IP Library Granted Patent US 7,335,656
Granted Patent B2
US 7,335,656 · App. 11/512,863 · Granted Feb 26, 2008

Medical devices employing triazine compounds and compositions thereof

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Quick Facts
Patent No.
US 7,335,656
App. No.
11/512,863
Granted
Feb 26, 2008
Kind
B2
Abstract

The present invention relates to methods, compounds, and compositions comprising compounds that treat pathophysiological conditions arising from inflammatory responses, and is directed to compounds that inhibit or block glycated protein produced induction of the signaling-associated inflammatory response in endothelial cells. The present invention also relates to compounds that inhibit smooth muscle proliferation, for example, by modulating HSPGs such as Perlecan. The present invention further relates to the use of compounds to treat vascular occlusive conditions characterized by smooth muscle proliferation such as restenosis and atherosclerosis. This invention also relates to medical devices, such as a stent, comprising a compound or composition of this invention disposed on or within the medical device.

Claims (126)

1. A stent comprising a compound disposed on or within the stent, the compound having the following formula:

or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof; wherein:

R 1a is selected from

R 2a is selected from

R 3a is selected from —H,

R 4a is selected from —H or —CH 3 ;

R 5a is selected from

R 6a is selected from —H or —CH 3 ; and

R 7a is selected from.

