# US 8,541,595 B2 · Imidazoisoindole neuropeptide S receptor antagonists

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- Number: US 8,541,595 B2
- Document ID: US8541595B2
- Status: Granted
- Kind: B2
- Application number: 13/127,985
- Filed: 2009-11-03
- Published: 2011-09-01
- Granted: 2013-09-24
- Earliest claimed: 2008-11-13
- Assignees: Merch Sharp & Dohme Corp.
- Applicants: Peter J. Manley; Kausik K Nanda; B. Wesley Trotter
- Inventors: Peter J. Manley; Kausik K Nanda; B. Wesley Trotter
- Web page: https://patentgrep.com/patent/US8541595B2

## CPC

- C07D 487/04: Ortho-condensed systems
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 25/20: Hypnotics; Sedatives
- A61P 25/22: Anxiolytics
- A61P 25/24: Antidepressants
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention is directed to imidazoisoindole compounds which are antagonists of neuropeptide S receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which the neuropeptide S receptor is involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the neuropeptide S receptor is involved.

## Claims

### Claim 1

A compound of the formula:
wherein:
R1 is hydrogen or C1-6alkyl;
R2 is hydrogen or C1-6alkyl;
R3a is selected from the group consisting of:
(1) hydrogen,
(2) halogen,
(3) —CN, and
(4) C1-6alkyl;
R4 is selected from the group consisting of:
(1) —CH2CH2—(C═O)-heterocycle, where the heterocycle is unsubstituted or substituted with one or more substituents selected from R13, and
(2) —CH2CH2—(C═O)—NR15R16, where R15 and R16 are independently selected from hydrogen and —C1-6alkyl, which is unsubstituted or substituted with phenyl;
R13 is selected from the group consisting of:
(1) halogen,
(2) hydroxyl,
(3) —(C═O)m—On—C1-6alkyl, where m is 0 or 1, n is 0 or 1 (wherein if m is 0 or n is 0, a bond is present) and where the alkyl is unsubstituted or substituted with one or more substituents selected from R14,
(4) —On—(C1-3)perfluoroalkyl,
(5) —(C═O)m—OnC3-6cycloalkyl, where the cycloalkyl is unsubstituted or substituted with one or more substituents selected from R14,
(6) —(C═O)m—C2-4alkenyl, where the alkenyl is unsubstituted or substituted with one or more substituents selected from R14,
(7) —(C═O)m—C2-4alkynyl, where the alkenyl is unsubstituted or substituted with one or more substituents selected from R14,
(8) —(C═O)m—On-phenyl or —(C═O)m—On-napthyl, where the phenyl or is unsubstituted or substituted with one or more substituents selected from R14,
(9) —(C═O)m—On-heterocycle, where the heterocycle is unsubstituted or substituted with one or more substituents selected from R14,
(10) —(C═O)m—NR15R16,
(11) —S(O)2—NR15R16,
(12) —S(O)q—R17, where q is 0, 1 or 2 and where R17 is —C1-6alkyl, which is unsubstituted or substituted with phenyl;
(13) —CO2H
(14) —CN, and
(15) —NO2;
R14 is selected from the group consisting of:
(1) hydroxyl,
(2) halogen,
(3) C1-6alkyl,
(4) —C3-6cycloalkyl,
(5) —O—C1-6alkyl,
(6) —O(C═O)—C1-6alkyl,
(7) —NH—C1-6 alkyl,
(8) phenyl,
(9) heterocycle,
(10) —CO2H, and
(11) —CN;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1 wherein R1 is hydrogen and R2 is hydrogen.

