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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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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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)
- Bioinformatics & Cheminformatics (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 |
Publications (3)
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| JP2011518859A JP2011518859A (ja) | 2011-06-30 |
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| EP (1) | EP2271638B1 (enExample) |
| JP (1) | JP5548853B2 (enExample) |
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| DK (1) | DK2271638T3 (enExample) |
| MX (1) | MX2010011498A (enExample) |
| WO (1) | WO2009133110A1 (enExample) |
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| DK2271634T3 (da) | 2008-04-29 | 2014-05-05 | Integrative Res Lab Sweden Ab | Modulatorer af dopamin-neurotransmission |
| EP2271635A1 (en) * | 2008-04-29 | 2011-01-12 | NSAB, Filial af NeuroSearch Sweden AB, Sverige | Modulators of dopamine neurotransmission |
| JP5876140B2 (ja) | 2011-04-19 | 2016-03-02 | インテグレイティブ・リサーチ・ラボラトリーズ・スウェーデン・アーベー | 皮質のドーパミン作動性及びｎｍｄａ受容体介在のグルタミン酸作動性神経伝達の新規なモジュレータ |
| CN105979942B (zh) * | 2013-12-12 | 2018-12-07 | 比皮艾思药物研发有限公司 | 用于治疗或缓解疼痛的氨基磺酸酯衍生物 |
| 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 |
| WO2020239568A1 (en) | 2019-05-24 | 2020-12-03 | Integrative Research Laboratories Sweden Ab | Pharmaceutically acceptable salts of [2-(3-fluoro-5-methane-sulfonylphenoxy)ethyl](propyl)amine and uses thereof |
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| US3058980A (en) * | 1962-10-16 | Substitution products of benzo- | ||
| US2906757A (en) * | 1959-09-29 | Their preparation | ||
| 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 |
| 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 |
| 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 |
| JP2005505586A (ja) | 2001-10-04 | 2005-02-24 | ワイス | ５−ヒドロキシトリプタミン−６リガンドとしてのクロマン誘導体 |
| US20070208166A1 (en) * | 2003-10-24 | 2007-09-06 | Exelixis, Inc. | Tao Kinase Modulators And Method Of Use |
| NZ550441A (en) | 2004-05-05 | 2009-07-31 | Hoffmann La Roche | Arylsulfonyl benzodioxanes useful for modulating the 5-HT6 receptor, the 5-HT2A receptor or both |
| KR101245075B1 (ko) * | 2004-06-08 | 2013-03-18 | 엔에스아베 필리알 아프 뉴로서치 스웨덴 아베 스베리게 | 도파민 신경전달의 모듈레이터로서 신 2기치환된페닐피페리딘/피페라진 |
| 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 |
| TW200612905A (en) * | 2004-06-16 | 2006-05-01 | 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 |
| BRPI0610046A2 (pt) * | 2005-04-22 | 2010-05-25 | Wyeth Corp | derivados de benzodioxano e benzodioxolano e usos destes |
| 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 |
| 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 |
| AR058389A1 (es) * | 2005-12-19 | 2008-01-30 | Janssen Pharmaceutica Nv | Uso de derivados heterociclicos benzo-fusionados de sulfamida para el tratamiento de la obesidad |
| US20070155823A1 (en) * | 2005-12-19 | 2007-07-05 | Smith-Swintosky Virginia L | Use of benzo-fused heterocycle sulfamide derivatives as neuroprotective agents |
| 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. |
| 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 |
| DK2271634T3 (da) * | 2008-04-29 | 2014-05-05 | Integrative Res Lab Sweden Ab | Modulatorer af dopamin-neurotransmission |
| EP2271635A1 (en) | 2008-04-29 | 2011-01-12 | NSAB, Filial af NeuroSearch Sweden AB, Sverige | Modulators of dopamine neurotransmission |
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| MX2010011498A (es) | 2010-11-12 |
| CA2722986A1 (en) | 2009-11-05 |
| US20110112065A1 (en) | 2011-05-12 |
| AU2009242095A1 (en) | 2009-11-05 |
| EP2271638A1 (en) | 2011-01-12 |
| JP2011518859A (ja) | 2011-06-30 |
| DK2271638T3 (da) | 2011-11-28 |
| CN102015674B (zh) | 2014-10-29 |
| WO2009133110A1 (en) | 2009-11-05 |
| ATE522515T1 (de) | 2011-09-15 |
| EP2271638B1 (en) | 2011-08-31 |
| US8492372B2 (en) | 2013-07-23 |
| CN102015674A (zh) | 2011-04-13 |
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