JP2005510500A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- VFMFLUJKDPHHOJ-UHFFFAOYSA-N 2-[1-benzoyl-4-[2-(dimethylamino)acetyl]piperazin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound C1N(C(=O)CN(C)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 VFMFLUJKDPHHOJ-UHFFFAOYSA-N 0.000 claims 1
- HJVVPRFMGAXBBU-UHFFFAOYSA-N 2-[2,4-dimethyl-1-(pyrazine-2-carbonyl)piperazin-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=1C1(C)CN(C)CCN1C(=O)C1=CN=CC=N1 HJVVPRFMGAXBBU-UHFFFAOYSA-N 0.000 claims 1
- RRCRJINQPBQCTE-UHFFFAOYSA-N 2-[2-(benzylamino)propan-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)NCC1=CC=CC=C1 RRCRJINQPBQCTE-UHFFFAOYSA-N 0.000 claims 1
- XVMDRYMHVXBQJJ-UHFFFAOYSA-N 2-[2-(diethylamino)propan-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CCN(CC)C(C)(C)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 XVMDRYMHVXBQJJ-UHFFFAOYSA-N 0.000 claims 1
- KGQNIYANRJZBMK-UHFFFAOYSA-N 2-[2-(dimethylamino)-1-methoxypropan-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound COCC(C)(N(C)C)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 KGQNIYANRJZBMK-UHFFFAOYSA-N 0.000 claims 1
- AYVJOZSHFYTOFL-UHFFFAOYSA-N 2-[2-(dimethylamino)propan-2-yl]-n-[(2-ethoxyphenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CCOC1=CC=CC=C1CNC(=O)C1=NC(C(C)(C)N(C)C)=NC(O)=C1O AYVJOZSHFYTOFL-UHFFFAOYSA-N 0.000 claims 1
- FFSPADXXZZKMRW-UHFFFAOYSA-N 2-[2-(dimethylamino)propan-2-yl]-n-[(4-fluoro-2-methylsulfonylphenyl)methyl]-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(F)=CC=2)S(C)(=O)=O)=N1 FFSPADXXZZKMRW-UHFFFAOYSA-N 0.000 claims 1
- LISAKYCVZZAOKQ-UHFFFAOYSA-N 2-[2-(ethylcarbamoylamino)propan-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CCNC(=O)NC(C)(C)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 LISAKYCVZZAOKQ-UHFFFAOYSA-N 0.000 claims 1
- BXJHDHIQZFYDQA-UHFFFAOYSA-N 2-[2-[2-(dimethylamino)acetyl]-3,4-dihydro-1h-isoquinolin-3-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CN(C)CC(=O)N1CC2=CC=CC=C2CC1C(N=1)=NC(O)=C(O)C=1C(=O)NCC1=CC=C(F)C=C1 BXJHDHIQZFYDQA-UHFFFAOYSA-N 0.000 claims 1
- WDIHLPRBTQAXPZ-UHFFFAOYSA-N 2-[2-[4-(dimethylamino)piperidin-1-yl]propan-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound C1CC(N(C)C)CCN1C(C)(C)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 WDIHLPRBTQAXPZ-UHFFFAOYSA-N 0.000 claims 1
- XQLOUFZQHGRQRR-UHFFFAOYSA-N 2-[2-[acetyl(methyl)amino]-1-methoxypropan-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound COCC(C)(N(C)C(C)=O)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 XQLOUFZQHGRQRR-UHFFFAOYSA-N 0.000 claims 1
- OLTFTRIKEMMVCQ-UHFFFAOYSA-N 2-[2-[acetyl(methyl)amino]propan-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CC(=O)N(C)C(C)(C)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 OLTFTRIKEMMVCQ-UHFFFAOYSA-N 0.000 claims 1
- JJKYFXHNCNXYTG-UHFFFAOYSA-N 2-[2-[benzyl(methyl)amino]propan-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)N(C)CC1=CC=CC=C1 JJKYFXHNCNXYTG-UHFFFAOYSA-N 0.000 claims 1
- HVPAJBSOGTVLTI-UHFFFAOYSA-N 2-[2-[cyclohexylmethyl(methyl)amino]-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)N(C)CC1CCCCC1 HVPAJBSOGTVLTI-UHFFFAOYSA-N 0.000 claims 1
- SRCNEXKTBGMIJT-UHFFFAOYSA-N 2-[4-(diethylaminomethyl)phenyl]-n-[(2,3-dimethoxyphenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound C1=CC(CN(CC)CC)=CC=C1C1=NC(O)=C(O)C(C(=O)NCC=2C(=C(OC)C=CC=2)OC)=N1 SRCNEXKTBGMIJT-UHFFFAOYSA-N 0.000 claims 1
- BYAYOQKXFJUFRC-UHFFFAOYSA-N 2-[4-(dimethylamino)oxan-4-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=1C1(N(C)C)CCOCC1 BYAYOQKXFJUFRC-UHFFFAOYSA-N 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- FXYCBSKYZNXARF-UHFFFAOYSA-N N1=CN=C(C=C1)C(=O)NC(CC1=CC=CC=C1)NC(=O)C1=NC=CC=C1 Chemical compound N1=CN=C(C=C1)C(=O)NC(CC1=CC=CC=C1)NC(=O)C1=NC=CC=C1 FXYCBSKYZNXARF-UHFFFAOYSA-N 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- LWPBISSPQDDFIQ-UHFFFAOYSA-N benzyl n-[2-[6-[(4-fluoro-2-methylsulfonylphenyl)methylcarbamoyl]-5-hydroxy-4-oxo-1h-pyrimidin-2-yl]propan-2-yl]carbamate Chemical compound N=1C(O)=C(O)C(C(=O)NCC=2C(=CC(F)=CC=2)S(C)(=O)=O)=NC=1C(C)(C)NC(=O)OCC1=CC=CC=C1 LWPBISSPQDDFIQ-UHFFFAOYSA-N 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- JMFVWNKPLURQMI-UHFFFAOYSA-N cyclopentyl carbamate Chemical compound NC(=O)OC1CCCC1 JMFVWNKPLURQMI-UHFFFAOYSA-N 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- AKXQXLDIVXPBFH-UHFFFAOYSA-N n-[(2,3-dimethoxyphenyl)methyl]-2-(1,2-dimethylpiperidin-2-yl)-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2C(=C(O)N=C(N=2)C2(C)N(CCCC2)C)O)=C1OC AKXQXLDIVXPBFH-UHFFFAOYSA-N 0.000 claims 1
