RU2010141964A - Модуляторы дофаминовой нейротрансмиссии - Google Patents
Модуляторы дофаминовой нейротрансмиссии Download PDFInfo
- Publication number
- RU2010141964A RU2010141964A RU2010141964/04A RU2010141964A RU2010141964A RU 2010141964 A RU2010141964 A RU 2010141964A RU 2010141964/04 A RU2010141964/04 A RU 2010141964/04A RU 2010141964 A RU2010141964 A RU 2010141964A RU 2010141964 A RU2010141964 A RU 2010141964A
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- dihydro
- methylsulfonyl
- benzodioxin
- amine
- Prior art date
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- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title 2
- 229960003638 dopamine Drugs 0.000 title 1
- 230000005062 synaptic transmission Effects 0.000 title 1
- 150000001204 N-oxides Chemical class 0.000 claims abstract 19
- 150000001875 compounds Chemical class 0.000 claims abstract 19
- 239000000203 mixture Substances 0.000 claims abstract 19
- 150000003839 salts Chemical class 0.000 claims abstract 19
- -1 3,3,3-trifluoropropyl Chemical group 0.000 claims abstract 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 14
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000028017 Psychotic disease Diseases 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 210000003169 central nervous system Anatomy 0.000 claims 3
- 230000010249 dopaminergic function Effects 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000012661 Dyskinesia Diseases 0.000 claims 2
- 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 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229960004502 levodopa Drugs 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- NFLCJVNIHXOFPL-VIFPVBQESA-N n-[[(2s)-5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCCC)COC2=C1F NFLCJVNIHXOFPL-VIFPVBQESA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- ACSYJWICJIGNLM-UHFFFAOYSA-N 1-(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)-n,n-dimethylmethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(C)C)COC2=C1F ACSYJWICJIGNLM-UHFFFAOYSA-N 0.000 claims 1
- CCAIFRVSMWLNEE-UHFFFAOYSA-N 1-(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)-n-methylmethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNC)COC2=C1F CCAIFRVSMWLNEE-UHFFFAOYSA-N 0.000 claims 1
- PEOWPJFIOSDEAU-QMMMGPOBSA-N 1-[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]-n,n-dimethylmethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CN(C)C)COC2=C1Cl PEOWPJFIOSDEAU-QMMMGPOBSA-N 0.000 claims 1
- RZUBLNVSYWTUNT-ZETCQYMHSA-N 1-[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]-n-methylmethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNC)COC2=C1Cl RZUBLNVSYWTUNT-ZETCQYMHSA-N 0.000 claims 1
- CCAIFRVSMWLNEE-ZETCQYMHSA-N 1-[(2s)-5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]-n-methylmethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNC)COC2=C1F CCAIFRVSMWLNEE-ZETCQYMHSA-N 0.000 claims 1
- NUIPPHWBYVORHW-UHFFFAOYSA-N 1-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]azetidine Chemical compound O1C2=CC(S(=O)(=O)C)=CC(F)=C2OCC1CN1CCC1 NUIPPHWBYVORHW-UHFFFAOYSA-N 0.000 claims 1
- NWDJQBPQRBURCK-UHFFFAOYSA-N 1-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]pyrrolidine Chemical compound O1C2=CC(S(=O)(=O)C)=CC(F)=C2OCC1CN1CCCC1 NWDJQBPQRBURCK-UHFFFAOYSA-N 0.000 claims 1
