IP Library Patent Application 11956190
Patent Application
App. No. 11/956,190

CHEMOKINE RECEPTOR BINDING HETEROCYCLIC COMPOUNDS

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Patent No.
US None
App. No.
11/956,190
Abstract

Tertiary amines containing a multiplicity of heteroaromatic substituents are useful as chemokine receptor modulators.

Claims (330)

1 . A compound of the Formula

and the salts and prodrug forms thereof,

wherein:

X is a monocyclic (5-6 membered) or fused bicyclic (9-12 membered) unsubstituted or substituted ring system containing at least one heteroatom selected from N, O and S;

Z is H, or is a monocyclic (5-6 membered) or fused bicyclic (9-12 membered) unsubstituted or substituted ring system containing at least one heteroatom selected from N, O and S;

Ar is an optionally substituted aromatic or heteroaromatic ring;

each of L 1 , L 2 and L 3 is independently a bond, CO, SO 2 , or CH 2 , wherein at least one of L 2 and L 3 must comprise CO or SO 2 ; and wherein L 1 can also be alkylene (2-5C) wherein one or two C may optionally be replaced by N and which alkylene may itself optionally be substituted by a bridge alkylene (3-4C); L 2 and L 3 also may be, independently, SO 2 NH, CONH, SO 2 NHCH 2 or CONHCH 2 ;

n is 0, 1 or 2;

each R 1 and R 2 is independently H or straight or branched chain or cyclic alkyl (1-6C) which may optionally be substituted, and wherein R 2 may be alkylene coupled to Y; and

Y comprises at least one aromatic or heteroaromatic or other heterocyclic substituted or unsubstituted ring coupled directly to L 3 .

2 . The compound of claim 1 , wherein L 1 is a bond and wherein X is substituted or unsubstituted dihydroquinoline, tetrahydroquinoline, pyranopyridine, dihydropyranopyridine, thiapyranopyridine, dihydrothiapyranopyridine, dihydronaphthyridine, or tetrahydronaphthyridine.

3 . The compound of claim 1 , wherein L 1 is alkylene as defined in claim 1 , CO or SO 2 and X is a monocyclic (5-6 membered) or fused bicyclic (9-12 membered) unsubstituted or substituted ring system containing at least one heteroatom selected from N, O and S.

4 . The compound of claim 3 , wherein X is an optionally substituted imidazole, oxazole, thiazole, benzimidazole, benzothiazole, or benzoxazole.

5 . The compound of claim 1 , wherein Z is hydrogen.

6 . The compound of claim 1 , wherein Y is an optionally substituted imidazole, benzimidazole, pyridine, pyridine, pyrimidine, or phenyl, wherein the ring nitrogen may optionally be oxidized.

7 . The compound of claim 6 , wherein said optional substituents are selected from the group consisting of halogen, nitrile, alkyl, —OR, —SR, —NR 2 , —NRCOR, —OOCR, —COR, —CONR 2 , —COOR, —NO 2 , —NOH, —CF 3 , where R is H or alkyl (1-6C).

8 . A pharmaceutically acceptable salt of a compound of the formula

or of the formula:

wherein 1 is 0-3, and R′ is OH, MeO, SH SMe, CN, CO 2 Me, F, Cl, Br, NO 2 , CH 3 CO, NH 2 , NHCH 3 , N(CH 3 ) 2 , CH 3 CONH, CH 3 SO 2 NH, CONH 2 , SO 2 NH 2 , CF 3 , or Me;

each of Z 1 , Z 2 and Z 3 is independently CH, CR′ or N, wherein only two of said Z 1 , Z 2 and Z 3 can be N;

and each of L 2 and L 3 is independently a bond, CO, SO 2 , CH 2 , SO 2 NH, CONH, SO 2 NHCH 2 , or CONHCH 2 , wherein at least one of L 2 and L 3 must comprise CO or SO 2 .

9 . The compound of claim 8 , wherein Z 1 and Z 3 are N, and Z 2 is CH.

10 . The compound of claim 8 wherein Z 3 is N and L 3 is CO.

11 . The compound of claim 10 wherein one of L 2 and L 3 is SO 2 and the other is a bond or CH 2 .

12 . The compound of claim 10 wherein one of L 2 and L 3 is CO and the other is a bond or CH 2 .

13 . The compound of claim 1 wherein L 1 is alkylene (2-5C) wherein one C may optionally be replaced by N and which may optionally be substituted by a bridging alkylene (3-4C).

