Pyridine carboxamide and methods for inhibiting HIV integrase
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Accused Products
Abstract
Compounds of formula I:
wherein R1, R2, R4, R10, R11, and Q are as defined herein, and their pharmaceutically acceptable salts, are useful in the prevention or treatment of HIV infections.
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Citations
66 Claims
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1. A compound according to formula I
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66)
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2. A compound according to claim 1, wherein:
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R1 is hydrogen or C1-6 alkyl;
R2 is hydroxyl, C1-6 alkoxy or C6aryl-C1-6 alkyloxy;
R3 is amino, azido, hydroxyl, halogen, cyano, carboxy, C1-6 alkoxy, 5-6 membered heterocycle, or C6aryl-C1-6 alkyloxy;
R4 is hydrogen, halogen, hydroxyl, carboxy, C1-6 alkyl, C1-6 alkoxy, 5-6 membered heterocycle, or C6-10 aryl;
R10, R11, R12 are each independently hydrogen or C1-10 alkyl; and
Q is optionally substituted phenyl;
with the proviso that when R3 is methoxy, R2 is hydroxyl, R1 is hydrogen and R4 is hydrogen then Q is phenyl substituted by at least 3 substituents.
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3. A compound according to claim 1, wherein R1 is hydrogen or C1-10 alkyl.
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4. A compound according to claim 1, wherein R1 is methyl, ethyl, propyl, isopropyl, cyclopropyl or cyclohexyl.
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5. A compound according to claim 1, wherein R2 is hydroxyl, C1-10alkoxy or C6aryl-C1-10 alkyloxy.
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6. A compound according to claim 1, wherein R2 is hydroxyl or C1-10 alkoxy.
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7. A compound according to claim 1, wherein R2 is C1-3 alkoxy.
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8. A compound according to claim 1, wherein R2 is methoxy, ethyloxy, propyloxy, isopropyloxy, cyclopropyloxy or cyclohexyloxy.
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9. A compound according to claim 1, wherein R2 is methoxy or benzyloxy.
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10. A compound according to claim 1, wherein R3 is amino, amido, sulfonamido, azido, hydroxyl, halogen, cyano, carboxyl, C1-10 alkoxy, 5-6 membered heterocycle, C6aryl-C1-10 alkyloxy, C10 alkyl, or SOnR12.
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11. A compound according to claim 1, wherein R3 is hydroxyl, halogen, C1-10 alkoxy or 5-6 membered heterocycle.
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12. A compound according to, claim 1, wherein R3 is methoxy, ethyloxy, propyloxy, isopropyloxy, cyclopropyloxy and cyclohexyloxy.
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13. A compound according to claim 1, wherein R3 is methoxy, amino, azido, hydroxyl, halogen, cyano, carboxy, amido, sulfonamide, or SOnR12.
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14. A compound according to claim 1, wherein R3 is pyridinyl, thiazolyl, furanyl, thienyl or piperidinyl.
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15. A compound according to claim 1, wherein R3 is 2-pyridinyl, 2-thiazolyl, 2-furanyl, 2-thienyl or 1-piperidinyl.
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16. A compound according to claim 1, wherein R3 is benzyloxy.
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17. A compound according to claim 1, wherein R4 is hydrogen, halogen, hydroxyl, carboxy, C1-10alkyl, amino, amido, sulfonamide, SOnR12, C1-10 alkoxy, 5-6 membered heterocycle, or C50 heteroaryl.
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18. A compound according to claim 1, wherein R4 is halogen, C1-10 alkyl, C1-10 alkoxy or 5-6 membered heterocycle.
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19. A compound according to claim 1, wherein R4 is C1-3 alkyl.
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20. A compound according to claim 1, wherein R4 is methyl, ethyl, propyl, isopropyl, vinyl, 1,2-dihydroxyethyl, hydroxymethyl, methyloxymethyl, cyclopropyl or cyclohexyl;
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21. A compound according to claim 1, wherein R4 is methyl, ethyl, vinyl, 1,2-dihydroxyethyl, hydroxymethyl or methyloxymethyl.
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22. A compound according to claim 1, wherein R4 is hydroxyl, carboxy, aryl, amino, amido, sulfonamide, SOnR12, or C1-10 alkoxy.
