Benzimidazole compounds

1. A compound having the Formula I:

wherein:

R 1 is aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, arylsulfonyl, aryloxycarbonyl, alkoxyalkoxyalkyl, alkyl-S—R 7 , alkyl-NH—C(═O)—R 8 or —R 9 —X—R 10 -R 11 )H;

wherein each of the alkyl, aryl, arylalkyl heteroaryl, heteroarylalkyl, heterocycloalkyl, arylsulfonyl, aryloxycarbonyl and alkoxyalkoxyalkyl moieties in each of the foregoing R 1 groups can be optionally substituted with up to 5 groups independently selected from the group consisting of C 1 -C 6 alkyl, OH, hydroxyalkyl, —C(═O)—R 5 ; CN, aryl, alkoxycarbonyl, alkylaryl, arylalkyl, heteroaryl, S-heteroaryl optionally substituted with halogen, heteroarylalkyl optionally substituted with halogen, heterocycloalkyl optionally substituted with amino, NO 2 , halogen, monohaloalkyl, dihaloalkyl, trihaloalkyl, perhaloaryl, perhaloalkylaryl, alkyl-NR 15 R 16 and NR 15 R 16 ;

or one of said alkyl, aryl, arylalkyl heteroaryl, heteroarylalkyl, heterocycloalkyl, arylsulfonyl, aryloxycarbonyl or alkoxyalkoxyalkyl moieties of one of said R 1 groups can be attached to a compound of Formula I at position R 1 thereof;

R 3 and R 4 are independently each halogen, C 1 -C 6 alkyl, trihaloalkyl, alkoxycarbonyl, alkoxy, NR 15 R 16 , and NO 2 , wherein said C 1 -C 6 alkyl, alkoxycarbonyl, and alkoxy groups can each be optionally substituted with NR 15 R 16 ;

R 5 is H, —NHNHR 6 , —NHN═CH—R 6 , heteroaryl, heterocycloalkyl, wherein said hereteroaryl group can be optionally substituted with an aryl or heteroaryl group,

R 6 is aryl, heteroaryl; arylsulfonyl, heteroarylsulfonyl, —C(═S)—NH-aryl, —C(═S)—NH-arylcarbonyl, —C(═S)—NH-heteroarylcarbonyl, —C(═S)—NH-alkylene-R 21 , —C(═O)—NHaryl, —C(═O)—NH-arylcarbonyl, —C(═O)—NH-heteroarylcarbonyl, or —C(═O)—NH-alkylene-R 21 where R 21 is carboxy, alkoxycarbonyl, aryl, heteroaryl, heterocycloalkyl, arylaminocarbonyl, cycloalkylaminocarbonyl, or a saturated hydrocarbon fused ring system optionally having an aryl ring fused thereto, said ring system being optionally substituted with up to three alkyl groups on the alkyl or aryl rings thereof;

wherein any of said R 6 groups can be optionally substituted with up to 3 groups selected from NR 15 R 16 , alkyl, hydroxy, halogen, aryl, alkoxy, trihaloalkoxy, arylalkyloxy, NO 2 , —SH, —S-alkyl, heteroarylcarbonyl, heteroaryl, alkylheteroaryl, or a moiety of formula —OC 2 CH 2 —O— attached to adjacent atoms of said R 6 group;

R 7 is heteroaryl or heterocycloalkyl;

R 8 is aryl;

R 9 and R 10 are each independently alkylene having from 1 to about 20 carbons;

X is —N(R 12 )—, —C(R 13 )(R 14 )— or O;

R 11 is H, heteroaryl, or alkoxy, wherein said heteroaryl, or alkoxy group can be optionally substituted with up to four groups independently selected from halogen, amino, trihaloalkyl, alkoxycarbonyl, and CN;

R 12 is H or C 1 -C 6 alkyl; and

R 13 and R 14 are each independently H or C 1 -C 6 alkyl,

R 15 is H, halogen, C 1-12 alkyl, methylcarbonyl, heterocycloalkyl, arylsulfonyl, heteroarylalkyl, aminoalkyl, arylcarbonyl, branched and straight chain polyaminoalkyl, or a group of formula CH 2 (CHOH) 4 CH 2 OH,

wherein said methylcarbonyl, heterocycloalkyl, arylsulfonyl, heteroarylalkyl, aminoalkyl, arylcarbonyl, and branched and straight chain polyaminoalkyl groups can be substituted by up to 3 OH groups;

R 16 is H, halogen, or C 1 -C 6 alkyl;

or R 15 and R 16 together with the nitrogen atom to which they are attached can form a succinimido or phthalimido group or a fused ring derivative thereof, wherein said succinimido or phthalimido group or fused ring derivative thereof can be optionally substituted by up to three substituents independently selected from NO 2 and halogen, or a group of Formula I at position R 1 thereof;

or R 15 and R 16 together with the nitrogen atom to which they are attached can form a group of Formula I wherein said nitrogen atom is Q4 thereof.

2. The compound of claim 1 wherein R 3 and R 4 are each independently halogen, amino, NO 2 , CN, C 1-6 alkoxy or C 1-6 alkyl optionally substituted with up to 3 halogen atoms.

3. The compound of claim 1 wherein R 3 and R 4 are each independently halogen, amino, or NO 2 .

4. The compound of claim 1 wherein R 3 and R 4 are each independently halogen.

5. The compound of claim 1 wherein R 3 and R 4 are each chlorine.

6. The compound of claim 1 wherein R 1 is alkyl substituted with alkoxycarbonyl, alkyl substituted with carboxy, or aralkyl where said aryl portion of said aralkyl is phenyl, pyridinyl, or pyrimidinyl, and where said phenyl, pyridinyl, or pyrimidinyl portion of said arylalkyl group is optionally substituted with up to 5 substituents selected from halogen, monohaloalkyl, dihaloalkyl, trihaloalkyl, NO 2 , alkoxycarbonyl, and alkyl.

