JP2006504714A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2006504714A5 JP2006504714A5 JP2004541111A JP2004541111A JP2006504714A5 JP 2006504714 A5 JP2006504714 A5 JP 2006504714A5 JP 2004541111 A JP2004541111 A JP 2004541111A JP 2004541111 A JP2004541111 A JP 2004541111A JP 2006504714 A5 JP2006504714 A5 JP 2006504714A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazol
- ylmethyl
- alkyl
- pyridazine
- fluoro
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 42
- 229910052736 halogen Inorganic materials 0.000 claims 22
- 150000002367 halogens Chemical class 0.000 claims 21
- -1 nitro, cyano, amino Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 16
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 13
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 102000005962 receptors Human genes 0.000 claims 11
- 108020003175 receptors Proteins 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 230000036506 anxiety Effects 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 238000001525 receptor binding assay Methods 0.000 claims 3
- 208000019116 sleep disease Diseases 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- RUAJXDPCBSTFRM-UHFFFAOYSA-N 3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-4-propyl-6-pyrimidin-2-ylpyridazine Chemical compound CCCC1=CC(C=2N=CC=CN=2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=N1 RUAJXDPCBSTFRM-UHFFFAOYSA-N 0.000 claims 2
- 208000000044 Amnesia Diseases 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 150000005215 alkyl ethers Chemical class 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 230000007831 electrophysiology Effects 0.000 claims 2
- 238000002001 electrophysiology Methods 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- QWLRJSGZNUOFFH-UHFFFAOYSA-N 1-[5-ethyl-6-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]pyridazin-3-yl]piperidin-4-ol Chemical compound CCC1=CC(N2CCC(O)CC2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=C1 QWLRJSGZNUOFFH-UHFFFAOYSA-N 0.000 claims 1
- RQQZYTLGTPFWTN-UHFFFAOYSA-N 1-[6-[[2-(3-chloro-2,6-difluorophenyl)imidazol-1-yl]methyl]-5-methoxypyridazin-3-yl]ethanone Chemical compound COC1=CC(C(C)=O)=NN=C1CN1C(C=2C(=C(Cl)C=CC=2F)F)=NC=C1 RQQZYTLGTPFWTN-UHFFFAOYSA-N 0.000 claims 1
- YDQYUOBULGEHLF-UHFFFAOYSA-N 1-[6-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propylpyridazin-3-yl]ethanone Chemical compound CCCC1=CC(C(C)=O)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 YDQYUOBULGEHLF-UHFFFAOYSA-N 0.000 claims 1
- QIAFESKFECMFQS-UHFFFAOYSA-N 2-[5-ethyl-6-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]pyridazin-3-yl]-1,3-thiazole Chemical compound CCC1=CC(C=2SC=CN=2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=C1 QIAFESKFECMFQS-UHFFFAOYSA-N 0.000 claims 1
- SFKBLJSNVUGLKL-UHFFFAOYSA-N 2-[5-ethyl-6-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]pyridazin-3-yl]-1,3-thiazole Chemical compound CCC1=CC(C=2SC=CN=2)=NN=C1CN1C=CN=C1C1=NC=CC=C1F SFKBLJSNVUGLKL-UHFFFAOYSA-N 0.000 claims 1
