JP2008501018A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008501018A5 JP2008501018A5 JP2007515142A JP2007515142A JP2008501018A5 JP 2008501018 A5 JP2008501018 A5 JP 2008501018A5 JP 2007515142 A JP2007515142 A JP 2007515142A JP 2007515142 A JP2007515142 A JP 2007515142A JP 2008501018 A5 JP2008501018 A5 JP 2008501018A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- hydroxy
- methyl
- tetrahydro
- pyrimido
- 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
- XZEZILYZVNXRDA-UHFFFAOYSA-N 3-hydroxy-9,9-dimethyl-4-oxo-n-[[2-(2-oxoazetidin-1-yl)phenyl]methyl]-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=CC=C1N1CCC1=O XZEZILYZVNXRDA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 14
- 239000012453 solvate Substances 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- -1 dioxothiazinyl Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 239000003112 inhibitor Substances 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 239000003795 chemical substances by application Substances 0.000 claims 7
- 208000031886 HIV Infections Diseases 0.000 claims 6
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 claims 6
- 208000037357 HIV infectious disease Diseases 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 6
- 239000002777 nucleoside Substances 0.000 claims 6
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 6
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 208000030507 AIDS Diseases 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- HFHGVIBGEFYIFU-UHFFFAOYSA-N 3h-oxazepine-2-carboxamide Chemical compound NC(=O)N1CC=CC=CO1 HFHGVIBGEFYIFU-UHFFFAOYSA-N 0.000 claims 3
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims 3
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims 3
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 3
- 229940099797 HIV integrase inhibitor Drugs 0.000 claims 3
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims 3
- 230000034303 cell budding Effects 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 239000002835 hiv fusion inhibitor Substances 0.000 claims 3
- 239000003084 hiv integrase inhibitor Substances 0.000 claims 3
- 239000004030 hiv protease inhibitor Substances 0.000 claims 3
- 230000035800 maturation Effects 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- LDSKYBVNIGKJHA-UHFFFAOYSA-N 2h-1,4-oxazine-2-carboxamide Chemical compound NC(=O)C1OC=CN=C1 LDSKYBVNIGKJHA-UHFFFAOYSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- PYYHHGCMPCSNFK-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 PYYHHGCMPCSNFK-UHFFFAOYSA-N 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
- KATSFXHQLOKKKZ-UHFFFAOYSA-N 3-hydroxy-9,9-dimethyl-n-[(2-methylsulfonylphenyl)methyl]-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=CC=C1S(C)(=O)=O KATSFXHQLOKKKZ-UHFFFAOYSA-N 0.000 claims 1
- CKUVWMOMSIPZMI-UHFFFAOYSA-N 9,9-diethyl-n-[(4-fluoro-2-methylsulfonylphenyl)methyl]-3-hydroxy-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CCC1(CC)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1S(C)(=O)=O CKUVWMOMSIPZMI-UHFFFAOYSA-N 0.000 claims 1
- ZFGUMKBFKVQRLF-UHFFFAOYSA-N 9,9-diethyl-n-[[4-fluoro-2-(1,2,4-triazol-1-yl)phenyl]methyl]-3-hydroxy-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CCC1(CC)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1N1C=NC=N1 ZFGUMKBFKVQRLF-UHFFFAOYSA-N 0.000 claims 1
