little information has been published about it specifically. However it can be expected that the mechanism of action by which suproclone produces its sedative and anxiolytic effects is by modulating benzodiazepine receptors (resulting in an increased response to endogenous GABA), in a similar manner to other drugs of this class.[2][3]
Synthesis
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The condensation between 2,3-Dihydro-1,4-dithiino[2,3-c]furan-5,7-dione [10489-75-5] (1) and 7-Chloro-1,8-naphthyridin-2-amine [15944-33-9] (2) gives PC23343647 (3). Halogenation with phosphoryl chloride leads to PC23343652 (4). Reductino with potassium borohydride afforded [53788-25-3] (5). Treatment with phenyl chloroformate [1885-14-9] (6) resulted in 2-(7-chloro-1,8-naphthyridin-2-yl)-3-phenoxycarbonyloxy-isoindolin-1-one, PC23343637 (7). Reaction with piperazine [110-85-0] (8) afforded (9). Acylation with propionyl chloride completed the synthesis of Suproclone (10).
References
[edit]- ^ Psychotropics.dk. "suproclone". Retrieved 24 August 2009.
- ^ Gardner CR (1988). "Pharmacological profiles in vivo of benzodiazepine receptor ligands". Drug Development Research. 12 (1): 1–28. doi:10.1002/ddr.430120102. S2CID 85573551.
- ^ Doble A, Martin I, Nutt D (23 October 2003). Calming the brain: benzodiazepines and related drugs from laboratory to clinic. Informa Healthcare. ISBN 1-84184-052-1.
- ^ Serradell, MN; Castaer, J.; Suproclone. Drugs Fut 1985, 10, 1, 45.
- ^ Claude Cotrel, Claude Jeanmart, Mayer N. Messer, Cornel Crisan, U.S. patent 4,220,646 (1980 to Rhone-Poulenc Industries).
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