159390-33-7

Upstream product

• 108-43-0 3-monochlorophenol 
• 88-10-8 N,N-diethylcarbamyl chloride 

Downstream Products

• 211449-30-8 2-acetyl-3-chlorophenyl diethylcarbamate 
• 1245824-45-6 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl N,N-diethylcarbamate 
• 108-43-0 3-monochlorophenol 
• 164082-80-8 1-benzyl-2-ethyl-4-methoxy-1H-indole 
• 172732-68-2 ((3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)acetic acid 
• 172733-06-1 1-benzyl-2-ethyl-1H-indol-4-ol 
• 791642-67-6 1-chloro-2-iodo-3-methoxybenzene 
• 858854-82-7 3-chloro-2-iodo-phenol 
• 945470-36-0 2-but-1-ynyl-1-chloro-3-methoxybenzene 
• 945470-30-4 4-benzyloxy-2-butyl-1H-indole 
• 945470-24-6 1-benzyl-4-benzyloxy-2-butyl-1H-indole 
• 945470-22-4 1-benzyl-2-propyl-4-methoxy-1H-indole 
• 945470-21-3 1-benzyl-2-butyl-4-methoxy-1H-indole 
• 945470-11-1 1-benzyloxy-3-chloro-2-(1-hexynyl)benzene 

Relevant academic research and scientific papers

Synthesis and evaluation of novel stearoyl-CoA desaturase 1 inhibitors: 1′-{6-[5-(pyridin-3-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridazin-3-yl}-3, 4-dihydrospiro[chromene-2,4′-piperidine] analogs

In continuation of our investigation on novel stearoyl-CoA desaturase (SCD) 1 inhibitors, we have already reported on the structural modification of the benzoylpiperidines that led to a series of novel and highly potent spiropiperidine-based SCD1 inhibitors. In this report, we would like to extend the scope of our previous investigation and disclose details of the synthesis, SAR, ADME, PK, and pharmacological evaluation of the spiropiperidines with high potency for SCD1 inhibition. Our current efforts have culminated in the identification of 5-fluoro-1′-{6-[5-(pyridin-3-ylmethyl)-1,3,4-oxadiazol- 2-yl]pyridazin-3-yl}-3,4-dihydrospiro[chromene-2,4′-piperidine] (10e), which demonstrated a very strong potency for liver SCD1 inhibition (ID 50 = 0.6 mg/kg). This highly efficacious inhibition is presumed to be the result of a combination of strong enzymatic inhibitory activity (IC 50 (mouse) = 2 nM) and good oral bioavailability (F >95%). Pharmacological evaluation of 10e has demonstrated potent, dose-dependent reduction of the plasma desaturation index in C57BL/6J mice on a high carbohydrate diet after a 7-day oral administration (q.d.). In addition, it did not cause any noticeable skin abnormalities up to the highest dose (10 mg/kg).

Experimental and computational study of the 1,5-o → n carbamoyl snieckus-fries-type rearrangement

The reactions of o-lithiated O-aryl N,N-diethylcarbamates with different C-N multiple bond electrophiles have been thoroughly studied. A 1,5-O → N carbamoyl shift, a new variation of the anionic Fries-type rearrangement, takes place when nitriles, imines, or alkylcarbodiimides are employed. In these cases, the carbamoyl group plays a dual role as a directing group, building up a variety of functional groups through the 1,5-O → N carbamoyl migration. On the other hand, the use of iso(thio)cyanates and arylcarbodiimides led to non-rearranged o-functionalized Oarylcarbamates. This reactivity was further computationally explored, and the governing factor could be traced back to the relative basicity of the alternative products (migrated vs nonmigrated substrates). This exploration also provided interesting insights about the degree of complexation of the lithium cations onto these substrates. A new access to useful 2-hydroxybenzophenone derivatives has also been developed.

Access to Biphenyls by Palladium-Catalyzed Oxidative Coupling of Phenyl Carbamates and Phenols

The oxidative cross-coupling of phenols (3 equiv) to various substituted phenyl N, N -diethylcarbamates was explored with a variety of substrates. Pd(OAc) 2 was employed as the catalyst (20 molpercent) and K 2 S 2 O 8

Directed ortho-Metalation of Aryl Amides, O-Carbamates, and Methoxymethoxy Systems: Directed Metalation Group Competition and Cooperation

A systematic study on the competitive metalation of derivatives containing four directed metalation groups (DMGs), namely, Cl, OMe, methoxymethoxy (OMOM), and CONEt2, in comparison with the OCONEt2 DMG is described. In addition, the

1,5-O → N Carbamoyl Snieckus-Fries-Type Rearrangement

The reaction of o-lithiated O-aryl N,N-diethylcarbamates with (hetero)aromatic nitriles gives rise to functionalized salicylidene urea derivatives in high yields through a new 1,5-O → N carbamoyl migration. This Snieckus-Fries-type rearrangement nicely complements previously known O → C and O → O related shifts. In addition, when dimethylmalononitrile is used as the electrophilic partner, the carbamoyl shift is preferred over the expected transnitrilation reaction.

KINASE INHIBITOR

[Problem] To provide a novel PIM-3 inhibitor and a novel cancer therapeutic drug, in particular, a therapeutic drug for pancreatic cancer. [Solution] A PIM-3 kinase inhibitor comprising a compound represented by general formula (I) or a pharmacologically acceptable salt, hydrate or solvate thereof.

PYRIMIDINE DERIVATIVES FOR USE AS SPHINGOSINE 1-PHOSPHATE 1 (S1P1) RECEPTOR AGONISTS

Disclosed are pyrimidine derivatives for use as a sphingosine 1-phosphate 1 (S1P1) receptor agonists, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of conditions or diseases mediated by S1P1 receptors, particularly multiple sclerosis.

PYRIMIDINE DERIVATIVES FOR USE AS SPHINGOSINE 1-PHOSPHATE 1 (S1P1) RECEPTOR AGONISTS

Disclosed are pyrimidine derivatives for use as sphingosine 1- phosphate 1 (S1P1) receptor agonists, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of conditions or diseases mediated by S1P1 receptors, particularly multiple sclerosis.

THIENO [2, 3-B] PYRIDINE DERIVATIVES AS VIRAL REPLICATION INHIBITORS

The present invention relates to a series of compounds of formula (A) having antiviral activity, more specifically HIV (Human Immunodeficiency Virus) replication inhibiting properties. The invention also relates to methods for the preparation of such compounds, as well as to novel intermediates useful in one or more steps of such syntheses. The invention also relates to pharmaceutical compositions comprising an effective amount of such compounds as active ingredients. This invention further relates to the use of such compounds as medicines or in the manufacture of a medicament useful for the treatment of animals suffering from viral infections, in particular HIV infection. This invention further relates to methods for the treatment of viral infections in animals by the administration of a therapeutical amount of such compounds, optionally combined with one or more other drugs having anti-viral activity.

5-MEMBERED HETEROARYL DERIVATIVES USED AS SPHINGOSINE 1-PHOSPHATE RECEPTOR AGONISTS

5-membered heteroaryl derivatives of formula (I) or salts thereof, processes for their preparation, pharmaceutical compositions containing them and their uses in the treatment of various disorders mediated by S1P1 receptors are disclosed.