ME00427B - N-supstituisani hidroksipiramidinon karboksamidni inhibitori hiv integraze - Google Patents
N-supstituisani hidroksipiramidinon karboksamidni inhibitori hiv integrazeInfo
- Publication number
- ME00427B ME00427B MEP-2008-637A MEP63708A ME00427B ME 00427 B ME00427 B ME 00427B ME P63708 A MEP63708 A ME P63708A ME 00427 B ME00427 B ME 00427B
- Authority
- ME
- Montenegro
- Prior art keywords
- oxo
- methyl
- hydroxy
- carboxamide
- fluorobenzyl
- Prior art date
Links
- -1 N-substituted hydroxypyrimidinone carboxamide Chemical class 0.000 title claims abstract 13
- 108010002459 HIV Integrase Proteins 0.000 title claims 2
- 239000003112 inhibitor Substances 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 43
- 150000003839 salts Chemical class 0.000 claims abstract 37
- 208000030507 AIDS Diseases 0.000 claims abstract 8
- 208000031886 HIV Infections Diseases 0.000 claims abstract 8
- 208000037357 HIV infectious disease Diseases 0.000 claims abstract 6
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims abstract 6
- 238000000034 method Methods 0.000 claims abstract 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 4
- 239000003443 antiviral agent Substances 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 59
- 125000005842 heteroatom Chemical group 0.000 claims 53
- 125000000623 heterocyclic group Chemical group 0.000 claims 53
- 229910052736 halogen Inorganic materials 0.000 claims 43
- 150000002367 halogens Chemical class 0.000 claims 43
- 229910052760 oxygen Inorganic materials 0.000 claims 41
- 229910052717 sulfur Inorganic materials 0.000 claims 41
- 125000001072 heteroaryl group Chemical group 0.000 claims 37
- 125000004043 oxo group Chemical group O=* 0.000 claims 33
- 125000003118 aryl group Chemical group 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 25
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims 13
- 125000001246 bromo group Chemical group Br* 0.000 claims 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 11
- 125000004434 sulfur atom Chemical group 0.000 claims 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 10
- 229920006395 saturated elastomer Polymers 0.000 claims 9
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 2
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000002777 nucleoside Substances 0.000 claims 2
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 2
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- HALJILNZFAWGDL-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-2-(2-methylphenyl)-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(CCN(C)C)C(C=2C(=CC=CC=2)C)=NC=1C(=O)NCC1=CC=C(F)C=C1 HALJILNZFAWGDL-UHFFFAOYSA-N 0.000 claims 1
- INUPCGQJKUVPAZ-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-6-oxopyrimidine-4-carboxamide Chemical compound O=C1N(CCN(C)C)C=NC(C(=O)NCC=2C=CC(F)=CC=2)=C1O INUPCGQJKUVPAZ-UHFFFAOYSA-N 0.000 claims 1
- ZUEYJJHLMMKJSS-UHFFFAOYSA-N 2-(1,2-dimethyl-4-methylsulfonylpiperazin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CN1CCN(S(C)(=O)=O)CC1(C)C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C ZUEYJJHLMMKJSS-UHFFFAOYSA-N 0.000 claims 1
