JP2006513200A5 - - Google Patents
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- Publication number
- JP2006513200A5 JP2006513200A5 JP2004563339A JP2004563339A JP2006513200A5 JP 2006513200 A5 JP2006513200 A5 JP 2006513200A5 JP 2004563339 A JP2004563339 A JP 2004563339A JP 2004563339 A JP2004563339 A JP 2004563339A JP 2006513200 A5 JP2006513200 A5 JP 2006513200A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- hydroxy
- amino
- fluorobenzyl
- pyrido
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 58
- 150000001875 compounds Chemical class 0.000 claims 37
- 125000000623 heterocyclic group Chemical group 0.000 claims 31
- 125000001424 substituent group Chemical group 0.000 claims 23
- 125000003118 aryl group Chemical group 0.000 claims 22
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 21
- 229910052757 nitrogen Inorganic materials 0.000 claims 20
- -1 O—C 1-6 haloalkyl Chemical group 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 18
- 125000005842 heteroatom Chemical group 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 229910052717 sulfur Inorganic materials 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000002393 azetidinyl group Chemical group 0.000 claims 7
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 7
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims 7
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims 7
- 125000002757 morpholinyl group Chemical group 0.000 claims 7
- WBQCKUNNRLRPOG-UHFFFAOYSA-N n'-[2-[(4-fluorophenyl)methylcarbamoyl]-3-hydroxy-4-oxo-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepin-10-yl]-n,n,n'-trimethyloxamide Chemical compound CN(C)C(=O)C(=O)N(C)C1CCCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 WBQCKUNNRLRPOG-UHFFFAOYSA-N 0.000 claims 7
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 7
- 125000004193 piperazinyl group Chemical group 0.000 claims 7
- 125000003386 piperidinyl group Chemical group 0.000 claims 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 7
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 7
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- MCPXZOOZEBNEGJ-UHFFFAOYSA-N n'-[2-[(4-fluoro-3-methylphenyl)methylcarbamoyl]-3-hydroxy-4-oxo-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepin-10-yl]-n,n,n'-trimethyloxamide Chemical compound CN(C)C(=O)C(=O)N(C)C1CCCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C(C)=C1 MCPXZOOZEBNEGJ-UHFFFAOYSA-N 0.000 claims 6
- YLIYNHWYALYMOQ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-9-[methyl-(4-methylpiperazin-1-yl)sulfonylamino]-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound C1CN(C)CCN1S(=O)(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 YLIYNHWYALYMOQ-UHFFFAOYSA-N 0.000 claims 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- SJVFREKFBRXASI-UHFFFAOYSA-N n'-[2-[(4-fluoro-3-methylphenyl)methylcarbamoyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl]-n,n,n'-trimethyloxamide Chemical compound CN(C)C(=O)C(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C(C)=C1 SJVFREKFBRXASI-UHFFFAOYSA-N 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 125000004434 sulfur atom Chemical group 0.000 claims 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- GOIXPYWYXSSRFX-UHFFFAOYSA-N 9-[azetidin-1-ylsulfonyl(methyl)amino]-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound C1CCN1S(=O)(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 GOIXPYWYXSSRFX-UHFFFAOYSA-N 0.000 claims 4
- IUWUIPCTVGUKAL-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-9-[methyl(morpholin-4-ylsulfonyl)amino]-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound C1COCCN1S(=O)(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 IUWUIPCTVGUKAL-UHFFFAOYSA-N 0.000 claims 4
