1,4-dihydropyridine compounds as bradykinin antagonists

Details 1,4-dihydropyridine compounds as bradykinin antagonists 1,4-dihydropyridine compounds as bradykinin antagonists

C - Chemistry, Metallurgy

07

D

C07D 211/90 (2006.01) A61K 31/495 (2006.01) C07D 405/12 (2006.01) C07D 409/12 (2006.01) C07D 451/04 (2006.01) C07D 453/02 (2006.01)

Patent

CA 2245857

Disclosed are novel dihydropyridine compounds of the formula (I): (see formula I) and their pharmaceutically acceptable salts, wherein A1 and A2 are each halo; X is CO, S(O)2 or S(O)-(CH2)n wherein S atom is directly attached to the phenyl and n is 0, 1 or 2; and R1 is 8-azabicyclo[3.2.1]octyl, quinuclidinyl, bicyclo [3.3.0]octyl, C3-10 cycloalkyl, 2,3,5,6-tetrahydro-4H- thiopyranyl or C3-6 cycloalkyl-C1-4 alkyl, optionally substituted with C1-4 alkyl, hydroxy, dioxolanespiro or oxo. The novel dihydropyridine compounds have excellent bradykinin antagonistic activity and are thus useful for the treatment of medical conditions caused by bradykinin such as inflammation, cardiovascular disease, pain, common cold, allergies, asthma, pancreatitis, burns, virus infection, head injury, multiple trauma or the like in mammalian, especially humans.

L'invention a trait à un composé de la formule (I) ainsi qu'à ses sels acceptables du point de vue pharmaceutique. Dans cette formule, A<1> et A<2> représentent chacun un halo, X représente CO, S(O)2 ou S(O)-(CH2)n où un atome de S est directement lié au phényle et où n vaut 0 ou 2. Dans cette même formule (I), R<1> représente un 8-azabicyclo[3.2.1] octyle, un quinuclidinyle, un bicyclo[3.3.0] octyle, un cycloalkyle comportant de 3 à 10 atomes de carbone, un 2,3,5,6-tétrahydro-4H-thiopyranyle ou un cycloalkyl-C1-4 alkyle comportant de 3 à 6 atomes de carbone, éventuellement substitué par un alkyle comportant de 1 à 4 atomes de carbone, un hydroxy, un dioxaranyle ou un oxo. Les nouveaux composés à base de dihydropyridine décrits dans cette invention, qui se révèlent comme de remarquables antagonistes de la bradykinine, sont des plus utiles dans le traitement d'inflammations, de maladies cardio-vasculaires, de la douleur, du rhume banal, d'allergies, de l'asthme, de pancréatites, de brûlures, d'infections virales, de traumatismes crâniens, de traumatismes multiples ou analogue, chez les mammifères et notamment, les humains.

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