ES2154605A1 - Nuevos derivados mixtos de bencimidazol-arilpiperazina con afinidad por los receptores serotoninergicos 5-ht1a y 5-ht3 - Google Patents
Nuevos derivados mixtos de bencimidazol-arilpiperazina con afinidad por los receptores serotoninergicos 5-ht1a y 5-ht3Info
- Publication number
- ES2154605A1 ES2154605A1 ES009902042A ES9902042A ES2154605A1 ES 2154605 A1 ES2154605 A1 ES 2154605A1 ES 009902042 A ES009902042 A ES 009902042A ES 9902042 A ES9902042 A ES 9902042A ES 2154605 A1 ES2154605 A1 ES 2154605A1
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- ES
- Spain
- Prior art keywords
- sup
- alkyl
- sub
- hydrogen
- arilpiperazina
- 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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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Nuevos derivados mixtos de bencimidazol-arilpiperazina con afinidad por los receptores serotoninérgicos 5-HT{sub, 1A} y 5- HT{sub, 3}. La presente invención trata de nuevos compuestos de fórmula general I donde X es un grupo amido, tioamido, éster, cetona, hidroximetilo; R{sup, 1} es hidrógeno, halógeno, alquilo, alcoxi; R{sup, 2} es hidrógeno, nitro, amino; R{sup, 3} es hidrógeno, alquilo; R{sup, 4} es alquilo, arilo, heteroarilo; n es igual a 1-4; y la subunidad azabicíclica es azabiciclo [x.y.z] alquilo. Se describen los métodos de preparación de dichos compuestos, los cuales presentan afinidad por los receptores serotoninérgicos 5-HT{sub, 1A} y 5-HT{sub, 3} lo que indica su interés desde el punto de vista terapéutico para el tratamiento de trastornos del sistema nervioso central (SNC).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES9902042A ES2154605B1 (es) | 1999-09-14 | 1999-09-14 | Nuevos derivados mixtos de bencimidazol-arilpiperazina con afinidad por los receptores serotoninergicos 5-ht1a y 5-ht3 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES9902042A ES2154605B1 (es) | 1999-09-14 | 1999-09-14 | Nuevos derivados mixtos de bencimidazol-arilpiperazina con afinidad por los receptores serotoninergicos 5-ht1a y 5-ht3 |
Publications (2)
Publication Number | Publication Date |
---|---|
ES2154605A1 true ES2154605A1 (es) | 2001-04-01 |
ES2154605B1 ES2154605B1 (es) | 2001-11-16 |
Family
ID=8309929
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES9902042A Expired - Fee Related ES2154605B1 (es) | 1999-09-14 | 1999-09-14 | Nuevos derivados mixtos de bencimidazol-arilpiperazina con afinidad por los receptores serotoninergicos 5-ht1a y 5-ht3 |
Country Status (1)
Country | Link |
---|---|
ES (1) | ES2154605B1 (es) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002088093A1 (en) * | 2001-03-09 | 2002-11-07 | Abbott Laboratories | Benzimidazoles that are useful in treating sexual dysfunction |
WO2003076431A1 (en) * | 2002-03-08 | 2003-09-18 | Abbott Laboratories | Benzimidazole-derivatives for the treatment of sexual dysfunction |
US7256294B2 (en) | 2005-05-25 | 2007-08-14 | Theravance, Inc. | Crystalline form of a benzimidazole-carboxamide medicinal compound |
WO2007144005A1 (en) | 2006-06-16 | 2007-12-21 | H. Lundbeck A/S | 1- [2- (2, 4-dimethylphenylsulfanyl) -phenyl] piperazine as a compound with combined serotonin reuptake, 5-ht3 and 5-ht1a activity for the treatment of cognitive impairment |
US7351704B2 (en) | 2004-02-18 | 2008-04-01 | Theravance, Inc. | Indazole-carboxamide compounds as 5-HT4 receptor agonists |
US7351732B2 (en) | 2002-07-31 | 2008-04-01 | Schwarz Pharma S.L. | Cycloalkanedione derivatives, method for the production thereof and their pharmacological applications |
