BENZIMIDAZOLE COMPOUNDS FOR MODULATING IgE AND INHIBITING CELLULAR PROLIFERATION
First Claim
Patent Images
1. A compound or salt thereof having the one of the following formulas:
- wherein R is selected from the group consisting of H, C1-C5 alkyl, benzyl, p-fluorobenzyl and dialkylamino alkyl, wherein said C1-C5 alkyl is selected from the group consisting of a straight chain, branched or cyclic alkyl;
wherein R1 and R2 are independently selected from the group consisting of H, alkyl, substituted alkyl, C3-C9 cycloalkyl, substituted C3-C9 cycloalkyl, polycyclic aliphatic groups, substituted polycyclic aliphatic groups, phenyl, substituted phenyl, naphthyl, substituted naphthyl, five-member ring heteroaryl, and substituted five-member ring heteroaryl, wherein said five-member ring heteroaryl and said substituted five-member ring heteroaryl contain 1-2 heteroatoms, wherein said heteroatom is independently selected from the group consisting of nitrogen, oxygen and sulfur;
wherein R3 and R4 are independently selected from the group consisting of H, alkyl, aryl, heteroaryl and COR′
;
wherein R′
is selected from the group consisting of alkyl, substituted alkyl, C3-C9 cycloalkyl, substituted C3-C9 cycloalkyl, polycyclic aliphatic group, substituted polycyclic aliphatic group, phenyl, substituted phenyl, naphthyl, substituted naphthyl, heteroaryl and substituted heteroaryl, wherein said heteroaryl, and said substituted heteroaryl contain 1-3 heteroatoms, wherein said heteroatom is independently selected from the group consisting of nitrogen, oxygen and sulfur;
wherein R′
is not haloalkyl and provided that when R′
is pyridyl, substituted pyridyl or pyridyl-N-oxide, R1 and R2 are not adamantyl or substituted adamantyl;
wherein said substituted alkyl, substituted polycyclic aliphatic groups, substituted phenyl, substituted naphthyl and substituted heteroaryl contain 1-5 substituents, wherein said substituent is selected from the group consisting of H, halogens, polyhalogens, alkoxy group, substituted alkoxy, alkyl, substituted alkyl, dialkylaminoalkyl, hydroxyalkyl, OH, OCH3, COOH, OCOR′
, COOR′
, COR′
, CN, CF3, OCF3, NO2, NR′
R′
, NHCOR′ and
CONR′
R′
;
wherein the substituent on R1, R2, and R′
is selected from the group consisting of H, halogens, polyhalogens, alkoxy group, substituted alkoxy, alkyl, substituted alkyl, dialkylaminoalkyl, hydroxyalkyl, carbonyl, OH, OCH3, COOH, OCOR′
, COOR′
, COR′
, CN, CF3, OCF3, NO2, NR′
R′
, NHCOR′ and
CONR′
R′
;
wherein X and Y are independently selected from the group consisting of H, halogens, alkoxy, substituted alkoxy, alkyl, substituted alkyl, dialkylaminoalkyl, hydroxyalkyl, OH, OCOR″
, OCH3, COOH, CN, CF3, OCF3, NO2, COOR″
, CHO and COR″
;
wherein R″
is a C1-C8 alkyl, wherein said C1-C8 alkyl is selected from the group consisting of a straight chain, branched or cyclic alkyl;
wherein at least one of R1, R2, R3, or R4 is not H;
wherein R is selected from the group consisting of H, C1-C5 alkyl, benzyl, p-fluorobenzyl and di-alkylamino alkyl, wherein said C1-C5 alkyl is selected from the group consisting of a straight chain, branched or cyclic alkyl;
wherein R1 and R2 are independently selected from the group consisting of H, alkyl, substituted alkyl, C3-C9 cycloalkyl, substituted C3-C9 cycloalkyl, polycyclic aliphatic groups, phenyl, substituted phenyl, naphthyl, substituted naphthyl, heteroaryl and substituted heteroaryl, wherein said heteroaryl and said substituted heteroaryl contain 1-3 heteroatoms, wherein said heteroatom is independently selected from the group consisting of nitrogen, oxygen and sulfur;
