IP Library Granted Patent US 7,396,840
Granted Patent B2
US 7,396,840 · App. 11/345,987 · Granted Jul 8, 2008

Chemokine receptor binding heterocyclic compounds

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Quick Facts
Patent No.
US 7,396,840
App. No.
11/345,987
Granted
Jul 8, 2008
Kind
B2
Abstract

Tertiary amine compounds that bind chemokine receptors such as CXCR4 and CCR5 are disclosed.

Claims (27)

1. A compound of the formula

and the pharmaceutically acceptable salts thereof wherein:

each n is independently 0-2;

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

Ar is phenylene;

each Y is independently optionally substituted pyrimidyl, imidazole, pyridyl, benzimidazole, or benzooxazole; and

L 2 is a covalent bond or a C1-6 alkylene,

wherein said optional substituents are independently halogen, nitro, cyano, carboxylic acid, alkyl, alkenyl, cycloalkyl, hydroxyl, thiol, or amino, acyl;

wherein the hydroxyl and thiol groups may be substituted by C 1-10 alkyl or by C 2-4 alkanoyl; and

wherein an amino group may also be substituted once or twice with C 1-10 alkyl, alkenyl or C 2-4 alkanoyl.

2. The compound of claim 1 , wherein L 2 is methylene or ethylene.

3. The compound of claim 1 , wherein all R coupled directly to ring E are H.

4. A composition comprising the compound of claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

5. The compound of claim 1 , wherein all R are H.

6. The compound of claim 1 , wherein each Y is independently imicazole, benzimidazole or pyridyl.

7. The compound of claim 6 , wherein all R are H.

8. The compound of claim 6 , wherein L 2 is methylene or ethylene.

9. The compound of claim 6 which is

N-(2-pyridinylmethyl)-N′-[cis-2-(N-phenylamino)cyclohexyl]-1,4-benzenedimethanamine;

N-(2-pyridinylmethyl)-N′-[trans-2-[(pyridin-2-ylmethyl) amino]cyclohexyl]-1,4-benzenedimethanamine;

N-(2-pyridinylmethyl)-N′-[cis-2-[(N-pyridin-2-ylmethyl) amino]cyclohexyl]-1,4-benzenedimethanamine;

N-(2-pyridinylmethyl)-N′-[cis-2-[(1H-imidazol-2-ylmethyl)amino]cyclohexyl]-1,4-benzenedimethanamine;

2-{[4-({2-[(pyridin-2-ylmethyl)-amino]-cyclohexylamino}-methyl)-benzylamino]-methyl}-pyridin-3-ol;

N-(2-pyridinylmethyl)-N′-[cis-2-[[(1H)-benzimidazol-2-ylmethyl]amino]]cyclohexyl]-1,4-benzenedimethanamine;

N-[2-(3-hydroxy)pyridinylmethyl]-N′-{cis-2-[[(1H)-benzimidazol-2-ylmethyl]amino]cyclohexyl}-1,4-benzenedimethanamine;

N-(3-hydroxy-2-pyridinylmethyl)-N′-[cis-2-[[imidazol-2-ylmethyl]amino]cyclohexyl]-1,4-benzenedimethanamine;

or a pharmaceutically acceptable salt thereof.