1h-quinolin-4-one compounds, with affinity for the gaba receptor, processes, uses and compositions
AssigneeFerrer Internacional, S.A.
InventorsJosé Luis Falcö, Albert Palomer, Antonio Guglietta
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Abstract
The invention provides new 1H-quinolin-4-one compounds of formula (I), wherein R1, R2, R3, R4 and R5 have different meanings, and pharmaceutically acceptable salts and hydrates thereof. Compounds of formula (I) are useful for treating or preventing diseases associated with GABAA receptors modulation, anxiety, epilepsy, sleep disorders including insomnia, and for inducing sedation-hypnosis, anesthesia, sleep and muscle relaxation. The invention also provides synthetic procedures for preparing said compounds.
Claims27
1-27. (canceled)
A 1H-quinolin-one compound of formula (I):
- wherein
- R1 and R2 are independently selected from the group consisting of hydrogen, alkyl(C1-C6), Oalkyl(C1-C6), halogen and phenyl;
- R3 and R4 are independently selected from the group consisting of hydrogen and phenyl optionally substituted by alkyl(C1-C6), halogen and Oalkyl(C1-C6);
- R5 is selected from the group consisting of R5 is selected from the group consisting of NR6R7, N(R8)NH2 and a heteroaryl ring selected from the group consisting of pyridyl, furyl, thienyl, oxazolyl, isoxazolyl, imidazolyl, pyrrolyl, pyrazolyl, pyrimidinyl and pyrazinyl, wherein each heteroaryl ring contains one or two optional alkyl(C1-C6) substituents;
- R6 and R7 are independently selected from the group consisting of hydrogen;
- alkyl(C1-C6);
- alkenyl(C2-C6);
- cyclo alkyl (C3-C6)alkyl(C1-C6);
- hydroxyalkyl (C1-C6);
- hetero aryl selected from the group consisting of pyridyl, pyrimidinyl, pyrazinyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isoxazolyl, benzisoxazolyl, pyrazolyl, furyl, benzofuryl, thienyl, benzothienyl, thiadiazolyl, pyrrolyl, imidazolyl, benzimidazolyl, indolyl, quinolyl and isoquinolyl, wherein each heteroaryl contains one or two optional substituents independently selected from the group consisting of alkyl(C1-C6), Oalkyl(C1-C6), haloalkyl(C1-C6), cycloalkyl(C3-C6), NO2 and COalkyl(C1-C6);
- thienylalkyl(C1-C6), furylalkyl(C1-C6), pyridylalkyl (C1-C6);
- and aryl selected from the group consisting of phenyl and indanyl, wherein each aryl contains one or two optional substituents selected from the group consisting of alkyl(C1-C6), haloalkyl(C1-C6), halogen, Ndialkyl(C1-C6), NHalkyl(C1-C6), Oalkyl(C1-C6), NO2, CN, OH, NH2, COOH, COalkyl(C1-C6), COOalkyl(C1-C6), CONHalkyl(C1-C6), CONdialkyl(C1-C6) and COphenyl;
- with the proviso that NR6R7 is not NH2, NH(C1-C4 alkyl) or N(C1-C4 alkyl)2;
- or R6 and R7 can form, together with the nitrogen atom to which they are attached, a heterocycle selected from pyrrolidine, 3-pyrroline, 1,2,3,6-tetrahydropyridine, piperidine, morpholine, thiomorpholine and piperazine, wherein each heterocycle contains one, two, three or four optional substituents selected from the group consisting of OH, alkyl(C1-C6) and COalkyl(C1-C6);
- R8 is selected from the group consisting of hydrogen and alkyl(C1-C6);
- and
- R9 is alkyl(C1-C6);
- with the proviso that R3 and R4 cannot be hydrogen simultaneously;
- and pharmaceutically acceptable salts and hydrates thereof.