7. The compound of claim 5 wherein R 1 is alkyl substituted with alkoxycarbonyl, alkyl substituted with carboxy, or aralkyl where said aryl portion of said aralkyl is phenyl, pyridinyl, or pyrimidinyl, and where said phenyl, pyridinyl, or pyrimidinyl portion of said arylalkyl group is optionally substituted with up to 5 substituents selected from halogen, monohaloalkyl, dihaloalkyl, trihaloalkyl, NO 2 , alkoxycarbonyl, and alkyl.

8. The compound of claim 6 wherein said phenyl, pyridinyl, or pyrimidinyl portion of said arylalkyl group is optionally substituted with up to 5 substituents selected from CF 3 , F, Cl, NO 2 , COOCH 3 , I, Br, and t-butyl.

9. The compound of claim 7 wherein said phenyl, pyridinyl, or pyrimidinyl portion of said arylalkyl group is optionally substituted with up to 5 substituents selected from CF 3 , F, Cl, NO 2 , COOCH 3 , I, Br, and t-butyl.

10. The compound of claim 1 wherein said R 1 is selected from the radicals consisting of:

11. The compound of claim 1 wherein R 1 is alkyl substituted with —C(═O)—R 5 .

12. The compound of claim 11 wherein R 5 is —NHNHR 6 , or —NHN═CH—R 6 .

13. The compound of claim 12 wherein R 5 is —NHNHR 6 .

14. The compound of claim 12 wherein R 5 is —NHN═CH—R 6 .

15. The compound of claim 13 wherein R 6 is —C(═O)—NH-aryl, —C(═O)—NHcycloalkyl,—C(═S)—NH-aryl, arylsulfonyl, heteroarylsulfonyl, heterocycloalkyl, arylaminocarbonyl, cycloalkylaminocarbonyl, —C(═S)—NH-alkylene-R 21 where R 21 is heteroaryl, or a saturated hydrocarbon fused ring system optionally having an aryl ring based thereto, said ring system being optionally substituted with up to three alkyl groups on the alkyl or aryl rings thereof,

wherein any of said R 6 groups can be optionally substituted with up to 3 groups selected from NR 15 R 16 , NO 2 , a moiety of formula —OC 2 CH 2 —O— attached to adjacent atoms of said R 6 group, aryl, C 1-6 alkoxy, carboxy, or C 1-6 trihaloalkoxy.

16. The compound of claim 14 wherein R 6 is aryl or heteroaryl optionally selected from up to 3 groups selected from OH, C 1-6 alkoxy, NO 2 , C 1-6 trihaloalkoxy, C 1-6 trihaloalkyl, aryl, arylalkyloxy, and a moiety of formula —OC 2 CH 2 —O— attached to adjacent atoms of said R 6 group.

17. The compound of claim 13 wherein said R 6 is any of the radicals from the group consisting of:

18. The compound of claim 14 wherein said R 6 is any of the radicals of the group consisting of:

19. The compound of claim 5 wherein R 1 has the formula —(CH 2 ) q —L 4 where q is 0 to 6 and L 4 is aryl, heteroaryl or heterocycloalkyl, arylsulfonamino, arylcarboxyamino or —S-heteroaryl, where each of said L 4 is optionally substituted with up to three substituents selected from halogen and NO 2 .

20. The compound of claim 19 wherein said L 4 is N-maleimidyl, Nsuccinimidyl, N-phthalimidyl, N-naphthalimidyl, N-pyromellitic diimidyl, phenylsulfonamidyl, phenylcarboxamidyl, N-benzopyrrolidinyl, benzimidazol-1-yl; benzimidazol-2-yl, 1,2,4-triazolyl-4-yl, or purinyl, each of said L 4 groups being optionally substituted with 1 or 2 substituents selected from halogen, trihaloalkyl, trihaloalkoxy and NO 2 .

21. A compound of formula:

wherein:

R 52 and R 53 are each independently selected from H, halogen, C 1 -C 6 alkyl, trihaloalkyl, alkoxycarbonyl, alkoxy;

or R′ 15 and R′ 16 together with the nitrogen atom to which they are attached can form a succinimido or phthalimido group or a fused ring derivative thereof, wherein said succinimido or phthalimido group or fused ring derivative thereof can be optionally substituted by up to three substituents independently selected from NO 2 and halogen; and

z is 1 to 6.

22. The compound of claim 21 wherein z is 2 or 3.

23. The compound of claim 22 wherein R 52 and R 53 are each independently H, C 1-6 alkyl, alkoxy optionally substituted with dialkylamino, or alkylamino.

24. The compound of claim 23 wherein R 52 is H.

25. The compound of claim 24 wherein R 53 is methyl, methoxy, alkoxy optionally substituted with dialkylamino, or alkylamino.

26. The compound of claim 24 wherein R 53 is OCH 3 or O(CH 2 ) 3 N(CH 3 ) 2 .

27. The compound of claim 23 wherein R 53 is H.

28. The compound of claim 27 wherein R 52 is methyl, methoxy, alkoxy optionally substituted with dialkylamino, or alkylamino.

29. The compound of claim 27 wherein R 52 is OCH 3 or O(CH 2 ) 3 N(CH 3 ) 2 .