US 2012/0071447 A1Published application

Antiviral Drugs for Treatment of Arenavirus Infection

AssigneeSiga Technologies, Inc.

InventorsDongcheng Dai, Sean M. Amberg, Tove Bolken, Dennis E. Hruby

Life of this patent

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Abstract

Methods, compounds, and pharmaceutical compositions for treating an arenavirus infections are disclosed. Methods for preparing the compounds and pharmaceutical compositions are also disclosed. The novel compounds and compositions are used for treatment of an arenavirus infections, which include but are not limited to the following viruses: Junin, Machupo, Guanarito, Sabia, Lassa, Tacaribe, Pichinde, and LCMV.

Claims9

Dependent claims

A method for the treatment of an Arenavirus infection comprising administering in a therapeutically effective amount to a mammal in need thereof, a compound of Formula I below:

wherein R1 and R2 are independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, arylalkyl, aryl, acyl, arylacyl, hydroxy, alkyloxy, alkylthio, amino, alkylamino, acetamido, halogen, cyano or nitro;
R3 is hydrogen, acyl, arylacyl or sulfonyl;
and
Ar1 and Ar2 are independently (un)substituted aryl or heteroaryl;
and wherein compound of Formula I is selected from the group consisting of:
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-propoxy-benzyl)-amine;
(4-Isopropoxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Butoxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Hexyloxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-phenoxy-benzyl)-amine;
(4-Benzyloxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Ethyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-propyl-benzyl)-amine;
(4-Butyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-tert-Butyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
Biphenyl-4-ylmethyl-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-propoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Isopropoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Butoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Hexyloxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-phenoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Ethyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-propyl-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Butyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-tert-Butyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Hexyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Benzyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Hexyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-tert-Butoxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Benzyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(1-Biphenyl-4-yl-1H-benzoimidazol-5-yl)-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-naphthalen-2-yl-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Isopropyl-benzyl)-{1-[4-(naphthalen-2-yloxy)-phenyl]-1H-benzoimidazol-5-yl}-amine;
(4-Isopropyl-benzyl)-[1-(4-phenethyl-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Isopropyl-benzyl)-[1-(4-phenethyloxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-tert-Butoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Dimethylaminomethyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-morpholin-4-ylmethyl-benzyl)-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-phenethyl-benzyl)-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-phenethyloxy-benzyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-ethyl-benzyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(5-methyl-pyridin-2-ylmethyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(6-methyl-pyridin-3-ylmethyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(2-ethyl-pyrimidin-5-ylmethyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-methyl-amine;
hydrochloride;
(4-Ethyl-benzyl)-[1-(6-methoxy-pyridin-3-yl)-1H-benzoimidazol-5-yl]-amine;
(4-Ethyl-benzyl)-[1-(2-methoxy-pyrimidin-5-yl)-1H-benzoimidazol-5-yl]-amine;
(4-Ethyl-benzyl)-[1-(6-methoxy-pyridazin-3-yl)-1H-benzoimidazol-5-yl]-amine;
[1-(6-Ethoxy-pyridin-3-yl)-1H-benzoimidazol-5-yl]-(4-ethyl-benzyl)-amine;
(4-Ethyl-benzyl)-[1-(5-methoxy-pyridin-2-yl)-1H-benzoimidazol-5-yl]-amine;
(4-Isopropyl-benzyl)-[1-(4-methoxy-phenyl)-7-trifluoromethyl-1H-benzoimidazol-5-yl]-amine;
1-(4-ethoxyphenyl)-N-[(4-ethylphenyl)methyl]-2-methyl-benzimidazol-5-amine;
1-(4-ethoxyphenyl)-N-[(4-ethylphenyl)methyl]-2-propyl-benzimidazol-5-amine;
1-(4-ethoxyphenyl)-5-[(4-ethylphenyl)methylamino]benzimidazole-2-carbonitrile;
1-(4-ethoxyphenyl)-N-[(4-ethylphenyl)methyl]-6-methyl-benzimidazol-5-amine;
3-(4-ethoxyphenyl)-N6-[(4-ethylphenyl)methyl]benzimidazole-4,6-diamine hydrochloride;
1-[4-[[[1-(4-ethoxyphenyl)benzimidazol-5-yl]amino]methyl]phenyl]ethanone;
1-(4-ethoxyphenyl)-N5-[(4-ethylphenyl)methyl]benzimidazole-2,5-diamine;
5-[(4-isopropylphenyl)methylamino]-1-(4-methoxyphenyl)benzimidazole-2-carbonitrile;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-piperidin-1-ylmethyl-benzyl)-amine;
[4-(2-Dimethylamino-ethoxy)-benzyl]-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-{[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-ylamino]-methyl}-phenyl)-acetic acid;
5-Dimethylamino-naphthalene-1-sulfonic acid 4-{[1-(4-ethoxy-phenyl)-1H-benzoimidazol-5-ylamino]-methyl}-benzylamide;
[1-(6-Ethoxy-pyridin-3-yl)-1H-benzoimidazol-5-yl]-(5-methyl-pyridin-2-ylmethyl)-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-[4-(4-methyl-piperazin-1-ylmethyl)-benzyl]-amine;
and
[4-(3-Dimethylamino-propoxy)-benzyl]-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine.

