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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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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| EP2248524A3 (en) | 2004-08-25 | 2011-03-09 | Takeda Pharmaceutical Company Limited | Preventives/remedies for stress urinary incontinence and method of screening the same |
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| RU2499795C2 (ru) | 2005-07-04 | 2013-11-27 | Хай Пойнт Фармасьютикалс, ЛЛС | Антагонисты гистаминовых н3-рецепторов |
| 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 |
| TW200734334A (en) * | 2006-01-13 | 2007-09-16 | Wyeth Corp | Treatment of substance abuse |
| KR20080110759A (ko) * | 2006-03-24 | 2008-12-19 | 와이어쓰 | 통증 치료 |
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| EP2742936A1 (en) | 2006-05-16 | 2014-06-18 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound and use thereof |
| SG163547A1 (en) * | 2006-05-29 | 2010-08-30 | High Point Pharmaceuticals Llc | 3- (1, 3-benz0di0x0l-5-yl) -6- (4-cyclopropylpiperazin-1-yl) -pyridazine, its salts and solvates and its use as histamine h3 receptor antagonist |
| US20070293475A1 (en) * | 2006-06-20 | 2007-12-20 | Alcon Manufacturing 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 |
| KR20100016620A (ko) | 2007-04-23 | 2010-02-12 | 얀센 파마슈티카 엔.브이. | 속해리성 도파민 2 수용체 길항제로서의 4-알콕시피리다진 유도체 |
| AU2008240729B2 (en) | 2007-04-23 | 2012-08-23 | Janssen Pharmaceutica N.V. | Thia(dia)zoles as fast dissociating dopamine 2 receptor antagonists |
| 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. |
| EP2789338A3 (en) | 2007-11-15 | 2015-01-14 | Takeda Pharmaceutical Company Limited | Condensed pyridine derivate and use thereof |
| RU2502734C2 (ru) | 2008-07-03 | 2013-12-27 | Янссен Фармацевтика Нв | Замещенные 6-(1-пиперазинил)-пиридазины в качестве антагонистов 5-нт6 рецептора |
| CA2730774C (en) | 2008-07-31 | 2016-09-13 | Janssen Pharmaceutica Nv | Piperazin-1-yl-trifluoromethyl-substituted-pyridines as fast dissociating dopamine 2 receptor antagonists |
| MX2011013081A (es) | 2009-06-15 | 2012-01-20 | Takeda Pharmaceutical | Derivados de pirazinooxazepina. |
| JPWO2011071136A1 (ja) | 2009-12-11 | 2013-04-22 | 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 |
| TWI589576B (zh) | 2011-07-15 | 2017-07-01 | 諾華公司 | 氮雜－雙環二芳基醚之鹽類及製造彼等或其前驅物之方法 |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| EP3733204A4 (en) | 2017-12-27 | 2021-09-15 | Takeda Pharmaceutical Company Limited | THERAPEUTIC AGENT FOR URINARY INCONTINENCE OF STRESS AND FECAL INCONTINENCE |
| TW202504600A (zh) * | 2023-07-04 | 2025-02-01 | 大陸商杭州中美華東製藥有限公司 | Glp1r激動劑及其中間體的製備方法 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0665203A (ja) * | 1992-06-25 | 1994-03-08 | Elf Sanofi | ピペラジンのヘテロ環誘導体 |
| JPH0797370A (ja) * | 1993-09-29 | 1995-04-11 | Asahi Chem Ind Co Ltd | ２−アルコキシピラジン誘導体およびその用途 |
| 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 |
| BR0115400A (pt) * | 2000-11-20 | 2003-09-30 | Biovitrum Ab | Compostos de piperazinilpirazina atuando como agonistas ou antagonistas do receptor 5ht-2 de serotonina |
| 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 |
| 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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| British Journal of Pharmacology, Vol. 128, 1999, R.H.P. Porter et al.: "Functional characterization of agonists at recombinant human 5-HT2A, 5-HT2B and 5-HT2C receptors in CH0-K1 cells", page 13-page 20, see part, abstract, page 14, page 16, table 1, page 17, figure 3E * |
| European Neuropsychopharmacology, Vol. 8, Issue 3, August 1998, Francois Jenck et al.: "Antiversive effects of 5HT2C receptor agonists and fluoxetine in a model of panic-like anxiety in rats", page 161-page 168, retrieved on 2002-11-13 http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6T26-3T2PCKB-1& * |
Also Published As
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| SE0201544D0 (sv) | 2002-05-17 |
| US7229997B2 (en) | 2007-06-12 |
| ES2263971T3 (es) | 2006-12-16 |
| RS99804A (sr) | 2006-12-15 |
| KR20050026702A (ko) | 2005-03-15 |
| CY1105162T1 (el) | 2010-03-03 |
| WO2003097636A1 (en) | 2003-11-27 |
| EA200401526A1 (ru) | 2005-04-28 |
| NO20045486L (no) | 2005-02-02 |
| AU2003228196A1 (en) | 2003-12-02 |
| DE60305484T2 (de) | 2006-11-09 |
| CN1701068A (zh) | 2005-11-23 |
| IL164974A0 (en) | 2005-12-18 |
| DE60305484D1 (de) | 2006-06-29 |
| JP2005529926A (ja) | 2005-10-06 |
| CN1329389C (zh) | 2007-08-01 |
| CA2483619A1 (en) | 2003-11-27 |
| ATE327229T1 (de) | 2006-06-15 |
| US20030232814A1 (en) | 2003-12-18 |
| AU2003228196B2 (en) | 2009-12-17 |
| PT1506185E (pt) | 2006-10-31 |
| DK1506185T3 (da) | 2006-10-02 |
| HK1084941A1 (en) | 2006-08-11 |
| SI1506185T1 (sl) | 2006-10-31 |
| ZA200408975B (en) | 2005-11-14 |
| JP4865221B2 (ja) | 2012-02-01 |
| EP1506185A1 (en) | 2005-02-16 |
| BR0310077A (pt) | 2005-02-22 |
| EP1506185B1 (en) | 2006-05-24 |
| MXPA04011437A (es) | 2005-02-17 |
| NZ536409A (en) | 2007-11-30 |
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