- VWZYPYQIYSAIMK-UHFFFAOYSA-N 1-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]azetidine Chemical compound O1C2=CC(S(=O)(=O)C)=CC=C2OCC1CN1CCC1 VWZYPYQIYSAIMK-UHFFFAOYSA-N 0.000 claims 1
- YMYCYPLFBJAPSA-UHFFFAOYSA-N 1-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]piperidine Chemical compound O1C2=CC(S(=O)(=O)C)=CC=C2OCC1CN1CCCCC1 YMYCYPLFBJAPSA-UHFFFAOYSA-N 0.000 claims 1
- MZCVJTWBVVJSPU-UHFFFAOYSA-N 1-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]pyrrolidine Chemical compound O1C2=CC(S(=O)(=O)C)=CC=C2OCC1CN1CCCC1 MZCVJTWBVVJSPU-UHFFFAOYSA-N 0.000 claims 1
- MDPRCZLYVCMHCH-UHFFFAOYSA-N 1-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]azetidine Chemical compound O1C2=CC(S(=O)(=O)C)=CC=C2CCC1CN1CCC1 MDPRCZLYVCMHCH-UHFFFAOYSA-N 0.000 claims 1
- DRKJABUWGLAFKY-UHFFFAOYSA-N 1-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]piperidine Chemical compound O1C2=CC(S(=O)(=O)C)=CC=C2CCC1CN1CCCCC1 DRKJABUWGLAFKY-UHFFFAOYSA-N 0.000 claims 1
- PQZPJSJBBOGKFA-UHFFFAOYSA-N 1-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]pyrrolidine Chemical compound O1C2=CC(S(=O)(=O)C)=CC=C2CCC1CN1CCCC1 PQZPJSJBBOGKFA-UHFFFAOYSA-N 0.000 claims 1
- UPPBQQQGJDYDAE-VIFPVBQESA-N 1-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]azetidine Chemical compound C([C@H]1COC2=C(Cl)C=C(C=C2O1)S(=O)(=O)C)N1CCC1 UPPBQQQGJDYDAE-VIFPVBQESA-N 0.000 claims 1
- KMNLDFWCAPNJMO-NSHDSACASA-N 1-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]piperidine Chemical compound C([C@H]1COC2=C(Cl)C=C(C=C2O1)S(=O)(=O)C)N1CCCCC1 KMNLDFWCAPNJMO-NSHDSACASA-N 0.000 claims 1
- JZQRHSKASKRFLH-JTQLQIEISA-N 1-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]pyrrolidine Chemical compound C([C@H]1COC2=C(Cl)C=C(C=C2O1)S(=O)(=O)C)N1CCCC1 JZQRHSKASKRFLH-JTQLQIEISA-N 0.000 claims 1
- YMYCYPLFBJAPSA-GFCCVEGCSA-N 1-[[(3r)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]piperidine Chemical compound C([C@@H]1COC2=CC=C(C=C2O1)S(=O)(=O)C)N1CCCCC1 YMYCYPLFBJAPSA-GFCCVEGCSA-N 0.000 claims 1
- YMYCYPLFBJAPSA-LBPRGKRZSA-N 1-[[(3s)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]piperidine Chemical compound C([C@H]1COC2=CC=C(C=C2O1)S(=O)(=O)C)N1CCCCC1 YMYCYPLFBJAPSA-LBPRGKRZSA-N 0.000 claims 1
- OGXFHSKZILWLNO-NSHDSACASA-N 2,2-dimethyl-n-[[(3s)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCC(C)(C)C)COC2=C1 OGXFHSKZILWLNO-NSHDSACASA-N 0.000 claims 1
- CGUICIFMMKFYRR-UHFFFAOYSA-N 2-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methylamino]ethanol Chemical compound O1CC(CNCCO)OC2=CC(S(=O)(=O)C)=CC(F)=C21 CGUICIFMMKFYRR-UHFFFAOYSA-N 0.000 claims 1
- AYRSCENJQDTKKW-UHFFFAOYSA-N 2-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methylamino]ethanol Chemical compound O1CC(CNCCO)OC2=CC(S(=O)(=O)C)=CC=C21 AYRSCENJQDTKKW-UHFFFAOYSA-N 0.000 claims 1
- UFXCPZGYIFTGBV-UHFFFAOYSA-N 2-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methylamino]ethanol Chemical compound C1CC(CNCCO)OC2=CC(S(=O)(=O)C)=CC=C21 UFXCPZGYIFTGBV-UHFFFAOYSA-N 0.000 claims 1
- QTSMGAUELLRMTQ-QMMMGPOBSA-N 2-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methylamino]ethanol Chemical compound O1C[C@H](CNCCO)OC2=CC(S(=O)(=O)C)=CC(Cl)=C21 QTSMGAUELLRMTQ-QMMMGPOBSA-N 0.000 claims 1
