2'-substituted 1,1'-biphenyl-2-carboxamides, process for their preparation, their use as medicaments, and pharmaceutical preparations comprising them

A compound of the formula I,

• 228
• in which:
• R(1) is C(O)OR(9), SO2R(10), COR(11), C(O)NR(12)R(13) or C(S)NR(12)R(13);
• R(9) is CxH2x—R(14);
• x is 0, 1, 2, 3or 4,
• where x cannot be 0 if R(14) is OR(15) or SO2Me;
• R(14) is alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, 8, 9, 10 or 11 carbon atoms, CF3, C2F5, C3F7, CHF2, OR(15), SO2Me, phenyl, naphthyl, biphenylyl, furyl, thienyl or an N-containing heteroaromatic having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms,
• where phenyl, naphthyl, biphenylyl, furyl, thienyl and the N-containing hetero-aromatic are unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of F, Cl, Br, I, OCF3, CF3, NO2, CN, COOMe, CONH2, COMe, NH2, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino;
• R(15) is alkyl having 1, 2, 3, 4 or 5 carbon atoms, cycloalkyl having 3, 4, 5 or 6 carbon atoms, CF3 or phenyl which is unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of F, Cl, Br, I, CF3, NO2, CN, COOMe, CONH2, COMe, NH2, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino;
• R(10), R(11) and R(12)
• independently of one another are defined as R(9);
• R(13) is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or CF3;
• R(2) is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or CF3;
• R(3) is CyH2y—R(16);
• y is 0, 1, 2, 3 or 4,
• where y cannot be 0 if R(16) is OR(17) or SO2Me;
• R(16) is alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, 8, 9, 10 or 11 carbon atoms, CF3, C2F5, C3F7, CH2F, CHF2, OR(17), SO2Me, phenyl, naphthyl, furyl, thienyl or an N-containing heteroaromatic having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms,
• where phenyl, naphthyl, furyl, thienyl and the N-containing heteroaromatic are unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of F, Cl, Br, I, CF3, OCF3, NO2, CN, COOMe, CONH2, COMe, NH2, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino;
• R(17) is hydrogen, alkyl having 1, 2, 3, 4 or 5 carbon atoms, cycloalkyl having 3, 4, 5 or 6 carbon atoms, CF3, phenyl or 2-, 3- or 4-pyridyl,
• where phenyl or 2-, 3- or 4-pyridyl are unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of F, Cl, Br, I, CF3, OCF3, NO2, CN, COOMe, CONH2, COMe, NH2, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino;
• or
• R(3) is CHR(18)R(19);
• R(18) is hydrogen or CzH2z—R(16), where R(16) is defined as indicated above;
• z is 0, 1, 2or 3;
• R(19) is COOH, CONH2, CONR(20)R(21), COOR(22), or CH2OH;
• R(20) is hydrogen, alkyl having 1, 2, 3, 4 or 5 carbon atoms, CvH2v—CF3 or CwH2w-phenyl,
• where the phenyl ring is unsubstituted or substituted by 1, 2 or 3 substitutents selected from the group consisting of F, Cl, Br, I, CF3, NO2, CN, COOMe, CONH2, COMe, NH2, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino;
• v is 0, 1, 2 or 3;
• w is 0, 1, 2 or 3;
• R(21) is hydrogen or alkyl having 1, 2, 3, 4 or 5 carbon atoms;
• R(22) is alkyl having 1, 2, 3, 4 or 5 carbon atoms;
• R(4) is hydrogen, alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms or CF3;
• or
• R(3) and R(4)
• together are a chain of 4 or 5 methylene groups, of which one methylene group can be replaced by —O—, —S—, —NH—, —N(methyl)- or —N(benzyl)-;
• R(5), R(6), R(7) and R(8)
• independently of one another are hydrogen, F, Cl, Br, I, CF3, NO2, CN, COOMe, CONH2, COMe, NH2, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl or methylsulfonylamino;
• R(30) and R(31)
• independently of one another hydrogen or alkyl having 1, 2 or 3 carbon atoms;
• or
• R(30) and R(31)
• together form a chain of 2 methylene groups;
• or a pharmaceutically acceptable salt thereof.