JP2007506723A5 - - Google Patents
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- Publication number
- JP2007506723A5 JP2007506723A5 JP2006527492A JP2006527492A JP2007506723A5 JP 2007506723 A5 JP2007506723 A5 JP 2007506723A5 JP 2006527492 A JP2006527492 A JP 2006527492A JP 2006527492 A JP2006527492 A JP 2006527492A JP 2007506723 A5 JP2007506723 A5 JP 2007506723A5
- Authority
- JP
- Japan
- Prior art keywords
- diazabicyclo
- nonane
- ylmethyl
- methane
- phenyl
- 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 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 201000010099 disease Diseases 0.000 claims 7
- 230000006735 deficit Effects 0.000 claims 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 208000020925 Bipolar disease Diseases 0.000 claims 3
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- 208000023105 Huntington disease Diseases 0.000 claims 3
- 201000006347 Intellectual Disability Diseases 0.000 claims 3
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 3
- 206010026749 Mania Diseases 0.000 claims 3
- 208000026139 Memory disease Diseases 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 208000000323 Tourette Syndrome Diseases 0.000 claims 3
- 208000016620 Tourette disease Diseases 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 3
- 230000036506 anxiety Effects 0.000 claims 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 3
- -1 benzoimidazolyl Chemical group 0.000 claims 3
- 208000028683 bipolar I disease Diseases 0.000 claims 3
- 230000001713 cholinergic effect Effects 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 230000007812 deficiency Effects 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 3
- 206010027175 memory impairment Diseases 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- XJIRVFAJKTXNCO-UHFFFAOYSA-N 4-[(6-phenylpyridin-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(N=1)=CC=CC=1C1=CC=CC=C1 XJIRVFAJKTXNCO-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000025966 Neurological disease Diseases 0.000 claims 2
- 206010057852 Nicotine dependence Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 208000025569 Tobacco Use disease Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 235000019788 craving Nutrition 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 210000000225 synapse Anatomy 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- UBQRZXFQKHPJLR-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-1,3-benzothiazole Chemical compound N=1C2=CC=CC=C2SC=1CN1CCN2CCC1CC2 UBQRZXFQKHPJLR-UHFFFAOYSA-N 0.000 claims 1
- LNRJGAIONKZYFP-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-1,3-thiazole Chemical compound C1CN(CC2)CCC2N1CC1=NC=CS1 LNRJGAIONKZYFP-UHFFFAOYSA-N 0.000 claims 1
- VINNGRZRDRNSNC-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-1-methylbenzimidazole Chemical compound N=1C2=CC=CC=C2N(C)C=1CN1CCN2CCC1CC2 VINNGRZRDRNSNC-UHFFFAOYSA-N 0.000 claims 1
- GNZVWKCOUAAILG-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-4-(3-phenylphenyl)-1,3-thiazole Chemical compound C1CN(CC2)CCC2N1CC(SC=1)=NC=1C(C=1)=CC=CC=1C1=CC=CC=C1 GNZVWKCOUAAILG-UHFFFAOYSA-N 0.000 claims 1
- REFQQYQNWHWHQB-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-4-phenyl-1,3-thiazole Chemical compound C1CN(CC2)CCC2N1CC(SC=1)=NC=1C1=CC=CC=C1 REFQQYQNWHWHQB-UHFFFAOYSA-N 0.000 claims 1