14 . A pharmaceutically acceptable salt of a compound of the formula

wherein 1 is 0-3, and R′ is OH, MeO, SH, SMe, CN, CO 2 Me, F, Cl, Br, NO 2 , CH 3 CO, NH 2 , NHCH 3 , N(CH 3 ) 2 , CH 3 CONH, CH 3 SO 2 NH, CONH 2 , SO 2 NH 2 , CF 3 , or Me;

k is 0-2;

each of Z 1 , Z 2 and Z 3 is independently CH, CR′ or N, wherein only two of said Z 1 , Z 2 and Z 3 can be N;

and X, L 2 and L 3 are as defined in claim 1 .

15 . The compound of claim 14 wherein all of Z 1 , Z 2 and Z 3 are CH or CR′.

16 . The compound of claim 14 wherein Z 3 is N and L 3 is CO.

17 . The compound of claim 14 wherein one of L 2 and L 3 is SO 2 and the other is a bond or CH 2 .

18 . The compound of claim 14 wherein one of L 2 and L 3 is CO and the other is a bond or CH 2 .

19 . A pharmaceutical composition comprising the compound of claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient.

20 . A pharmaceutical composition comprising the compound of claim 8 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient.

21 . A pharmaceutical composition comprising the compound of claim 14 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient.

22 . A compound selected from the group consisting of:

6-(4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one;

N-(4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-7-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

3,5-Dichloro-N-{4-[(5,6,7,8-tetrahydro-quinolin-7-ylamino)-methyl]-benzyl}-isonicotinamide;

N-(4-{[(1-benzenesulfonyl-1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-benzenesulfonamide;

N-(4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-N-methyl-benzenesulfonamide;

Pyridine-2-carboxylic acid-4-{[cis-2-[(N-pyridin-2-ylmethyl)amino]cyclohexyl]-aminomethyl}-benzylamide;

3,5-Dichloro-N-(4-{[(1H-indol-3-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(1-methyl-1H-indol-3-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(1H-indol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(1-methyl-1H-indol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(1H-indol-3-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(1-methyl-1H-indol-3-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(1H-indol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(1-methyl-1H-indol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

N-(4-{[[2-(1H-Benzoimidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

N-(3-{[[2-(1H-Benzoimidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

3,5-Dichloro-N-(4-{[[2-(1-methyl-1H-benzoimidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[2-(1-methyl-1H-benzoimidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[2-(1H-imidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[2-(1H-imidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[2-(1-methyl-1H-imidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[2-(1-methyl-1H-imidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[2-(3H-imidazol-4-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[2-(3H-imidazol-4-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[2-(3-methyl-3H-imidazol-4-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[2-(3-methyl-3H-imidazol-4-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(2-oxazol-5-yl-ethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[2-(2-methyl-oxazol-5-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(2-oxazol-5-yl-ethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[2-(2-methyl-oxazol-5-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(2-oxazol-2-yl-ethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(2-oxazol-2-yl-ethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[2-(4-methyl-oxazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[2-(5-methyl-oxazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[2-(4-methyl-oxazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[2-(5-methyl-oxazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

N-(4-{[{2-[(1H-Benzoimidazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

N-(3-{[{2-[(1H-Benzoimidazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

3,5-Dichloro-N-(4-{[{2-[(1-methyl-1H-benzoimidazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[{2-[(1-methyl-1H-benzoimidazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[{2-[(1-methyl-1H-imidazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[2-[(1-methyl-1H-imidazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[{2-[(1H-imidazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[{2-[(1H-imidazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[{2-[(3H-imidazol-4-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[{2-[(3H-imidazol-4-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[{2-[(2-methyl-3H-imidazol-4-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[{2-[(2-methyl-3H-imidazol-4-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[{2-[(3-methyl-3H-imidazol-4-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[{2-[(3-methyl-3H-imidazol-4-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[piperidin-4-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[piperidin-4-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[pyrrolidin-3-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[pyrrolidin-3-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

2,4-Dimethyl-N-(4-{[piperidin-4-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(3-{[piperidin-4-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(4-{[piperidin-3-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(3-{[piperidin-3-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(4-{[pyrrolidin-3-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(3-{[pyrrolidin-3-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

N-(4-{[[2-(1H-Benzoimidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide;

N-(3-{[[2-(1H-Benzoimidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide;

2,4-Dimethyl-N-(4-{[[2-(1-methyl-1H-benzoimidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(3-{[[2-(1-methyl-1H-benzoimidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

