NO325206B1 - N-substituerte hydroksypyrimidinonkarboksamidinhibitorer for HIV-integrase, farmasoytiske preparater som omfatter slike forbindelser, og anvendelse av forbindelsene ved fremstilling av medikamenter mot HIV og AIDS. - Google Patents
N-substituerte hydroksypyrimidinonkarboksamidinhibitorer for HIV-integrase, farmasoytiske preparater som omfatter slike forbindelser, og anvendelse av forbindelsene ved fremstilling av medikamenter mot HIV og AIDS. Download PDFInfo
- Publication number
- NO325206B1 NO325206B1 NO20042165A NO20042165A NO325206B1 NO 325206 B1 NO325206 B1 NO 325206B1 NO 20042165 A NO20042165 A NO 20042165A NO 20042165 A NO20042165 A NO 20042165A NO 325206 B1 NO325206 B1 NO 325206B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- oxo
- hydroxy
- carboxamide
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 168
- -1 N-substituted hydroxypyrimidinone carboxamide Chemical class 0.000 title claims description 46
- 208000030507 AIDS Diseases 0.000 title claims description 16
- 239000003814 drug Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229940079593 drug Drugs 0.000 title claims description 3
- 239000003112 inhibitor Substances 0.000 title description 5
- 108010002459 HIV Integrase Proteins 0.000 title description 4
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000001424 substituent group Chemical group 0.000 claims description 171
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 96
- 125000005842 heteroatom Chemical group 0.000 claims description 82
- 125000000623 heterocyclic group Chemical group 0.000 claims description 78
- 229910052736 halogen Inorganic materials 0.000 claims description 73
- 150000002367 halogens Chemical class 0.000 claims description 72
- 229920006395 saturated elastomer Polymers 0.000 claims description 67
- 125000001072 heteroaryl group Chemical group 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 150000003839 salts Chemical class 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
- 125000004043 oxo group Chemical group O=* 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- 125000002619 bicyclic group Chemical group 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000002950 monocyclic group Chemical group 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 125000002837 carbocyclic group Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 238000011321 prophylaxis Methods 0.000 claims description 13
- MMPZNODECHHWIW-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-(4-methylmorpholin-3-yl)-6-oxopyrimidine-4-carboxamide Chemical compound CN1CCOCC1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C MMPZNODECHHWIW-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 9
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 208000015181 infectious disease Diseases 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- KICKGPQKASOONE-UHFFFAOYSA-N 2-(4-ethyl-1-methylpiperazin-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound C1N(CC)CCN(C)C1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C KICKGPQKASOONE-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 5
- KHJBWBNIGQBOFA-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-2-[1-(pyridine-2-carbonyl)-3,4-dihydro-2h-quinolin-2-yl]pyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C2N(C3=CC=CC=C3CC2)C(=O)C=2N=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 KHJBWBNIGQBOFA-UHFFFAOYSA-N 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 4
- ALTIACWYHGENDH-ZDUSSCGKSA-N 2-[(2s)-1-[2-(dimethylamino)-2-oxoacetyl]-4,4-difluoropyrrolidin-2-yl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound CN(C)C(=O)C(=O)N1CC(F)(F)C[C@H]1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C ALTIACWYHGENDH-ZDUSSCGKSA-N 0.000 claims description 4
