JP2005510500A5 - - Google Patents
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- Publication number
- JP2005510500A5 JP2005510500A5 JP2003537643A JP2003537643A JP2005510500A5 JP 2005510500 A5 JP2005510500 A5 JP 2005510500A5 JP 2003537643 A JP2003537643 A JP 2003537643A JP 2003537643 A JP2003537643 A JP 2003537643A JP 2005510500 A5 JP2005510500 A5 JP 2005510500A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- carboxamide
- fluorobenzyl
- dihydroxypyrimidine
- dihydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 201
- 125000001424 substituent group Chemical group 0.000 claims 118
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 56
- 229910052717 sulfur Inorganic materials 0.000 claims 40
- 229910052760 oxygen Inorganic materials 0.000 claims 39
- 125000005842 heteroatom Chemical group 0.000 claims 38
- -1 —OH Chemical group 0.000 claims 38
- 125000003118 aryl group Chemical group 0.000 claims 37
- 229910052736 halogen Inorganic materials 0.000 claims 35
- 150000002367 halogens Chemical group 0.000 claims 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 34
- 125000000623 heterocyclic group Chemical group 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 29
- 125000001072 heteroaryl group Chemical group 0.000 claims 27
- 125000004043 oxo group Chemical group O=* 0.000 claims 22
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 15
- 229920006395 saturated elastomer Polymers 0.000 claims 11
- 125000001624 naphthyl group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims 5
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims 3
- LDIOKBUAEJYCKA-UHFFFAOYSA-N 2-[2-(cyclohexylmethylamino)-1-methoxypropan-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound N=1C(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=NC=1C(C)(COC)NCC1CCCCC1 LDIOKBUAEJYCKA-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- UYPPRFUPWGFUSM-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-[2-(dimethylamino)propan-2-yl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CN(C)C(C)(C)C1=NC(O)=C(O)C(C(=O)NCC=2C(=CC=CC=2)Cl)=N1 UYPPRFUPWGFUSM-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- DWCBYHSUKCYVPJ-UHFFFAOYSA-N 2-(1,2-dimethylpiperidin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CN1CCCCC1(C)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 DWCBYHSUKCYVPJ-UHFFFAOYSA-N 0.000 claims 1
- BPSJQMWOCFUFNY-UHFFFAOYSA-N 2-(1-acetamido-2-methoxyethyl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound COCC(NC(C)=O)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 BPSJQMWOCFUFNY-UHFFFAOYSA-N 0.000 claims 1
- YYFXVAQXNVQXRY-UHFFFAOYSA-N 2-(1-acetamidocyclohexyl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound N=1C(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=NC=1C1(NC(=O)C)CCCCC1 YYFXVAQXNVQXRY-UHFFFAOYSA-N 0.000 claims 1
- ZJNVQCQCAACIOY-UHFFFAOYSA-N 2-(1-acetyl-2,4-dimethylpiperazin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound C1N(C)CCN(C(C)=O)C1(C)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 ZJNVQCQCAACIOY-UHFFFAOYSA-N 0.000 claims 1
- OZQLTBGFEMVVPY-UHFFFAOYSA-N 2-(1-acetyl-2-methylpiperidin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CC(=O)N1CCCCC1(C)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 OZQLTBGFEMVVPY-UHFFFAOYSA-N 0.000 claims 1
- FNHSMRCCFZZPOM-UHFFFAOYSA-N 2-(1-acetyl-4-phenylmethoxypiperidin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CC(=O)N1CCC(OCC=2C=CC=CC=2)CC1C(N=1)=NC(O)=C(O)C=1C(=O)NCC1=CC=C(F)C=C1 FNHSMRCCFZZPOM-UHFFFAOYSA-N 0.000 claims 1