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23. A compound according to claim 1, wherein R4 is methoxy, ethyloxy, propyloxy, isopropyloxy, cyclopropyloxy or cyclohexyloxy.
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24. A compound according to claim 1, wherein R4 is 5-6 membered heterocycle.
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25. A compound according to claim 1, wherein R4 is furanyl, tetrahydrofuranyl, thienyl, thiazolyl, pyridinyl, 2,2-dimethyl[1,3]dioxolanyl or piperidinyl.
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26. A compound according to claim 1, wherein R10 and R11 are each independently hydrogen or C1-10 alkyl.
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27. A compound according to claim 1, wherein R10 and R11 are each C1-10 alkyl.
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28. A compound according to claim 1, wherein R10 is hydrogen and R11 is C1-10 alkyl.
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29. A compound according to claim 1, wherein R10 is hydrogen and R11 is methyl.
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30. A compound according to claim 1, wherein R10 and R11 are each C1-3 alkyl.
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31. A compound according to claim 1, wherein Q is optionally substituted phenyl, C1-10 alkyl, 5-6 membered heterocycle or C7-12aralkyl.
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32. A compound according to claim 1, wherein Q is C1-10 alkyl, cyclohexyl, 5-6 membered heterocycle, 2-pyridinyl, C7-12aralkyl, benzyl, or phenyl.
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33. A compound according to claim 1, wherein
Q is phenyl substituted by one or more substituents independently selected from halogen, amino, amidino, amido, azido, cyano, guanidino, hydroxyl, nitro, nitroso, urea, OS(O)2Rm, OS(O)2ORn, S(O)2ORp, S(O)0-2Rq, OP(O)ORsORt, P(O)OR5ORt, C(O)ORv, NRxC(O)Rw or SO2NRyRz; -
Rm is C1-10 alkyl, C6-10 aryl or 3-10 membered heterocycle;
Rn is H, C10 alkyl, C6-10 aryl or 3-10 membered heterocycle;
Rp is H, C1-10 alkyl, C6-10 aryl or 3-10 membered heterocycle;
Rq is H, C1-10 alkyl, C6-10 aryl or 3-10 membered heterocycle;
Rs and Rt are each independently H or C1-10 alkyl, C1-10alkyl, C6-12aralkyl, C6-10aryl, C1-10alkoxy, C6-12aralkyloxy, C6-10aryloxy, 3-10 membered heterocycle, or C(O)Ru;
Ru is H, C1-10 alkyl, C6-10 aryl, C6-12 aralkyl or 3-10 membered heterocycle, or C(O)ORv;
Rv is H, C1-10 alkyl, C6-10 aryl, C6-12 aralkyl or 3-10 membered heterocycle, Rx is H or C1-10alkyl, and Rw is H, C1-10 alkyl, C6-10 aryl, C6-12 aralkyl (or 3-10 membered heterocycle, or Rx and Rw, taken together with the atoms to which they are attached, form a 3 to 10 membered heterocycle; and
Ry and Rz are each independently H, C1-10 alkyl, C6-10 aryl, C3-10 heterocycle or C6-12 aralkyl.
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35. A compound according to claim 1, wherein
Q is phenyl substituted by one or more substituents independently selected from halogen, amino, amido, azido, cyano, hydroxyl, urea, S(O)2ORp, S(O)2Rq, P(O)ORsORt, C1-10alkyl, C1-10alkoxy, C(O)Ru, C(O)ORv, NRxC(O)Rw and SO2NRyRz; -
Rp is H or C1-10 alkyl Rq is H or C1-10 alkyl;
Rs and Rt are each independently H or C1-10 alkyl;
Ru is H or C1-10 alkyl Rv is H, or C1-10 alkyl;
Rx is H or C1-10 alkyl;
Rw is H or C1-10 alkyl; and
Ry and Rz are each independently H or C1-10 alkyl.