- XWCKLKLAVPVPPD-MSOLQXFVSA-N 2-[(2s,4r)-1-benzoyl-4-hydroxypyrrolidin-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](O)C2)C(=O)C=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 XWCKLKLAVPVPPD-MSOLQXFVSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- OVRFHKWFMGUJFC-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound O=C1N(C)C=NC(C(=O)NCC=2C=CC(F)=CC=2)=C1O OVRFHKWFMGUJFC-UHFFFAOYSA-N 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 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 description 3
- 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 description 3
- GVTUUPQFRYGXMA-UHFFFAOYSA-N 2-(1-benzoyl-2,3-dihydroindol-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C2N(C3=CC=CC=C3C2)C(=O)C=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 GVTUUPQFRYGXMA-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- NGPNFONVUNXVEL-UHFFFAOYSA-N 2-[1-(dimethylamino)-2-phenylethyl]-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=1C(N(C)C)CC1=CC=CC=C1 NGPNFONVUNXVEL-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- KNIHLZWBFJLOPD-UHFFFAOYSA-N 2-[dimethylamino(phenyl)methyl]-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=1C(N(C)C)C1=CC=CC=C1 KNIHLZWBFJLOPD-UHFFFAOYSA-N 0.000 claims description 3
- JQIPHXBYCSUSNI-UHFFFAOYSA-N 4-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-2-n-(pyridin-2-ylmethyl)pyrimidine-2,4-dicarboxamide Chemical compound OC=1C(=O)N(C)C(C(=O)NCC=2N=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 JQIPHXBYCSUSNI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- QYJBDRMUCWAECJ-UHFFFAOYSA-N n-[(2,3-dimethoxyphenyl)methyl]-5-hydroxy-1-methyl-2-[4-(morpholin-4-ylmethyl)phenyl]-6-oxopyrimidine-4-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C2=C(C(=O)N(C)C(C=3C=CC(CN4CCOCC4)=CC=3)=N2)O)=C1OC QYJBDRMUCWAECJ-UHFFFAOYSA-N 0.000 claims description 3
- VZCYYKRGROYDTL-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-(2-hydroxy-3-morpholin-4-ylpropyl)-6-oxopyrimidine-4-carboxamide Chemical compound C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1CC(O)CN1CCOCC1 VZCYYKRGROYDTL-UHFFFAOYSA-N 0.000 claims description 3
- JDCVYDDPFWSXIY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-(1-methyl-3,4-dihydro-2h-quinolin-2-yl)-6-oxopyrimidine-4-carboxamide Chemical compound C1CC2=CC=CC=C2N(C)C1C(N(C(=O)C=1O)C)=NC=1C(=O)NCC1=CC=C(F)C=C1 JDCVYDDPFWSXIY-UHFFFAOYSA-N 0.000 claims description 3
- SCQMBPMJBXEQHB-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-(1-methyl-4-propan-2-ylsulfonylpiperazin-2-yl)-6-oxopyrimidine-4-carboxamide Chemical compound C1N(S(=O)(=O)C(C)C)CCN(C)C1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C SCQMBPMJBXEQHB-UHFFFAOYSA-N 0.000 claims description 3
- AHOZQSJDGWQTGZ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-(1-methylpiperazin-2-yl)-6-oxopyrimidine-4-carboxamide Chemical compound CN1CCNCC1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C AHOZQSJDGWQTGZ-UHFFFAOYSA-N 0.000 claims description 3
- HGPPRMHXEAZMCS-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-(1-methylpiperidin-2-yl)-6-oxopyrimidine-4-carboxamide Chemical compound CN1CCCCC1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C HGPPRMHXEAZMCS-UHFFFAOYSA-N 0.000 claims description 3
- VKPSGRZTOPVKNO-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-(1-methylsulfonylpyrrolidin-2-yl)-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C2N(CCC2)S(C)(=O)=O)=NC=1C(=O)NCC1=CC=C(F)C=C1 VKPSGRZTOPVKNO-UHFFFAOYSA-N 0.000 claims description 3
- XELOXWAFQQJLHA-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-(2-methyl-3,4-dihydro-1h-isoquinolin-3-yl)-6-oxopyrimidine-4-carboxamide Chemical compound CN1CC2=CC=CC=C2CC1C(N(C(=O)C=1O)C)=NC=1C(=O)NCC1=CC=C(F)C=C1 XELOXWAFQQJLHA-UHFFFAOYSA-N 0.000 claims description 3
- WHVOMNUJJHPZEB-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-(4-methylphenyl)-6-oxopyrimidine-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C WHVOMNUJJHPZEB-UHFFFAOYSA-N 0.000 claims description 3
- IEKQWIQTLCCVDM-UXHICEINSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-[(2s,4r)-1-methyl-4-phenylmethoxypyrrolidin-2-yl]-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C([C@@H]2C[C@H](CN2C)OCC=2C=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 IEKQWIQTLCCVDM-UXHICEINSA-N 0.000 claims description 3
