US 2006/0100282 A1Published application

Novel diaminopropane-based metal chelators as antiviral agents

AssigneeBioflexis, LLC

InventorsRaghavan Rajagopalan, John Babu

Life of this patent

Estimating the term…

Loading patent…

Abstract

This invention relates to novel diaminopropane-based divalent metal ion chelating ligands of Formula I, wherein A is selected from the group consisting of —(CH2)a—, —(CH2)bO(CH2)c—, —(CH2O)d—, and —(CH2)eN(R4)(CH2)f—; a and c vary from 0 to 10; b, e, and f vary from 2 to 10, and d varies from 1 to 10. X and Y are independently —CR5R6, or —CH(R7)CH(R8). R1 to R8 are various substituents selected to optimize the physicochemical and biological properties such as enzyme binding, tissue penetration, lipophilicity, toxicity, bioavailability, and pharmacokinetics of compounds of Formula 13. R1 to R8 may include, but are not limited to hydrogen, alkyl, acyl, hydroxyl, hydroxyalkyl, substituted or unsubstituted aryl, amino, aminoalkyl, alkoxyl, aryloxyl, carboxyl, halogen, alkoxycarbonyl, cyano, and other suitable electron donating or electron withdrawing groups. Ar may unsubstituted phenyl group or may be substituted with suitable electron donating or electron withdrawing groups. The compounds of the present invention are useful for inhibiting the activity of viral enzymes responsible for the proliferation of human immunodeficiency virus (HIV).

Claims20

Dependent claims

A compound of Formula I,

wherein A is selected from the group consisting of —(CH2)a—, —(CH2)bO(CH2)c—, —(CH2O)d—, and —(CH2)eN(R4)(CH2)f—;
a and c vary from 0 to 10;
b, e, and f vary from 2 to 10;
and d varies from 1 to 10;
X and Y are independently —CR5R6 or —CH(R7)CH(R8);
R1 to R8 are independently selected from the group consisting of hydrogen;
C1-C10 alkyl;
C1-C10 carboxyalkyl;
C1-C10 alkoxyl;
C1-C10 alkoxycarbonylalkyl;
C1-C10 hydroxyalkyl;
C1-C10 aminoalkyl;
C5-C20 aryl unsubstituted or substituted with C1-C10 alkyl, hydroxyl, C1-C10 alkoxyl, cyano, halo, trihaloalkyl, carboxyl, C1-C10 acyl, C1-C10 hydroxyalkyl, amino, C1-C10 alkylamino, C1-C10 dialkylamino, and C1-C10 alkxoylcarbonyl;
C5-C20 arylalkyl unsubstituted or substituted with C1-C10 alkyl, hydroxyl, C1-C10 alkoxyl, cyano, halo, trihaloalkyl, carboxyl, C1-C10 acyl, C1-C10 hydroxyalkyl, amino, C1-C10 alkylamino, C1-C10 dialkylamino, and C1-C10 alkxoylcarbonyl;
C5-C20 aryloxyl unsubstituted or substituted with C1-C10 alkyl, hydroxyl, C1-C10 alkoxyl, cyano, halo, trihaloalkyl, carboxyl, C1-C10 acyl, C1-C10 hydroxyalkyl, amino, C1-C10 alkylamino, C1-C10 dialkylamino, and C1-C10 alkxoylcarbonyl;
C5-C20 aryloxyalkyl unsubstituted or substituted with C1-C10 alkyl, hydroxyl, C1-C10 alkoxyl, cyano, halo, trihaloalkyl, carboxyl, C1-C10 acyl, C1-C10 hydroxyalkyl, amino, C1-C10 alkylamino, C1-C10 dialkylamino, and C1-C10 alkxoylcarbonyl;
C5-C20 arylalkoxyl unsubstituted or substituted with C1-C10 alkyl, hydroxyl, C1-C10 alkoxyl, cyano, halo, trihaloalkyl, carboxyl, C1-C10 acyl, C1-C10 hydroxyalkyl, amino, C1-C10 alkylamino, C1-C10 dialkylamino, and C1-C10 alkxoylcarbony.

14 more elements

A method of treating viral infection comprising administering to an individual an effective amount of compound of Formula I,

wherein A is selected from the group consisting of —(CH2)a—, —(CH2)bO(CH2)c—, —(CH2O)d—, and —(CH2)eN(R4)(CH2)f—;
a and c vary from 0 to 10;
b, e, and f vary from 2 to 10;
and d varies from 1 to 10;
X and Y are independently —CR5R6 or —CH(R7)CH(R8);
R1 to R8 are independently selected from the group consisting of hydrogen;
C1-C10 alkyl;
C1-C10 carboxyalkyl;
C1-C10 alkoxyl;
C1-C10 alkoxycarbonylalkyl;
C1-C10 hydroxyalkyl;
C1-C10 aminoalkyl;
C5-C20 aryl unsubstituted or substituted with C1-C10 alkyl, hydroxyl, C1-C10 alkoxyl, cyano, halo, trihaloalkyl, carboxyl, C1-C10 acyl, C1-C10 hydroxyalkyl, amino, C1-C10 alkylamino, C1-C10 dialkylamino, and C1-C10 alkxoylcarbonyl;
C5-C20 arylalkyl unsubstituted or substituted with C1-C10 alkyl, hydroxyl, C1-C10 alkoxyl, cyano, halo, trihaloalkyl, carboxyl, C1-C10 acyl, C1-C10 hydroxyalkyl, amino, C1-C10 alkylamino, C1-C10 dialkylamino, and C1-C10 alkxoylcarbonyl;
C5-C20 aryloxyl unsubstituted or substituted with C1-C10 alkyl, hydroxyl, C1-C10 alkoxyl, cyano, halo, trihaloalkyl, carboxyl, C1-C10 acyl, C1-C10 hydroxyalkyl, amino, C1-C10 alkylamino, C1-C10 dialkylamino, and C1-C10 alkxoylcarbonyl;
C5-C20 aryloxyalkyl unsubstituted or substituted with C1-C10 alkyl, hydroxyl, C1-C10 alkoxyl, cyano, halo, trihaloalkyl, carboxyl, C1-C10 acyl, C1-C10 hydroxyalkyl, amino, C1-C10 alkylamino, C1-C10 dialkylamino, and C1-C10 alkxoylcarbonyl;
C5-C20 arylalkoxyl unsubstituted or substituted with C1-C10 alkyl, hydroxyl, C1-C10 alkoxyl, cyano, halo, trihaloalkyl, carboxyl, C1-C10 acyl, C1-C10 hydroxyalkyl, amino, C1-C10 alkylamino, C1-C10 dialkylamino, and C1-C10 alkxoylcarbony.

14 more elements

Dependencies are inferred from the claim text.