US 2011/0212941 A1Published application

Imidazoisoindole Neuropeptide S Receptor Antagonists

AssigneeMerch Sharp & Dohme Corp.

InventorsPeter J. Manley, Kausik K. Nanda, B. Wesley Trotter

Life of this patent

Estimating the term…

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.

Claims19

Dependent claims

A compound of the formula I:

wherein:
A is phenyl or pyridyl;
R1 is hydrogen or C1-6alkyl;
R2 is hydrogen or C1-6alkyl;
R3a, R3b and R3c are independently selected from the group consisting of:
(1) hydrogen,
(2) halogen,
(3) hydroxyl,
(4) —(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 R13,
(5) —(C═O)m—On—C3-6cycloalkyl, where the cycloalkyl is unsubstituted or substituted with one or more substituents selected from R13,
(6) —(C═O)m—C2-4alkenyl, where the alkenyl is unsubstituted or substituted with one or more substituents selected from R13,
(7) —(C═O)m—C2-4alkynyl, where the alkynyl is unsubstituted or substituted with one or more substituents selected from R13,
(8) —(C═O)m—On-phenyl or —(C═O)m—On-napthyl, where the phenyl or naphthyl is unsubstituted or substituted with one or more substituents selected from R13,
(9) —(C═O)m—On-heterocycle, where the heterocycle is unsubstituted or substituted with one or more substituents selected from R13,
(10) —(C═O)m—NR10R11, wherein R10 and R11 are independently selected from the group consisting of:
(a) hydrogen,
(b) C1-6alkyl, which is unsubstituted or substituted with R13,
(c) C3-6alkenyl, which is unsubstituted or substituted with R13,
(d) C3-6alkynyl, which is unsubstituted or substituted with R13,
(e) C3-6cycloalkyl which is unsubstituted or substituted with R13,
(f) phenyl, which is unsubstituted or substituted with R13, and
(g) heterocycle, which is unsubstituted or substituted with R13,
(11) —S(O)2—NR10R11,
(12) —S(O)q—R12, where q is 0, 1 or 2 and where R12 is selected from the definitions of R10 and R11,
(13) —CO2H,
(14) —CN, and
(15) —NO2;
R4 is —C1-6alkyl, which is unsubstituted or substituted with one or more substituents selected from R5,
wherein R5 is selected from the group consisting of:
(1) halogen,
(2) hydroxyl,
(3) —(C═O)m—On—C1-6alkyl, where the alkyl is unsubstituted or substituted with one or more substituents selected from R13,
(4) —(C═O)m—On—C3-6cycloalkyl, where the cycloalkyl is unsubstituted or substituted with one or more substituents selected from R13,
(5) —(C═O)m—C2-4alkenyl, where the alkenyl is unsubstituted or substituted with one or more substituents selected from R13,
(6) —(C═O)m—C2-4alkynyl, where the alkynyl is unsubstituted or substituted with one or more substituents selected from R13,
(7) —(C═O)m—On-phenyl or —(C═O)m—On-napthyl, where the phenyl or naphthyl is unsubstituted or substituted with one or more substituents selected from R13,
(8) —(C═O)m—On-heterocycle, where the heterocycle is unsubstituted or substituted with one or more substituents selected from R13,
(9) —(C═O)m—NR10R11,
(10) —S(O)2—NR10R11,
(11) —S(O)q—R12, and
(12) —CO2H;
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—On—C3-6cycloalkyl, 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 alkynyl 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 naphthyl 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, where R15 and R16 are independently selected from hydrogen and —C1-6alkyl, which is unsubstituted or substituted with phenyl,
(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—C1-6alkyl,
(8) phenyl,
(9) heterocycle,
(10) —CO2H, and
(11) —CN;
or a pharmaceutically acceptable salt thereof.