- KJJBBNHTSNMNAY-UHFFFAOYSA-N 2-[5-ethyl-6-[[2-(5-fluoro-2-methylphenyl)imidazol-1-yl]methyl]pyridazin-3-yl]-1,3-thiazole Chemical compound CCC1=CC(C=2SC=CN=2)=NN=C1CN1C=CN=C1C1=CC(F)=CC=C1C KJJBBNHTSNMNAY-UHFFFAOYSA-N 0.000 claims 1
- JUVWXZDKVFTONQ-UHFFFAOYSA-N 2-[5-ethyl-6-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]pyridazin-3-yl]-1,3-thiazole Chemical compound CCC1=CC(C=2SC=CN=2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=N1 JUVWXZDKVFTONQ-UHFFFAOYSA-N 0.000 claims 1
- FKTVSENZUYNFPF-UHFFFAOYSA-N 2-[6-[[2-(2,3-difluorophenyl)imidazol-1-yl]methyl]-5-ethylpyridazin-3-yl]-1,3-thiazole Chemical compound CCC1=CC(C=2SC=CN=2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=C1F FKTVSENZUYNFPF-UHFFFAOYSA-N 0.000 claims 1
- GCLRPGMGLKHDFO-UHFFFAOYSA-N 2-[6-[[2-(2,5-difluorophenyl)imidazol-1-yl]methyl]-5-ethylpyridazin-3-yl]-1,3-thiazole Chemical compound CCC1=CC(C=2SC=CN=2)=NN=C1CN1C=CN=C1C1=CC(F)=CC=C1F GCLRPGMGLKHDFO-UHFFFAOYSA-N 0.000 claims 1
- BBVBZYOWOGCUCH-UHFFFAOYSA-N 2-[6-[[2-(3-chloro-2,6-difluorophenyl)imidazol-1-yl]methyl]-5-ethylpyridazin-3-yl]-1,3-thiazole Chemical compound CCC1=CC(C=2SC=CN=2)=NN=C1CN1C=CN=C1C1=C(F)C=CC(Cl)=C1F BBVBZYOWOGCUCH-UHFFFAOYSA-N 0.000 claims 1
- OSZONPVQLSYEQK-UHFFFAOYSA-N 2-[6-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propylpyridazin-3-yl]-1,3-thiazole Chemical compound CCCC1=CC(C=2SC=CN=2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=N1 OSZONPVQLSYEQK-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- QFZABYKBNVYAJC-UHFFFAOYSA-N 3-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-4-propyl-6-pyrimidin-5-ylpyridazine Chemical compound CCCC1=CC(C=2C=NC=NC=2)=NN=C1CN1C=CN=C1C1=NC=CC=C1F QFZABYKBNVYAJC-UHFFFAOYSA-N 0.000 claims 1
- BIYFUSPPTFUWGO-UHFFFAOYSA-N 3-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-4-propylpyridazine Chemical compound CCCC1=CC=NN=C1CN1C(C=2C(=CC=CN=2)F)=NC=C1 BIYFUSPPTFUWGO-UHFFFAOYSA-N 0.000 claims 1
- ZFWNBYLIQPGCQB-UHFFFAOYSA-N 3-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-methoxy-4-propylpyridazine Chemical compound CCCC1=CC(OC)=NN=C1CN1C(C=2C(=CC=CN=2)F)=NC=C1 ZFWNBYLIQPGCQB-UHFFFAOYSA-N 0.000 claims 1
- NEAFURIKNKLQPN-UHFFFAOYSA-N 3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-4,6-dimethoxypyridazine Chemical compound N1=NC(OC)=CC(OC)=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 NEAFURIKNKLQPN-UHFFFAOYSA-N 0.000 claims 1
- XBNNILZFXIFMJM-UHFFFAOYSA-N 3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-4,6-dipropylpyridazine Chemical compound N1=NC(CCC)=CC(CCC)=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 XBNNILZFXIFMJM-UHFFFAOYSA-N 0.000 claims 1
- CAPNFIFKPASRGA-UHFFFAOYSA-N 3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-4-propyl-6-pyrazin-2-ylpyridazine Chemical compound CCCC1=CC(C=2N=CC=NC=2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=N1 CAPNFIFKPASRGA-UHFFFAOYSA-N 0.000 claims 1