N-(4-{[[2-(1H-Imidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide;

N-(3-{[[2-(1H-Imidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide;

N-(4-{[[2-(3H-Imidazol-4-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide;

N-(3-{[[2-(3H-Imidazol-4-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide;

2,4-Dimethyl-N-(4-{[[2-(3-methyl-3H-imidazol-4-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(3-{[[2-(3-methyl-3H-imidazol-4-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(4-{[(2-oxazol-5-yl-ethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(3-{[(2-oxazol-5-yl-ethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(4-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-(2-thiazol-5-yl-ethyl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(3-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-(2-thiazol-5-yl-ethyl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(4-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-(2-thiazol-2-yl-ethyl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(3-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-(2-thiazol-2-yl-ethyl)-amino]-methyl}-benzyl)-nicotinamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[(3H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[(3H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[(2-methyl-3H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[(2-methyl-3H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[(3-methyl-3H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[(3-methyl-3H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[oxazol-5-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[oxazol-5-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-thiazol-5-ylmethyl-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-thiazol-5-ylmethyl-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[(1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[(1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[(1-methyl-1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[(1-methyl-1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[oxazol-2-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[oxazol-2-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-thiazol-2-ylmethyl-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-thiazol-2-ylmethyl-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[piperidin-4-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[piperidin-4-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[piperidin-3-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[piperidin-3-yl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[[2-(1H-benzoimidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[[2-(1H-benzoimidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[[2-(1H-imidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[[2-(1H-imidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[[2-(1-methyl-1H-imidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[[2-(1-methyl-1H-imidazol-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[(2-oxazol-2-yl-ethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[(2-oxazol-2-yl-ethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-(2-thiazol-2-yl-ethyl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-(2-thiazol-2-yl-ethyl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[[2-(3H-imidazol-4-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[[2-(3H-imidazol-4-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[[2-(3-methyl-3H-imidazol-4-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[[2-(3-methyl-3H-imidazol-4-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[(2-oxazol-5-yl-ethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[(2-oxazol-5-yl-ethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-(2-thiazol-5-yl-ethyl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-(2-thiazol-5-yl-ethyl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[{2-[(1H-benzoimidazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[{2-[(1H-benzoimidazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[{2-[(1H-imidazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[{2-[(1H-imidazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-[((5,6,7,8-tetrahydro-quinolin-8-yl)-{2-[(thiazol-2-ylmethyl)-amino]-ethyl}-amino)-methyl]-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-[((5,6,7,8-tetrahydro-quinolin-8-yl)-{2-[(thiazol-2-ylmethyl)-amino]-ethyl}-amino)-methyl]-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 4-{[{2-[(oxazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

4,6-Dimethyl-pyrimidine-5-carboxylic acid 3-{[{2-[(oxazol-2-ylmethyl)-amino]-ethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

3,5-Dichloro-N-{4-[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-ylamino)-methyl]-benzyl}-isonicotinamide;

3,5-Dichloro-N-{3-[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-ylamino)-methyl]-benzyl}-isonicotinamide;

N-(4-{[(1H-Benzoimidazol-2-ylmethyl)-(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

N-(3-{[(1H-Benzoimidazol-2-ylmethyl)-(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

3,5-Dichloro-N-(4-{[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-(3H-imidazol-4-ylmethyl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-(3H-imidazol-4-ylmethyl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-(3-methyl-3H-imidazol-4-ylmethyl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-(3-methyl-3H-imidazol-4-ylmethyl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-piperidin-4-yl-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-piperidin-4-yl-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-piperidin-3-yl-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-piperidin-3-yl-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-pyrrolidin-3-yl-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-pyrrolidin-3-yl-amino]-methyl}-benzyl)-isonicotinamide;

N-(4-{[[2-(1H-Benzoimidazol-2-yl)-ethyl]-(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

N-(3-{[[2-(1H-Benzoimidazol-2-yl)-ethyl]-(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

3,5-Dichloro-N-[4-({(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-[2-(1-methyl-1H-benzoimidazol-2-yl)-ethyl]-amino}-methyl)-benzyl]-isonicotinamide;

3,5-Dichloro-N-[3-(I (3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-[2-(1-methyl-1H-benzoimidazol-2-yl)-ethyl]-amino}-methyl)-benzyl]-isonicotinamide;

3,5-Dichloro-N-[4-({(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-[2-(1-methyl-1H-imidazol-2-yl)-ethyl]-amino}-methyl)-benzyl]-isonicotinamide;