- HTUOQGFZWIWCSK-UHFFFAOYSA-N 2-(1,4-dimethylpiperazin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound C1N(C)CCN(C)C1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C HTUOQGFZWIWCSK-UHFFFAOYSA-N 0.000 claims 1
- NMUQSBDHGNXUKW-UHFFFAOYSA-N 2-(1-acetylpyrrolidin-2-yl)-5-hydroxy-n-[(2-methoxyphenyl)methyl]-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound COC1=CC=CC=C1CNC(=O)C1=C(O)C(=O)N(C)C(C2N(CCC2)C(C)=O)=N1 NMUQSBDHGNXUKW-UHFFFAOYSA-N 0.000 claims 1
- UNWSVMJDBKFGES-UHFFFAOYSA-N 2-(1-acetylpyrrolidin-2-yl)-n-[(2,3-dimethoxyphenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C2=C(C(=O)N(C)C(C3N(CCC3)C(C)=O)=N2)O)=C1OC UNWSVMJDBKFGES-UHFFFAOYSA-N 0.000 claims 1
- AIIQXBVWKSDGKV-UHFFFAOYSA-N 2-(1-acetylpyrrolidin-2-yl)-n-[(2-ethoxyphenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CCOC1=CC=CC=C1CNC(=O)C1=C(O)C(=O)N(C)C(C2N(CCC2)C(C)=O)=N1 AIIQXBVWKSDGKV-UHFFFAOYSA-N 0.000 claims 1
- BWOYEQBLDGFHHV-UHFFFAOYSA-N 2-(1-acetylpyrrolidin-2-yl)-n-[(4-fluoro-2-methylsulfonylphenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CC(=O)N1CCCC1C1=NC(C(=O)NCC=2C(=CC(F)=CC=2)S(C)(=O)=O)=C(O)C(=O)N1C BWOYEQBLDGFHHV-UHFFFAOYSA-N 0.000 claims 1
- SXBRRPCHWCRBGM-UHFFFAOYSA-N 2-(1-acetylpyrrolidin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CC(=O)N1CCCC1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C SXBRRPCHWCRBGM-UHFFFAOYSA-N 0.000 claims 1
- FHAGWXHXFUVYQQ-UHFFFAOYSA-N 2-(1-acetylpyrrolidin-2-yl)-n-[[2-(dimethylamino)phenyl]methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CN(C)C1=CC=CC=C1CNC(=O)C1=C(O)C(=O)N(C)C(C2N(CCC2)C(C)=O)=N1 FHAGWXHXFUVYQQ-UHFFFAOYSA-N 0.000 claims 1
- QRIHGCAEXUHLOW-UHFFFAOYSA-N 2-(1-benzoylpyrrolidin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C2N(CCC2)C(=O)C=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 QRIHGCAEXUHLOW-UHFFFAOYSA-N 0.000 claims 1
- RNIPBSWCXDEYGJ-UHFFFAOYSA-N 2-(1-ethyl-2,3-dihydroindol-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound C1C2=CC=CC=C2N(CC)C1C(N(C(=O)C=1O)C)=NC=1C(=O)NCC1=CC=C(F)C=C1 RNIPBSWCXDEYGJ-UHFFFAOYSA-N 0.000 claims 1
- DSYZHJDLBCRDPT-UHFFFAOYSA-N 2-(2,2-dimethoxyethyl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound O=C1N(C)C(CC(OC)OC)=NC(C(=O)NCC=2C=CC(F)=CC=2)=C1O DSYZHJDLBCRDPT-UHFFFAOYSA-N 0.000 claims 1
- RSNBQZPGNYQALO-UHFFFAOYSA-N 2-(2,3-dihydro-1h-indol-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C2NC3=CC=CC=C3C2)=NC=1C(=O)NCC1=CC=C(F)C=C1 RSNBQZPGNYQALO-UHFFFAOYSA-N 0.000 claims 1
- FGCQVGQJXOFNDP-UHFFFAOYSA-N 2-(2-acetamidopropan-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound O=C1N(C)C(C(C)(C)NC(=O)C)=NC(C(=O)NCC=2C=CC(F)=CC=2)=C1O FGCQVGQJXOFNDP-UHFFFAOYSA-N 0.000 claims 1
- VENKFOMMRMCXSN-UHFFFAOYSA-N 2-(3-acetyl-1,3-thiazolidin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CC(=O)N1CCSC1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C VENKFOMMRMCXSN-UHFFFAOYSA-N 0.000 claims 1
- NFEPQYVYHPMREC-UHFFFAOYSA-N 2-(4-acetyl-1,2-dimethylpiperazin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CN1CCN(C(C)=O)CC1(C)C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C NFEPQYVYHPMREC-UHFFFAOYSA-N 0.000 claims 1
