252199-28-3

Usage

Uses

Used in Pharmaceutical Research:
4-(Benzyloxy)-N-methoxy-N-methylbenzamide is used as a precursor in the development of sulfonamide photoaffinity inhibitors for probing cellular γ-Secretase. This application is significant because γ-Secretase is an enzyme complex involved in the proteolytic processing of amyloid precursor protein (APP), which is linked to the pathogenesis of Alzheimer's disease. By developing inhibitors that target this enzyme, researchers aim to modulate its activity and potentially develop therapeutic strategies for treating Alzheimer's and other related neurodegenerative disorders.

InChI:InChI=1/C16H17NO3/c1-17(19-2)16(18)14-8-10-15(11-9-14)20-12-13-6-4-3-5-7-13/h3-11H,12H2,1-2H3

Upstream product

• 1486-50-6 4-(benzyloxy)benzoic acid chloride 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 56442-22-9 benzyl 4-benzyloxybenzoate 
• 1486-51-7 p-(benzyloxy)benzoic acid 
• 6793-92-6 p-benzyloxyphenylbromide 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 99-96-7 4-hydroxy-benzoic acid 
• 100-39-0 benzyl bromide 

Downstream Products

• 885694-14-4 [4-(benzyloxy)phenyl][1-cyclopentyl-7-(trifluoromethyl)-1H-indazol-3-yl]methanone 
• 171001-06-2 1-(4-(benzyloxy)phenyl)-2-(pyridin-4-yl)ethanone 
• 51345-76-7 1-(dimethylamino)-3-<4-(benzyloxy)phenyl>propan-3-one 
• 898563-25-2 4-[3-(4-benzyloxy-phenyl)-1-methyl-1H-pyrazol-4-yl]-pyridine 
• 1521138-27-1 2-(3-(4-(benzyloxy)phenyl)-4-(pyridin-4-yl)-1H-pyrazol-1-yl)ethanol 
• 137614-78-9 1-(4-(benzyloxy)phenyl)-2,2,2-trifluoroethan-1-one 
• 460747-45-9 4-hydroxy-3-iodo-N-methoxy-N-methylbenzamide 
• 460747-44-8 4-hydroxy-N-methoxy-N-methylbenzamide 
• 1521139-37-6 2-((4-(1-(2-fluoroethyl)-4-(pyridin-4-yl)-1H-pyrazol-3-yl)phenoxy)methyl)quinazoline 
• 1521139-28-5 3-methyl-2-((4-(1-methyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl)phenoxy)methyl)quinazolin-4(3H)-one 
• 1521139-25-2 2-((4-(1-(2-fluoroethyl)-4-(pyridin-4-yl)-1H-pyrazol-3-yl)phenoxy)methyl)benzo[d]oxazole 
• 1521139-22-9 2-((4-(1-(2-fluoroethyl)-4-(pyridin-4-yl)-1H-pyrazol-3-yl)phenoxy)methyl)-1,5-naphthyridine 

Relevant academic research and scientific papers

Access to Aryl and Heteroaryl Trifluoromethyl Ketones from Aryl Bromides and Fluorosulfates with Stoichiometric CO

We report a sequential one-pot preparation of aromatic trifluoromethyl ketones starting from readily accessible aryl bromides and fluorosulfates, the latter easily prepared from the corresponding phenols. The methodology utilizes low pressure carbon monoxide generated ex situ from COgen to generate Weinreb amides as reactive intermediates that undergo monotrifluoromethylation affording the corresponding aromatic trifluoromethyl ketones (TFMKs) in good yields. The stoichiometric use of CO enables the possibility for accessing 13C-isotopically labeled TFMK by switching to the use of 13COgen.

Synthesis and in vitro biological evaluation of pyrazole group-containing analogues for PDE10A

Twenty eight new analogues were synthesized by optimizing the structure of MP-10 and their in vitro binding affinities towards PDE10A, PDE3A/B, and PDE4A/B were determined. Among these new analogues, 10a, 10b, 10d, 11a, 11b and 11d are very potent towards PDE10A and have IC50 values of 0.40 ± 0.02, 0.28 ± 0.06, 1.82 ± 0.25, 0.24 ± 0.05, 0.36 ± 0.03 and 1.78 ± 0.03 nM respectively; these six compounds displayed high selectivity for PDE10A versus PDE3A/3B/4A/4B. The promising compounds will be further validated in vivo to identify PDE10A imaging tracers. The Royal Society of Chemistry.

