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US 6,150,359 AGranted
Naphthyridinones for inhibiting protein tyrosine kinase and cell cycle kinase mediated cellular proliferation
AssigneeWarner-Lambert Company
InventorsMark Robert Barvian, William Alexander Denny, Ellen Myra Dobrusin, James Marino Hamby, Howard Daniel Hollis Showalter, Andrew Mark Thompson, Roy Thomas Winters, Zhipei Wu
Life of this patent
Estimating the term…
Abstract
This invention relates to the inhibition of protein tyrosine kinase (PTK) and cell cycle kinase mediated cellular proliferation. More specifically, this invention relates to naphthyridinones and their use in inhibiting cellular proliferation and PTK or cell cycle kinase enzymatic activity.
Claims65
A compound having the Formula I ##STR22## wherein -- -- -- is absent or bond;
- R.sup.1 is ##STR23## R.sup.2 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl, or C.sub.5 -C.sub.12 bicycloalkyl;
- each R.sup.3 is independently hydrogen or C.sub.1 -C.sub.6 alkyl;
- each n is independently 0 to 7;
- ##STR24## R.sup.5 is hydrogen, aryl, substituted aryl, heteroaryl, or substituted heteroaryl, and the pharmaceutically accepted salts thereof.
1 more element
The compounds:
- 7-amino-3-(2,6-dichlorophenyl)-1-methyl-1H-[1,6]naphthyridin-2-one;
- 3-(2,6-dichlorophenyl)-1-methyl-7-methylamino-1H-[1,6]naphthyridin-2-one;
- 3-(2,6-dichlorophenyl)-7-dimethylamino-1-methyl-1H-[1,6]naphthyridin-2-one;
- 3-(2,6-dichlorophenyl)-7-[2-(diethylamino)ethylamino]-1-methyl-1H-[1,6]naph thyridin-2-one;
- 3-(2,6-dichlorophenyl)-7-[3-(diethylamino)propylamino]-1-methyl-1H-[1,6]nap hthyridin-2-one;
- 3-(2,6-dichlorophenyl)-7-[4-(diethylamino)butylamino]-1-methyl-1H -[1,6]naphthyridin-2-one;
- 3-(2,6-dichlorophenyl)-7-[5-(diethylamino)pentylamino]-1-methyl-1H -[1,6]naphthyridin-2-one;
- 3-(2,6-dichlorophenyl)-1-methyl-7-[3-(4-methylpiperazin-1-yl)propylamino]-1 H-[1,6]naphthyridin-2-one;
- 3-(2,6-dichlorophenyl)-1-methyl-7-[4-(4-methylpiperazin-1-yl)butylamino]-1H -[1,6]naphthyridin-2-one;
- and
- 3-(2,6-dichlorophenyl)-1-methyl-7-[5-(4-methylpiperazin-1-yl)pentylamino]-1 H -[1,6]naphthyridin-2-one.
8 more elements
The compounds:
- 3-(2,6-dichlorophenyl)-1-methyl-7-[3-(4-morpholino)propylamino]-1H-[1,6]nap hthyridin-2-one;
- 3-(2,6-dichlorophenyl)-7-[3-(imidazol-1-yl)propylamino]-1-methyl-1H-[1,6]na phthyridin-2-one;
- 3-(2,6-dichlorophenyl)-1-methyl-7-(phenylamino)-1H-[1,6]naphthyridin-2-one;
- 3-(2,6-dichlorophenyl)-1-methyl-7-(4-pyridylamino)-1H-[1,6]naphthyridin-2-o ne;
- 3-(2,6-dichlorophenyl)-7-[(4-methoxyphenyl)amino]-1-methyl-1H -[1,6]naphthyridin-2-one;
- 3-(2,6-dichlorophenyl)-7-[(4-(2-(diethylamino)ethoxy)phenyl)amino]-1-methyl -1H-[1,6]naphthyridin-2-one;
- 3-(2,6-dichlorophenyl)-1-methyl-7-[4-(4-morpholino)butylamino]-1H-[1,6]naph thyridin-2-one;
- 3-(2,6-dichlorophenyl)-7-[(4-(3-(diethylamino)propoxy)phenyl)amino]-1-methy l-1H-[1,6]naphthyridin-2-one;
- 3-(2,6-dichlorophenyl)-1-methyl-7-[(4-(2-(4-methylpiperazin-1-yl)ethoxy)phe nyl)amino]-1H-[1,6]naphthyridin-2-one;
- 3-(2,6-dichlorophenyl)-1-methyl-7-[(4-(3-(4-methylpiperazin-1-yl)propoxy)ph enyl)amino]-1H-[1,6]naphthyridin-2-one;
- and
- 3-(2,6-dichlorophenyl)-1-methyl-7-[(4-(4-methylpiperazin-1-yl)phenyl)amino] -1H-[1,6]naphthyridin-2-one.
9 more elements
The compounds:
- 7-Amino-1H-[1,6]naphthyridin-2-one;
- 7-Amino-1-ethyl-1H-[1,6]naphthyridin-2-one;
- 7-Fluoro-1-ethyl-1H-[1,6]naphthyridin-2-one;
- 1-Ethyl-7-phenylamino-1H -[1,6]naphthyridin-2-one;
- 1-Ethyl-7-(4-methoxyphenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Ethyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6]naphthyridin-2-on e;
- 1-Ethyl-7-(4-(morpholin-4-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Ethyl-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- and
- 1-Ethyl-7-phenylamino-3,4-dihydro-1H -[1,6]naphthyridin-2-one.