- UCULMFRTTVDHQW-UHFFFAOYSA-N 9,9-diethyl-n-[[4-fluoro-2-(methylcarbamoyl)phenyl]methyl]-3-hydroxy-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CCC1(CC)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1C(=O)NC UCULMFRTTVDHQW-UHFFFAOYSA-N 0.000 claims 1
- 229940122440 HIV protease inhibitor Drugs 0.000 claims 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- DWLVWMUCHSLGSU-UHFFFAOYSA-N dimethylcarbamic acid Chemical compound CN(C)C(O)=O DWLVWMUCHSLGSU-UHFFFAOYSA-N 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- ZHSFPAHDEUORJZ-UHFFFAOYSA-N n-[(2-acetamido-4-fluorophenyl)methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC(=O)NC1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N(CCOC2(C)C)C2=N1 ZHSFPAHDEUORJZ-UHFFFAOYSA-N 0.000 claims 1
- MENZFRBTQXJKDK-UHFFFAOYSA-N n-[(2-dimethoxyphosphoryl-4-fluorophenyl)methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound COP(=O)(OC)C1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N(CCOC2(C)C)C2=N1 MENZFRBTQXJKDK-UHFFFAOYSA-N 0.000 claims 1
- YHWFNVSJZVKCNP-UHFFFAOYSA-N n-[(4-fluoro-2-methylsulfonylphenyl)methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1S(C)(=O)=O YHWFNVSJZVKCNP-UHFFFAOYSA-N 0.000 claims 1
- XGMAGKLMXYOTEJ-UHFFFAOYSA-N n-[(4-fluoro-2-morpholin-4-ylphenyl)methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1N1CCOCC1 XGMAGKLMXYOTEJ-UHFFFAOYSA-N 0.000 claims 1
- GOEURYJGZXLMPA-UHFFFAOYSA-N n-[(4-fluoro-2-sulfamoylphenyl)methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1S(N)(=O)=O GOEURYJGZXLMPA-UHFFFAOYSA-N 0.000 claims 1
- LYTKZEQMSYFEPI-UHFFFAOYSA-N n-[[2-(dimethylsulfamoyl)-4-fluorophenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CN(C)S(=O)(=O)C1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N(CCOC2(C)C)C2=N1 LYTKZEQMSYFEPI-UHFFFAOYSA-N 0.000 claims 1
- STAJYGBIAZYIRP-UHFFFAOYSA-N n-[[2-(dimethylsulfamoyl)-4-fluorophenyl]methyl]-9,9-diethyl-3-hydroxy-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CCC1(CC)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1S(=O)(=O)N(C)C STAJYGBIAZYIRP-UHFFFAOYSA-N 0.000 claims 1
- LISWJAIKDPKEJR-UHFFFAOYSA-N n-[[2-[3-(dimethylcarbamoyl)-1,2,4-triazol-1-yl]-4-fluorophenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound N1=C(C(=O)N(C)C)N=CN1C1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N(CCOC2(C)C)C2=N1 LISWJAIKDPKEJR-UHFFFAOYSA-N 0.000 claims 1
- CSSGZDUICVWCPW-UHFFFAOYSA-N n-[[4-fluoro-2-(1,2,4-triazol-1-yl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1N1C=NC=N1 CSSGZDUICVWCPW-UHFFFAOYSA-N 0.000 claims 1
- FONCPLRXMYTFAG-UHFFFAOYSA-N n-[[4-fluoro-2-(1-methyltetrazol-5-yl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CN1N=NN=C1C1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N(CCOC2(C)C)C2=N1 FONCPLRXMYTFAG-UHFFFAOYSA-N 0.000 claims 1
- ZAQPIFMYOBOZNA-UHFFFAOYSA-N n-[[4-fluoro-2-(1h-pyrazol-5-yl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1C1=CC=NN1 ZAQPIFMYOBOZNA-UHFFFAOYSA-N 0.000 claims 1
- NTQJGIZIRNLSRZ-UHFFFAOYSA-N n-[[4-fluoro-2-(2-hydroxyethylcarbamoyl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1C(=O)NCCO NTQJGIZIRNLSRZ-UHFFFAOYSA-N 0.000 claims 1
- IDNNBICIBQJMKQ-UHFFFAOYSA-N n-[[4-fluoro-2-(2-oxo-1,3-oxazolidin-3-yl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1N1CCOC1=O IDNNBICIBQJMKQ-UHFFFAOYSA-N 0.000 claims 1
- ZAYNAGILDTUKKA-UHFFFAOYSA-N n-[[4-fluoro-2-(2-oxoazetidin-1-yl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1N1CCC1=O ZAYNAGILDTUKKA-UHFFFAOYSA-N 0.000 claims 1
