US 2006/0189629 A1Published application

N-substituted benzimidazolyl c-Kit inhibitors

AssigneeOSI Pharmaceuticals, Inc.

InventorsJoshua Bolger, Arlindo Castelhano, Andrew Crew, Han-Qing Dong, Ayako Honda, Radoslaw Laufer, An-Hu Li, Kristen Mulvihill, Li Qiu, Colin Sambrook Smith, Yingchaun Sun, Graham Wynne, Tao Zhang

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Abstract

Compounds represented by Formula (I): or a pharmaceutically acceptable salt or N-oxide thereof, are useful in the treatment of cancer.

Claims26

Dependent claims

A compound represented by Formula (I):

or a pharmaceutically acceptable salt or N-oxide thereof, wherein:
one of R11, R12, R13 and R14 is —NR3COR31, —NR3CONR3R31, —NR3SO2R31, —CO2R3, —CO2H, —C0-8alkylNR3R31 or —CONR3R31;
the others each independently F, Cl, C0-3alkyl, C0-8alkoxy, or —N(C0-8alkyl)(C0-8alkyl);
X is a cyclyl or heterocyclyl group, optionally substituted with 1-4 halogen, —NR32R33, —NR32COR33, —NR32CO2R33, —NR32SO2R33, —OR32, —SR32, —SO2R32, —SO2NR32R33, —CO2R32, —CO2H, —CONR32R33, —C0-8alkyl, —C2-8alkenyl, —C2-8alkynyl, —CN, CF3, OCF3, NO2, oxo, cyclyl or heterocyclyl substituents;
Y is absent or
wherein the point of attachment to X can be from either the left or the right as shown;
Ra and Rb are each independently C0-8alkyl or C3-8cycloalkyl;
or Ra and Rb taken together with the C to which they are attached form a saturated or partially unsaturated 3-10 membered ring optionally containing 0-4 N, O, S, SO, or SO2 at the ring nodes, provided that no N, O or S atoms are placed adjacent to each other at ring nodes;
Rc is C0-8alkyl;
or Rc, taken with either Ra or Rb, form a 3-7 membered saturated or partially unsaturated ring;
m is 0, 1, 2, 3, 4 or 5;
provided that when m is 0 or 1, no N, O or S atoms are adjacent to each other in the N—X—Y-Z linking bridge;
n is 1, 2, 3, 4 or 5;
provided that, when n is 1, no N, O or S atoms are adjacent to each other in the N—X—Y-Z linking bridge;
Z is a cyclyl or heterocycyl group, optionally substituted with 1-5 independent halogen, —NR34R35, —NR34COR35, —NR34C(O)OR35, —NR34SO2R35, —OR34, —SR34, —SO2R34, —SO2NR34R35, —C(O)OR34, —CO2H, —CONR34R35, C0-8alkyl, C2-8alkenyl, C2-8alkynyl, —OC0-8alkyl, —SC0-8alkyl, —SO2C0-8alkyl, —SO2N(C0-8alkyl)(C0-8alkyl), —C(O)OC0-8alkyl, CN, CF3, NO2, oxo, cyclyl or heterocyclyl substituents;
or, when Y is present, Z further can be C0-8alkyl-O—C0-8alkyl, C0-8alkyl-O—C(O)—C0-8alkyl, or C0-8alkyl-C(O)—O—C0-8alkyl;
provided that when Y is —OCH2—, Z must be substituted with 1-5-NR34R35, —NR34COR35, —NR34C(O)OR35, —NR34SO2R35, —OR34, —SR34, —SO2R34, —SO2NR34R35, —CO2R34, —CO2H, —CONR34R35, C0-8alkyl, C2-8alkenyl, C2-8alkynyl, CF3, NO2, oxo, cyclyl or heterocyclyl substituents;
provided that when Y is NHCH2, Z must be substituted with 1-5 halogen, —NR34R35, —NR34COR35, —NR34C(O)OR35, —NR34SO2R35, —OR34, —SR34, —SO2R34, —SO2NR34R35, —CO2R34, —CO2H, —CONR34R35, C0-8alkyl, C2-8alkenyl, C2-8alkynyl, CF3, NO2, oxo, cyclyl or heterocyclyl substituents;
provided that when Y is absent, X and Z cannot contain N;
R3, R31, R32, R33, R34 and R35 are independently C0-8alkyl substituted with heterocyclyl, or OH substituents;
CF3, CHF2, —C0-8alkyl-O—C0-8alkyl, —C0-8alkyl-N(C0-8alkyl)(C0-8alkyl), —C0-8alkyl-S(O)0-2—C0-8alkyl or —C0-8alkyl-S(O)2N(C0-8alkyl)(C0-8alkyl).