- PFFFBBACUGSVPN-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-9-[methyl-(2-methylsulfonylacetyl)amino]-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CS(=O)(=O)CC(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 PFFFBBACUGSVPN-UHFFFAOYSA-N 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- MCDBKPBDTVBVTL-UHFFFAOYSA-N 9-[dimethylsulfamoyl(methyl)amino]-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CN(C)S(=O)(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 MCDBKPBDTVBVTL-UHFFFAOYSA-N 0.000 claims 3
- 208000030507 AIDS Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 150000003857 carboxamides Chemical class 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- FHMHJNJYVZSGOD-UHFFFAOYSA-N n'-[2-[(3-chloro-4-methylphenyl)methylcarbamoyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl]-n,n,n'-trimethyloxamide Chemical compound CN(C)C(=O)C(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(C)C(Cl)=C1 FHMHJNJYVZSGOD-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 2
- JVANDLOBMHTTNX-UHFFFAOYSA-N 1h-azepine-2-carboxamide Chemical compound NC(=O)C1=CC=CC=CN1 JVANDLOBMHTTNX-UHFFFAOYSA-N 0.000 claims 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 2
- SJWPTLITARZLER-UHFFFAOYSA-N 9-[[2-(dimethylsulfamoyl)acetyl]-methylamino]-n-[(4-fluoro-3-methylphenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CN(C)S(=O)(=O)CC(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C(C)=C1 SJWPTLITARZLER-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 108010002459 HIV Integrase Proteins 0.000 claims 2
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- JSXNILPFJXRHHW-UHFFFAOYSA-N n'-[2-[(3-chloro-4-fluorophenyl)methylcarbamoyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl]-n,n,n'-trimethyloxamide Chemical compound CN(C)C(=O)C(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C(Cl)=C1 JSXNILPFJXRHHW-UHFFFAOYSA-N 0.000 claims 2
- QMHNSONWMFDIOU-UHFFFAOYSA-N n'-[2-[(3-chlorophenyl)methylcarbamoyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl]-n,n,n'-trimethyloxamide Chemical compound CN(C)C(=O)C(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=CC(Cl)=C1 QMHNSONWMFDIOU-UHFFFAOYSA-N 0.000 claims 2
- ZQDWKAJNPJBABY-UHFFFAOYSA-N n'-[2-[(4-fluorophenyl)methylcarbamoyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl]-n,n,n'-trimethyloxamide Chemical compound CN(C)C(=O)C(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 ZQDWKAJNPJBABY-UHFFFAOYSA-N 0.000 claims 2
- COUJNVGGWLUEHF-UHFFFAOYSA-N n'-[2-[(4-fluorophenyl)methylcarbamoyl]-3-hydroxy-8,8-dimethyl-4-oxo-7,9-dihydro-6h-pyrido[1,2-a]pyrimidin-9-yl]-n,n,n'-trimethyloxamide Chemical compound OC=1C(=O)N2CCC(C)(C)C(N(C)C(=O)C(=O)N(C)C)C2=NC=1C(=O)NCC1=CC=C(F)C=C1 COUJNVGGWLUEHF-UHFFFAOYSA-N 0.000 claims 2
- GJDMGRQVNYSRDY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-9-[methyl(pyrrolidin-1-ylsulfonyl)amino]-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound C1CCCN1S(=O)(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 GJDMGRQVNYSRDY-UHFFFAOYSA-N 0.000 claims 2
- 239000002777 nucleoside Substances 0.000 claims 2
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- QIHXGEQRGCOEMM-AWEZNQCLSA-N (7s)-7-[acetyl(methyl)amino]-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound C([C@@H](CN1C(=O)C=2O)N(C)C(C)=O)CC1=NC=2C(=O)NCC1=CC=C(F)C=C1 QIHXGEQRGCOEMM-AWEZNQCLSA-N 0.000 claims 1
- MTQOCISNPZBKSQ-NSHDSACASA-N (7s)-7-amino-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound C([C@@H](CN1C(=O)C=2O)N)CC1=NC=2C(=O)NCC1=CC=C(F)C=C1 MTQOCISNPZBKSQ-NSHDSACASA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- NGPDRSZWMWPTBP-UHFFFAOYSA-N 10-[dimethylsulfamoyl(methyl)amino]-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepine-2-carboxamide Chemical compound CN(C)S(=O)(=O)N(C)C1CCCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 NGPDRSZWMWPTBP-UHFFFAOYSA-N 0.000 claims 1
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- 125000000984 3-chloro-4-fluorobenzyl group Chemical group [H]C1=C(F)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- KXZVNZFIIHQAQF-UHFFFAOYSA-N 8-(dimethylamino)-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound C1C(N(C)C)CCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 KXZVNZFIIHQAQF-UHFFFAOYSA-N 0.000 claims 1
