C2-substituted indan-1-ols and their derivatives, processes for their preparation and their use as pharmaceuticals

A compound of the formula I,

• 8
• in which
• A)
• R1 to R4 are H;
• X is S, SO, or SO2;
• Y is (CH2)p, where p is 0, 1, 2 or 3;
• R5 is CF3, (C2-C18)-alkyl, (C3-C4)-cycloalkyl, or (C6-C8)-cycloalkyl, wherein the alkyl or cycloalkyl groups in each case have zero to seven hydrogen atoms replaced by fluorine;
• (CH2), —COR6, where r-is 1-6 and R6 is OH, O—(C1-C6)-alkyl or NH2;
• CH2—CH(NHR7)—COR8, where R7 is H, C(O)—(C1-C4)-alkyl or C(O)O—(C1-C4)-alkyl and R8 is OH, O—(C1-C6)-alkyl or NH2;
• phenyl, 1- or 2-naphthyl, biphenyl or a heterocyclic radical, where the rings or ring systems are unsubstituted or substituted one or two times by
• 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 the alkyl or cycloalkyl groups in each case have zero to seven hydrogen atoms independently replaced by fluorine, or
• F, Cl, Br, I, or CN;
• with the proviso that R5 is not unsubstituted phenyl, 4-fluorophenyl, 4-bromophenyl, 4-chlorophenyl, 3-methylphenyl, 4-methylphenyl, 4-methoxyphenyl, 4-n-butylphenyl, 4-t-butylphenyl, 2-aminophenyl, 2-nitrophenyl or C1-2-alkyl;
• or
• B)
• R1, R4 independently of one another are
• H, F, Cl, Br, I, CN, N3, NO2, OH, O(C1-C8)-alkyl, O(C3-C4 and C6-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, N H—(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, or (C2-C8)-alkynyl, where in the alkyl, cycloalkyl, alkenyl and alkynyl groups in each case have zero to seven hydrogen atoms replaced by fluorine, or one hydrogen replaced by OH, OC(O)CH3, O—CH2—Ph, NH2, NH—CO—CH3 or N(COOCH2Ph)2;
• or
• 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 in each case the aryl radical or heterocycle is unsubstituted or substituted one or 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 the alkyl groups in each case have zero to seven hydrogen atoms replaced by fluorine;
• R2, R3 independently of one another are
• H, F, Cl, Br, I, CN, N3, NO2, 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—(C5-C8)-alkyl, SO2—NH—(C3-CB)-cycloalkyl, NH—SO2—NH2, NH—SO2—(C1-C8)-alkyl, NH—SO2—(C5-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, or (C2-C8)-alkynyl, where in the alkyl, cycloalkyl, alkenyl and alkynyl groups in each case have zero to seven hydrogen atoms replaced by fluorine,
• or one hydrogen replaced by OH, OC(O)CH3, O—CH2—Ph, NH2, NH—CO—CH3 or N(COOCH2Ph)2;
• or
• 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 heterocycle is unsubstituted or substituted one or two times by F, Cl, Br, CN, OH, (C1-C4)-alkyl, CF3, O—(C1-C4)-alkyl,
• S(O)02(C1-C6)-alkyl, NH2, NH—SO2—(C1-C4)-alkyl,
• COOH, CO—O—(C1-C4)-alkyl, or CO—NH2 wherein the alkyl groups in each case have zero to seven hydrogen atoms replaced by fluorine;
• or R2 and R3 together form the group —O—CH2—O—;
• where in each case at least one of the radicals R1, R2, R3 and R4 is different from hydrogen;
• X is S, SO, or SO2;
• Y is (CH2)p, where p can be 0, 1, 2 or 3;
• R5 is (C1-C18)-alkyl, or (C3-C4— and C6-C8)-cycloalkyl, wherein the alkyl and cycloalkyl groups in each case have zero to seven hydrogen atoms replaced by fluorine;
• (CH2)r—COR6, where r is 1-6 and R6 is OH, O—(C1-C6)-alkyl or NH2;
• CH2—CH(NHR7)—COR8, where R7 is H, C(O)—(C1-C4)-alkyl or C(O)O—(C1-C4)-alkyl and R8 is OH, O—(C1-C6)-alkyl or NH2;
• phenyl, 1- or 2-naphthyl, biphenyl or a heterocyclic radical, where the rings or ring systems are unsubstituted or substituted one or two times by
• 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, N H—CO—(C2-C8)-alkyl, N H—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 or cycloalkyl groups in each case have zero to seven hydrogen atoms replaced by fluorine;
• or
• F, Cl, Br, I, or CN;
• or a physiologically tolerable salt thereof, in any stereoisomeric form, or a mixture of any such compounds in any ratio.