7 more elements
The compounds:
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-1-ethyl-1H-[1,6]naphthyridin-2-on e;
- 7-[4-(3-(Diethylamino)propoxy)phenylamino]-1-ethyl-1,6-naphthyridin-2-one;
- 1-Ethyl-7-[4-(2-(4-methylpiperazin-1-yl)ethoxy)phenylamino]-1,6-naphthyridi n-2-one;
- 1-Ethyl-7-[4-(3-(4-methylpiperazin-1-yl)propoxy)phenylamino]-1,6-naphthyrid in-2-one;
- 1-Ethyl-7-(4-pyridylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Methyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H -[1,6]naphthyridin-2-one;
- 1-Isopropyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6]naphthyridin- 2-one;
- 1-Isopentyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6]naphthyridin- 2-one;
- 1-Cyclopentyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6]naphthyridi n-2-one;
- and
- 1-Cyclohexyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6]naphthyridin -2-one.
8 more elements
The compounds:
- 1-Cycloheptyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6]naphthyridi n-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6 ]naphthyridin-2-one;
- 1-Methyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino}-1H-[ 1,6]naphthyridin-2-one;
- 1-Ethyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino}-1H-[1 ,6]naphthyridin-2-one;
- 1-Isopropyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino}-1 H-[1,6]naphthyridin-2-one;
- 1-Isopentyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino}-1 H-[1,6]naphthyridin-2-one;
- 1-Cyclopentyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino} -1H-[1,6]naphthyridin-2-one;
- 1-Cyclohexyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino}- 1H-[1,6]naphthyridin-2-one;
- 1-Cycloheptyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino} -1H-[1,6]naphthyridin-2-one;
- and
- 1-Bicyclo[2.2.1]hept-2-yl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl] phenylamino}-1H-[1,6]naphthyridin-2-one.
8 more elements
The compounds:
- 1-Methyl-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino}-1H-[1,6]nap hthyridin-2-one;
- 1-Ethyl-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino}-1H-[1,6]naph thyridin-2-one;
- 7-{4-[4-(3-(Hydroxy)propyl)piperidin-1-yl]phenylamino}-1-isopropyl-1H-[1,6] naphthyridin-2-one;
- 7-{4-[4-(3-(Hydroxy)propyl)piperidin-1-yl]phenylamino}-1-isopentyl-1H-[1,6] naphthyridin-2-one;
- 1-Cyclopentyl-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino}-1H-[1, 6]naphthyridin-2-one;
- 1-Cyclohexyl-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino}-1H-[1,6 ]naphthyridin-2-one;
- 1-Cycloheptyl-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino}-1H-[1, 6]naphthyridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenyla mino}-1H-[1,6]naphthyridin-2-one;
- 1-Methyl-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- and
- 1-Ethyl-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one.
8 more elements
The compounds:
- 1-Isopropyl-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Isopentyl-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Cyclopentyl-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Cyclohexyl-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Cycloheptyl-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyri din-2-one;
- 7-(4-Fluorophenylamino)-1-methyl-1H-[1,6]naphthyridin-2-one;
- 1-Ethyl-7-(4-fluorophenylamino)-1H-[1,6]naphthyridin-2-one;
- 7-(4-Fluorophenylamino)-1-isopropyl-1H-[1,6]naphthyridin-2-one;
- and
- 7-(4-Fluorophenylamino)-1-isopentyl-1H-[1,6]naphthyridin-2-one.
8 more elements
The compounds:
- 1-Cyclopentyl-7-(4-fluorophenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Cyclohexyl-7-fluorophenylamino-1H-[1,6]naphthyridin-2-one;
- 1-Cycloheptyl-7-(4-fluorophenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-7-(4-fluorophenylamino)-1H-[1,6]naphthyridin-2-on e;
- 7-[4-(4-(Hydroxy)piperidin-1-yl)phenylamino]-1-methyl-1H-[1,6]naphthyridin- 2-one;
- 1-Ethyl-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-1H-[1,6]naphthyridin-2 -one;
- 7-[4-(4-(Hydroxy)piperidin-1-yl)phenylamino]-1-isopropyl-1H-[1,6]naphthyrid in-2-one;
- 7-[4-(4-(Hydroxy)piperidin-1-yl)phenylamino]-1-isopentyl-1H-[1,6]naphthyrid in-2-one;
- 1-Cyclopentyl-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-1H-[1,6]naphthyr idin-2-one;
- and
- 1-Cyclohexyl-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-1H-[1,6]naphthyri din-2-one.
8 more elements
The compounds:
- 1-Cycloheptyl-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-1H-[1,6]naphthyr idin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-1H-[ 1,6]naphthyridin-2-one;
- 7-[4-(3-(Hydroxymethyl)piperidin-1-yl)phenylamino]-1-methyl-1H-[1,6]naphthy ridin-2-one;
- 1-Ethyl-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-1H-[1,6]naphthyr idin-2-one;
- 7-[4-(3-(Hydroxymethyl)piperidin-1-yl)phenylamino]-1-isopropyl-1H-[1,6]naph thyridin-2-one;
- 7-[4-(3-(Hydroxymethyl)piperidin-1-yl)phenylamino]-1-isopentyl-1H-[1,6]naph thyridin-2-one;
- 1-Cyclopentyl-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-1H-[1,6]na phthyridin-2-one;
- 1-Cyclohexyl-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-1H-[1,6]nap hthyridin-2-one;
- 1-Cycloheptyl-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-1H-[1,6]na phthyridin-2-one;
- and p1 1-Bicyclo[2.2.1]hept-2-yl-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamin o]-1H-[1,6]naphthyridin-2-one.