### Claim 3

A compound which is selected from the group consisting of:
5-(4-bromophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-2-methyl-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-3-methyl-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-2-ethyl-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-3-ethyl-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-2-methyl-5-{3-oxo-3-[4-(1-pyrrolidin-1-ylethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-3-methyl-5-{3-oxo-3-[4-(1-pyrrolidin-1-ylethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindol-7-ol;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-2-(trifluoromethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-{3-oxo-3-[4-(1-pyrrolidin-1-ylethyl)piperidin-1-yl]propyl}-2-(trifluoromethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-6-methoxy-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-8-methoxy-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-9-methoxy-5H-imidazo[2,1-a]isoindole;
3-[5-(4-chlorophenyl)-6-methoxy-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-diethylpropanamide;
2-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-diethylacetamide;
5-(4-bromophenyl)-5-[2-(4,4-dimethylpiperidin-1-yl)-2-oxoethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{2-oxo-2-[4-(1H-pyrazol-4-yl)piperidin-1-yl]ethyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-oxo-2-(4-phenylpiperidin-1-yl)ethyl]-5H-imidazo[2,1-a]isoindole;
5-{2-[(1s,4s)-7-azabicyclo[2.2.1]hept-7-yl]-2-oxoethyl}-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-(hexahydrofuro[3,2-b]pyridin-4(2H)-yl)-2-oxoethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-(3,3-difluoropyrrolidin-1-yl)-2-oxoethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-(4,4-difluoropiperidin-1-yl)-2-oxoethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-(4-fluoropiperidin-1-yl)-2-oxoethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-oxo-2-(4-pyridin-4-ylpiperidin-1-yl)ethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-(2-ethylpiperidin-1-yl)-2-oxoethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-(3-methylpiperidin-1-yl)-2-oxoethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-(3,3-dimethylpiperidin-1-yl)-2-oxoethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]-5H-imidazo[2,1-a]isoindole;
5-[2-(2-benzylpyrrolidin-1-yl)-2-oxoethyl]-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole;
5-[2-(2-azaspiro[4.4]non-2-yl)-2-oxoethyl]-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-oxo-2-(2-phenylpyrrolidin-1-yl)ethyl]-5H-imidazo[2,1-a]isoindole;
2-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-(3-hydroxy-1,1-dimethylbutyl)acetamide;
2-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-pyridin-2-ylacetamide;
2-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-cyclohexyl-N-methylacetamide;
2-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-ethyl-N-(1-methylethyl)acetamide;
5-(4-bromophenyl)-5-[2-(octahydroquinolin-1(2H)-yl)-2-oxoethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-(3,5-dimethylpiperidin-1-yl)-2-oxoethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(2-oxo-2-pyrrolidin-1-ylethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(3-oxo-3-piperidin-1-ylpropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(3-oxo-3-pyrrolidin-1-ylpropyl)-5H-imidazo[2,1-a]isoindole;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-cyclopropylpropanamide;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-diethylpropanamide;
5-(4-bromophenyl)-5-[3-(3,3-dimethylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-oxo-3-[4-(1H-pyrazol-4-yl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-oxo-3-(4-phenylpiperidin-1-yl)propyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-oxo-3-(4-pyridin-4-ylpiperidin-1-yl)propyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(2-ethylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-oxo-3-(2-propylpiperidin-1-yl)propyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(3-methylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(3,5-dimethylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-cyclohexyl-N-(1-methylethyl)propanamide;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-cyclohexyl-N-methylpropanamide;
5-(3-azepan-1-yl-3-oxopropyl)-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-bis(1-methylethyl)propanamide;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-bis(2-methylpropyl)propanamide;
5-(4-bromophenyl)-5-[3-(4,4-dimethylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
1-{3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidine-3-carboxamide;
5-[3-(1,4′-bipiperidin-1′-yl)-3-oxopropyl]-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-oxo-3-(4-pyrrolidin-1-ylpiperidin-1-yl)propyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-oxo-3-[3-(trifluoromethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(octahydro-2H-pyrido[1,2-a]pyrazin-2-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-[4-(1-morpholin-4-ylethyl)piperidin-1-yl]-3-oxopropyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-oxo-3-[2-(trifluoromethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-oxo-3-[4-(1-pyrrolidin-1-ylethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-ethyl-N-(tetrahydrofuran-2-ylmethyl)propanamide;
5-(4-bromophenyl)-5-[3-oxo-3-(3-phenylpiperidin-1-yl)propyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-oxo-3-[4-(trifluoromethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
(1-{3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)(pyridin-3-yl)methanol;