- XFHBIVGPLRBAGI-UHFFFAOYSA-N 9-(dimethylamino)-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CN(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 XFHBIVGPLRBAGI-UHFFFAOYSA-N 0.000 claims 1
- ONYXLWNBCJZASX-UHFFFAOYSA-N 9-[2-(dimethylamino)-2-oxoethyl]sulfanyl-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CN(C)C(=O)CSC1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 ONYXLWNBCJZASX-UHFFFAOYSA-N 0.000 claims 1
- AJENRBXNEGLXGD-UHFFFAOYSA-N 9-[2-(dimethylamino)-2-oxoethyl]sulfonyl-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CN(C)C(=O)CS(=O)(=O)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 AJENRBXNEGLXGD-UHFFFAOYSA-N 0.000 claims 1
- SMGFJDMYWUTTHJ-UHFFFAOYSA-N 9-[[2-(azetidin-1-yl)-2-oxoacetyl]-methylamino]-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound C1CCN1C(=O)C(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 SMGFJDMYWUTTHJ-UHFFFAOYSA-N 0.000 claims 1
- ZXQJTWTXOCFJMQ-UHFFFAOYSA-N 9-[[2-(dimethylamino)-2-oxoethyl]-(dimethylsulfamoyl)amino]-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CN(C)C(=O)CN(S(=O)(=O)N(C)C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 ZXQJTWTXOCFJMQ-UHFFFAOYSA-N 0.000 claims 1
- OLNJBJWOVXBQHQ-UHFFFAOYSA-N 9-[[2-(dimethylamino)acetyl]-methylamino]-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CN(C)CC(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 OLNJBJWOVXBQHQ-UHFFFAOYSA-N 0.000 claims 1
- GWNGYBCEAAVTML-UHFFFAOYSA-N 9-[[2-(dimethylsulfamoyl)-2-methylpropanoyl]-methylamino]-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CN(C)S(=O)(=O)C(C)(C)C(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 GWNGYBCEAAVTML-UHFFFAOYSA-N 0.000 claims 1
- ORPQEQRWRQNFIC-UHFFFAOYSA-N 9-[[2-(dimethylsulfamoyl)acetyl]-methylamino]-3-hydroxy-4-oxo-n-(quinolin-8-ylmethyl)-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound C1=CN=C2C(CNC(=O)C=3N=C4N(C(C=3O)=O)CCCC4N(C)C(=O)CS(=O)(=O)N(C)C)=CC=CC2=C1 ORPQEQRWRQNFIC-UHFFFAOYSA-N 0.000 claims 1
- UAKGCWPAZQCGTD-UHFFFAOYSA-N 9-[[2-(dimethylsulfamoyl)acetyl]-methylamino]-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CN(C)S(=O)(=O)CC(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 UAKGCWPAZQCGTD-UHFFFAOYSA-N 0.000 claims 1
- ALDPQVITKWVGGY-UHFFFAOYSA-N 9-[dimethylcarbamoyl(methyl)amino]-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CN(C)C(=O)N(C)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 ALDPQVITKWVGGY-UHFFFAOYSA-N 0.000 claims 1
- WUSAEZLOLJNLKB-UHFFFAOYSA-N 9-[dimethylsulfamoyl(ethyl)amino]-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CN(C)S(=O)(=O)N(CC)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 WUSAEZLOLJNLKB-UHFFFAOYSA-N 0.000 claims 1
- PWMKURIVHMYCAG-UHFFFAOYSA-N 9-[dimethylsulfamoyl(methyl)amino]-n-[[4-fluoro-2-(methylcarbamoyl)phenyl]methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CNC(=O)C1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N2CCCC(N(C)S(=O)(=O)N(C)C)C2=N1 PWMKURIVHMYCAG-UHFFFAOYSA-N 0.000 claims 1
- OKYXYASARDFEQV-UHFFFAOYSA-N 9-[ethyl-(2-methylsulfonylacetyl)amino]-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide Chemical compound CS(=O)(=O)CC(=O)N(CC)C1CCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 OKYXYASARDFEQV-UHFFFAOYSA-N 0.000 claims 1
- 229940122440 HIV protease inhibitor Drugs 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000005275 alkylenearyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 239000003443 antiviral agent Substances 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
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 239000004030 hiv protease inhibitor Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
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| AR046938A1 (es) * | 2003-12-12 | 2006-01-04 | Merck & Co Inc | Procedimiento para preparar hexahidropirimido[1,2-a]azepin-2-carboxilatos y compuetos similares |