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36. A compound according to claim 1, wherein
Q is phenyl substituted by one or more substituents independently selected from halogen, amino, amido, azido, cyano, hydroxyl, C1-10alkyl, C1-10alkoxy, C(O)Ru, C(O)ORv, and SO2NRyRz; -
Ru is H or C1-10 alkyl;
Rv is H, or C1-10 alkyl; and
Ry and Rz are each independently H or C1-10 alkyl
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37. A compound according to claim 1, wherein
Q is phenyl substituted by one or more substituents independently selected from halogen, amino, amido, cyano, hydroxyl, C1-10alkyl, C1-10alkoxy, C(O)Ru, C(O)ORv, and SO2NRyRz; -
Ru is H or C1-10 alkyl;
Rv is H, or C1-10 alkyl; and
Ry and Rz are each independently H or C1-10 alkyl
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38. A compound according to claim 1, wherein Q is 4-fluorophenyl.
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39. A compound according to claim 1, wherein:
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R1 is hydrogen or C1-10 alkyl;
R2 is hydroxyl, C1-10 alkoxy or C6aryl-C1-10 alkyloxy;
R3 is amino, amido, sulfonamido, azido, hydroxyl, halogen, cyano, carboxy, C1-10 alkoxy, 5-6 membered heterocycle, C6aryl-C1-10 alkyloxy, C1-10 alkyl, or SOnR12;
n is 0, 1, or 2;
R4 is hydrogen, halogen, hydroxyl, carboxy, C1-10 alkyl, amino, amido, sulfonamide, SOnR12, C1-10 alkoxy, C6-10 aryl, 5-6 membered heterocycle, or C5-10 heteroaryl;
R10 and R11 are each independently selected from hydrogen or C1-10 alkyl; and
Q is a phenyl optionally substituted, C1-10 alkyl, 5-6 membered heterocycle, or C7-12aralkyl.
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40. A compound according to claim 1, wherein:
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R1 is hydrogen or C1-6 alkyl;
R2 is hydroxyl, C1-6 alkoxy or C6aryl-C1-6 alkyloxy;
R3 is amino, azido, hydroxyl, halogen, cyano, carboxy, C1-6 alkoxy, 5-6 membered heterocycle, or C6aryl-C1-6 alkyloxy;
R4 is halogen, hydroxyl, carboxy, C1-6 alkyl, C1-6 alkoxy, 5-6 membered heterocycle, or C6-10 aryl;
R10 and R11 are each independently selected from hydrogen or C1-6 alkyl;
Q is optionally substituted phenyl.
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41. A compound according to claim 1, wherein said compound is a compound of formula II:
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42. A compound according to claim 41, wherein:
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R3 is amino, azido, hydroxyl, halogen, cyano, carboxy, C1-6 alkoxy, 5-6 membered heterocycle, or C6aryl-C1-6 alkyloxy;
R4 is hydrogen, halogen, hydroxyl, carboxy, C1-6 alkyl, C1-6 alkoxy, 5-6 membered heterocycle, or C6-10 aryl;
Q is optionally substituted phenyl.
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43. A compound according to claim 1, wherein said compound is a compound of formula III:
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44. A compound according to claim 43, R4 is halogen, hydroxyl, carboxy, C1-6 alkyl, C1-6 alkoxy, 5-6 membered heterocycle, or C6-10 aryl;
- and Q is a phenyl optionally substituted.
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45. A compound according to claim 1, wherein said compound is selected from:
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3′
-Hydroxy-[2,4′
]bipyridinyl-2′
-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-thiophen-2-yl-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
4-Furan-2-yl-3-hydroxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
4-Cyano-3-hydroxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
2-(4-Fluoro-benzylcarbamoyl)-3-hydroxy-isonicotinic acid;
6-Bromo-3-hydroxy-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-Bromo-3,4-dihydroxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-phenyl-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-Bromo-3-hydroxy-4-thiophen-2-yl-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3,4-Dihydroxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-Furan-2-yl-3-hydroxy-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
4-Bromo-3-hydroxy-6-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
4-Bromo-3,6-dihydroxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-thiophen-2-yl-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-thiazol-2-yl-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
4,6-Dibromo-3-hydroxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-(4-Fluoro-benzylamino)-hydroxy-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
5-Hydroxy-4-methoxy-[2,2′
]bipyridinyl-6-carboxylic acid 4-fluoro-benzylamide;
3,4,6-Trimethoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-Ethyl-3-hydroxy-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-vinyl-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4,6-dimethoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
4-Benzyloxy-6-bromo-3-hydroxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-(1,2-Dihydroxy-ethyl)-3-hydroxy-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
4-Azido-3-benzyloxy-6-bromo-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
4-Amino-3-benzyloxy-6-bromo-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
4-Amino-6-bromo-3-hydroxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
4,6-Dibromo-3-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-6-hydroxymethyl-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
5′
-Hydroxy-4′
-methoxy-3,4,5,6-tetrahydro-2H-[1,2′
]bipyridinyl-6′
-carboxylic acid 4-fluoro-benzylamide;
6-(4-Fluoro-benzylcarbamoyl)-5-hydroxy-4-methoxy-pyridine-2-carboxylic acid;
4-Azido-3-benzyloxy-6-bromo-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-(pyridin-2-ylmethoxy)-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-methoxymethyl-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid benzylamide;
and pharmaceutically acceptable salts thereof.
