59954-73-3

Upstream product

• 138647-51-5 4-(4-methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 41979-39-9 4-piperidone hydrochloride 
• 5938-16-9 4-(4-methoxylphenyl)pyridine 
• 158984-57-7 1-(4-hydroxy-4-(4-methoxyphenyl)piperidin-1-yl)ethanone 
• 375853-82-0 tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 302924-67-0 tert-butyl 4-hydroxy-4-(4-methoxyphenyl)-1-piperidinecarboxylate 
• 138647-49-1 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 107336-07-2 2-{2-[4-(4-Methoxy-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethoxy}-benzaldehyde 
• 107336-08-3 2-{3-[4-(4-Methoxy-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-propoxy}-benzaldehyde 
• 437998-66-8 2-{4-[4-(4-methoxy-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-butyrylamino}-benzamide 
• 170857-30-4 1-[2-(Isochroman-1-yl)ethyl]-1,2,3,6-tetrahydro-4-(4-methoxyphenyl)pyridine hydrochloride 
• 158984-50-0 3-[4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridin-1-yl]methyl-1H-pyrrolo[2,3-b]pyridine 
• 35268-56-5 4'-{2-[4-(p-methoxyphenyl)-3,6-dihydro-1(2H)-pyridyl]ethoxy}acetanilide 
• 71916-59-1 4-(4-methoxyphenyl)-1,2,5,6-tetrahydro-1-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]pyridine 
• 1134111-38-8 C₁₃H₁₇NO₃S 
• 1350737-69-7 4-(4-methoxyphenyl)-2-phenylpyridine 
• 5938-16-9 4-(4-methoxylphenyl)pyridine 
• 1394387-87-1 N-((3-isopropylisoxazol-5-yl)methyl)-2-(4-(4-methoxyphenyl)-5,6-dihydropyridin-1(2H)-yl)ethanamine 
• 1574730-64-5 2-(4-(4-methoxyphenyl)-5,6-dihydropyridin-1(2H)-yl)ethanamine 
• 1574730-89-4 2-(2-(4-(4-methoxyphenyl)-5,6-dihydropyridin-1(2H)-yl)ethyl)isoindoline-1,3-dione 
• 1382321-69-8 2-{[4-(4-methoxyphenyl)-5,6-dihydropyridin-1(2H)-yl]-methyl}benzofuran-7-carboxamide 

Relevant academic research and scientific papers

Monoamine Oxidase (MAO-N) Whole Cell Biocatalyzed Aromatization of 1,2,5,6-Tetrahydropyridines into Pyridines

A sustainable MAO-N biocatalyzed process for the synthesis of pyridines from aliphatic tetrahydropyridines (THP) has been developed. Pyridine compounds were synthesized under mild reaction conditions and with high conversion, exploiting MAO-N whole cells as aromatizing biocatalysts. The kinetic profile of the whole cell biocatalytic transformation was finally investigated via in situ 19F NMR.

B(C6F5)3-Catalyzed Cascade Reduction of Pyridines

B(C6F5)3 has been found to be an effective catalyst for reduction of pyridines and other electron-deficient N-heteroarenes with hydrosilanes (or hydroboranes) and amines as the reducing reagents. The success of this development hinges upon the realization of a cascade process of dearomative hydrosilylation (or hydroboration) and transfer hydrogenation. The broad functional-group tolerance (e.g. ketone, ester, unactivated olefins, nitro, nitrile, heterocycles, etc.) implies high practical utility.

The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(III) complexes

A versatile palladium-free route for the synthesis of 4-aryl-substituted phenylpyridines (ppy), starting from tert-butyl 4-oxopiperidine-1-carboxylate, is reported. Reaction with an aryllithium, followed by trifluoroacetic acid dehydration/deprotection and oxidation with 2-iodoylbenzoic acid and finally phenylation, gave 4 ligands (L1-4H): 2,4-diphenylpyridine, 4-(4-methoxyphenyl)-2-phenylpyridine, 2-phenyl-4-(o-tolyl)pyridine and 4-mesityl-2-phenylpyridine. These ligands were coordinated to iridium to give the corresponding Ir(L)2(A) complexes (Ir1-7), where A = ancillary ligand acetylacetate or 2-picolinate. This was used to demonstrate that, through a combination of ancillary ligand choice and torsional twisting between the 4-aryl substituents of the ppy ligands, it is possible to tune the phosphorescent emission of the complexes in the range 502-560 nm.