67 more elements

A compound which is selected from the group consisting of:

4-(5-benzyl-5H-imidazo[2,1-a]isoindol-5-yl)benzonitrile;
5-benzyl-5-(4-pyridin-3-ylphenyl)-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-(4-bromophenyl)-2-methyl-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-2-methyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-3-methyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-6-methoxy-5-(tetrahydro-2H-pyran-4-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-(4-pyridin-3-ylphenyl)-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-(4-pyridin-4-ylphenyl)-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-[4-(1-methyl-1H-pyrazol-4-yl)phenyl]-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-[4-(1,3-thiazol-5-yl)phenyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(3-methoxybenzyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(4-methoxybenzyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(2-methoxybenzyl)-5H-imidazo[2,1-a]isoindole;
4-(5-benzyl-5H-imidazo[2,1-a]isoindol-5-yl)benzonitrile;
3-{[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}benzonitrile;
4-{[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}benzonitrile;
3-{[5-(4-cyanophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}benzonitrile;
4-(5-benzyl-5H-imidazo[2,1-a]isoindol-5-yl)benzonitrile;
4-(5-benzyl-5H-imidazo[2,1-a]isoindol-5-yl)benzonitrile;
2-{[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}benzonitrile;
5-(4-bromophenyl)-5-(pyridin-2-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(pyridin-3-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-(4-methylphenyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(pyridin-4-ylmethyl)-5H-imidazo[2,1-a]isoindole;
4-[5-(pyridin-3-ylmethyl)-5H-imidazo[2,1-a]isoindol-5-yl]benzonitrile;
5-(4-bromophenyl)-5-(cyclohexylmethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(cyclobutylmethyl)-5H-imidazo[2,1-a]isoindole;
4-[5-(cyclohexylmethyl)-5H-imidazo[2,1-a]isoindol-5-yl]benzonitrile;
5-(4-bromophenyl)-5-(cyclopentylmethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(2-methylpropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(2-cyclohexylethyl)-5H-imidazo[2,1-a]isoindole;
4-[5-(cyclopentylmethyl)-5H-imidazo[2,1-a]isoindol-5-yl]benzonitrile;
4-[5-(2-cyclohexylethyl)-5H-imidazo[2,1-a]isoindol-5-yl]benzonitrile;
4-[5-(2-methylpropyl)-5H-imidazo[2,1-a]isoindol-5-yl]benzonitrile;
5-(4-bromophenyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-5H-imidazo[2,1-a]isoindole;
4-[5-(tetrahydro-2H-pyran-4-ylmethyl)-5H-imidazo[2,1-a]isoindol-5-yl]benzonitrile;
4-[5-(cyclopentylmethyl)-5H-imidazo[2,1-a]isoindol-5-yl]benzonitrile;
4-[5-(cyclopentylmethyl)-5H-imidazo[2,1-a]isoindol-5-yl]benzonitrile;
4-(5-cyclohexyl-5H-imidazo[2,1-a]isoindol-5-yl)benzonitrile;
5-(4-bromophenyl)-5-cyclohexyl-5H-imidazo[2,1-a]isoindole;
5-(3-bromophenyl)-5-(cyclopentylmethyl)-5H-imidazo[2,1-a]isoindole;
3-[5-(cyclopentylmethyl)-5H-imidazo[2,1-a]isoindol-5-yl]benzonitrile;
5-benzyl-5-(3-bromophenyl)-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-(6-bromopyridin-3-yl)-5H-imidazo[2,1-a]isoindole;
5-(6-bromopyridin-3-yl)-5-(cyclopentylmethyl)-5H-imidazo[2,1-a]isoindole;
3-(5-benzyl-5H-imidazo[2,1-a]isoindol-5-yl)benzonitrile;
5-(5-benzyl-5H-imidazo[2,1-a]isoindol-5-yl)pyridine-2-carbonitrile;
5-[5-(cyclopentylmethyl)-5H-imidazo[2,1-a]isoindol-5-yl]pyridine-2-carbonitrile;
5-(3-bromophenyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(tetrahydrofuran-3-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-(5-bromopyridin-2-yl)-5H-imidazo[2,1-a]isoindole;
5-(5-bromopyridin-2-yl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(2-oxo-2-piperidin-1-ylethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(2-morpholin-4-yl-2-oxoethyl)-5H-imidazo[2,1-a]isoindole;
tert-butyl-4-{[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}piperidine-1-carboxylate;
5-(4-bromophenyl)-5-(piperidin-4-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(3-cyclohexylpropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-7-methoxy-5-(tetrahydro-2H-pyran-4-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindole;