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46. A compound according to claim 1, wherein said compound is selected from:
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3-hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid [2-(4-fluoro-phenyl)-ethyl]-amide;
3-hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid (pyridin-2-ylmethyl)-amide;
3-hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid cyclohexylmethyl-amide;
(+)-3-hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
(−
)-3-hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
4-acetylamino-3-hydroxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-hydroxy-4-methanesulfonyl-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-furan-2-yl-3-hydroxy-4-methylsulfanyl-pyridine-2-carboxylic acid 4-fluorobenzylamide;
3-hydroxy-6-methoxy-4-vinyl-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-hydroxy-4-phenylacetylamino-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-furan-2-yl-3-hydroxy-4-phenylmethanesulfonylamino-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 4-methyl-benzylamide;
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 4-methoxy-benzylamide;
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 4-trifluoromethoxy-benzylamide;
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 4-trifluoromethyl-benzylamide;
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 2-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 3-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 2,4-difluoro-benzylamide;
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 3,4-difluoro-benzylamide;
3-hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid (4-fluoro-benzyl)-methyl-amide;
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid [1-(4-fluoro-phenyl)-ethyl]-amide;
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 4-bromo-benzylamide;
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 4-chloro-benzylamide;
6-(1,1-Dioxo-[1,2]-thiazinan-2-yl)-3-hydroxy-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-(pyridin-2-yl sulfanyl)-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-methylsulfanyl-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-6-methanesulfonyl-4-methoxy pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-(tetrahydrofuran-3-yl)-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-Furan-3-yl-3-hydroxy-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-(4-Benzoyl-piperazin-1-yl)-3-hydroxy-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-morpholin-4-yl-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-(1,3)-oxathioan-2-yl-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-(5-methyl-(1,3)-oxathioan-2-yl)-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-(1,3)-Dioxolan-2-yl-3-hydroxy-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-(4-methyl-(1,3)dioxolan-2-yl)-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-(4-Benzyloxymethyl-(1,3)-dioxolan-2-yl)-3-hydroxy-4-methoxy-pyridine-2-calboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-6-(4-hydroxymethyl-(1,3)-dioxolan-2-yl)-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-(1,3)-Dioxan-2-yl-3-hydroxy-4-methoxy-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
3-Hydroxy-4-methoxy-6-(2-methyl-(1,3)-dioxolan-2-yl)-pyridine-2-carboxylic acid 4-fluoro-benzylamide;
6-(4-Fluoro-benzylcarbamoyl)-3-hydroxy-4-methoxy-pyridine-2-carboxylic acid methyl ester;
3-Hydroxy-4-methoxy-pyridine-2,6-dicarboxylic acid bis-(4-fluoro-benzylamide);
3-Hydroxy-4-methoxy-6-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid 4-nitro-benzylamide;
3′
-Hydroxy-6′
-(tetrahydro-furan-2-yl)-3,4,5,6-tetrahydro-2H-(1,4′
)bipyridinyl-2′
carboxylic acid 4-fluoro-benzylamide;
and pharmaceutically acceptable salts thereof.
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47. A compound according to claim 1, wherein said compound is the (+) enantiomer having an enantiomeric excess of 90%.
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48. A compound according to claim 1, wherein said compound is the (−
- ) enantiomer having an enantiomeric excess of 90%.
