US 10,189,788 B2Granted

Substituted N,2-diarylquinoline-4-carboxamides and the use thereof as anti-inflammatory agents

AssigneeBayer Pharma Aktiengesellschaft

InventorsHartmut Beck, Tobias Thaler, Raimund Kast, Daniel Meibom, Mark Meininghaus, Carsten Terjung, Martina Delbeck, Klemens Lustig, Uwe Muenster, Britta Olenik

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Abstract

The present application relates to novel substituted N,2-diarylquinoline-4-carboxamide derivatives, to processes for preparation thereof, to the use thereof alone or in combinations for treatment and/or prevention of diseases, and to the use thereof for production of medicaments for treatment and/or prevention of diseases, especially for treatment and/or prevention of fibrotic and/or inflammatory disorders.

A compound of the formula (I)

in which
RA is hydrogen, halogen, pentafluorosulfanyl, cyano, nitro, (C1-C4)-alkyl, hydroxyl, (C1-C4)-alkoxy, amino or a group of the formula —NH—C(═O)—R6, —NH—C(═O)—NH—R6 or —S(═O)n—R7, where (C1-C4)-alkyl and (C1-C4)-alkoxy may be up to trisubstituted by fluorine,
and in which
R6 is hydrogen or (C1-C4)-alkoxy which may be up to trisubstituted by fluorine,
R7 is (C1-C4)-alkyl which may be substituted by hydroxyl, methoxy or ethoxy or up to trisubstituted by fluorine,
and
n is the number 0, 1 or 2,
D is C-RD or N,
E is C-RE or N,
G is C-RG or N,
where not more than two of the ring members D, E and G at the same time are N,
and in which
RD and RE are each independently hydrogen, fluorine, chlorine, methyl, trifluoromethyl, methoxy or trifluoromethoxy,
and
RG is hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl,
Z is OH or a group of the formula —NH—R8, —NH—SO2—R9 or —NH—SO2—NR10AR10B, in which
R8 is hydrogen or (C1-C4)-alkoxy which may be up to trisubstituted by fluorine,
R9 is (C1-C4)-alkoxy which may be up to trisubstituted by fluorine, or phenyl,
and
R10A and R10B are each independently hydrogen or (C1-C4)-alkyl which may be up to trisubstituted by fluorine,
R1 is halogen, trifluoromethoxy, (trifluoromethyl)sulfanyl, pentafluorosulfanyl, (C1-C4)-alkyl, trimethylsilyl, cyclopropyl or cyclobutyl,
where (C1-C4)-alkyl may be up to trisubstituted by fluorine
and
cyclopropyl and cyclobutyl may be up to disubstituted by fluorine,
R2, R3 and R4 are each independently hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
R5 is (C1-C4)-alkyl which may be up to trisubstituted by fluorine, or is fluorine, chlorine, methoxy or cyclopropyl,
and
Ar is phenyl which may be mono- or disubstituted identically or differently by fluorine and chlorine, or is pyridyl or thienyl,
and the N-oxides, salts, solvates, salts of the N-oxides and solvates of the N-oxides and salts thereof.

26 more elements

Abstract

Claims11