US7351828B2 (en) | 2001-03-09 | 2008-04-01 | Abbott Laboratories | Benzimidazoles that are useful in treating sexual dysfunction |
US7375114B2 (en) | 2004-04-07 | 2008-05-20 | Theravance, Inc. | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
US7396933B2 (en) | 2004-11-05 | 2008-07-08 | Theravance, Inc. | Quinolinone-carboxamide compounds |
US7399862B2 (en) | 2004-11-05 | 2008-07-15 | Theravance, Inc. | 5-HT4 receptor agonist compounds |
US7419989B2 (en) | 2004-12-22 | 2008-09-02 | Theravance, Inc. | Indazole-carboxamide compounds |
US7446114B2 (en) | 2005-03-02 | 2008-11-04 | Theravance, Inc. | Quinolinone compounds as 5-HT4 receptor agonists |
US7728006B2 (en) | 2004-04-07 | 2010-06-01 | Theravance, Inc. | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
US7759363B2 (en) | 2005-05-25 | 2010-07-20 | Theravance, Inc. | Benzimidazole-carboxamide compounds as 5-HT4, receptor agonists |
US8309575B2 (en) | 2004-04-07 | 2012-11-13 | Theravance, Inc. | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
WO2020095912A1 (ja) * | 2018-11-06 | 2020-05-14 | 第一三共株式会社 | ベンズイミダゾール誘導体 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0628549A1 (en) * | 1993-05-21 | 1994-12-14 | Fabrica Espanola De Productos Quimicos Y Farmaceuticos, S.A. (Faes) | New 1-phenylmethyl benzimidazole piperazine derivatives |
WO1996006846A1 (es) * | 1994-09-01 | 1996-03-07 | Universidad Complutense De Madrid | Nuevos derivados de arilpiperazinas |
ES2094690A1 (es) * | 1994-11-22 | 1997-01-16 | Univ Madrid Complutense | Nuevos derivados de imida-piperazinas. |
WO1997035860A1 (es) * | 1996-03-22 | 1997-10-02 | Universidad Complutense De Madrid Rectorado | Nuevos derivados de bencimidazol con afinidad por los receptores serotoninergicos 5-ht3/5-ht¿4? |
WO1998024771A1 (en) * | 1996-12-02 | 1998-06-11 | Fujisawa Pharmaceutical Co., Ltd. | Benzamide derivatives having a vasopressin antagonistic activity |
-
1999
- 1999-09-14 ES ES9902042A patent/ES2154605B1/es not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0628549A1 (en) * | 1993-05-21 | 1994-12-14 | Fabrica Espanola De Productos Quimicos Y Farmaceuticos, S.A. (Faes) | New 1-phenylmethyl benzimidazole piperazine derivatives |
WO1996006846A1 (es) * | 1994-09-01 | 1996-03-07 | Universidad Complutense De Madrid | Nuevos derivados de arilpiperazinas |
ES2094690A1 (es) * | 1994-11-22 | 1997-01-16 | Univ Madrid Complutense | Nuevos derivados de imida-piperazinas. |
WO1997035860A1 (es) * | 1996-03-22 | 1997-10-02 | Universidad Complutense De Madrid Rectorado | Nuevos derivados de bencimidazol con afinidad por los receptores serotoninergicos 5-ht3/5-ht¿4? |
WO1998024771A1 (en) * | 1996-12-02 | 1998-06-11 | Fujisawa Pharmaceutical Co., Ltd. | Benzamide derivatives having a vasopressin antagonistic activity |
Cited By (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7351828B2 (en) | 2001-03-09 | 2008-04-01 | Abbott Laboratories | Benzimidazoles that are useful in treating sexual dysfunction |
US6960589B2 (en) | 2001-03-09 | 2005-11-01 | Abbott Laboratories | Benzimidazoles that are useful in treating sexual dysfunction |
WO2002088093A1 (en) * | 2001-03-09 | 2002-11-07 | Abbott Laboratories | Benzimidazoles that are useful in treating sexual dysfunction |
WO2003076431A1 (en) * | 2002-03-08 | 2003-09-18 | Abbott Laboratories | Benzimidazole-derivatives for the treatment of sexual dysfunction |