- VLQHHECTQBNDOQ-UHFFFAOYSA-N n-[(2,3-dimethoxyphenyl)methyl]-2-[1-[2-(dimethylamino)acetyl]piperidin-2-yl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2C(=C(O)N=C(N=2)C2N(CCCC2)C(=O)CN(C)C)O)=C1OC VLQHHECTQBNDOQ-UHFFFAOYSA-N 0.000 claims 1
- OPLQOMFKCXWVET-UHFFFAOYSA-N n-[(2,3-dimethoxyphenyl)methyl]-2-[2-(dimethylamino)propan-2-yl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2C(=C(O)N=C(N=2)C(C)(C)N(C)C)O)=C1OC OPLQOMFKCXWVET-UHFFFAOYSA-N 0.000 claims 1
- ZLXIKTBVSSRIBK-UHFFFAOYSA-N n-[(3-bromo-4-fluorophenyl)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=C(Br)C(F)=CC=2)=N1 ZLXIKTBVSSRIBK-UHFFFAOYSA-N 0.000 claims 1
- PLKRHIVQWVWLER-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-(1-formamido-2-methoxyethyl)-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound COCC(NC=O)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 PLKRHIVQWVWLER-UHFFFAOYSA-N 0.000 claims 1
- OZIOVYNGGNOHJN-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-2-(2-morpholin-4-ylpropan-2-yl)-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)N1CCOCC1 OZIOVYNGGNOHJN-UHFFFAOYSA-N 0.000 claims 1
- UWJXLUKXNKKSGD-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-2-(7-methyl-7-azabicyclo[2.2.1]heptan-4-yl)-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound CN1C(CC2)CCC12C(N=1)=NC(O)=C(O)C=1C(=O)NCC1=CC=C(F)C=C1 UWJXLUKXNKKSGD-UHFFFAOYSA-N 0.000 claims 1
- JNAAWILZJQMWIF-UXHICEINSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-2-[(2s,4r)-1-methyl-4-phenylmethoxypiperidin-2-yl]-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound N=1C([C@@H]2C[C@@H](CCN2C)OCC=2C=CC=CC=2)=NC(O)=C(O)C=1C(=O)NCC1=CC=C(F)C=C1 JNAAWILZJQMWIF-UXHICEINSA-N 0.000 claims 1
- LFEJBNSZPNQXNF-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxamide Chemical compound OC1=NC=NC(C(=O)NCC=2C=CC(F)=CC=2)=C1O LFEJBNSZPNQXNF-UHFFFAOYSA-N 0.000 claims 1
- AFNUBWCLISMHFF-MOPGFXCFSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-2-[(2s,4r)-4-phenylmethoxypiperidin-2-yl]-1h-pyrimidine-6-carboxamide Chemical compound OC=1C(O)=NC([C@H]2NCC[C@H](C2)OCC=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 AFNUBWCLISMHFF-MOPGFXCFSA-N 0.000 claims 1
- PYPHGZUHAPCWCP-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-2-[1-(phenylcarbamoyl)piperidin-2-yl]-1h-pyrimidine-6-carboxamide Chemical compound OC=1C(O)=NC(C2N(CCCC2)C(=O)NC=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 PYPHGZUHAPCWCP-UHFFFAOYSA-N 0.000 claims 1
- JZZYHJZLQMOBDJ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-4-oxo-2-thiomorpholin-3-yl-1h-pyrimidine-6-carboxamide Chemical compound OC=1C(O)=NC(C2NCCSC2)=NC=1C(=O)NCC1=CC=C(F)C=C1 JZZYHJZLQMOBDJ-UHFFFAOYSA-N 0.000 claims 1
- DMMMFITWWRFSND-UHFFFAOYSA-N n-[(5-chloro-2-methylphenyl)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=C(Cl)C=2)C)=N1 DMMMFITWWRFSND-UHFFFAOYSA-N 0.000 claims 1
- WPWJBCMPZBKJEB-UHFFFAOYSA-N n-[2-[6-[(4-fluorophenyl)methylcarbamoyl]-5-hydroxy-4-oxo-1h-pyrimidin-2-yl]propan-2-yl]-4-methylmorpholine-2-carboxamide Chemical compound C1N(C)CCOC1C(=O)NC(C)(C)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 WPWJBCMPZBKJEB-UHFFFAOYSA-N 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- HMDRFBDRCNKGFM-UHFFFAOYSA-N tert-butyl n-[2-[6-[(4-fluorophenyl)methylcarbamoyl]-5-hydroxy-4-oxo-1h-pyrimidin-2-yl]-1-methoxypropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(COC)C1=NC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 HMDRFBDRCNKGFM-UHFFFAOYSA-N 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 0 *CNC(c1ncnc(O)c1O)=O Chemical compound *CNC(c1ncnc(O)c1O)=O 0.000 description 2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34819501P | 2001-10-26 | 2001-10-26 | |
| PCT/GB2002/004742 WO2003035076A1 (en) | 2001-10-26 | 2002-10-21 | Dihydroxypyrimidine carboxamide inhibitors of hiv integrase |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005510500A JP2005510500A (ja) | 2005-04-21 |
| JP2005510500A5 true JP2005510500A5 (https=) | 2006-01-05 |
| JP4351053B2 JP4351053B2 (ja) | 2009-10-28 |
Family
ID=23366990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003537643A Expired - Fee Related JP4351053B2 (ja) | 2001-10-26 | 2002-10-21 | ジヒドロキシピリミジンカルボキサミド系ｈｉｖインテグラーゼ阻害薬 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7232819B2 (https=) |
