US2014256713A1PendingUtilityA1
2-oxonaphthyridine-3-carboxamides hiv integrase inhibitors
Est. expiryFeb 11, 2024(expired)· nominal 20-yr term from priority
Inventors:Brian Alvin JohnsEric Eugene BorosTakashi KawasujiCecilia S. KobleNoriyuki KuroseHitoshi MuraiRonald George SherrillJason Gordon Weatherhead
A61P 31/12C07D 471/04A61P 31/18
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Abstract
The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.
Claims
exact text as granted — not AI-modified1 - 32 . (canceled)
33 . A compound selected from the group consisting of:
7-benzyl-N-(cyclopropylmethyl)-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-4-hydroxy-1-[4-(methylsulfonyl)benzyl]-2-oxo-N-(pyridin-4-ylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-N,4-dihydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 4-Hydroxy-N-(2-methylpropyl)-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-Cycloheptyl-4-hydroxy-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-Cyclopentyl-4-hydroxy-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-Cyclobutyl-4-hydroxy-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 4-Hydroxy-2-oxo-N-(2-phenylethyl)-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 4-Hydroxy-2-oxo-N-(1-phenylethyl)-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-(Cyclohexylmethyl)-4-hydroxy-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-(2-Furanylmethyl)-4-hydroxy-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-Cyclohexyl-4-hydroxy-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 4-Hydroxy-2-oxo-7-(phenylmethyl)-N-(2-thienylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-Cyclopropyl-4-hydroxy-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-Cyclobutyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-Cyclopropyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-N-(2-furanylmethyl)-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[2-(1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; (±)-7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-N-(tetrahydro-2-furnylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[2-(1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-N-(4-pyridinylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-N-(2-pyridinylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-N-(3-pyridinylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-N-(hexahydro-1H-azepin-1-yl)-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(5-Fluoro-2-pyridinyl)methyl]-4-hydroxy-N-[3-(4-morpholinyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[2-(2-pyridinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-N-[2-(1H-imidazol-4-yl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; Benzyl-N-cyclobutyl-4-hydroxy-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-N-cyclopropyl-4-hydroxy-1-[4-(methylsulfonyl)benzyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-N-cyclobutyl-4-hydroxy-1-[4-(methylsulfonyl)benzyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-N-(2-furylmethyl)-4-hydroxy-1-[4-(methylsulfonyl)benzyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-N-cyclopropyl-4-hydroxy-1-[(1-methyl-1H-imidazol-2-yl)methyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-Fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-4-hydroxy-N-(2-methoxyethyl)-1-[(1-methyl-1H-imidazol-2-yl)methyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-4-hydroxy-1-(2-morpholin-4-yl-2-oxoethyl)-2-oxo-N-(pyridin-4-ylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-Fluorobenzyl)-4-hydroxy-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-N-(pyridin-4-ylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-1-(cyclopropylmethyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-N-cyclobutyl-1-(cyclopropylmethyl)-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-N-cyclobutyl-4-hydroxy-1-(2-morpholin-4-ylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-4-hydroxy-1-[4-(methylsulfonyl)benzyl]-N-(3-morpholin-4-ylpropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-4-hydroxy-1-[4-(methylsulfonyl)benzyl]-2-oxo-N-(2-pyrrolidin-1-ylethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-N-cyclobutyl-4-hydroxy-2-oxo-1-(1,3-thiazol-2-ylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-Fluorobenzyl)-4-hydroxy-1-[4-(methylsulfonyl)benzyl]-2-oxo-N-(pyridin-4-ylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-Fluorobenzyl)-4-hydroxy-1-[4-(methylsulfonyl)benzyl]-2-oxo-N-(pyridin-3-ylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-Fluorobenzyl)-4-hydroxy-1-[4-(methylsulfonyl)benzyl]-N-(2-morpholin-4-ylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-(2-Furanylmethyl)-4-hydroxy-1-[(4-nitrophenyl)methyl]-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 4-Hydroxy-N-[2-(methyloxy)ethyl]-1-[(4-nitrophenyl)methyl]-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-Cyclobutyl-4-hydroxy-1-[(4-nitrophenyl)methyl]-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[(4-Aminophenyl)methyl]-N-cyclobutyl-4-hydroxy-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; and pharmaceutically acceptable salts thereof.
