6191-98-6Relevant academic research and scientific papers
TETRAHYDROPYRAZOLO-PYRAZINYL-DIHYDROIMIDAZOLONE OR TETRAHYDROPYRAZOLO-PYRIDINYL-DIHYDROIMIDAZOLONE COMPOUNDS AND METHODS OF USING SAME
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Paragraph 00636, (2022/02/05)
The application relates to a compound of Formula (I) : or a pharmaceutically acceptable salt, hydrate, solvate, prodrug, stereoisomer, or tautomer thereof, which modulates the activity of GLP-1 receptor, a pharmaceutical composition comprising a compound of Formula (I), and a method of treating or preventing a disease in which GLP-1 receptor plays a role.
Metal-Free Stereoselective Synthesis of (E)- And (Z)-N-Monosubstituted β-Aminoacrylates via Condensation Reactions of Carbamates
Pollack, Scott R.,Dion, Amélie
, p. 11748 - 11762 (2021/09/07)
N-monosubstituted β-aminoacrylates are building blocks, which have been used in the preparation of amino acids and pharmaceuticals. Two efficient, stereoselective methods of preparation, via acid- or base-promoted condensation reactions of carbamates, are described. The base-promoted reaction is E-selective, while acid catalysis can, through the choice of solvent, selectively form E or Z. The acid-catalyzed E-selective process proceeds through a crystallization obviating the need for chromatographic purification.
Development of the large-scale synthesis of tetrahydropyran glycine, a precursor to the HCV NS5A inhibitor BMS-986097
Mathur, Arvind,Wang, Bei,Smith, Daniel,Li, Jianqing,Pawluczyk, Joseph,Sun, Jung-Hui,Wong, Michael Kwok,Krishnananthan, Subramaniam,Wu, Dauh-Rurng,Sun, Dawn,Li, Peng,Yip, Shiuhang,Chen, Bang-Chi,Baran, Phil S.,Chen, Qi,Lopez, Omar D.,Yong, Zhong,Bender, John A.,Nguyen, Van N.,Romine, Jeffrey L.,St Laurent, Denis R.,Wang, Gan,Kadow, John F.,Meanwell, Nicholas A.,Belema, Makonen,Zhao, Rulin
, p. 10376 - 10387 (2018/05/31)
An efficient large-scale synthesis of acid 1, a penultimate precursor to the HCV NS5A inhibitor BMS-986097, along with the final API step are described. Three routes were devised for the synthesis of 1 at the various stages of the program. The third generation route, the one that proved scalable and is the main subject of this paper, features a one-step Michael addition of t-butyl 2-((diphenylmethylene)amino)acetate (24) to (E)-benzyl 4-(1-hydroxycyclopropyl)but-2-enoate (28) followed by cyclization and chiral separation to form 27c, the core skeleton of cap piece 1. The epimerization and chiral resolution of 27c followed by further synthetic manipulations involving the carbamate formation, lactone reduction and cyclization, afforded cyclopropyl pyran 1. A detailed study of diphenylmethane deprotection via acid hydrolysis as well as a key lactone to tetrahydropyran conversion, in order to avoid a side reaction that afforded an alternative cyclization product, are discussed. This synthesis was applied to the preparation of more than 100 g of the final API BMS-986097 for toxicology studies.
Synthesis of functionalized γ-lactone via Sakurai exo -cyclization/rearrangement of 3,3-bis(silyl) enol ester with a tethered acetal
Yin, Zhiping,Liu, Zengjin,Huang, Zhenggang,Chu, Yang,Chu, Zhiwen,Hu, Jia,Gao, Lu,Song, Zhenlei
supporting information, p. 1553 - 1556 (2015/03/30)
An efficient synthesis of functionalized γ-lactones has been developed involving Sakurai exo-cyclization/rearrangement of 3,3-bis(silyl) enol esters with a tethered acetal. While the steric and electronic effects of geminal bis(silane) favor the desired Sakurai pathway, the methoxy species formed in the deprotection step also facilitates both cyclization and rearrangement. The synthetic value of this approach has been demonstrated by efficiently transforming the E-vinylsilane into enyne and the γ-lactone moiety into multisubstituted THF.
HEPATITIS C VIRUS INHIBITORS
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Page/Page column 49, (2014/05/24)
The present disclosure relates to compounds, compositions and methods for the treatment of Hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.
Bronsted acid mediated cyclization of enaminones. Rapid and efficient access to the tetracyclic framework of the strychnos alkaloids
Edwankar, Rahul V.,Edwankar, Chitra R.,Namjoshi, Ojas A.,Deschamps, Jeffrey R.,Cook, James M.
supporting information; experimental part, p. 181 - 188 (2012/05/19)
The development of an efficient diastereoselective method that permits rapid construction of the tetracyclic core 17 of the Strychnos-Aspidosperma alkaloids is described. Enaminone 16, synthesized in high yield, has been cyclized under the influence of a Bronsted acid to provide the core tetracyclic framework 17 of the Strychnos alkaloids in optically active form or alternatively to the β-ketoester tetrahydro-β-carboline (THBC) unit 18, by varying the equivalents of acid and the molar concentration. Attempts to utilize 18 to form the C(7)-C(16) bond of the akuammiline related alkaloids represented by strictamine (22), using metal-carbenoid chemistry, are also described.
HEPATITIS C VIRUS INHIBITORS
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Page/Page column 49, (2012/12/13)
The present disclosure relates to compounds, compositions and methods for the treatment of Hepatitis C virus (HCV) infection of following Fomula (I). Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.
NOVEL HETEROCYCLYL COMPOUNDS
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Page/Page column 48, (2010/02/17)
The invention is concerned with novel heterocyclyl compounds of formula (I): wherein A, X, R3, R4, R5, R6, R7, R8, R9, R10, m, n and p are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds are antagonists of CCR2 receptor, CCR5 receptor and/or CCR3 receptor and may be used as medicaments.
Highly stereoselective hydrogenations-as key-steps in the total synthesis of statins
Andrushko, Natalia,Andrushko, Vasyl,Tararov, Vitali,Korostylev, Andrei,Koenig, Gerd,Boerner, Armin
scheme or table, p. 534 - 541 (2010/08/20)
Statins are inhibitors of 3-hydroxy-3-methyl-glutaryl coenzyme A reductase (HMG-CoA reductase) and became the standard of care for treatment of hypercholesterolemia because of their efficacy, safety, and long-term benefits. They are administered as diaste
CARBOXAMIDE COMPOUNDS AND THEIR USE AS ANTAGONISTS OF THE CHEMOKINE CCR2 RECEPTOR
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Page/Page column 65-66, (2009/07/17)
Chemokine receptor antagonists, in particular, compounds of Formula (I) that act as antagonists of the chemokine CCR2 receptor, including pharmaceutical compositions and uses thereof to treat or prevent diseases associated with monocyte accumulation, lymphocyte accumulation or leukocyte accumulation are described; wherein (B/A) is an optionally substituted fused aromatic or partially aromatic bicyclic ring containing at least one nitrogen atom.
