64306-76-9Relevant academic research and scientific papers
Synthesis, pharmacological activity and structure affinity relationships of spirocyclic σ1 receptor ligands with a (2-fluoroethyl) residue in 3-position
Maestrup, Eva Gro?e,Wiese, Christian,Schepmann, Dirk,Brust, Peter,Wünsch, Bernhard
experimental part, p. 393 - 405 (2011/02/27)
In order to develop a fluorinated radiotracer for imaging of σ1 receptors in the central nervous system a series of (2-fluoroethyl) substituted spirocyclic piperidines 3 has been prepared. In the key step of the synthesis 2-bromocinnamaldehyde
Thiophene bioisosteres of spirocyclic σ receptor ligands. 1. N-substituted spiro[piperidine-4,4′-thieno[3,2-c]pyrans]
Oberdorf, Christoph,Schepmann, Dirk,Vela, Jose Miguel,Diaz, Jose Luis,Holenz, J?rg,Wünsch, Bernhard
supporting information; experimental part, p. 6531 - 6537 (2009/10/17)
Herein, the synthesis and pharmacological evaluation of thiophene bioisosteres of the highly potent spirocyclic benzopyran 1 are detailed. The synthesis of 1-benzyl-6′-methoxy-6′,7′- dihydrospiro[piperidine-4,4′-thieno[3.2-c]pyran] (2a) was performed starting with 3-bromothiophene (3). After introduction of the acetaldehyde substructure (7), halogen metal exchange, addition of 1-benzylpiperidin-4-one, and cyclization led to the spirocyclic thienopyran 2a. The removal of the benzyl group afforded the secondary amine 2f, which was substituted with various residues. With respect to σ1 affinity the N-benzyl derivative 2a, the N-cyclohexylmethyl derivative 2d, and the N-p-fluorobenzyl derivative 2i represent the most potent compounds of this series binding with Ki values of 0.32, 0.29, and 0.62 nM, respectively. Electronic properties of the substituents have only little impact on σ1 affinity. The most potent σ1 ligands display high selectivity against σ2, 5-HT1A, 5-HT6, 5-HT7, α1A, α2, and NMDA receptors. The activity of 2a in the mouse capsaicin assay seems to indicate σ1 antagonistic activity.
SPIRO [PIPERIDINE-4, 4' -THIENO [3, 2-C] PYRAN] DERIVATIVES AND RELATED COMPOUNDS AS INHIBITORS OF THE SIGMA RECEPTOR FOR THE TREATMENT OF PSYCHOSIS
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Page/Page column 73-74, (2009/01/23)
The present invention relates to compounds having pharmacological activity towards the sigma (s) receptor, and more particularly to some thieno-pyrano-pyrazole derivatives, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use in therapy and prophylaxis, in particular for the treatment of psychosis or pain.
PESTICIDAL SUBSTITUTED PIPERIDINES
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Page/Page column 51; 79, (2008/06/13)
The invention relates to the use of piperidine derivatives encompassed from the general formula (I) for the control of pests, including arthropods and helminths, and a method for the control of pests.
