IP Library › Granted Patent US 7,112,587

Granted Patent B2

US 7,112,587 · App. 10/400,134 · Granted Sep 26, 2006

Methods and compositions of novel triazine compounds

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Patent No.: US 7,112,587
App. No.: 10/400,134
Granted: Sep 26, 2006
Kind: B2

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Abstract

The present invention relates to methods and compositions comprising compounds that treat pathophysiological conditions arising from inflammatory responses. In particular, the present invention is directed to compounds that inhibit or block glycated protein produced induction of the signaling-associated inflammatory response in endothelial cells. The present invention relates to compounds that inhibit smooth muscle proliferation. In particular, the present invention is directed to compounds that inhibit smooth muscle cell proliferation 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.

Claims (349)

1. A compound of the formula Ib:

wherein:

R 1b is selected from

R 2b is selected from

R 3b is selected from

R 4b is selected from —H, —CH 3 , —CH 2 CH 3 , or —CH 2 CH 2 CH 3 ;

R 5b is selected from

R 6b is selected from

R 7b is selected from

2. A compound as claimed in claim 1 , wherein the compound is:

N-Cycloheptyl-N′(1-ethyl-pyrrolidin-2-ylmethyl)-6-(3-fluoro-4-methoxy-phenoxy)-[1,3,5]triazine-2,4-diamine;

6-(3-Chloro-4-methoxy-phenoxy)-N-cycloheptyl-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-[1,3,5]triazine-2,4-diamine;

6-(3-Bromo-4-methoxy-phenoxy)-N-cycloheptyl-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-[1,3,5]triazine-2,4-diamine;

N-Cycloheptyl-N′(1-ethyl-pyrrolidin-2-ylmethyl)-6-(3-iodo-4-methoxy-phenoxy)-[1,3,5]triazine-2,4-diamine;

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

N-(3-Chloro-4-methoxy-benzyl)-N′-cycloheptyl-N″-(1-ethyl-pyrrolidin-2-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

N-(3-Bromo-4-methoxy-benzyl)-N′-cycloheptyl-N″-(1-ethyl-pyrrolidin-2-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-N″-(3-iodo-4-methoxy-benzyl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-N″-[2-(3-fluoro-4-methoxyphenyl)-ethyl]-[1,3,5]triazine-2,4,6-triamine;

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

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

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

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

N-(3-Chloro-4-ethoxy-phenyl)-N′-cycloheptyl-N″-(1-ethyl-pyrrolidin-2-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

N-(3-Bromo-4-ethoxy-phenyl)-N′-cycloheptyl-N″-(1-ethyl-pyrrolidin-2-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(4-ethoxy-3-iodo-phenyl)-N″-(1-ethyl-pyrrolidin-2-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

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

N-(3-Chloro-4-propoxy-phenyl)-N′-cycloheptyl-N″-(1-ethyl-pyrrolidin-2-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

N-(3-Bromo-4-propoxy-phenyl)-N′-cycloheptyl-N″-(1-ethyl-pyrrolidin-2-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-N″-(3-iodo-4-propoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-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″-(1-ethyl-pyrrolidin-2-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

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

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

{4-Cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-yl}-(3-fluoro-4-methoxy-phenyl)-cyanamide;

(3-Chloro-4-methoxy-phenyl)-{4-cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-yl}-cyanamide;

(3-Bromo-4-methoxy-phenyl)-{4-cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-yl}-cyanamide;

{4-Cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-yl}-(3-iodo-4-methoxy-phenyl)-cyanamide;

4-{4-Cycloheptylaminamino-6-[(1-ethylpyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenol;

2-Bromo-4-{4-cycloheptylamino-6-[(1-ethylpyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-phenol;

4-{4-Cycloheptylaminamino-6-[(1-ethylpyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-2-iodo-phenol;

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

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

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

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

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

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

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

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

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

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

N-(1-Ethyl-pyrrolidin-2-ylmethyl)-N′-(3-fluoro-4-methoxy-phenyl)-N″-(1-propyl-butyl)-[1,3,5]triazine-2,4,6-triamine;

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

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

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

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

N-(1-Ethyl-pyrrolidin-2-ylmethyl)-N′-(3-fluoro-4-methoxy-phenyl)-N″-piperidin-1-yl-[1,3,5]triazine-2,4,6-triamine;

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

4-[(1-Ethyl-pyrrolidin-2-ylmethyl)-amino]-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-yl-cyanamide;

N-[4-[(1-Ethyl-pyrrolidin-2-ylmethyl)-amino]-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-acetamide;

3-[4-[(1-Ethyl-pyrrolidin-2-ylmethyl)-amino]-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-pyrrolidin-2-one;

3-[4-[(1-Ethyl-pyrrolidin-2-ylmethyl)-amino]-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidin-2-one;

3-[4-[(1-Ethyl-pyrrolidin-2-ylmethyl)-amino]-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-azepan-2-one;

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

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

N-(1-Ethyl-pyrrolidin-2-ylmethyl)-N′-(3-fluoro-4-methoxy-phenyl)-N″-oxepan-3-yl-[1,3,5]triazine-2,4,6-triamine;

