7-Phenylamino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments

A compound of the formula I

• in which the meanings are
• R1 is OH, O—(C1-C6)-alkyl or O—(C1-C6)-alkyl-OCO—(C1-C6)-alkyl;
• R2 is H, (C1-C6)-alkyl or phenyl;
• R3 is H, (C1-C8)-alkyl, (C3-C7)-cycloalkyl, pyridyl or phenyl, wherein (C1-C8)-alkyl and (C3-C7)-cycloalkyl may be substituted by R9 and wherein said phenyl and pyridyl may be substituted by R10;
• R9 is NH2, NH—(C1-C6)-alkyl, N—((C1-C6)-alkyl)2, COOH, COO—(C1-C6)-alkyl, (C3-C7)-cycloalkyl, heteroalkyl, heteroaryl, O-phenyl or phenyl, wherein said heteroaryl, O-phenyl and phenyl may be substituted by R11;
• R10 is F, Cl, Br, (C1-C6-alkyl), O—(C1-C6)-alkyl, COOH, COO—(C1-C6)-alkyl, NH2, NH—(C1-C6)-alkyl or N—((C1-C6)-alkyl)2;
• R11 is F, Cl, (C1-C6-alkyl), O—(C1-C6)-alkyl, NH2, NH—(C1-C6)-alkyl, N—((C1-C6)-alkyl)2, COOH or COO—(C1-C4)-alkyl;
• X is C—R4 or N;
• R4 is H, F, Cl, Br, OH, NO2, CN, (C1-C6)-alkyl or O—(C1-C6)-alkyl, wherein said (C1-C6)-alkyl and O—(C1-C6)-alkyl may be substituted more than once by F, Cl or Br;
• R5 is H, F, Cl, Br, OH, NO2, CN, (C1-C6)-alkyl or O—(C1-C6)-alkyl, where said (C1-C6)-alkyl and O—(C1-C6)-alkyl may be substituted more than once by F, Cl or Br;
• R6 is H, F, Cl, Br, NO2, CN or (C1-C6)-alkyl, wherein said (C1-C6)-alkyl may be substituted more than once by F, Cl or Br;
• R7 is H or (C1-C6)-alkyl;
• R8 is phenyl, wherein said phenyl may be substituted up to five times by F, Cl, Br, CN, NO2, (C1-C8)-alkyl, O—(C1-C8)-alkyl, S—(C1-C8)-alkyl, (C2-C8)-alkenyl, (C3-C7)-cycloalkyl, CO—(C1-C4)-alkyl, phenyl, benzyl, benzoyl, NH2, NH—(C1-C6)-alkyl, N—((C1-C6)-alkyl)2, P(O)—(O—(C1-C4)-alkyl)2 or heteroalkyl, wherein said (C1-C8)-alkyl, O—(C1-C8)-alkyl, S—(C1-C8)-alkyl, (C2-C8)-alkenyl, (C3-C7)-cycloalkyl, CO—(C1-C4)-alkyl, NH—(C1-C6)-alkyl, N—((C1-C6)-alkyl)2, P(O)—(O—(C1-C4)-alkyl)2 and heteroalkyl may be substituted more than once by F, Cl, Br, COOH, or COO—(C1-C4)-alkyl;
• heteroalkyl is heterocyclic, saturated or unsaturated 4- to 7-membered ring which may comprise up to 3 heteroatoms N, O or S as ring members, wherein said ring may be substituted by F, Cl, Br, CN, NO2, (C1-C4)-alkyl, OH, COOH or COO—(C1-C4)-alkyl;
• with the exception of compounds of the formula I in which the radicals simultaneously have the following meaning:
• X equal to N, R1 equal to OH, R2, R3, R4, R5 and R7 equal to H and R8 equal to unsubstituted phenyl;
• and the physiologically tolerated salts thereof.