7 more elements
The compounds:
- 1-Methyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyridin-2-one;
- 1-Ethyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyridin-2-one;
- 1-Isopropyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyridin-2-one;
- 1-Isopentyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyridin-2-one;
- 1-Cyclopentyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyridin-2-on e;
- 1-Cyclohexyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyridin-2-one
- 1-Cycloheptyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyridin-2-on e;
- 1-Bicyclo[2.2.1]hept-2-yl-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]napht hyridin-2-one;
- 1-Methyl-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- and
- 1-Isopropyl-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one.
8 more elements
The compounds:
- 1-Isopentyl-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Cyclopentyl-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Cyclohexyl-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Cycloheptyl-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthy ridin-2-one;
- 1-Methyl-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Ethyl-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Isopropyl-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Isopentyl-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- and
- 1-Cyclopentyl-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one .
8 more elements
The compounds:
- 1-Cyclohexyl-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Cycloheptyl-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one ;
- 1-Bicyclo[2.2.1]hept-2-yl-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphth yridin-2-one;
- 1-Methyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4-dihydro-1H-[1,6]naph thyridin-2-one;
- 1-Ethyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4-dihydro-1H-[1,6]napht hyridin-2-one;
- 1-Isopropyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4-dihydro-1H-[1,6]n aphthyridin-2-one;
- 1-Isopentyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4-dihydro-1H-[1,6]n aphthyridin-2-one;
- 1-Cyclopentyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4dihydro-1H-[1,6] naphthyridin-2-one;
- 1-Cyclohexyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4-dihydro-1H-[1,6] naphthyridin-2-one;
- and
- 1-Cycloheptyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4-dihydro-1H-[1,6 ]naphthyridin-2-one.
8 more elements
The compounds:
- 1-Bicyclo[2.2.1]hept-2-yl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4-dih ydro-1H-[1,6]naphthyridin-2-one;
- 1-Methyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]-phenylamino}-3,4 -dihydro-1H-[1,6]naphthyridin-2-one;
- 1-Ethyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino}-3,4-d ihydro-1H-[1,6]naphthyridin-2-one;
- 1-Isopropyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino}-3 ,4-dihydro-1H-[1,6]naphthyridin-2-one;
- 1-Isopentyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino}-3 ,4-dihydro-1H-[1,6]naphthyridin-2-one;
- 1-Cyclopentyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino} -3,4-dihydro-1H-[1,6]naphthyridin-2-one;
- 1-Cyclohexyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino}- 3,4-dihydro-1H-[1,6]naphthyridin-2-one;
- 1-Cycloheptyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino} -3,4-dihydro-1H-[1,6]naphthyridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl] phenylamino}-3,4-dihydro-1H-[1,6]naphthyridin-2-one;
- and
- 1-Methyl-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino}-3,4-dihydro -1H-[1,6]naphthyridin-2-one.
8 more elements
The compounds:
- 1-Ethyl-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino}-3,4-dihydro- 1H-[1,6]naphthyridin-2-one;
- 7-{4-[4-(3-(Hydroxy)propyl)piperidin-1-yl]phenylamino}-1-isopropyl-3,4-dihy dro-1H-[1,6]naphthyridin-2-one;
- 7-{4-[4-(3-(Hydroxy)propyl)piperidin-1-yl]phenylamino}-1-isopentyl-3,4-dihy dro-1H-[1,6]naphthyridin-2-one;
- 1-Cyclopentyl-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino}-3,4-di hydro-1H-[1,6]naphthyridin-2-one;
- 1-Cyclohexyl-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino}-3,4-dih ydro-1H-[1,6]naphthyridin-2-one;
- 1-Cycloheptyl-7-{4-[4-(3-hydroxy)propyl)piperidin-1-yl]phenylamino}-3,4-dih ydro-1H-[1,6]naphthyridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenyla mino}-3,4-dihydro-1H-[1,6]naphthyridin-2-one;
- 1-Methyl-7-(4-(pyrazol-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyridin-2 -one;
- 1-Ethyl-7-(4-(pyrazol-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyridin-2- one;
- and
- 1-Isopropyl-7-(4-(pyrazol-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyridi n-2-one.
8 more elements
The compounds:
- 1-Isopentyl-7-(4-(pyrazol-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyridi n-2-one;
- 1-Cyclopentyl-7-(4-(pyrazol-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyri din-2-one;
- 1-Cyclohexyl-7-(4-(pyrazol-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyrid in-2-one;
- 1-Cycloheptyl-7-(4-(pyrazol-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyri din-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-7-(4-(pyrazol-1-yl)phenylamino)-3,4-dihydro-1H-[1 ,6]naphthyridin-2-one;
- 7-(4-Fluorophenylamino)-1-methyl-3,4-dihydro-1H-[1,6]naphthyridin-2-one;
- 1-Ethyl-7-(4-fluorophenylamino)-3,4-dihydro-1H-[1,6]naphthyridin-2-one;
- 7-(4-Fluorophenylamino)-1-isopropyl-3,4-dihydro-1H-[1,6]naphthyridin-2-one;
- 7-(4-Fluorophenylamino)-1-isopentyl-3,4-dihydro-1H-[1,6]naphthyridin-2-one;
- and
- 1-Cyclopentyl-7-(4-fluorophenylamino)-3,4-dihydro-1H-[1,6]naphthyridin-2-on e.