| EP (1) | EP1441734B1 (https=) |
| JP (1) | JP4351053B2 (https=) |
| AT (1) | ATE355064T1 (https=) |
| AU (1) | AU2002334205B2 (https=) |
| CA (1) | CA2463975A1 (https=) |
| CY (1) | CY1106606T1 (https=) |
| DE (1) | DE60218511T2 (https=) |
| DK (1) | DK1441734T3 (https=) |
| ES (1) | ES2281565T3 (https=) |
| PT (1) | PT1441734E (https=) |
| SI (1) | SI1441734T1 (https=) |
| WO (1) | WO2003035076A1 (https=) |
Families Citing this family (165)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6545004B1 (en) | 1999-10-27 | 2003-04-08 | Cytokinetics, Inc. | Methods and compositions utilizing quinazolinones |
| US7230000B1 (en) | 1999-10-27 | 2007-06-12 | Cytokinetics, Incorporated | Methods and compositions utilizing quinazolinones |
| CA2425440C (en) | 2000-10-12 | 2010-04-13 | 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 |
| US6919351B2 (en) | 2000-10-12 | 2005-07-19 | Merck & Co., Inc. | Aza-and polyaza-naphthalenyl-carboxamides useful as HIV integrase inhibitors |
| US7169932B2 (en) | 2001-06-11 | 2007-01-30 | Pfizer Inc. | HIV protease inhibitors, compositions containing the same, their pharmaceutical uses, material for their synthesis |
| HN2002000136A (es) | 2001-06-11 | 2003-07-31 | Basf Ag | Inhibidores de la proteasa del virus hiv, compuestos que contienen a los mismos, sus usos farmaceuticos y los materiales para su sintesis |
| 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 |
| BR0211750A (pt) | 2001-08-10 | 2004-10-13 | Shionogi & Co | Agente 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 |
| NZ533057A (en) * | 2001-10-26 | 2005-11-25 | Angeletti P Ist Richerche Bio | N-substituted hydroxypyrimidinone carboxamide inhibitors of HIV integrase |
| EP1441734B1 (en) * | 2001-10-26 | 2007-02-28 | Istituto di Richerche di Biologia Molecolare P. Angeletti S.p.A. | Dihydroxypyrimidine carboxamide inhibitors of hiv integrase |
| WO2003070701A2 (en) | 2002-02-15 | 2003-08-28 | Cytokinetics, Inc. | Syntheses of quinazolinones |
| WO2003077857A2 (en) | 2002-03-15 | 2003-09-25 | Merck & Co., Inc. | N-(substituted benzyl)-8-hydroxy-1,6-naphthyridine-7- carboxamides useful as hiv integrase inhibitors |
| CA2485148A1 (en) | 2002-05-09 | 2003-11-20 | Cytokinetics, Inc. | Pyrimidinone compounds, compositions and methods |
| US7214800B2 (en) | 2002-05-09 | 2007-05-08 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| JP2005530806A (ja) * | 2002-05-23 | 2005-10-13 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン阻害薬 |
| EP1513820A4 (en) | 2002-05-23 | 2006-09-13 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| US7109186B2 (en) | 2002-07-09 | 2006-09-19 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| AU2003256805A1 (en) | 2002-07-23 | 2004-02-09 | Cytokinetics, Inc. | Compounds compositions and methods |
| CA2498111A1 (en) | 2002-09-11 | 2004-03-25 | Merck & Co., Inc. | Dihydroxypyridopyrazine-1,6-dione compounds useful as hiv integrase inhibitors |
| JP2005538184A (ja) | 2002-09-11 | 2005-12-15 | 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剤として有用な８−ヒドロキシ−１−オキソ−テトラヒドロピロロピラジン化合物 |
| WO2004034972A2 (en) | 2002-09-30 | 2004-04-29 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| PA8586801A1 (es) | 2002-10-31 | 2005-02-04 | Pfizer | Inhibidores de hiv-integrasa, composiciones farmaceuticas y metodos para su uso |
| EP1578748B1 (en) * | 2002-12-27 | 2010-09-15 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Tetrahydro-4h-pyrido[1,2-a]pyrimidines and related compounds useful as hiv integrase inhibitors |
| WO2004062613A2 (en) * | 2003-01-13 | 2004-07-29 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| BRPI0407052A (pt) | 2003-01-27 | 2006-01-17 | Pfizer | Inibidores da hiv-integrase, composições farmacêuticas, e métodos para sua utilização |
| US7037908B2 (en) | 2003-04-24 | 2006-05-02 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| TW200510425A (en) | 2003-08-13 | 2005-03-16 | Japan Tobacco Inc | Nitrogen-containing fused ring compound and use thereof as HIV integrase inhibitor |
| CA2542047A1 (en) * | 2003-10-20 | 2005-05-12 | Merck & Co., Inc. | Hydroxy pyridopyrrolopyrazine dione compounds useful as hiv integrase inhibitors |
| US20050090668A1 (en) * | 2003-10-28 | 2005-04-28 | Dreher Spencer D. | Preparation of 5-hydroxy-6-oxo-1,6-dihydropyrimidine compounds |
