Chemistry:SKF-89976A

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SKF-89976A is an anticonvulsant, acting as a GABA reuptake inhibitor via blockade of GAT-1.[1]

Synthesis

Synthesis:[2][3] Patent:[4][5]

Ex 1: Finkelstein Sn2 alkylation between 1,1-Diphenyl-4-bromobutene [6078-95-1] (1) & Ethyl nipecotate [5006-62-2] (2) gives [89203-62-3] (3). Optional saponification of the ester group gives the title amino-acid compound (4).

NNC-47-0011:[6] Patent:[7]

References

  1. ↑ Moldavan, Michael; Cravetchi, Olga; Allen, Charles N. (2017-12-01). "GABA transporters regulate tonic and synaptic GABAA receptor-mediated currents in the suprachiasmatic nucleus neurons". Journal of Neurophysiology 118 (6): 3092–3106. doi:10.1152/jn.00194.2017. ISSN 1522-1598. PMID 28855287. 
  2. ↑ Lscher, W.; SK&F-89976-A. Drugs Fut 1986, 11, 1, 36.
  3. ↑ Ali, Fadia E.; Bondinell, William E.; Dandridge, Penelope A.; Frazee, James S.; Garvey, Eleanor; Girard, Gerald R.; Kaiser, Carl; Ku, Thomas W.; Lafferty, John J.; Moonsammy, George I.; Oh, Hye-Ja; Rush, Julia A.; Setler, Paulette E.; Stringer, Orum D.; Venslavsky, Joseph W.; Volpe, Beth W.; Yunger, Libby M.; Zirkle, Charles L. (1985). "Orally Active and Potent Inhibitors of γ-Aminobutyric Acid Uptake". Journal of Medicinal Chemistry. 28 (5): 653–660. doi:10.1021/jm50001a020.
  4. ↑ William E. Bondinell, John J. Lafferty, & Charles L. Zirkle, U.S. Patent 4,383,999 (1983 to SmithKline Beecham Corp).
  5. ↑ William E. Bondinell, et al. EP0066456 (1985 to SmithKline Beecham Corp).
  6. ↑ Cao, R., Cao, Y., Dissing, S., Hansen, A. J., Kristjansen, P. E. G., Olsen, U. B. (September 2003). "579 Significant tumor growth inhibition of glioblastoma xenografts by NNC 47-0011 — a low molecular weight tricyclic tyrosine kinase modulator with anti-angiogenic activity". European Journal of Cancer Supplements. 1 (5): S175. doi:10.1016/S1359-6349(03)90611-2.
  7. ↑ Knud Erik Andersen, et al. WO1995018793 (to Novo Nordisk AS).
  • Borden, L. A.; Murali Dhar, T. G.; Smith, K. E.; Weinshank, R. L.; Branchek, T. A.; Gluchowski, C. (1994). "Tiagabine, SK&F 89976-A, CI-966, and NNC-711 are selective for the cloned GABA transporter GAT-1". European Journal of Pharmacology 269 (2): 219–224. doi:10.1016/0922-4106(94)90089-2. PMID 7851497. 




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