- MWXPELHYKUPTBS-UHFFFAOYSA-N n-[[4-fluoro-2-(2-oxopiperidin-1-yl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1N1CCCCC1=O MWXPELHYKUPTBS-UHFFFAOYSA-N 0.000 claims 1
- YPGPHKYNAXOSJE-UHFFFAOYSA-N n-[[4-fluoro-2-(2-oxopyrrolidin-1-yl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1N1CCCC1=O YPGPHKYNAXOSJE-UHFFFAOYSA-N 0.000 claims 1
- ZGOIAZNKBHHQNV-UHFFFAOYSA-N n-[[4-fluoro-2-(3-methyl-1,2,4-triazol-1-yl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound N1=C(C)N=CN1C1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N(CCOC2(C)C)C2=N1 ZGOIAZNKBHHQNV-UHFFFAOYSA-N 0.000 claims 1
- RZIWEYKLLAQSEL-UHFFFAOYSA-N n-[[4-fluoro-2-(5-methyl-1,2,4-triazol-1-yl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1=NC=NN1C1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N(CCOC2(C)C)C2=N1 RZIWEYKLLAQSEL-UHFFFAOYSA-N 0.000 claims 1
- QOZUICSVLJMIDW-UHFFFAOYSA-N n-[[4-fluoro-2-(methylcarbamoyl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CNC(=O)C1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N(CCOC2(C)C)C2=N1 QOZUICSVLJMIDW-UHFFFAOYSA-N 0.000 claims 1
- PLWNJEHHXBQCHO-UHFFFAOYSA-N n-[[4-fluoro-2-(methylsulfamoyl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CNS(=O)(=O)C1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N(CCOC2(C)C)C2=N1 PLWNJEHHXBQCHO-UHFFFAOYSA-N 0.000 claims 1
- RQOGKHGPSHFOKR-UHFFFAOYSA-N n-[[4-fluoro-2-(morpholine-4-carbonyl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1C(=O)N1CCOCC1 RQOGKHGPSHFOKR-UHFFFAOYSA-N 0.000 claims 1
- XBNFBNRVYGOFOX-UHFFFAOYSA-N n-[[4-fluoro-2-(thiadiazol-4-yl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1C1=CSN=N1 XBNFBNRVYGOFOX-UHFFFAOYSA-N 0.000 claims 1
- BTXFIDOCDUUPLO-UHFFFAOYSA-N n-[[4-fluoro-2-[3-(4-methylpiperazine-1-carbonyl)-1,2,4-triazol-1-yl]phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound C1CN(C)CCN1C(=O)C1=NN(C=2C(=CC=C(F)C=2)CNC(=O)C2=C(C(=O)N3C(C(OCC3)(C)C)=N2)O)C=N1 BTXFIDOCDUUPLO-UHFFFAOYSA-N 0.000 claims 1
- QOIZCKSYIIKGTA-UHFFFAOYSA-N n-[[4-fluoro-2-[3-(morpholine-4-carbonyl)-1,2,4-triazol-1-yl]phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1N(N=1)C=NC=1C(=O)N1CCOCC1 QOIZCKSYIIKGTA-UHFFFAOYSA-N 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- XTNLCOVLKPNKNC-UHFFFAOYSA-N CC(C)(C1=NC(C(NCc(cc2)c(C)cc2F)=O)=C2O)OCCCN1C2=O Chemical compound CC(C)(C1=NC(C(NCc(cc2)c(C)cc2F)=O)=C2O)OCCCN1C2=O XTNLCOVLKPNKNC-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57551304P | 2004-05-28 | 2004-05-28 | |
| US60/575,513 | 2004-05-28 | ||
| US60337104P | 2004-08-20 | 2004-08-20 | |
| US60/603,371 | 2004-08-20 | ||
| US11/126,891 US7176196B2 (en) | 2004-05-28 | 2005-05-11 | Bicyclic heterocycles as HIV integrase inhibitors |
| US11/126,891 | 2005-05-11 | ||
| PCT/US2005/016473 WO2005118593A1 (en) | 2004-05-28 | 2005-05-12 | Bicyclic heterocycles as hiv integrase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008501018A JP2008501018A (ja) | 2008-01-17 |
| JP2008501018A5 true JP2008501018A5 (enExample) | 2008-06-19 |
| JP4874959B2 JP4874959B2 (ja) | 2012-02-15 |
Family
ID=35456854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007515142A Expired - Fee Related JP4874959B2 (ja) | 2004-05-28 | 2005-05-12 | Ｈｉｖインテグラーゼインヒビターとしての二環式ヘテロ環 |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US7176196B2 (enExample) |
| EP (1) | EP1749011B1 (enExample) |
| JP (1) | JP4874959B2 (enExample) |
| KR (1) | KR101097623B1 (enExample) |
| AR (1) | AR049124A1 (enExample) |
