166735-47-3Relevant academic research and scientific papers
Design, Synthesis and Biological Evaluation of Neogliptin, a Novel 2-Azabicyclo[2.2.1]heptane-Based Inhibitor of Dipeptidyl Peptidase-4 (DPP-4)
Dahlén, Amelia D.,Gureev, Maxim A.,Kirichenko, Olga G.,Maslov, Ivan O.,Porozov, Yuri B.,Schi?th, Helgi B.,Shorshnev, Sergey V.,Trukhan, Mikhail V.,Trukhan, Vladimir M.,Tuaeva, Natalya O.,Zinevich, Tatiana V.
, (2022/03/02)
Compounds that contain (R)-3-amino-4-(2,4,5-trifluorophenyl)butanoic acid substituted with bicyclic amino moiety (2-aza-bicyclo[2.2.1]heptane) were designed using molecular modelling methods, synthesised, and found to be potent DPP-4 (dipeptidyl peptidase-4) inhibitors. Compound 12a (IC50 = 16.8 ± 2.2 nM), named neogliptin, is a more potent DPP-4 inhibitor than vildagliptin and sitagliptin. Neogliptin interacts with key DPP-4 residues in the active site and has pharmacophore parameters similar to vildagliptin and sitagliptin. It was found to have a low cardiotoxic effect compared to sitagliptin, and it is superior to vildagliptin in terms of ADME properties. Moreover, compound 12a is stable in aqueous solutions due to its low intramolecular cyclisation potential. These findings suggest that compound 12a has unique properties and can act as a template for further type 2 diabetes mellitus drug development.
SUBSTITUTED HETEROCYCLIC SULFONAMIDE COMPOUNDS USEFUL AS TRPA1 MODULATORS
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Paragraph 0811; 0812, (2015/04/28)
The invention is concerned with the compounds of formula I or II: and salts thereof. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula I or II as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.
BRIDGED RING COMPOUNDS AS HEPATITIS C VIRUS INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF
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Page/Page column 168; 169, (2014/09/16)
Provided herein is a compound of formula (I) or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, which can be used for treating HCV infection or a HCV disorder. Also provided herein are a pharmaceutical composition comprising the compound and the use of the compound and the pharmaceutical composition thereof, which can also be used for treating HCV infection or a HCV disorder.
FUSED TRICYCLIC COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES
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Page/Page column 100, (2011/08/04)
The present invention relates to novel Fused Tricyclic Compounds, compositions comprising at least one Fused Tricyclic Compound, and methods of using Fused Tricyclic Compounds for treating or preventing a viral infection or a virus-related disorder in a patient.
Tricycloundecane compounds useful as modulators of nuclear hormone receptor function
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Page/Page column 30, (2008/06/13)
Tricycloundecanes compounds, methods of using such compounds in the treatment of nuclear hormone receptor-associated conditions such as cancer and immune disorders, and pharmaceutical compositions containing such compounds are disclosed.
Azabicycloalkenes as synthetic intermediates: Application to the preparation of diazabicycloalkane scaffolds
Prenzel, Alexander H. G. P.,Deppermann, Nina,Maison, Wolfgang
, p. 1681 - 1684 (2007/10/03)
A general method to synthesize bicyclic dipeptide mimetics is reported. Key intermediates are azabicycloalkenes 9 and 17, which are prepared via Diels-Alder reactions and subsequent mild deprotection. These unsaturated bicyclic heterocycles are versatile
NOVEL COMPOUNDS OF PROLINE AND MORPHOLINE DERIVATIVES
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Page/Page column 66, (2008/06/13)
The present invention relates to compounds with the formulas (I), (II), and (III), or a pharmaceutically acceptable salt thereof: wherein T is a (4 to 10)-membered heterocyclyl selected from the group consisting of and wherein R1. R2 and R3 are as defined in the specification. The invention also relates to pharmaceutical compositions comprising the compounds of formulas (I), (II), and (III) and methods of treating a condition that is mediated by the modulation of the 11-β-hsd-1 enzyme, the method comprising administering to a mammal an effective amount of a compound of formulas (I), (II), and (III).
(1S, 3R, 4R)-2-azanorbornyl-3-methanol oxazaborolidines in the asymmetric reduction of ketones
Pinho, Pedro,Guijarro, David,Andersson, Pher G.
, p. 7897 - 7906 (2007/10/03)
Synthesis of new rigid (1S, 3R, 4R)-2-azanorbornyl-3-methanols and its application in the asymmetric borane reduction of ketones are described. The influence of temperature, solvent and concentration on the reation outcome were also studied and enantiomeric excess up to 89% could be obtained.
Reactions of ethyl 2-acetyl-2-azabicyclohept-5-ene-3-carboxylate and 4-acetylamino-2-oxabicyclooct-7-en-3-one with some electrophiles
Hursthouse, Michael B.,Malik, K. M. Abdul,Hibbs, David E.,Roberts, Stanley M.,Seago, Amanda J. H.,et al.
, p. 2419 - 2426 (2007/10/02)
The amide 3 reacted with various electrophilic reagents to give the addition products 5-9; reaction of 3 with m-chloroperoxybenzoic acid (MCPBA) gave the epoxide 10; similarly, the lactone 4 (an isomer of 3) reacted extremely selectively with a variety of electrophiles to give a range of polyfunctionalised bicyclic systems 12-15: reaction with MCPBA gave the epoxide 16 as the major product.
A Novel Skeletal Rearrangement of 2-Azabicyclohept-5-ene-3-carboxylic Acid Derivatives into 2-Oxabicyclo-oct-7-en-3-ones under Acidic Conditions
Kobayashi, Tomoshige,Ono, Katsuhiko,Kato, Hiroshi
, p. 61 - 65 (2007/10/02)
The reaction of ethyl 2-azabicyclohept-5-ene-3-carboxylate with aroyl chloride and the subsequent hydrolysis of the ester group provided 2-aroyl-2-azabicyclohept-5-ene-3-carboxylic acid derivatives, which underwent a stereospecific rearrange