- BMTUWFRODUAELZ-UHFFFAOYSA-N 2-(4-benzoyl-1-methylpiperazin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CN1CCN(C(=O)C=2C=CC=CC=2)CC1C(N(C(=O)C=1O)C)=NC=1C(=O)NCC1=CC=C(F)C=C1 BMTUWFRODUAELZ-UHFFFAOYSA-N 0.000 claims 1
- VWXCOJBXZNKXDR-HZPDHXFCSA-N 2-[(2r,4r)-1-acetyl-4-ethoxypyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CC(=O)N1C[C@H](OCC)C[C@@H]1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C VWXCOJBXZNKXDR-HZPDHXFCSA-N 0.000 claims 1
- KQGKCKYQHCMVBU-RTBURBONSA-N 2-[(2r,4r)-1-benzoyl-4-methoxypyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound N1([C@H](C[C@H](C1)OC)C=1N(C(=O)C(O)=C(C(=O)NCC=2C=CC(F)=CC=2)N=1)C)C(=O)C1=CC=CC=C1 KQGKCKYQHCMVBU-RTBURBONSA-N 0.000 claims 1
- GUPLVGUUZBBMSC-HUUCEWRRSA-N 2-[(2r,4r)-4-ethoxy-1-[2-(methylamino)-2-oxoacetyl]pyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CNC(=O)C(=O)N1C[C@H](OCC)C[C@@H]1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C GUPLVGUUZBBMSC-HUUCEWRRSA-N 0.000 claims 1
- JJMZDFZRSSKHCW-ZDUSSCGKSA-N 2-[(2s)-1-acetyl-4,4-difluoropyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CC(=O)N1CC(F)(F)C[C@H]1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C JJMZDFZRSSKHCW-ZDUSSCGKSA-N 0.000 claims 1
- GVFGHFHNEWIZGL-AWEZNQCLSA-N 2-[(2s)-1-acetylpyrrolidin-2-yl]-n-[(4-fluoro-2-methoxyphenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound COC1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N(C)C([C@H]2N(CCC2)C(C)=O)=N1 GVFGHFHNEWIZGL-AWEZNQCLSA-N 0.000 claims 1
- OLQXVJVOJZSEHE-HNNXBMFYSA-N 2-[(2s)-4,4-difluoro-1-(pyridazine-3-carbonyl)pyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C([C@H]2N(CC(F)(F)C2)C(=O)C=2N=NC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 OLQXVJVOJZSEHE-HNNXBMFYSA-N 0.000 claims 1
- VXMCFIODWHQIEV-INIZCTEOSA-N 2-[(2s)-4,4-difluoro-1-(pyridine-2-carbonyl)pyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C([C@H]2N(CC(F)(F)C2)C(=O)C=2N=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 VXMCFIODWHQIEV-INIZCTEOSA-N 0.000 claims 1
- WGVOGOWLJMYYJM-KGLIPLIRSA-N 2-[(2s,4r)-1-acetyl-4-hydroxypyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CC(=O)N1C[C@H](O)C[C@H]1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C WGVOGOWLJMYYJM-KGLIPLIRSA-N 0.000 claims 1
- FOSNNBJCOZOKQS-RTWAWAEBSA-N 2-[(2s,4r)-1-acetyl-4-phenylmethoxypyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C([C@@H]2C[C@H](CN2C(=O)C)OCC=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 FOSNNBJCOZOKQS-RTWAWAEBSA-N 0.000 claims 1
- MMUHCXFDVPIMLD-RPBOFIJWSA-N 2-[(2s,4r)-1-benzoyl-4-phenylmethoxypyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C([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 MMUHCXFDVPIMLD-RPBOFIJWSA-N 0.000 claims 1
- WBMNCNFOEYRXFC-KBPBESRZSA-N 2-[(2s,4s)-1-[2-(dimethylamino)-2-oxoacetyl]-4-fluoropyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CN(C)C(=O)C(=O)N1C[C@@H](F)C[C@H]1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C WBMNCNFOEYRXFC-KBPBESRZSA-N 0.000 claims 1
- NBBLWTOHJFZTMU-KBPBESRZSA-N 2-[(2s,4s)-1-acetyl-4-fluoropyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CC(=O)N1C[C@@H](F)C[C@H]1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C NBBLWTOHJFZTMU-KBPBESRZSA-N 0.000 claims 1
