C2-disubstituted indan-1-ones and their derivatives, processes for their preparation and their use as pharmaceuticals

A compound of the formula I

• 8
• wherein:
• R1, R2, R3, R4 independently of one another are H, F, Cl, Br, I, CN;
• N3, NO2, OH, O(C1-C8)-alkyl, O(C3-C8)-cycloalkyl, O—CH2-phenyl, O-phenyl, O—CO—(C1-C8)-alkyl, O—CO—(C3-C8)-cycloalkyl, S(O)0-2(C1-C8)-alkyl, S(O)0-2(C3-C8)-cycloalkyl, NH2, NH—(C1-C8)-alkyl, NH—(C3-C8)-cycloalkyl, N[(C1-C8)-alkyl]2, N[(C3-C8)-cycloalkyl]2, NH—CO—(C1-C8)-alkyl, NH—CO—(C3-C8)-cycloalkyl;
• SO3H, SO2—NH2, SO2-NH—(C1-C8)-alkyl, SO2—NH—(C3-C8)-cycloalkyl, NH—SO2—NH2, NH—SO2—(C1-C8)-alkyl, NH—SO2-(C3-C8)-cycloalkyl, O—CH2—COOH, O—CH2—CO—O(C1-C8)-alkyl, COOH, CO—O(C1-C8)-alkyl, CO—O—(C3-C8)-cycloalkyl, CO—NH2, CO—NH(C1-C8)-alkyl, CO—N[(C1-C8)-alkyl]2, (C1-C8)-alkyl, (C3-C8)cycloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, wherein on the alkyl, alkenyl and alkynyl groups, in each case, one to seven hydrogen atoms may be replaced by fluorine, or one hydrogen may be replaced by OH, OC(O)CH3, O—CH2-Ph, NH2, NH—CO—CH3 or N(COOCH2Ph)2;
• an aryl radical wherein the aryl radical is phenyl, or 1- or 2-naphthyl;
• or
• a heterocycle wherein the heterocycle is 5-tetrazolyl, 1-[(C1-C6)-alkyl]-5-tetrazolyl, 2-[(C1-C6)-alkyl]-5-tetrazolyl,
• 1-imidazolyl,
• 1- or 4-[1,2,4]-triazolyl,
• 2- or 3-thienyl,
• 2- or 3-furyl,
• 2-, 3- or 4-pyridyl,
• 2-, 4- or 5-oxazolyl,
• 3-, 4- or 5-isoxazolyl,
• 2-, 4- or 5-thiazolyl, or
• 3-, 4- or 5-isothiazolyl,
• where the aryl radical or heterocycle may be substituted up to two times by F, Cl, Br, CN, OH, (C1-C4)-alkyl, CF3, O—(C1-C4)-alkyl, S(O)0-2(C1-C6)-alkyl, NH2, NH—SO2—(C1-C4)-alkyl, COOH, CO—O—(C1-C4)-alkyl, or CO—NH2, and wherein on the alkyl groups, one to seven hydrogen atoms may be replaced by fluorine;
• X is S, SO, or SO2;
• Y is (CH2)p, where p may be 0, 1, 2 or 3;
• R5 is CF3, (C1-C18)-alkyl, (C3-C4)-cycloalkyl, or (C6-C8)-cycloalkyl, wherein, on the alkyl groups, one to seven hydrogen atoms may be replaced by fluorine;
• or R5 is
• (CH2)r—COR6, where r=1-6 and R6 may be OH, O—(C1-C6)-alkyl or NH2;
• or R5 is
• CH2—CH(NHR7)-COR8, where R7 may be H or C(O)—(C1-C4)-alkyl and R8 may be OH, O—(C1-C6)-alkyl or NH2;
• or R5 is
• Phenyl, 1- or 2-naphthyl, biphenyl or a heterocyclic radical, where the rings or ring systems of the phenyl, 1- or 2-naphthyl or heterocyclic radical may be substituted up to two times by F, Cl, Br, I, CN, OH, O(C1-C8)-alkyl, O(C3-C8)-cycloalkyl, O—CO—(C1-C8)-alkyl, O—CO—(C3-C8)-cycloalkyl, S(O)0-2(C1-C8)-alkyl, S(O)0-2(C3-C8)-cycloalkyl, NH2, NH—(C1-C8)-alkyl, NH—(C3-C8)-cycloalkyl, N[(C1-C8)-alkyl]2, N[(C3-C8)-cycloalkyl]2, NH—CO—(C2-C8)-alkyl, NH—CO—(C3-C8)-cycloalkyl;
• SO3H, SO2—NH2, SO2—NH—(C1-C8)-alkyl, SO2—NH—(C3-C8)-cycloalkyl;
• NH—SO2-NH2, NH—SO2—(C1-C8)-alkyl, NH—SO2—(C3-C8)-cycloalkyl, O—CH2—COOH, O—CH2—CO—O(C1-C8)-alkyl, COOH, CO—O(C1-C8)-alkyl, CO—O—(C3-C8)-cycloalkyl, CO—NH2, CO—NH(C1-C8)-alkyl, CO—N[(C1-C8)-alkyl]2, (C1-C8)-alkyl, or (C3-C8)-cycloalkyl, wherein on the alkyl groups, in each case, one to seven hydrogen atoms may be replaced by fluorine;
• R9 is F, Cl, Br, CN, CF3, (C1-C18)-alkyl, (C3-C4)-cycloalkyl, or (C6-C8)-cycloalkyl, wherein, on the alkyl groups, one to seven hydrogen atoms may be replaced by fluorine;
• or R9 is
• (CH2)r—COR6, where r=9-16 and R6 may be OH, O—(C1-C6)-alkyl or NH2;
• or R9 is
• CH2—CH(NHR7)-COR8 where R7 may be H or C(O)—(C1-C4)-alkyl and R8 may be OH, O—(C1-C6)-alkyl or NH2;
• or R9 is
• (CH2)u-aryl or (CH2)u-heteroaryl, where u is 0 to 6 and aryl may be phenyl, 1- or 2-napthyl, biphenyl or a heterocyclic radical, where the rings or ring systems of aryl, heteroaryl or the heterocyclic radical may be substituted up to two times by F, Cl, Br, I, CN, OH, O(C1-C8)-alkyl, O(C3-C8)-cycloalkyl, O—CO—(C1-C8)-alkyl, O—CO—(C3-C8)-cycloalkyl, S(O)0-2(C1-C8)-alkyl, S(O)0-2(C3-C8)-cycloalkyl, NH2, NH—(C1-C8)-alkyl, NH—(C3-C8)-cycloalkyl, N[(C1-C8)-alkyl]2, N[(C3-C8)-cycloalkyl]2, NH—CO—(C2-C8)-alkyl, NH—CO—(C3-C8)-cycloalkyl;
• SO3H, SO2—NH2, SO2—NH—(C1-C8)-alkyl, SO2—NH—(C3-C8)-cycloalkyl;
• NH—SO2—NH2, NH—SO2—(C1-C8)-alkyl, NH—SO2—(C3-C8)-cycloalkyl, O—CH2—COOH, O—CH2—CO—O(C1-C8)-alkyl, COOH, CO—O(C1-C8)-alkyl, CO—O—(C3-C8)-cycloalkyl, CO—NH2, CO—NH(C1-C8)-alkyl, CO—N[(C1-C8)-alkyl]2, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, wherein on the alkyl groups, in each case, one to seven hydrogen atoms may be replaced by fluorine;
• or a physiologically acceptable salt thereof;
• provided that when R1, R2, R3 and R4 are all hydrogen, and X—Y—R5 is S-phenyl, then R9 is other than phenyl.