312625-23-3

Usage

Chemical compound

4-[2-[(3S,4S)-4-benzyl-3-methyl-1-piperidyl]ethylsulfonyl]phenol

Function

Potent and selective inhibitor of Toll-like receptor 4 (TLR4)

Role in innate immune system

Blocks TLR4-mediated signaling and inhibits production of pro-inflammatory cytokines

Potential therapeutic agent for

Treatment of inflammatory and immune-related diseases

Additional effects

Demonstrated neuroprotective effects in pre-clinical studies

Potential in treating

Neurological disorders

Need for further research

To fully understand therapeutic potential.

Upstream product

• 312625-48-2 4-((2-chloroethyl)sulfonyl)phenol 
• 1378692-26-2 (3SR,4SR)-4-benzyl-piperidine-3-ol 
• 637-89-8 4-sulfanylphenol 
• 30519-04-1 4-(2-hydroxyethylsulfanyl) phenol 
• 101637-76-7 4-(2-chloro-ethylsulfanyl)-phenol 
• 312625-46-0 (SR)-1,4-dibenzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester 
• 52763-21-0 ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride 
• 63876-32-4 4-[benzyl(ethoxycarbonylmethyl)amino]butyric acid ethyl ester 
• 220426-78-8 [but-3-enyl-((1R)-phenyl-ethyl)-amino]-acetic acid ethyl ester 
• 857858-99-2 (2R,3S)-3-Benzyl-1-((R)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid ethyl ester 
• 857859-00-8 [(2R,3S)-3-Benzyl-1-((R)-1-phenyl-ethyl)-pyrrolidin-2-yl]-methanol 
• 312625-28-8 (3S,4S)-4-benzylpiperidin-3-ol 
• 857859-01-9 (3S,4S)-4-Benzyl-1-((R)-1-phenyl-ethyl)-piperidin-3-ol 

Relevant academic research and scientific papers

Efficient enantioselective formal synthesis of Ro 67-8867, a NMDA 2B receptor antagonist

An efficient enantioselective formal synthesis of Ro 67-8867 has been achieved in 7 steps using an amino-zinc-ene-enolate cyclization and an enantioselective ring enlargement of a substituted prolinol as the key steps.

Efficient enantioselective synthesis of the NMDA 2B receptor antagonist Ro 67-8867

An efficient, enantioselective, and scalable eight-step synthesis for the NMDA 2B receptor antagonist Ro 67-8867 (S,S)-1 selected for the treatment of acute ischemie stroke is described based on the coupling reaction of the amino alcohol (S,S)-6 with the sulfone building block 7. The synthesis of the amino alcohol (S,S)-6 was achieved by the highly selective asymmetric hydrogenation of the piperidinone 4*HCl proceeding with concomitant dynamic kinetic resolution to (S,S)-5. Subsequent debenzylation afforded the enantiomerically pure amino alcohol (S,S)-6 after ee-enhancement by simple crystallization in good yield. The hydrogenation substrate 4*HCl was prepared as a stable hydrochloride in two steps from ethyl N-benzyl-3-oxo-4-piperidinecarboxylate hydrochloride (2) for which a new, short, efficient, and cheap synthesis was developed. To bypass a mutagenic intermediate, a revised safe protocol for the sulfone building block 7 was established. The new synthesis allows the access to Ro 67-8867 (S,S)-1 in an overall yield of 53% compared to 3.5% of the Discovery Chemistry approach.

Ethanesulfonyl-piperidine derivatives

The invention relates to compounds of the general formula STR1whereinR 1 signifies hydrogen or hydroxy; R 2 signifies hydrogen or methyl; and X signifies --O-- or --CH 2 -- and their pharmaceutically acceptable acid addition salts.It has been shown that these compounds have a good affitity to the NMDA receptor and they are therefore useful in the treatment of diseases, wherein the therapeutic indications include acute forms of neurodegeneration caused, e.g., by stroke or brain trauma; chronic forms of neurodegeneration such as Alzheimer''s disease, Parkinson''s disease, Huntington''s disease or ALS (amyotrophic lateral sclerosis); neurodegeneration associated with bacterial or viral infections, and, diseases such as schizophrenia, anxiety, depression and chronic/acute pain.

Process for the preparation of ethanesul fonyl-piperidine derivatives

The present invention relates to a new process for the preparation of compounds of the formulae and their pharmaceutically acceptable acid addition salts, which are NMDA (N-methyl-D-aspartate)-receptor-subtype selective blockers.