- DXFBOOODWPDDKU-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-[1-(1-methylimidazole-2-carbonyl)pyrrolidin-2-yl]-6-oxopyrimidine-4-carboxamide Chemical compound CN1C=CN=C1C(=O)N1C(C=2N(C(=O)C(O)=C(C(=O)NCC=3C=CC(F)=CC=3)N=2)C)CCC1 DXFBOOODWPDDKU-UHFFFAOYSA-N 0.000 claims description 3
- IPNOUNCILQRZJN-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-[1-(1-oxidopyridin-1-ium-2-carbonyl)pyrrolidin-2-yl]-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C2N(CCC2)C(=O)C=2[N+](=CC=CC=2)[O-])=NC=1C(=O)NCC1=CC=C(F)C=C1 IPNOUNCILQRZJN-UHFFFAOYSA-N 0.000 claims description 3
- DTHZLIPXZZDEAW-VWNXMTODSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-2-[(2s,4r)-4-phenylmethoxy-1-(pyridine-2-carbonyl)pyrrolidin-2-yl]pyrimidine-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=2N=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 DTHZLIPXZZDEAW-VWNXMTODSA-N 0.000 claims description 3
- FMLGYBYNMDDGBV-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-2-[1-(pyridine-2-carbonyl)-2,3-dihydroindol-2-yl]pyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C2N(C3=CC=CC=C3C2)C(=O)C=2N=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 FMLGYBYNMDDGBV-UHFFFAOYSA-N 0.000 claims description 3
- BCCKQMVHHMROSZ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-2-[1-(pyridine-2-carbonyl)pyrrolidin-2-yl]pyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C2N(CCC2)C(=O)C=2N=CC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 BCCKQMVHHMROSZ-UHFFFAOYSA-N 0.000 claims description 3
- DKAPDWBJGOHKGB-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-2-[1-(pyridine-3-carbonyl)pyrrolidin-2-yl]pyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C2N(CCC2)C(=O)C=2C=NC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 DKAPDWBJGOHKGB-UHFFFAOYSA-N 0.000 claims description 3
- ROOWWHJTOPZXFJ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-2-[1-(pyridine-4-carbonyl)pyrrolidin-2-yl]pyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C2N(CCC2)C(=O)C=2C=CN=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 ROOWWHJTOPZXFJ-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- CZFFBEXEKNGXKS-UHFFFAOYSA-N raltegravir Chemical compound O1C(C)=NN=C1C(=O)NC(C)(C)C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C CZFFBEXEKNGXKS-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 2
- 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 description 2
- HBODMPJFESBLQE-UHFFFAOYSA-N 1-[[3-[(dimethylamino)methyl]phenyl]methyl]-n-[(4-fluorophenyl)methyl]-5-hydroxy-6-oxopyrimidine-4-carboxamide Chemical compound CN(C)CC1=CC=CC(CN2C(C(O)=C(C(=O)NCC=3C=CC(F)=CC=3)N=C2)=O)=C1 HBODMPJFESBLQE-UHFFFAOYSA-N 0.000 claims description 2
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- DVTFIKHECBTSFC-UHFFFAOYSA-N methyl 5-benzoyloxy-1-methyl-6-oxo-2-[1-(pyridine-2-carbonyl)-3,4-dihydro-2h-quinolin-2-yl]pyrimidine-4-carboxylate Chemical compound CN1C(=O)C(OC(=O)C=2C=CC=CC=2)=C(C(=O)OC)N=C1C1CCC2=CC=CC=C2N1C(=O)C1=CC=CC=N1 DVTFIKHECBTSFC-UHFFFAOYSA-N 0.000 description 1
- GBJRHCBFWYGWNQ-UHFFFAOYSA-N methyl 5-benzoyloxy-1-methyl-6-oxo-2-[2-(phenylmethoxycarbonylamino)propan-2-yl]pyrimidine-4-carboxylate Chemical compound COC(=O)C=1N=C(C(C)(C)NC(=O)OCC=2C=CC=CC=2)N(C)C(=O)C=1OC(=O)C1=CC=CC=C1 GBJRHCBFWYGWNQ-UHFFFAOYSA-N 0.000 description 1
- VIMNXOVYNCDMCB-UHFFFAOYSA-N methyl 5-benzoyloxy-1-methyl-6-oxo-2-pyrrolidin-2-ylpyrimidine-4-carboxylate Chemical compound CN1C(=O)C(OC(=O)C=2C=CC=CC=2)=C(C(=O)OC)N=C1C1CCCN1 VIMNXOVYNCDMCB-UHFFFAOYSA-N 0.000 description 1
- KEEUHMLRKZXAEX-UHFFFAOYSA-N methyl 5-benzoyloxy-2-(2,2-dimethoxyethyl)-1-methyl-6-oxopyrimidine-4-carboxylate Chemical compound O=C1N(C)C(CC(OC)OC)=NC(C(=O)OC)=C1OC(=O)C1=CC=CC=C1 KEEUHMLRKZXAEX-UHFFFAOYSA-N 0.000 description 1
- SRGYDAXUMYGKET-UHFFFAOYSA-N methyl 5-benzoyloxy-2-(2,3-dihydro-1h-indol-2-yl)-1-methyl-6-oxopyrimidine-4-carboxylate Chemical compound COC(=O)C=1N=C(C2NC3=CC=CC=C3C2)N(C)C(=O)C=1OC(=O)C1=CC=CC=C1 SRGYDAXUMYGKET-UHFFFAOYSA-N 0.000 description 1