- FBVNNGJZOTXVEF-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1CN1CCN2CCC1CC2 FBVNNGJZOTXVEF-UHFFFAOYSA-N 0.000 claims 1
- IJBCOAKSOSCNOI-UHFFFAOYSA-N 2-bromo-5-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-1,3-thiazole Chemical compound S1C(Br)=NC=C1CN1C(CC2)CCN2CC1 IJBCOAKSOSCNOI-UHFFFAOYSA-N 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- BSTFGTKPTYGRTP-UHFFFAOYSA-N 3-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)isoquinoline Chemical compound C=1C2=CC=CC=C2C=NC=1CN1CCN2CCC1CC2 BSTFGTKPTYGRTP-UHFFFAOYSA-N 0.000 claims 1
- PCCGBIBILVNICT-UHFFFAOYSA-N 3-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)quinoline Chemical compound C=1N=C2C=CC=CC2=CC=1CN1CCN2CCC1CC2 PCCGBIBILVNICT-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- DNZPQWHJYCWNHR-UHFFFAOYSA-N 4-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-2-phenyl-1,3-thiazole Chemical compound C1CN(CC2)CCC2N1CC(N=1)=CSC=1C1=CC=CC=C1 DNZPQWHJYCWNHR-UHFFFAOYSA-N 0.000 claims 1
- YCYFEVOWCCVAIH-UHFFFAOYSA-N 4-(1-benzofuran-2-ylmethyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C=1C2=CC=CC=C2OC=1CN1CCN2CCC1CC2 YCYFEVOWCCVAIH-UHFFFAOYSA-N 0.000 claims 1
- JQYJGTWBTCVOPV-UHFFFAOYSA-N 4-(1-benzothiophen-3-ylmethyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C=1SC2=CC=CC=C2C=1CN1CCN2CCC1CC2 JQYJGTWBTCVOPV-UHFFFAOYSA-N 0.000 claims 1
- CIRJBIVVIIOCFQ-UHFFFAOYSA-N 4-(2-phenylmethoxyethyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CCOCC1=CC=CC=C1 CIRJBIVVIIOCFQ-UHFFFAOYSA-N 0.000 claims 1
- GHLXUGORDMWOAW-UHFFFAOYSA-N 4-(3-bromophenyl)-2-(1,4-diazabicyclo[3.2.2]nonan-2-ylmethyl)-1,3-thiazole Chemical compound BrC1=CC=CC(C=2N=C(CC3N4CCC(CC4)NC3)SC=2)=C1 GHLXUGORDMWOAW-UHFFFAOYSA-N 0.000 claims 1
- LGWAFBWTSXBLIZ-UHFFFAOYSA-N 4-(3-phenylprop-2-enyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC=CC1=CC=CC=C1 LGWAFBWTSXBLIZ-UHFFFAOYSA-N 0.000 claims 1
- DAKWUNBEVQWFQO-UHFFFAOYSA-N 4-(3-phenylprop-2-ynyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC#CC1=CC=CC=C1 DAKWUNBEVQWFQO-UHFFFAOYSA-N 0.000 claims 1
- CBBFPWDAUGHFDQ-UHFFFAOYSA-N 4-(3-phenylpropyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CCCC1=CC=CC=C1 CBBFPWDAUGHFDQ-UHFFFAOYSA-N 0.000 claims 1
- FFOALWFFBNJVSM-UHFFFAOYSA-N 4-(naphthalen-2-ylmethyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C=1C=C2C=CC=CC2=CC=1CN1CCN2CCC1CC2 FFOALWFFBNJVSM-UHFFFAOYSA-N 0.000 claims 1
- LKPDYIBKLAVZRC-UHFFFAOYSA-N 4-(pyridin-2-ylmethyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC1=CC=CC=N1 LKPDYIBKLAVZRC-UHFFFAOYSA-N 0.000 claims 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 1
- LHPINYKVLZZJFF-UHFFFAOYSA-N 4-[(2-phenyl-1h-imidazol-5-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(N1)=CN=C1C1=CC=CC=C1 LHPINYKVLZZJFF-UHFFFAOYSA-N 0.000 claims 1
- OMWSHMFHPDFZGS-UHFFFAOYSA-N 4-[(3-methyl-5-phenylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound S1C(CN2C3CCN(CC3)CC2)=C(C)C=C1C1=CC=CC=C1 OMWSHMFHPDFZGS-UHFFFAOYSA-N 0.000 claims 1
- DPZPYDHIXALGSA-UHFFFAOYSA-N 4-[(3-phenylphenyl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(C=1)=CC=CC=1C1=CC=CC=C1 DPZPYDHIXALGSA-UHFFFAOYSA-N 0.000 claims 1
- DGWPBBPYBWXPMF-UHFFFAOYSA-N 4-[(4-bromofuran-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound BrC1=COC(CN2C3CCN(CC3)CC2)=C1 DGWPBBPYBWXPMF-UHFFFAOYSA-N 0.000 claims 1
