JP2001510831A5 - - Google Patents
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- JP2001510831A5 JP2001510831A5 JP2000504120A JP2000504120A JP2001510831A5 JP 2001510831 A5 JP2001510831 A5 JP 2001510831A5 JP 2000504120 A JP2000504120 A JP 2000504120A JP 2000504120 A JP2000504120 A JP 2000504120A JP 2001510831 A5 JP2001510831 A5 JP 2001510831A5
- Authority
- JP
- Japan
- Prior art keywords
- piperazinyl
- methoxypyrimidine
- methoxy
- pyrimidine
- chlorohydrate
- 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.)
- Pending
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- -1 amino, acetamido, nitro, methyl Chemical group 0.000 description 52
- 150000001875 compounds Chemical class 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 8
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 229910052717 sulfur Chemical group 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- XAEAFOPJORAPHJ-UHFFFAOYSA-N (2-hydroxyphenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)O)=N1 XAEAFOPJORAPHJ-UHFFFAOYSA-N 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- FTZPBBKANJNASG-UHFFFAOYSA-N [4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]-phenylmethanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2C=CC=CC=2)=N1 FTZPBBKANJNASG-UHFFFAOYSA-N 0.000 description 2
- ACNPUFRLGXYSCY-UHFFFAOYSA-N [4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]-thiophen-3-ylmethanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C2=CSC=C2)=N1 ACNPUFRLGXYSCY-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- NGWLNKFLKBEANP-UHFFFAOYSA-N furan-2-yl-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2OC=CC=2)=N1 NGWLNKFLKBEANP-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- XEHFVPPGVYDARR-UHFFFAOYSA-N (2-aminophenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)N)=N1 XEHFVPPGVYDARR-UHFFFAOYSA-N 0.000 description 1
- MMGIZPLGTZIQIX-UHFFFAOYSA-N (2-aminophenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone;hypochlorous acid Chemical compound ClO.COC1=CC=NC(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)N)=N1 MMGIZPLGTZIQIX-UHFFFAOYSA-N 0.000 description 1
- GGSGOXASLBKDOX-UHFFFAOYSA-N (2-chlorophenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)Cl)=N1 GGSGOXASLBKDOX-UHFFFAOYSA-N 0.000 description 1
- HOBCYLLZHTXYMO-UHFFFAOYSA-N (2-chlorophenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone hypochlorous acid Chemical compound ClO.ClC1=C(C(=O)N2CCN(CC2)C2=NC=CC(=N2)OC)C=CC=C1 HOBCYLLZHTXYMO-UHFFFAOYSA-N 0.000 description 1
- QUKFWFGKFSRPQY-UHFFFAOYSA-N (2-fluorophenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)F)=N1 QUKFWFGKFSRPQY-UHFFFAOYSA-N 0.000 description 1
- YUIMKLQZNGROIQ-UHFFFAOYSA-N (2-methoxyphenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)OC)=N1 YUIMKLQZNGROIQ-UHFFFAOYSA-N 0.000 description 1
- SYKJCEFDKJRZRV-UHFFFAOYSA-N (3-chloro-1-benzothiophen-2-yl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C2=C(C3=CC=CC=C3S2)Cl)=N1 SYKJCEFDKJRZRV-UHFFFAOYSA-N 0.000 description 1
- BCXZYTKAHHILHR-UHFFFAOYSA-N (3-chloro-1-benzothiophen-2-yl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone;hypochlorous acid Chemical compound ClO.COC1=CC=NC(N2CCN(CC2)C(=O)C2=C(C3=CC=CC=C3S2)Cl)=N1 BCXZYTKAHHILHR-UHFFFAOYSA-N 0.000 description 1
