209257-75-0

Upstream product

• 128726-47-6 (+)-(S)-6-hydroxymethyl-2-piperidinone 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 187851-95-2 (4-methoxyphenyl)methyl hex-5-enoate 
• 187851-96-3 (4-methoxyphenyl)methyl (R)-5,6-dihydroxyhexanoate 
• 187851-97-4 (4-methoxyphenyl)methyl (R)-6-[(tert-butyldiphenylsilyl)oxy]-5-hydroxyhexanoate 
• 1118-90-7 L-homoglutamic acid 
• 34622-39-4 (2S)-6-oxopipecolic acid 
• 158414-69-8 (-)-(S)-6-oxo-2-piperidinecarboxylic acid methyl ester 
• 213533-00-7 (R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methanesulfonyloxy-hexanoic acid 4-methoxy-benzyl ester 
• 213533-01-8 (S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-hexanoic acid 4-methoxy-benzyl ester 

Downstream Products

• 197142-43-1 2-(tert-butyl-diphenylsilanyloxymethyl)-6-oxo-piperidine-1-carboxylic acid tert-butyl ester 
• 128726-47-6 (+)-(S)-6-hydroxymethyl-2-piperidinone 
• 209257-77-2 (S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-piperidine-2-thione 
• 442202-20-2 methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate 
• 197142-46-4 3-(tert-butyl-diphenylsilanyloxymethyl)-2-aza-bicyclo[4.1.0]heptane-2-carboxylic acid tert-butyl ester 
• 209257-79-4 2-[(S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-piperidin-2-ylidene]-malonic acid diethyl ester 
• 442202-05-3 dimethyl (S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5,6-dihydro-4H-pyridine-1,2-dicarboxylate 
• 619267-04-8 methyl (2R,3R,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-2-hydroxymethyl-3-methylpiperidine-1-carboxylate 
• 619266-91-0 dimethyl (2R,3R,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-methylpiperidine-1,2-dicarboxylate 
• 619266-92-1 (5S,8R,9R)-(-)-5-(tert-butyldiphenylsilyloxymethyl)-8-methylhexahydrooxazolo[3,4-a]pyridin-3-one 
• 619267-06-0 methyl (8R,9R)-(-)-8-methyl-3-oxo-5-phenylsulfanylhexahydrooxazolo[3,4-a]pyridine-5-carboxylate 
• 442202-21-3 methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylate 
• 442202-22-4 dimethyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-vinyl-piperidine-1,2-dicarboxylate 
• 442202-06-4 methyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-2-hydroxymethyl-3-vinylpiperidine-1-carboxylate 

Relevant academic research and scientific papers

Discovery and Development of 3-(6-Chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]hexane Hydrochloride (SUVN-911): A Novel, Potent, Selective, and Orally Active Neuronal Nicotinic Acetylcholine α4β2 Receptor Antagonist for the Treatment of Depression

A series of chemical optimizations guided by in vitro affinity at the α4β2 receptor in combination with selectivity against the α3β4 receptor, pharmacokinetic evaluation, and in vivo efficacy in a forced swim test resulted in identification of 3-(6-chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]hexane hydrochloride (9h, SUVN-911) as a clinical candidate. Compound 9h is a potent α4β2 receptor ligand with a Ki value of 1.5 nM. It showed >10 μM binding affinity toward the ganglionic α3β4 receptor apart from showing selectivity over 70 other targets. It is orally bioavailable and showed good brain penetration in rats. Marked antidepressant activity and dose-dependent receptor occupancy in rats support its potential therapeutic utility in the treatment of depression. It does not affect the locomotor activity at doses several folds higher than its efficacy dose. It is devoid of cardiovascular and gastrointestinal side effects. Successful long-term safety studies in animals and phase-1 evaluation in healthy humans for safety, tolerability, and pharmacokinetics paved the way for its further development.

HEPATITIS C VIRUS INHIBITORS

The invention provides compounds of formulas (I) or (II): wherein the variables are defined in the specification, or a pharmaceutically-acceptable salt thereof, that are inhibitors of replication of the hepatitis C virus. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat hepatitis C viral infections, and processes and intermediates useful for preparing such compounds.

Practical asymmetric synthesis of both enantiomers of 6-(hydroxymethyl)piperidin-2-one

A practical asymmetric synthesis of both enantiomers of 6 (hydroxymethyl)piperidin-2-one 1 is described. Asymmetric dihydroxylation (AD) of alkenyl ester 2 using the (DHQ)2AQN ligand provides diol (5S)-3 in ≤95% ee after recrystallisation. This diol can subsequently be transformed into (6R)-1 using a five step reaction sequence. By employing (DHQD)2AQN [1,4-bis(dihydroquininyl)anthraquinone] in the initial AD reaction, (6S)-1 can be prepared in an analogous fashion.