JP5548853B2 - ドーパミン神経伝達のモジュレーター - Google Patents
ドーパミン神経伝達のモジュレーター Download PDFInfo
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- JP5548853B2 JP5548853B2 JP2011506691A JP2011506691A JP5548853B2 JP 5548853 B2 JP5548853 B2 JP 5548853B2 JP 2011506691 A JP2011506691 A JP 2011506691A JP 2011506691 A JP2011506691 A JP 2011506691A JP 5548853 B2 JP5548853 B2 JP 5548853B2
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- JP
- Japan
- Prior art keywords
- benzodioxin
- methyl
- methylsulfonyl
- amine
- 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.)
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- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title abstract description 43
- 229960003638 dopamine Drugs 0.000 title abstract description 21
- 230000005062 synaptic transmission Effects 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 168
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims description 74
- 150000003839 salts Chemical class 0.000 claims description 46
- -1 3,3,3-trifluoropropyl Chemical group 0.000 claims description 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 25
- 150000001204 N-oxides Chemical class 0.000 claims description 24
- 208000035475 disorder Diseases 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- YKSJLFIAVRHURG-UHFFFAOYSA-N n-[(7-methylsulfonyl-4h-1,3-benzodioxin-2-yl)methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCCC)OCC2=C1 YKSJLFIAVRHURG-UHFFFAOYSA-N 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 8
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- PUQAQSKSJYGJLE-UHFFFAOYSA-N n-[(7-methylsulfonyl-4h-1,3-benzodioxin-2-yl)methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCC)OCC2=C1 PUQAQSKSJYGJLE-UHFFFAOYSA-N 0.000 claims description 7
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 5
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- WBGIYAFUOWMNNS-UHFFFAOYSA-N 1-(5-fluoro-7-methylsulfonyl-4h-1,3-benzodioxin-2-yl)-n-methylmethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNC)OCC2=C1F WBGIYAFUOWMNNS-UHFFFAOYSA-N 0.000 claims description 3
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- DIMPADLYPKZKIX-UHFFFAOYSA-N 1-[(5-fluoro-7-methylsulfonyl-4h-1,3-benzodioxin-2-yl)methyl]pyrrolidine Chemical compound O1C2=CC(S(=O)(=O)C)=CC(F)=C2COC1CN1CCCC1 DIMPADLYPKZKIX-UHFFFAOYSA-N 0.000 claims description 3
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- BQOYOAIMHRKLCO-UHFFFAOYSA-N 1-[[7-(trifluoromethylsulfonyl)-4h-1,3-benzodioxin-2-yl]methyl]pyrrolidine Chemical compound O1C2=CC(S(=O)(=O)C(F)(F)F)=CC=C2COC1CN1CCCC1 BQOYOAIMHRKLCO-UHFFFAOYSA-N 0.000 claims description 3
- IOOMSAXDDYUHMI-UHFFFAOYSA-N 2-[(7-methylsulfonyl-4h-1,3-benzodioxin-2-yl)methylamino]ethanol Chemical compound C1OC(CNCCO)OC2=CC(S(=O)(=O)C)=CC=C21 IOOMSAXDDYUHMI-UHFFFAOYSA-N 0.000 claims description 3
- SIZURZPTODVUEQ-UHFFFAOYSA-N 2-methoxy-n-[(7-methylsulfonyl-4h-1,3-benzodioxin-2-yl)methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCCOC)OCC2=C1 SIZURZPTODVUEQ-UHFFFAOYSA-N 0.000 claims description 3
- IDDXYZCGXDKVKF-UHFFFAOYSA-N 4-[(7-methylsulfonyl-4h-1,3-benzodioxin-2-yl)methyl]morpholine Chemical compound O1C2=CC(S(=O)(=O)C)=CC=C2COC1CN1CCOCC1 IDDXYZCGXDKVKF-UHFFFAOYSA-N 0.000 claims description 3
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- VKRNPXCFNACOML-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-4h-1,3-benzodioxin-2-yl)methyl]-2,2-dimethylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCC(C)(C)C)OCC2=C1F VKRNPXCFNACOML-UHFFFAOYSA-N 0.000 claims description 3
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- AMMWXFDIXMLYFS-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-4h-1,3-benzodioxin-2-yl)methyl]-2-methylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCC(C)C)OCC2=C1F AMMWXFDIXMLYFS-UHFFFAOYSA-N 0.000 claims description 3