2. A stent according to claim 1 , wherein the compound of formula Ia is:

N-Cycloheptyl-N′-(3-iodo-4-methoxyphenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(4-methoxy-3-nitro-phenyl)-N″-methyl-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; 5-{4-Cycloheptylamino-6-[methyl-(1methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino}-2-methoxy-benzonitrile; N-Cycloheptyl-N′-(4-ethoxy-3-fluoro-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-propoxy-phenyl)-N″-methyl-N″-(1-methylpiperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-isopropoxy-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-ethoxy-phenyl)-N′-cycloheptyl-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-propoxy-phenyl)-N′-cycloheptyl-N″-methyl-N″-(1-methylpiperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-isopropoxy-phenyl)-N-cycloheptyl-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(4-methoxy-3-trifluoromethyl-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-benzyl)-N″-methyl-N″-(1-methylpiperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-benzyl)-N′-cycloheptyl-N″-methyl-N″-(1-methylpiperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-[2-(3-fluoro-4-methoxy-phenyl)-ethyl]-N″-methyl-N″(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-[2-(3-Chloro-4-methoxy-phenyl)-ethyl]-N′-cycloheptyl-N″-methyl-N″(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-trifluoromethyl-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl )-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N′-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-benzyl)-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-benzyl)-N″-methyl-N″-piperidin4-yl-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N′,N″-dimethyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-methyl-N″-(4-methylcyclohexyl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-cyclohexyl-N″-(3-fluoro-4-methoxy-phenyl)-N′,N″-dimethyl-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N′, N″-dimethyl-N″-(1-methyl-piperidin-3-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N′,N″-dimethyl-N″-piperidin-3-yl-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N′,N″-dimethyl-N″-(1-methyl-1,4-dihydro-pyridin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N′,N″-dimethyl-N″-pyridin-4-yl-[1,3,5]triazine-2,4,6-triamine; 4-({4-Cycloheptylamino-6-[(3-fluoro-4-methoxy-phenyl)-methyl-amino]-[1,3,5]triazin-2-yl}-methyl-amino)-1methyl-pyridinium, chloride; Acetic acid 4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenyl ester; N-Cycloheptyl-N′-(5-fluoro-6-methoxy-pyridin-3-yl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(4-fluoro-5-methoxy-pyridin-2-yl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-methyl-N″-(4-methylpiperidin-1-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-(4-trifluoromethoxy-3-trifluoromethyl-phenyl)-[1,3,5]triazine-2,4,6-triamine; N-(4-Amino-3-fluoro-phenyl)-N′-cycloheptyl-N″-methyl-N″-(1-methyl-piperidin-4-y)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methylamino-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(4-dimethylamino-3-fluoro-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; 6-(3-Chloro-4-methylamino-phenoxy)-N-cycloheptyl-N′-methyl-N′-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4-diamine; N-(3-Chloro-4-dimethylamino-phenyl)-N′-cycloheptyl-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-6-(3-fluoro-4-methoxy-phenoxy)-N′-methyl-N′-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4-diamine; 6-(3-Chloro-4-methoxy-phenoxy)-N-cycloheptyl-N′-methyl-N′-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4-diamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N,N″-dimethyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cyclohept-4-phenyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methyl-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(4-ethyl-3-fluorophenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-cyclohexyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5 ]triazine-2,4,6-triamine; N-Cyclohept-3-enyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N,N″-dimethyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; 4-{4-Cycloheptylamino-6-[methyl-(1methyl-piperidin-4-yl)-amino]-[1,3,5triazin-2-ylamino}-2-fluoro-phenol; Sodium; 4-{4-(1-ethyl-hexylamino)-6-[methyl-(1-methyl-piperidin-4-yl)amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenolate; N-Cyclohept-2-enyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; 2-Chloro-4-[4-cycloheptylamino-6-(1-methyl-piperidin-4-ylamino)-[1,3,5]triazin-2-ylamino]-phenol; 4-[4-Cycloheptylamino-6-(1-methyl-piperidin-4-ylamino)-[1,3,5]triazin2-ylamino]-2-fluoro-phenol; N-(3-Chloro-4-methoxy-phenyl)-N′-cyclohept-2-enyl-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-methyl-N″-piperidin-4-yl-[1,3,5]triazine-2,4,6-triamine; N-(3-Bromo-4-methoxy-phenyl)-N′-cycloheptyl-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; 4-[4-Cycloheptylamino-6-(methyl-piperidin-4-yl-amino)-[1,3,5]triazin-2-ylamino]-2-fluoro-phenol; 2-Chloro-4-[4-cycloheptylamino-6-(methyl-piperidin-4-yl-amino)-[1,3,5]triazin-2-ylamino]-phenol; Sodium; 2-chloro-4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino)-phenolate; N-(3-Chloro-4-methoxymethoxy-phenyl-N′-cycloheptyl-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; Phosphoric acid mono-(2-chloro-4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino)-phenoxymethyl) ester; Monosodium salt, phosphoric acid mono-(2-chloro-4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino-[1,3,5]triazine-2-ylamino)-phenoxymethyl) ester; N-(3-Chloro-4-methylsulfanylmethoxy-phenyl)-N′-cycloheptyl-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; Phosphoric acid di-tert-butyl ester 