wherein said substituted phenyl, substituted naphthyl and substituted heteroaryl contain 1-5 substituents, wherein said substituent is selected from the group consisting of H, halogens, polyhalogens, alkoxy group, substituted alkoxy, alkyl, substituted alkyl, dialkylaminoalkyl, hydroxyalkyl, OH, OCH3, COOH, COOR′
COR′
, CN, CF3, OCF3, NO2, NR′
R′
, NHCOR′ and
CONR′
R′
;
wherein R3 and R4 are independently selected from the group consisting of H, alkyl, aryl, heteroaryl and COR′
;
wherein R′
is selected from the group consisting of H, alkyl, substituted alkyl, C3-C9 cycloalkyl, substituted C3-C9 cycloalkyl, polycyclic aliphatics, phenyl, substituted phenyl, naphthyl, substituted naphthyl, heteroaryl and substituted heteroaryl, wherein said heteroaryl and said substituted heteroaryl contain 1-3 heteroatoms, wherein said heteroatom is independently selected from the group consisting of nitrogen, oxygen and sulfur;
wherein X and Y are independently selected from the group consisting of H, halogens, alkoxy, substituted alkoxy, alkyl, substituted alkyl, dialkylaminoalkyl, hydroxyalkyl, OH, OCOR″
, OCH3, COOH, CN, CF3, OCF3, NO2, COOR″
, CHO and COR″
; and
wherein R″
is a C1-C8 alkyl, wherein said C1-C8 alkyl is selected from the group consisting of a straight chain, branched or cyclic alkyl.
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Abstract
The present invention is directed to small molecule inhibitors of the IgE response to allergens, which are useful in the treatment of allergy and/or asthma or any diseases where IgE is pathogenic. This invention also relates to benzimidazole molecules that are cellular proliferation inhibitors and thus are useful as anticancer agents.
46 Citations
38 Claims
-
1. A compound or salt thereof having the one of the following formulas:
-
wherein R is selected from the group consisting of H, C1-C5 alkyl, benzyl, p-fluorobenzyl and dialkylamino alkyl, wherein said C1-C5 alkyl is selected from the group consisting of a straight chain, branched or cyclic alkyl;
wherein R1 and R2 are independently selected from the group consisting of H, alkyl, substituted alkyl, C3-C9 cycloalkyl, substituted C3-C9 cycloalkyl, polycyclic aliphatic groups, substituted polycyclic aliphatic groups, phenyl, substituted phenyl, naphthyl, substituted naphthyl, five-member ring heteroaryl, and substituted five-member ring heteroaryl, wherein said five-member ring heteroaryl and said substituted five-member ring heteroaryl contain 1-2 heteroatoms, wherein said heteroatom is independently selected from the group consisting of nitrogen, oxygen and sulfur;
wherein R3 and R4 are independently selected from the group consisting of H, alkyl, aryl, heteroaryl and COR′
;
wherein R′
is selected from the group consisting of alkyl, substituted alkyl, C3-C9 cycloalkyl, substituted C3-C9 cycloalkyl, polycyclic aliphatic group, substituted polycyclic aliphatic group, phenyl, substituted phenyl, naphthyl, substituted naphthyl, heteroaryl and substituted heteroaryl, wherein said heteroaryl, and said substituted heteroaryl contain 1-3 heteroatoms, wherein said heteroatom is independently selected from the group consisting of nitrogen, oxygen and sulfur;
wherein R′
is not haloalkyl and provided that when R′
is pyridyl, substituted pyridyl or pyridyl-N-oxide, R1 and R2 are not adamantyl or substituted adamantyl;
wherein said substituted alkyl, substituted polycyclic aliphatic groups, substituted phenyl, substituted naphthyl and substituted heteroaryl contain 1-5 substituents, wherein said substituent is selected from the group consisting of H, halogens, polyhalogens, alkoxy group, substituted alkoxy, alkyl, substituted alkyl, dialkylaminoalkyl, hydroxyalkyl, OH, OCH3, COOH, OCOR′