8 more elements
The compounds:
- 1-Cyclohexyl-7-(4-fluorophenylamino)-3,4-dihydro-1H-[1,6]naphthyridin-2-one ;
- 1-Cycloheptyl-7-(4-fluorophenylamino)-3,4-dihydro-1H-[1,6]naphthyridin-2-on e;
- 1- Bicyclo[2.2.1]hept-2-yl-7-(4-fluorophenylamino)-3,4-dihydro-1H-[1,6]naphth yridin-2-one;
- 7-[4-(4-(Hydroxy)piperidin-1-yl)phenylamino]-1-methyl-3,4-dihydro-1H-[1,6]n aphthyridin-2-one;
- 1-Ethyl-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-3,4-dihydro-1H-[1,6]na phthyridin-2-one;
- 7-[4-(4-(Hydroxy)piperidin-1-yl)phenylamino]-1-isopropyl-3,4-dihydro-1H-[1, 6]naphthyridin-2-one;
- 7-[4-(4-(Hydroxy)piperidin-1-yl)phenylamino]-1-isopentyl-3,4-dihydro-1H-[1, 6]naphthyridin-2-one;
- 1-Cyclopentyl-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-3,4-dihydro-1H-[ 1,6]naphthyridin-2-one;
- 1-Cyclohexyl-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-3,4-dihydro-1H-[1 ,6]naphthyridin-2-one;
- and
- 1-Cycloheptyl-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-3,4dihydro-1H-[1 ,6]naphthyridin-2-one.
8 more elements
The compounds:
- 1-Bicyclo[2.2.1]hept-2-yl-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-3,4- dihydro-1H-[1,6]naphthyridin-2-one;
- 7-[4-(3-(Hydroxymethyl)piperidin-1-yl)phenylamino]-1-methyl-3,4-dihydro-1H- [1,6]naphthyridin-2-one;
- 1-Ethyl-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-3,4-dihydro-1H-[ 1,6]naphthyridin-2-one;
- 7-[4-(3-(Hydroxymethyl)piperidin-1-yl)phenylamino]-1-isopropyl-3,4-dihydro- 1H-[1,6]naphthyridin-2-one;
- 7-[4-(3-(Hydroxymethyl)piperidin-1-yl)phenylamino]-1-isopentyl-3,4-dihydro- 1H-[1,6]naphthyridin-2-one;
- 1-Cyclopentyl-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-3,4-dihydr o-1H-[1,6]naphthyridin-2-one;
- 1-Cyclohexyl-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-3,4-dihydro -1H-[1,6]naphthyridin-2-one;
- 1-Cycloheptyl-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-3,4-dihydr o-1H-[1,6]naphthyridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino ]-3,4-dihydro-1H-[1,6]naphthyridin-2-one;
- and
- 1-Methyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-3,4-dihydro-1H-[1,6]naphthyrid in-2-one.
8 more elements
The compounds:
- 1-Ethyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-3,4-dihydro-1H-[1,6]naphthyridi n-2-one;
- 1-Isopropyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-3,4-dihydro-1H-[1,6]naphthy ridin-2-one;
- 1-Isopentyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-3,4-dihydro-1H-[1,6]naphthy ridin-2-one;
- 1-Cyclopentyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-3,4-dihydro-1H-[1,6]napht hyridin-2-one;
- 1-Cyclohexyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-3,4dihydro-1H-[1,6]naphthy ridin-2-one;
- 1-Cycloheptyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-3,4-dihydro-1H-[1,6]napht hyridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-7-[4-(2H-tetrazol-5-yl)phenylamino]-3,4-dihydro-1 H-[1,6]naphthyridin-2-one;
- 1-Methyl-7-(4-(piperidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyridin -2-one;
- 1-Ethyl-7-(4-(piperidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyridin- 2-one;
- and
- 1-Isopropyl-7-(4-(piperidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyri din-2-one.
8 more elements
The compounds:
- 1-Isopentyl-7-(4-(piperidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyri din-2-one;
- 1-Cyclopentyl-7-(4-(piperidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthy ridin-2-one;
- 1-Cyclohexyl-7-(4-(piperidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyr idin-2-one;
- 1-Cycloheptyl-7-(4-(piperidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthy ridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-7-(4-(piperidin-1-yl)phenylamino)-3,4-dihydro-1H- [1,6]naphthyridin-2-one;
- 1-Methyl-7-(4-(pyrrolidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyridi n-2-one;
- 1-Ethyl-7-(4-(pyrrolidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyridin -2-one;
- 1-Isopropyl-7-(4-(pyrrolidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyr idin-2-one;
- 1-Isopentyl-7-(4-pyrrolidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthyri din-2-one;
- and
- 1-Cyclopentyl-7-(4-(pyrrolidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphth yridin-2-one.
8 more elements
The compounds:
- 1-Cyclohexyl-7-(4-(pyrrolidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphthy ridin-2-one;
- 1-Cycloheptyl-7-(4-(pyrrolidin-1-yl)phenylamino)-3,4-dihydro-1H-[1,6]naphth yridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-7-(4-(pyrrolidin-1-yl)phenylamino)-3,4-dihydro-1H -[1,6]naphthyridin-2-one;
- 3-Fluoro-1-methyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6]naphthy ridin-2-one;
- 1-Ethyl-3-fluoro-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6]naphthyr idin-2-one;
- 3-Fluoro-1-isopropyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6]naph thyridin-2-one;
- 3-Fluoro-1-isopentyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6]naph thyridin-2-one;
- 1-Cyclopentyl-3-fluoro-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6]na phthyridin-2-one;
- 1-Cyclohexyl-3-fluoro-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6]nap hthyridin-2-one;
- and
- 1-Cycloheptyl-3-fluoro-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H-[1,6]na phthyridin-2-one.