A compound selected from the group consisting of
- 5-Methyl-1-(2-morpholin-4-yl-2-oxo-ethyl)-2-phenyl-1H-quinolin-4-one;
- N,N-Diethyl-2-(7-methyl-4-oxo-2-phenyl-4H-quinolin-1-yl)-acetamide;
- 7-Methyl-1-(2-morpholin-4-yl-2-oxo-ethyl)-2-phenyl-1 FI-quinolin-4-one;
- (7-Methyl-4-oxo-2-phenyl-4H-quinolin-1-yl)-acetic acid ethyl ester;
- N,N-Dibutyl-2-(7-methyl-4-oxo-2-phenyl-4H-quinolin-1-yl)-acetamide;
- N,N-Diisopropyl-2-(5-methyl-4-oxo-2-phenyl-4H-quinolin-1-yl)-acetamide;
- 5-Methyl-1-(2-oxo-2-pyrrolidin-1-yl-ethyl)-2-phenyl-1H-quinolin-4-one;
- 2-(7-Methyl-4-oxo-2-phenyl-4H-quinolin-1-yl)-N,N-dipropyl-acetamide;
- N,N-Dihexyl-2-(5-methyl-4-oxo-2-phenyl-4H-quinolin-1-yl)-acetamide;
- 5-Methyl-1-(2-oxo-2-piperidin-1-yl-ethyl)-2-phenyl-1H-quinolin-4-one;
- 5-Methyl-1-(2-oxo-2-pyrrolidin-1-yl-ethyl)-2-phenyl-1H-quinolin-4-one;
- 7-Methyl-1-(2-oxo-2-pyrrolidin-1-yl-ethyl)-2-phenyl-1H-quinolin-4-one;
- N,N-Dibutyl-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N,N-dipropyl-acetamide;
- 7-Methyl-1-(2-oxo-2-piperidin-1-yl-ethyl)-3-phenyl-1H-quinolin-4-one;
- N,N-Dihexyl-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- N,N-Diethyl-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- 7-Methyl-1-(2-oxo-2-pyrrolidin-1-yl-ethyl)-3-phenyl-1H-quinolin-4-one,
- 7-Methyl-1-(2-morpholin-4-yl-2-oxo-ethyl)-3-phenyl-1H-quinolin-4-one,
- N,N-Diisopropyl-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- N,N-Dihexyl-2-(5-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- 5-Methyl-1-(2-oxo-2-piperidin-1-yl-ethyl)-3-phenyl-1H-quinolin-4-one;
- 5-Methyl-1-(2-morpholin-4-yl-2-oxo-ethyl)-3-phenyl-1H-quinolin-4-one;
- N,N-Diethyl-2-(5-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- N,N-Dibutyl-2-(5-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- 7-Methyl-1-(2-oxo-2-pyridin-3-yl-ethyl)-3-phenyl-1H-quinolin-4-one;
- 7-Methyl-1-(2-oxo-2-thiophen-2-yl-ethyl)-3-phenyl-1H-quinolin-4-one;
- 7-Methyl-1-(2-oxo-2-pyridin-2-yl-ethyl)-3-phenyl-1H-quinolin-4-one;
- 7-Methyl-1-(2-oxo-2-pyridin-4-yl-ethyl)-3-phenyl-1H-quinolin-4-one;
- 1-[2-(4-Acetyl-piperazin-1-yl)-2-oxo-ethyl]-7-methyl-3-phenyl-1H-quinolin-4-one;
- 7-Methyl-1-[2-(5-methyl-furan-2-yl)-2-oxo-ethyl]-3-phenyl-1H-quinolin-4-one;
- 1-[2-(2,6-Dimethyl-morpholin-4-yl)-2-oxo-ethyl]-7-methyl-3-phenyl-1H-quinolin-4-one;
- 1-[2-(2,4-Dimethyl-oxazol-5-yl)-2-oxo-ethyl]-7-methyl-3-phenyl-1H-quinolin-4-one;
- 7-Methyl-1-(2-oxo-2-pyrazin-2-yl-ethyl)-3-phenyl-1H-quinolin-4-one;
- 7-Methyl-1-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-3-phenyl-1H-quinolin-4-one;
- 2-[3-(4-Methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N,N-dipropyl-acetamide;
- 2-[3-(4-Chloro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N,N-dipropyl-acetamide;
- 2-(7-Methyl-4-oxo-3-p-tolyl-4H-quinolin-1-yl)-N,N-dipropyl-acetamide;
- N-Cyclopropylmethyl-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-propyl-acetamide;
- 1-[2-(3,5-Dimethyl-piperidin-1-yl)-2-oxo-ethyl]-7-methyl-3-phenyl-1H-quinolin-4-one;
- 1-[2-(3,6-Dihydro-2H-pyridin-1-yl)-2-oxo-ethyl]-7-methyl-3-phenyl-1H-quinolin-4-one;
- 1-[2-(2,5-Dimethyl-2,5-dihydro-pyrrol-1-yl)-2-oxo-ethyl]-7-methyl-3-phenyl-1H-quinolin-4-one;
- N,N-Diallyl-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- 2-(7-Bromo-4-oxo-3-phenyl-4H-quinolin-1-yl)-N,N-dipropyl-acetamide;
- 2-(5-Bromo-4-oxo-3-phenyl-4H-quinolin-1-yl)-N,N-dipropyl-acetamide;
- 2-(4-Oxo-3,7-diphenyl-4H-quinolin-1-yl)-N,N-dipropyl-acetamide;
- 2-(4-Oxo-3-phenyl-4H-quinolin-1-yl)-N,N-dipropyl-acetamide;
- 2-(4-Oxo-3,5-diphenyl-4H-quinolin-1-yl)-N,N-dipropyl-acetamide;
- (7-Methyl-4-oxo-3-p-tolyl-4H-quinolin-1-yl)-acetic acid methyl ester;
- (7-Methyl-4-oxo-3-p-tolyl-4H-quinolin-1-yl)-acetic acid;
- [3-(4-Chloro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-acetic acid methyl ester;
- [3-(4-Fluoro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetic acid methyl ester;