| TW200526635A (en) * | 2003-12-22 | 2005-08-16 | Shionogi & Co | Hydroxypyrimidinone derivative having HIV integrase inhibitory activity |
| 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 |
| US7157447B2 (en) | 2004-05-28 | 2007-01-02 | Bristol-Myers Squibb Company | Bicyclic heterocycles as HIV integrase inhibitors |
| US7176196B2 (en) | 2004-05-28 | 2007-02-13 | 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 |
| US7192948B2 (en) * | 2004-05-28 | 2007-03-20 | Bristol-Myers Squibb Company | Bicyclic heterocycles as HIV integrase inhibitors |
| WO2006060225A2 (en) * | 2004-11-23 | 2006-06-08 | Merck & Co., Inc. | Process for asymmetric synthesis of hexahydropyrimido[1,2-a] azepine-2-carboxamides and related compounds |
| 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. |
| EP1819323B2 (en) * | 2004-12-03 | 2023-03-22 | Merck Sharp & Dohme Corp. | Pharmaceutical composition containing an anti-nucleating agent |
| UA87884C2 (uk) * | 2004-12-03 | 2009-08-25 | Мерк Энд Ко., Инк. | Безводна кристалічна калієва сіль інгібітора віл-інтегрази |
| 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 |
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| US7494984B2 (en) * | 2005-08-31 | 2009-02-24 | Bristol-Myers Squibb Company | Substituted imidazo[1,2-a]pyrimidines as HIV viral DNA integrase inhibitors |
| CA2622639C (en) * | 2005-10-04 | 2012-01-03 | Istituto Di Recerche Di Biologia Molecolare P. Angeletti S.P.A. | Hiv integrase inhibitors |
| 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 |
| EA200801144A1 (ru) | 2005-10-27 | 2008-10-30 | Сионоги Энд Ко., Лтд. | Полициклическое карбамоилпиридоновое производное, обладающее ингибиторной активностью в отношении интегразы вич |
| US7897592B2 (en) * | 2005-11-15 | 2011-03-01 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| WO2007058646A1 (en) * | 2005-11-15 | 2007-05-24 | Bristol-Myers Squibb Company | Hiv integrase inhibitors: cyclic pyrimidinone compounds |
| US7902182B2 (en) * | 2005-11-16 | 2011-03-08 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| US8039458B2 (en) * | 2005-11-17 | 2011-10-18 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| WO2007064316A1 (en) * | 2005-11-30 | 2007-06-07 | Bristol-Myers Squibb Company | Bicyclic heterocycles as hiv integrase inhibitors |
| US20070129379A1 (en) * | 2005-12-01 | 2007-06-07 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
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| US7897593B2 (en) | 2006-05-30 | 2011-03-01 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| US7893055B2 (en) * | 2006-06-28 | 2011-02-22 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| US7763630B2 (en) * | 2007-06-06 | 2010-07-27 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| US8129398B2 (en) * | 2008-03-19 | 2012-03-06 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| WO2010042392A2 (en) * | 2008-10-06 | 2010-04-15 | Merck & Co., Inc. | Hiv integrase inhibitors |
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| US8143244B2 (en) * | 2009-02-26 | 2012-03-27 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| BRPI1015943A8 (pt) * | 2009-07-02 | 2018-01-09 | Sanofi Sa | derivados de 1,2,3,4-tetra - hidro - pirimido {1,2-a} pirimidin-6-ona, o respectivo preparo e a respectiva utilização farmacêutica. |
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| IN2012DN03377A (https=) | 2009-10-26 | 2015-10-23 | Merck Sharp & Dohme | |
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| DK2790705T3 (en) | 2011-12-15 | 2018-03-12 | Novartis Ag | Use of inhibitors of the activity or function of PI3K |
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| 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 |
| MD4794B1 (ro) | 2013-09-27 | 2022-02-28 | Merck Sharp & Dohme Corp | Derivaţi de chinolizină substituiţi utili ca inhibitori de integrază HIV |