- ADNLTWGXDNYFGC-UHFFFAOYSA-N 3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-4-propyl-6-pyridin-2-ylpyridazine Chemical compound CCCC1=CC(C=2N=CC=CC=2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=N1 ADNLTWGXDNYFGC-UHFFFAOYSA-N 0.000 claims 1
- KZJVWJFZDQVDND-UHFFFAOYSA-N 3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-4-propyl-6-pyridin-3-ylpyridazine Chemical compound CCCC1=CC(C=2C=NC=CC=2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=N1 KZJVWJFZDQVDND-UHFFFAOYSA-N 0.000 claims 1
- MVVWXWORNXLWRK-UHFFFAOYSA-N 3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-4-propyl-6-pyridin-4-ylpyridazine Chemical compound CCCC1=CC(C=2C=CN=CC=2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=N1 MVVWXWORNXLWRK-UHFFFAOYSA-N 0.000 claims 1
- ISJUZYUIXPVLLP-UHFFFAOYSA-N 3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-4-propylpyridazine Chemical compound CCCC1=CC=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 ISJUZYUIXPVLLP-UHFFFAOYSA-N 0.000 claims 1
- RRZOIBMOOQZJGG-UHFFFAOYSA-N 3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-methyl-4-propylpyridazine Chemical compound CCCC1=C(C)C=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 RRZOIBMOOQZJGG-UHFFFAOYSA-N 0.000 claims 1
- UOQITUWVHWFNIW-UHFFFAOYSA-N 3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-(3-methoxyprop-1-ynyl)-4-propylpyridazine Chemical compound CCCC1=CC(C#CCOC)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 UOQITUWVHWFNIW-UHFFFAOYSA-N 0.000 claims 1
- VQXDZVJHMCCHMW-UHFFFAOYSA-N 3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-(3-methoxypropyl)-4-propylpyridazine Chemical compound CCCC1=CC(CCCOC)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 VQXDZVJHMCCHMW-UHFFFAOYSA-N 0.000 claims 1
- QCNOGUPWFVZXJX-UHFFFAOYSA-N 3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-methoxy-4-propylpyridazine Chemical compound CCCC1=CC(OC)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 QCNOGUPWFVZXJX-UHFFFAOYSA-N 0.000 claims 1
- WMJDRDHDHKBRSU-UHFFFAOYSA-N 3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-methyl-4-propylpyridazine Chemical compound CCCC1=CC(C)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 WMJDRDHDHKBRSU-UHFFFAOYSA-N 0.000 claims 1
- LBGGKTDGGYJGSQ-UHFFFAOYSA-N 3-chloro-6-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-4-methyl-5-propylpyridazine Chemical compound CCCC1=C(C)C(Cl)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 LBGGKTDGGYJGSQ-UHFFFAOYSA-N 0.000 claims 1
- HMGOASIREUAWDZ-UHFFFAOYSA-N 4,6-diethoxy-3-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]pyridazine Chemical compound N1=NC(OCC)=CC(OCC)=C1CN1C(C=2C(=CC=CN=2)F)=NC=C1 HMGOASIREUAWDZ-UHFFFAOYSA-N 0.000 claims 1
- ZOPGOOYPCJDDTM-UHFFFAOYSA-N 4,6-diethoxy-3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]pyridazine Chemical compound N1=NC(OCC)=CC(OCC)=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 ZOPGOOYPCJDDTM-UHFFFAOYSA-N 0.000 claims 1