3,5-Dichloro-N-[3-({(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-[2-(1-methyl-1H-imidazol-2-yl)-ethyl]-amino}-methyl)-benzyl]-isonicotinamide;

3,5-Dichloro-N-[4-({(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-[2-(3H-imidazol-4-yl)-ethyl]-amino}-methyl)-benzyl]-isonicotinamide;

3,5-Dichloro-N-[3-({(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-[2-(3H-imidazol-4-yl)-ethyl]-amino}-methyl)-benzyl]-isonicotinamide;

N-(4-{[{2-[(1H-Benzoimidazol-2-ylmethyl)-amino]-ethyl}-(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

N-(3-{[{2-[(1H-Benzoimidazol-2-ylmethyl)-amino]-ethyl}-(3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

3,5-Dichloro-N-{4-[((3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-{2-[(3H-imidazol-4-ylmethyl)-amino]-ethyl}-amino)-methyl]-benzyl}-isonicotinamide; and

3,5-Dichloro-N-{3-[((3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-{2-[(3H-imidazol-4-ylmethyl)-amino]-ethyl}-amino)-methyl]-benzyl}-isonicotinamide;

or a pharmaceutically acceptable salt thereof.

23 . A pharmaceutically acceptable salt of a compound selected from the group consisting of:

3,5-Dichloro-N-(4-{[(1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(2-methyl-1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(2-methyl-1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(5-methyl-1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(5-methyl-1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(2,5-dimethyl-1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(2,5-dimethyl-1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(1-methyl-1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(1-methyl-1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(1,2-dimethyl-1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(1,2-dimethyl-1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(1,5-dimethyl-1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(1,5-dimethyl-1H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(4-methyl-1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(4-methyl-1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[4-(2-fluoro-phenyl)-1H-imidazol-2-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[4-(3-fluoro-phenyl)-1H-imidazol-2-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[4-(4-fluoro-phenyl)-1H-imidazol-2-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[4-(2-fluoro-phenyl)-1H-imidazol-2-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[4-(3-fluoro-phenyl)-1H-imidazol-2-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[4-(4-fluoro-phenyl)-1H-imidazol-2-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(4-phenyl-1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(4-phenyl-1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(2-phenyl-3H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[2-(2-methoxy-phenyl)-3H-imidazol-4-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[2-(3-methoxy-phenyl)-3H-imidazol-4-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[2-(4-methoxy-phenyl)-3H-imidazol-4-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[2-(2-methoxy-phenyl)-3H-imidazol-4-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[2-(3-methoxy-phenyl)-3H-imidazol-4-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[2-(4-methoxy-phenyl)-3H-imidazol-4-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[4-(2-methoxy-phenyl)-1H-imidazol-2-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[4-(3-methoxy-phenyl)-1H-imidazol-2-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[[4-(4-methoxy-phenyl)-1H-imidazol-2-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[4-(2-methoxy-phenyl)-1H-imidazol-2-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[4-(3-methoxy-phenyl)-1H-imidazol-2-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[[4-(4-methoxy-phenyl)-1H-imidazol-2-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(3H-pyrrol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(3H-pyrrol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(5-methyl-3H-pyrrol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(4-methyl-3H-pyrrol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(5-methyl-3H-pyrrol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(4-methyl-3H-pyrrol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[oxazol-2-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(4-methyl-oxazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(5-methyl-oxazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[oxazol-4-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(2-methyl-oxazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[oxazol-2-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(4-methyl-oxazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(5-methyl-oxazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[oxazol-4-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(2-methyl-oxazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-thiazol-2-ylmethyl-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(4-methyl-thiazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(5-methyl-thiazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-thiazol-4-ylmethyl-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(4-{[(2-methyl-thiazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-thiazol-2-ylmethyl-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(4-methyl-thiazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(5-methyl-thiazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-thiazol-4-ylmethyl-amino]-methyl}-benzyl)-isonicotinamide;

3,5-Dichloro-N-(3-{[(2-methyl-thiazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-isonicotinamide;

N-(4-{[(3H-Imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide;

N-(3-{[(3H-Imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide;

2,4-Dimethyl-N-(4-{[(3-methyl-3H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(3-{[(3-methyl-3H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4,N-Trimethyl-N-(4-{[(3-methyl-3H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4,N-Trimethyl-N-(3-{[(3-methyl-3H-imidazol-4-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