| US20050176767A1 (en) * | 2003-10-30 | 2005-08-11 | Laval Chan Chun Kong | Pyridine carboxamide and methods for inhibiting HIV integrase |
| JP2007510652A (ja) * | 2003-11-03 | 2007-04-26 | サイトキネティクス・インコーポレーテッド | ピリミジン−４−オン化合物、組成物、および方法 |
| EP1692112A4 (en) | 2003-12-08 | 2008-09-24 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS, AND METHODS |
| AR046938A1 (es) * | 2003-12-12 | 2006-01-04 | Merck & Co Inc | Procedimiento para preparar hexahidropirimido[1,2-a]azepin-2-carboxilatos y compuetos similares |
| JP2007518711A (ja) | 2003-12-19 | 2007-07-12 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン阻害剤 |
| TW200526635A (en) | 2003-12-22 | 2005-08-16 | Shionogi & Co | Hydroxypyrimidinone derivative having HIV integrase inhibitory activity |
| MXPA06007906A (es) * | 2004-01-12 | 2007-02-14 | Gilead Sciences Inc | Compuestos antivirales de fosfonato de pirimidilo y metodos de uso. |
| JP2007528396A (ja) | 2004-03-09 | 2007-10-11 | 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 |
| JP2007528394A (ja) | 2004-03-09 | 2007-10-11 | 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 |
| EP1725556A1 (en) | 2004-03-09 | 2006-11-29 | Merck & Co., Inc. | Hiv integrase inhibitors |
| WO2005087766A1 (en) | 2004-03-09 | 2005-09-22 | Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa | Hiv integrase inhibitors |
| WO2005103003A2 (en) * | 2004-04-26 | 2005-11-03 | Pfizer Inc. | Pyrrolopyridine derivatives and their use as hiv-integrase inhibitors |
| BRPI0510306A (pt) | 2004-04-26 | 2007-09-04 | Pfizer | inibidores da enzima de hiv integrase,composição farmacêutica contendo os referidos inibidores bem como seu uso |
| US7618981B2 (en) * | 2004-05-06 | 2009-11-17 | Cytokinetics, Inc. | Imidazopyridinyl-benzamide anti-cancer agents |
| US7504413B2 (en) * | 2004-05-06 | 2009-03-17 | Cytokinetics, Inc. | N-(4-(imidazo[1,2A]pyridin-YL)phenethyl)benzamide inhibitors of the mitotic kinesin CENP-E for treating certain cellular proliferation diseases |
| US7795448B2 (en) * | 2004-05-06 | 2010-09-14 | Cytokinetics, Incorporated | Imidazoyl-benzamide anti-cancer agents |
| ES2529038T3 (es) * | 2004-05-07 | 2015-02-16 | Merck Sharp & Dohme Corp. | Inhibidores de la integrasa de VIH |
| US7273859B2 (en) | 2004-05-12 | 2007-09-25 | Bristol-Myers Squibb Company | HIV integrase inhibitors: cyclic pyrimidinone compounds |
| US7115601B2 (en) * | 2004-05-18 | 2006-10-03 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| US7176196B2 (en) | 2004-05-28 | 2007-02-13 | Bristol-Myers Squibb Company | Bicyclic heterocycles as HIV integrase inhibitors |
| US7157447B2 (en) | 2004-05-28 | 2007-01-02 | Bristol-Myers Squibb Company | Bicyclic heterocycles as HIV integrase inhibitors |
| US7192948B2 (en) | 2004-05-28 | 2007-03-20 | Bristol-Myers Squibb Company | Bicyclic heterocycles as HIV integrase inhibitors |
| US7173022B2 (en) | 2004-05-28 | 2007-02-06 | Bristol-Myers Squibb Company | Bicyclic heterocycles as HIV integrase inhibitors |
| US7476666B2 (en) | 2004-06-09 | 2009-01-13 | Merck & Co., Inc. | HIV integrase inhibitors |
| US7429604B2 (en) * | 2004-06-15 | 2008-09-30 | Bristol Myers Squibb Company | Six-membered heterocycles useful as serine protease inhibitors |
| CN101014572B (zh) * | 2004-09-15 | 2011-07-06 | 盐野义制药株式会社 | 具有hiv整合酶抑制活性的氨基甲酰基吡啶酮衍生物 |
| EP1819341A4 (en) | 2004-11-10 | 2011-06-29 | Synta Pharmaceuticals Corp | IL-12 MODULATORY CONNECTIONS |
| EP1819323B2 (en) * | 2004-12-03 | 2023-03-22 | Merck Sharp & Dohme Corp. | Pharmaceutical composition containing an anti-nucleating agent |
| MX2007006635A (es) * | 2004-12-03 | 2007-06-19 | Merck & Co Inc | Formulacion farmaceutica de inhibidores dela carboxamida vih integrasa que contienen una composicion que controla la velocidad de liberacion. |
| RU2403066C2 (ru) * | 2004-12-03 | 2010-11-10 | Мерк Шарп Энд Домэ Корп | Применение атазанавира для улучшения фармакокинетики лекарственных средств, метаболизируемых ugt1a1 |
| ATE516026T1 (de) | 2005-02-21 | 2011-07-15 | Shionogi & Co | Bicyclisches carbamoylpyridonderivat mit hiv- integrase-hemmender wirkung |
| CN101146811B (zh) * | 2005-03-31 | 2012-01-11 | P.安杰莱蒂分子生物学研究所 | Hiv整合酶抑制剂 |
| US8129385B2 (en) | 2005-04-28 | 2012-03-06 | Shionogi & Co., Ltd. | Substituted 5-hydroxy-3,4,6,9,9a, 10-hexanhydro-2h-1-oxa04a,8a-diaza-anthracene-6,10-dioness |
| CA2607151C (en) * | 2005-05-10 | 2012-06-19 | Merck & Co., Inc. | Hiv integrase inhibitors |