- QMDJZYTVQGXFCS-UHFFFAOYSA-N 4-[5-ethyl-6-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]pyridazin-3-yl]morpholine Chemical compound CCC1=CC(N2CCOCC2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=C1 QMDJZYTVQGXFCS-UHFFFAOYSA-N 0.000 claims 1
- BXIFAKSSVADTFG-UHFFFAOYSA-N 4-[6-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propylpyridazin-3-yl]-2-methylbut-3-yn-2-ol Chemical compound CCCC1=CC(C#CC(C)(C)O)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 BXIFAKSSVADTFG-UHFFFAOYSA-N 0.000 claims 1
- GKZDXXYYRMKMRB-UHFFFAOYSA-N 4-[6-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propylpyridazin-3-yl]-2-methylbutan-2-ol Chemical compound CCCC1=CC(CCC(C)(C)O)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 GKZDXXYYRMKMRB-UHFFFAOYSA-N 0.000 claims 1
- JKAMQUDQAQOMNM-UHFFFAOYSA-N 4-ethoxy-3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-methylpyridazine Chemical compound CCOC1=CC(C)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 JKAMQUDQAQOMNM-UHFFFAOYSA-N 0.000 claims 1
- QBXIBRWDHHEBIK-UHFFFAOYSA-N 4-ethoxy-3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-pyridin-3-ylpyridazine Chemical compound CCOC1=CC(C=2C=NC=CC=2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=N1 QBXIBRWDHHEBIK-UHFFFAOYSA-N 0.000 claims 1
- LOMBETJFWJNZOG-UHFFFAOYSA-N 4-ethyl-3-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]-6-(2-methoxyethoxy)pyridazine Chemical compound CCC1=CC(OCCOC)=NN=C1CN1C(C=2C=C(F)C=CC=2)=NC=C1 LOMBETJFWJNZOG-UHFFFAOYSA-N 0.000 claims 1
- OUHWVFMSBFPZDY-UHFFFAOYSA-N 4-ethyl-3-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]-6-(3-methoxyprop-1-ynyl)pyridazine Chemical compound CCC1=CC(C#CCOC)=NN=C1CN1C(C=2C=C(F)C=CC=2)=NC=C1 OUHWVFMSBFPZDY-UHFFFAOYSA-N 0.000 claims 1
- XCEIXMMIBCLSCS-UHFFFAOYSA-N 4-ethyl-3-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]-6-methoxypyridazine Chemical compound CCC1=CC(OC)=NN=C1CN1C(C=2C=C(F)C=CC=2)=NC=C1 XCEIXMMIBCLSCS-UHFFFAOYSA-N 0.000 claims 1
- JEKLSRVVSIUEMU-UHFFFAOYSA-N 4-ethyl-3-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]-6-piperidin-1-ylpyridazine Chemical compound CCC1=CC(N2CCCCC2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=C1 JEKLSRVVSIUEMU-UHFFFAOYSA-N 0.000 claims 1
- GTKUHPYXKPMJEE-UHFFFAOYSA-N 4-ethyl-3-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]pyridazine Chemical compound CCC1=CC=NN=C1CN1C(C=2C=C(F)C=CC=2)=NC=C1 GTKUHPYXKPMJEE-UHFFFAOYSA-N 0.000 claims 1
- SUTFNFBTDRPYPB-UHFFFAOYSA-N 4-ethyl-3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-pyridin-3-ylpyridazine Chemical compound CCC1=CC(C=2C=NC=CC=2)=NN=C1CN1C=CN=C1C1=CC=CC(F)=N1 SUTFNFBTDRPYPB-UHFFFAOYSA-N 0.000 claims 1
- FERJMNOKBJIAJR-UHFFFAOYSA-N 4-propyl-3-[(2-pyridin-2-ylimidazol-1-yl)methyl]pyridazine Chemical compound CCCC1=CC=NN=C1CN1C(C=2N=CC=CC=2)=NC=C1 FERJMNOKBJIAJR-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- ZEAHCERLTDWEKC-UHFFFAOYSA-N 6-chloro-3-[[2-(2,3-difluorophenyl)imidazol-1-yl]methyl]-4-ethylpyridazine Chemical compound CCC1=CC(Cl)=NN=C1CN1C(C=2C(=C(F)C=CC=2)F)=NC=C1 ZEAHCERLTDWEKC-UHFFFAOYSA-N 0.000 claims 1