5-(4-fluorophenyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-(4-fluorophenyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-(tetrahydro-2H-pyran-4-yl)ethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-fluorophenyl)-5-[2-(tetrahydro-2H-pyran-4-yl)ethyl]-5H-imidazo[2,1-a]isoindole;
ethyl 4-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]butanoate;
5-(4-bromophenyl)-5-prop-2-en-1-yl-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-7-methoxy-5-(tetrahydro-2H-pyran-4-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-7-methoxy-5-(tetrahydro-2H-pyran-4-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-phenyl-5H-imidazo[2,1-a]isoindole;
5-benzyl-5-(4-methoxyphenyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorobenzyl)-5-phenyl-5H-imidazo[2,1-a]isoindole;
5-benzyl-7-methoxy-5-phenyl-5H-imidazo[2,1-a]isoindole;
5-(4-chlorobenzyl)-5-(4-chlorophenyl)-7-methoxy-5H-imidazo[2,1-a]isoindole;
5-(4-chlorobenzyl)-5-(4-chlorophenyl)-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-(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;
3-[5-(4-chlorophenyl)-6-methoxy-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-diethylpropanamide;
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-a]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;
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;
3-[5-(4-chlorophenyl)-7-methoxy-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-diethylpropanamide;
3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]-N,N-diethylpropanamide;
1-{[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}piperidin-2-one;
tert-butyl {[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}carbamate;
N-{[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}cyclohexanecarboxamide;
N-{[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}benzamide;
1-{[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}piperidin-2-one;
tert-butyl {2-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]ethyl}carbamate;
1-{[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}pyrrolidin-2-one;
1-{2-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]ethyl}piperidin-2-one;
1-{[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}azepan-2-one;
N-{2-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]ethyl}cyclohexanecarboxamide;
N-{2-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]ethyl}cyclopentanecarboxamide;
N-{2-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]ethyl}-2-methylpropanamide;
1-{4-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]butyl}pyrrolidin-2-one;
1-{4-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]butyl}piperidin-2-one;
2-[4-(5-benzyl-5H-imidazo[2,1-a]isoindol-5-yl)phenyl]propan-2-ol;
2-[4-(5-benzyl-5H-imidazo[2,1-a]isoindol-5-yl)phenyl]propan-2-ol;
5-(4-chlorophenyl)-5-(3-{4-[1-(3,3-difluoropyrrolidin-1-yl)ethyl]piperidin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
2-(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)propan-2-ol;
5-(4-chlorophenyl)-5-(3-{4-[1-(3,3-difluoropyrrolidin-1-yl)ethyl]piperidin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
2-(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)propan-2-ol;
5-(4-bromophenyl)-5-(3-{4-[(3,3-difluoropyrrolidin-1-yl)methyl]piperidin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(3-{4-[(3,3-difluoropyrrolidin-1-yl)methyl]piperidin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
1-[(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methyl]-4-fluoropyrrolidin-3-ol
5-(4-chlorophenyl)-5-(3-{4-[(2-methylpyrrolidin-1-yl)methyl]piperidin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-(3-{4-[(2,5-dimethylpyrrolidin-1-yl)methyl]piperidin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-(3-oxo-3-{4-[(2-propylpyrrolidin-1-yl)methyl]piperidin-1-yl}propyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(4-{[2-(methoxymethyl)pyrrolidin-1-yl]methyl}piperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
1-[(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methyl]pyrrolidin-3-ol