- KUAYKLXQFSZOPP-UHFFFAOYSA-N 4-[(4-bromothiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound BrC1=CSC(CN2C3CCN(CC3)CC2)=C1 KUAYKLXQFSZOPP-UHFFFAOYSA-N 0.000 claims 1
- DRYMDZNFQNRGEI-UHFFFAOYSA-N 4-[(4-phenylphenyl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(C=C1)=CC=C1C1=CC=CC=C1 DRYMDZNFQNRGEI-UHFFFAOYSA-N 0.000 claims 1
- RPEKOGDSVCJAKQ-UHFFFAOYSA-N 4-[(4-phenylpyridin-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(N=CC=1)=CC=1C1=CC=CC=C1 RPEKOGDSVCJAKQ-UHFFFAOYSA-N 0.000 claims 1
- VLCXOFDFQNSQAJ-UHFFFAOYSA-N 4-[(4-phenylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(SC=1)=CC=1C1=CC=CC=C1 VLCXOFDFQNSQAJ-UHFFFAOYSA-N 0.000 claims 1
- LXKVUNZKWYSOOR-UHFFFAOYSA-N 4-[(4-pyridin-2-ylphenyl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(C=C1)=CC=C1C1=CC=CC=N1 LXKVUNZKWYSOOR-UHFFFAOYSA-N 0.000 claims 1
- GZSVFOHRTMTDLU-UHFFFAOYSA-N 4-[(4-pyridin-2-ylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(SC=1)=CC=1C1=CC=CC=N1 GZSVFOHRTMTDLU-UHFFFAOYSA-N 0.000 claims 1
- JJTBJROJFUAOAA-UHFFFAOYSA-N 4-[(4-pyridin-3-ylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(SC=1)=CC=1C1=CC=CN=C1 JJTBJROJFUAOAA-UHFFFAOYSA-N 0.000 claims 1
- YCAHNRCVGUBAOA-UHFFFAOYSA-N 4-[(4-pyridin-4-ylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(SC=1)=CC=1C1=CC=NC=C1 YCAHNRCVGUBAOA-UHFFFAOYSA-N 0.000 claims 1
- VLEYBICLJJPRTG-UHFFFAOYSA-N 4-[(5-bromothiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound S1C(Br)=CC=C1CN1C(CC2)CCN2CC1 VLEYBICLJJPRTG-UHFFFAOYSA-N 0.000 claims 1
- SYCWDENGJYVOJV-UHFFFAOYSA-N 4-[(5-phenylfuran-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(O1)=CC=C1C1=CC=CC=C1 SYCWDENGJYVOJV-UHFFFAOYSA-N 0.000 claims 1
- WICAHOKENBNMDX-UHFFFAOYSA-N 4-[(5-phenylpyridin-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(N=C1)=CC=C1C1=CC=CC=C1 WICAHOKENBNMDX-UHFFFAOYSA-N 0.000 claims 1
- KFRFUUPGALCOCO-UHFFFAOYSA-N 4-[(5-phenylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(S1)=CC=C1C1=CC=CC=C1 KFRFUUPGALCOCO-UHFFFAOYSA-N 0.000 claims 1
- SUPMGNMPUCWEOY-UHFFFAOYSA-N 4-[(5-pyridin-2-ylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(S1)=CC=C1C1=CC=CC=N1 SUPMGNMPUCWEOY-UHFFFAOYSA-N 0.000 claims 1
- IUXBMGXKYAWSKC-UHFFFAOYSA-N 4-[(5-pyridin-3-ylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(S1)=CC=C1C1=CC=CN=C1 IUXBMGXKYAWSKC-UHFFFAOYSA-N 0.000 claims 1
- FTAWJHRUSIWHPL-UHFFFAOYSA-N 4-[(5-pyridin-4-ylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(S1)=CC=C1C1=CC=NC=C1 FTAWJHRUSIWHPL-UHFFFAOYSA-N 0.000 claims 1
- XYDWNLYPKBUXEC-UHFFFAOYSA-N 4-[(6-bromopyridin-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound BrC1=CC=CC(CN2C3CCN(CC3)CC2)=N1 XYDWNLYPKBUXEC-UHFFFAOYSA-N 0.000 claims 1
- RVYLILSHTMEGAA-UHFFFAOYSA-N 4-[[4-(4-bromophenyl)sulfanylphenyl]methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1=CC(Br)=CC=C1SC(C=C1)=CC=C1CN1C(CC2)CCN2CC1 RVYLILSHTMEGAA-UHFFFAOYSA-N 0.000 claims 1
- MYMLUBIRFYEEJA-UHFFFAOYSA-N 4-[[4-(4-chlorophenyl)phenyl]methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1=CC(Cl)=CC=C1C(C=C1)=CC=C1CN1C(CC2)CCN2CC1 MYMLUBIRFYEEJA-UHFFFAOYSA-N 0.000 claims 1
- VQLLTSIHENQOJI-UHFFFAOYSA-N 4-[[4-[3-(trifluoromethyl)phenyl]phenyl]methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound FC(F)(F)C1=CC=CC(C=2C=CC(CN3C4CCN(CC4)CC3)=CC=2)=C1 VQLLTSIHENQOJI-UHFFFAOYSA-N 0.000 claims 1
- ZUBYOXKIYJEMIK-UHFFFAOYSA-N 4-oct-2-ynyl-1,4-diazabicyclo[3.2.2]nonane Chemical compound CCCCCC#CCN1CCN2CCC1CC2 ZUBYOXKIYJEMIK-UHFFFAOYSA-N 0.000 claims 1