| WO2007007588A1 (ja) * | 2005-07-08 | 2007-01-18 | Ono Pharmaceutical Co., Ltd. | 平面性を有する環状基を母核とする化合物 |
| CA2616314A1 (en) * | 2005-07-27 | 2007-02-01 | Gilead Sciences, Inc. | Antiviral phosphonate conjugates for inhibition of hiv |
| CA2622639C (en) * | 2005-10-04 | 2012-01-03 | Istituto Di Recerche Di Biologia Molecolare P. Angeletti S.P.A. | Hiv integrase inhibitors |
| EA200801144A1 (ru) | 2005-10-27 | 2008-10-30 | Сионоги Энд Ко., Лтд. | Полициклическое карбамоилпиридоновое производное, обладающее ингибиторной активностью в отношении интегразы вич |
| JP2009513640A (ja) * | 2005-10-27 | 2009-04-02 | メルク エンド カムパニー インコーポレーテッド | Ｈｉｖインテグラーゼインヒビター |
| WO2007056056A2 (en) * | 2005-11-02 | 2007-05-18 | Cytokinetics, Inc. | Mitotic kinesin inhibitors |
| US20070129379A1 (en) * | 2005-12-01 | 2007-06-07 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| WO2008004100A2 (en) | 2006-07-05 | 2008-01-10 | Pfizer Products Inc. | Therapeutic compounds |
| US20100056516A1 (en) * | 2006-07-17 | 2010-03-04 | Williams Peter D | 1-hydroxy naphthyridine compounds as anti-hiv agents |
| WO2008048538A1 (en) * | 2006-10-18 | 2008-04-24 | Merck & Co., Inc. | Hiv integrase inhibitors |
| US7763630B2 (en) * | 2007-06-06 | 2010-07-27 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| WO2010042392A2 (en) * | 2008-10-06 | 2010-04-15 | Merck & Co., Inc. | Hiv integrase inhibitors |
| MX2011008276A (es) * | 2009-02-06 | 2011-12-14 | Elan Pharm Inc | Inhibidores de quinasa jun n-terminal. |
| US8143244B2 (en) * | 2009-02-26 | 2012-03-27 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| DE102009038123A1 (de) * | 2009-08-17 | 2011-02-24 | Aicuris Gmbh & Co. Kg | Substituierte (Thiazolyl-carbonyl)imidazolidinone und ihre Verwendung |
| US8383639B2 (en) | 2009-10-15 | 2013-02-26 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| IN2012DN03377A (https=) | 2009-10-26 | 2015-10-23 | Merck Sharp & Dohme | |
| SG10201408512RA (en) | 2009-12-23 | 2015-02-27 | Univ Leuven Kath | Novel antiviral compounds |
| US8283366B2 (en) | 2010-01-22 | 2012-10-09 | Ambrilia Biopharma, Inc. | Derivatives of pyridoxine for inhibiting HIV integrase |
| WO2011129095A1 (ja) | 2010-04-12 | 2011-10-20 | 塩野義製薬株式会社 | インテグラーゼ阻害活性を有するピリドン誘導体 |
| KR20110123657A (ko) * | 2010-05-07 | 2011-11-15 | 에스케이케미칼주식회사 | 피콜린아마이드 및 피리미딘-4-카복사미드 화합물, 이의 제조방법 및 이를 함유하는 약제학적 조성물 |
| JP2013542243A (ja) | 2010-11-15 | 2013-11-21 | カトリーケ ウニヴェルシテイト ルーヴェン | 新規な抗ウイルス性化合物 |
| WO2012066442A1 (en) | 2010-11-15 | 2012-05-24 | Pfizer Limited | Inhibitors of hiv replication |
| GB201021104D0 (en) | 2010-12-13 | 2011-01-26 | Univ Leuven Kath | Novel compounds for the treatment of neurodegenerative diseases |
| EP2729448B1 (en) | 2011-07-06 | 2015-09-09 | Gilead Sciences, Inc. | Compounds for the treatment of hiv |
| WO2013030665A1 (en) * | 2011-09-02 | 2013-03-07 | Purdue Pharma L.P. | Pyrimidines as sodium channel blockers |
| EP2774928B1 (en) | 2011-10-12 | 2017-08-30 | Shionogi & Co., Ltd. | Polycyclic pyridone derivative having integrase-inhibiting activity |
| US9013997B2 (en) * | 2012-06-01 | 2015-04-21 | Broadcom Corporation | System for performing distributed data cut-through |
| KR20150039832A (ko) | 2012-08-06 | 2015-04-13 | 사피라 파르마슈티칼즈 게엠베하 | 디하이드록시피리미딘 탄산 유도체 및 바이러스성 질환의 치료, 개선 또는 예방에서의 이의 용도 |
| CN102911124B (zh) * | 2012-10-25 | 2015-11-25 | 山东大学 | 羟基嘧啶酮类化合物及其制备方法与应用 |
| EP2931730B1 (en) | 2012-12-17 | 2019-08-07 | Merck Sharp & Dohme Corp. | 4-pyridinonetriazine derivatives as hiv integrase inhibitors |
| EP2986291B1 (en) | 2013-04-16 | 2020-05-27 | Merck Sharp & Dohme Corp. | 4-pyridone derivative compounds and uses thereof as hiv integrase inhibitors |
| AU2014267951A1 (en) | 2013-05-17 | 2015-11-19 | Merck Sharp & Dohme Corp. | Fused Tricyclic Heterocyclic compounds as HIV integrase inhibitors |
| US9951079B2 (en) | 2013-06-13 | 2018-04-24 | Merck Sharp & Dohme Corp. | Fused tricyclic heterocyclic compounds as HIV integrase inhibitors |
| CA2920815C (en) * | 2013-08-14 | 2021-09-21 | Kalvista Pharmaceuticals Limited | Inhibitors of plasma kallikrein |
| TWI636047B (zh) | 2013-08-14 | 2018-09-21 | 英商卡爾維斯塔製藥有限公司 | 雜環衍生物 |
| MD4794B1 (ro) | 2013-09-27 | 2022-02-28 | Merck Sharp & Dohme Corp | Derivaţi de chinolizină substituiţi utili ca inhibitori de integrază HIV |