N-(4-{[(1H-Imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide;

N-(3-{[(1H-Imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide;

2,4-Dimethyl-N-(4-{[(1-methyl-1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(3-{[(1-methyl-1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(4-{[oxazol-2-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(3-{[oxazol-2-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(4-{[oxazol-5-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(3-{[oxazol-5-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(4-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-thiazol-5-ylmethyl-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(3-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-thiazol-5-ylmethyl-amino]-methyl}-benzyl)-nicotinamide;

2,4-Dimethyl-N-(4-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-thiazol-2-ylmethyl-amino]-methyl}-benzyl)-nicotinamide; and

2,4-Dimethyl-N-(3-{[(5,6,7,8-tetrahydro-quinolin-8-yl)-thiazol-2-ylmethyl-amino]-methyl}-benzyl)-nicotinamide.

24 . A compound selected from the group consisting of:

N-Pyridin-2-yl-4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzamide;

4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)amino]-methyl}-N-pyridin-2-yl-benzamide;

N-Pyridin-2-ylmethyl-4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzamide;

4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-N-pyridin-2-ylmethyl-benzamide;

[4-(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-aminomethyl]-N-(2-hydroxyphenyl)-benzamide;

N-Pyridinyl-2-yl-3-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzamide;

N-pyridin-2-ylmethyl-3-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzenesulfonamide;

N-Phenyl-3-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzamide;

N-(3-{[(1H-enzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenyl)-benzamide;

N-Pyridin-2-ylmethyl-4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzenesulfonamide;

4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-N-pyridin-2-ylmethyl-benzenesulfonamide;

N-Pyridin-2-ylmethyl-3-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzenesulfonamide;

3-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-N-pyridin-2-ylmethyl-benzenesulfonamide;

3-{[(1H-Benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-N-phenyl-benzenesulfonamide;

3-{[(H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-N-benzyl-benzenesulfonamide;

Pyridine-2-carboxylic acid 4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzylamide;

Pyridine-2-carboxylic acid 4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

3,5-dichloro-N-{4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzyl}-isonicotinamide;

N-(4-{[(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide;

N-(3-{[(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide;

N-(4-{[(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-1-oxy-nicotinamide;

N-(3-{[(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-1-oxy-nicotinamide;

4,6-dimethyl-pyrimidine-5-carboxylic acid 3-{[(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

N-(4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,6-dimethyl-benzamide;

N-(4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

N-(3,5-dichloroisonicotinamide)-N′-(1H-benzimidazol-2-ylmethyl)-N′-(S)-5,6,7,8-tetrahydro-quinolin-8-yl-1,4-benzenedimethanamine;

N-(4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-3,5-dibromo-isonicotinamide;

2-amino-N-(4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-6-chloro-benzamide;

4,6-dimethyl-pyrimidine-5-carboxylic acid 4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

1-(4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-3-phenyl-urea;

1-(4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-3-benzyl-urea;

N-(4-{2-[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-ethyl}-benzyl)-3,5-dichloro-isonicotinamide;

Pyridine-2-carboxylic acid 3-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

N-(3-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,6-dichloro-isonicotinamide;

N-(3-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,6-dimethyl-benzamide;

N-(3-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-3,5-dibromo-isonicotinamide;

2-amino-N-(3-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-6-chloro-benzamide;

N-(3-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

N-(2-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,6-dimethyl-benzamide;

N-(2-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-3,5-dichloro-isonicotinamide;

pyridine-2-carboxylic acid {4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-phenyl}-amide;

pyridine-2-carboxylic acid (4-{[(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenyl)-amide;

N-(4-{[(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenyl)-3,5-dichloro-isonicotinamide;

Pyridine-2-sulfonic acid 4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzylamide;

Pyridine-2-sulfonic acid 4-{[(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide;

N-(4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-N-methyl-benzenesulfonamide;

N-(4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-benzenesulfonamide;

Pyridine-2-sulfonic acid {4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-phenyl}-amide; and

Pyridine-2-sulfonic acid (4-{[(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenyl)-amide;

or a pharmaceutically acceptable salt thereof.

25 . A pharmaceutical composition comprising the compound of claim 22 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient.

26 . A pharmaceutical composition comprising the compound of claim 23 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient.

27 . A pharmaceutical composition comprising the compound of claim 24 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 15, 2008
From: ANORMED CORPORATION
To: GENZYME CORPORATION
Reel/Frame 020518/0053 →