- MBSMKNIEBKYDJI-STQMWFEESA-N 2-[(2s,4s)-4-fluoro-1-methylpyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CN1C[C@@H](F)C[C@H]1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C MBSMKNIEBKYDJI-STQMWFEESA-N 0.000 claims 1
- MPSJYOCYFDZSFL-ZDUSSCGKSA-N 2-[(4r)-3-acetyl-1,3-thiazolidin-4-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CC(=O)N1CSC[C@H]1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C MPSJYOCYFDZSFL-ZDUSSCGKSA-N 0.000 claims 1
- LPAJVYWERLVLOW-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)pyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CN(C)S(=O)(=O)N1CCCC1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C LPAJVYWERLVLOW-UHFFFAOYSA-N 0.000 claims 1
- RFJKJXDRFILWJW-UHFFFAOYSA-N 2-[1-(ethylcarbamoyl)pyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CCNC(=O)N1CCCC1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C RFJKJXDRFILWJW-UHFFFAOYSA-N 0.000 claims 1
- YOHRQCNYRAVGRT-UHFFFAOYSA-N 2-[1-[2-(dimethylamino)acetyl]-2,3-dihydroindol-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound C1C2=CC=CC=C2N(C(=O)CN(C)C)C1C(N(C(=O)C=1O)C)=NC=1C(=O)NCC1=CC=C(F)C=C1 YOHRQCNYRAVGRT-UHFFFAOYSA-N 0.000 claims 1
- ARLFIGKAOGFDIQ-UHFFFAOYSA-N 2-[1-[2-(dimethylamino)acetyl]piperidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CN(C)CC(=O)N1CCCCC1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C ARLFIGKAOGFDIQ-UHFFFAOYSA-N 0.000 claims 1
- BQWBWHIWEZCEKG-UHFFFAOYSA-N 2-[1-benzoyl-4-(pyrazine-2-carbonyl)piperazin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C2N(CCN(C2)C(=O)C=2N=CC=NC=2)C(=O)C=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 BQWBWHIWEZCEKG-UHFFFAOYSA-N 0.000 claims 1
- UTJPUNPSZAIQOP-UHFFFAOYSA-N 2-[2-(4-benzoylpiperazin-1-yl)ethyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N(C)C=1CCN(CC1)CCN1C(=O)C1=CC=CC=C1 UTJPUNPSZAIQOP-UHFFFAOYSA-N 0.000 claims 1
- QBEHHCHEEFSDBW-UHFFFAOYSA-N 2-[4-(diethylaminomethyl)phenyl]-n-[(2,3-dimethoxyphenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound C1=CC(CN(CC)CC)=CC=C1C1=NC(C(=O)NCC=2C(=C(OC)C=CC=2)OC)=C(O)C(=O)N1C QBEHHCHEEFSDBW-UHFFFAOYSA-N 0.000 claims 1
- TTYMRCQTUGHFEE-UHFFFAOYSA-N 2-[4-(diethylaminomethyl)phenyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound C1=CC(CN(CC)CC)=CC=C1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C TTYMRCQTUGHFEE-UHFFFAOYSA-N 0.000 claims 1
- BMBDLWHCVPMPIC-UHFFFAOYSA-N 2-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2N(C(=O)C(O)=C(C(=O)NCC=3C=CC(F)=CC=3)N=2)C)C=C1 BMBDLWHCVPMPIC-UHFFFAOYSA-N 0.000 claims 1
- LOEDFWHPBPEHLI-UHFFFAOYSA-N 2-[4-[(dimethylamino)methyl]phenyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound C1=CC(CN(C)C)=CC=C1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C LOEDFWHPBPEHLI-UHFFFAOYSA-N 0.000 claims 1
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- NARKILMWEQIHTF-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-6-oxo-1-[[3-(pyrrolidin-1-ylmethyl)phenyl]methyl]pyrimidine-4-carboxamide Chemical compound O=C1C(O)=C(C(=O)NCC=2C=CC(F)=CC=2)N=CN1CC(C=1)=CC=CC=1CN1CCCC1 NARKILMWEQIHTF-UHFFFAOYSA-N 0.000 claims 1