2-chloro-4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino}-phenoxymethyl ester; N-Cycloheptyl-N′-(3-fluoro-4-methoxymethoxy-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; Phosphoric acid dibenzyl ester 2-chloro-4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]1,3,5]triazin-2-ylamino}-phenoxymethyl ester; Phosphoric acid mono-(4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenoxymethyl) ester; 2-(2-{2-[2-(2-Chloro-4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3, 5]triazin-2-ylamino}-phenoxy)-ethoxy]-ethoxyl -ethoxy)-ethanol; 2-(2-{2-[2-(4-{4-Cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenoxy)-ethoxy]-ethoxy}-ethoxy)-ethanol; 4-{[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-yl]-methyl-amino)-1-methyl-1-phosphonooxymethyl-piperidinium, chloride; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-methyl-N″-pyridin-4yl-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-methyl-N″-pyridin-4yl-[1,3,5]triazine-2,4,6-triamine; Phosphoric acid mono-(4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenyl) ester; Phosphoric acid mono-(4-{[4-cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-methyl-amino}-piperidin-1-ylmethyl) ester; 4-{[4-Cycloheptylamino-6-(3-fluoro4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-methyl-amino)-1-methyl-1-phosphonooxymethyl-piperidinium, chloride; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-pyridin-4-yl-[1,3,5]triazine-2,4,6-triamine; 4-{[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptyl amino-[1,3,5]triazin-2-yl]-methyl-amino}-1-methyl-pyridinium, chloride; 4-{[4-Cycloheptylamino-6-(3-fluoro4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-methyl-amino}-1,1-di methyl-piperidinium, iodide; N-Allyl-N′-(3-chloro-4-methoxy-phenyl )-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-propyl-[1,3,5]triazine-2,4,6-triamine; N-(3-Fluoro-4-methoxy-phenyl)-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-propyl-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-methyl-N″-(3-methylamino-propyl)-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-(3-dimethylamino-propyl)-N″-methyl-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-(3-dimethylamino-propyl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-dimethylamino-propyl)-N″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine; 6-Azepan-1-yl-N-(3-chloro-4-methoxy-phenyl)-N′-methyl-N′-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4-diamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-methoxymethyl-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-piperidin-1-yl-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-(1-ethyl-piperidin-4yl)-N″-methyl-[1,3,5]triazine-2,4,6-triamine; 4-{[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-yl]-methyl-amino)-piperidine-1-carbaldehyde; 4-{[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-yl]-methyl-amino)-cyclohexanol; N-(1-Aza-bicyclo[2.2.2]oct-3-yl)-N′-(3-chloro-4-methoxy-phenyl)-N″-cycloheptyl-[1,3,5]triazine-2,4,6-triamine; N-Bicyclo[2.2.2]oct-2-yl-N′-(3-chloro-4-methoxy-phenyl)-N″-cycloheptyl-[1,3,5]triazine-2,4,6-triamine; N-(1-Aza-bicyclo[2.2.2]oct-3-yl)-N′-cycloheptyl-N″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine; N-Bicyclo[2.2.2]oct-2-yl-N′-cycloheptyl-N″-(3-flouro-4-methoxy-phenyl-[1,3,5]triazine-2,4,6-triamine; N-Bicyclo[2.2.1]hept-2-yl-N′-(3-chloro-4-methoxy-phenyl)-N″-cycloheptyl-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptylidene-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-(4-Amino-cyclohexyl)-N′-(3-chloro-4-methoxy-phenyl)-N″-cycloheptyl-N-methyl-[1,3,5]triazine-2,4,6-triamine; N-(4-Amino-cyclohexyl)-N′-(3-chloro-4-methoxy-phenyl)-N″-cycloheptyl[1,3,5]triazine-2,4,6-triamine; 3-{[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-yl]-methyl-amino)-cyclohexanol; 3-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-methyl-amino)-cyclohexanol; N-(3-Amino-cyclohexyl)-N′-(3-chloro-4-methoxy-phenyl)-N″-cycloheptyl-N-methyl-[1,3,5]triazine-2,4,6-triamine; N-(4-Amino-cyclohexyl)-N′-cycloheptyl-N″-(3-fluoro-4-methoxy-phenyl)-N-methyl-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-(4-dimethylamino-cyclohexyl)-N″-methyl-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-(4-methoxy-cyclohexyl-N″-methyl-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-(4-methoxy-cyclohexyl-N″-methyl-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-(4-dimethylamino-cyclohexyl)-[1,3,5]triazine-2,4,6-triamine; 4-[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-ylamino]-cyclohexanethiol; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-(4-methylsulfanyl-cyclohexyl)-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-(4-methanesulfonyl-cyclohexyl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-(4-methanesulfonyl-cyclohexyl)-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-thiepan-4-yl-[1,3,5]triazine-2,4,6-triamine; 6-(Bicyclo[2.2.1]hept-2-yloxy)-N-(3-chloro-4-methoxy-phenyl)-N′-methyl-N′-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4-diamine; N-(3-Chloro-4-methoxy-phenyl)-N′-(1,1-dioxo-1lambda*6*-thiepan-4-yl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-(1,1-Dioxo-1-lambda*6*-thiepan-4-yl)-N′-(3-fluoro-4-methoxy-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-thiepan-3-yl-[1,3,5]triazine-2,4,6-triamine; 5-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-thiazolidine-2,4-dione; 5-{[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-ylamino]-methyl)-thiazolidine2,4-dione; 5-{[4-Cycloheptylamino-6-(3-fluoro-4-hydroxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-thiazolidine-2,4-dione; 5-{[4-(3-Chloro-4-hydroxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-ylamino]-methyl}-thiazolidine-2,4-dione; 6-(Bicyclo[2.2.1]hept-2-yloxy)-N-(3-fluoro-4-methoxy-phenyl)-N′-methyl-N′-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4-diamine; 