, COOR′
, COR′
, CN, CF3, OCF3, NO2, NR′
R′
, NHCOR′ and
CONR′
R′
;
wherein the substituent on R1, R2, and R′
is selected from the group consisting of H, halogens, polyhalogens, alkoxy group, substituted alkoxy, alkyl, substituted alkyl, dialkylaminoalkyl, hydroxyalkyl, carbonyl, OH, OCH3, COOH, OCOR′
, COOR′
, COR′
, CN, CF3, OCF3, NO2, NR′
R′
, NHCOR′ and
CONR′
R′
;
wherein X and Y are independently selected from the group consisting of H, halogens, alkoxy, substituted alkoxy, alkyl, substituted alkyl, dialkylaminoalkyl, hydroxyalkyl, OH, OCOR″
, OCH3, COOH, CN, CF3, OCF3, NO2, COOR″
, CHO and COR″
;
wherein R″
is a C1-C8 alkyl, wherein said C1-C8 alkyl is selected from the group consisting of a straight chain, branched or cyclic alkyl;
wherein at least one of R1, R2, R3, or R4 is not H;
wherein R is selected from the group consisting of H, C1-C5 alkyl, benzyl, p-fluorobenzyl and di-alkylamino alkyl, wherein said C1-C5 alkyl is selected from the group consisting of a straight chain, branched or cyclic alkyl;
wherein R1 and R2 are independently selected from the group consisting of H, alkyl, substituted alkyl, C3-C9 cycloalkyl, substituted C3-C9 cycloalkyl, polycyclic aliphatic groups, phenyl, substituted phenyl, naphthyl, substituted naphthyl, heteroaryl and substituted heteroaryl, wherein said heteroaryl and said substituted heteroaryl contain 1-3 heteroatoms, wherein said heteroatom is independently selected from the group consisting of nitrogen, oxygen and sulfur;
wherein said substituted phenyl, substituted naphthyl and substituted heteroaryl contain 1-5 substituents, wherein said substituent is selected from the group consisting of H, halogens, polyhalogens, alkoxy group, substituted alkoxy, alkyl, substituted alkyl, dialkylaminoalkyl, hydroxyalkyl, OH, OCH3, COOH, COOR′
COR′
, CN, CF3, OCF3, NO2, NR′
R′
, NHCOR′ and
CONR′
R′
;
wherein R3 and R4 are independently selected from the group consisting of H, alkyl, aryl, heteroaryl and COR′
;
wherein R′
is selected from the group consisting of H, alkyl, substituted alkyl, C3-C9 cycloalkyl, substituted C3-C9 cycloalkyl, polycyclic aliphatics, phenyl, substituted phenyl, naphthyl, substituted naphthyl, heteroaryl and substituted heteroaryl, wherein said heteroaryl and said substituted heteroaryl contain 1-3 heteroatoms, wherein said heteroatom is independently selected from the group consisting of nitrogen, oxygen and sulfur;
wherein X and Y are independently selected from the group consisting of H, halogens, alkoxy, substituted alkoxy, alkyl, substituted alkyl, dialkylaminoalkyl, hydroxyalkyl, OH, OCOR″
, OCH3, COOH, CN, CF3, OCF3, NO2, COOR″
, CHO and COR″
; and
wherein R″
is a C1-C8 alkyl, wherein said C1-C8 alkyl is selected from the group consisting of a straight chain, branched or cyclic alkyl.- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31)
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-
32. A compound or salt thereof selected from the group consisting of:
-
33. A compound or salt thereof selected from the group consisting of:
-
34. A compound or salt thereof selected from the group consisting of:
-
35. A compound or salt thereof selected from the group consisting of:
-
36. A compound or salt thereof selected from the group consisting of:
-
37. A compound or salt thereof selected from the group consisting of:
-
38. A compound or salt thereof selected from the group consisting of:
Specification