- PTNYZJGTUPWTLH-UHFFFAOYSA-N n-[2-[4-[(4-fluoro-2-methylsulfonylphenyl)methylcarbamoyl]-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl]propan-2-yl]-n',n'-dimethyloxamide Chemical compound O=C1N(C)C(C(C)(C)NC(=O)C(=O)N(C)C)=NC(C(=O)NCC=2C(=CC(F)=CC=2)S(C)(=O)=O)=C1O PTNYZJGTUPWTLH-UHFFFAOYSA-N 0.000 claims 1
- WGLILLWPZIBWTQ-UHFFFAOYSA-N n-[2-[4-[(4-fluorophenyl)methylcarbamoyl]-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl]propan-2-yl]-n',n'-dimethyloxamide Chemical compound O=C1N(C)C(C(C)(C)NC(=O)C(=O)N(C)C)=NC(C(=O)NCC=2C=CC(F)=CC=2)=C1O WGLILLWPZIBWTQ-UHFFFAOYSA-N 0.000 claims 1
- NULNZGKAFCBDFD-UHFFFAOYSA-N n-[2-[4-[(4-fluorophenyl)methylcarbamoyl]-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl]propan-2-yl]imidazo[2,1-b][1,3]thiazole-6-carboxamide Chemical compound OC=1C(=O)N(C)C(C(C)(C)NC(=O)C=2N=C3SC=CN3C=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 NULNZGKAFCBDFD-UHFFFAOYSA-N 0.000 claims 1
- NGVSQIPBPYPCFN-UHFFFAOYSA-N n-[[4-fluoro-2-(trifluoromethyl)phenyl]methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound O=C1N(C)C=NC(C(=O)NCC=2C(=CC(F)=CC=2)C(F)(F)F)=C1O NGVSQIPBPYPCFN-UHFFFAOYSA-N 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 abstract 4
- 229940099797 HIV integrase inhibitor Drugs 0.000 abstract 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 2
- 229940088710 antibiotic agent Drugs 0.000 abstract 2
- 239000003084 hiv integrase inhibitor Substances 0.000 abstract 2
- 239000002955 immunomodulating agent Substances 0.000 abstract 2
- 229940121354 immunomodulator Drugs 0.000 abstract 2
- 239000004615 ingredient Substances 0.000 abstract 2
- 230000010076 replication Effects 0.000 abstract 2
- 229960005486 vaccine Drugs 0.000 abstract 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
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- Communicable Diseases (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33956801P | 2001-10-26 | 2001-10-26 | |
| US36219102P | 2002-03-06 | 2002-03-06 | |
| PCT/GB2002/004753 WO2003035077A1 (en) | 2001-10-26 | 2002-10-21 | N-substituted hydroxypyrimidinone carboxamide inhibitors of hiv integrase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME00427B true ME00427B (me) | 2011-10-10 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2008-637A ME00427B (me) | 2001-10-26 | 2002-10-21 | N-supstituisani hidroksipiramidinon karboksamidni inhibitori hiv integraze |
Country Status (34)
Families Citing this family (135)
| 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 |
| WO2002030931A2 (en) | 2000-10-12 | 2002-04-18 | Merck & Co., Inc. | Aza- and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| ATE364385T1 (de) | 2000-10-12 | 2007-07-15 | Merck & Co Inc | Aza- und polyaza-naphthalenylcarbonsäureamide als hiv-integrase-hemmer |
| EP1326610B1 (en) | 2000-10-12 | 2006-11-15 | Merck & Co., Inc. | Aza-and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| EP2181985B1 (en) | 2001-08-10 | 2011-10-26 | Shionogi & Co., Ltd. | Antiviral Agent |
| 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 |