- XSONXZYMUWRHMW-RPBOFIJWSA-N methyl 5-benzoyloxy-2-[(2s,4r)-1-benzoyl-4-phenylmethoxypyrrolidin-2-yl]-1-methyl-6-oxopyrimidine-4-carboxylate Chemical compound C([C@@H](C[C@H]1C2=NC(=C(C(=O)N2C)OC(=O)C=2C=CC=CC=2)C(=O)OC)OCC=2C=CC=CC=2)N1C(=O)C1=CC=CC=C1 XSONXZYMUWRHMW-RPBOFIJWSA-N 0.000 description 1
- FJDBKOIZVMMARN-UXHICEINSA-N methyl 5-benzoyloxy-2-[(2s,4r)-4-methoxy-1-phenylmethoxycarbonylpyrrolidin-2-yl]-1-methyl-6-oxopyrimidine-4-carboxylate Chemical compound N1([C@@H](C[C@H](C1)OC)C=1N(C(=O)C(OC(=O)C=2C=CC=CC=2)=C(C(=O)OC)N=1)C)C(=O)OCC1=CC=CC=C1 FJDBKOIZVMMARN-UXHICEINSA-N 0.000 description 1
- QZNAOLMQVYKMFD-UHFFFAOYSA-N methyl 5-benzoyloxy-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]-4-oxo-1h-pyrimidine-6-carboxylate Chemical compound COC(=O)C1=NC(C2N(CCC2)C(=O)OC(C)(C)C)=NC(O)=C1OC(=O)C1=CC=CC=C1 QZNAOLMQVYKMFD-UHFFFAOYSA-N 0.000 description 1
- GXVPHPOAYVJOLB-UHFFFAOYSA-N methyl 5-hydroxy-4-oxo-1h-pyrimidine-6-carboxylate Chemical compound COC(=O)C1=NC=NC(O)=C1O GXVPHPOAYVJOLB-UHFFFAOYSA-N 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
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- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- DWNWXQVKMRJASU-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-[2-[(2-morpholin-4-yl-2-oxoacetyl)amino]propan-2-yl]-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C(C)(C)NC(=O)C(=O)N2CCOCC2)=NC=1C(=O)NCC1=CC=C(F)C=C1 DWNWXQVKMRJASU-UHFFFAOYSA-N 0.000 description 1
- LGPINXWKVBCQRV-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-[4-(morpholin-4-ylmethyl)phenyl]-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C=2C=CC(CN3CCOCC3)=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 LGPINXWKVBCQRV-UHFFFAOYSA-N 0.000 description 1
- FAQIGTGQCLFKIU-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-morpholin-3-yl-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(C2NCCOC2)=NC=1C(=O)NCC1=CC=C(F)C=C1 FAQIGTGQCLFKIU-UHFFFAOYSA-N 0.000 description 1
- NTPGQOSRPGSHTJ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-2-(2-oxoethyl)pyrimidine-4-carboxamide Chemical compound O=C1N(C)C(CC=O)=NC(C(=O)NCC=2C=CC(F)=CC=2)=C1O NTPGQOSRPGSHTJ-UHFFFAOYSA-N 0.000 description 1
- IFYDWYVPVAMGRO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]tetradecanamide Chemical compound CCCCCCCCCCCCCC(=O)NCCCN(C)C IFYDWYVPVAMGRO-UHFFFAOYSA-N 0.000 description 1
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- 239000007922 nasal spray Substances 0.000 description 1
- QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 description 1
- 229960000884 nelfinavir Drugs 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
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- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
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- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- VUNXBQRNMNVUMV-UHFFFAOYSA-N phenyl(piperazin-1-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)N1CCNCC1 VUNXBQRNMNVUMV-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical compound OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 description 1
- 108700004029 pol Genes Proteins 0.000 description 1
- 101150088264 pol gene Proteins 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
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- 239000003223 protective agent Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
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- NUMIITGLIZNJIC-UHFFFAOYSA-N tert-butyl 2-[(z)-n'-hydroxycarbamimidoyl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1C(N)=NO NUMIITGLIZNJIC-UHFFFAOYSA-N 0.000 description 1
- MDMSZBHMBCNYNO-UHFFFAOYSA-N tert-butyl 2-cyanopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1C#N MDMSZBHMBCNYNO-UHFFFAOYSA-N 0.000 description 1
- MCSBQUCETYKRME-UHFFFAOYSA-N tert-butyl 3-(5-benzoyloxy-4-methoxy-6-methoxycarbonylpyrimidin-2-yl)morpholine-4-carboxylate Chemical compound COC(=O)C1=NC(C2N(CCOC2)C(=O)OC(C)(C)C)=NC(OC)=C1OC(=O)C1=CC=CC=C1 MCSBQUCETYKRME-UHFFFAOYSA-N 0.000 description 1