8 more elements
The compounds:
- 1-Bicyclo[2.2.1]hept-2-yl-3-fluoro-7-[4-(4-methylpiperazin-1-yl)phenylamino ]-1H-[1,6]naphthyridin-2-one;
- 3-Fluoro-1-methyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylam ino}-1H-[1,6]naphthyridin-2-one;
- 1-Ethyl-3-fluoro-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylami no}-1H-[1,6]naphthyridin-2-one;
- 3-Fluoro-1-isopropyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]pheny lamino}-1H-[1,6]naphthyridin-2-one;
- 3-Fluoro-1-isopentyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]pheny lamino}-1H-[1,6]naphthyridin-2-one;
- 1-Cyclopentyl-3-fluoro-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phe nylamino}-1H-[1,6]naphthyridin-2-one;
- 1-Cyclohexyl-3-fluoro-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phen ylamino}-1H-[1,6]naphthyridin-2-one;
- 1-Cycloheptyl-3-fluoro-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phe nylamino}-1H-[1,6]naphthyridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-3-fluoro-7-{4-[4-(3-(morpholin-4-yl)propyl)piperi din-1-yl]phenylamino}-1H-[1,6]naphthyridin-2-one;
- and
- 3-Fluoro-1-methyl-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino}-1H -[1,6]naphthyridin-2-one.
8 more elements
The compounds:
- 1-Ethyl-3-fluoro-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino}-1H- [1,6]naphthyridin-2-one;
- 3-Fluoro-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino}-1-isopropyl -1H-[1,6]naphthyridin-2-one;
- 3-Fluoro-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino}-1-isopentyl -1H-[1,6]naphthyridin-2-one;
- 1-Cyclopentyl-3-fluoro-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamin o}-1H-[1,6]naphthyridin-2-one;
- 1-Cyclohexyl-3-fluoro-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamino }-1H-[1,6]naphthyridin-2-one;
- 1-Cycloheptyl-3-fluoro-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-yl]phenylamin o}-1H-[1,6]naphthyridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-3-fluoro-7-{4-[4-(3-(hydroxy)propyl)piperidin-1-y l]phenylamino}-1H-[1,6]naphthyridin-2-one;
- 3-Fluoro-1-methyl-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-on e;
- 1-Ethyl-3-fluoro-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-one ;
- and
- 3-Fluoro-1-isopropyl-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyridin-2 -one.
8 more elements
The compounds:
- 3-Fluoro-1-isopentyl-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyridin-2 -one;
- 1-Cyclopentyl-3-fluoro-7-(4-(pyrazol-1-yl)phenylamino-1H-[1,6]naphthyridin- 2-one;
- 1-Cyclohexyl-3-fluoro-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyridin- 2-one;
- 1-Cycloheptyl-3-fluoro-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6]naphthyridin -2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-3-fluoro-7-(4-(pyrazol-1-yl)phenylamino)-1H-[1,6] naphthyridin-2-one;
- 3-Fluoro-7-(4-fluorophenylamino)-1-methyl-1H-[1,6]naphthyridin-2-one;
- 1-Ethyl-3-fluoro-7-(4-fluorophenylamino)-1H-[1,6]naphthyridin-2-one;
- 3-Fluoro-7-(4-fluorophenylamino)-1-isopropyl-1H-[1,6]naphthyridin-2-one;
- 3-Fluoro-7-(4-fluorophenylamino)-1-isopentyl-1H-[1,6]naphthyridin-2-one;
- and
- 1-Cyclopentyl-3-fluoro-7-(4-fluorophenylamino-1H-[1,6]naphthyridin-2-one.
8 more elements
The compounds:
- 1-Cyclohexyl-3-fluoro-7-(4-fluorophenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Cycloheptyl-3-fluoro-7-(4-fluorophenylamino)-1H-[1,6]naphthyridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-3-fluoro-7-(4-fluorophenylamino)-1H-[1,6]naphthyr idin-2-one;
- 3-Fluoro-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-1-methyl-1H-[1,6]naph thyridin-2-one;
- 1-Ethyl-3-fluoro-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-1H-[1,6]napht hyridin-2-one;
- 3-Fluoro-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-1-isopropyl-1H-[1,6]n aphthyridin-2-one;
- 3-Fluoro-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-1-isopentyl-1H-[1,6]n aphthyridin-2-one;
- 1-Cyclopentyl-3-fluoro-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-1H-[1,6 ]naphthyridin-2-one;
- 1-Cyclohexyl-3-fluoro-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-1H-[1,6] naphthyridin-2-one;
- and
- 1-Cycloheptyl-3-fluoro-7-[4-(4-(hydroxy)piperidin-1-yl)phenylamino]-1H-[1,6 ]naphthyridin-2-one.