34 . A compound selected from the group consisting of:
7-(4-fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-Cyclopropyl-7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-4-hydroxy-N-(2-methoxyethyl)-1-(2-morpholin-4-yl-2-oxoethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 4-Hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-4-hydroxy-N-(2-methoxyethyl)-1-[4-(methylsulfonyl)benzyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-Fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-Benzyl-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1-(1,3-thiazol-2-ylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-Fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-1-[4-(methylsulfonyl)benzyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; and pharmaceutically acceptable salts thereof.
35 . A compound selected from the group consisting of:
7-[(4-Fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide sodium salt; Sodium 1-[2-(Dimethylamino)-2-oxoethyl]-7-(4-fluorobenzyl)-3-[(methylamino)carbonyl]-2-oxo-1,2-dihydro-1,5-naphthyridin-4-olate; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-[2-(methylamino)-2-oxoethyl]-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; Sodium 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-3-({[2-(methyloxy)ethyl]amino}carbonyl)-2-oxo-1,2-dihydro-1,5-naphthyridin-4-olate; 7-(4-Fluorobenzyl)-4-hydroxy-N-[(2R)-2-hydroxypropyl]-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; Sodium 7-[(4-fluorophenyl)methyl]-3-({[(2R)-2-hydroxypropyl]amino}carbonyl)-2-oxo-1-[2-(2-oxo-1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridin-4-olate; 7-(4-Fluorobenzyl)-4-hydroxy-N-[(2S)-2-hydroxypropyl]-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-(2-Amino-2-oxoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-(4-Fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; Sodium 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-3-{[(2-hydroxyethyl)amino]carbonyl}-2-oxo-1,2-dihydro-1,5-naphthyridin-4-olate; N-[(2R)-2,3-Dihydroxypropyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-Fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-[(1-methyl-1H-imidazol-2-yl)methyl]-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; Sodium 7-[(4-fluorophenyl)methyl]-1-[(1-methyl-1H-imidazol-2-yl)methyl]-3-({[2-(methyloxy)ethyl]amino}carbonyl)-2-oxo-1,2-dihydro-1,5-naphthyridin-4-olate; 1-Ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1S)-2-hydroxy-1-methylethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; Sodium 1-ethyl-7-[(4-fluorophenyl)methyl]-3-({[(1S)-2-hydroxy-1-methylethyl]amino}carbonyl)-2-oxo-1,2-dihydro-1,5-naphthyridin-4-olate; and pharmaceutically acceptable salts thereof.
36 . A compound selected from the group consisting of:
7-Benzyl-4-hydroxy-N-(2-methoxyethyl)-1-(2-morpholin-4-yl-2-oxoethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(Dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-Fluorobenzyl)-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-Fluorobenzyl)-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-[2-(Ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[2-(4-morpholinyl)-2-oxoethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-N-[2-(2-oxo-1-imidazolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; (±)-1-[2-(Dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(Dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1,1-dimethylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-{2-[(1-methylethyl)sulfonyl]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(Cyclopropylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-{2-[[(Dimethylamino)carbonyl](methyl)amino]ethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-Fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1-[2-oxo-2-(1,3-thiazolidin-3-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxypropyl)-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-N-[(2S)-2-hydroxypropyl]-1-[3-(methyloxy)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxybutyl)-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-Fluorobenzyl)-4-hydroxy-1-{2-[(2-methoxyethyl)amino]-2-oxoethyl}-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-[3-(2-oxo-1-piperidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxypropyl)-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1S)-2-hydroxy-1-methylethyl]-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; and pharmaceutically acceptable salts thereof.
