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US 6,605,614 B2Granted
[1,8] naphthyridine derivatives having antiviral activity
AssigneeBioChem Pharma Inc.
InventorsBenoit Bachand, Nghe Nguyen-Ba, Arshad Siddiqui, Sophie Levesque
Life of this patent
Estimating the term…
Abstract
The present invention is concerned with novel [1,8] naphthyridine derivatives useful for the inhibition of the hepatitis virus, more specifically the hepatitis C virus.
Claims49
A [1,8] naphthyridine compound of Formula I
- Z1, Z1′, Z1″ and Z2 are independently H, halogen, carboxyl, amino, amidino, guanidino, nitro, OH, SH, CN, C1-6 alkoxy or C1-6 heteroalkyl, or are independently C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, which in each case is straight chain, branched chain, or cyclic and is unsubstituted or substituted by halogen, nitro, aminoamidino, amidino, guanido, CONH2, COOH, O—C1-6, alkyl, O—C2-6 alkenyl, O—C2-6 alkynyl, amino, hydroxyl or COOQ, wherein Q is C1-6 alkyl, C2-6 alkenyl, a C2-6 alkynyl;
- X is O, NH or S;
- Y is O, S, (CH2)n, O(CH2)n, or S(CH2)n;
- n is 0 to 6;
- R1 is H, or C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, which in each case is straight chain, branched chain, or cyclic and is unsubstituted or substituted by halogen, nitro, aminoamidino, amidino, guanido, CONH2, COOH, O—C1-6 alkyl, O—C2-6alkenyl, O—C2-6 alkynyl, amino, hydroxyl or COOQ, wherein Q is C1-6 alkyl, C2-6 alkenyl, a C2-6 alkynyl;
- and
- W is C6-12 aryl which is unsubstituted or substituted by C1-6 alkyl, C2-6 alkenyl, a C2-6 alkynyl, halogen, nitro, aminoamidino, amidino, guanido, CONH2, COOH, O—C1-6 alkyl, O—C2-6 alkenyl, C—C2-6 alkynyl, amino, hydroxyl or COOQ, wherein Q is C1-6 alkyl, C2-6 alkenyl, a C2-6 alkynyl, C6-12 heteroaryl which is unsubstituted or substituted by C1-6 alkyl, C2-6 alkenyl, a C2-6 alkynyl, halogen, nitro, aminoamidino, amidino, guanido, CONH2, COOH, O—C1-6 alkyl, O—C2-6 alkenyl, O—C2-6alkynyl, amino, hydroxyl or COOQ, wherein Q is C1-6 alkyl, C2-6alkenyl, a C2-6alkynyl, or C2-12 heterocycle which is unsubstituted or substituted by C1-6 alkyl, C2-6 alkenyl, C2-6 alknyl, C1-6 perfluoralkyl, C1-6 alkoxy, C1-6 perfluoroalkyoxy, C1-6 heteroalkyl, C1-6 perfluoralkythio, halogen, amino, guanidino, amidino, nitro, OH, COOH, SH or CN;
- or a pharmaceutically acceptable salt thereof;
- with the provisos that:
- 1) when Y is CH2, X is O, R1, Z1, Z1′, Z1″ and Z2 are H, then W is not 2-methoxyphenyl or 3-trifluoromethylphenyl;
- and
- 2) when Y is (CH2)0, X is O, R1, Z1, Z1″ and Z2 are H, then W is not phenyl, 3-trifluoromethylphenyl or 3-pyridinyl.