8 more elements
The compounds:
- 1-Bicyclo[2.2.1]hept-2-yl-3-fluoro-7-[4-(4-(hydroxy)piperidin-1-yl)phenylam ino]-1H-[1,6]naphthyridin-2-one;
- 3-Fluoro-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-1-methyl-1H-[1, 6]naphthyridin-2-one;
- 1-Ethyl-3-fluoro-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-1H-[1,6 ]naphthyridin-2-one;
- 3-Fluoro-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-1-isopropyl-1H- [1,6]naphthyridin-2-one;
- 3-Fluoro-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-1-isopentyl-1H- [1,6]naphthyridin-2-one;
- 1-Cyclopentyl-3-fluoro-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-1 H-[1,6]naphthyridin-2-one;
- 1-Cyclohexyl-3-fluoro-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-1H -[1,6]naphthyridin-2-one;
- 1-Cycloheptyl-3-fluoro-7-[4-(3-(hydroxymethyl)piperidin-1-yl)phenylamino]-1 H-[1,6]naphthyridin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-3-fluoro-7-[4-(3-(hydroxymethyl)piperidin-1-yl)ph enylamino]-1H-[1,6]naphthyridin-2-one;
- and
- 3-Fluoro-1-methyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyridin- 2-one.
8 more elements
The compounds:
- 1-Ethyl-3-fluoro-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyridin-2 -one;
- 3-Fluoro-1-isopropyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyrid in-2-one;
- 3-Fluoro-1-isopentyl-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyrid in-2-one;
- 1-Cyclopentyl-3-fluoro-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyr idin-2-one;
- 1-Cyclohexyl-3-fluoro-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyri din-2-one;
- 1-Cycloheptyl-3-fluoro-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[1,6]naphthyr idin-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-3-fluoro-7-[4-(2H-tetrazol-5-yl)phenylamino]-1H-[ 1,6]naphthyridin-2-one;
- 3-Fluoro-1-methyl-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2- one;
- 1-Ethyl-3-fluoro-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2-o ne;
- and
- 3-Fluoro-1-isopropyl-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyridin -2-one.
8 more elements
The compounds:
- 3-Fluoro-1-isopentyl-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyridin -2-one;
- 1-Cyclopentyl-3-fluoro-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyrid in-2-one;
- 1-Cyclohexyl-3-fluoro-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyridi n-2-one;
- 1-Cycloheptyl-3-fluoro-7-(4-(piperidin-1-yl)phenylamino)-1H-[1,6]naphthyrid in-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-3-fluoro-7-(4-(piperidin-1-yl)phenylamino)-1H-[1, 6]naphthyridin-2-one;
- 3-Fluoro-1-methyl-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2 -one;
- 1-Ethyl-3-fluoro-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyridin-2- one;
- 3-Fluoro-1-isopropyl-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyridi n-2-one;
- 3-Fluoro-1-isopentyl-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyridi n-2-one;
- and
- 1-Cyclopentyl-3-fluoro-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyri din-2-one.
8 more elements
The compounds:
- 1-Cyclohexyl-3-fluoro-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyrid in-2-one;
- 1-Cycloheptyl-3-fluoro-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1,6]naphthyri din-2-one;
- 1-Bicyclo[2.2.1]hept-2-yl-3-fluoro-7-(4-(pyrrolidin-1-yl)phenylamino)-1H-[1 ,6]naphthyridin-2-one;
- 3-(2,6-Dichlorophenyl)-7-(4-fluoro-3-methylphenylamino)-1-methyl-1H-[1,6]na phthyridin-2-one;
- 3-(2,6-Dichlorophenyl)-7-(4-ethoxyphenylamino)-1-methyl-1H-[1,6]naphthyridi n-2-one;
- 3-(2,6-Dichlorophenyl)-7-(3-(hydroxymethyl)phenylamino)-1-methyl-1H-[1,6]na phthyridin-2-one;
- 3-(2,6-Dichlorophenyl)-1-methyl-7-(4-(morpholin-4-yl)phenylamino)-1H-[1,6]n aphthyridin-2-one;
- 3-(2,6-Dichlorophenyl)-1-methyl-7-[4-(2-(morpholin-4-yl)ethoxy)phenylamino] -1H-[1,6]naphthyridin-2-one;
- 3-(2,6-Dichlorophenyl)-1-methyl-7-[4-(2-(piperidin-1-yl)ethoxy)phenylamino] -1H-[1,6]naphthyridin-2-one;
- and
- 3-(2,6-Dichlorophenyl)-1-methyl-7-[4-(4-(methylpiperazin-1-yl)methyl)phenyl amino]-1H-[1,6]naphthyridin-2-one.
8 more elements
The compounds:
- 3-(2,6-Dichlorophenyl)-7-[4-(2-(dimethylamino)ethoxy)phenylamino]-1-methyl- 1H-[1,6]naphthyridin-2-one;
- 3-[3-(2,6-Dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-7-yl amino]-benzoic acid;
- 3-(2,6-Dichlorophenyl)-7-[3-(2-(diethylamino)ethoxy)phenylamino]-1-methyl-1 H-[1,6]naphthyridin-2-one;
- N-(2-{4-[3-(2,6-Dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-[1,6]naphthyridi n-7-ylamino]phenoxy}ethyl)-N-ethyl-acetamide;
- {4-[3-(2,6-Dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-7-y lamino]phenyl}-acetic acid;
- and
- 3-(2,6-Dichlorophenyl)-1-ethyl-7-(4-fluoro-3-methylphenylamino)-1H-[1,6]nap hthyridin-2-one.