N-(1-Ethyl-pyrrolidin-2-ylmethyl)-N′-(3-fluoro-4-methoxy-phenyl)-N″-(tetrahydropyran-3-yl)-[1,3,5]triazine-2,4,6-triamine;

N-(1-Ethyl-pyrrolidin-2-ylmethyl)-N′-(3-fluoro-4-methoxy-phenyl)-N″-(tetrahydrofuran-3-yl)-[1,3,5]triazine-2,4,6-triamine;

N-(1-Aza-bicyclo[2.2.2]oct-3-yl)-N′-(1-ethylpyrrolidin-2-ylmethyl)-N-″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine;

N-(1-Aza-bicyclo[2.2.1]hept-3-yl)-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-N-″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine;

N-Bicyclo[2.2.1]hept-2-yl-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-N″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine;

[4-[(1-Ethyl-pyrrolidin-2-ylmethyl)-amino]-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-carbamic acid;

[4-[(1-Ethyl-pyrrolidin-2-ylmethyl)-amino]-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-urea;

[4-[(1-Ethyl-pyrrolidin-2-ylmethyl)-amino]-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-propan-2-one;

[4-[(1-Ethyl-pyrrolidin-2-ylmethyl)-amino]-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-pentan-2-one;

N-Cycloheptyl-N′-(3-fluoro-4-methoxyphenyl)-6-(1-methyl-piperidin-4-yloxy)-[1,3,5]triazine-2,4-diamine;

N-Cycloheptyl-6-(1-ethyl-pyrrolidin-2-ylmethoxy)-N′-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine;

1-{4-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-methyl-amino}-piperidin-1-yl}-ethanone;

4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidine-1-carboxylic acid;

4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidine-1-carboxylic acid amide;

4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidin-1-ol;

N-Cycloheptyl-N′-(3-fluoro-4-methoxyphenyl)-N″-piperidin-4-yl-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxyphenyl)-N″-(1-methyl-pyrrolidin-2-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

2-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-pyrrolidine-1-carbaldehyde;

2-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-pyrrolidine-1-carboxylic acid;

2-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-pyrrolidine-1-carboxylic acid amide;

N-Cycloheptyl-N′-(3-fluoro-4-methoxyphenyl)-N″-pyrrolidin-2-ylmethyl-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxyphenyl)-N″-(tetrahydro-pyran-4-yl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxyphenyl)-N″-methyl-(tetrahydro-pyran-4-yl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxyphenyl)-N″-(tetrahydro-furan-2-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxyphenyl)-N″-methyl-N″-(tetrahydro-furan-2-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

N-(4-Amino-cyclohexyl)-N′-cycloheptyl-N″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(4-dimethylaminocyclohexyl)-N″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine;

1-{4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-4H-pyridin-1-yl}-ethanone;

1-{4-[4-cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidin-1-yl}-butan-1-one;

1-{4-[4-cycloheptylamino-6-(3-fluoro-methoxy-phenylamino)-[1,3,5]triazin-ylamino]-piperidin-1-yl}-pentan-1-one;

4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-ylamino]-piperidine-1-carboxylic acid methyl ester;

4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidine-1-carboxylic acid ethylester;

4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-ylamino]-piperidine-1-carboxylic acid propyl ester;

4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidine-1-carboxylic acid benzyl ester;

1-{4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidin-1-yl}-propan-2-one;

1-{4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidin-1-yl}-pentan-2-one;

1-{4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidin-1-yl}-hexan-2-one;

{4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidin-1-yl}-acetic acid methyl ester;

{4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidin-1-yl}-acetic acid ethyl ester;

{4-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-piperidin-1-yl}-acetic acid propyl ester;

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

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

N-(1-Ethyl-pyrrolidin-2-ylmethyl)-N′-(3-fluoro-4-methoxy-phenyl)-N″-(1-methyl-azepan-4-yl)-[1,3,5]triazine-2,4,6-triamine;

N-(1-Ethyl-pyrrolidin-2-ylmethyl)-N′-(3-fluoro-4-methoxy-phenyl)-N″-thiepan-4-yl-[1,3,5]triazine-2,4,6-triamine;

N-(1,1-Dioxo-1lambda*6*-thiepan-4-yl)-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-N″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine;

N-(1-Ethyl-pyrrolidin-2-ylmethyl)-N′-(3-fluoro-4-methoxy-phenyl)-N″-oxepan-2-yl-[1,3,5]triazine-2,4,6-triamine;

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

N-(1-Ethyl-pyrrolidin-2-ylmethyl)-N′-(3-fluoro-4-methoxy-phenyl)-N″-thiepan-2-yl-[1,3,5]triazine-2,4,6-triamine;

N-(1-Ethyl-pyrrolidin-2-ylmethyl)-N′-(3-fluoro-4-methoxy-phenyl)-N″-thiepan-3-yl-[1,3,5]triazine-2,4,6-triamine;

N-(1,1-Dioxo-1lambda*6*-thiepan-3-yl)-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-N″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine;

2-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-1-ethyl-pyrrolidinium; chloride;

2-{[4-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazin-2-ylamino]-methyl}-1-ethyl-pyrrolidinium; chloride;