RADIOLABELED PDE10A LIGANDS

Compounds of formula (I) are disclosed Compounds of formula (I) are useful in treating conditions and disorders prevented by or ameliorated by PDE10A ligands. Radiolabeled compounds of formula (I) are also useful as diagnostic tools as PDE10A positron emi

Synthesis and pharmacological evaluation of 3-aryl-3-azolylpropan-1-amines as selective triple serotonin/norepinephrine/dopamine reuptake inhibitors

A series of 3-aryl-3-azolylpropan-1-amines was prepared and screened for its capability of inhibiting monoamine reuptake. Analogs with nanomolar potency, good human in vitro microsomal stability, and low drug-drug interaction potential were described. In

Discovery of a novel class of phosphodiesterase 10A inhibitors and identification of clinical candidate 2-[4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3- yl)-phenoxymethyl]-quinoline (PF-2545920) for the treatment of schizophrenia

By utilizing structure-based drug design (SBDD) knowledge, a novel class of phosphodiesterase (PDE) 10A inhibitors was identified. The structure-based drug design efforts identified a unique "selectivity pocket" for PDE10A inhibitors, and interactions within this pocket allowed the design of highly selective and potent PDE10A inhibitors. Further optimization of brain penetration and drug-like properties led to the discovery of 2-[4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline (PF-2545920). This PDE10A inhibitor is the first reported clinical entry for this mechanism in the treatment of schizophrenia.

BICYCLIC HETEROARYL COMPOUNDS AS PDE10 INHIBITORS

The invention pertains to bicyclic heteroaryl compounds that serve as effective phosphodiesterase (PDE) inhibitors The invention also relates to compounds which are selective inhibitors of PDE-10. The invention further relates to intermediates for prepara

Heteroaromatic quinoline compounds

The invention pertains to heteroaromatic compounds that serve as effective phosphodiesterase (PDE) inhibitors. In particular, the invention relates to said compounds which are selective inhibitors of PDE10. The invention also relates to intermediates for preparation of said compounds; pharmaceutical compositions comprising said compounds; and the use of said compounds in a method for treating certain central nervous system (CNS) or other disorders.

4-(2-[2-(2(R)-Methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention

H3 receptor antagonists based on a 2-aminoethylbenzofuran skeleton have been discovered, which are potent in vitro at human and rat H 3 receptors, with Ki values of 0.1-5.8 nM. Analogues were discovered with potent (0.01-1 mg/kg) cognition and attention enhancing properties in animal models. One compound in particular, 4-(2-[2-(2(R)- methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile (ABT-239), combined potent and selective H3 receptor antagonism and excellent pharmacokinetic and metabolic properties across species, with full efficacy in two behavioral models: a five-trial inhibitory avoidance acquisition model in rat pups at 0.1 mg/kg and a social recognition memory model in adult rats at 0.01 mg/kg. Furthermore, this compound did not stimulate locomotor activity and showed high selectivity for the induction of behavioral efficacy versus central nervous system based side effects. The potency and selectivity of this compound and of analogues from this class support the potential of H3 receptor antagonists for the treatment of cognitive dysfunction.

Fused-ring compounds and use thereof as drugs

The present invention provides a fused ring compound of the following formula [I] wherein each symbol is as defined in the specification, a pharmaceutically acceptable salt thereof, and a therapeutic agent for hepatitis C, which contains this compound. Th

Structure - Activity relationships of non-imidazole H3 receptor ligands. Part 1

SAR studies for novel non-imidazole containing H3 receptor antagonists with high potency and selectivity for rat H3 receptors are described. A high throughput screening lead, A-923, was further elaborated in a systematic manner to clarify a pharmacophore for this class of aryloxyalkyl piperazine based compounds.