- HOLSMJQOVSSHLF-UHFFFAOYSA-N 6-chloro-3-[[2-(2,5-difluorophenyl)imidazol-1-yl]methyl]-4-ethylpyridazine Chemical compound CCC1=CC(Cl)=NN=C1CN1C(C=2C(=CC=C(F)C=2)F)=NC=C1 HOLSMJQOVSSHLF-UHFFFAOYSA-N 0.000 claims 1
- OIKKGXFBODKDJV-UHFFFAOYSA-N 6-chloro-3-[[2-(3-chloro-2,6-difluorophenyl)imidazol-1-yl]methyl]-4-ethylpyridazine Chemical compound CCC1=CC(Cl)=NN=C1CN1C(C=2C(=C(Cl)C=CC=2F)F)=NC=C1 OIKKGXFBODKDJV-UHFFFAOYSA-N 0.000 claims 1
- HMXLPNRAAUANNY-UHFFFAOYSA-N 6-chloro-3-[[2-(3-chloro-2,6-difluorophenyl)imidazol-1-yl]methyl]-4-methoxypyridazine Chemical compound COC1=CC(Cl)=NN=C1CN1C(C=2C(=C(Cl)C=CC=2F)F)=NC=C1 HMXLPNRAAUANNY-UHFFFAOYSA-N 0.000 claims 1
- GXYRPICXYIDUTN-UHFFFAOYSA-N 6-chloro-3-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-4-propylpyridazine Chemical compound CCCC1=CC(Cl)=NN=C1CN1C(C=2C(=CC=CN=2)F)=NC=C1 GXYRPICXYIDUTN-UHFFFAOYSA-N 0.000 claims 1
- NBIZUQFXKBAKFG-UHFFFAOYSA-N 6-chloro-3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-4-propylpyridazine Chemical compound CCCC1=CC(Cl)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 NBIZUQFXKBAKFG-UHFFFAOYSA-N 0.000 claims 1
- YCSYYDFFCXBFGE-UHFFFAOYSA-N 6-chloro-3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-n-propylpyridazin-4-amine Chemical compound CCCNC1=CC(Cl)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 YCSYYDFFCXBFGE-UHFFFAOYSA-N 0.000 claims 1
- PWCVJNIHQROZBI-UHFFFAOYSA-N 6-chloro-4-ethoxy-3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]pyridazine Chemical compound CCOC1=CC(Cl)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 PWCVJNIHQROZBI-UHFFFAOYSA-N 0.000 claims 1
- AWJGWXXJQARIIX-UHFFFAOYSA-N 6-chloro-4-ethyl-3-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]pyridazine Chemical compound CCC1=CC(Cl)=NN=C1CN1C(C=2C=C(F)C=CC=2)=NC=C1 AWJGWXXJQARIIX-UHFFFAOYSA-N 0.000 claims 1
- JUTGZFOVBUSESE-UHFFFAOYSA-N 6-chloro-4-ethyl-3-[[2-(5-fluoro-2-methylphenyl)imidazol-1-yl]methyl]pyridazine Chemical compound CCC1=CC(Cl)=NN=C1CN1C(C=2C(=CC=C(F)C=2)C)=NC=C1 JUTGZFOVBUSESE-UHFFFAOYSA-N 0.000 claims 1
- BLSMIHGSXWMBJI-UHFFFAOYSA-N 6-chloro-n,n-diethyl-3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]pyridazin-4-amine Chemical compound CCN(CC)C1=CC(Cl)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 BLSMIHGSXWMBJI-UHFFFAOYSA-N 0.000 claims 1
- SMQLGIJZHIDBNC-UHFFFAOYSA-N 6-chloro-n-ethyl-3-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]pyridazin-4-amine Chemical compound CCNC1=CC(Cl)=NN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 SMQLGIJZHIDBNC-UHFFFAOYSA-N 0.000 claims 1
- XVGIXVGUHPDXSK-UHFFFAOYSA-N 6-ethoxy-4-ethyl-3-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]pyridazine Chemical compound N1=NC(OCC)=CC(CC)=C1CN1C(C=2C=C(F)C=CC=2)=NC=C1 XVGIXVGUHPDXSK-UHFFFAOYSA-N 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000004650 C1-C8 alkynyl group Chemical group 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 238000000376 autoradiography Methods 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 230000003834 intracellular effect Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 230000006403 short-term memory Effects 0.000 claims 1