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49. A compound according to claim 1, wherein alkyl is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, isohexyl, neohexyl, allyl, vinyl, acetylenyl, ethylenyl, propenyl, isopropenyl, butenyl, isobutenyl, hexenyl, butadienyl, pentenyl, pentadienyl, hexenyl, hexadienyl, hexatrienyl, heptenyl, heptadienyl, heptatrienyl, octenyl, octadienyl, octatrienyl, octatetraenyl, propynyl, butynyl, pentynyl, hexynyl, cyclopropyl, cyclobutyl, cyclohexenyl, cyclohex-dienyl, cyclohexyl, trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl, chloromethyl, trifluoroethyl, difluoroethyl, fluoroethyl, trichloroethyl, dichloroethyl, chloroethyl, chlorofluoromethyl, chlorodifluoromethyl, or dichlorofluoroethyl.
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50. A compound according to claim 1, wherein alkoxy is methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy, isohexyloxy or neohexyloxy.
-
51. A compound according to claim 1, wherein aryl is phenyl, tolyl, dimethyphenyl, aminophenyl, anilinyl, naphthyl, anthryl, phenanthryl or biphenyl.
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52. A compound according to claim 1, wherein aralkyl is benzyl, benzhydryl, trityl, phenethyl, 3-phenylpropyl, 2-phenylpropyl, 4-phenylbutyl or naphthylmethyl.
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53. A compound according to claim 1, wherein aralkyloxy is benzyloxy, benzhydryloxy, trityloxy, phenethyloxy, 3-phenylpropyloxy, 2-phenylpropyloxy, 4-phenylbutyloxy or naphthylmethoxy.
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54. A pharmaceutical composition comprising a compound according to claim 1 and at least one pharmaceutically acceptable carrier or excipient thereof.
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55. A pharmaceutical composition according to claim 54, further comprising of at least one other antiviral agent.
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56. A method of preventing or treating HIV infection in a subject comprising administering to said subject a therapeutically effective amount of a compound according to claim 1.
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57. A method according to claim 56, wherein said subject is a human.
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58. A method of preventing, delaying or treating AIDS in a subject comprising administering to said subject a therapeutically effective amount of a compound according to claim 1.
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59. A method according to claim 58, wherein said subject is a human.
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60. A method of inhibiting HIV integrase in a subject comprising administering to said subject a therapeutically effective amount of a compound according to claim 1.
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61. A method according to claim 60, wherein said subject is a human.
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62. A method of preventing integration of HIV DNA into host cell DNA in a subject comprising administering to said subject a therapeutically effective amount of a compound according to claim 1.
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63. A method according to claim 62, wherein said subject is a human.
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64. A method of preventing the HIV DNA strand transfer to the host cell DNA in a subject comprising administering to said subject a therapeutically effective amount of a compound according to claim 1.
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65. A method according to claim 64, wherein said subject is a human.
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66. Use of a compound according to claim 1 for the manufacture of a medicament for preventing or treating HIV infection or preventing, delaying or treating AIDS.
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2. A compound according to claim 1, wherein:
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34. A compound according to claim 34, wherein
Rs and Rt are each independently H or C1-10 alkyl, C1-10 alkyl, C7-12aralkyl, C6-10aryl, C1-10alkoxy, C7-12aralkyloxy, C6-10aryloxy, 3-10 membered heterocycle, or C(O)Ru.
Specification
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Current AssigneeVirochem Pharma Inc. (Vertex Pharmaceuticals Incorporated)
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Original AssigneeVirochem Pharma Inc. (Vertex Pharmaceuticals Incorporated)
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InventorsNguyen-Ba, Nghe, Liu, Bingcan, Halab, Liliane, Chan Chun Kong, Laval, Zhang, Ming-Qiang
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Application NumberUS10/976,238Publication NumberTime in Patent OfficeDaysField of SearchUS Class Current514/318CPC Class CodesC04B 35/632 Organic additivesC07D 213/81 Amides; ImidesC07D 213/84 NitrilesC07D 401/04 directly linked by a ring-m...C07D 401/12 linked by a chain containin...C07D 405/04 directly linked by a ring-m...C07D 405/14 containing three or more he...C07D 409/04 directly linked by a ring-m...C07D 411/04 directly linked by a ring-m...C07D 417/04 directly linked by a ring-m...