66 more elements

A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a pharmaceutically effective amount of a compound of Formula I

wherein R1 and R2 are independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, arylalkyl, aryl, acyl, arylacyl, hydroxy, alkyloxy, alkylthio, amino, alkylamino, acetamido, halogen, cyano or nitro;
R3 is hydrogen, acyl, arylacyl or sulfonyl;
and
Ar1 and Ar2 are independently (un)substituted aryl or heteroaryl;
and a pharmaceutically acceptable carrier therefore, and
wherein the compound of Formula I is selected from the group consisting of:
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-propoxy-benzyl)-amine;
(4-Isopropoxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Butoxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Hexyloxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-phenoxy-benzyl)-amine;
(4-Benzyloxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Ethyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-propyl-benzyl)-amine;
(4-Butyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-tert-Butyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
Biphenyl-4-ylmethyl-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-propoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Isopropoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Butoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Hexyloxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-phenoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Ethyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-propyl-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Butyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-tert-Butyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Hexyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Benzyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Hexyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-tert-Butoxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Benzyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(1-Biphenyl-4-yl-1H-benzoimidazol-5-yl)-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-naphthalen-2-yl-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Isopropyl-benzyl)-{1-[4-(naphthalen-2-yloxy)-phenyl]-1H-benzoimidazol-5-yl}-amine;
(4-Isopropyl-benzyl)-[1-(4-phenethyl-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Isopropyl-benzyl)-[1-(4-phenethyloxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-tert-Butoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Dimethylaminomethyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-morpholin-4-ylmethyl-benzyl)-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-phenethyl-benzyl)-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-phenethyloxy-benzyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-ethyl-benzyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(5-methyl-pyridin-2-ylmethyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(6-methyl-pyridin-3-ylmethyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(2-ethyl-pyrimidin-5-ylmethyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-methyl-amine;
hydrochloride;
(4-Ethyl-benzyl)-[1-(6-methoxy-pyridin-3-yl)-1H-benzoimidazol-5-yl]-amine;
(4-Ethyl-benzyl)-[1-(2-methoxy-pyrimidin-5-yl)-1H-benzoimidazol-5-yl]-amine;
(4-Ethyl-benzyl)-[1-(6-methoxy-pyridazin-3-yl)-1H-benzoimidazol-5-yl]-amine;
[1-(6-Ethoxy-pyridin-3-yl)-1H-benzoimidazol-5-yl]-(4-ethyl-benzyl)-amine;
(4-Ethyl-benzyl)-[1-(5-methoxy-pyridin-2-yl)-1H-benzoimidazol-5-yl]-amine;
(4-Isopropyl-benzyl)-[1-(4-methoxy-phenyl)-7-trifluoromethyl-1H-benzoimidazol-5-yl]-amine;
1-(4-ethoxyphenyl)-N-[(4-ethylphenyl)methyl]-2-methyl-benzimidazol-5-amine;
1-(4-ethoxyphenyl)-N-[(4-ethylphenyl)methyl]-2-propyl-benzimidazol-5-amine;
1-(4-ethoxyphenyl)-5-[(4-ethylphenyl)methylamino]benzimidazole-2-carbonitrile;
1-(4-ethoxyphenyl)-N-[(4-ethylphenyl)methyl]-6-methyl-benzimidazol-5-amine;
3-(4-ethoxyphenyl)-N6-[(4-ethylphenyl)methyl]benzimidazole-4,6-diamine hydrochloride;
1-[4-[[[1-(4-ethoxyphenyl)benzimidazol-5-yl]amino]methyl]phenyl]ethanone;
1-(4-ethoxyphenyl)-N5-[(4-ethylphenyl)methyl]benzimidazole-2,5-diamine;
5-[(4-isopropylphenyl)methylamino]-1-(4-methoxyphenyl)benzimidazole-2-carbonitrile;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-piperidin-1-ylmethyl-benzyl)-amine;
[4-(2-Dimethylamino-ethoxy)-benzyl]-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-{[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-ylamino]-methyl}-phenyl)-acetic acid;
5-Dimethylamino-naphthalene-1-sulfonic acid 4-{[1-(4-ethoxy-phenyl)-1H-benzoimidazol-5-ylamino]-methyl}-benzylamide;
[1-(6-Ethoxy-pyridin-3-yl)-1H-benzoimidazol-5-yl]-(5-methyl-pyridin-2-ylmethyl)-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-[4-(4-methyl-piperazin-1-ylmethyl)-benzyl]-amine;
and
[4-(3-Dimethylamino-propoxy)-benzyl]-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine.