- LZHCFNBKMAWVPR-UHFFFAOYSA-N tert-butyl 3-(5-benzoyloxy-4-methoxycarbonyl-1-methyl-6-oxopyrimidin-2-yl)morpholine-4-carboxylate Chemical compound CN1C(=O)C(OC(=O)C=2C=CC=CC=2)=C(C(=O)OC)N=C1C1COCCN1C(=O)OC(C)(C)C LZHCFNBKMAWVPR-UHFFFAOYSA-N 0.000 description 1
- IPPMOUVOYGDPJP-UHFFFAOYSA-N tert-butyl 3-(5-benzoyloxy-6-methoxycarbonyl-4-oxo-1h-pyrimidin-2-yl)morpholine-4-carboxylate Chemical compound COC(=O)C1=NC(C2N(CCOC2)C(=O)OC(C)(C)C)=NC(O)=C1OC(=O)C1=CC=CC=C1 IPPMOUVOYGDPJP-UHFFFAOYSA-N 0.000 description 1
- MTAIAOFUTBJABI-UHFFFAOYSA-N tert-butyl 3-(5-hydroxy-6-methoxycarbonyl-4-oxo-1h-pyrimidin-2-yl)morpholine-4-carboxylate Chemical compound OC1=C(O)C(C(=O)OC)=NC(C2N(CCOC2)C(=O)OC(C)(C)C)=N1 MTAIAOFUTBJABI-UHFFFAOYSA-N 0.000 description 1
- JHNBDFZBWYOJPY-UHFFFAOYSA-N tert-butyl 3-(n'-hydroxycarbamimidoyl)morpholine-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOCC1\C(N)=N\O JHNBDFZBWYOJPY-UHFFFAOYSA-N 0.000 description 1
- AMDFBQXRVZTTKM-UHFFFAOYSA-N tert-butyl 3-carbamoylmorpholine-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOCC1C(N)=O AMDFBQXRVZTTKM-UHFFFAOYSA-N 0.000 description 1
- QSBSEJKNKHZYKD-UHFFFAOYSA-N tert-butyl 3-cyanomorpholine-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOCC1C#N QSBSEJKNKHZYKD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
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- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
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
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- 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
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- A61P37/00—Drugs for immunological or allergic disorders
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- 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
-
- 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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- 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
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- 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
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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
- C07D403/14—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
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- 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
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- 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
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- 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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PCT/GB2002/004753 WO2003035077A1 (en) | 2001-10-26 | 2002-10-21 | N-substituted hydroxypyrimidinone carboxamide inhibitors of hiv integrase |
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NO20042165L NO20042165L (no) | 2004-05-25 |
NO325206B1 true NO325206B1 (no) | 2008-02-25 |
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Application Number | Title | Priority Date | Filing Date |
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NO20042165A NO325206B1 (no) | 2001-10-26 | 2004-05-25 | N-substituerte hydroksypyrimidinonkarboksamidinhibitorer for HIV-integrase, farmasoytiske preparater som omfatter slike forbindelser, og anvendelse av forbindelsene ved fremstilling av medikamenter mot HIV og AIDS. |
NO2008007C NO2008007I1 (no) | 2001-10-26 | 2008-06-06 | Raltegravir eller et farmasoytisk akseptabelt saltderav, spesielt kaliumsaltet |
NO2020026C NO2020026I1 (no) | 2001-10-26 | 2020-08-10 | Raltegravir eller et farmasøytisk akseptabelt salt derav, spesielt kaliumsaltet |
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NO2008007C NO2008007I1 (no) | 2001-10-26 | 2008-06-06 | Raltegravir eller et farmasoytisk akseptabelt saltderav, spesielt kaliumsaltet |
NO2020026C NO2020026I1 (no) | 2001-10-26 | 2020-08-10 | Raltegravir eller et farmasøytisk akseptabelt salt derav, spesielt kaliumsaltet |
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