18 more elements

A compound consisting of

1-[3-(3-phenylpropoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[(4-cyanobenzyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
ethyl 5-[(3-{5-[(pyridin-3-ylmethylamino)carbonyl]-1H-benzimidazol-1-yl}phenoxy)methyl]-2-furoate;
3-(3-{5-[(pyridin-3-ylmethylamino)carbonyl]-1H-benzimidazol-1-yl}phenoxy)pentyl acetate;
1-[3-(2-naphthylmethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-(3-{[4-(trifluoromethyl)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
ethyl 4-{3-[5-(pyridin-3-ylmethylaminocarbonyl)-1H-benzimidazol-1-yl]phenoxy}hexanoate;
1-[3-(2-morpholin-4-ylethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[(4-fluorobenzyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
methyl 4-[(4-{5-[(pyridin-3-ylmethylamino)carbonyl]-1H-benzimidazol-1-yl}phenoxy)methyl]benzoate;
ethyl 5-[(4-{5-[(pyridin-3-ylmethylamino)carbonyl]-1H-benzimidazol-1-yl}phenoxy)methyl]-2-furoate;
1-{3-[(4-methylbenzyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[(4-nitrobenzyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[(4-methylbenzyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
methyl 4-[(3-{5-[(pyridin-3-ylmethylamino)carbonyl]-1H-benzimidazol-1-yl}phenoxy)methyl]benzoate;
1-{4-[(4-trifluoromethylbenzyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[4-(2-naphthylmethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[(4-nitrobenzyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[4-(cyclohexylmethyloxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[4-(1-phenethylethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[3-(1-phenethylethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[3-(2-phenylethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[4-(2-morpholin-4-ylethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
1-[4-(2-phenoxyethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[3-(2-phenoxyethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[3-(1H-indol-3-ylmethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[3-(4-fluorophenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[3-(4-fluorophenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(2-methoxyethoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[4-(2-methoxyethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[2-(2-methoxyethoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[(2-methylthiazol-4-ylmethyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[(quinolin-2-ylmethyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[2-(4-chlorophenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[4-(pyridin-3-ylmethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[3-(1,1′-biphenyl-2-ylmethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[(3,4-dimethoxybenzyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[3-(cyclobutylmethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[(4-methoxybenzyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[(2-methoxybenzyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[(4-benzyloxy-3-methoxybenzyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[(4-{t-butyl}benzyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[(4-phenylbutyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[3-(pyridin-4-ylmethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[3-(3-pyridin-4-ylpropoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[3-(pyridin-3-ylmethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[4-(pyridin-4-ylmethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[4-(3-pyridin-4-ylpropoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[4-(2-(4-methylthiazol-5-yl)ethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[3-(furan-3-ylmethyl)oxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-{4-[(2-thiophen-2-ylethyl)oxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-{3-[(2-thiophen-2-ylethyl)oxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-{4-[(2-thiophen-3-ylethyl)oxy]phenyl}-1H-benzimidazole-5-carboxamide;
1-(3-{[1-(4-chlorophenyl)cyclopropyl]methoxy}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-(4-{[1-(4-chlorophenyl)cyclopropyl]methoxy}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-{3-[(2-thiophen-3-ylethyl)oxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-(2-morpholin-4-ylethyl)-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(3-dimethylaminopropyl)-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(2-dimethylaminoethyl)-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(3-methoxypropyl)-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(2-methoxyethyl)-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(2-piperidin-1-ylethyl)-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
2-(4-{[1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazol-5-yl]carbonyl}piperazin-1-yl)ethanol;
N-[3-(4-methylpiperazin-1-yl)propyl]-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(3-morpholin-4-ylpropyl)-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-[(1-oxidopyridin-3-yl)methyl]-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
1-{4-[3-(2-oxopyridin-1 (2H)-yl)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-oxopyridin-1 (4H)-yl)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-(4-{2-[2-oxo-5-(trifluoromethyl)pyridin-1 (2H)-yl]ethoxy}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(5-chloro-2-oxopyridin-1 (2H)-yl)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
or a pharmaceutically acceptable salt, or N-oxide, thereof.