67 more elements

A compound selected from the group consisting of

[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-propoxy-benzyl)-amine;
(4-Isopropoxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Butoxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Hexyloxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-phenoxy-benzyl)-amine;
(4-Benzyloxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Ethyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-propyl-benzyl)-amine;
(4-Butyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-tert-Butyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
Biphenyl-4-ylmethyl-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-propoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Isopropoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Butoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Hexyloxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-phenoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Ethyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-propyl-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Butyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-tert-Butyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Hexyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Benzyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Hexyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-tert-Butoxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Benzyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(1-Biphenyl-4-yl-1H-benzoimidazol-5-yl)-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-naphthalen-2-yl-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Isopropyl-benzyl)-{1-[4-(naphthalen-2-yloxy)-phenyl]-1H-benzoimidazol-5-yl}-amine;
(4-Isopropyl-benzyl)-[1-(4-phenethyl-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Isopropyl-benzyl)-[1-(4-phenethyloxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-tert-Butoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Dimethylaminomethyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-morpholin-4-ylmethyl-benzyl)-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-phenethyl-benzyl)-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-phenethyloxy-benzyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-ethyl-benzyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(5-methyl-pyridin-2-ylmethyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(6-methyl-pyridin-3-ylmethyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(2-ethyl-pyrimidin-5-ylmethyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-methyl-amine;
hydrochloride;
(4-Ethyl-benzyl)-[1-(6-methoxy-pyridin-3-yl)-1H-benzoimidazol-5-yl]-amine;
(4-Ethyl-benzyl)-[1-(2-methoxy-pyrimidin-5-yl)-1H-benzoimidazol-5-yl]-amine;
(4-Ethyl-benzyl)-[1-(6-methoxy-pyridazin-3-yl)-1H-benzoimidazol-5-yl]-amine;
[1-(6-Ethoxy-pyridin-3-yl)-1H-benzoimidazol-5-yl]-(4-ethyl-benzyl)-amine;
(4-Ethyl-benzyl)-[1-(5-methoxy-pyridin-2-yl)-1H-benzoimidazol-5-yl]-amine;
(4-Isopropyl-benzyl)-[1-(4-methoxy-phenyl)-7-trifluoromethyl-1H-benzoimidazol-5-yl]-amine;
1-(4-ethoxyphenyl)-N-[(4-ethylphenyl)methyl]-2-methyl-benzimidazol-5-amine;
1-(4-ethoxyphenyl)-N-[(4-ethylphenyl)methyl]-2-propyl-benzimidazol-5-amine;
1-(4-ethoxyphenyl)-5-[(4-ethylphenyl)methylamino]benzimidazole-2-carbonitrile;
1-(4-ethoxyphenyl)-N-[(4-ethylphenyl)methyl]-6-methyl-benzimidazol-5-amine;
3-(4-ethoxyphenyl)-N6-[(4-ethylphenyl)methyl]benzimidazole-4,6-diamine hydrochloride;
1-[4-[[[1-(4-ethoxyphenyl)benzimidazol-5-yl]amino]methyl]phenyl]ethanone;
1-(4-ethoxyphenyl)-N5-[(4-ethylphenyl)methyl]benzimidazole-2,5-diamine;
5-[(4-isopropylphenyl)methylamino]-1-(4-methoxyphenyl)benzimidazole-2-carbonitrile;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-piperidin-1-ylmethyl-benzyl)-amine;
[4-(2-Dimethylamino-ethoxy)-benzyl]-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-{[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-ylamino]-methyl}-phenyl)-acetic acid;
5-Dimethylamino-naphthalene-1-sulfonic acid 4-{[1-(4-ethoxy-phenyl)-1H-benzoimidazol-5-ylamino]-methyl}-benzylamide;
[1-(6-Ethoxy-pyridin-3-yl)-1H-benzoimidazol-5-yl]-(5-methyl-pyridin-2-ylmethyl)-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-[4-(4-methyl-piperazin-1-ylmethyl)-benzyl]-amine;
and
[4-(3-Dimethylamino-propoxy)-benzyl]-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine.