- UQRULFYBKXBQAL-UHFFFAOYSA-N (3-chlorophenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone;hypochlorous acid Chemical compound ClO.COC1=CC=NC(N2CCN(CC2)C(=O)C=2C=C(Cl)C=CC=2)=N1 UQRULFYBKXBQAL-UHFFFAOYSA-N 0.000 description 1
- AYTJYGWCGZPRQH-UHFFFAOYSA-N (3-chlorothiophen-2-yl)-[4-(4-ethoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound CCOC1=CC=NC(N2CCN(CC2)C(=O)C2=C(C=CS2)Cl)=N1 AYTJYGWCGZPRQH-UHFFFAOYSA-N 0.000 description 1
- WSXQBJJKNDACFV-UHFFFAOYSA-N (3-chlorothiophen-2-yl)-[4-(4-ethoxypyrimidin-2-yl)piperazin-1-yl]methanone;hypochlorous acid Chemical compound ClO.CCOC1=CC=NC(N2CCN(CC2)C(=O)C2=C(C=CS2)Cl)=N1 WSXQBJJKNDACFV-UHFFFAOYSA-N 0.000 description 1
- IKPTYEDWQZPHHD-UHFFFAOYSA-N (3-chlorothiophen-2-yl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C2=C(C=CS2)Cl)=N1 IKPTYEDWQZPHHD-UHFFFAOYSA-N 0.000 description 1
- IEKZYCVMHLVDDC-UHFFFAOYSA-N (3-chlorothiophen-2-yl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone;hypochlorous acid Chemical compound ClO.COC1=CC=NC(N2CCN(CC2)C(=O)C2=C(C=CS2)Cl)=N1 IEKZYCVMHLVDDC-UHFFFAOYSA-N 0.000 description 1
- QFVRBMCQVTUKJK-UHFFFAOYSA-N (3-chlorothiophen-2-yl)-[4-(4-propan-2-yloxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound CC(C)OC1=CC=NC(N2CCN(CC2)C(=O)C2=C(C=CS2)Cl)=N1 QFVRBMCQVTUKJK-UHFFFAOYSA-N 0.000 description 1
- XZRDDFNJOXKMSD-UHFFFAOYSA-N (3-chlorothiophen-2-yl)-[4-(4-propan-2-yloxypyrimidin-2-yl)piperazin-1-yl]methanone;hypochlorous acid Chemical compound ClO.CC(C)OC1=CC=NC(N2CCN(CC2)C(=O)C2=C(C=CS2)Cl)=N1 XZRDDFNJOXKMSD-UHFFFAOYSA-N 0.000 description 1
- UWODUYCDZAOEKF-UHFFFAOYSA-N (3-fluorophenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2C=C(F)C=CC=2)=N1 UWODUYCDZAOEKF-UHFFFAOYSA-N 0.000 description 1
- OTWCOUGCRXGZAO-UHFFFAOYSA-N (3-fluorophenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone;hypochlorous acid Chemical compound ClO.COC1=CC=NC(N2CCN(CC2)C(=O)C=2C=C(F)C=CC=2)=N1 OTWCOUGCRXGZAO-UHFFFAOYSA-N 0.000 description 1
- OOVZVMGFQBXADV-UHFFFAOYSA-N (3-fluorothiophen-2-yl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C2=C(C=CS2)F)=N1 OOVZVMGFQBXADV-UHFFFAOYSA-N 0.000 description 1
- XKPICPMDOYQGLN-UHFFFAOYSA-N (3-fluorothiophen-2-yl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone;hypochlorous acid Chemical compound ClO.COC1=CC=NC(N2CCN(CC2)C(=O)C2=C(C=CS2)F)=N1 XKPICPMDOYQGLN-UHFFFAOYSA-N 0.000 description 1
- GIOFVHWSBGMPJT-UHFFFAOYSA-N (3-methoxyphenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=CC(C(=O)N2CCN(CC2)C=2N=C(OC)C=CN=2)=C1 GIOFVHWSBGMPJT-UHFFFAOYSA-N 0.000 description 1
- WHWQXBUXEZELSM-UHFFFAOYSA-N (4-chlorophenyl)-[4-(4,4-dimethoxy-1h-pyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound C1=CC(OC)(OC)NC(N2CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)=N1 WHWQXBUXEZELSM-UHFFFAOYSA-N 0.000 description 1
- APLKSROKOVCWND-UHFFFAOYSA-N (4-chlorophenyl)-[4-(4,4-dimethoxy-1h-pyrimidin-2-yl)piperazin-1-yl]methanone;hypochlorous acid Chemical compound ClO.C1=CC(OC)(OC)NC(N2CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)=N1 APLKSROKOVCWND-UHFFFAOYSA-N 0.000 description 1
- COZIABXQRYUDTN-UHFFFAOYSA-N (4-chlorophenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)=N1 COZIABXQRYUDTN-UHFFFAOYSA-N 0.000 description 1