70 more elements

A compound consisting of

1-[3-(3-phenoxypropoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[4-(2-phenylethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[3-(2-methoxyethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[4-(2-ethoxyethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-[3-(2-ethoxyethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[2-(4-bromophenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-bromophenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-methylthiazol-4-ylmethyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[(quinolin-2-ylmethyl)oxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-(4-{3-[3-(trifluoromethoxy)phenoxy]propoxy}phenyl)-1H-benzimidazole-5-carboxamide;
1-{4-[3-(3-methoxyphenoxy}propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[3-(3-chlorophenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[3-(4-cyanophenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[3-(4-methoxyphenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[3-(3-methylphenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[3-(3-ethynylphenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[3-(4-methylphenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[3-(4-cyanophenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-(3-{3-[3-(trifluoromethoxy)phenoxy]propoxy}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[3-(3-chlorophenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[3-(4-chlorophenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[3-(4-bromophenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-(3-{3-[4-(trifluoromethoxy)phenoxy]propoxy}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[3-(3,4-dichlorophenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[3-(4-imidazol-1-ylphenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-(3-{3-[4-(4H-1,2,4-triazol-4-yl)phenoxy]propoxy}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-(3-{3-[4-(trifluoromethyl)phenoxy]propoxy}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
methyl 4-(3-{3-[5-(N-pyridin-3-ylmethyl)aminocarbonyl]-1H-benzimidazol-1-ylphenoxy}propoxy)benzoate;
1-{4-[3-(4-bromophenoxy)propoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[2-(4-methylphenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(3-chlorophenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(3-ethynylphenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(3-bromophenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-cyanophenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-chlorophenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-methoxyphenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(3-methylphenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-(4-{2-[(3-trifluoromethoxy)phenoxy]ethoxy}phenyl)-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-methylphenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(3-methoxyphenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[2-(3-chlorophenoxy)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-N-[3-(4-methylpiperazin-1-yl)propyl]-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-N-(2-morpholin-4-ylethyl)-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-N-[2-(N,N-dimethylamino)ethyl]-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-N-[3-(N,N-dimethylamino)propyl]-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-N-(3-methoxypropyl)-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-N-(2-methoxyethyl)-1H-benzimidazole-5-carboxamide;
2-{1-[(1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-1H-benzimidazol-5-yl)carbonyl]piperidin-4-yl}ethanol;
1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-N-(2-piperidin-1-ylethyl)-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-N-(3-morpholin-4-ylpropyl)-1H-benzimidazole-5-carboxamide;
1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-N-ethyl-1H-benzimidazole-5-carboxamide
2-{1-[(1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-1H-benzimidazol-5-yl)carbonyl]piperazin-4-yl}ethanol;
N-pyridin-3-ylmethyl-1-{4-[3-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-{3-[3-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
1-{4-[2-(2-oxopyridin-1 (2H)-yl)ethoxy]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-{4-[2-(pyridin-3-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-{3-[3-(pyridin-3-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-{4-[2-(5-chloropyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
5-(2-{4-[5-(pyridin-3-ylmethylaminocarbonyl)-1H-benzimidazol-1-yl]phenoxy}ethoxy)nicotinic acid;
or a pharmaceutically acceptable salt, or N-oxide, thereof.

