Polysubstituted indan-1-ol systems for the prophylaxis or treatment of obesity

A compound of the formula I,

• 7
• in which
• 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, wherein the alkyl radicals up to seven hydrogen atoms may be replaced by fluorine;
• S(O)0-2(C1-C8)-alkyl, S(O)0-2(C3-C8)-cycloalkyl, wherein the alkyl radicals up to seven hydrogen atoms may be replaced by fluorine;
• NH2, NH—(C1-C8)-alkyl, NH—(C3-C8)-cycloalkyl, N[(C1-C8)-alkyl]2, N[(C3-C8)-cycloalkyl]2, NH—CO—(C1-C8)-alkyl, or NH—CO—(C3-C8)-cycloalkyl;
• SO3H;
• SO2—NH2, SO2—NH—(C1-C8)-alkyl, SO2—NH—(C3-C8)-cycloalkyl;
• SO2—(C1-C6)-alkyl NH—SO2—NH2;
• NH—SO2—(C1-C8)-alkyl, NH—SO2—(C3-C8)-cycloalkyl;
• O—CH2—COOH, O—CH2—CO—O(C1-C8)-alkyl, COOH, COO(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, or (C2-C8)-alkynyl, wherein the alkyl, alkenyl and alkynyl groups 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;
• phenyl, 1- or 2-naphthyl,
• 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, CO—NH2 and wherein the alkyl groups one to seven hydrogen atoms may be replaced by fluorine;
• or
• R2 and R3 together form the radical —O—CH2—O—;
• X is S, SO, or SO2;
• Y is (CH2)p, wherein p may be 0, 1, 2 or 3;
• R5 is (C1-C18)-alkyl, or (C3- C8)-cycloalkyl,
• wherein the alkyl groups up to seven hydrogen atoms may be replaced by fluorine;
• (CH2)1-6—COOH, (CH2)1-6—COO—(C1-C6)-alkyl, (CH2)1-6—CONH2;
• CH2—CH(NHR10)-COR11, where R10 may be H or C(O)—(C1-C6)-alkyl and R11 may be OH, O—(C1-C6)-alkyl or NH2;
• phenyl, 1- or 2-naphthyl, biphenyl or a heterocyclic radical, where the rings or ring systems are in each case-substituted up to three 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—(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, or (C3-C8)-cycloalkyl, wherein the alkyl groups in each case one to seven hydrogen atoms may be replaced by fluorine;
• R6 is (CH2)0-6—R9, (CH2)0-6—COOH, (CH2)0-6—COO—(C1-C6)-alkyl, (CH2)0-6—CONH2, (CH2)06—CH(NHR15)-COR16, F, Cl, Br, CN, (C1-C18)-alkyl, (C3-C4)-cycloalkyl, or (C6-C8)-cycloalkyl, wherein the alkyl radicals or cycloalkyl radicals up to seven hydrogen atoms may be replaced by fluorine;
• R15 is H, or C(O)—(C1-C6)-alkyl;
• R16 is OH, O—(C1-C6)-alkyl, or NH2,
• R7 is (CH2)0-4—R12, H, (C1-C12)-alkyl, (C3-C4)-cycloalkyl, (C6-C8)-cycloalkyl, COO(C1-C6)-alkyl, or COO(C3-C8)-cycloalkyl, wherein the alkyl radicals or cycloalkyl radicals up to seven hydrogen atoms may be replaced by fluorine;
• R8 is (CH2)0-4—R14, (C1-C12)-alkyl, (C3-C4)-cycloalkyl, or (C6-C8)-cycloalkyl, wherein the alkyl or cycloalkyl radicals up to seven hydrogen atoms may be replaced by fluorine atoms;
• R9, R12, R14 independently of one another are phenyl, 1- or 2-naphthyl, biphenyl, or a heterocyclic radical, where the rings or ring systems are in each case substituted up to three 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—(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, or (C3-C8)-cycloalkyl, wherein the alkyl groups in each case one to seven hydrogen atoms may be replaced by fluorine;
• and their physiologically acceptable salts.