| WO2015096651A1 (en) | 2013-12-23 | 2015-07-02 | Merck Sharp & Dohme Corp. | Pyrimidone carboxamide compounds as pde2 inhibitors |
| WO2015130964A1 (en) | 2014-02-28 | 2015-09-03 | Gilead Sciences, Inc. | Therapeutic compounds |
| WO2016027879A1 (ja) | 2014-08-22 | 2016-02-25 | 塩野義製薬株式会社 | インテグラーゼ阻害活性を有する多環性ピリドン誘導体 |
| US9463201B2 (en) | 2014-10-19 | 2016-10-11 | M.G. Therapeutics Ltd | Compositions and methods for the treatment of meibomian gland dysfunction |
| GB201421085D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | New enzyme inhibitors |
| GB201421083D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | Enzyme inhibitors |
| SI3259253T1 (sl) | 2015-02-16 | 2020-07-31 | The University Of Queensland | Sulfonilsečnine in sorodne spojine ter njihova uporaba |
| WO2016145614A1 (en) | 2015-03-17 | 2016-09-22 | Merck Sharp & Dohme Corp. | Triazolyl pyrimidinone compounds as pde2 inhibitors |
| WO2016154081A1 (en) | 2015-03-26 | 2016-09-29 | Merck Sharp & Dohme Corp. | Pyrazolyl pyrimidinone compounds as pde2 inhibitors |
| WO2016187788A1 (en) | 2015-05-25 | 2016-12-01 | Merck Sharp & Dohme Corp. | Fused tricyclic heterocyclic compounds useful for treating hiv infection |
| US10647727B2 (en) | 2015-06-25 | 2020-05-12 | Merck Sharp & Dohme Corp. | Substituted pyrazolo/imidazolo bicyclic compounds as PDE2 inhibitors |
| WO2017000277A1 (en) | 2015-07-01 | 2017-01-05 | Merck Sharp & Dohme Corp. | Substituted triazolo bicycliccompounds as pde2 inhibitors |
| WO2017001926A2 (en) | 2015-07-01 | 2017-01-05 | Lifesci Pharmaceuticals, Inc | Therapeutic inhibitory compounds |
| ES3007759T3 (en) | 2015-09-28 | 2025-03-20 | Azura Ophthalmics Ltd | Thiol and disulfide-containing agents for increasing meibomian gland lipid secretion |
| US10548910B2 (en) | 2015-11-17 | 2020-02-04 | Merck Sharp & Dohme Corp. | Amido-substituted pyridotriazine derivatives useful as HIV integrase inhibitors |
| WO2017106071A1 (en) | 2015-12-15 | 2017-06-22 | Merck Sharp & Dohme Corp. | Spirocyclic quinolizine derivatives useful as hiv integrase inhibitors |
| JP7114076B2 (ja) | 2015-12-22 | 2022-08-08 | シャイ・セラピューティクス・エルエルシー | がん及び炎症性疾患の処置のための化合物 |
| WO2017113288A1 (en) | 2015-12-31 | 2017-07-06 | Merck Sharp & Dohme Corp. | Fused tricyclic heterocyclic compounds as hiv integrase inhibitors |
| CN114469991A (zh) | 2016-04-14 | 2022-05-13 | 阿祖拉眼科有限公司 | 用于治疗睑板腺功能障碍的二硫化硒组合物 |
| IL263235B (en) | 2016-05-31 | 2022-07-01 | Kalvista Pharmaceuticals Ltd | History of pyrazoles as plasma kallikrein inhibitors |
| GB201609603D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-[(6-cyano-2-fluoro-3-methoxyphenyl)Methyl]-3-(methoxymethyl)-1-({4-[(2-ox opyridin-1-YL)Methyl]phenyl}methyl)pyrazole-4-carboxamide |
| GB201609607D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-(3-Fluoro-4-methoxypyridin-2-yl)methyl)-3-(methoxymethyl)-1-({4-((2-oxopy ridin-1-yl)methyl)phenyl}methyl)pyrazole-4-carboxamide and salts |
| KR20230011471A (ko) | 2016-08-19 | 2023-01-20 | 길리애드 사이언시즈, 인코포레이티드 | Hiv 바이러스 감염의 예방적 또는 치유적 치료에 유용한 치료 화합물 |
| EP3290412A1 (en) | 2016-08-31 | 2018-03-07 | Università degli Studi di Siena | Hiv-1 nucleocapsid inhibitors |
| US10934312B2 (en) | 2016-12-02 | 2021-03-02 | Merck Sharp & Dohme Corp. | Tricyclic heterocycle compounds useful as HIV integrase inhibitors |
| JOP20190130A1 (ar) | 2016-12-02 | 2019-06-02 | Merck Sharp & Dohme | مركبات حلقية غير متجانسة رباعية الحلقات مفيدة كمثبطات إنزيم مدمج لفيروس نقص المناعة البشرية (hiv) |
| WO2018140368A1 (en) | 2017-01-26 | 2018-08-02 | Merck Sharp & Dohme Corp. | Substituted quinolizine derivatives useful as hiv integrase inhibitors |
| JP7514005B2 (ja) | 2017-06-21 | 2024-07-10 | シャイ・セラピューティクス・エルエルシー | がん、炎症性疾患、ラソパシー、及び線維性疾患の治療のためのｒａｓスーパーファミリーと相互作用する化合物 |
| NZ760129A (en) | 2017-07-07 | 2025-12-19 | Inflazome Ltd | Novel sulfonamide carboxamide compounds |
| EP3649112A1 (en) | 2017-07-07 | 2020-05-13 | Inflazome Limited | Sulfonylureas and sulfonylthioureas as nlrp3 inhibitors |
| EP3668843A1 (en) | 2017-08-15 | 2020-06-24 | Inflazome Limited | Sulfonylureas and sulfonylthioureas as nlrp3 inhibitors |
| MA49903A (fr) | 2017-08-15 | 2020-06-24 | Inflazome Ltd | Sulfonylureés et sulfonylthioureés en tant qu'inhibiteurs de nlrp3 |
| JP2020531435A (ja) * | 2017-08-15 | 2020-11-05 | インフレイゾーム リミテッド | 新規なスルホンアミドカルボキサミド化合物 |
| EP3668840A1 (en) | 2017-08-15 | 2020-06-24 | Inflazome Limited | Novel sulfonamide carboxamide compounds |