| AT (1) | ATE412656T1 (enExample) |
| AU (1) | AU2005250356C1 (enExample) |
| BR (1) | BRPI0511623A (enExample) |
| CA (1) | CA2568356C (enExample) |
| CY (1) | CY1110266T1 (enExample) |
| DE (1) | DE602005010690D1 (enExample) |
| DK (1) | DK1749011T3 (enExample) |
| ES (1) | ES2315875T3 (enExample) |
| HR (1) | HRP20090005T3 (enExample) |
| IL (1) | IL179455A (enExample) |
| MX (1) | MXPA06013835A (enExample) |
| NO (1) | NO20065879L (enExample) |
| NZ (1) | NZ551282A (enExample) |
| PE (1) | PE20060242A1 (enExample) |
| PL (1) | PL1749011T3 (enExample) |
| PT (1) | PT1749011E (enExample) |
| RS (1) | RS50700B (enExample) |
| RU (1) | RU2381228C2 (enExample) |
| SI (1) | SI1749011T1 (enExample) |
| TW (1) | TWI366567B (enExample) |
| WO (1) | WO2005118593A1 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7115601B2 (en) | 2004-05-18 | 2006-10-03 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| WO2006103399A1 (en) * | 2005-03-31 | 2006-10-05 | Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa | Hiv integrase inhibitors |
| US7494984B2 (en) * | 2005-08-31 | 2009-02-24 | Bristol-Myers Squibb Company | Substituted imidazo[1,2-a]pyrimidines as HIV viral DNA integrase inhibitors |
| JP5094725B2 (ja) * | 2005-10-04 | 2012-12-12 | イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・エルレ・エルレ | Ｈｉｖインテグラーゼ阻害剤 |
| US7902182B2 (en) * | 2005-11-16 | 2011-03-08 | 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 |
| WO2007064502A1 (en) * | 2005-12-01 | 2007-06-07 | Bristol-Myers Squibb Company | Forms of n-[(4-fluorophenyl)methyl]-4,6,7,9-tetrahydro-3-hydroxy-9,9-dimethyl-4-oxo-pyrimido[2,1-c][1,4]oxazine-2-carboxamide |
| US20070129379A1 (en) * | 2005-12-01 | 2007-06-07 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| WO2007143446A1 (en) * | 2006-05-30 | 2007-12-13 | Bristol-Myers Squibb Company | Spiro-condensed heterotricyclic compounds as hiv integrase inhibitors |
| US7893055B2 (en) * | 2006-06-28 | 2011-02-22 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| CA2657034A1 (en) * | 2006-07-19 | 2008-01-24 | University Of Georgia Research Foundation, Inc. | Pyridinone diketo acids: inhibitors of hiv replication in combination therapy |
| 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 |
| WO2009120841A1 (en) * | 2008-03-27 | 2009-10-01 | Bristol-Myers Squibb Company | Crystalline form of n-[[4-fluoro-2-(5-methyl-1h-1,2,4-triazol-1-yl)phenyl]methyl]-4,6,7,9-tetrahydro-3-hydroxy-9,9-dimethyl-4-oxo-pyrimido[2,1-c][1,4]oxazine-2-carboxamide, sodium salt monohydrate |
| EP2349276B1 (en) * | 2008-10-06 | 2019-11-27 | Merck Sharp & Dohme Corp. | Hiv integrase inhibitors |
| US8143244B2 (en) * | 2009-02-26 | 2012-03-27 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| WO2011045330A1 (en) | 2009-10-13 | 2011-04-21 | Tibotec Pharmaceuticals | Macrocyclic integrase inhibitors |
| US8383639B2 (en) | 2009-10-15 | 2013-02-26 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| SG181524A1 (en) | 2009-12-07 | 2012-07-30 | Univ Georgia | Pyridinone hydroxycyclopentyl carboxamides: hiv integrase inhibitors with therapeutic applications |
| EP3351249A1 (en) | 2010-01-27 | 2018-07-25 | VIIV Healthcare Company | Antiviral therapy |
| WO2011121105A1 (en) | 2010-04-02 | 2011-10-06 | Tibotec Pharmaceuticals | Macrocyclic integrase inhibitors |
| EP2593447B1 (de) | 2010-07-15 | 2016-08-17 | Bayer Intellectual Property GmbH | 3-pyridyl-heteroarylcarboxamidverbindungen als schädlingsbekämpfungsmittel |
