1-hydroxycycloalkanecarboxamide derivatives as bradykinin...

Details 1-hydroxycycloalkanecarboxamide derivatives as bradykinin... 1-hydroxycycloalkanecarboxamide derivatives as bradykinin...

C - Chemistry, Metallurgy

07

D

C07D 401/10 (2006.01) A61K 31/4418 (2006.01) A61K 31/4439 (2006.01) C07D 213/61 (2006.01) C07D 413/10 (2006.01)

Patent

CA 2610059

.alpha.-Hydroxycycloalkanecarboxamide derivatives of formula (I) or a pharmaceutically acceptable salt thereof, wherein formula (a) is a single or double bond; Rl, R2 and R3 are each independently selected from H, halogen and OH; or Rl and R2 attached to the same carbon atom together represent oxo; R4 is H or methyl; R5 is Cl or F; R6 is selected from -CO2-C1-4alkyl, -O-C1- 4alkyl, -O- C1-4haloalkyl, 2-methyltetrazol-5-yl, 5-methyl l,2,4-oxadiazol-3- yl, 3-methyl-1,2,4-oxadiazol-5-yl, 5-halomethyl-l,2,4-oxadiazol-3-yl, 3- halomethyl- l,2,4-oxadiazol-5-yl, tetrazol-5-yl, 5-halomethyl-l,2,3-triazolyl, and 5-methyl-l ,2,3-triazolyl; R7 and R8 are each independently Cl or F; and n is 0 or 1, are bradykinin B1 antagonists or inverse agonists useful in the treatment or prevention of symptoms such as pain and inflammation associated with the bradykinin B1 pathway.

L'invention concerne des dérivés de .alpha.-hydroxycycloalcanecarboxamide de formule (I) ou un sel pharmaceutiquement acceptable de ceux-ci. Dans cette formule, (a) désigne une liaison simple ou double; R1, R2 et R3 sont chacun indépendamment sélectionnés parmi : H, halogène et OH; ou R1 et R2 fixés sur le même atome de carbone désignent ensemble oxo; R4 désigne H ou méthyle; R5 désigne Cl ou F; R6 est sélectionné parmi: -CO2- alkyle C1-4, -O- alkyle C1-4, -O- haloalkyle C1-4, 2-méthyltétrazol-5-yl, 5-méthyl-1,2,4-oxadiazol-3-yl, 3-méthyl-1,2,4-oxadiazol-5-yl, 5-halométhyl-1,2,4-oxadiazol-3-yl, 3-halométhyl-1,2,4-oxadiazol-5-yl, tétrazol-5-yl, 5-halométhyl-1,2,3-triazolyle, et 5-méthyl-1,2,3-triazolyle; R7 et R8 désignent chacun indépendamment Cl ou F; et n désigne 0 ou 1. Les dérivés et les sels de l'invention sont des antagonistes de la bradykinine B1 ou des agonistes inverses utiles de celle-ci pour traiter ou pour prévenir des symptômes, notamment des douleurs et des inflammations associées à la voie de la bradykinine B1.

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