- ZVBNPNXVAJUCCS-UHFFFAOYSA-N (4-chlorophenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone;hypochlorous acid Chemical compound ClO.COC1=CC=NC(N2CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)=N1 ZVBNPNXVAJUCCS-UHFFFAOYSA-N 0.000 description 1
- YGFKQKNWPIFDAT-UHFFFAOYSA-N (4-fluorophenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2C=CC(F)=CC=2)=N1 YGFKQKNWPIFDAT-UHFFFAOYSA-N 0.000 description 1
- MCXVRWDYRKMOGQ-UHFFFAOYSA-N (4-fluorophenyl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone;hypochlorous acid Chemical compound ClO.COC1=CC=NC(N2CCN(CC2)C(=O)C=2C=CC(F)=CC=2)=N1 MCXVRWDYRKMOGQ-UHFFFAOYSA-N 0.000 description 1
- GWOPRVSTEXYZKZ-UHFFFAOYSA-N (4-fluorophenyl)-[4-(4-propan-2-yloxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound CC(C)OC1=CC=NC(N2CCN(CC2)C(=O)C=2C=CC(F)=CC=2)=N1 GWOPRVSTEXYZKZ-UHFFFAOYSA-N 0.000 description 1
- AWXPEJQUKNPBCE-UHFFFAOYSA-N (4-fluorophenyl)-[4-(4-propan-2-yloxypyrimidin-2-yl)piperazin-1-yl]methanone;hypochlorous acid Chemical compound ClO.CC(C)OC1=CC=NC(N2CCN(CC2)C(=O)C=2C=CC(F)=CC=2)=N1 AWXPEJQUKNPBCE-UHFFFAOYSA-N 0.000 description 1
- CVTVGRRTTYVCTR-UHFFFAOYSA-N (5-chlorothiophen-2-yl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2SC(Cl)=CC=2)=N1 CVTVGRRTTYVCTR-UHFFFAOYSA-N 0.000 description 1
- SBVQPYBMEXWNHB-UHFFFAOYSA-N (5-chlorothiophen-2-yl)-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone;hypochlorous acid Chemical compound ClO.COC1=CC=NC(N2CCN(CC2)C(=O)C=2SC(Cl)=CC=2)=N1 SBVQPYBMEXWNHB-UHFFFAOYSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- SZFDVODFRHIJMU-UHFFFAOYSA-N 1-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]-2-thiophen-2-ylethanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)CC=2SC=CC=2)=N1 SZFDVODFRHIJMU-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HTMSBDOORJXZBE-UHFFFAOYSA-N 1h-indol-2-yl-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2NC3=CC=CC=C3C=2)=N1 HTMSBDOORJXZBE-UHFFFAOYSA-N 0.000 description 1
- UQVWWXFAOMCPEW-UHFFFAOYSA-N 1h-indol-3-yl-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]methanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2C3=CC=CC=C3NC=2)=N1 UQVWWXFAOMCPEW-UHFFFAOYSA-N 0.000 description 1
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- AHBRLJHXVMDVPT-UHFFFAOYSA-N 2-(1-benzothiophen-3-yl)-1-[4-(4-methoxypyrimidin-2-yl)piperazin-1-yl]ethanone Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)CC=2C3=CC=CC=C3SC=2)=N1 AHBRLJHXVMDVPT-UHFFFAOYSA-N 0.000 description 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
- LNGCZSUOQHOGAY-UHFFFAOYSA-N 2-[4-(4-methoxypyrimidin-2-yl)piperazine-1-carbonyl]benzoic acid Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(O)=O)=N1 LNGCZSUOQHOGAY-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
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- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
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- 206010021118 Hypotonia Diseases 0.000 description 1
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| PCT/ES1998/000212 WO1999005121A1 (es) | 1997-07-21 | 1998-07-21 | Derivados de acil-piperazinil-pirimidinas, su preparacion y su aplicacion como medicamentos |
