Ring-substituted diphenylazetidinones, process for their preparation, medicaments comprising these compounds, and their use

A compound of the formula I,

• wherein:
• R1, R2, R3, R4, R5, and R6, independently of one another, are chosen from:
• (C1-C30)-alkyl, wherein the (C1-C30)-alkyl is substituted by q LAG units,
• wherein at least one carbon atom of the alkyl radical is replaced by:
• aryl or heteroaryl radicals, which are unsubstituted or substituted one, two, or three times by R7, or by (C3-C10)-cycloalkyl or heterocycloalkyl radicals, which are unsubstituted or substituted one, two, three, or four times by R7, and
• wherein at least one carbon atom of the alkyl radical is optionally replaced by a radical chosen from:
• —S(O)m—(where m=0-2), —O—, —(C═O)—, —(C═S)—, —CH═CH—, —C≡C—, —N((C1-C6)-alkyl)-, —N(phenyl), —N((C1-C6)-alkyl-phenyl)-, —N(CO—(CH2)1-10—COOH)— and —NH—;
• or
• H, F, Cl, Br, I, CF3, NO2, N3, CN, COOH, COO(C1-C6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON[(C1-C6)-alkyl]2, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, or O—(C1-C6)-alkyl, wherein the alkyl radical is unsubstituted or at least one hydrogen in the alkyl radical is replaced by fluorine;
• or
• SO2—NH2, SO2NH(C1-C6)-alkyl, SO2N[(C1-C6)-alkyl]2, S—(C1-C6)-alkyl, S—(CH2)n-phenyl, SO—(C1-C6)-alkyl, SO—(CH2)n-phenyl, SO2-(C1-C6)-alkyl, or SO2—(CH2)n-phenyl;
• wherein n=0-6, and wherein the phenyl radical is unsubstituted or substituted one or two times, each substituent chosen independently from:
• F, Cl, Br, OH, CF3, NO2, CN, OCF3, O—(C1-C6)-alkyl, (C1-C6)-alkyl, and NH2;
• or
• NH2, NH—(C1-C6)-alkyl, N((C1-C6)-alkyl)2, NHCO(C1-C6)-alkyl, phenyl, or O—(CH2)n-phenyl, wherein n=0-6, and wherein the phenyl ring is unsubstituted or substituted one, two, or three times, each substituent chosen independently from:
• F, Cl, Br, I, OH, CF3, NO2, CN, OCF3, O—(C1-C6)-alkyl, (C1-C6)-alkyl, NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, SO2—CH3, COOH, COO—(C1-C6)-alkyl, and CONH2;
• R7 represents F, Cl, Br, I, CF3, NO2, N3, CN, COOH, COO(C1-C6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON[(C1-C6)-alkyl]2, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, or O—(C1-C6)-alkyl, wherein the alkyl radical is unsubstituted or at least one hydrogen in the alkyl radical may be replaced by fluorine;
• or
• PO3H2, SO3H, SO2—NH2, SO2NH(C1-C6)-alkyl, SO2N[(C1-C6)-alkyl]2, S—(C1-C6)-alkyl, S—(CH2)n-phenyl, SO—(C1-C6)-alkyl, SO—(CH2)n-phenyl, SO2—(C1-C6)-alkyl, or SO2—(CH2)n-phenyl, wherein n=0-6, and wherein the phenyl radical is unsubstituted or substituted one or two times, each substituent chosen independently from:
• F, Cl, Br, OH, CF3, NO2, CN, OCF3, O—(C1-C6)-alkyl, (C1-C6)-alkyl, and NH2;
• or
• C(NH)(NH2), NH2, NH—(C1-C6)-alkyl, N((C1-C6)-alkyl)2, NHCO(C1-C6)-alkyl, phenyl, or O—(CH2)n-phenyl, wherein n=0-6, and wherein the phenyl ring is unsubstituted or substituted one, two, or three times, each substituent chosen independently from:
• F, Cl, Br, I, OH, CF3, NO2, CN, OCF3, O—(C1-C6)-alkyl, (C1-C6)-alkyl, NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, SO2—CH3, COOH, COO—(C1-C6)-alkyl, and CONH2;
• (LAG) is an amino acid residue, or an oligopeptide residue comprising 2 to 9 amino acids;
• wherein q=1-5;
• and wherein at least one of the radicals R1 to R6 must have the meaning:
• (C1-C30)-alkyl, wherein the (C1-C30)-alkyl is substituted by q LAG units,
• wherein at least one carbon atom of the alkyl radical is replaced by:
• aryl or heteroaryl radicals, which are unsubstituted or substituted one, two, or three times by R7, or
• (C3-C10)-cycloalkyl or heterocycloalkyl radicals, which are unsubstituted or substituted one, two, three, or four times by R7, or
• —S(O)m—(where m=0-2), —O—, —(C═O)—, —(C═S)—, —CH═CH—, —C≡C—, —N((C1-C6)-alkyl)-, —N(phenyl)-, —N((C1-C6)-alkyl-phenyl)-, —N(CO—(CH2)1-10—COOH)— or —NH—;
• or a pharmaceutically acceptable salt thereof, in any stereoisomeric form, or a mixture of any such compounds in any ratio.