EA007543B1 - Производные 4-(3-трифторметилпиридин-5-ил)пиперазина, фармацевтическая композиция, способы их получения и применение - Google Patents
Производные 4-(3-трифторметилпиридин-5-ил)пиперазина, фармацевтическая композиция, способы их получения и применение Download PDFInfo
- Publication number
- EA007543B1 EA007543B1 EA200401526A EA200401526A EA007543B1 EA 007543 B1 EA007543 B1 EA 007543B1 EA 200401526 A EA200401526 A EA 200401526A EA 200401526 A EA200401526 A EA 200401526A EA 007543 B1 EA007543 B1 EA 007543B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- trifluoromethylpyridin
- acetate
- piperazine
- alkyl
- aryl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 44
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
- 150000004885 piperazines Chemical class 0.000 title claims description 6
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 2
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- 102000005962 receptors Human genes 0.000 claims description 40
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 9
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- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 5
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- MOJSBOKWCUWDIH-UHFFFAOYSA-N acetic acid;1-[6-ethylsulfanyl-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.C1=C(C(F)(F)F)C(SCC)=NC(N2CCNCC2)=C1 MOJSBOKWCUWDIH-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 2
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- PCJAICHMDCZKCD-UHFFFAOYSA-N acetic acid;1-[6-(2-cyclohexylethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCCC1CCCCC1 PCJAICHMDCZKCD-UHFFFAOYSA-N 0.000 claims description 2
- UCUYFHDVFOXRNQ-UHFFFAOYSA-N acetic acid;1-[6-(2-cyclopentylethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCCC1CCCC1 UCUYFHDVFOXRNQ-UHFFFAOYSA-N 0.000 claims description 2
- ZFAHGSNVXMFRGG-UHFFFAOYSA-N acetic acid;1-[6-(thiophen-3-ylmethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCC=1C=CSC=1 ZFAHGSNVXMFRGG-UHFFFAOYSA-N 0.000 claims description 2
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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| US20030236259A1 (en) * | 2002-02-05 | 2003-12-25 | Rolf Hohlweg | Novel aryl- and heteroarylpiperazines |
| JP5173190B2 (ja) * | 2004-08-25 | 2013-03-27 | 武田薬品工業株式会社 | 腹圧性尿失禁の予防・治療剤及びそのスクリーニング方法 |
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| CN103110635A (zh) * | 2005-07-04 | 2013-05-22 | 海波因特制药有限责任公司 | 组胺h3受体拮抗剂 |
| AR054849A1 (es) * | 2005-07-26 | 2007-07-18 | Wyeth Corp | Diazepinoquinolinas, sintesis de las mismas, e intermediarios para obtenerlas |
| JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
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| EP1998781A2 (en) * | 2006-03-24 | 2008-12-10 | Wyeth a Corporation of the State of Delaware | Treatment of pain |
| JP2009531435A (ja) * | 2006-03-24 | 2009-09-03 | ワイス | うつ病の治療用の新規な治療組み合わせ |
| JP5528699B2 (ja) | 2006-05-16 | 2014-06-25 | 武田薬品工業株式会社 | 縮合複素環化合物およびその用途 |
| ATE538116T1 (de) * | 2006-05-29 | 2012-01-15 | High Point Pharmaceuticals Llc | 3-(1,3-benyodioxol-5-yl)-6- (4- cyclopropylpiperazin-1-yl)-pyridazin, dessen salze und solvate und dessen verwendung als histamin-h3-rezeptorantagonist |
| WO2007149728A2 (en) * | 2006-06-20 | 2007-12-27 | Alcon Research, Ltd. | Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma |
| TW200823187A (en) * | 2006-10-24 | 2008-06-01 | Wyeth Corp | Benzodioxane derivatives and uses thereof |
| JO2642B1 (en) | 2006-12-08 | 2012-06-17 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
| JO2849B1 (en) | 2007-02-13 | 2015-03-15 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
| RU2489431C2 (ru) | 2007-04-23 | 2013-08-10 | Янссен Фармацевтика Н.В. | Тиа(диа)золы как быстро диссоциирующие антагонисты рецептора допамина 2 |
| JP5431305B2 (ja) | 2007-04-23 | 2014-03-05 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 高速解離性ドパミン２受容体アンタゴニストとしての４−アルコキシピリダジン誘導体 |
| EP2014656A3 (en) * | 2007-06-11 | 2011-08-24 | High Point Pharmaceuticals, LLC | New heteocyclic h3 antagonists |
| CL2008002777A1 (es) * | 2007-09-21 | 2010-01-22 | Wyeth Corp | Metodo de preparacion de compuestos diazepinoquinolinicos quirales por recristalizacion en un sistema de solvente ternario. |
| JP5520051B2 (ja) | 2007-11-15 | 2014-06-11 | 武田薬品工業株式会社 | 縮合ピリジン誘導体およびその用途 |
| JP5417439B2 (ja) | 2008-07-03 | 2014-02-12 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ５−ｈｔ６受容体アンタゴニストとしての置換された６−（１−ピペラジニル）−ピリダジン類 |