9 more elements
A [1,8] naphthyridine compound selected front:
- [1,8]naphthyridine-2-carboxylic acid benzylamide;
- [1,8] naphthyridine-2-carboxylic acid 4-methoxy-benzylamide;
- [1,8] naphthyridine-2-carboxylic acid 3-methoxy-benzylamide;
- [1,8] naphthyridine-2-carboxylic acid 2,4,6-trimethoxy-benzylamide;
- [1,8] naphthyridine-2-carboxylic acid 2,3-dimethoxy-benzylamide;
- [1,8] naphthyridine-2-carboxylic acid 2,4-dimethoxy-benzylamide;
- [1,8] naphthyridine-2-carboxylic acid 2-isopropoxy-benzylarnide;
- [1,8] naphthyridine-2-carboxylic acid [2-(2-methoxyphenyl)ethyl]-amide;
- [1,8] naphthyridine-2-carboxylic acid (pyridin-3-ymethyl)-amide;
- [1,8] naphthyridine-2-carboxylic acid (pyridin-2-ylmethyl)-amide;
- [1,8] naphthyridine-2-carboxylic acid pyridin-4-ylamide;
- [1,8] naphthyridine-2-carboxylic acid pyridin-2-ylamide;
- [1,8] naphthyridine-2-carboxylic acid 2-fluoro-benzylamide;
- [1,8] naphthyridine-2-carboxylic acid 2-fluro-benzylamide;
- [1,8] naphthyridine-2-carboxylic acid 2-trifluoromethoxy-benzylamide;
- [1,8] naphthyridine-2-carboxylic acid (3-nitrophenyl)-amide;
- N-(5,7-dimethyl-[1,8] naphthyridin-2-yl)-2-(2-methoxyphenyl)-acetamide;
- [1,8] naphthyridine-2-carboxylic acid benzyloxyamide;
- [1,8] naphthyridine-2-carboxylic acid thiazol-2-ylamide;
- [1,8] naphthyridine-2-carboxylic acid benzothiazol-2-ylamide;
- [1,8] naphthyridine-2-carboxylic acid (2-fluoro-phenyl)-amide;
- [1,8] naphthyridine-2-carboxylic acid (2-methoxy-benzyl)-methyl-amide;
- [1,8] naphthyridine-2-carbothioic acid 2-methoxy-benzylamide;
- and
- (2-methoxy-benzyl)-[1,8]naphthyridine-2-carboxamidine trifluoroacetate.
22 more elements
A [1,8] naphthyridine compound selected from:
- (+)-[1,8] naphthyridine-2-carboxylic acid 2-sec-butoxy-benzylamide;
- and
- (−)-[1,8] naphthyridine-2-carboxylic acid 2-sec-butoxy-benzylamide.
A [1,8] naphthyridine compound of Formula I
- wherein A is
- Z1, Z1′, Z1″ and Z2 are independently H, halogen, carboxyl, amino, amidino, guanidino, nitro, OH, SH, CN, C1-6 alkoxy or C1-6 heteroalkyl, or are independently C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, which in each case is straight chain, branched chain, or cyclic and is unsubstituted or substituted by halogen, nitro, aminoamidino, amidino, guanido, CONH2, COOH, O—C1-6 alkyl, O—C2-6 alkenyl, O—C2-6 alkynyl, amino, hydroxyl or COOQ, wherein Q is C1-6 alkyl, C2-6 alkenyl, a C2-6 alkynyl;
- X is O, NH or S;
- Y is O, S, (CH2)n, O(CH2)n, or S(CH2)n;
- n is 0 to 6;
- R1, is H, or C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, which in each case is straight chain, branched chain, or cyclic and is unsubstituted or substituted by halogen, nitro, aminoamidino, amidino, guanido, CONH2, COOH, O—C1-6 alkyl, O—C2-6 alkenyl, O—C2-6alkynyl, amino, hydroxyl or COOQ, wherein Q is C1-6 alkyl, C2-6 alkenyl, a C2-6 alkynyl;
- and
- W is C6-12 aryl, C6-12 heteroaryl, C3-12 heterocycle, which in each case is unsubstituted or is substituted with one or more C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 perfluoroalkyl, C1-6 alkoxy, C1-6 perfluoroalkoxy, C1-6 heteroalkyl, C1-6 perfluoroalkylthio, halogen, amino, guanidino, amidino, nitro, OH, COOH, SH or CN;
- or a pharmaceutically acceptable salt thereof;
- with the provisos that:
- 1) when Y is CH2, X is O, R1, Z1, Z1′,Z1″ and Z2 are H, then W is not 2-methoxyphenyl or 3-trifluoromethylphenyl;
- and
- 2) when Y is (CH2)0, X is O, R1, Z1, Z1′, Z1″ and Z2 are H, then W is not phenyl, 3-trifluoromethylphenyl or 3-pyridinyl.
10 more elements
Dependencies are inferred from the claim text.