US 11,939,314 B2
Quinolin-2-one derivatives
Dieter Dorsch, Ober-Ramstadt (DE); Mathilde Muzerelle, Martigny (CH); Lars Burgdorf, Frankfurt am Main (DE); Margarita Wucherer-Plietker, Messel (DE); Paul Czodrowski, Mainz (DE); Christina Esdar, Darmstadt (DE); and Christos Tsaklakidis, Weinheim (DE)
Assigned to MERCK PATENT GMBH, Darmstadt (DE)
Filed by MERCK PATENT GMBH, Darmstadt (DE)
Filed on Oct. 12, 2021, as Appl. No. 17/499,278.
Application 16/795,972 is a division of application No. 16/069,326, granted, now 10,669,251, issued on Jun. 2, 2020, previously published as PCT/EP2016/002118, filed on Dec. 16, 2016.
Application 17/499,278 is a continuation of application No. 16/795,972, filed on Feb. 20, 2020, granted, now 11,186,562.
Claims priority of application No. 16150717 (EP), filed on Jan. 11, 2016.
Prior Publication US 2023/0028687 A1, Jan. 26, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/04 (2006.01); A61K 31/4375 (2006.01); A61K 31/4709 (2006.01); A61K 31/496 (2006.01); A61K 31/5377 (2006.01); A61K 31/551 (2006.01); A61K 45/06 (2006.01); C07D 401/14 (2006.01); C07D 403/04 (2006.01); C07D 403/14 (2006.01); C07D 407/14 (2006.01); C07D 413/14 (2006.01); C07D 417/14 (2006.01); C07D 471/04 (2006.01); C07D 487/04 (2006.01); C07D 487/10 (2006.01); C07D 491/107 (2006.01); C07D 497/10 (2006.01); C07D 498/10 (2006.01)
CPC C07D 401/04 (2013.01) [A61K 31/4375 (2013.01); A61K 31/4709 (2013.01); A61K 31/496 (2013.01); A61K 31/5377 (2013.01); A61K 31/551 (2013.01); A61K 45/06 (2013.01); C07D 401/14 (2013.01); C07D 403/04 (2013.01); C07D 403/14 (2013.01); C07D 407/14 (2013.01); C07D 413/14 (2013.01); C07D 417/14 (2013.01); C07D 471/04 (2013.01); C07D 487/04 (2013.01); C07D 487/10 (2013.01); C07D 491/107 (2013.01); C07D 497/10 (2013.01); C07D 498/10 (2013.01)] 7 Claims
 
1. Compounds of the formula I

OG Complex Work Unit Chemistry
in which
X1, X2, X3, X4 each, independently of one another, denote CH or N,
Y denotes N or CH,
Q denotes H or CH3,
R1 denotes H, F, Cl, Br, CN, CH3, CF3 or OCH3,
R2 denotes H, F or Cl,
R3 denotes phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, indolyl, indazolyl, thiophenyl, dihydroisoindolyl or benzimidazolyl, each of which is unsubstituted or mono-, di- or trisubstituted by Hal, CN, NO2, A, (CR4)nOR4, (CR4)nN(R4)2, (CR4)nS(O)mR4, (CR4)nCON(R4)2, (CR4)nCOHet, (CR4)nSO2N(R4)2, (CR4)nSO2Het, (CR4)nN(R4)2, (CR4)nHet, O(CR4)nCOHet, (CR4)nO(CR4)nHet, (CR4)nN(R4)(CR4)nHet, (CR4)nCON(R4)(CR4)nHet, (CR4)nCON(R4)(CR4)nN(R4)2, (CR4)nN(R4)COA, (CR4)nN(R4)COHet′, (CR4)nOCyc and/or (CR4)nCOOR4,
R4denotes H or A′,
A denotes unbranched or branched alkyl with 1-10 C-atoms, wherein two adjacent carbon atoms may form a double bond and/or one or two non-adjacent CH- and/or CH2- groups may be replaced by N-, O- and/or S-atoms and wherein 1-7 H-atoms may be replaced by R5, or cyclic alkyl having 3-7 C atoms,
A′ denotes unbranched or branched alkyl with 1-6 C-atoms, wherein one or two non-adjacent CH- and/or CH2-groups may be replaced by O-atoms,
Cyc denotes cyclobutyl, cyclopentyl or cyclohexyl, each of which is unsubstituted or mono- or disubstituted by A, Hal, OR4, N(R4)2, Het′, (CR4)nO(CR4)nHet′, CON(R4)2 and/or ═O,
R5 denotes F, Cl or OH,
Het denotes pyrrolidinyl, morpholinyl, piperidinyl, piperazinyl, [1,4]-diazepanyl, oxazolidinyl, hexahydro-pyrrolo[3,4-c]pyrrolyl, 2-oxa-6-aza-spiro[3.4]octanyl, 2-oxa-6-aza-spiro[3.5]nonanyl, 2-oxa-7-aza-spiro[3.5]nonanyl, 2,5-dioxa-8-aza-spiro[3.5]nonanyl, oxetanyl, 2-oxa-5-aza-spiro[3.4]octanyl, 2-oxa-6-aza-spiro[3.3]heptanyl, 3-aza-bicyclo[3.1.0]hexanyl, 2-oxa-7-aza-spiro[3.5]nonanyl, isoxazolidinyl, azetidinyl, 2,6-diaza-spiro[3.4]octanyl, hexahydro-pyrrolo[3,4-b]pyrrolyl, tetrahydrofuranyl or isothiazolidinyl, each of which is unsubstituted or mono-, di- or trisubstituted by A, Hal, OR4, OCOA, COA, (CR4)nN(R4)2, (CR4)nHet′, (CR4)nO(CR4)nHet′, CON(R4)2, COHet′, (CR4)nS(O)mR4, and/or ═O,
Het′ denotes pyrrolidinyl, morpholinyl, piperidinyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyridyl, pyrazolyl or piperazinyl, each of which is unsubstituted or mono- or disubstituted by A, Hal, OR4, N(R4)2 and/or ═O,
Hal denotes F, Cl, Br or I,
n denotes 0, 1, 2 or 3,
m denotes 0, 1 or 2, with the proviso that no more than two of X1, X2, X3, X4, denote N, and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.