132291-95-3

Usage

Uses

Used in Organic Synthesis:
Tetrahydropyran-4-ylmethyl methanesulfonate is used as a reagent for the protection and deprotection of alcohols and other functional groups in organic synthesis. Its high reactivity and selectivity make it an effective agent for these processes, facilitating the synthesis of complex organic molecules.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, Tetrahydropyran-4-ylmethyl methanesulfonate is utilized in the synthesis of various pharmaceuticals and fine chemicals. Its ability to protect and deprotect functional groups is crucial for the development of new drugs and the improvement of existing ones, ensuring the desired chemical properties and stability of the final products.

Upstream product

• 14774-37-9 (tetrahydro-2H-pyran-4-yl)methanol 
• 124-63-0 methanesulfonyl chloride 
• 110238-91-0 tetrahydropyran-4-carboxylic acid methyl ester 

Downstream Products

• 685885-75-0 N-(cyclopropylmethyl)-7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]pyrazolo[1,5-a]pyridin-3-amine 
• 1010833-70-1 3-(2-tert-Butyl-1-(tetrahydropyran-4-ylmethyl)-1H-imidazol-4-yl)benzonitrile 
• 745052-93-1 2-[4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)propionic acid 
• 745052-97-5 ethyl 2-(4-cyclopropanesulfonyl-phenyl)-3-(tetrahydropyran-4-yl)propionate 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of pyrazolo[3,4-d]pyrimidine-based protein kinase D inhibitors

The multiple roles of protein kinase D (PKD) in various cancer hallmarks have been repeatedly reported. Therefore, the search for novel PKD inhibitors and their evaluation as antitumor agents has gained considerable attention. In this work, novel pyrazolo[3,4-d]pyrimidine based pan-PKD inhibitors with structural variety at position 1 were synthesized and evaluated for biological activity. Starting from 3-IN-PP1, a known PKD inhibitor with IC50 values in the range of 94–108 nM, compound 17m was identified with an improved biochemical inhibitory activity against PKD (IC50 = 17–35 nM). Subsequent cellular assays demonstrated that 3-IN-PP1 and 17m inhibited PKD-dependent cortactin phosphorylation. Furthermore, 3-IN-PP1 displayed potent anti-proliferative activity against PANC-1 cells. Finally, a screening against different cancer cell lines demonstrated that 3-IN-PP1 is a potent and versatile antitumoral agent.

PYRIDIN-3-YL ACETIC ACID DERIVATIVES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

Disclosed are compounds of Formula (I), including pharmaceutically acceptable salts, pharmaceutical compositions comprising the compounds, methods for making the compounds and their use in inhibiting HIV integrase and treating those infected with HIV or AIDS.

CEREBLON BINDERS FOR THE DEGRADATION OF IKAROS

The present invention provides cereblon binders for the degradation of Ikaros or Aiolos by the ubiquitin proteasome pathway along with their use in therapeutic applications as described herein.

HYDROXYL PURINE COMPOUNDS AND USE THEREOF

Disclosed are a series of hydroxyl purine compounds and the use thereof as PDE2 or TNFα inhibitors, in particular, the compounds as shown in formula (I), or tautomers or pharmaceutically acceptable salts thereof.

Alkyl indole-based cannabinoid type 2 receptor tools: Exploration of linker and fluorophore attachment

Cannabinoid type 2 (CB2) receptor continues to emerge as a promising drug target for many diseases and conditions. New tools for studying CB2 receptor are required to further inform how this receptor functions in healthy and diseased states. The alkyl indole scaffold is a well-recognised ligand for cannabinoid receptors, and in this study the indole C5-7 positions were explored for linker and fluorophore attachment. A new high affinity, CB2 receptor selective inverse agonist was identified (16b) along with a general trend of C5-substituted indoles acting as agonists versus C7-substituted indoles acting as inverse agonists. The indole C7 position was found to be the most tolerant to linker extension and resulted in a high affinity inverse agonist with a medium length linker (19). Although a high affinity fluorescent ligand for CB2 receptor was not identified in this study, the indole C7 position shows great promise for fluorophore or probe attachment.

Discovery of Novel 1-Cyclopentenyl-3-phenylureas as Selective, Brain Penetrant, and Orally Bioavailable CXCR2 Antagonists

CXCR2 has emerged as a therapeutic target for not only peripheral inflammatory diseases but also neurological abnormalities in the central nervous system (CNS). Herein, we describe the discovery of a novel 1-cyclopentenyl-3-phenylurea series as potent and CNS penetrant CXCR2 antagonists. Extensive SAR studies, wherein molecules' property forecast index (PFI) was carefully optimized for overall balanced developability profiles, led to the discovery of the advanced lead compound 68 with a desirable PFI. Compound 68 demonstrated good in vitro pharmacology with excellent selectivity over CXCR1 and other chemokine receptors. Rat and dog pharmacokinetics (PK) revealed good oral bioavailability, high oral exposure, and desirable elimination half-life of the compound in both species. In addition, the compound demonstrated dose-dependent efficacy in the in vivo pharmacology neutrophil infiltration "air pouch" model in rodents after oral administration. Further, compound 68 is a CNS penetrant molecule with high unbound fraction in brain tissue.

BIARYL PYRAZOLES AS NRF2 REGULATORS

The present invention relates to biaryl pyrazole compounds, methods of making them, pharmaceutical compositions containing them and their use as NRF2 regulators.

NOVEL COMPOUNDS

The present invention is directed to novel retinoid-related orphan receptor gamma (RORγ) modulators, processes for their preparation, pharmaceutical compositions containing these modulators, and their use in the treatment of inflammatory, metabolic and autoimmune diseases mediated by RORγ.

1 -(CYCLOPENT-2-EN-1 -YL)-3-(2-HYDROXY-3-(ARYLSULFONYL)PHENYL)UREA DERIVATIVES AS CXCR2 INHIBITORS

The invention relates to 1-(3-sulfonylphenyl)-3-(cyclopent-2-en-1-yl)urea derivatives, and their use in treating or preventing diseases and conditions mediated by the CXCR2 receptor. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.

Scalable synthesis of a nonracemic α-arylpropionic acid via ketene desymmetrization for a glucokinase activator

Process research and development for a synthesis of the chiral carboxylic acid (R)-2 as a key intermediate of the glucokinase activator (R)-1 is described. The construction of the stereocenter at the α-carbon is a key point for the synthesis of (R)-2. The proposed process utilizes desymmetrization of a ketene in situ generated from the corresponding racemic carboxylic acid Rac-2 with (R)-pantolactone as a chiral auxiliary followed by hydrolysis of the resulting ester. This key step has been successfully scaled up to 20 kg, which demonstrates that this synthetic approach is comparable with a previously reported approach via enantioselective hydrogenation.