| WO2016187788A1 (en) | 2015-05-25 | 2016-12-01 | Merck Sharp & Dohme Corp. | Fused tricyclic heterocyclic compounds useful for treating hiv infection |
| 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 |
| WO2017113288A1 (en) | 2015-12-31 | 2017-07-06 | Merck Sharp & Dohme Corp. | Fused tricyclic heterocyclic compounds as hiv integrase inhibitors |
| US10934312B2 (en) | 2016-12-02 | 2021-03-02 | Merck Sharp & Dohme Corp. | Tricyclic heterocycle compounds useful as HIV integrase inhibitors |
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| US6380249B1 (en) | 1998-06-03 | 2002-04-30 | Merck & Co., Inc. | HIV integrase inhibitors |
| US6306891B1 (en) | 1998-06-03 | 2001-10-23 | Merck & Co., Inc. | HIV integrase inhibitors |
| US6262055B1 (en) | 1998-06-03 | 2001-07-17 | Merck & Co., Inc. | HIV integrase inhibitors |
| 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 |
| EP1289993B9 (en) * | 2000-06-07 | 2008-08-20 | Vertex Pharmaceuticals Incorporated | Caspase inhibitors and uses thereof |
| GB0017676D0 (en) * | 2000-07-19 | 2000-09-06 | Angeletti P Ist Richerche Bio | Inhibitors of viral polymerase |
| CA2321348A1 (en) * | 2000-09-27 | 2002-03-27 | Blaise Magloire N'zemba | Aromatic derivatives with hiv integrase inhibitory properties |
| 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 |
| CA2425440C (en) | 2000-10-12 | 2010-04-13 | Merck & Co., Inc. | Aza- and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| US6919351B2 (en) | 2000-10-12 | 2005-07-19 | 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 |
| 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 |
| EP1467970B1 (en) | 2002-01-17 | 2007-08-22 | Merck & Co., Inc. | Hydroxynaphthyridinone carboxamides useful as hiv integrase inhibitors |
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| US7037908B2 (en) | 2003-04-24 | 2006-05-02 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| AR046938A1 (es) * | 2003-12-12 | 2006-01-04 | Merck & Co Inc | Procedimiento para preparar hexahidropirimido[1,2-a]azepin-2-carboxilatos y compuetos similares |
-
2003
- 2003-12-18 EP EP03768014A patent/EP1578748B1/en not_active Expired - Lifetime
- 2003-12-18 AU AU2003292437A patent/AU2003292437A1/en not_active Abandoned
- 2003-12-18 AT AT03768014T patent/ATE481401T1/de not_active IP Right Cessation
- 2003-12-18 NZ NZ540729A patent/NZ540729A/en unknown
- 2003-12-18 WO PCT/GB2003/005543 patent/WO2004058757A1/en not_active Ceased
- 2003-12-18 MX MXPA05007010A patent/MXPA05007010A/es active IP Right Grant
- 2003-12-18 KR KR1020057012028A patent/KR20050087865A/ko not_active Ceased
- 2003-12-18 BR BR0317749-1A patent/BR0317749A/pt not_active IP Right Cessation
- 2003-12-18 PL PL377354A patent/PL377354A1/pl not_active Application Discontinuation
- 2003-12-18 US US10/540,449 patent/US7414045B2/en not_active Expired - Lifetime
- 2003-12-18 WO PCT/GB2003/005536 patent/WO2004058756A1/en not_active Ceased
- 2003-12-18 CN CNB2003801099211A patent/CN100343253C/zh not_active Expired - Fee Related
- 2003-12-18 JP JP2004563339A patent/JP4733986B2/ja not_active Expired - Fee Related
- 2003-12-18 HR HR20050593A patent/HRP20050593A2/hr not_active Application Discontinuation
- 2003-12-18 CA CA2509554A patent/CA2509554C/en not_active Expired - Fee Related
- 2003-12-18 DE DE60334248T patent/DE60334248D1/de not_active Expired - Lifetime
- 2003-12-18 AU AU2003292436A patent/AU2003292436B2/en not_active Ceased
- 2003-12-18 RU RU2005123807/04A patent/RU2329265C2/ru not_active IP Right Cessation
-
2005
- 2005-06-13 IS IS7892A patent/IS7892A/is unknown
- 2005-06-23 EC EC2005005890A patent/ECSP055890A/es unknown
- 2005-07-21 MA MA28407A patent/MA27583A1/fr unknown
- 2005-07-26 NO NO20053624A patent/NO20053624L/no not_active Application Discontinuation
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2008
- 2008-03-12 US US12/075,514 patent/US7968553B2/en not_active Expired - Lifetime
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