59 more elements

A compound consisting of

N-[3-(dimethylamino)propyl]-1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
(4-{[1-([2-(4-fluorophenoxy)ethoxy]phenyl)-1H-benzimidazol-5-yl]carbonyl}piperazin-1-yl)ethanol;
N-ethyl-1-{4-[2-(4-fluorophenoxy)ethoxy]phenyl}-H-benzimidazole-5-carboxamide;
N-[3-(dimethylamino)propyl]-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
1-{4-[3-(4-fluorophenoxy)propoxy]phenyl}-N-(3-methoxypropyl)-1H-benzimidazole-5-carboxamide;
1-{4-[3-(4-fluorophenoxy)propoxy]phenyl}-N-(2-methoxyethyl)-1H-benzimidazole-5-carboxamide;
1-{4-[3-(4-fluorophenoxy)propoxy]phenyl}-N-(3-morpholin-4-ylpropyl)-1H-benzimidazole-5-carboxamide;
1-{4-[3-(4-fluorophenoxy)propoxy]phenyl}-N-(2-morpholin-4-ylethyl)-1H-benzimidazole-5-carboxamide;
N-[2-(dimethylamino)ethyl]-1-{4-[3-(4-fluorophenoxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-(2-methoxyethyl)-1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-[2-(dimethylamino)ethyl]-1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(2-morpholin-4-ylethyl)-1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-[3-(4-methylpiperazin-1-yl)propyl]-1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-methyl-1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(1-tetrahydro-2H-pyran-4-ylmethyl)-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-[2-(1H-imidazol-2-yl)ethyl]-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(2-hydroxyethyl)-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(3-hydroxypropyl)-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
1-{4-[3-(4-fluorophenoxy)propoxy]phenyl}-N-(2-hydroxyethyl)-1H-benzimidazole-5-carboxamide;
1-{4-[3-(4-fluorophenoxy)propoxy]phenyl}-N-(2-piperidin-1-ylethyl)-1H-benzimidazole-5-carboxamide;
N-(3-morpholin-4-ylpropyl)-1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-[3-(dimethylamino)propyl]-1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(3-methoxypropyl)-1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
5-(morpholin-4-ylcarbonyl)-1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole;
(4-{[1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazol-5-yl]carbonyl}piperazin-1-yl)ethanol;
(1-{[1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazol-5-yl]carbonyl}piperidin-4-yl)ethanol;
N-(2-piperidin-1-ylethyl)-1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
5-[4-(2-methoxyethyl)piperazin-1-ylcarbonyl]-1-[3-(4-trifluoromethoxy-benzyloxy)-phenyl]-1H-benzimidazole;
N-ethyl-1-(3-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
1-{3-[3-(4-fluorophenoxy)propoxy]phenyl}-N-[3-(4-methylpiperazin-1-yl)propyl]-1H-benzimidazole-5-carboxamide;
1-{3-[3-(4-fluorophenoxy)propoxy]phenyl}-N-(3-morpholin-4ylpropyl)-1H-benzimidazole-5-carboxamide;
N-[2-(dimethylamino)ethyl]-1-{3-[2-(4-fluorophenoxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-[3-(dimethylamino)propyl]-1-{3-[2-(4-fluorophenoxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
1-{3-[2-(4-fluorophenoxy)ethoxy]phenyl}-N-(2-methoxyethyl)-1H-benzimidazole-5-carboxamide;
1-{3-[2-(4-fluorophenoxy)ethoxy]phenyl}-N-tetrahydro-2H-pyran-4-yl-1H-benzimidazole-5-carboxamide;
1-{3-[2-(4-fluorophenoxy)ethoxy]phenyl}-N-(1-tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-carboxamide;
N-tetrahydro-2H-pyran-4-yl-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-isopropyl-1-[4-({4-[(trifluoromethyl)thio]benzyl}oxy)phenyl]-1H-benzimidazole-5-carboxamide;
N-(2-morpholin-4ylethyl)-1-[4-({4-[(trifluoromethyl)thio]benzyl}oxy)phenyl]-1H-benzimidazole-5-carboxamide;
N-methyl-1-[4-({4-[(trifluoromethyl)thio]benzyl}oxy)phenyl]-1H-benzimidazole-5-carboxamide;
N-(2-pyrrolidin-1-ylethyl)-1-[4-({4-[(trifluoromethyl)thio]benzyl}oxy)phenyl]-1H-benzimidazole-5-carboxamide;