| US8791108B2 (en) | 2011-08-18 | 2014-07-29 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| US9089574B2 (en) | 2011-11-30 | 2015-07-28 | Emory University | Antiviral JAK inhibitors useful in treating or preventing retroviral and other viral infections |
| EP2807149A2 (en) * | 2012-01-26 | 2014-12-03 | CRO Consulting Limited | Agents for treating neurodegenerative disorders |
| EP2931730B1 (en) | 2012-12-17 | 2019-08-07 | Merck Sharp & Dohme Corp. | 4-pyridinonetriazine derivatives as hiv integrase inhibitors |
| US9493479B2 (en) | 2013-04-16 | 2016-11-15 | Merck Sharp & Dohme Corp. | Substituted pyrido[1,2-a]pyrazines as HIV integrase inhibitors |
| SI2997033T1 (en) | 2013-05-17 | 2018-04-30 | Merck Sharp & Dohme Corp. | FUZYCLE TRICYCLE HETEROCYCLIC COMPOUNDS AS HIV INTEGRATED INHIBITORS |
| US9951079B2 (en) | 2013-06-13 | 2018-04-24 | Merck Sharp & Dohme Corp. | Fused tricyclic heterocyclic compounds as HIV integrase inhibitors |
| CA2924829C (en) | 2013-09-27 | 2019-10-29 | Merck Sharp & Dohme Corp. | Substituted quinolizine derivatives useful as hiv integrase inhibitors |
| 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 |
| EP3389380B1 (en) | 2015-12-15 | 2021-07-21 | 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 |
| WO2018102634A1 (en) | 2016-12-02 | 2018-06-07 | 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 |
| WO2021050555A1 (en) * | 2019-09-10 | 2021-03-18 | X-Chem, Inc. | Compositions and uses thereof |
| CN113912622B (zh) * | 2020-07-10 | 2023-12-01 | 上海纽思克生物科技有限公司 | 三环嘧啶酮类化合物、其制备方法、其组合物和用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5693641A (en) * | 1996-08-16 | 1997-12-02 | Berlex Laboratories Inc. | Bicyclic pyrimidine derivatives and their use as anti-coagulants |
| DE122009000048I1 (de) | 2001-10-26 | 2010-04-08 | Angeletti P Ist Richerche Bio | N-substituierte hydroxypyrimidinoncarboxamid-hemmer der hiv-integrase |
| CA2463975A1 (en) | 2001-10-26 | 2003-05-01 | Maria Emilia Di Francesco | Dihydroxypyrimidine carboxamide inhibitors of hiv integrase |
| US7094783B2 (en) * | 2002-06-26 | 2006-08-22 | Bristol-Myers Squibb Company | Bicyclic pyrimidinones as coagulation cascade inhibitors |
| WO2004058756A1 (en) | 2002-12-27 | 2004-07-15 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa | Tetrahydro-4h-pyrido[1,2-a]pyrimidines and related compounds useful as 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 |
| TW200526635A (en) | 2003-12-22 | 2005-08-16 | Shionogi & Co | Hydroxypyrimidinone derivative having HIV integrase inhibitory activity |
| BRPI0518741A2 (pt) | 2004-12-03 | 2008-12-02 | Merck & Co Inc | uso de uma combinaÇço de uma droga diretamente metabolizada por ugt1a1 ou um seu sal farmaceuticamente aceitÁvel e atazanavir ou um seu sal farmaceuticamente aceitÁvel, e, combinaÇço farmacÊutica para administraÇço oral a um mamÍfero |
| WO2006103399A1 (en) | 2005-03-31 | 2006-10-05 | Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa | Hiv integrase inhibitors |
-
2005
- 2005-05-11 US US11/126,891 patent/US7176196B2/en not_active Expired - Lifetime
- 2005-05-12 AT AT05750075T patent/ATE412656T1/de active
- 2005-05-12 CA CA2568356A patent/CA2568356C/en not_active Expired - Fee Related
- 2005-05-12 KR KR1020067027455A patent/KR101097623B1/ko not_active Expired - Fee Related
- 2005-05-12 JP JP2007515142A patent/JP4874959B2/ja not_active Expired - Fee Related