4 more elements
The compounds:
- 3-(2,6-Dichlorophenyl)-7-(4-ethoxyphenylamino)-1-ethyl-1H-[1,6]naphthyridin -2-one;
- 3-(2,6-Dichlorophenyl)-1-ethyl-7-(3-(hydroxymethyl)phenylamino)-1H-[1,6]nap hthyridin-2-one;
- 3-(2,6-Dichlorophenyl)-1-ethyl-7-(4-(morpholin-4-yl)phenylamino)-1H-[1,6]na phthyridin-2-one;
- 3-(2,6-Dichlorophenyl)-7-[4-(2-(diethylamino)ethoxy)phenylamino]-1-ethyl-1H -[1,6]naphthyridin-2-one;
- 3-(2,6-Dichlorophenyl)-1-ethyl-7-[4-(2-(morpholin-4-yl)ethoxy)phenylamino]- 1H-[1,6]naphthyridin-2-one;
- 3-(2,6-Dichlorophenyl)-1-ethyl-7-[4-(2-(piperidin-1-yl)ethoxy)phenylamino]- 1H-[1,6]naphthyridin-2-one;
- 3-(2,6-Dichlorophenyl)-1-ethyl-7-[4-(4-(methylpiperazin-1-yl)methyl)phenyla mino]-1H-[1,6]naphthyridin-2-one;
- 3-(2,6-Dichlorophenyl)-7-[4-(2-(dimethylamino)ethoxy)phenylamino]-1-ethyl-1 H-[1,6]naphthyridin-2-one;
- 3-[3-(2,6-Dichlorophenyl)-1-ethyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-7-yla mino]-benzoic acid;
- 3-(2,6-Dichlorophenyl)-7-[3-(2-(diethylamino)ethoxy)phenylamino]-1-ethyl-1H -[1,6]naphthyridin-2-one;
- N-(2-{4-[3-(2,6-Dichlorophenyl)-1-ethyl-2-oxo-1,2-dihydro-[1,6]naphthyridin -7-ylamino]phenoxy}ethyl)-N-ethyl-acetamide;
- 3-(2,6-Dichlorophenyl)-1-ethyl-7-(4-pyridylamino)-1H-[1,6]naphthyridin-2-on e;
- 3-(2,6-Dichlorophenyl)-1-ethyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-1H -[1,6]naphthyridin-2-one;
- and
- {4-[3-(2,6-Dichlorophenyl)-1-ethyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-7-yl amino]phenyl}-acetic acid.
12 more elements
The compounds:
- 3-(3,5-Dimethoxyphenyl)-1-methyl-7-[3-(4-methylpiperazin-1-yl)propylamino]- 1H-[1,6]naphthyridin-2-one;
- 3-(3,5-Dimethoxyphenyl)-1-ethyl-7-[3-(4-methylpiperazin-1-yl)propylamino]-1 H-[1,6]naphthyridin-2-one;
- 7-(4-(Diethylamino)butylamino)-3-(3,5-dimethoxyphenyl)-1-methyl-1H-[1,6]nap hthyridin-2-one;
- 7-(4-(Diethylamino)butylamino)-3-(3,5-dimethoxyphenyl)-1-ethyl-1H-[1,6]naph thyridin-2-one;
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-3-(3,5-dimethoxyphenyl)-1-ethyl-1 H-[1,6]naphthyridin-2-one;
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-3-(3,5-dimethoxyphenyl)-1-methyl- 1H-[1,6]naphthyridin-2-one;
- 3-(3,5-Dimethoxyphenyl)-1-ethyl-7-(4-pyridylamino)-1H-[1,6]naphthyridin-2-o ne;
- 3-(3,5-Dimethoxyphenyl)-1-methyl-7-(4-pyridylamino)-1H-[1,6]naphthyridin-2- one;
- 3-(2,6-Dichloro-3,5-dimethoxyphenyl)-1-methyl-7-[3-(4-methylpiperazin-1-yl) propylamino]-1H-[1,6]naphthyridin-2-one;
- and
- 3-(2-Chloro-3,5-dimethoxyphenyl)-1-methyl-7-[3-(4-methylpiperazin-1-yl)prop ylamino]-1H-[1,6]naphthyridin-2-one.
8 more elements
The compounds:
- 3-(2,6-Dimethyl-3,5-dimethoxyphenyl)-1-methyl-7-[3-(4-methylpiperazin-1-yl) propylamino]-1H-[1,6]naphthyridin-2-one;
- 1-Methyl-3-(2-methyl-3,5-dimethoxyphenyl)-7-[3-(4-methylpiperazin-1-yl)prop ylamino]-1H-[1,6]naphthyridin-2-one;
- 3-(2,6-Dichloro-3,5-dimethoxyphenyl)-1-ethyl-7-[3-(4-methylpiperazin-1-yl)p ropylamino]-1H-[1,6]naphthyridin-2-one;
- 3-(2-Chloro-3,5-dimethoxyphenyl)-1-ethyl-7-[3-(4-methylpiperazin-1-yl)propy lamino]-1H-[1,6]naphthyridin-2-one;
- 3-(2,6-Dimethyl-3,5-dimethoxyphenyl)-1-ethyl-7-[3-(4-methylpiperazin-1-yl)p ropylamino]-1H-[1,6]naphthyridin-2-one;
- 1-Ethyl-3-(2-methyl-3,5-dimethoxyphenyl)-7-[3-(4-methylpiperazin-1-yl)propy lamino]-1H-[1,6]naphthyridin-2-one;
- 3-(2,6-Dichloro-3,5-dimethoxyphenyl)-7-(4-(diethylamino)butylamino)-1-methy l-1H-[1,6]naphthyridin-2-one;
- 3-(2-Chloro-3,5-dimethoxyphenyl)-7-(4-(diethylamino)butylamino)-1-methyl-1H -[1,6]naphthyridin-2-one;
- 7-(4-(Diethylamino)butylamino)-1-methyl-3-(2-methyl-3,5-dimethoxyphenyl)-1H -[1,6]naphthyridin-2-one;
- and
- 3-(2,6-Dimethyl-3,5-dimethoxyphenyl)-7-(4-(diethylamino)butylamino)-1-methy l-1H-[1,6]naphthyridin-2-one.