US7351732B2 (en) | 2002-07-31 | 2008-04-01 | Schwarz Pharma S.L. | Cycloalkanedione derivatives, method for the production thereof and their pharmacological applications |
US8044045B2 (en) | 2004-02-18 | 2011-10-25 | Theravance, Inc. | Indazole-carboxamide compounds as 5-HT4 receptor agonists |
US7351704B2 (en) | 2004-02-18 | 2008-04-01 | Theravance, Inc. | Indazole-carboxamide compounds as 5-HT4 receptor agonists |
US7375114B2 (en) | 2004-04-07 | 2008-05-20 | Theravance, Inc. | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
US9630960B2 (en) | 2004-04-07 | 2017-04-25 | Theravance Biopharma R&D Ip, Llc | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
US9353106B2 (en) | 2004-04-07 | 2016-05-31 | Theravance Biopharma R&D Ip, Llc | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
US8962653B2 (en) | 2004-04-07 | 2015-02-24 | Theravance Biopharma R&D Ip, Llc | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
US8309575B2 (en) | 2004-04-07 | 2012-11-13 | Theravance, Inc. | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
US7728006B2 (en) | 2004-04-07 | 2010-06-01 | Theravance, Inc. | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
US9873692B2 (en) | 2004-04-07 | 2018-01-23 | Theravance Biopharma R&D Ip, Llc | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
US7763637B2 (en) | 2004-04-07 | 2010-07-27 | Theravance, Inc. | Quinolinone-carboxamide compounds as 5-HT4, receptor agonists |
US7396933B2 (en) | 2004-11-05 | 2008-07-08 | Theravance, Inc. | Quinolinone-carboxamide compounds |
US7399862B2 (en) | 2004-11-05 | 2008-07-15 | Theravance, Inc. | 5-HT4 receptor agonist compounds |
US7498442B2 (en) | 2004-11-05 | 2009-03-03 | Theravance, Inc. | Quinolinone-carboxamide compounds |
US7534889B2 (en) | 2004-11-05 | 2009-05-19 | Theravance, Inc. | 5-HT4 receptor agonist compounds |
US8003664B2 (en) | 2004-12-22 | 2011-08-23 | Theravance, Inc. | Indazole-carboxamide compounds |
US7419989B2 (en) | 2004-12-22 | 2008-09-02 | Theravance, Inc. | Indazole-carboxamide compounds |
US7786136B2 (en) | 2004-12-22 | 2010-08-31 | Theravance, Inc. | Indazole-carboxamide compounds |
US7875629B2 (en) | 2005-03-02 | 2011-01-25 | Theravance, Inc. | Quinolinone compounds as 5-HT4 receptor agonists |
US7446114B2 (en) | 2005-03-02 | 2008-11-04 | Theravance, Inc. | Quinolinone compounds as 5-HT4 receptor agonists |
US7622587B2 (en) | 2005-05-25 | 2009-11-24 | Theravance, Inc. | Crystalline form of a benzimidazole-carboxamide medicinal compound |
US8143279B2 (en) | 2005-05-25 | 2012-03-27 | Theravance, Inc. | Benzimidazole-carboxamide compounds as 5-HT4 receptor agonists |
US10696656B2 (en) | 2005-05-25 | 2020-06-30 | Theravance Biopharma R&D Ip, Llc | Benzimidazole-carboxamide compounds as 5-HT4 receptor agonists |
US8288550B2 (en) | 2005-05-25 | 2012-10-16 | Theravance, Inc. | Crystalline form of a benzimidazole-carboxamide medicinal compound |
US7759363B2 (en) | 2005-05-25 | 2010-07-20 | Theravance, Inc. | Benzimidazole-carboxamide compounds as 5-HT4, receptor agonists |
US8377964B2 (en) | 2005-05-25 | 2013-02-19 | Theravance, Inc. | Benzimidazole-carboxamide compounds as 5-HT4 receptor agonists |
US10233172B2 (en) | 2005-05-25 | 2019-03-19 | Theravance Biopharma R&D Ip, Llc | Benzimidazole-carboxamide compounds as 5-HT4 receptor agonists |
US11254655B2 (en) | 2005-05-25 | 2022-02-22 | Theravance Biopharma R&D Ip, Llc | Benzimidazole-carboxamide compounds as 5-HT4 receptor agonists |