- QMVDQPYTAXMPMU-UHFFFAOYSA-N 2-(1-amino-2-methoxyethyl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound COCC(N)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 QMVDQPYTAXMPMU-UHFFFAOYSA-N 0.000 claims 1
- IWCXYNGHLQKISB-UHFFFAOYSA-N 2-(1-amino-2-phenylethyl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound N=1C(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=NC=1C(N)CC1=CC=CC=C1 IWCXYNGHLQKISB-UHFFFAOYSA-N 0.000 claims 1
- GPOXEULGYOPJPH-UHFFFAOYSA-N 2-(1-aminocyclopentyl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound N=1C(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=NC=1C1(N)CCCC1 GPOXEULGYOPJPH-UHFFFAOYSA-N 0.000 claims 1
- RXUSCVUJWNXOBJ-UHFFFAOYSA-N 2-(1-aminocyclopropyl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound N=1C(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=NC=1C1(N)CC1 RXUSCVUJWNXOBJ-UHFFFAOYSA-N 0.000 claims 1
- JILMJJOGIMQFHV-UHFFFAOYSA-N 2-(1-benzoyl-2,3-dihydroindol-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound OC=1C(O)=NC(C2N(C3=CC=CC=C3C2)C(=O)C=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 JILMJJOGIMQFHV-UHFFFAOYSA-N 0.000 claims 1
- ONVKTXFUNUDZCR-UHFFFAOYSA-N 2-(1-benzoyl-3,4-dihydro-2h-quinolin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound OC=1C(O)=NC(C2N(C3=CC=CC=C3CC2)C(=O)C=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 ONVKTXFUNUDZCR-UHFFFAOYSA-N 0.000 claims 1
- FDVINLRMZUFLME-UHFFFAOYSA-N 2-(1-benzoyl-4-methylpiperazin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound C1N(C)CCN(C(=O)C=2C=CC=CC=2)C1C(N=1)=NC(O)=C(O)C=1C(=O)NCC1=CC=C(F)C=C1 FDVINLRMZUFLME-UHFFFAOYSA-N 0.000 claims 1
- WIPKOECLXGDYLS-UHFFFAOYSA-N 2-(1-benzoylpiperidin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound OC=1C(O)=NC(C2N(CCCC2)C(=O)C=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 WIPKOECLXGDYLS-UHFFFAOYSA-N 0.000 claims 1
- JGTQENIZDSKSJL-UHFFFAOYSA-N 2-(1-benzoylpyrrolidin-2-yl)-n-[(2,3-dimethoxyphenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2C(=C(O)N=C(N=2)C2N(CCC2)C(=O)C=2C=CC=CC=2)O)=C1OC JGTQENIZDSKSJL-UHFFFAOYSA-N 0.000 claims 1
- GCKLTKKFPAOKQL-UHFFFAOYSA-N 2-(1-benzoylpyrrolidin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound OC=1C(O)=NC(C2N(CCC2)C(=O)C=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 GCKLTKKFPAOKQL-UHFFFAOYSA-N 0.000 claims 1
- GQIGTZDPGNPIAA-UHFFFAOYSA-N 2-(1-benzylpiperidin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound OC=1C(O)=NC(C2N(CCCC2)CC=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 GQIGTZDPGNPIAA-UHFFFAOYSA-N 0.000 claims 1
- SOENVEQCDQWQKD-UHFFFAOYSA-N 2-(1-ethyl-4-methylpiperazin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CCN1CCN(C)CC1C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 SOENVEQCDQWQKD-UHFFFAOYSA-N 0.000 claims 1
- CCIDCSNKRNVVRH-UHFFFAOYSA-N 2-(1-ethylpiperidin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CCN1CCCCC1C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 CCIDCSNKRNVVRH-UHFFFAOYSA-N 0.000 claims 1
- VUGCDKRFOMVBGA-UHFFFAOYSA-N 2-(2-acetamido-1-methoxypropan-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound COCC(C)(NC(C)=O)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 VUGCDKRFOMVBGA-UHFFFAOYSA-N 0.000 claims 1
- CFELPQKWHKBOBV-UHFFFAOYSA-N 2-(2-amino-1-methoxypropan-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound COCC(C)(N)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 CFELPQKWHKBOBV-UHFFFAOYSA-N 0.000 claims 1