N-(2-hydroxyethyl)-1-[4-({4-[(trifluoromethyl)thio]benzyl}oxy)phenyl]-1H-benzimidazole-5-carboxamide;
N-(1-tetrahydro-2H-pyran-4-ylmethyl)-1-[4-({4-[(trifluoromethyl)thio]benzyl}oxy)phenyl]-1H-benzimidazole-5-carboxamide;
N-(2-methoxyethyl)-1-(4-{[4-(trifluoromethyl)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
1-(4-{[4-(trifluoromethyl)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-methyl-1-(4-{[4-(trifluoromethyl)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(2-morpholin-4ylethyl)-1-(4-{[4-(trifluoromethyl)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(1-tetrahydro-2H-pyran-4-ylmethyl)-1-(4-{[4-(trifluoromethyl)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-ethyl-1-[4-({4-[(trifluoromethyl)thio]benzyl}oxy)phenyl]-1H-benzimidazole-5-carboxamide;
1-[4-({4-[(trifluoromethyl)thio]benzyl}oxy)phenyl]-1H-benzimidazole-5-carboxamide;
1-(4-{[4-(difluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-methyl-1-(4-{[4-(difluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(2-morpholin-4ylethyl)-1-(4-{[4-(difluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(2-pyrrolidin-1-ylethyl)-1-(4-{[4-(difluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(2-methoxyethyl)-1-(4-{[4-(difluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-isopropyl-1-(4-{[4-(trifluoromethyl)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(2-pyrrolidin-1-ylethyl)-1-(4-{[4-(trifluoromethyl)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(2-hydroxyethyl)-1-(4-{[4-(trifluoromethyl)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-isopropyl-1-(4-{[4-(difluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(1-tetrahydro-2H-pyran-4-ylmethyl)-1-(4-{[4-(difluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
N-(2-pyrrolidin-1-ylethyl)-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide;
1-{4-[2-(pyrazin-2-yloxy)ethoxy]phenyl}-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide;
1-{4-[2-(pyrimidin-2-yloxy)ethoxy]phenyl}-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide;
N-methyl-1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-ethyl-1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-(2-methoxyethyl)-1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-(2-morpholin-4-ylethyl)-1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-N-(1-tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-carboxamide;
1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-N-tetrahydro-2H-pyran-4-yl-1H-benzimidazole-5-carboxamide;
N-cyclobutyl-1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-(2-hydroxyethyl)-1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-N-(2-pyrrolidin-1-ylethyl)-1H-benzimidazole-5-carboxamide;
tert-butyl-4-{[(1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazol-5-yl)carbonyl]amino}ethyl)piperazine-1-carboxylate;
N-isopropyl-1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
1-{4-[1-methyl-2-(pyridin-2-yloxy)ethoxy]phenyl}-N-(2-morpholin-4-ylethyl)-1H-benzimidazole-5-carboxamide;
N-(2-morpholin-4-ylethyl)-1-{4-[2-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-(2-morpholin-4-ylethyl)-1-{4-[1-methyl-2-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
1-{4-[1-methyl-2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
1-{4-[2-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-isopropyl-1-{4-[1-methyl-2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-isopropyl-1-{4-[2-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-(2-hydroxyethyl)-1-{4-[1-methyl-2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-(2-hydroxyethyl)-1-{4-[2-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