5-(4-chlorophenyl)-5-(3-{4-[(3,3-difluoropyrrolidin-1-yl)methyl]piperidin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-oxo-3-(4-{[3-(trifluoromethyl)pyrrolidin-1-yl]methyl}piperidin-1-yl)propyl]-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(4-{[(3S,4S)-3,4-difluoropyrrolidin-1-yl]methyl}piperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(4-{[(3S)-3-fluoropyrrolidin-1-yl]methyl}piperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(4-{[(3R)-3-fluoropyrrolidin-1-yl]methyl}piperidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole;
5-{3-[4-(azetidin-1-ylmethyl)piperidin-1-yl]-3-oxopropyl}-5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-(3-{4-[(3,3-difluoroazetidin-1-yl)methyl]piperidin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-{3-oxo-3-[4-(piperidin-1-ylmethyl)piperidin-1-yl]propyl}-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-(3-{4-[(4-fluoropiperidin-1-yl)methyl]piperidin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-(3-{4-[(4,4-difluoropiperidin-1-yl)methyl]piperidin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-(3-{4-[(3,3-difluoropiperidin-1-yl)methyl]piperidin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
1-[(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methyl]piperidin-3-ol;
1-[(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methyl]piperidin-4-ol;
N-[(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methyl]-N-ethylethanamine;
N-[(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methyl]-N-propylpropan-1-amine;
5-(4-chlorophenyl)-5-(3-{4-[(3,5-dimethylpiperidin-1-yl)methyl]piperidin-1-yl}-3-oxopropyl)-5H-imidazo[2,1-a]isoindole;
N-[(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methyl]-N-(1-methylethyl)propan-2-amine;
N-[(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methyl]-N-methylethanamine;
N-[(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methyl]-N-methylpropan-1-amine;
N-[(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methyl]-N-ethyl-2-methoxyethanamine;
N-[(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methyl]-2-methoxy-N-(2-ethoxyethyl)ethanamine;
N-[(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methyl]propan-1-amine;
N-[(1-{3-[5-(4-chlorophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propanoyl}piperidin-4-yl)methyl]-2,2,2-trifluoroethanamine;
5-(cyclohexylmethyl)-5-[4-(methylthio)phenyl]-5H-imidazo[2,1-a]isoindole;
5-(cyclohexylmethyl)-5-[4-(methylsulfonyl)phenyl]-5H-imidazo[2,1-a]isoindole;
5-(cyclohexylmethyl)-5-[4-(methylsulfanyl)phenyl]-5H-imidazo[2,1-a]isoindole;
5-(cyclohexylmethyl)-5-[4-(methylsulfonyl)phenyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-(5-methyl-1,3-oxazol-2-yl)ethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-[2-(5-methyl-1,3-oxazol-2-yl)ethyl]-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(1,4-dioxan-2-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-bromophenyl)-5-(1,4-dioxan-2-ylmethyl)-5H-imidazo[2,1-a]isoindole;
5-(4-cyanophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole-6-carbonitrile;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole-6-carbonitrile;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindol-7-ol;
5-(4-cyanophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole-6-carbonitrile;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole-6-carbonitrile;
5-(4-cyanophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole-7-carbonitrile;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole-7-carbonitrile;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindole-8-carbonitrile;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-7-methyl-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-7-methyl-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-8-methyl-5H-imidazo[2,1-a]isoindole;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-7-propoxy-5H-imidazo[2,1-a]isoindole;
2-({5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindol-7-yl}oxy)-N,N-dimethylethanamine;
5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-7-propoxy-5H-imidazo[2,1-a]isoindole;
2-({5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindol-7-yl}oxy)-N,N-dimethylethanamine;
or a pharmaceutically acceptable salt thereof.