61 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/293,849Filed 10 Nov 2011
Priority: 2 Mar 2006
Published: 22 Mar 2012
Term ends: Not estimatedThe source records don’t support an estimate.

Classification11 codes

A61K 31/4164
Having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole: 1,3-Diazoles
A61P 31/12
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antivirals
C07D 235/06
Benzimidazoles; Hydrogenated benzimidazoles: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in…
C07D 235/08
With only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2: radicals containing only hydrogen and…

Family

Application60/778,107Us provisional application · filed 2 Mar 2006
Application11/712,918Division · filed 2 Mar 2007
Application12/912,325Continuation in part · filed 26 Oct 2010
Application13/293,849Continuation in part
Application12/912,325Division
US 2007/0254934 A1Published application
US 2011/0172281 A1Published application
US 7,872,037 B2Related patent
US 8,629,170 B2Related patent
US 8,871,746 B2Related patent
US 2012/0071447 A1This patent

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

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Abstract

A method for the treatment of an Arenavirus infection comprising administering in a therapeutically effective amount to a mammal in need thereof, a compound of Formula I below:

wherein R1 and R2 are independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, arylalkyl, aryl, acyl, arylacyl, hydroxy, alkyloxy, alkylthio, amino, alkylamino, acetamido, halogen, cyano or nitro;
R3 is hydrogen, acyl, arylacyl or sulfonyl;
and
Ar1 and Ar2 are independently (un)substituted aryl or heteroaryl;
and wherein compound of Formula I is selected from the group consisting of:
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-propoxy-benzyl)-amine;
(4-Isopropoxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Butoxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Hexyloxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-phenoxy-benzyl)-amine;
(4-Benzyloxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Ethyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-propyl-benzyl)-amine;
(4-Butyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-tert-Butyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
Biphenyl-4-ylmethyl-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-propoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Isopropoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Butoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Hexyloxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-phenoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Ethyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-propyl-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Butyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-tert-Butyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Hexyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
[1-(4-Benzyl-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Hexyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-tert-Butoxy-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Benzyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(1-Biphenyl-4-yl-1H-benzoimidazol-5-yl)-(4-isopropyl-benzyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-naphthalen-2-yl-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Isopropyl-benzyl)-{1-[4-(naphthalen-2-yloxy)-phenyl]-1H-benzoimidazol-5-yl}-amine;
(4-Isopropyl-benzyl)-[1-(4-phenethyl-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-Isopropyl-benzyl)-[1-(4-phenethyloxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-tert-Butoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-isopropyl-benzyl)-amine;