- 230000019491 signal transduction Effects 0.000 claims 1
- 230000007781 signaling event Effects 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41666002P | 2002-10-07 | 2002-10-07 | |
| PCT/IB2003/004382 WO2004031174A1 (en) | 2002-10-07 | 2003-10-06 | Imidazol-1-ylmethyl pyridazine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006504714A JP2006504714A (ja) | 2006-02-09 |
| JP2006504714A5 true JP2006504714A5 (https=) | 2006-11-16 |
Family
ID=32069951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004541111A Pending JP2006504714A (ja) | 2002-10-07 | 2003-10-06 | イミダゾール−１−イルメチルピリダジン誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7122546B2 (https=) |
| EP (1) | EP1549636A1 (https=) |
| JP (1) | JP2006504714A (https=) |
| CN (1) | CN100579579C (https=) |
| AU (1) | AU2003267722A1 (https=) |
| CA (1) | CA2495698A1 (https=) |
| WO (1) | WO2004031174A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE335732T1 (de) * | 2002-11-08 | 2006-09-15 | Neurogen Corp | 4-imidazol-1-ylmethylpyrimidinderivate als liganden für gabaa-rezeptoren |
| EP1594848A1 (en) | 2003-02-19 | 2005-11-16 | Neurogen Corporation | Aryl acid pyrimidinyl methyl amides, pyridazinyl methyl amides and related compounds |
| WO2005012306A2 (en) * | 2003-07-25 | 2005-02-10 | Neurogen Corporation | Imidazo-pyrimidines and triazolo-pyrimidines: benzodiazepine receptor ligands |
| KR101170925B1 (ko) * | 2004-06-18 | 2012-08-07 | 노바티스 백신즈 앤드 다이아그노스틱스 인코포레이티드 | 암 치료용 키네신 방추 단백질 (ｋｓｐ) 억제제로서의ｎ-(1-(1-벤질-4-페닐-1ｈ-이미다졸-2-일)-2,2-디메틸프로필)벤자미드 유도체 및 관련 화합물 |
| AU2008205169B2 (en) | 2007-01-05 | 2012-02-02 | Novartis Ag | Imidazole derivatives as kinesin spindle protein inhibitors (Eg-5) |
| MX2009007661A (es) | 2007-01-19 | 2009-12-14 | Ardea Biosciences Inc | Inhibidores de mek. |
| US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
| WO2014094182A1 (en) * | 2012-12-21 | 2014-06-26 | Ottawa Hospital Research Institute | Non-replicating virus-derived particles and uses thereof |
| HRP20210764T1 (hr) | 2017-03-30 | 2021-07-09 | Bristol-Myers Squibb Company | Postupak za pripremu 6-(ciklopropanamido)-4-((2-metoksi-3-(1-metil-1h-1,2,4-triazol-3-il)fenil)amino)-n-(metil-d3)piridazin-3-karboksamida |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6200959B1 (en) * | 1996-12-04 | 2001-03-13 | Powerject Vaccines Inc. | Genetic induction of anti-viral immune response and genetic vaccine for filovirus |
| JP2002527401A (ja) * | 1998-10-13 | 2002-08-27 | カイロン コーポレイション | Ｆｇｆの脈管形成的に有効な単位用量および投与方法 |
| AU2001270297A1 (en) * | 2000-06-30 | 2002-01-14 | Neurogen Corporation | 2-phenylimidazo(1,2-a)pyridine derivatives: a new class of gaba brain receptor ligands |