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| ES2167276B1 (es) * | 2000-10-20 | 2003-04-01 | Esteve Labor Dr | Nuevos derivados de cianoaril (o cianoheteroaril)-carbonil-piperazinil-pirimidinas, su preparacion y su aplicacion como medicamentos. |
| WO2002072548A2 (en) * | 2001-03-09 | 2002-09-19 | Ortho-Mcneil Pharmaceutical, Inc. | Heterocyclic compounds and their use as histamine h4 ligands. |
| US7390813B1 (en) * | 2001-12-21 | 2008-06-24 | Xenon Pharmaceuticals Inc. | Pyridylpiperazines and aminonicotinamides and their use as therapeutic agents |
| US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
| US7589199B2 (en) | 2002-06-12 | 2009-09-15 | Chemocentryx, Inc. | Substituted piperazines |
| DK1531822T3 (da) * | 2002-06-12 | 2009-12-07 | Chemocentryx Inc | 1-aryl-4-substituerede piperazin derivater til anvendelse som CCR1 antagonister til behandlingen af inflammation og immunforstyrrelser |
| US7842693B2 (en) * | 2002-06-12 | 2010-11-30 | Chemocentryx, Inc. | Substituted piperazines |
| MXPA04012959A (es) * | 2002-06-29 | 2005-05-16 | Zentaris Gmbh | Arilcarbonilpiperacinas y heteroarilcarbonilpiperacinas y su uso para tratamiento de enfermedades de tumor benigno y maligno. |
| US20040127395A1 (en) * | 2002-09-06 | 2004-07-01 | Desai Pragnya J. | Use of histamine H4 receptor modulators for the treatment of allergy and asthma |
| US7435831B2 (en) | 2004-03-03 | 2008-10-14 | Chemocentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
| AU2005219438B2 (en) | 2004-03-03 | 2011-02-17 | Chemocentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
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| WO2012027495A1 (en) | 2010-08-27 | 2012-03-01 | University Of The Pacific | Piperazinylpyrimidine analogues as protein kinase inhibitors |
| GB2497476B (en) * | 2010-09-06 | 2018-01-10 | Guangzhou Inst Biomed & Health | Amide Compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2535718A1 (fr) * | 1982-11-09 | 1984-05-11 | Sanofi Sa | (piperazinyl-1)-2 pyrimidines, leurs sels, procede pour leur preparation et compositions pharmaceutiques en contenant |
| US4547505A (en) * | 1983-03-25 | 1985-10-15 | Degussa Aktiengesellschaft | N-Phenyl-N-'-cycloalkylalkanoylpiperazine useful as analgetics and process for its production |
| EP0257102B1 (en) * | 1986-02-24 | 1997-11-19 | Mitsui Petrochemical Industries, Ltd. | Agents for treating neurophathy |
| FR2642759B1 (fr) * | 1989-02-09 | 1991-05-17 | Laboratorios Esteve Sa | Derives de pyrimidyl-piperazinyl-alkyl azoles avec activite anxiolytique et/ou tranquillisante |
| FR2672052B1 (fr) * | 1991-01-28 | 1995-05-24 | Esteve Labor Dr | Derives d'aryl (ou heteroaryl)-piperazinyl-alkyl-azoles, leur preparation et leur application en tant que medicaments. |
| GB9226610D0 (en) * | 1992-12-21 | 1993-02-17 | Smithkline Beecham Plc | Compounds |
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- 1998-07-21 JP JP2000504120A patent/JP2001510831A/ja active Pending
- 1998-07-21 WO PCT/ES1998/000212 patent/WO1999005121A1/es not_active Ceased
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- 1998-07-21 KR KR10-2000-7000602A patent/KR100514148B1/ko not_active Expired - Fee Related
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