Chemokine receptor binding heterocyclic compounds
View Patent ↗Compounds that bind to chemokine receptors such as CXCR 4 and CCR 5 demonstrate protective effects against infection of cells by human immunodeficiency virus are disclosed. These compounds contain a tertiary amine[[s]] linked to a core nitrogen via an aromatic or heteroaromatic moiety.
1. A compound of the formula
and the salts and pro-drug forms thereof wherein:
A is a six membered carbocyclic, saturated ring
R 1 is halo, nitro, cyano, optionally substituted hydroxy, optionally substituted thiol, optionally substituted amino, carboxylate, carboxamide, sulfonate, sulfonamide, C 2-4 alkanoyl, alkylsulfonyl, or aroyl;
k is 0-1;
L 1 is a covalent bond or C 1-6 alkylene, optionally containing one N, or O;
Ar is phenylene;
each n is independently 0-2;
each R is independently H or alkyl (1-6C); and
Y is a 6-membered heterocyclic group with one N or a 5-membered heterocyclic group;
with the proviso that said compound is other than
AMD7222: N-(1-methylbenzimidazol-2-ylmethyl)-N′-(2-pyridinylmethyl)-N-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine, or
AMD8907: N-(2-pyridinylmethyl)-N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine.
2. The compound of claim 1 , wherein R 1 is halo, alkoxy, or alkyl.
3. The compound of claim 1 , wherein k is 0.
4. The compound of claim 1 , wherein each R is H.
5. The compound of claim 1 , wherein Y is pyridyl.
6. A pharmaceutical composition comprising an effective therapeutic amount of the compound of claim 1 or any of claims 2 - 5 .