5-(4-bromophenyl)-5-{3-[3-(morpholin-4-ylmethyl)piperidin-1-yl]-3-oxopropyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-[4-(morpholin-4-ylmethyl)piperidin-1-yl]-3-oxopropyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(3-methoxypiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(1,4-dioxa-7-azaspiro[4.5]dec-7-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(3-fluoropiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
6-(1-{3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)pyridin-2(1H)-one;
5-(4-bromophenyl)-5-[3-(4-cyclopropylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(2,6-dimethylmorpholin-4-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-oxo-3-(2-phenylmorpholin-4-yl)propyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-oxo-3-(2-pyridin-3-ylmorpholin-4-yl)propyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(3,3-difluoropiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-yl]-3-oxopropyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(3-morpholin-4-yl-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(4,4-difluoropiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(2-methylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-[2-(methoxymethyl)pyrrolidin-1-yl]-3-oxopropyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-oxo-3-[3-(trifluoromethyl)pyrrolidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(3-methylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(3,3-difluoropyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-oxo-3-(2-phenylpyrrolidin-1-yl)propyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-oxo-3-(3-phenylpyrrolidin-1-yl)propyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(4-fluoropiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(4,4-dimethyl-1,3-oxazolidin-3-yl)-3-oxopropyl]-5H-imidazo[2,1-]isoindole;
5-(4-bromophenyl)-5-[3-(2-methylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[3-(2,6-dimethylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-[3-(2-azabicyclo[2.2.1]hept-2-yl)-3-oxopropyl]-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-tert-butyl-N-methylpropanamide;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-tert-butyl-N-ethylpropanamide;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-tert-butyl-N-(2-methoxyethyl)propanamide;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-(dicyclopropylmethyl)propanamide;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-dimethylpropanamide;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-dipropylpropanamide;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-bis(2-methoxyethyl)propanamide;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-bis(1-methylpropyl)propanamide;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-ethyl-N-(1-methylethyl)propanamide;
5-{3-[(1s,4s)-7-azabicyclo[2.2.1]hept-7-yl]-3-oxopropyl}-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole;
5-[3-(8-azabicyclo[3.2.1]oct-8-yl)-3-oxopropyl]-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole;
3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-diethylpropanamide;
5-(4-chlorophenyl)-5-[3-(3,3-dimethylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2-ethylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-{3-oxo-3-[4-(thiophen-2-ylcarbonyl)piperazin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(3-methylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(3,5-dimethylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(3-azepan-1-yl-3-oxopropyl)-5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindole;
3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-bis(1-methylethyl)propanamide;
1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidine-3-carboxamide;
5-(4-chlorophenyl)-5-{3-oxo-3-[3-(trifluoromethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-{3-oxo-3-[2-(trifluoromethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-{3-oxo-3-[4-(1-pyrrolidin-1-ylethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2-methylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-{3-[2-(methoxymethyl)pyrrolidin-1-yl]-3-oxopropyl}-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-(3-oxo-3-piperidin-1-ylpropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(3,4-dihydro-1,5-naphthyridin-1(2H)-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-methyl-N-pyridin-4-ylpropanamide;
3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-methyl-N-pyridin-2-ylpropanamide;
5-(4-chlorophenyl)-5-[3-(4,4-dimethyl-1,3-oxazolidin-3-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2-methylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2,6-dimethylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-[3-(2-azabicyclo[2.2.1]hept-2-yl)-3-oxopropyl]-5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindole;
N-tert-butyl-3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-methylpropanamide;
N-tert-butyl-3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-ethylpropanamide;
N-tert-butyl-3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-(2-methoxyethyl)-propanamide;
3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-dimethylpropanamide;
3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-dipropylpropanamide;
3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-bis(2-methoxyethyl)propanamide;
3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-bis(1-methylpropyl)propanamide;
3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-ethyl-N-(1-methylethyl)propanamide;
5-(3-azetidin-1-yl-3-oxopropyl)-5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindole;
5-{3-[(1s,4s)-7-azabicyclo[2.2.1]hept-7-yl]-3-oxopropyl}-5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindole;
5-[3-(8-azabicyclo[3.2.1]oct-8-yl)-3-oxopropyl]-5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-7-methoxy-5H-imidazo[2,1-a]isoindole;
