573675-25-9Relevant articles and documents
NEW BIARYL AMIDE DERIVATIVES
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Page/Page column 22, (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.
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
supporting information; experimental part, 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.
Bradykinin B1 antagonists: Biphenyl SAR studies in the cyclopropanecarboxamide series
Kuduk, Scott D.,DiPardo, Robert 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.
, p. 3608 - 3612 (2008/02/08)
SAR study of the biphenyl region of cyclopropanecarboxamide derived bradykinin B1 antagonists was examined. Incorporation of a pyridine in place of the proximal phenyl ring and chlorination of the distal phenyl ring proved to be well tolerated