| PA8535601A1 (es) * | 2000-12-21 | 2002-11-28 | Pfizer | Derivados benzimidazol y piridilimidazol como ligandos para gabaa |
| JP2006515278A (ja) * | 2002-05-08 | 2006-05-25 | ニューロジェン コーポレイション | 置換イミダゾリルメチルピリジン及びピラジン誘導体並びにそれらのｇａｂａａ受容体リガンドとしての使用 |
| US7005432B2 (en) * | 2002-05-16 | 2006-02-28 | Hoffman-La Roche Inc. | Substituted imidazol-pyridazine derivatives |
| ATE335732T1 (de) | 2002-11-08 | 2006-09-15 | Neurogen Corp | 4-imidazol-1-ylmethylpyrimidinderivate als liganden für gabaa-rezeptoren |
| CA2524376A1 (en) | 2003-05-05 | 2004-12-16 | Neurogen Corporation | Substituted imidazolopyrazine and triazolopyrazyne derivatives: gabaa receptor ligands |
-
2003
- 2003-10-01 CN CN200380104308A patent/CN100579579C/zh not_active Expired - Fee Related
- 2003-10-06 JP JP2004541111A patent/JP2006504714A/ja active Pending
- 2003-10-06 WO PCT/IB2003/004382 patent/WO2004031174A1/en not_active Ceased
- 2003-10-06 EP EP03748416A patent/EP1549636A1/en not_active Withdrawn
- 2003-10-06 AU AU2003267722A patent/AU2003267722A1/en not_active Abandoned
- 2003-10-06 CA CA002495698A patent/CA2495698A1/en not_active Abandoned
- 2003-10-07 US US10/680,351 patent/US7122546B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US11964961B2 (en) | Heteroaromatic compounds and their use as dopamine D1 ligands | |
| KR101819433B1 (ko) | 인돌린-2-온 또는 피롤로-피리딘-2-온 유도체 | |
| EP3371164B1 (en) | N-[2-(1-benzylpiperidin-4-yl)ethyl]-4-(pyrazin-2-yl)-piperazine-1-carboxamide derivatives and related compounds as muscarinic receptor 4 (m4) antagonists for treating neurological diseases | |
| AU2002363176B2 (en) | Heteroaryl amines as glycogen synthase kinase 3Beta inhibitors (GSK3 inhibitors) | |
| JP2009541311A5 (https=) | ||
| DK3152199T3 (en) | PYRAZOLE COMPOUNDS AND THEIR USE AS T-TYPE CALCIUM CHANNEL BLOCKERS | |
| JP2020516671A5 (https=) | ||
| JP4349657B2 (ja) | 置換アザ―及びジアザシクロヘプタン―及び―シクロオクタン化合物及びその使用 | |
| AU2004220382B2 (en) | Imidazol-4-yl-ethynyl-pyridine derivatives | |
| JP2010533736A5 (https=) | ||
| HK1255830A1 (en) | Heteroaromatic compounds and their use as dopamine d1 ligands | |
| JP2008513514A5 (https=) | ||
| CA2463823A1 (en) | Aminobenzamide derivatives as glycogen synthase kinase 3.beta. inhibitors | |
| JP2022141699A (ja) | 疼痛を治療するためのｋｖ３チャネルのモジュレーター | |
| RU2015154987A (ru) | Гетероциклические производные | |
| IL263511A (en) | 1h-pyrazolo[4,3-b]pyridines as pde1 inhibitors | |
| CA2306093A1 (en) | Heteroaryl diazacycloalkanes as cholinergic ligands at nicotinic acetylcholine receptors | |
| JP2006504714A5 (https=) | ||
| RU2019123319A (ru) | Пиразолопиримидины и способы их применения | |
| JP2008506766A (ja) | ヒスタミン−３受容体拮抗薬 | |
| Altenbach et al. | Synthesis, potency, and in vivo profiles of quinoline containing histamine H3 receptor inverse agonists | |
| JP2018516982A5 (ja) | 免疫療法用組み合わせ組成物 | |
| JP2006508102A5 (https=) | ||
| JPWO2020179859A5 (https=) | ||
| AU2004247368B2 (en) | Heteroaryl-substituted imidazole derivatives as glutamate receptor antagonists |