1-{4-[1-methyl-2-(pyridin-2-yloxy)ethoxy]phenyl}-N-(2-pyrrolidin-1-ylethyl)-1H-benzimidazole-5-carboxamide;
1-{4-[2-(pyridin-2-yloxy)propoxy]phenyl}-N-(2-Pyrrolidin-1-ylethyl)-1H-benzimidazole-5-carboxamide;
1-{4-[1-methyl-2-(pyridin-2-yloxy)ethoxy]phenyl}-N-(1-tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-carboxamide;
1-{4-[2-(pyridin-2-yloxy)propoxy]phenyl}-N-(1-tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-carboxamide;
1-{4-[1-methyl-2-(pyridin-2-yloxy)ethoxy]phenyl}-N-[3-(methylthio)propyl]-1H-benzimidazole-5-carboxamide;
N-[3-(methylthio)propyl]-1-{4-[2-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
1-{4-[1-methyl-2-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-isopropyl-1-{4-[1-methyl-2-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-(2-hydroxyethyl)-1-{4-[1-methyl-2-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
1-{4-[1-methyl-2-(pyridin-2-yloxy)propoxy]phenyl}-N-(2-pyrrolidin-1-ylethyl)-1H-benzimidazole-5-carboxamide;
1-{4-[1-methyl-2-(pyridin-2-yloxy)propoxy]phenyl}-N-(1-tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-carboxamide;
1-{4-[1-methyl-2-(pyridin-2-yloxy)propoxy]phenyl}-N-[3-(methylthio)propyl]-1H-benzimidazole-5-carboxamide;
N-methyl-1-{4-[1-methyl-2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-methyl-1-{4-[2-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
N-methyl-1-{4-[1-Methyl-2-(pyridin-2-yloxy)propoxy]phenyl}-1H-benzimidazole-5-carboxamide;
1-(4-{[3-(2-pyridyloxymethyl)cyclobutyl]oxy}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[(3-phenoxypropyl)amino]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[4-(4-fluorophenyl)piperidin-1-yl]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[4-(4-fluorophenyl)piperazin-1-yl]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[4-(4-fluorophenyl)piperidin-1-yl]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-{3-[(2-thien-3-ylethyl)amino]phenyl}-1H-benzimidazole-5-carboxamide;
1-[3-(cyclohexylmethylamino)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{4-[(2-phenoxyethyl)amino]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-(3-{[1-(4-chlorophenyl)ethyl]amino}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-(3-{[3-(1H-imidazol-1-yl)propyl]amino}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-[3-(4-pyrimidin-2-ylpiperazin-1-yl)phenyl]-1H-benzimidazole-5-carboxamide;
1-(3-[1,4′]bipiperidinyl-1′-yl-phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-{3-[benzyl(methyl)amino]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
N-isopropyl-1-(4-{[4-(trifluoromethoxy)benzyl]amino}phenyl)-1H-benzimidazole-5-carboxamide;
N-methyl-1-(4-{[4-(trifluoromethoxy)benzyl]amino}phenyl)-1H-benzimidazole-5-carboxamide;
N-(2-morpholin-4-ylethyl)-1-(4-{[4-(trifluoromethoxy)benzyl]amino}phenyl)-1H-benzimidazole-5-carboxamide;
N-tetrahydro-2H-pyran-4-yl-1-(4-{[4-(trifluoromethoxy)benzyl]amino}phenyl)-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-(3-{[4-(trifluoromethoxy)benzyl]amino}phenyl)-1H-benzimidazole-5-carboxamide;
1-{3-[(4-trifluoromethylphenyl)amino]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-(3-{[(4-methylphenyl)sulfonyl]amino}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-(3-{[(4-chlorophenyl)sulfonyl]amino}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-{3-[(thien-2-ylsulfonyl)amino]phenyl}-1H-benzimidazole-5-carboxamide;
N-pyridin-3-ylmethyl-1-[3-({[4-(trifluoromethoxy)phenyl]sulfonyl}amino) phenyl]-1H-benzimidazole-5-carboxamide;
1-(3-{[(2,4-difluorophenyl)sulfonyl]amino}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
1-(3-{[(3,4-dichlorophenyl)sulfonyl]amino}phenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide;
or a pharmaceutically acceptable salt, or N-oxide, thereof.

