Derivatives of C2-substituted indan-1-ol compounds, methods for their preparation and use

A compound of the formula I,

• in which
• A) R1 to R4 are H;
• X is S, SO, or SO2;
• Y is (CH2)p, where p can be 0, 1, 2 or 3;
• R5 is CF3;
• (C1-C18)-alkyl;
• (C3-C4)-cycloalkyl, or (C6-C8)-cycloalkyl, where in the alkyl groups one to seven hydrogen atoms can be replaced by fluorine;
• (CH2)r—COR6, where r=1-6 and R6 can be OH, O—(C1-C6)-alkyl or NH2;
• CH2—CH(NHR7)—COR8, where R7 can be H or C(O)—(C1-C4)-alkyl and R8 can be OH, O—(C1-C6)-alkyl or NH2;
• phenyl, 1- or 2-naphthyl, biphenyl or a heterocyclic radical, where the rings or ring systems can be substituted up to 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, where in the alkyl groups in each case one to seven hydrogen atoms may be replaced by fluorine, F, Cl, Br, I, CN;
• R9 is (C1-C12)-alkyl, or (C3-C8)-cycloalkyl, where in the alkyl radicals one to seven hydrogen atoms may be replaced by fluorine;
• CO—O(C1-C6)-alkyl, CO—O(C3-C8)-cycloalkyl, C(O)—(C1-C8)-alkyl, C(O)—(C3-C8)-cycloalkyl, C(O)-phenyl, C(O)—CH(NHR12)-(C1-C8)-alkyl, phenyl, 1- or 2-naphthyl, biphenyl, 2-, 3- or 4-pyridyl, where the aryl or heteroaryl radicals 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, —CH2—COOH, O—CH2—CO—O(C1-C8)-alkyl, COOH, CO—O—(C1-C4)-alkyl, CO—NH2;
• (CH2)—R10;
• (CH2)s—R11, where s=2 or 3;
• R10 is (C1-C12)-alkyl, or (C3-C8)-cycloalkyl, where in the alkyl radicals one to seven hydrogen atoms may be replaced by fluorine;
• COOH, CONH2, CO—O(C1-C6)-alkyl, CO—O(C3-C8)-cycloalkyl;
• phenyl, 1- or 2-naphthyl, biphenyl, 2-, 3- or 4-pyridyl, 2- or 3-furyl or 2- or 3-thienyl, where the aryl or heteroaryl radicals 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, O—CH2—COOH, O—CH2—CO—O(C1-C8)-alkyl, COOH, CO—O—(C1-C4)-alkyl, CO—NH2;
• R11 is (C1-C12)-alkyl, or (C3-C8)-cycloalkyl, where in the alkyl radicals one to seven hydrogen atoms may be replaced by fluorine;
• COOH, CONH2, CO—O(C1-C6)-alkyl, CO—O(C3-C8)-cycloalkyl;
• phenyl, 1- or 2-naphthyl, biphenyl, 2-, 3- or 4-pyridyl, 2- or 3-furyl, 2- or 3-thienyl or 1-imidazolyl, where the aryl or heteroaryl radicals 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, O—CH2—COOH, O—CH2—CO—O(C1-C8)-alkyl, COOH, CO—O—(C1-C4)-alkyl, CO—NH2;
• R12 is H, or C(O)—(C1-C6)-alkyl;
• except for the compounds where simultaneously
• R1, R2, R3, R4=H, X═S, Y= a bond, R5=CH3, R9=CH3 or
• R1, R2, R3, R4=H, X═SO, Y= a bond, R5=4-chlorophenyl, R9=acetyl;
• 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, 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, where in 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;
• 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 in the alkyl groups one to seven hydrogen atoms may be 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-C8)-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, 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;
• 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 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 in the alkyl groups one to seven hydrogen atoms may be 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, where in the alkyl groups one to seven hydrogen atoms may be replaced by fluorine;
• (CH2)r—COR6, where r=1-6 and R6 can be OH, O—(C1-C6)-alkyl or NH2;
• CH2—CH(NHR7)—COR8, where R7 can be H or C(O)—(C1-C6)-alkyl and R8 can be OH, O—(C1-C6)-alkyl or NH2;
• phenyl, 1- or 2-naphthyl, biphenyl or a heterocyclic radical, where the rings or ring systems can be substituted up to 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, (C3-C8)-cycloalkyl, where in the alkyl groups in each case one to seven hydrogen atoms may be replaced by fluorine;
• F, Cl, Br, I, CN;
• R9 is (C1-C12)-alkyl, or (C3-C8)-cycloalkyl, where in the alkyl radicals one to seven hydrogen atoms may be replaced by fluorine;
• CO—O(C1-C6)-alkyl, CO—O(C3-C8)-cycloalkyl, C(O)—(C1-C8)-alkyl, C(O)—(C3-C8)-cycloalkyl, C(O)-phenyl, C(O)—CH(NHR12)—(C1-C8)-alkyl, phenyl, 1- or 2-naphthyl, biphenyl, 2-, 3- or 4-pyridyl, where the aryl or heteroaryl radicals 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, —CH2—COOH, O—CH2—CO—O(C1-C8)-alkyl, COOH, CO—O—(C1-C4)-alkyl, CO—NH2;
• (CH2)—R10;
• (CH2)s—R11, where s=2 or 3;
• R10 is (C1-C12)-alkyl, or (C3-C8)-cycloalkyl, where in the alkyl radicals one to seven hydrogen atoms may be replaced by fluorine;
• COOH, CONH2, CO—O(C1-C6)-alkyl, CO—O(C3-C8)-cycloalkyl;
• phenyl, 1- or 2-naphthyl, biphenyl, 2-, 3- or 4-pyridyl, 2- or 3-furyl or 2- or 3-thienyl, where the aryl or heteroaryl radicals 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, O—CH2—COOH, O—CH2—CO—O(C1-C8)-alkyl, COOH, CO—O—(C1-C4)-alkyl, CO—NH2;
• R11 is (C1-C12)-alkyl, or (C3-C8)-cycloalkyl, where in the alkyl radicals one to seven hydrogen atoms may be replaced by fluorine;
• COOH, CONH2, CO—O(C1-C6)-alkyl, CO—O(C3-C8)-cycloalkyl;
• phenyl, 1- or 2-naphthyl, biphenyl, 2-, 3- or 4-pyridyl, 2- or 3-furyl, 2- or 3-thienyl or 1-imidazolyl, where the aryl or heteroaryl radicals 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, O—CH2—COOH, O—CH2—CO—O(C1-C8)-alkyl, COOH, CO—O—(C1-C4)-alkyl, CO—NH2;
• R12 is H, or C(O)—(C1-C6)-alkyl;
• and their physiologically acceptable salts.