- 2005-05-12 PT PT05750075T patent/PT1749011E/pt unknown
- 2005-05-12 HR HR20090005T patent/HRP20090005T3/xx unknown
- 2005-05-12 PL PL05750075T patent/PL1749011T3/pl unknown
- 2005-05-12 RS RSP-2008/0569A patent/RS50700B/sr unknown
- 2005-05-12 SI SI200530481T patent/SI1749011T1/sl unknown
- 2005-05-12 BR BRPI0511623-6A patent/BRPI0511623A/pt not_active IP Right Cessation
- 2005-05-12 MX MXPA06013835A patent/MXPA06013835A/es active IP Right Grant
- 2005-05-12 RU RU2006146970/04A patent/RU2381228C2/ru not_active IP Right Cessation
- 2005-05-12 DK DK05750075T patent/DK1749011T3/da active
- 2005-05-12 ES ES05750075T patent/ES2315875T3/es not_active Expired - Lifetime
- 2005-05-12 NZ NZ551282A patent/NZ551282A/en not_active IP Right Cessation
- 2005-05-12 WO PCT/US2005/016473 patent/WO2005118593A1/en not_active Ceased
- 2005-05-12 EP EP05750075A patent/EP1749011B1/en not_active Expired - Lifetime
- 2005-05-12 AU AU2005250356A patent/AU2005250356C1/en not_active Ceased
- 2005-05-12 DE DE602005010690T patent/DE602005010690D1/de not_active Expired - Lifetime
- 2005-05-25 TW TW094117105A patent/TWI366567B/zh not_active IP Right Cessation
- 2005-05-27 AR ARP050102187A patent/AR049124A1/es not_active Application Discontinuation
- 2005-05-30 PE PE2005000602A patent/PE20060242A1/es not_active Application Discontinuation
-
2006
- 2006-08-16 US US11/505,149 patent/US7511037B2/en not_active Expired - Lifetime
- 2006-11-21 IL IL179455A patent/IL179455A/en not_active IP Right Cessation
- 2006-12-19 NO NO20065879A patent/NO20065879L/no not_active Application Discontinuation
-
2009
- 2009-01-19 CY CY20091100068T patent/CY1110266T1/el unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2006146970A (ru) | Бициклические гетероциклы и их применение в качестве ингибиторов вич интегразы | |
| JP2008526761A5 (enExample) | ||
| RU2009102278A (ru) | Модуляторы рецептора s1p для лечения рассеянного склероза | |
| RU2002133666A (ru) | Производные триазола | |
| RU2008109908A (ru) | Соединения и композиции в качестве ингибиторов протеинкиназы | |
| HRP20100247T1 (hr) | Inhibitori hiv integraze | |
| RU2008140940A (ru) | Производное триазола или его соль | |
| JP2010513319A5 (enExample) | ||
| JP2014500322A5 (enExample) | ||
| RU2010143319A (ru) | Бензопирановые и беноксепиновые ингибиторы рi3k и их применение | |
| JP2006515339A5 (enExample) | ||
| RU2008116581A (ru) | Сульфонамидные производные, как активаторы гликокиназы, применимые для лечения диабета типа 2 | |
| JP2004538259A5 (enExample) | ||
| TW200500367A (en) | Triazole compounds useful in therapy | |
| JP2018503661A5 (enExample) | ||
| RU2006125446A (ru) | Производные n-замещенного n-сульфониламиноциклопропана и их фармацевтическое применение | |
| JP2009501775A5 (enExample) | ||
| TW200631959A (en) | Process for {3-[2(R)-[(1R)-1-[3, 5-bis(trifluoromethyl)phenyl]ethoxy]-3(S)-(4-fluorophenyl)morpholin-4-yl]methyl}-5-oxo-4, 5-dihydro-[1, 2, 4]-triazol-1-yl}phosphonic acid | |
| RU2007106928A (ru) | Производные бензилтриазолона в качестве ненуклеозидных ингибиторов обратной транскриптазы | |
| FR2903405A1 (fr) | Composes a effet potentialisateur de l'activite de l'ethionamide et leurs applications | |
| JP2004525183A5 (enExample) | ||
| JP2007537287A5 (enExample) | ||
| US20060014740A1 (en) | Analogs exhibiting inhibition of cell proliferation, methods of making, and uses thereof | |
| JP2002512235A5 (enExample) | ||
| RU2426734C2 (ru) | Пиразолопиридины и их аналоги |