864710-29-2Relevant academic research and scientific papers
NEW BIARYL AMIDE DERIVATIVES
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Page/Page column 17, (2012/07/13)
The invention provides novel compounds having the general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 and A are as described herein, compositions including the compounds and methods of using the compounds.
Novel small molecule bradykinin B1 receptor antagonists. Part 1: Benzamides and semicarbazides
Schaudt, Marco,Locardi, Elsa,Zischinsky, Gunther,Stragies, Roland,Pfeifer, Jochen R.,Gibson, Christoph,Scharn, Dirk,Richter, Uwe,Kalkhof, Holger,Dinkel, Klaus,Schnatbaum, Karsten
scheme or table, p. 1225 - 1228 (2010/06/15)
The synthesis and SAR of two series of bradykinin B1 receptor antagonists is described. The benzamide moiety proved to be a suitable replacement for the aryl ester functionality of biaryl based antagonists. In addition, it was found that semica
Practical synthesis of a potent bradykinin B1 antagonist via enantioselective hydrogenation of a pyridyl N-acyl enamide
O'Shea, Paul D.,Gauvreau, Danny,Gosselin, Francis,Hughes, Greg,Nadeau, Christian,Roy, Amelie,Shultz, C. Scott
body text, p. 4547 - 4553 (2009/09/30)
(Chemical Equation Presented) A practical and efficient synthesis of bradykinin B1 antagonist 1 is described. A convergent strategy was utilized which involved synthesis of three fragments: 3, 6, and 7. Cross coupling of fragments 6 and 7 followed by amidation with 3 enabled efficient synthesis of 1 in 19 steps total, a 35% overall yield from commercially available pyridine 10. The key to the success of the synthesis was the development of a fluorodenitration step to install the fluorine in pyridine 7 and a catalytic enantioselective hydrogenation of N-acyl enamide 9 to set the stereochemistry.
A new class of bradykinin B1 receptor antagonists with high oral bioavailability and minimal PXR activity
Feng, Dong-Mei,DiPardo, Robert M.,Wai, Jenny M.,Chang, Ronald K.,Di Marco, Christina N.,Murphy, Kathy L.,Ransom, Richard W.,Reiss, Duane R.,Tang, Cuyue,Prueksaritanont, Thomayant,Pettibone, Douglas J.,Bock, Mark G.,Kuduk, Scott D.
, p. 682 - 687 (2008/09/19)
The design and synthesis of a novel class of human bradykinin B1 antagonists featuring difluoroethyl ether and isoxazole carboxamide moieties are disclosed. Compound 7g displayed excellent pharmacokinetic properties, efficient ex vivo receptor occupancy, and low potential for P450 induction via PXR activation.