- PZGIGAYLGVNPAM-UHFFFAOYSA-N 2-methoxy-n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCCOC)COC2=C1 PZGIGAYLGVNPAM-UHFFFAOYSA-N 0.000 claims 1
- DTYYIKTYZUMRGL-UHFFFAOYSA-N 2-methoxy-n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCCOC)CCC2=C1 DTYYIKTYZUMRGL-UHFFFAOYSA-N 0.000 claims 1
- XZLUXENLKSWQTA-UHFFFAOYSA-N 2-methyl-n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCC(C)C)COC2=C1 XZLUXENLKSWQTA-UHFFFAOYSA-N 0.000 claims 1
- NJOVSKINYLLZJB-UHFFFAOYSA-N 2-methyl-n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCC(C)C)CCC2=C1 NJOVSKINYLLZJB-UHFFFAOYSA-N 0.000 claims 1
- XZLUXENLKSWQTA-LLVKDONJSA-N 2-methyl-n-[[(3r)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@H](CNCC(C)C)COC2=C1 XZLUXENLKSWQTA-LLVKDONJSA-N 0.000 claims 1
- XZLUXENLKSWQTA-NSHDSACASA-N 2-methyl-n-[[(3s)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCC(C)C)COC2=C1 XZLUXENLKSWQTA-NSHDSACASA-N 0.000 claims 1
- ICGHWPFOUQWXGY-QMMMGPOBSA-N 3,3,3-trifluoro-n-[[(2s)-5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]propan-1-amine Chemical compound O1C[C@H](CNCCC(F)(F)F)OC2=CC(S(=O)(=O)C)=CC(F)=C21 ICGHWPFOUQWXGY-QMMMGPOBSA-N 0.000 claims 1
- YNQIUDXOEYHCHG-VIFPVBQESA-N 3,3,3-trifluoro-n-[[(3s)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound O1C[C@H](CNCCC(F)(F)F)OC2=CC(S(=O)(=O)C)=CC=C21 YNQIUDXOEYHCHG-VIFPVBQESA-N 0.000 claims 1
- HMTHTJXBHPRKIF-ZGTCLIOFSA-N 3-methyl-1-[[(3r)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]piperidine Chemical compound C1C(C)CCCN1C[C@H]1OC2=CC(S(C)(=O)=O)=CC=C2OC1 HMTHTJXBHPRKIF-ZGTCLIOFSA-N 0.000 claims 1
- QIMAGFLOKOCZDJ-UHFFFAOYSA-N 4-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]morpholine Chemical compound O1C2=CC(S(=O)(=O)C)=CC(F)=C2OCC1CN1CCOCC1 QIMAGFLOKOCZDJ-UHFFFAOYSA-N 0.000 claims 1
- KOFNOWRXIDSMAA-UHFFFAOYSA-N 4-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]morpholine Chemical compound O1C2=CC(S(=O)(=O)C)=CC=C2OCC1CN1CCOCC1 KOFNOWRXIDSMAA-UHFFFAOYSA-N 0.000 claims 1
- JDCIBHCASSGJOB-UHFFFAOYSA-N 4-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]morpholine Chemical compound O1C2=CC(S(=O)(=O)C)=CC=C2CCC1CN1CCOCC1 JDCIBHCASSGJOB-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000020706 Autistic disease Diseases 0.000 claims 1
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- 206010020852 Hypertonia Diseases 0.000 claims 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
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- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 206010008129 cerebral palsy Diseases 0.000 claims 1
- 208000010877 cognitive disease 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
- 230000000642 iatrogenic effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- QVVXSAIFIWLFAB-UHFFFAOYSA-N n,n-dimethyl-1-(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(C)C)CCC2=C1 QVVXSAIFIWLFAB-UHFFFAOYSA-N 0.000 claims 1
- IWCVJTWXFIQFKV-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-2-methoxyethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCCOC)COC2=C1F IWCVJTWXFIQFKV-UHFFFAOYSA-N 0.000 claims 1
- JMVMQHJFSAOHCU-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-2-methylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCC(C)C)COC2=C1F JMVMQHJFSAOHCU-UHFFFAOYSA-N 0.000 claims 1
- KRJUEVQPCIMMHI-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-n-methylethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(C)CC)COC2=C1F KRJUEVQPCIMMHI-UHFFFAOYSA-N 0.000 claims 1
- COZAOGJDNDUOHZ-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-n-methylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(C)CCC)COC2=C1F COZAOGJDNDUOHZ-UHFFFAOYSA-N 0.000 claims 1
- HGYAEVSVNVKZRE-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-n-propylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(CCC)CCC)COC2=C1F HGYAEVSVNVKZRE-UHFFFAOYSA-N 0.000 claims 1
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- WQSMDWKWHVKCSV-UHFFFAOYSA-N n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]-n-propylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(CCC)CCC)COC2=C1 WQSMDWKWHVKCSV-UHFFFAOYSA-N 0.000 claims 1
- QYNCLOCTEVTRJW-UHFFFAOYSA-N n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]butan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCCCC)COC2=C1 QYNCLOCTEVTRJW-UHFFFAOYSA-N 0.000 claims 1
- XMHPZKPXIAVGLB-UHFFFAOYSA-N n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCC)COC2=C1 XMHPZKPXIAVGLB-UHFFFAOYSA-N 0.000 claims 1
- KXLHMDZOCIYVOU-UHFFFAOYSA-N n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]prop-2-en-1-amine Chemical compound O1CC(CNCC=C)OC2=CC(S(=O)(=O)C)=CC=C21 KXLHMDZOCIYVOU-UHFFFAOYSA-N 0.000 claims 1
- MAMVDUBLWPVXIQ-UHFFFAOYSA-N n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCCC)COC2=C1 MAMVDUBLWPVXIQ-UHFFFAOYSA-N 0.000 claims 1
- AUAAOFMSOHILNS-UHFFFAOYSA-N n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]propan-2-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNC(C)C)COC2=C1 AUAAOFMSOHILNS-UHFFFAOYSA-N 0.000 claims 1
- JUKYRQPWRKYMEH-UHFFFAOYSA-N n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]butan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCCCC)CCC2=C1 JUKYRQPWRKYMEH-UHFFFAOYSA-N 0.000 claims 1
- WIVADSNAUYDWFY-UHFFFAOYSA-N n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCC)CCC2=C1 WIVADSNAUYDWFY-UHFFFAOYSA-N 0.000 claims 1
- DPQXIDNQWGFQAA-UHFFFAOYSA-N n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]prop-2-en-1-amine Chemical compound C1CC(CNCC=C)OC2=CC(S(=O)(=O)C)=CC=C21 DPQXIDNQWGFQAA-UHFFFAOYSA-N 0.000 claims 1
- BHNSRSOJVPQCHH-UHFFFAOYSA-N n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]propan-2-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNC(C)C)CCC2=C1 BHNSRSOJVPQCHH-UHFFFAOYSA-N 0.000 claims 1
- VLRJTIYKLYDRSN-JTQLQIEISA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]-2,2-dimethylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCC(C)(C)C)COC2=C1Cl VLRJTIYKLYDRSN-JTQLQIEISA-N 0.000 claims 1
- VHIGPNQUCBEFFA-VIFPVBQESA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]-2-methoxyethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCCOC)COC2=C1Cl VHIGPNQUCBEFFA-VIFPVBQESA-N 0.000 claims 1
- WVGMRJOHWGRXDB-JTQLQIEISA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]-2-methylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCC(C)C)COC2=C1Cl WVGMRJOHWGRXDB-JTQLQIEISA-N 0.000 claims 1
- MNWSMMIMVHLCNW-VIFPVBQESA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]-3-fluoropropan-1-amine Chemical compound O1C[C@H](CNCCCF)OC2=CC(S(=O)(=O)C)=CC(Cl)=C21 MNWSMMIMVHLCNW-VIFPVBQESA-N 0.000 claims 1
- KYUKFUXUFQAWEO-JTQLQIEISA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]-n-ethylethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CN(CC)CC)COC2=C1Cl KYUKFUXUFQAWEO-JTQLQIEISA-N 0.000 claims 1
- OSKPEFIPFULJMA-NSHDSACASA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]-n-ethylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CN(CC)CCC)COC2=C1Cl OSKPEFIPFULJMA-NSHDSACASA-N 0.000 claims 1
- NEYQEXHISQFWSO-VIFPVBQESA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]-n-methylethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CN(C)CC)COC2=C1Cl NEYQEXHISQFWSO-VIFPVBQESA-N 0.000 claims 1
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- NGWLBYMNHLEBMB-VIFPVBQESA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCCC)COC2=C1Cl NGWLBYMNHLEBMB-VIFPVBQESA-N 0.000 claims 1
- DENNJTQQOMENLP-VIFPVBQESA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]propan-2-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNC(C)C)COC2=C1Cl DENNJTQQOMENLP-VIFPVBQESA-N 0.000 claims 1
- CYBYLIMSZIVQTB-QMMMGPOBSA-N n-[[(2s)-5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCC)COC2=C1F CYBYLIMSZIVQTB-QMMMGPOBSA-N 0.000 claims 1
- MAMVDUBLWPVXIQ-SNVBAGLBSA-N n-[[(3r)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@H](CNCCC)COC2=C1 MAMVDUBLWPVXIQ-SNVBAGLBSA-N 0.000 claims 1
- NCEOXFQEEQSDNM-QMMMGPOBSA-N n-[[(3s)-5-fluoro-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C(F)=C2O[C@@H](CNCC)COC2=C1 NCEOXFQEEQSDNM-QMMMGPOBSA-N 0.000 claims 1
- DWDCNTGCXVPWSD-QMMMGPOBSA-N n-[[(3s)-6-(trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]ethanamine Chemical compound C1=C(S(=O)(=O)C(F)(F)F)C=C2O[C@@H](CNCC)COC2=C1 DWDCNTGCXVPWSD-QMMMGPOBSA-N 0.000 claims 1
- KHWNHRMQYUBIMK-VIFPVBQESA-N n-[[(3s)-6-(trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound C1=C(S(=O)(=O)C(F)(F)F)C=C2O[C@@H](CNCCC)COC2=C1 KHWNHRMQYUBIMK-VIFPVBQESA-N 0.000 claims 1
- XMHPZKPXIAVGLB-VIFPVBQESA-N n-[[(3s)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCC)COC2=C1 XMHPZKPXIAVGLB-VIFPVBQESA-N 0.000 claims 1
- MAMVDUBLWPVXIQ-JTQLQIEISA-N n-[[(3s)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCCC)COC2=C1 MAMVDUBLWPVXIQ-JTQLQIEISA-N 0.000 claims 1
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- JSKTWSDFQLGSCS-UHFFFAOYSA-N n-ethyl-n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(CC)CC)CCC2=C1 JSKTWSDFQLGSCS-UHFFFAOYSA-N 0.000 claims 1
- XYKUQSBFOINJJP-UHFFFAOYSA-N n-ethyl-n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(CC)CCC)CCC2=C1 XYKUQSBFOINJJP-UHFFFAOYSA-N 0.000 claims 1
- WSUXMRJVCYPXQL-UHFFFAOYSA-N n-methyl-1-(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNC)COC2=C1 WSUXMRJVCYPXQL-UHFFFAOYSA-N 0.000 claims 1
- MGYNLGKVKLYWQS-UHFFFAOYSA-N n-methyl-1-(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNC)CCC2=C1 MGYNLGKVKLYWQS-UHFFFAOYSA-N 0.000 claims 1
- WSUXMRJVCYPXQL-QMMMGPOBSA-N n-methyl-1-[(3s)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methanamine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNC)COC2=C1 WSUXMRJVCYPXQL-QMMMGPOBSA-N 0.000 claims 1
- XSKZKXSGWYQLOS-UHFFFAOYSA-N n-methyl-n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(C)CCC)COC2=C1 XSKZKXSGWYQLOS-UHFFFAOYSA-N 0.000 claims 1
- DMEIURQIMNPMOQ-UHFFFAOYSA-N n-methyl-n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(C)CC)CCC2=C1 DMEIURQIMNPMOQ-UHFFFAOYSA-N 0.000 claims 1
- GTOBKTAKGUERFM-UHFFFAOYSA-N n-methyl-n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(C)CCC)CCC2=C1 GTOBKTAKGUERFM-UHFFFAOYSA-N 0.000 claims 1
- 230000008271 nervous system development Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 230000001272 neurogenic effect Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 201000000980 schizophrenia Diseases 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
- 238000001228 spectrum Methods 0.000 claims 1
- 201000009032 substance abuse Diseases 0.000 claims 1
- 231100000736 substance abuse Toxicity 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 claims 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 abstract 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical compound [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 abstract 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 abstract 2
- 108010081348 HRT1 protein Hairy Chemical group 0.000 abstract 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 abstract 2
- 101100533877 Hypocrea jecorina (strain QM6a) sor8 gene Proteins 0.000 abstract 2
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 2
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 abstract 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical group F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 abstract 2
- 125000000565 sulfonamide group Chemical group 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/20—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 hydrogenated in the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Psychology (AREA)
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- Anesthesiology (AREA)
- Hematology (AREA)
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- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Addiction (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200800598 | 2008-04-29 | ||
| DKPA200800598 | 2008-04-29 | ||
| US4905908P | 2008-04-30 | 2008-04-30 | |
| US61/049,059 | 2008-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2010141964A true RU2010141964A (ru) | 2012-06-10 |
Family
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Family Applications (1)
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| WO2009133110A1 (en) | 2008-04-29 | 2009-11-05 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Modulators of dopamine neurotransmission |
| JP2011519839A (ja) * | 2008-04-29 | 2011-07-14 | エヌエスエイビー、フィリアル アヴ ノイロサーチ スウェーデン エービー、スヴェーリエ | ドーパミン神経伝達のモジュレーター |
| CN102180856B (zh) * | 2011-03-01 | 2016-01-20 | 浙江华海药业股份有限公司 | 一种制备6-氟-3,4-二氢-2h-1-苯并吡喃-2-甲酸乙酯的方法 |
| US9006227B2 (en) | 2011-04-19 | 2015-04-14 | Integrative Research Laboratories Sweden Ab | Modulators of cortical dopaminergic- and NMDA-receptor-mediated glutamatergic neurotransmission |
| CN104350144B (zh) | 2012-05-23 | 2017-08-04 | 弗·哈夫曼-拉罗切有限公司 | 获得和使用内胚层和肝细胞的组合物和方法 |
| WO2015198850A1 (ja) | 2014-06-26 | 2015-12-30 | 住友化学株式会社 | フェノール化合物の製造方法 |
| US9125866B1 (en) | 2015-01-28 | 2015-09-08 | King Saud University | Antidepressant compounds |
| US10377703B2 (en) * | 2015-07-21 | 2019-08-13 | Sumitomo Chemical Company, Limited | Method for producing 4-(trifluoromethylsulfonyl)phenol compound |
| US12275694B2 (en) | 2019-05-24 | 2025-04-15 | Irl 790 Ab | Pharmaceutically acceptable salts of [2-(3-fluoro-5-methane-sulfonylphenoxy)ethyl](propyl)amine and uses thereof |
| AU2024229876A1 (en) * | 2023-03-01 | 2025-10-09 | Alexander Shulgin Research Institute, Inc. | Deuterated and fluorinated empathogens |
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| US2906757A (en) | 1959-09-29 | Their preparation | ||
| US3058980A (en) | 1962-10-16 | Substitution products of benzo- | ||
| DE1110175B (de) | 1957-01-08 | 1961-07-06 | Rhone Poulenc Sa | Verfahren zur Herstellung von Benzodioxanderivaten |
| JPS55124781A (en) * | 1979-03-20 | 1980-09-26 | Shionogi & Co Ltd | 1,4-benzdioxanesulfonamide derivative |
| US5236055A (en) * | 1991-03-13 | 1993-08-17 | Canadian Aging & Rehabilitation Product Development Corporation | Wheel with coaxial drive system mounted in the wheelhub field of the invention |
| US5166367A (en) | 1991-06-21 | 1992-11-24 | American Home Products Corporation | Antipsychotic benzodioxan derivatives |
| US5126366A (en) | 1991-06-21 | 1992-06-30 | American Home Products Corporation | Aminophenoxyalkyl derivatives of benzodioxan |
| 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 |
| GB9514380D0 (en) * | 1995-07-13 | 1995-09-13 | Knoll Ag | Therapeutic agents |
| US5663194A (en) | 1995-07-25 | 1997-09-02 | Mewshaw; Richard E. | Chroman-2-ylmethylamino derivatives |
| US5684039A (en) * | 1995-07-25 | 1997-11-04 | American Home Products Corporation | 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 |
| SE9904724D0 (sv) | 1999-12-22 | 1999-12-22 | Carlsson A Research Ab | New modulators of dopamine neurotransmission I |
| SE9904723D0 (sv) | 1999-12-22 | 1999-12-22 | Carlsson A Research Ab | New modulators of dopamine neurotransmission II |
| GB0007376D0 (en) | 2000-03-28 | 2000-05-17 | Knoll Ag | Therapeutic agents |
| EP1432696A1 (en) | 2001-10-04 | 2004-06-30 | Wyeth | Chroman derivatives as 5-hydroxytryptamine-6 ligands |
| TWI281470B (en) * | 2002-05-24 | 2007-05-21 | Elan Pharm Inc | Heterocyclic compounds which inhibit leukocyte adhesion mediated by alpha4 integrins |
| US20070208166A1 (en) | 2003-10-24 | 2007-09-06 | Exelixis, Inc. | Tao Kinase Modulators And Method Of Use |
| RU2372344C2 (ru) * | 2004-05-05 | 2009-11-10 | Ф. Хоффманн-Ля Рош Аг | Арилсульфонилбензодиоксаны, применяемые для модуляции 5-нт6 рецептора, 5-нт2a рецептора или и того, и другого |
| MXPA06013941A (es) | 2004-06-08 | 2007-12-10 | Neurosearch Sweden Ab | Fenilpiperidinas disustituidas, novedosas, como moduladores de la neurotransmision de dopamina y serotonina. |
| 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 |
| GT200600159A (es) | 2005-04-22 | 2007-03-14 | Derivados benzodioxano y benzodioxolano y usos de los mismos | |
| SE529246C2 (sv) | 2005-10-13 | 2007-06-12 | Neurosearch Sweden Ab | Nya disubstituerade fenyl-piperidiner som modulatorer för dopaminneurotransmission |
| US8492431B2 (en) | 2005-12-19 | 2013-07-23 | Janssen Pharmaceutica, N.V. | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of obesity |
| US8716231B2 (en) | 2005-12-19 | 2014-05-06 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of pain |
| US20070155824A1 (en) | 2005-12-19 | 2007-07-05 | Smith-Swintosky Virginia L | Use of benzo-fused heterocycle sulfamide derivatives for disease modification / epileptogenesis |
| US20070155823A1 (en) | 2005-12-19 | 2007-07-05 | Smith-Swintosky Virginia L | Use of benzo-fused heterocycle sulfamide derivatives as neuroprotective agents |
| 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 |
| 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 |
| US20070155827A1 (en) | 2005-12-19 | 2007-07-05 | Smith-Swintosky Virginia L | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of depression |
| 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. |
| AU2007253814A1 (en) | 2006-05-19 | 2007-11-29 | Janssen Pharmaceutica N.V. | Co-therapy for the treatment of epilepsy |
| 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 |
| JP2011519839A (ja) | 2008-04-29 | 2011-07-14 | エヌエスエイビー、フィリアル アヴ ノイロサーチ スウェーデン エービー、スヴェーリエ | ドーパミン神経伝達のモジュレーター |
| WO2009133110A1 (en) | 2008-04-29 | 2009-11-05 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Modulators of dopamine neurotransmission |
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2009
- 2009-04-28 MX MX2010011724A patent/MX2010011724A/es unknown
- 2009-04-28 KR KR1020107026636A patent/KR20100135325A/ko not_active Withdrawn
- 2009-04-28 US US12/990,048 patent/US8524766B2/en not_active Expired - Fee Related
- 2009-04-28 AU AU2009242092A patent/AU2009242092A1/en not_active Abandoned
- 2009-04-28 BR BRPI0911772A patent/BRPI0911772A2/pt not_active IP Right Cessation
- 2009-04-28 JP JP2011506689A patent/JP5514804B2/ja not_active Expired - Fee Related
- 2009-04-28 NZ NZ588209A patent/NZ588209A/xx not_active IP Right Cessation
- 2009-04-28 DK DK09738151.1T patent/DK2271634T3/da active
- 2009-04-28 RU RU2010141964/04A patent/RU2010141964A/ru not_active Application Discontinuation
- 2009-04-28 EP EP09738151.1A patent/EP2271634B1/en not_active Not-in-force
- 2009-04-28 CA CA2722978A patent/CA2722978A1/en not_active Abandoned
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- 2009-04-28 CN CN200980115417XA patent/CN102036976B/zh not_active Expired - Fee Related
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2010
- 2010-09-21 IL IL208289A patent/IL208289A0/en unknown
- 2010-09-29 ZA ZA2010/06932A patent/ZA201006932B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL208289A0 (en) | 2010-12-30 |
| BRPI0911772A2 (pt) | 2017-06-27 |
| JP5514804B2 (ja) | 2014-06-04 |
| CN102036976A (zh) | 2011-04-27 |
| EP2271634A1 (en) | 2011-01-12 |
| AU2009242092A1 (en) | 2009-11-05 |
| CA2722978A1 (en) | 2009-11-05 |
| CN102036976B (zh) | 2013-05-01 |
| WO2009133107A1 (en) | 2009-11-05 |
| ZA201006932B (en) | 2011-12-28 |
| NZ588209A (en) | 2012-08-31 |
| US20110105461A1 (en) | 2011-05-05 |
| DK2271634T3 (da) | 2014-05-05 |
| JP2011518858A (ja) | 2011-06-30 |
| US8524766B2 (en) | 2013-09-03 |
| KR20100135325A (ko) | 2010-12-24 |
| EP2271634B1 (en) | 2014-02-12 |
| MX2010011724A (es) | 2010-11-30 |
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