US 7,541,361 B2
N-[4,5-diphenylpyrimidin-2-yl)methyl]amine derivatives, the preparation thereof and their therapeutic use
Francis Barth, Saint Georges d'Orques (France); Christian Congy, Saint Gely du Fese (France); Patrick Gueule, Teyran (France); and Murielle Rinaldi-Carmona, Saint Georges d'Orques (France)
Assigned to Sanofi-Aventis, Paris (France)
Filed on Jan. 03, 2008, as Appl. No. 11/968,855.
Application 11/968855 is a continuation of application No. PCT/FR2006/001621, filed on Jul. 06, 2006.
Claims priority of application No. 05 07359 (FR), filed on Jul. 08, 2005.
Prior Publication US 2008/0176867 A1, Jul. 24, 2008
Int. Cl. C07D 239/26 (2006.01); C07D 403/12 (2006.01); C07D 403/14 (2006.01); A61K 31/505 (2006.01); A61K 31/506 (2006.01); A61P 3/04 (2006.01)
U.S. Cl. 514—256  [544/242] 16 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Drawing
in which:
X represents a group

OG Complex Work Unit Drawing
R1 represents:
a (C1-C12)-alkyl, unsubstituted or substituted one or more times with substituents selected independently from a fluorine atom, a hydroxyl, a (C1-C4)-alkoxy, a (C1-C4)-alkylthio, a phenoxy, a trifluoromethoxy radical, a difluoromethoxy radical, a difluoromethylthio radical or a trifluoromethylthio radical;
a non-aromatic (C3-C12)-carbocyclic radical, unsubstituted or substituted one or more times with substituents selected independently from a (C1-C4)-alkyl, a (C1-C4)-alkoxy, a fluorine atom, a hydroxyl, a trifluoromethyl radical, a trifluoromethoxy radical or a (C1-C4)-alkylthio;
a (C3-C7)-cycloalkylmethyl, unsubstituted or substituted one or more times on the cycloalkyl with substituents selected independently from a (C1-C4)-alkyl, a (C1-C4)-alkoxy, a fluorine atom, a hydroxyl, a trifluoromethyl radical or a trifluoromethoxy radical;
a phenyl, unsubstituted or substituted one or more times with substituents selected independently from a halogen atom, a hydroxyl, an Alk group, an OAlk group, a methylenedioxy, a (C1-C4)-alkylamino, a di-(C1-C4)-alkylamino, a cyano, a nitro, an S(O)nAlk group, an OS(O)nAlk group, a (C1-C4)-alkylcarbonyl group; or from a phenyl, phenoxy, pyrrolyl, imidazolyl, pyridyl or pyrazolyl radical, said radical being unsubstituted or substituted one or more times with a (C1-C4)-alkyl;
a benzyl, unsubstituted or substituted one or more times on the phenyl with substituents selected independently from a halogen atom, an Alk group, a hydroxyl, an OAlk group, a methylenedioxy, an S(O)nAlk group or an OS(O)nAlk group and unsubstituted or substituted on alpha-methyl by one or two similar or dissimilar groups selected from a (C1-C4)-alkyl, a (C3-C7)-cycloalkyl;
a phenethyl, unsubstituted or substituted one or more times on the phenyl with substituents selected independently from a halogen atom, a (C1-C4)-alkyl, a (C1-C4)-alkoxy, a trifluoromethyl radical or a trifluoromethoxy radical;
a benzhydryl or a benzhydrylmethyl;
a 1,2,3,4-tetrahydronaphthalenyl, unsubstituted or substituted one or more times with a (C1-C4)-alkyl; or
an aromatic heterocyclic radical selected from pyrrolyl, imidazolyl, furyl, thienyl, pyrazolyl, oxazolyl, pyridyl, indolyl, said radical being unsubstituted or substituted one or more times with substituents selected independently from a halogen atom, a (C1-C4-alkyl, a (C1-C4-alkoxy, a trifluoromethyl radical, a trifluoromethoxy radical, a cyano, a nitro or a (C1-C4)-alkylthio;
R2 represents a hydrogen atom or a (C1-C3)-alkyl;
R3 represents a hydrogen atom or a (C1-C5)-alkyl;
R4 represents a phenyl, unsubstituted or substituted one or more times with substituents selected independently from a halogen atom, Alk group, OAlk group, S(O)nAlk group or OS(O)nAlk group;
R5 represents a phenyl, unsubstituted or substituted one or more times with substituents selected independently from a halogen atom, Alk group, OAlk group, S(O)nAlk group or OS(O)nAlk group;
R6 represents a hydrogen atom or a (C1-C3)-alkyl;
n represents 0, 1 or 2; and
Alk represents a (C1-C4)-alkyl, unsubstituted or substituted one or more times with a fluorine atom;
with the proviso that R4 and R5 do not simultaneously represent a phenyl substituted with a (C1-C4)-alkoxy.