37 . A compound selected from the group consisting of
7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-[2-(2-oxo-1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxybutyl)-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-[3-(methyloxy)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1-[2-oxo-2-(1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)ethyl]-2-oxo-1-[2-oxo-2-(1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-[2-oxo-2-(1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; (±)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[1-methyl-2-(methyloxy)ethyl]-2-oxo-1-[2-oxo-2-(1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; (±)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1-[2-oxo-2-(1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-oxo-2-(1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; (±)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1-[2-oxo-2-(1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-(2-amino-2-oxoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-methyl-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(2-methylpropyl)-2-oxo-N-[2-(2-oxo-1-imidazolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-(cyclopropylmethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-(2-methoxy-1-methylethyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-(3-morpholin-4-ylpropyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[2-(4-morpholinyl)-2-oxoethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; (±)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[1-methyl-2-(methyloxy)ethyl]-1-[2-(4-morpholinyl)-2-oxoethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; (±)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-1-[2-(4-morpholinyl)-2-oxoethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-[3-(1-pyrrolidinylsulfonyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-2-oxo-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; (±)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[1-methyl-2-(methyloxy)ethyl]-2-oxo-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-(4-pyridinylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; (±)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(dimethylamino)-2-oxoethyl]-7-(4-fluorobenzyl)-4-hydroxy-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(dimethylamino)-2-oxoethyl]-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(diethylamino)-2-oxoethyl]-7-(4-fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(2-hydroxyethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-N-[2-(2-oxo-1-imidazolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1,1-dimethylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-(2,3-dihydroxypropyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-[2-(acetylamino)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-(2-pyridinylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(1-methylethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(2,4-difluorophenyl)methyl]-1-[2-(dimethylamino)-2-oxoethyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(2S)-2-hydroxypropyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; (±)-1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-{2-[(dimethylamino)sulfonyl]ethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-[(1S)-2-hydroxy-1-methylethyl]-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-[(1R)-2-hydroxy-1-methylethyl]-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-[2-(acetylamino)ethyl]-1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1R)-2-hydroxy-1-methylethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[methyl(methylsulfonyl)amino]ethyl}-1-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[1-(hydroxymethyl)cyclopentyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1,1-dimethylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-{2-[(1-methylethyl)sulfonyl]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(1H-imidazol-4-ylmethyl)-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-[(2S)-2-hydroxypropyl]-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-[(2R)-2-hydroxypropyl]-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-(3-methoxypropyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-(3-hydroxypropyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-{2-[acetyl(methyl)amino]ethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[2-(methylamino)-2-oxoethyl]-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(cyclopropylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(cyclopropylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(cyclopropylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-{2-[[(dimethylamino)carbonyl](methyl)amino]ethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[3-(2,5-dioxo-1-pyrrolidinyl)propyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-[2-(acetylamino)ethyl]-1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(acetylamino)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(acetylamino)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1,1-dimethylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; N-[(2R)-2,3-dihydroxypropyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-(2-{[(dimethylamino)carbonyl]amino}ethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-(2-{[(dimethylamino)carbonyl]amino}ethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-(2-{[(dimethylamino)carbonyl]amino}ethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[1-(hydroxymethyl)-2-methylpropyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-(2-{[(dimethylamino)carbonyl]amino}ethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[1-methyl-2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-(2-{[(dimethylamino)carbonyl]amino}ethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1,1-dimethylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(3,4-difluorophenyl)methyl]-1-[2-(dimethylamino)-2-oxoethyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(3,4-difluorophenyl)methyl]-1-[2-(dimethylamino)-2-oxoethyl]-4-hydroxy-N-[(2S)-2-hydroxypropyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-2-oxo-1-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; methyl {2-[7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-3-({[3-(2-oxo-1-pyrrolidinyl)propyl]amino}carbonyl)-1,5-naphthyridin-1(2H)-yl]ethyl}carbamate; N-[(2S)-2,3-dihydroxypropyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-pyrrolidinyl)ethyl]-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{1-[(methyloxy)methyl]propyl}-2-oxo-1-[2-(2-oxo-1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[1-(hydroxymethyl)-2-methylpropyl]-2-oxo-1-[2-(2-oxo-1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[1-(hydroxymethyl)butyl]-2-oxo-1-[2-(2-oxo-1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-{2-[acetyl(methyl)amino]ethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1S)-2-hydroxy-1-methylethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-Fluorophenyl)methyl]-4-hydroxy-N-[(2S)-2-hydroxypropyl]-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1R)-2-hydroxy-1-methylethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[1-methyl-2-(methyloxy)ethyl]-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(4-hydroxybutyl)-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1-(2-oxo-2-thiomorpholin-4-ylethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1-[2-oxo-2-(1,3-thiazolidin-3-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-{2-[ethyl(methyl)amino]-2-oxoethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-{2-[methyl(methyloxy)amino]-2-oxoethyl}-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(2R)-2-hydroxypropyl]-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxypropyl)-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxybutyl)-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1R)-1-(hydroxymethyl)-3-methylbutyl]-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(2S)-2-hydroxypropyl]-1-[3-(methyloxy)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1R)-2-hydroxy-1-methylethyl]-1-[3-(methyloxy)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1S)-2-hydroxy-1-methylethyl]-1-[3-(methyloxy)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-{2-[acetyl(methyl)amino]ethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(2R)-2-hydroxypropyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-{2-[acetyl(methyl)amino]ethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1S)-2-hydroxy-1-methylethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxybutyl)-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-{2-[acetyl(methyl)amino]ethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxy-2-methylpropyl)-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-1-[2-(methylamino)-2-oxoethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-methyl-2-oxo-1-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-1-[2-(isopropylamino)-2-oxoethyl]-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-1-{2-[(methyloxy)amino]-2-oxoethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-1-{2-[(2-methoxyethyl)amino]-2-oxoethyl}-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-{2-[acetyl(methyl)amino]ethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1R)-2-hydroxy-1-methylethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-cyclopropyl-N-[(2R)-2,3-dihydroxypropyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(ethylamino)-2-oxoethyl]-7-(4-fluorobenzyl)-4-hydroxy-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(tert-butylamino)-2-oxoethyl]-7-(4-fluorobenzyl)-4-hydroxy-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-[3-(2-oxo-1-piperidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-2-oxo-1-[3-(2-oxo-1-piperidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1R)-2-hydroxy-1-methylethyl]-2-oxo-1-[3-(2-oxo-1-piperidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1S)-2-hydroxy-1-methylethyl]-2-oxo-1-[3-(2-oxo-1-piperidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-{2-[(cyclopropylmethyl)amino]-2-oxoethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-1-(2-{[2-(methyloxy)ethyl]amino}-2-oxoethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-[4-(methyloxy)phenyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(ethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(2S)-2-hydroxypropyl]-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxypropyl)-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(2R)-2-hydroxypropyl]-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxybutyl)-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1S)-2-hydroxy-1-methylethyl]-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1R)-2-hydroxy-1-methylethyl]-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide and pharmaceutically acceptable salts thereof.
38 . A compound selected from the group consisting of
7-benzyl-4-hydroxy-N-(2-methoxyethyl)-1-(2-morpholin-4-yl-2-oxoethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(5-fluoro-2-pyridinyl)methyl]-4-hydroxy-N-[3-(4-morpholinyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-(4-fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-1-[2-(4-morpholinyl)-2-oxoethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[2-(4-morpholinyl)-2-oxoethyl]-N-[3-(4-morpholinyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-[2-(4-morpholinyl)-2-oxoethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-[2-(4-morpholinyl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide; 1-[2-(dimethylamino)-2-oxoethyl]-7-(4-fluorobenzyl)-4-hydroxy-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide and pharmaceutically acceptable salts thereof.
39 . A compound according to any one of claims 33 - 38 wherein the pharmaceutically acceptable salt is a sodium salt.
40 . A pharmaceutical composition comprising a compound according to any one of claims 33 - 38 together with a pharmaceutically acceptable carrier.
41 . A pharmaceutical composition according to claim 40 in the form of a tablet or capsule.
42 . A pharmaceutical composition according to claim 40 in the form of a liquid or suspension.
43 . A method of treatment of an HIV infection in a human comprising administering to said human an antiviral effective amount of a compound according to any one of claims 33 - 38 .Cited by (0)
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