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-ht3

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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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Spain
Prior art keywords
ht1a
affinity
cns disorders
arylpiperazine derivatives
treating cns
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ES009902042A
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ES2154605B1 (es
Inventor
Rodriguez Maria Luz Lopez
Cazorla Ignacio D Tejada
Ortega Maria Jose Morcillo
Bellinda Benhamusalama
Atance Jose Antonio Ramos
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Universidad Complutense de Madrid
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Universidad Complutense de Madrid
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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).
ES9902042A 1999-09-14 1999-09-14 Nuevos derivados mixtos de bencimidazol-arilpiperazina con afinidad por los receptores serotoninergicos 5-ht1a y 5-ht3 Expired - Fee Related ES2154605B1 (es)

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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

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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

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ES2154605A1 true ES2154605A1 (es) 2001-04-01
ES2154605B1 ES2154605B1 (es) 2001-11-16

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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

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Cited By (16)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (5)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
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
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
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

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