122 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/921,414Filed 16 Aug 2004
Priority: 21 Aug 2003
Published: 24 Aug 2006
Term ends: Not estimatedThe source records don’t support an estimate.

Classification15 codes

C07D 235/06
Benzimidazoles; Hydrogenated benzimidazoles: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in…
A61P 35/00
Antineoplastic agents
A61P 35/02
Antineoplastic agents: specific for leukemia
A61P 43/00
Drugs for specific purposes, not provided for in groups a61p1/00-a61p41/00

Family

Application60/496,806Us provisional application · filed 21 Aug 2003
US 7,521,448 B2Related patent
US 2006/0189629 A1This patent

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

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Citations

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A compound represented by Formula (I):

or a pharmaceutically acceptable salt or N-oxide thereof, wherein:
one of R11, R12, R13 and R14 is —NR3COR31, —NR3CONR3R31, —NR3SO2R31, —CO2R3, —CO2H, —C0-8alkylNR3R31 or —CONR3R31;
the others each independently F, Cl, C0-3alkyl, C0-8alkoxy, or —N(C0-8alkyl)(C0-8alkyl);
X is a cyclyl or heterocyclyl group, optionally substituted with 1-4 halogen, —NR32R33, —NR32COR33, —NR32CO2R33, —NR32SO2R33, —OR32, —SR32, —SO2R32, —SO2NR32R33, —CO2R32, —CO2H, —CONR32R33, —C0-8alkyl, —C2-8alkenyl, —C2-8alkynyl, —CN, CF3, OCF3, NO2, oxo, cyclyl or heterocyclyl substituents;
Y is absent or
wherein the point of attachment to X can be from either the left or the right as shown;
Ra and Rb are each independently C0-8alkyl or C3-8cycloalkyl;
or Ra and Rb taken together with the C to which they are attached form a saturated or partially unsaturated 3-10 membered ring optionally containing 0-4 N, O, S, SO, or SO2 at the ring nodes, provided that no N, O or S atoms are placed adjacent to each other at ring nodes;
Rc is C0-8alkyl;
or Rc, taken with either Ra or Rb, form a 3-7 membered saturated or partially unsaturated ring;
m is 0, 1, 2, 3, 4 or 5;
provided that when m is 0 or 1, no N, O or S atoms are adjacent to each other in the N—X—Y-Z linking bridge;
n is 1, 2, 3, 4 or 5;
provided that, when n is 1, no N, O or S atoms are adjacent to each other in the N—X—Y-Z linking bridge;
Z is a cyclyl or heterocycyl group, optionally substituted with 1-5 independent halogen, —NR34R35, —NR34COR35, —NR34C(O)OR35, —NR34SO2R35, —OR34, —SR34, —SO2R34, —SO2NR34R35, —C(O)OR34, —CO2H, —CONR34R35, C0-8alkyl, C2-8alkenyl, C2-8alkynyl, —OC0-8alkyl, —SC0-8alkyl, —SO2C0-8alkyl, —SO2N(C0-8alkyl)(C0-8alkyl), —C(O)OC0-8alkyl, CN, CF3, NO2, oxo, cyclyl or heterocyclyl substituents;
or, when Y is present, Z further can be C0-8alkyl-O—C0-8alkyl, C0-8alkyl-O—C(O)—C0-8alkyl, or C0-8alkyl-C(O)—O—C0-8alkyl;
provided that when Y is —OCH2—, Z must be substituted with 1-5-NR34R35, —NR34COR35, —NR34C(O)OR35, —NR34SO2R35, —OR34, —SR34, —SO2R34, —SO2NR34R35, —CO2R34, —CO2H, —CONR34R35, C0-8alkyl, C2-8alkenyl, C2-8alkynyl, CF3, NO2, oxo, cyclyl or heterocyclyl substituents;
provided that when Y is NHCH2, Z must be substituted with 1-5 halogen, —NR34R35, —NR34COR35, —NR34C(O)OR35, —NR34SO2R35, —OR34, —SR34, —SO2R34, —SO2NR34R35, —CO2R34, —CO2H, —CONR34R35, C0-8alkyl, C2-8alkenyl, C2-8alkynyl, CF3, NO2, oxo, cyclyl or heterocyclyl substituents;
provided that when Y is absent, X and Z cannot contain N;
R3, R31, R32, R33, R34 and R35 are independently C0-8alkyl substituted with heterocyclyl, or OH substituents;
CF3, CHF2, —C0-8alkyl-O—C0-8alkyl, —C0-8alkyl-N(C0-8alkyl)(C0-8alkyl), —C0-8alkyl-S(O)0-2—C0-8alkyl or —C0-8alkyl-S(O)2N(C0-8alkyl)(C0-8alkyl).

18 more elements

Facts

Application

10/921,414Filed 16 Aug 2004

Priority

21 Aug 2003

Published

24 Aug 2006

Term ends

Not estimatedThe source records don’t support an estimate.

Classification15 codes

C07D 235/06
Benzimidazoles; Hydrogenated benzimidazoles: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in…
A61P 35/00
Antineoplastic agents
A61P 35/02
Antineoplastic agents: specific for leukemia
A61P 43/00
Drugs for specific purposes, not provided for in groups a61p1/00-a61p41/00