| UY37848A (es) | 2017-08-15 | 2019-03-29 | Inflazome Ltd | Sulfonilureas y sulfoniltioureas útiles como inhibidores de nlrp3 |
| EP3668601A1 (en) | 2017-08-15 | 2020-06-24 | Inflazome Limited | Novel sulfonamide carboxamide compounds |
| AR112412A1 (es) | 2017-08-17 | 2019-10-23 | Gilead Sciences Inc | Formas de sal de colina de un inhibidor de la cápside del vih |
| TWI687415B (zh) | 2017-08-17 | 2020-03-11 | 美商基利科學股份有限公司 | Hiv蛋白質膜抑制劑之固體形式 |
| MX2020003242A (es) | 2017-09-22 | 2020-09-18 | Jubilant Epipad LLC | Compuestos heterociclicos como inhibidores de pad. |
| AU2018352142B2 (en) | 2017-10-18 | 2022-08-25 | Jubilant Epipad LLC | Imidazo-pyridine compounds as PAD inhibitors |
| KR20200085836A (ko) | 2017-11-06 | 2020-07-15 | 주빌런트 프로델 엘엘씨 | Pd1/pd-l1 활성화 억제제로서의 피리미딘 유도체 |
| WO2019092171A1 (en) | 2017-11-09 | 2019-05-16 | Inflazome Limited | Novel sulfonamide carboxamide compounds |
| CN111315733A (zh) | 2017-11-09 | 2020-06-19 | 英夫拉索姆有限公司 | 新颖磺酰胺甲酰胺化合物 |
| BR112020010322A2 (pt) | 2017-11-24 | 2020-11-17 | Jubilant Episcribe Llc | composto da fórmula i; composto da fórmula ia; composto da fórmula ib; processo de preparação de compostos da fórmula i; composição farmacêutica; método para o tratamento e/ou prevenção de várias doenças; uso dos compostos; método para o tratamento de câncer; e método para o tratamento e/ou prevenção de uma afecção mediada por prmt5 ou um distúrbio proliferativo ou câncer |
| HUE057912T2 (hu) | 2017-11-29 | 2022-06-28 | Kalvista Pharmaceuticals Ltd | Plazma kallikrein inhibitort tartalmazó dózisformák |
| GB201719881D0 (en) | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of plasma kallikrein inhibitor and salts thereof |
| US10836746B2 (en) | 2018-02-15 | 2020-11-17 | Gilead Sciences, Inc. | Therapeutic compounds |
| WO2019161280A1 (en) | 2018-02-16 | 2019-08-22 | Gilead Sciences, Inc. | Methods and intermediates for preparing a therapeutic compound useful in the treatment of retroviridae viral infection |
| SG11202008950PA (en) | 2018-03-13 | 2020-10-29 | Jubilant Prodel LLC | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
| CN112088005A (zh) * | 2018-04-27 | 2020-12-15 | 默沙东公司 | 可用作hiv整合酶抑制剂的三环杂环化合物 |
| CN120053445A (zh) | 2018-07-16 | 2025-05-30 | 吉利德科学公司 | 用于治疗hiv的衣壳抑制剂 |
| JP7407461B2 (ja) | 2018-12-19 | 2024-01-04 | シャイ・セラピューティクス・エルエルシー | がん、炎症性疾患、ｒａｓ病、及び線維性疾患の処置のためのｒａｓスーパーファミリーと相互作用する化合物 |
| WO2021028645A1 (en) | 2019-08-09 | 2021-02-18 | Kalvista Pharmaceuticals Limited | Plasma kallikrein inhibitors |
| TWI854067B (zh) | 2019-11-26 | 2024-09-01 | 美商基利科學股份有限公司 | 預防hiv之蛋白殼抑制劑 |
| JP2023503672A (ja) * | 2019-11-29 | 2023-01-31 | 江蘇恒瑞医薬股▲ふん▼有限公司 | 縮合ピリジン環誘導体、その調製方法及びその医薬的応用 |
| CA3166357A1 (en) | 2020-01-10 | 2021-07-15 | Azura Ophthalmics Ltd. | Instructions for composition and sensitivity |
| BR112022020291A2 (pt) * | 2020-04-07 | 2022-12-06 | Mitobridge Inc | Inibidores de cd38 |
| PL4172157T3 (pl) | 2020-06-25 | 2026-03-23 | Gilead Sciences, Inc. | Inhibitory kapsydu w leczeniu hiv |
| JP7765637B2 (ja) | 2021-12-03 | 2025-11-06 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｉｖウイルス感染症のための治療化合物 |
| DK4445900T3 (da) | 2021-12-03 | 2025-08-18 | Gilead Sciences Inc | Terapeutiske forbindelser til hiv-virusinfektion |
| WO2023102523A1 (en) | 2021-12-03 | 2023-06-08 | Gilead Sciences, Inc. | Therapeutic compounds for hiv virus infection |
| WO2025264724A1 (en) * | 2024-06-20 | 2025-12-26 | The Regents Of The University Of California | Mpro inhibitors and uses thereof |
| CN119371360B (zh) * | 2024-09-30 | 2025-10-24 | 暨南大学 | 一种5,6-二羟基嘧啶类化合物及其制备方法和应用 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4636508A (en) * | 1985-04-22 | 1987-01-13 | Uniroyal Chemical Company, Inc. | 5-pyrimidinecarboxyamides and treatment of leukemia therewith |
| US5637618A (en) | 1990-06-01 | 1997-06-10 | Bioresearch, Inc. | Specific eatable taste modifiers |
| TW287160B (https=) | 1992-12-10 | 1996-10-01 | Hoffmann La Roche | |
| NO934505L (no) | 1992-12-10 | 1994-06-13 | Foster Wheeler Energy Ltd | Fremgangsmåte for fremstilling av en organisk væske |
| US6632823B1 (en) | 1997-12-22 | 2003-10-14 | Merck & Co., Inc. | Substituted pyridine compounds useful as modulators of acetylcholine receptors |
| WO1999062520A1 (en) * | 1998-06-03 | 1999-12-09 | Merck & Co., Inc. | Hiv integrase inhibitors |
| US6306891B1 (en) | 1998-06-03 | 2001-10-23 | Merck & Co., Inc. | HIV integrase inhibitors |
