Hiv integrase inhibitors

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.

1 - 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]-Nexahydro-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]-Nyridin-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.