- ZKLBOHJDJLAYBE-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-4h-1,3-benzodioxin-2-yl)methyl]-n-methylethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(C)CC)OCC2=C1F ZKLBOHJDJLAYBE-UHFFFAOYSA-N 0.000 claims description 3
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- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
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- A61P3/04—Anorexiants; Antiobesity agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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- Hospice & Palliative Care (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Steroid Compounds (AREA)
- Liquid Crystal Substances (AREA)
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| US61/049,057 | 2008-04-30 | ||
| PCT/EP2009/055140 WO2009133110A1 (en) | 2008-04-29 | 2009-04-28 | Modulators of dopamine neurotransmission |
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| MX2010011724A (es) | 2008-04-29 | 2010-11-30 | Nsab Af Neurosearch Sweden Ab | Moduladores de neurotransmision de dopamina. |
| 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 |
| US9006227B2 (en) | 2011-04-19 | 2015-04-14 | Integrative Research Laboratories Sweden Ab | Modulators of cortical dopaminergic- and NMDA-receptor-mediated glutamatergic neurotransmission |
| US10081615B2 (en) * | 2013-12-12 | 2018-09-25 | Bio-Pharm Solutions Co., Ltd. | Sulfamate derivative compounds for use in treating or alleviating pain |
| CN106928147A (zh) * | 2017-03-14 | 2017-07-07 | 华东师范大学 | 三环二萜类似物及其制备方法、及其在制备抗前列腺癌药物中的应用 |
| 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 |
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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 |
| US3851062A (en) | 1973-08-01 | 1974-11-26 | Minnesota Mining & Mfg | Method of suppressing weight gain |
| US4056540A (en) * | 1974-01-01 | 1977-11-01 | Bristol-Myers Company | 4-Phenyl-1,3-benzodioxans |
| US5189171A (en) | 1991-06-21 | 1993-02-23 | American Home Products Corporation | Antipsychotic benzodioxan derivatives |
| 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 |
| 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 |
| WO1996038435A1 (en) * | 1995-05-30 | 1996-12-05 | Abbott Laboratories | Dopamine agonists |
| 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 |
| 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 |
| 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 |
| US20070155823A1 (en) | 2005-12-19 | 2007-07-05 | Smith-Swintosky Virginia L | Use of benzo-fused heterocycle sulfamide derivatives as neuroprotective agents |
| US20070155824A1 (en) | 2005-12-19 | 2007-07-05 | Smith-Swintosky Virginia L | Use of benzo-fused heterocycle sulfamide derivatives for disease modification / epileptogenesis |
| 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 |
| MX2010011724A (es) | 2008-04-29 | 2010-11-30 | Nsab Af Neurosearch Sweden Ab | Moduladores de neurotransmision de dopamina. |
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Also Published As
| Publication number | Publication date |
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| MX2010011498A (es) | 2010-11-12 |
| CN102015674B (zh) | 2014-10-29 |
| WO2009133110A1 (en) | 2009-11-05 |
| AU2009242095A1 (en) | 2009-11-05 |
| DK2271638T3 (da) | 2011-11-28 |
| CN102015674A (zh) | 2011-04-13 |
| EP2271638B1 (en) | 2011-08-31 |
| US20110112065A1 (en) | 2011-05-12 |
| US8492372B2 (en) | 2013-07-23 |
| CA2722986A1 (en) | 2009-11-05 |
| ATE522515T1 (de) | 2011-09-15 |
| EP2271638A1 (en) | 2011-01-12 |
| JP2011518859A (ja) | 2011-06-30 |
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