4-[4-Cycloheptylamino-6-(hydroxymethyl-amino)-[1,3,5]triazin-2-ylamino]-2-fluoro-phenol; 5-({4-(3-Fluoro-4-methoxy-phenylamino)-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino)-methyl)-thiazolidine-2,4-dione; Sodium, 4-[4-cycloheptylamino-6-(pyrrolidine-2-carbonyloxy)-[1,3,5]triazin-2-ylamino]-2-fluoro-phenolate; N-Cycloheptyl-N′-(2,3-dihydro-1H-indol-2-ylmethyl)-N″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine; 4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-cyclohexanethiol; 2-{[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-yl]-methyl-amino)-cyclohexanol; N-(2-Amino-cyclohexyl)-N′-(3-chloro-4-methoxy-phenyl)-N″-cycloheptyl-N-methyl-[1,3,5]triazine-2,4,6-triamine; N-(2-Amino-cyclohexyl)-N′-cycloheptyl-N″-(3-fluoro-4-methoxy-phenyl)[1,3,5]triazine-2,4,6-triamine; 4-[4-(2-Amino-cyclohexylamino)-6-cycloheptylamino-[1,3,5]triazin-2-ylamino]-2-fluoro-phenol; 2-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-cyclohexanol; N-(3-Fluoro-4-methoxy-phenyl)-N′-(2-methyl-cyclohexyl)-N″-(1-methyl-hexyl)-[1,3,5]triazine-2,4,6-triamine; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-(3-methyl-cyclohexyl)-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-(3-methyl-cyclohexyl)-[1,3,5]triazine-2,4,6-triamine; 3-(2-{2-[2-(2-Hydroxy-ethoxy)-ethoxoy]-ethoxy}-ethoxy)-propionic acid 4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenylester; 3-(2-{2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethoxy)-ethoxy)-propionic acid 4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin4-yl)-amino]-[1,3,5]triazin-2-ylamino)-2-fluoro-phenyl ester; 3-(2-{2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethoxy)-ethoxy)-propionic acid 2-chloro-4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino)-phenyl ester; 3-(2-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethoxy)-ethoxy)-propionic acid 2-chloro-4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino)-phenylester; 1-{4-[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-ylamino]-piperidin-1-yl)-3-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]ethoxy)-ethoxy)-propan-1-one; 1-{4-[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-ylamino]-piperidin-1-yl)-3-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]ethoxy}-ethoxy)-propan-1-one; 1-{4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidin-1-yl}-3-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]ethoxy}-ethoxy)-propan-1-one; 1-{4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidin-1-yl}-3-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]ethoxy}-ethoxy)-propan-1-one; 4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-1-{2-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy)-ethoxy)-ethoxy]-ethyl)-1-methyl-piperidinium, chloride; 4-[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-ylamino]-1-{2-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy)-ethoxy)-ethoxy]-ethyl}-1-methyl-piperidinium, chloride; 4-[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-ylamino]-1-{2-[2-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy)-ethoxy)-ethoxy]-ethyl)-1-methyl-piperidinium, chloride; 4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-1-{2-[2-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy)-ethoxy)-ethoxy]-ethyl)-1-methyl-piperidinium, chloride; 5-{4-Cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino)-2-methoxy-benzoic acid; 5-{4-Cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino)-2-methoxy-benzoic acid ethyl ester; Sodium, 5-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino}-2-methoxy-benzoate; 4-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-methyl-amino)-1-methyl-piperidinium, chloride; 4-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-methyl-amino)-1-methyl-piperidinium, bromide; 4-{[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-yl]-methyl-amino)-1-methyl-piperidinium, bromide; 3-Carboxy-propionate-4-{[4-(3-chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-yl]-methyl-amino}-1-methyl-piperidinium; 3-Carboxy-acrylate4-{[4-(3-chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-yl]-methyl-amino}-1-methyl-piperidinium; Carboxy-methanecarboxylate-4-{[4-(3chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-yl]methyl-amino}-1-methyl-piperidinium; Carboxy-methanecarboxylate4-{[4-cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]methyl-amino)-1-methyl-piperidinium; 3-Carboxy-acrylate-4-{[4-(3-chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-yl]-methyl-amino}-1-methyl-piperidinium; 4-[4-(3-Chloro-4-hydroxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-ylamino]-piperidinium, chloride; 4-[4-Cycloheptylamino-6-(3-fluoro-4-hydroxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidinium, chloride; 4-{4-Cycloheptylamino-6-[1-(4-methoxy-benzyl)-piperidin-4-ylamino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenol; 4-[4-Cycloheptylamino-6-(piperidin-4-ylamino)-[1,3,5]triazin-2-ylamino]-2-fluoro-phenol; 4-[4-Cyclopropylamino-6-(piperidine-4-ylamino)-[1,3,5]triazin-2-ylamino]-2-fluoro-phenol; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-methyl-N″-(1-methyl-1-oxy-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-methyl-N″-(-methyl 1-oxy-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; 4-{4-Cycloheptylamino-6-[methyl-(1-methyl-1-oxy-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenol; 2-Chloro-4-{4-cycloheptylamino-6-[methyl-(1-methyl-1-oxy-piperidin-4-yl)-amino]-[1,3,5]triazin-2-ylamino}-phenol; N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-(1-methanesulfonyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-N″-(1-methanesulfonyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine; or any combination thereof.

