342603-10-5Relevant articles and documents
Synthesis of a 5-alkoxypyrido[3,4-d]pyrimidin-4(3H)-one derivative via directed ortho-metallation of a pyridine analogue
Dishington, Allan P.,Johnson, Paul D.,Kettle, Jason G.
, p. 3733 - 3735 (2004)
The synthetic strategy towards a 5-alkoxypyrido[3,4-d]pyrimidin-4(3H)-one is described, utilizing palladium catalyzed amination of a bromopyridine, and subsequent directed ortho-metallation/carboxylation as the key steps.
A multifunctional reagent designed for the site-selective amination of pyridines
Fier, Patrick S.,Kim, Suhong,Cohen, Ryan D.
, p. 8614 - 8618 (2020/06/05)
We report the development of a multifunctional reagent for the direct conversion of pyridines to Boc-protected 2-aminopyridines with exquisite site selectivity and chemoselectivity. The novel reagent was prepared on 200-g scale in a single step, reacts in the title reaction under mild conditions without precautions toward air or moisture, and is tolerant of nearly all common functionality. Experimental and in situ spectroscopic monitoring techniques provide detailed insights and unexpected findings for the unique reaction mechanism.
Process development of a novel azetidinyl ketolide antibiotic
Li, Bryan,Magee, Thomas V.,Buzon, Richard A.,Widlicka, Daniel W.,Bill, Dave R.,Brandt, Thomas,Cao, Xiaoping,Coutant, Michael,Dou, Haijian,Granskog, Karl,Flanagan, Mark E.,Hayward, Cheryl M.,Li, Bin,Liu, Fengwei,Liu, Wei,Nguyen, Thuy-Trinh,Raggon, Jeffrey W.,Rose, Peter,Rainville, Joseph,Reilly, Usa Datta,Shen, Yue,Sun, Jianmin,Wilcox, Glenn E.
scheme or table, p. 788 - 797 (2012/08/27)
Process development and the multikilogram synthesis of a novel azetidinyl ketolide antibiotic is described. Starting with clarithromycin, the eight-step synthesis features several telescoped operations and direct isolations, which results in a significant improvement in throughput and a major reduction in solvent usage and waste stream volume over the first scale-up campaign. Particular highlights of this effort include the development of an efficient synthesis of 3-hydroxy-1,5-naphthyridine-4-carbaldehyde via a Skraup process and engineering a robust final API synthesis. We also discovered a crystalline monotosylate salt that addressed significant formulation and degradation issues experienced when using the noncrystalline freebase.
Discovery of azetidinyl ketolides for the treatment of susceptible and multidrug resistant community-acquired respiratory tract infections
Magee, Thomas V.,Ripp, Sharon L.,Li, Bryan,Buzon, Richard A.,Chupak, Lou,Dougherty, Thomas J.,Finegan, Steven M.,Girard, Dennis,Hagen, Anne E.,Falcone, Michael J.,Farley, Kathleen A.,Granskog, Karl,Hardink, Joel R.,Huband, Michael D.,Kamicker, Barbara J.,Kaneko, Takushi,Knickerbocker, Michael J.,Liras, Jennifer L.,Marra, Andrea,Medina, Ivy,Nguyen, Thuy-Trinh,Noe, Mark C.,Obach, R. Scott,O'Donnell, John P.,Penzien, Joseph B.,Reilly, Usa Datta,Schafer, John R.,Shen, Yue,Stone, Gregory G.,Strelevitz, Timothy J.,Sun, Jianmin,Tait-Kamradt, Amelia,Vaz, Alfin D. N.,Whipple, David A.,Widlicka, Daniel W.,Wishka, Donn G.,Wolkowski, Joanna P.,Flanagan, Mark E.
experimental part, p. 7446 - 7457 (2010/06/13)
Respiratory tract bacterial strains are becoming increasingly resistant to currently marketed macrolide antibiotics. The current alternative telithromycin (1) from the newer ketolide class of macrolides addresses resistance but is hampered by serious safe
HIV INTEGRASE INHIBITORS
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Page/Page column 44, (2010/01/12)
Tricyclic compounds of Formula I are inhibitors of HIV integrase and inhibitors of HIV replication: (I) wherein G, T, R1, R2, R3A, R3B, R4A, R4B, R5A, R5B, R6A and R6B are defined herein. The compounds are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset or progression of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se (or as hydrates or solvates thereof) or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.