(4-Dimethylaminomethyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-morpholin-4-ylmethyl-benzyl)-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-phenethyl-benzyl)-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-phenethyloxy-benzyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-ethyl-benzyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(5-methyl-pyridin-2-ylmethyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(6-methyl-pyridin-3-ylmethyl)-amine;
[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-(2-ethyl-pyrimidin-5-ylmethyl)-amine;
(4-Isopropyl-benzyl)-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-methyl-amine;
hydrochloride;
(4-Ethyl-benzyl)-[1-(6-methoxy-pyridin-3-yl)-1H-benzoimidazol-5-yl]-amine;
(4-Ethyl-benzyl)-[1-(2-methoxy-pyrimidin-5-yl)-1H-benzoimidazol-5-yl]-amine;
(4-Ethyl-benzyl)-[1-(6-methoxy-pyridazin-3-yl)-1H-benzoimidazol-5-yl]-amine;
[1-(6-Ethoxy-pyridin-3-yl)-1H-benzoimidazol-5-yl]-(4-ethyl-benzyl)-amine;
(4-Ethyl-benzyl)-[1-(5-methoxy-pyridin-2-yl)-1H-benzoimidazol-5-yl]-amine;
(4-Isopropyl-benzyl)-[1-(4-methoxy-phenyl)-7-trifluoromethyl-1H-benzoimidazol-5-yl]-amine;
1-(4-ethoxyphenyl)-N-[(4-ethylphenyl)methyl]-2-methyl-benzimidazol-5-amine;
1-(4-ethoxyphenyl)-N-[(4-ethylphenyl)methyl]-2-propyl-benzimidazol-5-amine;
1-(4-ethoxyphenyl)-5-[(4-ethylphenyl)methylamino]benzimidazole-2-carbonitrile;
1-(4-ethoxyphenyl)-N-[(4-ethylphenyl)methyl]-6-methyl-benzimidazol-5-amine;
3-(4-ethoxyphenyl)-N6-[(4-ethylphenyl)methyl]benzimidazole-4,6-diamine hydrochloride;
1-[4-[[[1-(4-ethoxyphenyl)benzimidazol-5-yl]amino]methyl]phenyl]ethanone;
1-(4-ethoxyphenyl)-N5-[(4-ethylphenyl)methyl]benzimidazole-2,5-diamine;
5-[(4-isopropylphenyl)methylamino]-1-(4-methoxyphenyl)benzimidazole-2-carbonitrile;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-(4-piperidin-1-ylmethyl-benzyl)-amine;
[4-(2-Dimethylamino-ethoxy)-benzyl]-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine;
(4-{[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-ylamino]-methyl}-phenyl)-acetic acid;
5-Dimethylamino-naphthalene-1-sulfonic acid 4-{[1-(4-ethoxy-phenyl)-1H-benzoimidazol-5-ylamino]-methyl}-benzylamide;
[1-(6-Ethoxy-pyridin-3-yl)-1H-benzoimidazol-5-yl]-(5-methyl-pyridin-2-ylmethyl)-amine;
[1-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-[4-(4-methyl-piperazin-1-ylmethyl)-benzyl]-amine;
and
[4-(3-Dimethylamino-propoxy)-benzyl]-[1-(4-methoxy-phenyl)-1H-benzoimidazol-5-yl]-amine.

66 more elements

Facts

Application

13/293,849Filed 10 Nov 2011

Priority

2 Mar 2006

Published

22 Mar 2012

Term ends

Not estimatedThe source records don’t support an estimate.

Classification11 codes

A61K 31/4164
Having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole: 1,3-Diazoles
A61P 31/12
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antivirals
C07D 235/06
Benzimidazoles; Hydrogenated benzimidazoles: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in…
C07D 235/08
With only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2: radicals containing only hydrogen and…

Family

Application60/778,107Us provisional application · filed 2 Mar 2006

Application11/712,918Division · filed 2 Mar 2007

Application12/912,325Continuation in part · filed 26 Oct 2010

Application13/293,849Continuation in part

Application12/912,325Division

US 2007/0254934 A1Published application

US 2011/0172281 A1Published application

US 7,872,037 B2Related patent

US 8,629,170 B2Related patent

US 8,871,746 B2Related patent

US 2012/0071447 A1This patent

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