2-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-1-ethyl-pyrrolidinium; bromide;

2-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-1-ethyl-1-methyl-pyrrolidinium; iodide;

1-Acetyl-2-{[4-cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-1-ethyl-pyrrolidinium; chloride;

Sodium; 4-{4-cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenolate;

Potassium; 4-{4-cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenolate;

3-Carboxy-propionate-2-{[4-cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]methyl}-1-ethyl-pyrrolidinium;

3-Carboxy-acrylate-2-{[4-cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-1-ethyl-pyrrolidinium;

N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-(1-methyl-1H-pyrrol-2-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-6-(1-methyl-1H-pyrrol-2-ylmethoxy)-[1,3,5]triazine-2,4-diamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-6-(thiophen-2-ylmethoxy)-[1,3,5]triazine-2,4-diamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-thiophen-2-ylmethyl-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-furan-2-ylmethyl-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-(tetrahydro-furan-2-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(1,1-dioxo-tetrahydro-1lambda*6*-thiophen-2-ylmethyl)-N″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-N″-(5-fluoro-6-methoxy-pyridin-3-yl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-N″-(4-fluoro-5-methoxy-pyridin-2-yl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-pyridin-2-ylmethyl-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-pyridin-3-ylmethyl-[1,3,5]triazine-2,4,6-triamine;

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

N-Cycloheptyl-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-N″-(4-trifluoromethoxy-3-trifluoromethyl-phenyl)-[1,3,5]triazine-2,4,6-triamine;

4-{4-Cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-2-trifluoromethyl-phenol;

N-Cycloheptyl-N′-(2-ethyl-cyclopentylmethyl)-N″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-(2-methyl-cyclopentyl methyl)-[1,3,5]triazine-2,4,6-triamine;

2-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-cyclopentanol;

N-(2-Amino-cyclopentylmethyl)-N′-cycloheptyl-N″-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4,6-triamine;

3-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-cyclopentanol;

2-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2 ylamino]-cyclopentanol;

N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-6-(tetrahydro-pyrrolo[1,2-c]imidazol-2-yl)-[1,3,5]triazine-2,4-diamine;

2-[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-hexahydro-pyrrolo[1,2-c]imidazol-3-one;

N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-(1H-imidazol-4-ylmethyl)-[1,3,5]triazine-2,4,6-triamine;

N-Cycloheptyl-6-(2,3-dihydro-indol-1-yl)-N′-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine;

N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-6-indol-1-yl-[1,3,5]triazine-2,4-diamine;

1-(2-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-pyrrolidin-1-yl)-3-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propan-1-one;

1-(2-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-pyrrolidin-1-yl)-3-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propan-1-one;

N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-[1-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxymethyl)-pyrrolidin-2-ylmethyl]-[1,3,5]triazine-2,4,6-triamine;

2-(2-{2-[2-(2-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-1,3,5]triazin-2-ylamino]-methyl}-pyrrolidin-1-ylmethoxy)-ethoxy]-ethoxy}-ethoxy)-ethanol;

3-{2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethoxy}-propionic acid 4-{4-cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenyl ester;

3-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethoxy}-propionic acid 4-{4-cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenyl ester;

3-(2-{2-[2-(4-{4-Cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenoxy)-ethoxy]-ethoxy}-ethoxy)-propan-1-ol;

N-Cycloheptyl-N′-(1-ethyl-pyrrolidin-2-ylmethyl)-N″-[3-fluoro-4-(2-{2-[2-(3-methoxy-propoxy)-ethoxy]-ethoxy}-ethoxy)-phenyl]-[1,3,5]triazine-2,4,6-triamine;

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

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

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

4-{4-Cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenol; compound with phosphoric acid monoethyl ester;

4-{4-Cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenol; compound with phosphoric acid dibenzyl ester ethyl ester;

4-{4-Cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenol; compound with phosphoric acid ditert-butyl ester ethyl ester;

Phosphoric acid mono-(4-{4-cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-2-fluoro-phenyl) ester;

5-{4-Cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-2-hydroxy-benzoic acid; compound with ethane;

Sodium; 5-{4-cycloheptylamino-6-[(1-ethyl-pyrrolidin-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino)}-2-methoxy-benzoate;

2-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-1-(di-tert-butoxy-phosphoryloxymethyl)-1-ethyl-pyrrolidinium; chloride;

1-(Bis-benzyloxy-phosphoryloxymethyl)-2-{[4-cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-1-ethyl-pyrrolidinium; chloride;

2-{[4-Cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-1-ethyl-1-phosphonooxymethyl-pyrrolidinium; chloride;

Trifluoro-acetate2-{[4-cycloheptylamino-6-(3-fluoro-4-methoxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-1-ethyl-1-phosphonooxymethyl-pyrrolidinium; or

Phosphoric acid mono-(2-{[4-cycloheptylamino-6-(3-fluoro-4-hydroxy-phenylamino)-[1,3,5]triazin-2-ylamino]-methyl}-pyrrolidin-1-ylmethyl) ester; compound with ethane.

3. A composition comprising a pharmaceutically acceptable carrier and a compound of the formula Ib: