JP2011519839A5 - - Google Patents
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- Publication number
- JP2011519839A5 JP2011519839A5 JP2011506690A JP2011506690A JP2011519839A5 JP 2011519839 A5 JP2011519839 A5 JP 2011519839A5 JP 2011506690 A JP2011506690 A JP 2011506690A JP 2011506690 A JP2011506690 A JP 2011506690A JP 2011519839 A5 JP2011519839 A5 JP 2011519839A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- benzodioxin
- methyl
- stereoisomers
- difluoro
- 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.)
- Abandoned
Links
- -1 3,3,3-trifluoropropyl Chemical group 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 150000001204 N-oxides Chemical class 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000012661 Dyskinesia Diseases 0.000 claims 2
- 208000004547 Hallucinations Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 230000010249 dopaminergic function Effects 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 230000000642 iatrogenic effect Effects 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- RYAKTYSLDHIVCN-UHFFFAOYSA-N 1-(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)-n,n-dimethylmethanamine Chemical compound C1=C(F)C=C2OC(CN(C)C)COC2=C1F RYAKTYSLDHIVCN-UHFFFAOYSA-N 0.000 claims 1
- LLWYKNWFNNIBNJ-UHFFFAOYSA-N 1-(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)-n-methylmethanamine Chemical compound C1=C(F)C=C2OC(CNC)COC2=C1F LLWYKNWFNNIBNJ-UHFFFAOYSA-N 0.000 claims 1
- WBXWZWDHWBZBEW-UHFFFAOYSA-N 1-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]azetidine Chemical compound O1C2=CC(F)=CC(F)=C2OCC1CN1CCC1 WBXWZWDHWBZBEW-UHFFFAOYSA-N 0.000 claims 1
- IMGVMEGUBZMRMQ-UHFFFAOYSA-N 1-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]piperidine Chemical compound O1C2=CC(F)=CC(F)=C2OCC1CN1CCCCC1 IMGVMEGUBZMRMQ-UHFFFAOYSA-N 0.000 claims 1
- KRYLSWWQBDOHSK-UHFFFAOYSA-N 1-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]pyrrolidine Chemical compound O1C2=CC(F)=CC(F)=C2OCC1CN1CCCC1 KRYLSWWQBDOHSK-UHFFFAOYSA-N 0.000 claims 1
- BVULOCLUGAZEHK-UHFFFAOYSA-N 1-[(6,7-difluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]pyrrolidine Chemical compound O1C=2C=C(F)C(F)=CC=2OCC1CN1CCCC1 BVULOCLUGAZEHK-UHFFFAOYSA-N 0.000 claims 1
- MIKPAAQUZXLXHK-UHFFFAOYSA-N 1-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]azetidine Chemical compound O1C2=CC(F)=CC=C2OCC1CN1CCC1 MIKPAAQUZXLXHK-UHFFFAOYSA-N 0.000 claims 1
- ULLHFRXISCCAFU-UHFFFAOYSA-N 1-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]piperidine Chemical compound O1C2=CC(F)=CC=C2OCC1CN1CCCCC1 ULLHFRXISCCAFU-UHFFFAOYSA-N 0.000 claims 1
- JPEIWVHWEYEDPK-NSHDSACASA-N 1-[[(3s)-6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]pyrrolidine Chemical compound C([C@H]1COC2=CC=C(C=C2O1)F)N1CCCC1 JPEIWVHWEYEDPK-NSHDSACASA-N 0.000 claims 1
- RDYNMWBALJWPQP-UHFFFAOYSA-N 2-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methylamino]ethanol Chemical compound C1=C(F)C=C2OC(CNCCO)COC2=C1F RDYNMWBALJWPQP-UHFFFAOYSA-N 0.000 claims 1
- ZZLTWFDIUYWZGU-UHFFFAOYSA-N 2-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methylamino]ethanol Chemical compound C1=C(F)C=C2OC(CNCCO)COC2=C1 ZZLTWFDIUYWZGU-UHFFFAOYSA-N 0.000 claims 1
- CPNKZXYIKWKIHG-VIFPVBQESA-N 2-[[(3s)-6-(trifluoromethyl)-2,3-dihydro-1,4-benzodioxin-3-yl]methylamino]ethanol Chemical compound C1=C(C(F)(F)F)C=C2O[C@@H](CNCCO)COC2=C1 CPNKZXYIKWKIHG-VIFPVBQESA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 1
- XHTNPXVQNOJXHM-UHFFFAOYSA-N 4-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]morpholine Chemical compound O1C2=CC(F)=CC(F)=C2OCC1CN1CCOCC1 XHTNPXVQNOJXHM-UHFFFAOYSA-N 0.000 claims 1
- YGXQSDSLABBTND-UHFFFAOYSA-N 4-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]morpholine Chemical compound O1C2=CC(F)=CC=C2OCC1CN1CCOCC1 YGXQSDSLABBTND-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010013654 Drug abuse Diseases 0.000 claims 1
- 208000014094 Dystonic disease Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 206010020852 Hypertonia Diseases 0.000 claims 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- 208000016285 Movement disease Diseases 0.000 claims 1
- 208000029726 Neurodevelopmental disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000027089 Parkinsonian disease Diseases 0.000 claims 1
- 206010034010 Parkinsonism Diseases 0.000 claims 1
- 206010044565 Tremor Diseases 0.000 claims 1
- GPEBOLJUGOONAG-UHFFFAOYSA-N [3-(azetidin-1-ylmethyl)-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound O1C2=CC(OS(=O)(=O)C(F)(F)F)=CC=C2OCC1CN1CCC1 GPEBOLJUGOONAG-UHFFFAOYSA-N 0.000 claims 1
- VENGEZHCJUQOSJ-UHFFFAOYSA-N [3-(butylaminomethyl)-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C=C2OC(CNCCCC)COC2=C1 VENGEZHCJUQOSJ-UHFFFAOYSA-N 0.000 claims 1
- BGCWSQTYHWGHLV-UHFFFAOYSA-N [3-(diethylaminomethyl)-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C=C2OC(CN(CC)CC)COC2=C1 BGCWSQTYHWGHLV-UHFFFAOYSA-N 0.000 claims 1
- UANWTDZKXIKEEH-UHFFFAOYSA-N [3-(ethylaminomethyl)-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C=C2OC(CNCC)COC2=C1 UANWTDZKXIKEEH-UHFFFAOYSA-N 0.000 claims 1
- ABVKPTBLJRKBFP-UHFFFAOYSA-N [3-(methylaminomethyl)-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C=C2OC(CNC)COC2=C1 ABVKPTBLJRKBFP-UHFFFAOYSA-N 0.000 claims 1
- PXRGVWBSIHQYEZ-UHFFFAOYSA-N [3-(morpholin-4-ylmethyl)-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound O1C2=CC(OS(=O)(=O)C(F)(F)F)=CC=C2OCC1CN1CCOCC1 PXRGVWBSIHQYEZ-UHFFFAOYSA-N 0.000 claims 1
- RFTBJAWMMSFRIS-UHFFFAOYSA-N [3-(piperidin-1-ylmethyl)-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound O1C2=CC(OS(=O)(=O)C(F)(F)F)=CC=C2OCC1CN1CCCCC1 RFTBJAWMMSFRIS-UHFFFAOYSA-N 0.000 claims 1
- MRQNVMIHSJAEKS-UHFFFAOYSA-N [3-(propylaminomethyl)-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C=C2OC(CNCCC)COC2=C1 MRQNVMIHSJAEKS-UHFFFAOYSA-N 0.000 claims 1
- QZUOJUTXJWIDGJ-UHFFFAOYSA-N [3-(pyrrolidin-1-ylmethyl)-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound O1C2=CC(OS(=O)(=O)C(F)(F)F)=CC=C2OCC1CN1CCCC1 QZUOJUTXJWIDGJ-UHFFFAOYSA-N 0.000 claims 1
- HKDMFSXFIXJPPY-UHFFFAOYSA-N [3-[(2-methoxyethylamino)methyl]-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C=C2OC(CNCCOC)COC2=C1 HKDMFSXFIXJPPY-UHFFFAOYSA-N 0.000 claims 1
- QLSLDJUZPKXPOG-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C=C2OC(CN(C)C)COC2=C1 QLSLDJUZPKXPOG-UHFFFAOYSA-N 0.000 claims 1
- FLQCVHZPKMRBCI-UHFFFAOYSA-N [3-[(dipropylamino)methyl]-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C=C2OC(CN(CCC)CCC)COC2=C1 FLQCVHZPKMRBCI-UHFFFAOYSA-N 0.000 claims 1
- QERZHFSAYSFMSV-UHFFFAOYSA-N [3-[(prop-2-enylamino)methyl]-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound O1CC(CNCC=C)OC2=CC(OS(=O)(=O)C(F)(F)F)=CC=C21 QERZHFSAYSFMSV-UHFFFAOYSA-N 0.000 claims 1
- RAYSQEXWHTZEMM-UHFFFAOYSA-N [3-[[ethyl(methyl)amino]methyl]-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C=C2OC(CN(C)CC)COC2=C1 RAYSQEXWHTZEMM-UHFFFAOYSA-N 0.000 claims 1
- KHQVPYNUBWQVEM-UHFFFAOYSA-N [3-[[ethyl(propyl)amino]methyl]-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C=C2OC(CN(CC)CCC)COC2=C1 KHQVPYNUBWQVEM-UHFFFAOYSA-N 0.000 claims 1
- SGOXCKIEQLUNAQ-UHFFFAOYSA-N [3-[[methyl(propyl)amino]methyl]-2,3-dihydro-1,4-benzodioxin-6-yl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C=C2OC(CN(C)CCC)COC2=C1 SGOXCKIEQLUNAQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 208000029560 autism spectrum disease Diseases 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 206010008129 cerebral palsy Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000010118 dystonia Diseases 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- WJJRUXPCWNDDAI-UHFFFAOYSA-N n-[(5,6-difluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]propan-1-amine Chemical compound C1=C(F)C(F)=C2OC(CNCCC)COC2=C1 WJJRUXPCWNDDAI-UHFFFAOYSA-N 0.000 claims 1
- VTGBDNOYSSIEFQ-UHFFFAOYSA-N n-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-2-methoxyethanamine Chemical compound C1=C(F)C=C2OC(CNCCOC)COC2=C1F VTGBDNOYSSIEFQ-UHFFFAOYSA-N 0.000 claims 1
- ZLDBUHGBEIEHTL-UHFFFAOYSA-N n-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-2-methylpropan-1-amine Chemical compound C1=C(F)C=C2OC(CNCC(C)C)COC2=C1F ZLDBUHGBEIEHTL-UHFFFAOYSA-N 0.000 claims 1
- ZVJDBJZJCNRJPZ-UHFFFAOYSA-N n-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-3-fluoropropan-1-amine Chemical compound C1=C(F)C=C2OC(CNCCCF)COC2=C1F ZVJDBJZJCNRJPZ-UHFFFAOYSA-N 0.000 claims 1
- HEECSUCPKVBYSV-UHFFFAOYSA-N n-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-n-ethylethanamine Chemical compound C1=C(F)C=C2OC(CN(CC)CC)COC2=C1F HEECSUCPKVBYSV-UHFFFAOYSA-N 0.000 claims 1
- WDHORUOUZQIRKO-UHFFFAOYSA-N n-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-n-ethylpropan-1-amine Chemical compound C1=C(F)C=C2OC(CN(CC)CCC)COC2=C1F WDHORUOUZQIRKO-UHFFFAOYSA-N 0.000 claims 1
- LKXSSGAJSWXZBM-UHFFFAOYSA-N n-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-n-methylethanamine Chemical compound C1=C(F)C=C2OC(CN(C)CC)COC2=C1F LKXSSGAJSWXZBM-UHFFFAOYSA-N 0.000 claims 1
- TUHVYESZOHKQNB-UHFFFAOYSA-N n-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-n-methylpropan-1-amine Chemical compound C1=C(F)C=C2OC(CN(C)CCC)COC2=C1F TUHVYESZOHKQNB-UHFFFAOYSA-N 0.000 claims 1
- FEKOYOSANQQHAR-UHFFFAOYSA-N n-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-n-propylpropan-1-amine Chemical compound C1=C(F)C=C2OC(CN(CCC)CCC)COC2=C1F FEKOYOSANQQHAR-UHFFFAOYSA-N 0.000 claims 1
- GFSKMSXXGZUWNY-UHFFFAOYSA-N n-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]butan-1-amine Chemical compound C1=C(F)C=C2OC(CNCCCC)COC2=C1F GFSKMSXXGZUWNY-UHFFFAOYSA-N 0.000 claims 1
- IXZFVGLMTMNXMC-UHFFFAOYSA-N n-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]ethanamine Chemical compound C1=C(F)C=C2OC(CNCC)COC2=C1F IXZFVGLMTMNXMC-UHFFFAOYSA-N 0.000 claims 1
- QNOYMWXEHDDNGA-UHFFFAOYSA-N n-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]prop-2-en-1-amine Chemical compound O1CC(CNCC=C)OC2=CC(F)=CC(F)=C21 QNOYMWXEHDDNGA-UHFFFAOYSA-N 0.000 claims 1
- WHSZFIDYICRXMV-UHFFFAOYSA-N n-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]propan-1-amine Chemical compound C1=C(F)C=C2OC(CNCCC)COC2=C1F WHSZFIDYICRXMV-UHFFFAOYSA-N 0.000 claims 1
- ABPWPAYSLIWTFO-UHFFFAOYSA-N n-[(5,7-difluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]propan-2-amine Chemical compound C1=C(F)C=C2OC(CNC(C)C)COC2=C1F ABPWPAYSLIWTFO-UHFFFAOYSA-N 0.000 claims 1
- JKGBIMGWEKEAFQ-UHFFFAOYSA-N n-[(6,7-difluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]propan-1-amine Chemical compound FC1=C(F)C=C2OC(CNCCC)COC2=C1 JKGBIMGWEKEAFQ-UHFFFAOYSA-N 0.000 claims 1
- LEAMJZVODXCHOO-UHFFFAOYSA-N n-[(6-chloro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]propan-1-amine Chemical compound C1=C(Cl)C=C2OC(CNCCC)COC2=C1 LEAMJZVODXCHOO-UHFFFAOYSA-N 0.000 claims 1
- SJRBBBPDSWJPAK-UHFFFAOYSA-N n-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]-2-methoxyethanamine Chemical compound C1=C(F)C=C2OC(CNCCOC)COC2=C1 SJRBBBPDSWJPAK-UHFFFAOYSA-N 0.000 claims 1
- AOPFMRVOQSBUJU-UHFFFAOYSA-N n-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]-n-methylethanamine Chemical compound C1=C(F)C=C2OC(CN(C)CC)COC2=C1 AOPFMRVOQSBUJU-UHFFFAOYSA-N 0.000 claims 1
- WNRNHXBOGLJKEH-UHFFFAOYSA-N n-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]-n-methylpropan-1-amine Chemical compound C1=C(F)C=C2OC(CN(C)CCC)COC2=C1 WNRNHXBOGLJKEH-UHFFFAOYSA-N 0.000 claims 1
- WWHKWTFUTVWUHN-UHFFFAOYSA-N n-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]-n-propylpropan-1-amine Chemical compound C1=C(F)C=C2OC(CN(CCC)CCC)COC2=C1 WWHKWTFUTVWUHN-UHFFFAOYSA-N 0.000 claims 1
- FNWWKADKLZVKST-UHFFFAOYSA-N n-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]butan-1-amine Chemical compound C1=C(F)C=C2OC(CNCCCC)COC2=C1 FNWWKADKLZVKST-UHFFFAOYSA-N 0.000 claims 1
- ZBQXNRLGHYYTLH-UHFFFAOYSA-N n-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]ethanamine Chemical compound C1=C(F)C=C2OC(CNCC)COC2=C1 ZBQXNRLGHYYTLH-UHFFFAOYSA-N 0.000 claims 1
- NPRDWMPHZXSOSR-UHFFFAOYSA-N n-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]prop-2-en-1-amine Chemical compound O1CC(CNCC=C)OC2=CC(F)=CC=C21 NPRDWMPHZXSOSR-UHFFFAOYSA-N 0.000 claims 1
- KNQFBLKUTCMJMX-UHFFFAOYSA-N n-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]propan-1-amine Chemical compound C1=C(F)C=C2OC(CNCCC)COC2=C1 KNQFBLKUTCMJMX-UHFFFAOYSA-N 0.000 claims 1
- YEGXDDBJOIOWRS-JTQLQIEISA-N n-[[(3s)-6-(trifluoromethyl)-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound C1=C(C(F)(F)F)C=C2O[C@@H](CNCCC)COC2=C1 YEGXDDBJOIOWRS-JTQLQIEISA-N 0.000 claims 1
- YTFSDHSPLJHIJI-JTQLQIEISA-N n-[[(3s)-6-bromo-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound C1=C(Br)C=C2O[C@@H](CNCCC)COC2=C1 YTFSDHSPLJHIJI-JTQLQIEISA-N 0.000 claims 1
- ZBBRVOIFJABZHP-UHFFFAOYSA-N n-ethyl-n-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]ethanamine Chemical compound C1=C(F)C=C2OC(CN(CC)CC)COC2=C1 ZBBRVOIFJABZHP-UHFFFAOYSA-N 0.000 claims 1
- SJAVNRHXJLOARU-UHFFFAOYSA-N n-ethyl-n-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]propan-1-amine Chemical compound C1=C(F)C=C2OC(CN(CC)CCC)COC2=C1 SJAVNRHXJLOARU-UHFFFAOYSA-N 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 208000012201 sexual and gender identity disease Diseases 0.000 claims 1
- 208000015891 sexual disease Diseases 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
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| DKPA200800599 | 2008-04-29 | ||
| DKPA200800599 | 2008-04-29 | ||
| US4905808P | 2008-04-30 | 2008-04-30 | |
| US61/049,058 | 2008-04-30 | ||
| PCT/EP2009/055139 WO2009133109A1 (en) | 2008-04-29 | 2009-04-28 | Modulators of dopamine neurotransmission |
Publications (2)
| Publication Number | Publication Date |
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| JP2011519839A JP2011519839A (ja) | 2011-07-14 |
| JP2011519839A5 true JP2011519839A5 (https=) | 2012-06-21 |
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| JP2011506690A Abandoned JP2011519839A (ja) | 2008-04-29 | 2009-04-28 | ドーパミン神経伝達のモジュレーター |
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| US (1) | US20110105462A1 (https=) |
| EP (1) | EP2271635A1 (https=) |
| JP (1) | JP2011519839A (https=) |
| WO (1) | WO2009133109A1 (https=) |
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| AU2009242092A1 (en) | 2008-04-29 | 2009-11-05 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Modulators of dopamine neurotransmission |
| EP2271638B1 (en) * | 2008-04-29 | 2011-08-31 | NSAB, Filial af NeuroSearch Sweden AB, Sverige | Modulators of dopamine neurotransmission |
| EP2699543B1 (en) | 2011-04-19 | 2016-03-02 | Integrative Research Laboratories Sweden AB | Novel modulators of cortical dopaminergic- and nmda-receptor-mediated glutamatergic neurotransmission |
| FI3976581T3 (fi) | 2019-05-24 | 2024-01-31 | Irl 790 Ab | [2-(3-fluori-5-metaani-sulfonyylifenoksi)etyyli](propyli)amiinin viinihapposuolat |
| CN115475161B (zh) * | 2022-10-28 | 2023-08-29 | 五邑大学 | 吡喃类化合物在制备用于预防和/或治疗帕金森病药物中的应用 |
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| US2906757A (en) * | 1959-09-29 | Their preparation | ||
| US3058980A (en) * | 1962-10-16 | Substitution products of benzo- | ||
| GB565753A (en) * | 1943-03-23 | 1944-11-27 | Berkel & Parnall Mach Mfg Co | Improvements relating to slicing machines |
| DE1110175B (de) * | 1957-01-08 | 1961-07-06 | Rhone Poulenc Sa | Verfahren zur Herstellung von Benzodioxanderivaten |
| US5126366A (en) * | 1991-06-21 | 1992-06-30 | American Home Products Corporation | Aminophenoxyalkyl derivatives of benzodioxan |
| US5166367A (en) * | 1991-06-21 | 1992-11-24 | American Home Products Corporation | Antipsychotic benzodioxan derivatives |
| US5189171A (en) * | 1991-06-21 | 1993-02-23 | American Home Products Corporation | Antipsychotic benzodioxan derivatives |
| DE4135474A1 (de) * | 1991-10-28 | 1993-04-29 | Bayer Ag | 2-aminomethyl-chromane |
| US5235055A (en) * | 1992-09-02 | 1993-08-10 | American Home Products Corporation | Antipsychotic quinoline derivatives of benzodioxanmethylamine |
| US5245051A (en) * | 1992-09-03 | 1993-09-14 | American Home Products Corporation | Antipsychotic chroman derivatives of benzodioxanmethylamine |
| US5663194A (en) * | 1995-07-25 | 1997-09-02 | Mewshaw; Richard E. | Chroman-2-ylmethylamino derivatives |
| AR004229A1 (es) * | 1995-11-06 | 1998-11-04 | Wyeth Corp | Derivados indolalquilo de benzodioxanmetilamina y su uso para preparar medicamentos |
| FR2791675B1 (fr) * | 1999-03-30 | 2001-05-04 | Synthelabo | Derives de n-[2-(4-aminophenyl) ethyl] -2,3-dihydro-1,4- benzodioxinne-2-methanamine, leur preparation et leur application en therapeutique |
| SE9904723D0 (sv) * | 1999-12-22 | 1999-12-22 | Carlsson A Research Ab | New modulators of dopamine neurotransmission II |
| SE9904724D0 (sv) * | 1999-12-22 | 1999-12-22 | Carlsson A Research Ab | New modulators of dopamine neurotransmission I |
| GB0007376D0 (en) * | 2000-03-28 | 2000-05-17 | Knoll Ag | Therapeutic agents |
| EP1678121A4 (en) * | 2003-10-24 | 2007-07-25 | Exelixis Inc | MODULATORS OF TAO KINASES AND METHODS OF USE |
| KR100823805B1 (ko) * | 2004-05-05 | 2008-04-21 | 에프. 호프만-라 로슈 아게 | 5-ｈｔ6 수용체, 5-ｈｔ2ａ 수용체 또는 둘다를 조절하기에유용한 아릴설포닐 벤조다이옥산 |
| DE602005021641D1 (de) * | 2004-06-08 | 2010-07-15 | Nsab, Filial Af Neurosearch Sweden Ab | Neue disubstituierte phenylpiperidine und piperazine als modulatoren der dopamin-neurotransmission |
| AR049646A1 (es) * | 2004-06-16 | 2006-08-23 | Janssen Pharmaceutica Nv | Derivados de sulfamato y sulfamida utiles para el tratamiento de la epilepsia y trastornos relacionados |
| MY147767A (en) * | 2004-06-16 | 2013-01-31 | Janssen Pharmaceutica Nv | Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders |
| US7713954B2 (en) * | 2004-09-30 | 2010-05-11 | Roche Palo Alto Llc | Compositions and methods for treating cognitive disorders |
| AU2006239930A1 (en) * | 2005-04-22 | 2006-11-02 | Wyeth | Benzodioxane and benzodioxolane derivatives and uses thereof |
| SE529246C2 (sv) * | 2005-10-13 | 2007-06-12 | Neurosearch Sweden Ab | Nya disubstituerade fenyl-piperidiner som modulatorer för dopaminneurotransmission |
| US8691867B2 (en) * | 2005-12-19 | 2014-04-08 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of substance abuse and addiction |
| US8716231B2 (en) * | 2005-12-19 | 2014-05-06 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of pain |
| US20070155823A1 (en) * | 2005-12-19 | 2007-07-05 | Smith-Swintosky Virginia L | Use of benzo-fused heterocycle sulfamide derivatives as neuroprotective agents |
| US8492431B2 (en) * | 2005-12-19 | 2013-07-23 | Janssen Pharmaceutica, N.V. | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of obesity |
| US20070155827A1 (en) * | 2005-12-19 | 2007-07-05 | Smith-Swintosky Virginia L | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of depression |
| US8937096B2 (en) * | 2005-12-19 | 2015-01-20 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocyle sulfamide derivatives for the treatment of mania and bipolar disorder |
| US20070155824A1 (en) * | 2005-12-19 | 2007-07-05 | Smith-Swintosky Virginia L | Use of benzo-fused heterocycle sulfamide derivatives for disease modification / epileptogenesis |
| WO2007120596A1 (en) * | 2006-04-12 | 2007-10-25 | Wyeth | DIHYDRO[1,4]DIOXINO[2,3-e]INDAZOLE DERIVATIVES AS 5-HYDROXYTRYPTAMINE-6 LIGANDS |
| AR060493A1 (es) * | 2006-04-18 | 2008-06-18 | Wyeth Corp | Derivados de benzodioxano y benzodioxolano. procesos de obtencion. |
| EP2026790A2 (en) * | 2006-05-19 | 2009-02-25 | Janssen Pharmaceutica, N.V. | Co-therapy for the treatment of epilepsy and related disorders |
| TWI457122B (zh) * | 2007-07-20 | 2014-10-21 | Orion Corp | 作為用於治療周邊和中央神經系統疾病之alpha2C拮抗劑的2,3－二氫苯並[1,4]戴奧辛－2－基甲基衍生物 |
| EP2271638B1 (en) * | 2008-04-29 | 2011-08-31 | NSAB, Filial af NeuroSearch Sweden AB, Sverige | Modulators of dopamine neurotransmission |
| AU2009242092A1 (en) * | 2008-04-29 | 2009-11-05 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Modulators of dopamine neurotransmission |
-
2009
- 2009-04-28 WO PCT/EP2009/055139 patent/WO2009133109A1/en not_active Ceased
- 2009-04-28 JP JP2011506690A patent/JP2011519839A/ja not_active Abandoned
- 2009-04-28 EP EP09738153A patent/EP2271635A1/en not_active Withdrawn
- 2009-04-28 US US12/990,059 patent/US20110105462A1/en not_active Abandoned
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