| EA019048B1 (ru) * | 2008-07-31 | 2013-12-30 | Янссен Фармацевтика Нв | Пиперазин-1-илтрифторметилзамещенные пиридины в качестве быстро диссоциирующихся антагонистов d-рецепторов дофамина |
| TWI542592B (zh) | 2009-06-15 | 2016-07-21 | 武田藥品工業股份有限公司 | 吡並氮雜氧雜環庚烯衍生物 |
| WO2011071136A1 (ja) | 2009-12-11 | 2011-06-16 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| US20130267500A1 (en) | 2010-09-01 | 2013-10-10 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level |
| WO2013010679A1 (en) | 2011-07-15 | 2013-01-24 | Novartis Ag | Salts of aza-bicyclic di-aryl ethers and methods to make them or their precursors |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| WO2019131902A1 (ja) | 2017-12-27 | 2019-07-04 | 武田薬品工業株式会社 | 腹圧性尿失禁および便失禁の治療薬 |
| CN121866253A (zh) * | 2023-07-04 | 2026-04-14 | 杭州中美华东制药有限公司 | 一种glp1r激动剂及其中间体的制备方法 |
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| US4078063A (en) * | 1976-09-24 | 1978-03-07 | Merck & Co., Inc. | Piperazinylpyridines |
| EP0370560A1 (en) * | 1988-11-24 | 1990-05-30 | Akzo Nobel N.V. | Pharmaceutical composition containing 1-[mono- or bis (trifluoromethyl)-2-pyridinyl] piperazines |
| EP0580465A1 (fr) * | 1992-06-25 | 1994-01-26 | Sanofi | Nouvelle utilisation thérapeutique d'hétérocyclyl-pipérazines comme 5-HT3 agonistes et nouveaux dérivés |
| WO1994003430A1 (en) * | 1992-07-31 | 1994-02-17 | Kabi Pharmacia Ab | Novel pyridyl- and pyrimidylpiperazine derivatives |
| WO1998033504A1 (en) * | 1997-02-03 | 1998-08-06 | Akzo Nobel N.V. | Treatment of urinary incontinence |
| WO2001041701A2 (en) * | 1999-12-06 | 2001-06-14 | H. Lundbeck A/S | The combination of a serotonin reuptake inhibitor and a 5-ht2c antagonist, inverse agonist or partial agonist |
| EP1213017A2 (en) * | 2000-12-05 | 2002-06-12 | Akzo Nobel N.V. | Use of a 5-HT2C receptor agonist for the treatment of hot flushes |
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| JPH0665203A (ja) * | 1992-06-25 | 1994-03-08 | Elf Sanofi | ピペラジンのヘテロ環誘導体 |
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| JP3989102B2 (ja) * | 1997-10-02 | 2007-10-10 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 縮合ピリジン誘導体 |
| AU2426602A (en) * | 2000-11-20 | 2002-05-27 | Biovitrum Ab | Piperazinylpyrazine compounds as agonist or antagonist of serotonin 5ht-2 receptor |
| US6498184B2 (en) * | 2000-12-05 | 2002-12-24 | Akzo Nobel N.V. | Serotonergic compound for a method of treatment of hot flushes in post-menopausal women |
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| US4078063A (en) * | 1976-09-24 | 1978-03-07 | Merck & Co., Inc. | Piperazinylpyridines |
| EP0370560A1 (en) * | 1988-11-24 | 1990-05-30 | Akzo Nobel N.V. | Pharmaceutical composition containing 1-[mono- or bis (trifluoromethyl)-2-pyridinyl] piperazines |
| EP0580465A1 (fr) * | 1992-06-25 | 1994-01-26 | Sanofi | Nouvelle utilisation thérapeutique d'hétérocyclyl-pipérazines comme 5-HT3 agonistes et nouveaux dérivés |
| WO1994003430A1 (en) * | 1992-07-31 | 1994-02-17 | Kabi Pharmacia Ab | Novel pyridyl- and pyrimidylpiperazine derivatives |
| WO1998033504A1 (en) * | 1997-02-03 | 1998-08-06 | Akzo Nobel N.V. | Treatment of urinary incontinence |
| WO2001041701A2 (en) * | 1999-12-06 | 2001-06-14 | H. Lundbeck A/S | The combination of a serotonin reuptake inhibitor and a 5-ht2c antagonist, inverse agonist or partial agonist |
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| KR20050026702A (ko) | 2005-03-15 |
| NZ536409A (en) | 2007-11-30 |
| BR0310077A (pt) | 2005-02-22 |
| RS99804A (sr) | 2006-12-15 |
| AU2003228196B2 (en) | 2009-12-17 |
| IL164974A0 (en) | 2005-12-18 |
| AU2003228196A1 (en) | 2003-12-02 |
| US7229997B2 (en) | 2007-06-12 |
| DE60305484D1 (de) | 2006-06-29 |
| HK1084941A1 (en) | 2006-08-11 |
| CA2483619A1 (en) | 2003-11-27 |
| WO2003097636A1 (en) | 2003-11-27 |
| EP1506185B1 (en) | 2006-05-24 |
| CY1105162T1 (el) | 2010-03-03 |
| US20030232814A1 (en) | 2003-12-18 |
| DK1506185T3 (da) | 2006-10-02 |
| SE0201544D0 (sv) | 2002-05-17 |
| EA200401526A1 (ru) | 2005-04-28 |
| ES2263971T3 (es) | 2006-12-16 |
| SI1506185T1 (sl) | 2006-10-31 |
| ATE327229T1 (de) | 2006-06-15 |
| DE60305484T2 (de) | 2006-11-09 |
| CN1701068A (zh) | 2005-11-23 |
| CN1329389C (zh) | 2007-08-01 |
| JP2005529926A (ja) | 2005-10-06 |
| PT1506185E (pt) | 2006-10-31 |
| EP1506185A1 (en) | 2005-02-16 |
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