| DK1441734T3 (da) * | 2001-10-26 | 2007-06-11 | Angeletti P Ist Richerche Bio | Dihydroxypyrimidin-carboxamid-inhibitorer a HIV-integrase |
| CA2463976C (en) * | 2001-10-26 | 2007-02-13 | Benedetta Crescenzi | N-substituted hydroxypyrimidinone carboxamide inhibitors of hiv integrase |
| US7009049B2 (en) | 2002-02-15 | 2006-03-07 | Cytokinetics, Inc. | Syntheses of quinazolinones |
| US7323460B2 (en) | 2002-03-15 | 2008-01-29 | Merck & Co., Inc. | N-(substituted benzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamides useful as HIV integrase inhibitors |
| US7214800B2 (en) | 2002-05-09 | 2007-05-08 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| US7166595B2 (en) | 2002-05-09 | 2007-01-23 | Cytokinetics, Inc. | Compounds, methods and compositions |
| AU2003231799A1 (en) * | 2002-05-23 | 2003-12-12 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| US7038048B2 (en) | 2002-05-23 | 2006-05-02 | Cytokinetics, Inc. | 3H-pyridopyrimidin-4-one compounds, compositions, and methods of their use |
| WO2004004657A2 (en) | 2002-07-09 | 2004-01-15 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| JP2006501201A (ja) | 2002-07-23 | 2006-01-12 | サイトキネティクス・インコーポレーテッド | 化合物、組成物および方法 |
| US7399763B2 (en) | 2002-09-11 | 2008-07-15 | Merck & Co., Inc. | 8-hydroxy-1-oxo-tetrahydropyrrolopyrazine compounds useful as HIV integrase inhibitors |
| JP2006506352A (ja) | 2002-09-11 | 2006-02-23 | 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ジヒドロキシピリドピラジン−1,6−ジオン化合物 |
| EP1558083A4 (en) | 2002-09-30 | 2008-04-16 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| KR20050087865A (ko) * | 2002-12-27 | 2005-08-31 | 이스티투토 디 리세르쉐 디 비올로지아 몰레콜라레 피. 안젤레티에스.피.에이. | HIV 인테그라제 억제제로서 유용한테트라하이드로-4H-피리도[1,2-a]피리미딘 및 관련화합물 |
| 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 |
| TW200510425A (en) | 2003-08-13 | 2005-03-16 | Japan Tobacco Inc | Nitrogen-containing fused ring compound and use thereof as HIV integrase inhibitor |
| WO2005041664A1 (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 |
| 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 |
| WO2005060654A2 (en) | 2003-12-19 | 2005-07-07 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| TW200526635A (en) * | 2003-12-22 | 2005-08-16 | Shionogi & Co | Hydroxypyrimidinone derivative having HIV integrase inhibitory activity |
| KR20060124701A (ko) * | 2004-01-12 | 2006-12-05 | 길리애드 사이언시즈, 인코포레이티드 | 피리미딜 포스포네이트 항바이러스성 화합물 및 그의 사용방법 |
| EP1725102A4 (en) * | 2004-03-09 | 2009-04-29 | Merck & Co Inc | HIV integrase |
| NZ549449A (en) * | 2004-03-09 | 2009-05-31 | Merck & Co Inc | HIV Integrase inhibitors |
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| CA2557926A1 (en) | 2004-03-09 | 2005-09-22 | Monica Donghi | Hiv integrase inhibitors |
| CN1964975B (zh) * | 2004-05-07 | 2011-11-30 | 默沙东公司 | Hiv整合酶抑制剂 |
| 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 |
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| US7173022B2 (en) | 2004-05-28 | 2007-02-06 | Bristol-Myers Squibb Company | Bicyclic heterocycles as HIV integrase inhibitors |
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