Chemokine receptor binding heterocyclic compounds

1. A compound of the formula

and the salts thereof

wherein

R 1 is selected from halo, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyl, substituted or unsubstituted amino, substituted or unsubstituted thiol, and substituted or unsubstituted acyl;

k is 0–3;

each n is independently 0 or 1;

each R is independently H or alkyl (1–6C);

W is pyridyl, oxazolyl, or imidazolyl; wherein W is optionally substituted with Y j ;

j is 0–3;

each Y is benzyl, halo, or

−(CR 2 ) m NR 5 2 ;

wherein R is H or alkyl (1–6C), m is independently 0–4, and each R 5 is independently H, alkyl (1–6C), alkenyl (2–6C), alkynyl (2–6C), or acyl (1–6C), each optionally substituted by one or more nonaromatic, nonheterocyclic substituent(s) and a indicates the linker between Ring A and N and b indicates the linker between ring E and the N.

2. The compound of claim 1 , wherein E comprises a pi bond coupled to one N.

3. The compound of claim 1 , wherein k is 0–1.

4. The compound of claim 1 , wherein one of (CR 2 ) a n and (CR 2 ) b n is CH 2 and the other is a bond.

5. The compound of claim 4 , wherein (CR 2 ) a n is a bond and (CR 2 ) b n is CH 2 .

6. The compound of claim 1 , wherein W is optionally substituted with benzyl, halo, or (CR 2 ) m —NH 2 where m=0–1.

7. The compound of claim 1 , wherein said compound is selected from the group consisting of

(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-[(1-benzyl-2-aminomethyl)-imidazol-5-ylmethyl)]-amine;

6-aminomethylpyridin-3-ylmethyl-(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-amine;

(6-aminopyridin-3-ylmethyl)-(benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-amine;

(2-aminopyridin-3-ylmethyl)-(benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-8-quinolinyl)-amine;

(6-amino-pyridin-2-ylmethyl)-(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine;

(4-amino-pyridin-3-ylmethyl)-(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine;

(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-(imidazol-2-yl)-methylamine;

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

pyridin-2-ylmethyl-(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-amine;

(1H-benzimidazol-2-ylmethyl)-pyridin-4-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine;

(1H-benzimidazol-2-ylmethyl)-pyridin-3-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine; and

(1H-Benzimidazol-2-ylmethyl)-(3H-imidazol-4-ylmethyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine;

or a salt thereof.

8. A pharmaceutical composition comprising a therapeutically effective amount of the compound of claim 1 and a pharmaceutically acceptable carrier.

9. The pharmaceutical composition of claim 8 , wherein (CR 2 ) a n is a bond and (CR 2 ) b n is CH 2 .

10. The pharmaceutical composition of claim 8 , wherein ring E comprises a pi bond coupled to one N.

11. A pharmaceutical composition for modulating chemokine receptor activity comprising a therapeutically effective amount of the compound of claim 7 and a pharmaceutically acceptable carrier.

12. The pharmaceutical composition of claim 8 , wherein k is 0–1.