- XQQUUTAPJQCLAI-UHFFFAOYSA-N 5-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-1,3-thiazole Chemical compound C1CN(CC2)CCC2N1CC1=CN=CS1 XQQUUTAPJQCLAI-UHFFFAOYSA-N 0.000 claims 1
- LSUJLNVZDMUTAL-UHFFFAOYSA-N 5-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-2-phenyl-1,3-thiazole Chemical compound C1CN(CC2)CCC2N1CC(S1)=CN=C1C1=CC=CC=C1 LSUJLNVZDMUTAL-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims 1
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 201000003723 learning disability Diseases 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims 1
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000005586 smoking cessation Effects 0.000 claims 1
- 230000000946 synaptic effect Effects 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50666403P | 2003-09-26 | 2003-09-26 | |
| PCT/GB2004/004130 WO2005030777A1 (en) | 2003-09-26 | 2004-09-24 | Non-amide nonanes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007506723A JP2007506723A (ja) | 2007-03-22 |
| JP2007506723A5 true JP2007506723A5 (enExample) | 2007-10-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006527492A Pending JP2007506723A (ja) | 2003-09-26 | 2004-09-24 | 非アミド性ノナン |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7482338B2 (enExample) |
| EP (1) | EP1673372B1 (enExample) |
| JP (1) | JP2007506723A (enExample) |
| AT (1) | ATE363484T1 (enExample) |
| DE (1) | DE602004006767T2 (enExample) |
| ES (1) | ES2285514T3 (enExample) |
| WO (1) | WO2005030777A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2386633C2 (ru) | 2004-05-07 | 2010-04-20 | Мемори Фармасьютиклз Корпорейшн | 1h-индазолы, бензотиазолы, 1, 2-бензоизоксазолы, 1, 2-бензоизотиазолы и хромоны и их получение и применения |
| WO2010145208A1 (en) * | 2009-06-19 | 2010-12-23 | Abbott Laboratories | Diazahomoadamantane derivatives and methods of use thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4895943A (en) * | 1988-10-25 | 1990-01-23 | Pfizer Inc. | Preparation of 1,4-diazabicyclo(3.2.2)nonane |
| US5679673A (en) * | 1992-09-24 | 1997-10-21 | The United States Of America, Represented By The Department Of Health And Human Services | Aralkyl bridged diazabicycloalkane derivatives for CNS disorders |
| FR2786770B1 (fr) | 1998-12-04 | 2001-01-19 | Synthelabo | Derives de 1,4-diazabicyclo[3.2.2.]nonane, leur preparation et leur application en therapeutique |
| FR2809731B1 (fr) * | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | Derives de 1,4-diazabicyclo-[3.2.2] nonane-pheylisoxazole, leur preparation et leur application en therapeutique |
| US20020086871A1 (en) | 2000-12-29 | 2002-07-04 | O'neill Brian Thomas | Pharmaceutical composition for the treatment of CNS and other disorders |
-
2004
- 2004-09-24 AT AT04768673T patent/ATE363484T1/de not_active IP Right Cessation
- 2004-09-24 EP EP04768673A patent/EP1673372B1/en not_active Expired - Lifetime
- 2004-09-24 DE DE602004006767T patent/DE602004006767T2/de not_active Expired - Fee Related
- 2004-09-24 US US10/573,132 patent/US7482338B2/en not_active Expired - Fee Related
- 2004-09-24 ES ES04768673T patent/ES2285514T3/es not_active Expired - Lifetime
- 2004-09-24 WO PCT/GB2004/004130 patent/WO2005030777A1/en not_active Ceased
- 2004-09-24 JP JP2006527492A patent/JP2007506723A/ja active Pending
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