- LRDYUVZWEPOABJ-UHFFFAOYSA-N 2-(2-aminopropan-2-yl)-n-[(4-fluoro-2-methylsulfonylphenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CC(C)(N)C1=NC(O)=C(O)C(C(=O)NCC=2C(=CC(F)=CC=2)S(C)(=O)=O)=N1 LRDYUVZWEPOABJ-UHFFFAOYSA-N 0.000 claims 1
- ZUSYMDKLSWHVGX-UHFFFAOYSA-N 2-(2-benzamidopropan-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound N=1C(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=NC=1C(C)(C)NC(=O)C1=CC=CC=C1 ZUSYMDKLSWHVGX-UHFFFAOYSA-N 0.000 claims 1
- XXHQSISROYNPGC-UHFFFAOYSA-N 2-(2-benzoyl-3,4-dihydro-1h-isoquinolin-3-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound OC=1C(O)=NC(C2N(CC3=CC=CC=C3C2)C(=O)C=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 XXHQSISROYNPGC-UHFFFAOYSA-N 0.000 claims 1
- GOEWCGSZKQDJSY-UHFFFAOYSA-N 2-(3-acetyl-1,3-thiazolidin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CC(=O)N1CCSC1C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 GOEWCGSZKQDJSY-UHFFFAOYSA-N 0.000 claims 1
- BHAFZQBKRPLKBC-UHFFFAOYSA-N 2-(3-acetyl-3-azabicyclo[2.1.1]hexan-4-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CC(=O)N1CC(C2)CC12C(N=1)=NC(O)=C(O)C=1C(=O)NCC1=CC=C(F)C=C1 BHAFZQBKRPLKBC-UHFFFAOYSA-N 0.000 claims 1
- LIVLQOXYCYKQEQ-UHFFFAOYSA-N 2-(4-acetyl-1,2-dimethylpiperazin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CN1CCN(C(C)=O)CC1(C)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 LIVLQOXYCYKQEQ-UHFFFAOYSA-N 0.000 claims 1
- LHDRZZVWVQWKCA-UHFFFAOYSA-N 2-(4-acetylthiomorpholin-3-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CC(=O)N1CCSCC1C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 LHDRZZVWVQWKCA-UHFFFAOYSA-N 0.000 claims 1
- UNPJAMIEBDZGNF-UHFFFAOYSA-N 2-(4-benzyl-1-methylpiperazin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound C1C(C=2N=C(C(O)=C(O)N=2)C(=O)NCC=2C=CC(F)=CC=2)N(C)CCN1CC1=CC=CC=C1 UNPJAMIEBDZGNF-UHFFFAOYSA-N 0.000 claims 1
- SBIYYVJSOYQJRM-UHFFFAOYSA-N 2-(4-benzylmorpholin-3-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound OC=1C(O)=NC(C2N(CCOC2)CC=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 SBIYYVJSOYQJRM-UHFFFAOYSA-N 0.000 claims 1
- RBCJAIJCBUFFCN-UHFFFAOYSA-N 2-(7-acetyl-7-azabicyclo[2.2.1]heptan-4-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CC(=O)N1C(CC2)CCC12C(N=1)=NC(O)=C(O)C=1C(=O)NCC1=CC=C(F)C=C1 RBCJAIJCBUFFCN-UHFFFAOYSA-N 0.000 claims 1
- YOQZQKMFLYTGPF-UHFFFAOYSA-N 2-N-(pyridin-2-ylmethyl)pyrimidine-2,4-dicarboxamide Chemical compound N1=C(C=CC=C1)CNC(=O)C1=NC=CC(=N1)C(=O)N YOQZQKMFLYTGPF-UHFFFAOYSA-N 0.000 claims 1
- VSANFJNPTKNGGX-IBGZPJMESA-N 2-[(2s)-1-acetyl-2-methylpyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CC(=O)N1CCC[C@@]1(C)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 VSANFJNPTKNGGX-IBGZPJMESA-N 0.000 claims 1
- ZAGAWYAOXNLTNW-RPWUZVMVSA-N 2-[(2s,4r)-1-benzoyl-4-phenylmethoxypyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound OC=1C(O)=NC([C@H]2N(C[C@@H](C2)OCC=2C=CC=CC=2)C(=O)C=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 ZAGAWYAOXNLTNW-RPWUZVMVSA-N 0.000 claims 1
- PRWHXEBMSODDSY-UHFFFAOYSA-N 2-[1-(2,4-dimethyl-1,3-thiazole-5-carbonyl)piperidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound S1C(C)=NC(C)=C1C(=O)N1C(C=2N=C(C(O)=C(O)N=2)C(=O)NCC=2C=CC(F)=CC=2)CCCC1 PRWHXEBMSODDSY-UHFFFAOYSA-N 0.000 claims 1
- SSAYTRLKHCRIJC-UHFFFAOYSA-N 2-[1-(3-chlorobenzoyl)-4-methylpiperazin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound C1N(C)CCN(C(=O)C=2C=C(Cl)C=CC=2)C1C(N=1)=NC(O)=C(O)C=1C(=O)NCC1=CC=C(F)C=C1 SSAYTRLKHCRIJC-UHFFFAOYSA-N 0.000 claims 1