- [3-(4-Fluoro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetic acid;
- 2-[3-(4-Chloro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-phenyl-acetamide;
- 2-[3-(4-Chloro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-pyrazin-2-yl-acetamide;
- [3-(4-Chloro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetic acid;
- [3-(4-Chloro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetic acid hydrazide;
- 2-(7-Methyl-4-oxo-3-p-tolyl-4H-quinolin-1-yl)-N-phenyl-acetamide;
- 2-[3-(4-Fluoro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-phenyl-acetamide;
- 2-(7-Methyl-4-oxo-3-p-tolyl-4H-quinolin-1-yl)-N-thiazol-2-yl-acetamide;
- N-(5-Methyl-isoxazol-3-yl)-2-(7-methyl-4-oxo-3-p-tolyl-4H-quinolin-1-yl)-acetamide;
- [3-(4-Fluoro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetic acid hydrazide;
- (7-Methyl-4-oxo-3-p-tolyl-4H-quinolin-1-yl)-acetic acid hydrazide;
- 2-[3-(4-Chloro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-(5-methyl-isoxazol-3-yl)-acetamide;
- 2-[3-(4-Fluoro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-(5-methyl-isoxazol-3-yl)-acetamide;
- N-Ethyl-N-(2-hydroxy-ethyl)-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide,
- N-(2-Hydroxy-ethyl)-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-propyl-acetamide;
- N,N-Diallyl-2-(5-methyl-4-oxo-3-pentyl-4H-quinolin-1-yl)-acetamide;
- N-(2-Hydroxy-ethyl)-2-(5-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-propyl-acetamide;
- (7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetic acid;
- (5-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetic acid;
- [3-(4-Chloro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetic acid N-methyl-hydrazide;
- (7-Methyl-4-oxo-3-p-tolyl-4H-quinolin-1-yl)-acetic acid N-methyl-hydrazide;
- [3-(4-Fluoro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetic acid N-methyl-hydrazide;
- 2-[3-(4-Fluoro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-thiazol-2-yl-acetamide;
- 2-[3-(4-Chloro-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-thiazol-2-yl-acetamide;
- 2-[3-(4-Methoxy-phenyl)-7-methyl-4-oxo-yl]-N-(4-trifluoromethyl-phenyl)-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-(4-trifluoromethyl-phenyl)-acetamide;
- N-(4-Methoxy-phenyl)-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- N-(4-Methoxy-phenyl)-2-[3-(4-methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetamide;
- 2-[3-(4-Methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-(5-methyl-2H-pyrazol-3-yl)-acetamide;
- 2-[7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl]-N-thiazol-2-yl-acetamide;
- 2-[3-(4-Methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-thiazol-2-yl-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-(3-methyl-thiophen-2-ylmethyl)-acetamide;
- 2-[3-(4-Methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-(3-methyl-isoxazol-5-yl)-acetamide;
- 2-[3-(4-Methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-(5-methyl-pyridin-2-yl)-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-pyrimidin-2-yl-acetamide;
- N-Furan-2-ylmethyl-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-[3-(4-methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetamide;
- N,N-Diethyl-2-[3-(4-methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetamide;
- 3-(4-Methoxy-phenyl)-7-methyl-1-(2-oxo-2-pyrrolidin-1-yl-ethyl)-1H-quinolin-4-one;
- 3-(4-Methoxy-phenyl)-7-methyl-1-(2-oxo-2-piperidin-1-yl-ethyl)-1H-quinolin-4-one;
- N-Ethyl-N-(2-hydroxy-ethyl)-2-[3-(4-methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]acetamide;
- N-(2-Hydroxy-ethyl)-2-[3-(4-methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-propyl-acetamide;
- N-Cyclopropylmethyl-2-[3-(4-methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-propyl-acetamide;
- N,N-Bis-(2-hydroxy-ethyl)-2-[3-(4-methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetamide;
- N,N-Diallyl-2-[3-(4-methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetamide;
- N-(3,5-Dimethyl-isoxazol-4-yl)-2-(7-methyl-4-oxo-phenyl-4H-quinolin-1-yl)-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-(1-methyl-1H-pyrazol-3-yl)-acetamide,
- N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-(5-methyl-pyridin-2-yl)-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-[1,3,4]thiadiazol-2-yl-acetamide;
- N-(4-Dimethylamino-phenyl)-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- N-(3-Methyl-isoxazol-5-yl)-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-p-tolyl-acetamide;
- 2-[3-(4-Methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-N-(1-methyl-1H-pyrazol-3-yl)-acetamide;
- 1-[2-(2,5-Dimethyl-2,5-dihydro-pyrrol-1-yl)-2-oxo-ethyl]-3-(4-methoxy-phenyl)-7-methyl-1H-quinolin-4-one;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-(5-methyl-2H-pyrazol-3-yl)-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-pyridin-2-ylmethyl-acetamide;
- N-(2-Acetyl-thiophen-3-yl)-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- N-Ethyl-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-[1,3,4]thiadiazol-2-yl-acetamide;
- N-(2-Methyl-1H-indol-5-yl)-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- 1-[2-(3,6-Dihydro-2H-pyridin-1-yl)-2-oxo-ethyl]-7-methyl-3-phenyl-1H-quinolin-4-one;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-(1H-pyrazol-3-yl)-acetamide,
- N-(4-Fluoro-phenyl)-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-quinolin-2-yl-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-(2-methyl-2H-pyrazol-3-yl)-acetamide;
- N-(5-Cyclopropyl-2H-pyrazol-3-yl)-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- N-Isoquinolin-3-yl-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- N-Indan-2-yl-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-(2-thiophen-2-yl-ethyl)-acetamide;
- 7-Bromo-1-[2-(3,6-dihydro-2H-pyridin-1-yl)-2-oxo-ethyl]-3-phenyl-1H-quinolin-4-one;
- (7-Bromo-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetic acid hydrazide;
- 2-(7-Bromo-4-oxo-3-phenyl-4H-quinolin-1-yl)-N,N-dibutyl-acetamide;
- 7-Bromo-1-(2-oxo-2-pyrrolidin-1-yl-ethyl)-3-phenyl-1H-quinolin-4-one;
- 7-Bromo-1-(2-oxo-2-piperidin-1-yl-ethyl)-3-phenyl-1H-quinolin-4-one;
- 7-Bromo-1-[2-(2,6-dimethyl-morpholin-4-yl)-2-oxo-ethyl]-3-phenyl-1H-quinolin-4-one;
- N,N-Diallyl-2-(7-bromo-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- 7-Bromo-1-[2-(2,5-dimethyl-2,5-dihydro-pyrrol-1-yl)-2-oxo-ethyl]-3-phenyl-1H-quinolin-4-one;
- 2-(7-Bromo-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-cyclopropylmethyl-N-propyl-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-(5-nitro-thiazol-2-yl)-acetamide;
- N-Isoxazol-3-yl-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- 2-(7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-N-(4-methyl-thiazol-2-yl)-acetamide;
- 7-Bromo-1-(2-oxo-2-piperidin-1-yl-ethyl)-3-phenyl-1H-quinolin-4-one;
- (7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetic acid methyl ester;
- (7-Methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetic acid;
- [3-(4-Methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetic acid methyl ester;
- [3-(4-Methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetic acid;
- (7-Bromo-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetic acid;
- 1-[2-(2,6-Dimethyl-morpholin-4-yl)-2-oxo-ethyl]-(4-methoxy-phenyl)-7-methyl-1H-quinolin-4-one;
- 1-[2-(3,5-Dimethyl-piperidin-1-yl)-2-oxo-ethyl]-3-(4-methoxy-phenyl)-7-methyl-1H-quinolin-4-one;
- N-(6-Methoxy-pyrimidin-4-yl)-2-(7-methyl-4-oxo-3-phenyl-4H-quinolin-1-yl)-acetamide;
- 1-[2-(4-Hydroxy-piperidin-1-yl)-2-oxo-ethyl]-7-methyl-3-phenyl-1H-quinolin-4-one;
- N-Isoxazol-3-yl-2-[3-(4-methoxy-phenyl)-7-methyl-4-oxo-4H-quinolin-1-yl]-acetamide;
- and
- 1-[2-(4-Hydroxy-piperidin-1-yl)-2-oxo-ethyl]-3-(4-methoxy-phenyl)-7-methyl-1H-quinolin-4-one;
- and
- the pharmaceutically acceptable salts and hydrates thereof.
Dependencies are inferred from the claim text.