3. A stent comprising a composition disposed on or within the stent, the composition comprising a pharmaceutically acceptable carrier and a compound according to claim 1 .

4. A stent according to claim 3 , wherein the composition further comprises at least one of the following:

a pharmaceutically acceptable auxiliary;

a pharmaceutically acceptable preservative;

a pharmaceutically acceptable excipient; or any combination thereof.

5. A stent comprising a compound disposed on or within the stent, the compound having the following formula:

or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof; wherein:

G is NH or NMe;

E is N or CH;

X 1 is selected from m-F, m-Cl, m-Br, m-I, m-NO 2 , m-CN, m-CF 3 , m-C(O)OEt, or m-C(O)ONa;

X 2 is selected from p-OCH 3 , p-OEt, p-O-n-Pr, p-O-i-Pr, p-OCF 3 , p-OC(O)Me, p-NH 2 , p-NHMe, p-NMe 2 , p-Me, p-Et, p-OH, p-ONa, p-OP(O)(OH) 2 , p-OCH 2 OP(O)(OH) 2 , p-OCH 2 OP(O)(OH)(ONa), p-OCH 2 OP(O)(O-t-Bu) 2 , p-OCH 2 OP(O)(OCH 2 Ph) 2 , p-OCH 2 SMe, p-OCH 2 OMe, p-O(CH 2 CH 2 O) 3 CH 2 CH 2 OH, p-OC(O)(CH 2 CH 2 O) 4 CH 2 CH 2 OH, or p-OC(O)(CH 2 CH 2 O) 4 CH 2 CH 2 OMe,

R 1 is H;

z is 0, 1, or 2;

either: a) A is NH or NMe, and Y 1 is selected from

or b) AY 1 in combination is selected from

 and

either: a) D is NH, NMe, or O, and Y 2 is selected from —H,

or b) DY 2 in combination is selected from

6. A stent comprising a composition disposed on or within the stent, the composition comprising a pharmaceutically acceptable carrier and a compound according to claim 5 .

7. A stent according to claim 6 , wherein the composition further comprises at least one of the following:

a pharmaceutically acceptable auxiliary;

a pharmaceutically acceptable preservative;

a pharmaceutically acceptable excipient; or any combination thereof.

8. A stent comprising a compound disposed on or within the stent, the compound having the following formula:

or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof; wherein:

R 1a is selected from

R 6a is selected from H or Me;

R x is selected from

wherein R 2a is selected from H or Me; and

R 3a is selected from H,

9. A stent comprising a composition disposed on or within the stent, the composition comprising a pharmaceutically acceptable carrier and a compound according to claim 8 .

10. A stent according to claim 9 , wherein the composition further comprises at least one of the following:

a pharmaceutically acceptable auxiliary;

a pharmaceutically acceptable preservative;

a pharmaceutically acceptable excipient; or any combination thereof.

