Indanyl-substituted benzenecarboxamides, processes for their preparation, their use as a medicament, and pharmaceutical formulations containing them

A compound of formula I

• in which R(8) is either a 1-indanyl radical of formula II or a 2-indanyl radical of formula III
• and in which:
• R(1) and R(2), independently of one another, are R(20)-CrH2r,
• where at least one CH2 group of the group CrH2r is optionally replaced by —O—, —CH═CH—, —C≡C—, —CO—, —CO—O—, —O—CO—, —S—, —SO—, —SO2—, —NR(21)—, or —CONR(21);
• R(21) is hydrogen or alkyl having 1, 2, or 3 carbon atoms;
• R(20) is H, CH3, CH2F, CHF2, CF3, C2F5, C3F7, cycloalkyl having 3, 4, 5, 6, 7, or 8 carbon atoms, NR(22)R(23), —CONR(22)R(23), —OR(24), —COOR(24), phenyl, or an N-containing heterocycle having 1, 2, 3, 4, .5, 6, 7, 8, or 9 carbon atoms,
• where phenyl and the N-containing heterocycle are unsubstituted or substituted by 1 or 2 substituents selected from F, Cl, Br, I, CF3, NO2, CN, NH2, OH, methyl, ethyl, hydroxy-methyl, hydroxyethyl, methoxy, dimethylamino, sulfamoyl, methylsulfonyl, and methylsulfonylamino;
• R(22) and R(23), independently of one another, are hydrogen or alkyl having 1, 2, 3, or 4 carbon atoms;
• or
• R(22) and R(23) together form a chain of 4 or 5 methylene groups, of which one CH2 group is optionally replaced by —O—, —S—, —NH—, —N(methyl)—, or —N(benzyl)—;
• R(24) is hydrogen or alkyl having 1, 2, or 3 carbon atoms;
• r is 0, 1, 2, 3, 4, 5, 6, 7, or 8;
• or
• R(1) and R(2) together form a chain of 4 or 5 methylene groups, of which one CH2 group is optionally replaced by —O—, —S—, —NH—, —N(methyl)—, or —N(benzyl)—;
• R(3), R(4), R(5), and R(6), independently of one another, are hydrogen, F, Cl, Br, I, alkyl having 1, 2, 3, 4, or 5 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, or 8 carbon atoms, CN, CF3, NO2, OR(25), or NR(26)R(27);
• R(25) is hydrogen, alkyl having 1, 2, 3, or 4 carbon atoms, a fluorinated alkyl radical of formula —CxH2xCFyH3-y, or phenyl,
• in which phenyl is unsubstituted or substituted by 1 or 2 substituents selected from F, Cl, Br, I, CF3, NO2, CN, NH2, OH, methyl, ethyl, methoxy, dimethylamino, sulfamoyl, methyl-sulfonyl, and methylsulfonylamino;
• x is 0, 1, 2, or 3;
• y is 1, 2, or 3;
• R(26) and R(27), independently of one another, are hydrogen or alkyl having 1, 2, 3, or 4 carbon atoms;
• or
• R(26) and R(27) together form a chain of 4 or 5 methylene groups, of which one CH2 group is optionally replaced by —O—, —S—, —NH—, —N(methyl)—, or —N(benzyl)—;
• R(7) is hydrogen or alkyl having 1, 2, 3, or 4 carbon atoms;
• R(9) is hydrogen, OR(28), or OCOR(28);
• R(28) is hydrogen or alkyl having 1, 2, 3, or 4 carbon atoms;
• R(10) and R(11), independently of one another, are hydrogen or alkyl having 1, 2, 3, or 4 carbon atoms;
• R(12), R(13), R(14), and R(15), independently of one another, are hydrogen, F, Cl, Br, I, alkyl having 1, 2, 3, 4, or 5 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, or 8 carbon atoms, —CN, —CF3, —C2F5, —C3F7, —N3, —NO2, —Y—CsH2s—R(29), phenyl, thienyl, furyl, or an N-containing heterocycle having 1, 2, 3, 4, 5, 6, 7, 8, or 9 carbon atoms,
• where phenyl, thienyl, furyl, and the N-containing heterocycle are unsubstituted or substituted by 1 or 2 substituents selected from F, Cl, Br, I, CF3, NO2, CN, NH2, OH, methyl, ethyl, methoxy, dimethylamine, sulfamoyl, methylsulfonyl, and methylsulfonylamino;
• Y is —O—, —CO—, —CO—O—, —O—CO—, —S—, —SO—, —SO2—, —O—SO2—, —SO2NR(30)-, —CONR(30)—, or —NR(30)CO—, where the link to the backbone is in each case via the atom on the left;
• R(30) is hydrogen or alkyl having 1, 2, or 3 carbon atoms;
• s is 0, 1, 2, 3, 4, 5, or 6;
• R(29) is hydrogen, methyl, CF3, C2F5, C3F7, cycloalkyl having 3, 4, 5, 6, 7, or 8 carbon atoms, —OR(31), —COOR(31), —NR(32)R(33), —CONR(32)R(33), phenyl, or an N-containing heterocycle having 1, 2, 3, 4, 5, 6, 7, 8, or 9 carbon atoms,
• where phenyl and the N-containing heterocycle are unsubstituted or substituted by 1 or 2 substituents selected from F, Cl, Br, I, CF3, NO2, CN, NH2, OH, methyl, ethyl, methoxy, dimethylamino, sulfamoyl, methylsulfonyl, and methylsulfonylamino;
• R(31) is hydrogen or alkyl having 1, 2, or 3 carbon atoms;
• R(32) and R(33), independently of one another, are hydrogen or alkyl having 1, 2, 3, or 4 carbon atoms;
• or
• R(32) and R(33) together form a chain of 4 or 5 methylene groups, of which one CH2 group is optionally replaced by —O—, —S—, —NH—, —N(CH3)—, or —N(benzyl)—;
• or a physiologically tolerated salt thereof.