355 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/127,985Filed 3 Nov 2009
Priority: 13 Nov 2008
Published: 1 Sep 2011
Term ends: Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents
A61P 25/20
Drugs for disorders of the nervous system: hypnotics; Sedatives

Family

Application61/199,181Us provisional application · filed 13 Nov 2008
US 8,541,595 B2Related patent
US 2011/0212941 A1This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound of the formula I:

wherein:
A is phenyl or pyridyl;
R1 is hydrogen or C1-6alkyl;
R2 is hydrogen or C1-6alkyl;
R3a, R3b and R3c are independently selected from the group consisting of:
(1) hydrogen,
(2) halogen,
(3) hydroxyl,
(4) —(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 R13,
(5) —(C═O)m—On—C3-6cycloalkyl, where the cycloalkyl is unsubstituted or substituted with one or more substituents selected from R13,
(6) —(C═O)m—C2-4alkenyl, where the alkenyl is unsubstituted or substituted with one or more substituents selected from R13,
(7) —(C═O)m—C2-4alkynyl, where the alkynyl is unsubstituted or substituted with one or more substituents selected from R13,
(8) —(C═O)m—On-phenyl or —(C═O)m—On-napthyl, where the phenyl or naphthyl is unsubstituted or substituted with one or more substituents selected from R13,
(9) —(C═O)m—On-heterocycle, where the heterocycle is unsubstituted or substituted with one or more substituents selected from R13,
(10) —(C═O)m—NR10R11, wherein R10 and R11 are independently selected from the group consisting of:
(a) hydrogen,
(b) C1-6alkyl, which is unsubstituted or substituted with R13,
(c) C3-6alkenyl, which is unsubstituted or substituted with R13,
(d) C3-6alkynyl, which is unsubstituted or substituted with R13,
(e) C3-6cycloalkyl which is unsubstituted or substituted with R13,
(f) phenyl, which is unsubstituted or substituted with R13, and
(g) heterocycle, which is unsubstituted or substituted with R13,
(11) —S(O)2—NR10R11,
(12) —S(O)q—R12, where q is 0, 1 or 2 and where R12 is selected from the definitions of R10 and R11,
(13) —CO2H,
(14) —CN, and
(15) —NO2;
R4 is —C1-6alkyl, which is unsubstituted or substituted with one or more substituents selected from R5,
wherein R5 is selected from the group consisting of:
(1) halogen,
(2) hydroxyl,
(3) —(C═O)m—On—C1-6alkyl, where the alkyl is unsubstituted or substituted with one or more substituents selected from R13,
(4) —(C═O)m—On—C3-6cycloalkyl, where the cycloalkyl is unsubstituted or substituted with one or more substituents selected from R13,
(5) —(C═O)m—C2-4alkenyl, where the alkenyl is unsubstituted or substituted with one or more substituents selected from R13,
(6) —(C═O)m—C2-4alkynyl, where the alkynyl is unsubstituted or substituted with one or more substituents selected from R13,
(7) —(C═O)m—On-phenyl or —(C═O)m—On-napthyl, where the phenyl or naphthyl is unsubstituted or substituted with one or more substituents selected from R13,
(8) —(C═O)m—On-heterocycle, where the heterocycle is unsubstituted or substituted with one or more substituents selected from R13,
(9) —(C═O)m—NR10R11,
(10) —S(O)2—NR10R11,
(11) —S(O)q—R12, and
(12) —CO2H;
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—On—C3-6cycloalkyl, 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 alkynyl 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 naphthyl 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, where R15 and R16 are independently selected from hydrogen and —C1-6alkyl, which is unsubstituted or substituted with phenyl,
(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—C1-6alkyl,
(8) phenyl,
(9) heterocycle,
(10) —CO2H, and
(11) —CN;
or a pharmaceutically acceptable salt thereof.

67 more elements

Facts

Application

13/127,985Filed 3 Nov 2009

Priority

13 Nov 2008

Published

1 Sep 2011

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents
A61P 25/20
Drugs for disorders of the nervous system: hypnotics; Sedatives