8 more elements
The compounds:
- 3-(2,6-Dichloro-3,5-dimethoxyphenyl)-7-(4-(diethylamino)butylamino)-1-ethyl -1H-[1,6]naphthyridin-2-one;
- 3-(2-Chloro-3,5-dimethoxyphenyl)-7-(4-(diethylamino)butylamino)-1-ethyl-1H- [1,6]naphthyridin-2-one;
- 7-(4-(Diethylamino)butylamino)-1-ethyl-3-(2-methyl-3,5-dimethoxyphenyl)-1H- [1,6]naphthyrdin-2-one;
- 7-(4-(Diethylamino)butylamino)-3-(2,6-dimethyl-3,5-dimethoxyphenyl)-1-ethyl -1H-[1,6]naphthyridin-2-one;
- 3-(2,6-Dichloro-3,5-dimethoxyphenyl)-7-[4-(2-(diethylamino)ethoxy)phenylami no]-1-methyl-1H-[1,6]naphthyridin-2-one;
- 3-(2-Chloro-3,5-dimethoxyphenyl)-7-[4-(2-(diethylamino)ethoxy)phenylamino]- 1-methyl-1H-[1,6]naphthyridin-2-one;
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-1-methyl-3-(2-methyl-3,5-dimethox yphenyl)-1H-[1,6]naphthyridin-2-one;
- 3-(2,6-Dimethyl-3,5-dimethoxyphenyl)-7-[4-(2-(diethylamino)ethoxy)phenylami no]-1-methyl-1H-[1,6]naphthyridin-2-one;
- 3-(2,6-Dichloro-3,5-dimethoxyphenyl)-7-[4-(2-(diethylamino)ethoxy)phenylami no]-1-ethyl-1H-[1,6]naphthyridin-2-one;
- and
- 3-(2-Chloro-3,5-dimethoxyphenyl)-7-[4-(2-(diethylamino)ethoxy)phenylamino]- 1-ethyl-1H-[1,6]naphthyridin-2-one.
8 more elements
The compounds:
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-1-ethyl-3-(2-methyl-3,5-dimethoxy phenyl)-1H-[1,6]naphthyridin-2-one;
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-3-(2,6-dimethyl-3,5-dimethoxyphen yl)-1-ethyl-1H-[1,6]naphthyridin-2-one;
- 1-Methyl-7-[3-(4-methylpiperazin-1-yl)propylamino]-3-(2,3,5,6-tetramethylph enyl)-1H-[1,6]naphthyridin-2-one;
- 1-Ethyl-7-[3-(4-methylpiperazin-1-yl)propylamino]-3-(2,3,5,6-tetramethylphe nyl)-1H-[1,6]naphthyridin-2-one;
- 7-(4-(Diethylamino)butylamino)-1-methyl-3-(2,3,5,6-tetramethylphenyl)-1H-[1 ,6]naphthyridin-2-one;
- 7-(4-(Diethylamino)butylamino)-1-ethyl-3-(2,3,5,6-tetramethylphenyl)-1H-[1, 6]naphthyridin-2-one;
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-1-ethyl-3-(2,3,5,6-tetramethylphe nyl)-1H-[1,6]naphthyridin-2-one;
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-1-methyl-3-(2,3,5,6-tetramethylph enyl)-1H-[1,6]naphthyridin-2-one;
- 1-Methyl-7-[3-(4-methylpiperazin-1-yl)propylamino]-3-phenyl-1H-[1,6]naphthy ridin-2-one;
- and
- 1-Ethyl-7-[3-(4-methylpiperazin-1-yl)propylamino]-3-phenyl-1H-[1,6]naphthyr idin-2-one.
8 more elements
The compounds:
- 7-(4-(Diethylamino)butylamino)-1-methyl-3-phenyl-1H-[1,6]naphthyridin-2-one ;
- 7-(4-(Diethylamino)butylamino)-1-ethyl-3-phenyl-1H-[1,6]naphthyridin-2-one;
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-1-ethyl-3-phenyl-1H-[1,6]naphthyr idin-2-one;
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-1-methyl-3-phenyl-1H-[1,6]naphthy ridin-2-one;
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-1-methyl-3-(thiophen-3-yl)-1H-[1, 6]naphthyridin-2-one;
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-1-ethyl-3-(thiophen-3-yl)-1H-[1,6 ]naphthyridin-2-one;
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-1-methyl-3-(thiophen-2-yl)-1H-[1, 6]naphthyridin-2-one;
- and
- 7-[4-(2-(Diethylamino)ethoxy)phenylamino]-1-ethyl-3-(thiophen-2-yl)-1H-[1,6 ]naphthyridin-2-one.
6 more elements
A compound having the Formula I wherein
- -- -- -- is a bond or absent;
- R.sup.1 is
- --NH.sub.2,
- --F,
- --NH-phenyl,
- --NH-substituted phenyl, ##STR32## R.sup.2 is --CH.sub.3, --CH.sub.2 CH.sub.3, hydrogen, ##STR33## R.sup.5 is hydrogen ##STR34## fluorine, ##STR35## the pharmaceutically acceptable salts thereof.
3 more elements
Dependencies are inferred from the claim text.