# US 2010/0168099 A1 · 1h-quinolin-4-one compounds, with affinity for the gaba receptor, processes, uses and compositions

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- Number: US 2010/0168099 A1
- Document ID: US20100168099A1
- Status: Published application
- Kind: A1
- Application number: 12/377,103
- Filed: 2007-08-09
- Published: 2010-07-01
- Earliest claimed: 2006-08-10
- Assignees: Ferrer Internacional, S.A.
- Inventors: José Luis Falcö; Albert Palomer; Antonio Guglietta
- Web page: https://patentgrep.com/patent/US20100168099A1

## CPC

- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- A61P 21/02: Muscle relaxants, e.g. for tetanus or cramps
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/08: Antiepileptics; Anticonvulsants
- A61P 25/20: Hypnotics; Sedatives
- A61P 25/22: Anxiolytics
- C07D 215/06: having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
- C07D 215/18: Halogen atoms or nitro radicals
- C07D 401/14: containing three or more hetero rings
- C07D 405/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 409/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 413/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 417/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## 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.

## Claims

### Claim at position 1

1-27. (canceled)

### Claim 28

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.

### Claim 29 (depends on 28)

The compound of claim 28 wherein R1 is selected from the group consisting of hydrogen, alkyl(C1-C6), Oalkyl(C1-C6), halogen and phenyl;
R2 is selected from the group consisting of hydrogen, allyl(C1-C6), halogen and phenyl.

### Claim 30 (depends on 28)

A compound according to claim 28, wherein R1 and R2 are independently selected from the group consisting of hydrogen, methyl, bromine and phenyl.

### Claim 31 (depends on 28)

A compound according to claim 28, wherein R3 and R4 are independently selected from the group consisting of hydrogen, phenyl, 4-fluorophenyl, 4-chlorophenyl, p-tolyl and 4-methoxyphenyl.

### Claim 32 (depends on 28)

A compound according to claim 28, wherein R5 is selected from the group consisting of NHNH2, N(methyl)NH2, 3-pyridyl, 4-pyridyl, 2-pyrazinyl, 5-methyl-2-furyl, 2-thienyl and 2,4-dimethyl-5-oxazolyl.

### Claim 33 (depends on 28)

A compound according to claim 28, wherein R6 and R7 are independently selected from the group consisting of hexyl, allyl, hydroxyethyl, cyclopropylmethyl, 1,3,4-thiadiazol-2-yl, 1,3-dimethyl-5-pyrazolyl, 1-methyl-3-pyrazolyl, 2,5-dimethyl-3-pyrrolinyl, 1,2,3,6-tetrahydropiperidinyl, 2,5-dimethyl-3-pyrazolyl, 2-acetyl-3-thienyl, 2-indanyl, 2-methyl-3-pyrazolyl, 2-methyl-5-indolyl, 2-pyrazinyl, 2-pyrimidinyl, 2-quinolyl, 2-thiazolyl, 3,5-isoxazol-4-yl, 3-isoxazolyl, 3-methyl-2-thienylmethyl, 3-methyl-5-isoxazolyl, 3-methyl-6-pyridyl, 3-methylisoxazol-5-yl, 3-oxazolyl, 3-pyrazolyl, 1,3,4-thiadiazol-2-yl, 4-methyl-2-thiazolyl, 5-trifluoromethyl-1,3,4-thiadiazol-2-yl, 5-cyclopropyl-3-pyrazolyl, 5-methyl-2-pyridyl, 5-methyl-3-pyrazolyl, 5-methyl-isoxazol-3-yl, 5-nitro-2-thiazol-2-yl, 6-methoxy-4-pyrimidinyl, 2-furylmethyl, 2-pyridylmethyl, 2-thienylethyl, phenyl, p-tolyl, 4-trifluoromethylphenyl, 4-dimethylaminophenyl, 4-fluorophenyl and 4-methoxyphenyl; or R6 and R7 form, together with the nitrogen atom to which they are attached, pyrrole, 2,5-dimethyl-3-pyrroline, piperidine, 1,2,3,6-tetrahydropyridine, 4-hydroxypiperidine, 3,5-dimethylpiperidine, morpholine, 2,6-dimethylmorpholine, 4-methylpiperazine and 4-acetylpiperazine.

### Claim 34

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.

### Claim 35 (depends on 28)

A process for preparing a compound of formula (I) as defined in claim 28, comprising reacting an intermediate compound of formula (VII):
wherein R1, R2, R3 and R4 are as defined for (I), with the appropriate 2-bromo ethanone (XII):

### Claim 36 (depends on 35)

A process according to claim 35 for preparing an amide compound of formula (I), wherein R5 is NR6R7, comprising reacting an acid compound of formula (I), wherein R5 is OH, with the appropriate amine R6R7NH (IX).

### Claim 37 (depends on 35)

A process according to claim 35 for preparing an hydrazide compound of formula (I), wherein R5 is N(R8)NH2, comprising reacting an ester compound of formula (I), wherein R5 is OR9, with the appropriate hydrazine of formula NH2NHR8 (X).

### Claim 38 (depends on 28)

Use of a compound according to claim 28 for the preparation of a medicament for treating or preventing diseases associated with the GABAA receptor modulation, anxiety, epilepsy, sleep disorders or insomnia, for inducing sedation-hypnosis, anaesthesia or muscle relaxation or for modulating the necessary time to induce sleep and its duration in a human or non-human mammal in need thereof.

### Claim 39 (depends on 28)

A pharmaceutical composition comprising a therapeutically effective amount of a compound as defined in claim 28, together with appropriate amounts of pharmaceutical excipients or carriers.

### Claim 40 (depends on 28, 34)

A method for treating or preventing diseases associated with the GABAA receptor modulation in a human or non-human mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of formula I as claimed in claim 28, or a 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;
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 COallyl(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; or a compound of claim 34; or a pharmaceutically acceptable salt thereof or a hydrate thereof.

### Claim 41 (depends on 40)

The method of claim 40, wherein the GABAA receptor is the α1-GABAA receptor.

### Claim 42 (depends on 40)

The method of claim 40 wherein the GABAA receptor is the α2-GABAA receptor.

### Claim 43 (depends on 40)

A method for treating or preventing anxiety in a human or non-human mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of claim 40, or a pharmaceutically acceptable salt or hydrate thereof.

### Claim 44 (depends on 40)

A method for treating or preventing epilepsy in a human or non-human mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of claim 40, or a pharmaceutically acceptable salt or hydrate thereof.

### Claim 45 (depends on 40)

A method for treating or preventing sleep disorders in a human or non-human mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of claim 40, or a pharmaceutically acceptable salt or hydrate thereof.

### Claim 46 (depends on 40)

A method for treating or preventing insomnia in a human or non-human mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of claim 40, or a pharmaceutically acceptable salt or hydrate thereof.

### Claim 47 (depends on 40)

A method for inducing sedation hypnosis in a human or non-human mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of claim 40, or a pharmaceutically acceptable salt or hydrate thereof.

### Claim 48 (depends on 40)

A method for inducing anesthesia in a human or non-human mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of claim 40, or a pharmaceutically acceptable salt or hydrate thereof.

### Claim 49 (depends on 40)

A method for modulating the necessary time to induce sleep and its duration in a human or non-human mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of claim 40, or a pharmaceutically acceptable salt or hydrate thereof.

### Claim 50 (depends on 40)

A method for inducing muscle relaxation in a human or non-human mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of claim 40, or a pharmaceutically acceptable salt or hydrate thereof.

### Claim 51 (depends on 34)

The use of 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;
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; or of a compound of claim 34;
or a pharmaceutically acceptable salt or hydrate thereof, or
for the preparation of a medicament for treating or preventing diseases associated with the GABAA receptor modulation, anxiety, epilepsy, sleep disorders or insomnia, for inducing sedation-hypnosis, anaesthesia or muscle relaxation or for modulating the necessary time to induce sleep and its duration in a human or non-human mammal in need thereof.

### Claim 52 (depends on 51)

A 1H-quinoline-one compound as defined in claim 51 for use in the treatment or prevention of diseases associated with the GABAA receptor modulation, anxiety, epilepsy, sleep disorders or insomnia, for inducing sedation-hypnosis, anaesthesia or muscle relaxation or for modulating the necessary time to induce sleep and its duration in a human or non-human mammal in need thereof.

### Claim 53 (depends on 52)

The 1H-quinoline-one compound of claim 52, wherein the GABAA receptor is the α1-GABAA receptor or the α2-GABAA receptor.