- LHWLKXHFOJYHTR-UHFFFAOYSA-N 2-[1-(dimethylamino)-2-methoxyethyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound COCC(N(C)C)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 LHWLKXHFOJYHTR-UHFFFAOYSA-N 0.000 claims 1
- MDBZIQZRFLMPQL-UHFFFAOYSA-N 2-[1-(dimethylamino)-2-phenylethyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound N=1C(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=NC=1C(N(C)C)CC1=CC=CC=C1 MDBZIQZRFLMPQL-UHFFFAOYSA-N 0.000 claims 1
- ORROWUDOULVDMN-UHFFFAOYSA-N 2-[1-(dimethylamino)cyclohexyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound N=1C(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=NC=1C1(N(C)C)CCCCC1 ORROWUDOULVDMN-UHFFFAOYSA-N 0.000 claims 1
- XOXCGQGZROKGSE-UHFFFAOYSA-N 2-[1-(dimethylamino)cyclopentyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound N=1C(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=NC=1C1(N(C)C)CCCC1 XOXCGQGZROKGSE-UHFFFAOYSA-N 0.000 claims 1
- RDEJAKABTUFKCC-UHFFFAOYSA-N 2-[1-(dimethylamino)cyclopropyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound N=1C(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=NC=1C1(N(C)C)CC1 RDEJAKABTUFKCC-UHFFFAOYSA-N 0.000 claims 1
- YNHCPFIPUYWTMF-UHFFFAOYSA-N 2-[1-[2-(dimethylamino)acetyl]piperidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CN(C)CC(=O)N1CCCCC1C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 YNHCPFIPUYWTMF-UHFFFAOYSA-N 0.000 claims 1
- KCVVTCKVFNVRNY-UHFFFAOYSA-N 2-[1-[[2-(dimethylamino)acetyl]amino]-2-phenylethyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound N=1C(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=NC=1C(NC(=O)CN(C)C)CC1=CC=CC=C1 KCVVTCKVFNVRNY-UHFFFAOYSA-N 0.000 claims 1
- SPWHQOHNJBPDTG-UHFFFAOYSA-N 2-[1-[acetyl(methyl)amino]-2-methoxyethyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound COCC(N(C)C(C)=O)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 SPWHQOHNJBPDTG-UHFFFAOYSA-N 0.000 claims 1
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| NZ525088A (en) | 2000-10-12 | 2004-11-26 | Merck & Co Inc | Aza- and polyaza-naphthalenyl carboxamides useful as HIV integrase inhibitors |
| JP2004517860A (ja) | 2000-10-12 | 2004-06-17 | メルク エンド カムパニー インコーポレーテッド | Ｈｉｖインテグラーゼ阻害薬として有用なアザ−およびポリアザ−ナフタレニルカルボキサミド類 |
| DE60128936T2 (de) | 2000-10-12 | 2008-04-10 | Merck & Co, Inc. | Aza- und polyaza-naphthalenylcarbonsäureamide als hiv-integrase-hemmer |
| US7094909B2 (en) | 2001-06-11 | 2006-08-22 | Agouron Pharmaceuticals, Inc. | HIV protease inhibitors, compositions containing the same, their pharmaceutical uses and materials for their synthesis |
| US7169932B2 (en) | 2001-06-11 | 2007-01-30 | Pfizer Inc. | HIV protease inhibitors, compositions containing the same, their pharmaceutical uses, material for their synthesis |
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| WO2003016275A1 (fr) | 2001-08-10 | 2003-02-27 | Shionogi & Co., Ltd. | Agent antiviral |
| AR036256A1 (es) | 2001-08-17 | 2004-08-25 | Merck & Co Inc | Sal sodica de un inhibidor de integrasa del vih, procesos para su preparacion, composiciones farmaceuticas que lo contienen y su uso para la manufactura de un medicamento |
| EP1441735B1 (en) * | 2001-10-26 | 2006-02-22 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | N-substituted hydroxypyrimidinone carboxamide inhibitors of hiv integrase |
