US 7,402,674 B2
7-Phenylamino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments
Elisabeth Defossa, Idstein (Germany); Dieter Kadereit, Offenbach (Germany); Sven Ruf, Florsheim (Germany); Thomas Klabunde, Frankfurt (Germany); Dieter Schmoll, Frankfurt (Germany); Andreas Herling, Bad Camberg (Germany); and Karl-Ulrich Wendt, Frankfurt (Germany)
Assigned to Sanofi-Aventis Deutschland GmbH,, Frankfurt (Germany)
Filed on Jan. 25, 2005, as Appl. No. 11/42,023.
Claims priority of provisional application 60/582719, filed on Jun. 24, 2004.
Claims priority of application No. 10 2004 004 973 (DE), filed on Jan. 31, 2004; and application No. 10 2004 033 405 (DE), filed on Jul. 10, 2004.
Prior Publication US 2005/0182085 A1, Aug. 18, 2005
Int. Cl. C07D 471/02 (2006.01); C07D 215/38 (2006.01); A61K 31/44 (2006.01); A61K 31/47 (2006.01)
U.S. Cl. 546—156  [546/153; 546/123; 514/300; 514/312; 514/313] 5 Claims
 
1. A compound of the formula I

OG Complex Work Unit Drawing
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.