Synthesis and biological evaluation of 1-(isoxazol-5-ylmethylaminoethyl)-4- phenyl tetrahydropyridine and piperidine derivatives as potent T-type calcium channel blockers with antinociceptive effect in a neuropathic pain model

New tetrahydropyridinyl and piperidinyl ethylamine derivatives were designed with hypothetical mapping on pharmacophore model generated from ligand-based virtual screening. The designed compounds were synthesized, and their inhibitory activities on T-type calcium channel were assayed using FDSS and patch-clamp assay. Among them, compounds 7b and 10b showed potent T-type calcium current blocking activity against Cav3.1 (α 1G) and Cav3.2 (α1H) channel simultaneously. With hERG and pharmacokinetics studies, compounds 7b and 10b were evaluated for the antinociceptive effect on rat model of neuropathic pain. They were significantly effective in decreasing the pain responses to mechanical and cold allodynia induced by spinal nerve ligation. These results suggest that modulation of α1G and α1H subtype T-type calcium channels may provide a promising approach for the treatment of neuropathic pain.

GLYCOSIDASE INHIBITORS

Compounds of formula (I) wherein X1, X2, W, R1 to R5, L and m have the meaning according to the claims, are glucosidase inhibitors, and can be employed, inter alia, for the treatment of Alzheimer's disease.

COMPOUNDS AND COMPOSITIONS AS MODULATORS OF GPR119 ACTIVITY

The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of GPR119.

Pd-catalyzed cross-coupling reactions with carbonyls: Application in a very efficient synthesis of 4-aryltetrahydropyridines

A method is proposed to prepare 4-aryltetrahydropyridines by a Pd-catalyzed cross-coupling reaction by using tosylhydrazone as the nucleophilic coupling agent without stoichiometric organometallic reagent. Palladium-catalyzed couplings can be used for the formation of C-C linkages. It was observed during study that tosylhydrazone can be generated by employing 4-piperidones directly in the cross-coupling reaction with tetrahydropyridines in very high yields. It was also found during study that the ketones and aldehydes can be employed as nucleophilic coupling partners in a reaction without using stoichiometric organometallic reagent. The study concluded that the method can be used to prepare different types of di- and trisubstituted olefins at large scale.

Design, synthesis, and evaluation of novel aryl-tetrahydropyridine PPARα/γ dual agonists

Aryl-tetrahydropyridine derivatives were prepared and their PPARα/γ dual agonistic activities were evaluated. Among them, compound (S)-5b was identified as a potent PPARα/γ dual agonist with an EC50 of 1.73 and 0.64 μM in hPPARα and γ, respectively. In diabetic (db/db) mice, compound (S)-5b showed good glucose lowering efficacy and favorable pharmacokinetic properties.

Design and synthesis of orally active inhibitors of TNF synthesis as anti-rheumatoid arthritis drugs

A novel series of TNF inhibitors was identified based on the screening of existing MMP inhibitor libraries. Further SAR optimization led to the discovery of a novel lead compound. Its synthesis, efficacy in experimental animal models, and pharmacokinetic

A versatile synthesis of 4-aryl tetrahydropyridines via palladium mediated Suzuki cross-coupling with cyclic vinyl boronates

A simple preparation of cyclic vinyl boronates derived from the vinyl triflates of N-protected tetrahydropyridines is described. Suzuki coupling of the boronates with aryl bromides, iodides and triflates proceeds in good yield to give 4-aryl tetrahydropyridines. (C) 2000 Elsevier Science Ltd.