| DE60218511T2 (de) * | 2001-10-26 | 2007-10-25 | Istituto Di Richerche Di Biologia Molecolare P. Angeletti S.P.A. | Dihydroxypyrimidin-carbonsäueramid-hemmer der hiv-integrase |
| WO2003070701A2 (en) | 2002-02-15 | 2003-08-28 | Cytokinetics, Inc. | Syntheses of quinazolinones |
| AU2003220170B2 (en) | 2002-03-15 | 2008-12-11 | Merck Sharp & Dohme Corp. | N-(Substituted benzyl)-8-hydroxy-1,6-naphthyridine-7- carboxamides useful as HIV integrase inhibitors |
| KR20050036911A (ko) * | 2002-05-09 | 2005-04-20 | 싸이토키네틱스, 인코포레이티드 | 화합물들, 방법 및 조성물 |
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| JP5230050B2 (ja) | 2000-05-08 | 2013-07-10 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Ｈｉｖ複製阻害剤 |
| US6339133B1 (en) | 2000-07-05 | 2002-01-15 | Solvay Polyolefins Europe - Belgium | Emergency stop of a polymerization in the gas phase |
| GB0017676D0 (en) | 2000-07-19 | 2000-09-06 | Angeletti P Ist Richerche Bio | Inhibitors of viral polymerase |
| AU2002230392A1 (en) | 2000-10-12 | 2002-05-15 | Merck & Co., Inc. | AZA-and polyaza-naphthalenyl ketones useful as HIV integrase inhibitors |
| DE60128936T2 (de) | 2000-10-12 | 2008-04-10 | Merck & Co, Inc. | Aza- und polyaza-naphthalenylcarbonsäureamide als hiv-integrase-hemmer |
| JP2004517860A (ja) | 2000-10-12 | 2004-06-17 | メルク エンド カムパニー インコーポレーテッド | Ｈｉｖインテグラーゼ阻害薬として有用なアザ−およびポリアザ−ナフタレニルカルボキサミド類 |
| NZ525088A (en) | 2000-10-12 | 2004-11-26 | Merck & Co Inc | Aza- and polyaza-naphthalenyl carboxamides useful as HIV integrase inhibitors |
| MXPA03007765A (es) | 2001-03-01 | 2003-12-08 | Shionogi & Co | Compuestos heteroarilo que contienen nitrogeno, que tienen actividad inhibitoria contra virus de inmunodeficiencia humana integrasa. |
| WO2003016275A1 (fr) | 2001-08-10 | 2003-02-27 | Shionogi & Co., Ltd. | Agent antiviral |
| DE60218511T2 (de) * | 2001-10-26 | 2007-10-25 | Istituto Di Richerche Di Biologia Molecolare P. Angeletti S.P.A. | Dihydroxypyrimidin-carbonsäueramid-hemmer der hiv-integrase |
| EP1441735B1 (en) * | 2001-10-26 | 2006-02-22 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | N-substituted hydroxypyrimidinone carboxamide inhibitors of hiv integrase |
| WO2004004657A2 (en) | 2002-07-09 | 2004-01-15 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| WO2004062613A2 (en) | 2003-01-13 | 2004-07-29 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| US7037908B2 (en) | 2003-04-24 | 2006-05-02 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
-
2002
- 2002-10-21 DE DE60218511T patent/DE60218511T2/de not_active Expired - Lifetime
- 2002-10-21 ES ES02801949T patent/ES2281565T3/es not_active Expired - Lifetime
- 2002-10-21 WO PCT/GB2002/004742 patent/WO2003035076A1/en not_active Ceased
- 2002-10-21 AT AT02801949T patent/ATE355064T1/de active
- 2002-10-21 AU AU2002334205A patent/AU2002334205B2/en not_active Ceased
- 2002-10-21 US US10/493,279 patent/US7232819B2/en not_active Expired - Fee Related
- 2002-10-21 EP EP02801949A patent/EP1441734B1/en not_active Expired - Lifetime
- 2002-10-21 JP JP2003537643A patent/JP4351053B2/ja not_active Expired - Fee Related
- 2002-10-21 SI SI200230523T patent/SI1441734T1/sl unknown
- 2002-10-21 CA CA002463975A patent/CA2463975A1/en not_active Abandoned
- 2002-10-21 DK DK02801949T patent/DK1441734T3/da active
- 2002-10-21 PT PT02801949T patent/PT1441734E/pt unknown
-
2006
- 2006-09-07 US US11/516,831 patent/US7459452B2/en not_active Expired - Fee Related
-
2007
- 2007-05-18 CY CY20071100679T patent/CY1106606T1/el unknown
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