| EP1086091A4 (en) * | 1998-06-03 | 2001-10-10 | Merck & Co Inc | INTEGRASE HIV INHIBITORS |
| MXPA01001843A (es) | 1998-08-20 | 2002-04-08 | Toyama Chemical Co Ltd | Derivados de carboxamida heterociclica con nitrogeno o sales derivados de los mismos y agentes antivirales que comprenden los mismos. |
| WO2000051990A1 (en) | 1999-03-04 | 2000-09-08 | Korea Research Institute Of Chemical Technology | Antiviral 2,4-pyrimidinedione derivatives and process for the preparation thereof |
| JP2003503386A (ja) | 1999-06-25 | 2003-01-28 | メルク エンド カムパニー インコーポレーテッド | １−（芳香族またはヘテロ芳香族置換）−３−（ヘテロ芳香族置換）−１，３−プロパンジオン類およびそれの使用 |
| WO2001085700A2 (en) | 2000-05-08 | 2001-11-15 | Janssen Pharmaceutica N.V. | Hiv replication inhibiting pyrimidines and triazines |
| 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 |
| US6919351B2 (en) | 2000-10-12 | 2005-07-19 | Merck & Co., Inc. | Aza-and polyaza-naphthalenyl-carboxamides useful as HIV integrase inhibitors |
| JP2004513134A (ja) | 2000-10-12 | 2004-04-30 | 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−ナフタレニルケトン類 |
| 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 |
| CA2425440C (en) | 2000-10-12 | 2010-04-13 | Merck & Co., Inc. | Aza- and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| JP3616628B2 (ja) | 2001-03-01 | 2005-02-02 | 塩野義製薬株式会社 | Ｈｉｖインテグラーゼ阻害活性を有する含窒素芳香族複素環化合物 |
| BR0211750A (pt) | 2001-08-10 | 2004-10-13 | Shionogi & Co | Agente antiviral |
| NZ533057A (en) * | 2001-10-26 | 2005-11-25 | Angeletti P Ist Richerche Bio | N-substituted hydroxypyrimidinone carboxamide inhibitors of HIV integrase |
| EP1441734B1 (en) * | 2001-10-26 | 2007-02-28 | Istituto di Richerche di Biologia Molecolare P. Angeletti S.p.A. | Dihydroxypyrimidine carboxamide inhibitors of hiv integrase |
| US7109186B2 (en) | 2002-07-09 | 2006-09-19 | 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 EP EP02801949A patent/EP1441734B1/en not_active Expired - Lifetime
- 2002-10-21 PT PT02801949T patent/PT1441734E/pt unknown
- 2002-10-21 WO PCT/GB2002/004742 patent/WO2003035076A1/en not_active Ceased
- 2002-10-21 DK DK02801949T patent/DK1441734T3/da active
- 2002-10-21 CA CA002463975A patent/CA2463975A1/en not_active Abandoned
- 2002-10-21 SI SI200230523T patent/SI1441734T1/sl unknown
- 2002-10-21 AT AT02801949T patent/ATE355064T1/de active
- 2002-10-21 JP JP2003537643A patent/JP4351053B2/ja not_active Expired - Fee Related
- 2002-10-21 DE DE60218511T patent/DE60218511T2/de not_active Expired - Lifetime
- 2002-10-21 US US10/493,279 patent/US7232819B2/en not_active Expired - Fee Related
- 2002-10-21 AU AU2002334205A patent/AU2002334205B2/en not_active Ceased
- 2002-10-21 ES ES02801949T patent/ES2281565T3/es not_active Expired - Lifetime
-
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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005510500A5 (https=) | ||
| JP2005511543A5 (https=) | ||
| RU2361860C2 (ru) | Новые замещенные 3-сера-индолы | |
| RU2454405C2 (ru) | Производные 3-пиридинкарбоксамида и 2-пиразинкарбоксамида в качестве агентов, повышающих уровень лвп-холестерина | |
| RU2009125620A (ru) | Органические соединения | |
| RU2436776C2 (ru) | ДИАРИЛАМИН-СОДЕРЖАЩИЕ СОЕДИНЕНИЯ, КОМПОЗИЦИИ И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ МОДУЛЯТОРОВ РЕЦЕПТОРОВ с-КIT | |
| RU2140918C1 (ru) | Три-замещенные имидазолы, обладающие терапевтическими свойствами, способ получения, фармацевтическая композиция, способ лечения | |
| US5686455A (en) | Imidazole derivatives and their use as cytokine inhibitors | |
| JP2007517010A5 (https=) | ||
| JP2019533694A5 (https=) | ||
| JP2006528939A5 (https=) | ||
| JPWO2019155399A5 (https=) | ||
| JP2013517273A5 (https=) | ||
| RU2005136368A (ru) | Производные пиперазина и их применение для лечения неврологических и психиатрических заболеваний | |
| AU2019203119A1 (en) | Urea derivative or pharmacologically acceptable salt thereof | |
| JP2004506718A5 (https=) | ||
| JP2006500348A5 (https=) | ||
| JP2005531524A (ja) | プロスタグランジンｆ受容体のモジュレーターとしてのチアゾリジンカルボキサミド誘導体 | |
| JP2012517479A5 (https=) | ||
| JP2002516909A5 (https=) | ||
| JP2020506946A5 (https=) | ||
| ME00427B (me) | N-supstituisani hidroksipiramidinon karboksamidni inhibitori hiv integraze | |
| JP2010505832A5 (https=) | ||
| AR076375A1 (es) | Piperazinil azetidinil amidas heteroaromaticas y aromaticas como inhibidores de lipasas de monoacilglicerol. | |
| JP2008520637A5 (https=) |