US9975877B2 (en) | 2005-05-25 | 2018-05-22 | Theravance Biopharma R&D Ip, Llc | Benzimidazole-carboxamide compounds as 5-HT4 receptor agonists |
US7256294B2 (en) | 2005-05-25 | 2007-08-14 | Theravance, Inc. | Crystalline form of a benzimidazole-carboxamide medicinal compound |
US7897775B2 (en) | 2005-05-25 | 2011-03-01 | Theravance, Inc. | Crystalline form of a benzimidazole-carboxamide medicinal compound |
US9428489B2 (en) | 2005-05-25 | 2016-08-30 | Theravance Biopharma R&D Ip, Llc | Benzimidazole-carboxamide compounds as 5-HT4 receptor agonists |
US9101626B2 (en) | 2006-06-16 | 2015-08-11 | H. Lundbeck A/S | Process for preparing 1-[2-(2,4-dimethylphenylsulfanyl)-phenyl]piperazine or pharmaceutically acceptable salt thereof |
US9095588B2 (en) | 2006-06-16 | 2015-08-04 | H. Lundbeck A/S | Process for preparing 1-[2-(2,4-dimethylphenysulfanyl)-pheny]piperazine or pharmaceutically acceptable salt thereof |
US9227946B2 (en) | 2006-06-16 | 2016-01-05 | H. Lundbeck A/S | 1-[2-(2,4 dimethylphenylsulfanyl)-phenyl]piperazine as a compound with combined serotonin reuptake, 5-HT3 and 5-HT1a activity for the treatment of cognitive impairment |
US9125910B2 (en) | 2006-06-16 | 2015-09-08 | H. Lundbeck A/S | 1-[2-(2,4 dimethylphenylsulfanyl)-phenyl]piperazine as a compound with combined serotonin reuptake, 5-HT3 and 5-HT1A activity for the treatment of cognitive impairment |
US9125908B2 (en) | 2006-06-16 | 2015-09-08 | H. Lundbeck A/S | 1-[2-(2,4-dimethylphenylsulfanyl)-phenyl]piperazine as a compound with combined serotonin reuptake, 5-HT3 and 5-HT1A activity for the treatment of cognitive impairment |
WO2007144005A1 (en) | 2006-06-16 | 2007-12-21 | H. Lundbeck A/S | 1- [2- (2, 4-dimethylphenylsulfanyl) -phenyl] piperazine as a compound with combined serotonin reuptake, 5-ht3 and 5-ht1a activity for the treatment of cognitive impairment |
US9861630B1 (en) | 2006-06-16 | 2018-01-09 | H. Lundbeck A/S | 1-[2-(2,4-dimethylphenylsulfanyl)-phenyl]piperazine as a compound with combined serotonin reuptake, 5-HT3 and 5-HT1A activity for the treatment of cognitive impairment |
US9125909B2 (en) | 2006-06-16 | 2015-09-08 | H. Lundbeck A/S | 1-[2-(2,4 dimethylphenylsulfanyl)-phenyl]piperazine as a compound with combined serotonin reuptake, 5-HT3 and 5-HT1A activity for the treatment of cognitive impairment |
US8969355B2 (en) | 2006-06-16 | 2015-03-03 | H. Lundbeck A/S | 1-[2-(2,4 dimethylphenylsulfanyl)-phenyl]piperazine as a compound with combined serotonin reuptake, 5-HT3 and 5-HT1a activity for the treatment of cognitive impairment |
US8722684B2 (en) | 2006-06-16 | 2014-05-13 | H. Lundbeck A/S | 1-[2-(2,4-dimethylphenylsulfanyl)-phenyl] piperazine as a compound with combined serotonin reuptake, 5-HT3 and 5-HT1A activity for the treatment of cognitive impairment |
US11458134B2 (en) | 2006-06-16 | 2022-10-04 | H. Lundbeck A/S | 1-[2-(2,4-dimeihylphenylsulfanyl)-phenyl]piperazine as a compound with combined serotonin reuptake, 5-HT3 and 5-HT1A activity for the treatment of cognitive impairment |
CN102617513A (zh) * | 2006-06-16 | 2012-08-01 | H.隆德贝克有限公司 | 作为用于治疗认知损伤的、具有结合的对血清素再吸收、5-ht3和5-ht1a活性的化合物的1-[2-(2,4-二甲基苯基硫烷基)-苯基]哌嗪 |
EA015287B1 (ru) * | 2006-06-16 | 2011-06-30 | Х. Лундбекк А/С | 1-[2-(2,4-диметилфенилсульфанил)фенил]пиперазин в качестве соединения с сочетанием активности в отношении повторного захвата серотонина, 5-нти 5-нтдля лечения когнитивного нарушения |
WO2020095912A1 (ja) * | 2018-11-06 | 2020-05-14 | 第一三共株式会社 | ベンズイミダゾール誘導体 |
Also Published As
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