5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindole;
N,N-diethyl-3-[5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanamide;
5-[3-(3,3-dimethylpiperidin-1-yl)-3-oxopropyl]-5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindole;
5-[3-(2-ethylpiperidin-1-yl)-3-oxopropyl]-5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindole;
5-(4-fluorophenyl)-5-{3-oxo-3-[4-(thiophen-2-ylcarbonyl)piperazin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-fluorophenyl)-5-[3-(3-methylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-[3-(3,5-dimethylpiperidin-1-yl)-3-oxopropyl]-5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindole;
5-(3-azepan-1-yl-3-oxopropyl)-5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindole;
3-[5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-bis(1-methylethyl)propanamide;
1-{3-[5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidine-3-carboxamide;
5-(4-fluorophenyl)-5-{3-oxo-3-[3-(trifluoromethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-fluorophenyl)-5-{3-oxo-3-[2-(trifluoromethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-fluorophenyl)-5-{3-oxo-3-[4-(1-pyrrolidin-1-ylethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-fluorophenyl)-5-[3-(2-methylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-fluorophenyl)-5-{3-[2-(methoxymethyl)pyrrolidin-1-yl]-3-oxopropyl}-5H-imidazo[2,1-a]isoindole;
5-(4-fluorophenyl)-5-(3-oxo-3-piperidin-1-ylpropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-fluorophenyl)-5-[3-(2-methylpiperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-[3-(2,6-dimethylpiperidin-1-yl)-3-oxopropyl]-5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindole;
5-[3-(2-azabicyclo[2.2.1]hept-2-yl)-3-oxopropyl]-5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindole;
N-tert-butyl-3-[5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-methylpropanamide;
N-tert-butyl-N-ethyl-3-[5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanamide;
N-tert-butyl-3-[5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-(2-methoxyethyl)propanamide;
3-[5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-dipropylpropanamide;
3-[5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-bis(1-methylpropyl)propanamide;
N-ethyl-3-[5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-(1-methylethyl)propanamide;
5-{3-[(1s,4s)-7-azabicyclo[2.2.1]hept-7-yl]-3-oxopropyl}-5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindole;
5-[3-(8-azabicyclo[3.2.1]oct-8-yl)-3-oxopropyl]-5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindole;
4-{5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindol-5-yl}benzonitrile;
5-(4-bromophenyl)-5-{3-oxo-3-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-7-methoxy-5-{3-oxo-3-[4-(1-pyrrolidin-1-ylethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[4-(2,5-dimethylpyrrolidin-1-yl)-4-oxobutyl]-5H-imidazo[2,1-a]isoindole;
4-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-bis(1-methylethyl)butanamide;
4-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-ethyl-N-methylbutanamide;
5-(4-bromophenyl)-5-(4-oxo-4-piperidin-1-ylbutyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{4-oxo-4-[4-(1-pyrrolidin-1-ylethyl)piperidin-1-yl]butyl}-5H-imidazo[2,1-a]isoindole;
(1-{3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methanol;
5-(4-bromophenyl)-5-{3-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]-3-oxopropyl}-5H-imidazo[2,1-a]isoindole;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-methyl-N-(1-methylcyclopentyl)-propanamide;
5-(4-bromophenyl)-5-[3-oxo-3-(2-propylpyrrolidin-1-yl)propyl]-5H-imidazo[2,1-a]isoindole;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-methyl-N-(1-methylpiperidin-4-yl)propanamide;
N-benzyl-3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-ethylpropanamide;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-(2,4-dimethylcyclopentyl)-N-methylpropanamide;
(1-{3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)(pyridin-2-yl)methanol;
1′-{3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}-3H-spiro[2-benzofuran-1,4′-piperidin]-3-one;
5-(4-bromophenyl)-5-{3-[4-(5-methyl-1,3,4-oxadiazol-2-yl)piperidin-1-yl]-3-oxopropyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(3-{3-[(2-methyl-1H-imidazol-1-yl)methyl]piperidin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-[4-(3-methyl-1H-pyrazol-5-yl)piperidin-1-yl]-3-oxopropyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-oxo-3-[4-(1H-pyrazol-1-ylmethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-[4-(cyclopentylmethyl)piperazin-1-yl]-3-oxopropyl}-5H-imidazo[2,1-a]isoindole;
2-(4-{3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperazin-1-yl)cyclohexanol;
5-{3-[4-(1-azabicyclo[2.2.2]oct-3-yl)piperazin-1-yl]-3-oxopropyl}-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-{3-oxo-3-[4-(2-pyrrolidin-1-ylethyl)piperazin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(3-{4-[(2-methyl-1,3-thiazol-4-yl)methyl]piperazin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
5-[3-(4-benzylpiperazin-1-yl)-3-oxopropyl]-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole;
3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N-ethyl-N-(2-methoxyethyl)propanamide;
3-[5-(4-chlorophenyl)-7-methoxy-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-diethylpropanamide; and
3-[5-(4-chlorophenyl)-7-methoxy-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-dipropylpropanamide;
or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

A pharmaceutical composition which comprises an inert carrier and a compound of claim 1 or a pharmaceutically acceptable salt thereof.