11. A stent comprising a compound disposed on or within the stent, the compound having the following formula:

or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof; wherein:

R 1a is selected from

R 7a is selected from

wherein R 4a is selected from H or Me; and

R 5a is selected from

12. A stent comprising a composition disposed on or within the stent, the composition comprising a pharmaceutically acceptable carrier and a compound according to claim 11 .

13. A stent according to claim 12 , wherein the composition further comprises at least one of the following:

a pharmaceutically acceptable auxiliary;

a pharmaceutically acceptable preservative;

a pharmaceutically acceptable excipient; or

any combination thereof.

14. A stent comprising a compound disposed on or within the stent, the compound having the following formula:

or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof; wherein:

R 1a is selected from,

R 2a is selected from

R 3a is selected from —H

R 5a is selected from

R 6a is selected from —H or —CH 3 .

15. A stent comprising a composition disposed on or within the stent, the composition comprising a pharmaceutically acceptable carrier and a compound according to claim 14 .

16. A stent according to claim 15 , wherein the composition further comprises at least one of the following:

a pharmaceutically acceptable auxiliary;

a pharmaceutically acceptable preservative;

a pharmaceutically acceptable excipient; or

any combination thereof.

17. A stent comprising a compound disposed on or within the stent, wherein the compound is selected from:

4-benzyloxy-3-chloro-phenylamine,

N-(4-benzyloxy-3-chloro-phenyl)-N′-cycloheptyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine,

N-(4-benzyloxy-3-chloro-phenyl)-N′-cycloheptyl-N″-methyl-N″-piperidin4-yl-[1,3,5]triazine-2,4,6-triamine,

4-[4-cycloheptylamino-6-(methyl-piperidin-4-yl-amino)-[1,3,5]triazin-2-ylamino]-phenol,

4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino]-1,3,5]triazin-2-ylamino}-phenol,

2-chloro-4-(4,6-dichloro-[1,3,5]triazin-2-ylamino)-phenol,

2-chloro-4-(4-chloro-6-cycloheptylamino-[1,3,5]triazin-2-ylamino)-phenol,

N-(1-benzyl-piperidin-4-yl)-N′-(3-fluoro-4-methoxy-phenyl)-N″-cycloheptyl-[1,3,5]triazine-2,4,6-diamine,

N-cycloheptyl-N′-(4-methoxy-phenyl)-N″-piperidin-4-yl-[1,3,5]triazine-2,4,6-triamine,

6-chloro-N-cyclopropyl-N′-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine,

N-cyclopropyl-N′-(3-flouro-4-methoxy-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine,

N-cyclopropyl-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-N″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine,

6-chloro-N-(3-chloro-4-methoxypheny 1)-N′-cyclopropyl-[1,3,5]triazine-2,4-diamine,

N-cyclopropyl-N′-(3-chloro-4-methoxyphenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine,

6-chloro-N,N′-bis-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine, N-(1-ethyl-pyrrolidin-2-ylmethyl)-N′,N″-bis-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine,

1-[4-(3-chloro-4-methoxyanilino)-cycloheptyl amino-1,3,5-triazin-2-yl]-2-azoloamymethanol,

N 2 -(3-chloro-4-methoxyphenyl)-N 4 -cycloheptyl-6-(4-methylpiperzino)-1,3,5-triazine-4,2-diamine,

3-[4-(3-chloro-4-methoxyanilino)-6-cycloheptylamino-1,3,5-triazin-2-yloxy]-2-ethyl-4H-4-pyranone,

1-[3-{4-(3-chloro-4-methoxyanilino)-6-cycloheptylamino-1,3,5-triazine-2-yloxy}piperidino]-1-ethanone,

N 2 -(3-chloro-4-methoxyphenyl)-N 4 -cycloheptyl-6-isopropoxy-1,3,5-triazine-2,4-diamine,

N 2 -(3-chloro-4-methoxyphenyl)-N 4 -cycloheptyl-6-(2-azolanylmethoxy)-1,3,5-triazine-2,4-diamine,

1-[4-(3-chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazine-2-yl]-piperidin-3-ol],

1-[4-(3-chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazine-2-yl]-piperidin-4-ol],

N 2 -(3-chloro-4-methoxyphenyl)-N 4 -cycloheptyl-6-(1-methyl-2-azolanylmethoxy)-1,3,5-triazine-2,4-diamine,

