SKF-89976A

Last updated
SKF-89976A
SKF-89976A.svg
Names
Other names
N-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C22H25NO2/c24-22(25)20-13-7-15-23(17-20)16-8-14-21(18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-6,9-12,14,20H,7-8,13,15-17H2,(H,24,25)
    Key: TXQKSMSLZVKQBI-UHFFFAOYSA-N
  • C1CC(CN(C1)CCC=C(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)O
Properties
C22H25NO2
Molar mass 335.447 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Contents

Synthesis

Synthesis: Patent: SKF-89976A synthesis.svg
Synthesis: Patent:

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).

See also

NNC-47-0011: Patent: NNC-47-0011.svg
NNC-47-0011: Patent:

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. PMC   5814714 . 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).