1253197-75-9

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 13398-94-2 2-(3-hydroxyphenyl)ethanol 
• 100-39-0 benzyl bromide 
• 511286-68-3 methyl (R)-2-(p-tosylamino)propionate 
• 1253197-74-8 methyl (R)-l-2-{N-[2-(3-benzyloxyphenyl)ethyl]-N-(4-tosyl)amino}propionate 
• 177259-98-2 2-[(3-(benzyloxy)phenyl)]ethan-1-ol 

Downstream Products

• 1253197-77-1 (R)-9-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-3-benzazepine-1-one 
• 1253197-76-0 (R)-7-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-3-benzazepine-1-one 
• 1253197-79-3 (1R,2R)-7-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-1-ol 
• 1253197-78-2 (1S,2R)-7-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-1-ol 

Relevant academic research and scientific papers

NR2B SELECTIVE NMDA-RECEPTOR ANTAGONISTS FOR TREATMENT OF IMMUNE-MEDIATED INFLAMMATORY DISEASES

The present invention provides novel means and methods for treatment auf immunemediated inflammatory diseases.

Enantiomerically Pure 2-Methyltetrahydro-3-benzazepin-1-ols Selectively Blocking GluN2B Subunit Containing N-Methyl-d-aspartate Receptors

A chiral pool synthesis was developed to obtain all four stereoisomeric 2-methyl-3-(4-phenylbutyl)tetrahydro-3-benzazepin-1-ols 21, 31, and 32 in a seven- to eight-step sequence. The phenols 32 reveal slightly higher GluN2B affinity than the methyl ethers 21. The GluN2B affinity increases in the order (1R,2S) (1S,2S) (1S,2R) (1R,2R). The stereoisomeric phenols (R,R)-32 and (S,R)-32 show the highest GluN2B affinity and the highest cytoprotective activity. Both compounds represent GluN2B selective allosteric NMDA receptor antagonists. Docking of the 3-benzazepin-1-ols into the ifenprodil binding site of the crystallized GluN1b/GluN2B N-terminal domains led to free binding energies, which correlate nicely with the experimentally determined GluN2B affinities. The similar GluN2B affinity of the stereoisomeric phenols (S,S)-32, (R,R)-32, and (S,R)-32 is explained by different binding modes of the 3-benzazepine scaffold. The benzyl ethers 31 reveal unexpectedly high GluN2B affinity but do not show cytoprotective effects. The additional benzyl moiety of 31 binds into a previously unrecognized lipophilic subpocket.

NR2B-SELECTIVE NMDA-RECEPTOR ANTAGONISTS

The present invention relates to compounds according to general formula (I) and pharmaceutical compositions comprising compounds according to general formula (I).