N 2 -(3-chloro-4-methoxyphenyl)-N 4 -cycloheptyl-6-(1-methyl-4-piperidyloxy)-1,3,5-triazine-2,4-diamine,

N 2 -(3-chloro-4-methoxyphenyl)-N 4 -cycloheptyl-6-(1,4-thiazinan-4-yl)-1,3,5-triazine-4,2-diamine,

N 2 -(3-chloro-4-methoxyphenyl)-N 4 -cycloheptyl-6-(2-fluorophenoxy)-1,3,5-triazine-4,2-diamine,

N 2 -(3-chloro-4-methoxyphenyl)-N 4 -cycloheptyl-6-[2-(2-fluorophenoxy)ethoxy]-1,3,5-triazine-4,2-diamine,

N 2 -(3-chloro-4-methoxyphenyl)-N 4 -cycloheptyl-6-(6-methyl-2-pyryl methoxy]-1,3,5-triazine-4,2-diamine,

N-(3-chloro-4-methoxyphenyl)-N′-cycloheptyl-N″-methyl-N″-(1-methyl piperidin-4-yl)[1,3,5]triazine-2,4,6-triamine,

N-(3-chloro-4-methoxyphenyl)-N′-cycloheptyl-N″-methyl-N″-(1-methyl piperidin-4-yl)[1,3,5]triazine-2,4,6-triamine, HCl salt,

6-methoxy-N-(3-Chloro-4-methoxy phenyl)-N′-cycloheptyl-[1,3,5]triazine-2,4 diamine,

6-ethoxy-N-(3-Chloro-4-methoxy phenyl)-N′-cycloheptyl-[1,3,5]triazine-2,4diamine,

6-isopropoxy-N-(3-Chloro-4-methoxy phenyl)-N′-cycloheptyl-[1,3,5]triazine-2,4 diamine,

N-(3-chloro-4-methoxyphenyl)-N′-cycloheptyl-N″-methyl-N″-(1-methyl piperidin-4-yl)[1,3,5]triazine-2,4,6-triamine,

6-chloro-N-(3-chloro-4-methoxy-phenyl1)-N′-cycloheptyl-[1,3,5]triazine-2,4-diamine,

(3-chloro-4-methoxy-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine,

6-Chloro-N-(3-fluoro-4-methoxy-phenyl)-N′-cycloheptyl-[1,3,5]triazine-2,4-diamine, or

(3-fluoro-4-methoxy-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine;

or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof.

18. A stent comprising a composition disposed on or within the stent, the composition comprising a pharmaceutically acceptable carrier and a compound according to claim 17 .

19. A stent according to claim 18 , wherein the composition further comprises at least one of the following:

a pharmaceutically acceptable auxiliary;

a pharmaceutically acceptable preservative;

a pharmaceutically acceptable excipient; or

any combination thereof.

20. A stent comprising a compound disposed on or within the stent, wherein the compound is selected from:

or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof.

21. A stent comprising a composition disposed on or within the stent, the composition comprising a pharmaceutically acceptable carrier and a compound according to claim 20 .

22. A stent according to claim 21 , wherein the composition further comprises at least one of the following:

a pharmaceutically acceptable auxiliary;

a pharmaceutically acceptable preservative;

a pharmaceutically acceptable excipient; or

any combination thereof.

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE ADDRESS OF THE RECEIVING PARTY AS LISTED ON THE PATENT ASSIGNMENT COVER SHEET ATTACHED HERETO AND PREVIOUSLY RECORDED ON REEL 023985 FRAME 0502. ASSIGNOR(S) HEREBY CONFIRMS THE CORRECT ADDRESS OF THE RECEIVING PARTY IS 7-1-27, AMEERPET, HYDERABAD-500016, INDIA.. Recorded Jul 6, 2010
From: REDDY US THERAPEUTICS, INC.
To: DR. REDDY'S LABORATORIES LTD.
Reel/Frame 024630/0384 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2010
From: REDDY US THERAPEUTICS, INC.
To: DR. REDDY'S LABORATORIES LTD.
Reel/Frame 023985/0502 →