JP2006504714A5 - - Google Patents
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- 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
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- 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
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| 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)
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| JP2006504714A JP2006504714A (ja) | 2006-02-09 |
| JP2006504714A5 true JP2006504714A5 (https=) | 2006-11-16 |
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| EP (1) | EP1549636A1 (https=) |
| JP (1) | JP2006504714A (https=) |
| CN (1) | CN100579579C (https=) |
| AU (1) | AU2003267722A1 (https=) |
| CA (1) | CA2495698A1 (https=) |
| WO (1) | WO2004031174A1 (https=) |
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| AU2003276514A1 (en) * | 2002-11-08 | 2004-06-07 | Neurogen Corporation | 4-imidazol-1-ylmethyl-pyrimidine derivatives_as ligands for gabaa receptors |
| EP1594848A1 (en) | 2003-02-19 | 2005-11-16 | Neurogen Corporation | Aryl acid pyrimidinyl methyl amides, pyridazinyl methyl amides and related compounds |
| BRPI0412908A (pt) * | 2003-07-25 | 2006-09-26 | Neurogen Corp | composto ou um sal deste farmaceuticamente aceitável, composição farmacêutica, métodos para o tratamento de ansiedade, depressão, um distúrbio do sono, distúrbio de déficit de atenção ou demência de alzheimer, para potenciar um efeito terapêutico de um agente do cns, para melhorar a memória de curta duração em um paciente, para alterar a atividade de transdução de sinal de receptor gabaa, e para determinar a presença ou ausência de receptor gabaa em uma amostra, preparação farmacêutica acondicionada, e, uso de um composto ou sal |
| BRPI0510929A (pt) | 2004-06-18 | 2007-07-17 | Chiron Corp | derivados de n-(1-(1-benzil-4-fenil-1h-imidazol-2-il)-2,2-dimetilpropil) benzamida e compostos relacionados como inibidores de proteìna de eixo de kinesin (ksp) para o tratamento de cáncer |
| WO2008086122A2 (en) | 2007-01-05 | 2008-07-17 | Novartis Ag | Imidazole derivatives as kinesin spindle protein inhibitors (eg-5) |
| KR20090111847A (ko) | 2007-01-19 | 2009-10-27 | 아디아 바이오사이언스즈 인크. | Ｍｅｋ 억제제 |
| US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
| RU2705556C2 (ru) * | 2012-12-21 | 2019-11-07 | Келверум Инк. | Нереплицируемые происходящие от вирусов частицы и их применение |
| JP7113023B2 (ja) | 2017-03-30 | 2022-08-04 | ブリストル－マイヤーズ スクイブ カンパニー | ６－（シクロプロパンアミド）－４－（（２－メトキシ－３－（１－メチル－１ｈ－１，２，４－トリアゾール－３－イル）フェニル）アミノ）－ｎ－（メチル－ｄ３）ピリダジン－３－カルボキシアミドの製造方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| WO2002002557A2 (en) * | 2000-06-30 | 2002-01-10 | 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 |
| WO2004041809A2 (en) * | 2002-05-08 | 2004-05-21 | Neurogen Corporation | Substituted imidazolylmethyl pyridine and pyrazine derivatives and their use as gabaa receptor ligands |
| US7005432B2 (en) * | 2002-05-16 | 2006-02-28 | Hoffman-La Roche Inc. | Substituted imidazol-pyridazine derivatives |
| AU2003276514A1 (en) | 2002-11-08 | 2004-06-07 | Neurogen Corporation | 4-imidazol-1-ylmethyl-pyrimidine derivatives_as ligands for gabaa receptors |
| US20060247245A1 (en) | 2003-05-05 | 2006-11-02 | Yuelian Xu | Substituted imidazolopyrazine and triazolopyrazine derivatives: gabaa receptor ligands |
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- 2003-10-06 CA CA002495698A patent/CA2495698A1/en not_active Abandoned
- 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 AU AU2003267722A patent/AU2003267722A1/en not_active Abandoned
- 2003-10-06 EP EP03748416A patent/EP1549636A1/en not_active Withdrawn
- 2003-10-07 US US10/680,351 patent/US7122546B2/en not_active Expired - Fee Related
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