17977-76-3Relevant academic research and scientific papers
Synthesis of substituted 3-anilino-5-phenyl-1,3-dihydro-2H-1,4- benzodiazepine-2-ones and their evaluation as cholecystokinin-ligands
Offel, Michael,Lattmann, Pornthip,Singh, Harjit,Billington,Bunprakob, Yodchai,Sattayasai, Jintana,Lattmann, Eric
, p. 163 - 173 (2007/10/03)
3-Amino-1,4-benzodiazepines as well as chemically related diverse amines were prepared from oxazepam and subsequently screened on the cholecystokinin receptor in a radiolabel binding assay. Oxazepam 2 was activated via its 3-chloro-1,4-benzodiazepine intermediate 3 and was reacted with a large series of aliphatic and aromatic amines. The substituted 3-anilino-1,4-benzodiazepine structure was identified as lead structure in a diverse series of 3-amino-1,4-benzodiazepines 4-38 and the full SAR (structure-activity relationship) optimisation provided 3-anilinobenzodiazepines 16-38 with CCK 1 receptor selectivity to CCK2. The compounds 18, 24, 28 and 33 have shown affinities at the CCK1 receptor of 11, 10, 11 and 9 nM, respectively. These equipotent CCK1 ligands were fully evaluated in behaviour pharmacological essays. An antidepressant effect was identified in the tail suspension- and the Porsolt swimming-test. The ED50 values for 24 and 28 were determined in these assays as 0.46 and 0.49 mg/kg. The mixed antagonist 37 showed in addition to the antidepressant effects anxiolytic properties.
NOVEL 3-SUBSTITUTED-1,4-BENZODIAZEPINES
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Page 27, (2010/02/09)
The present invention relates to compounds of formula (I). The invention also relates to methods for preparing the compounds and their uses as CCK receptor ligands and CCK antagonists.
