DK1856114T3 - Benzisoxazol-derivater - Google Patents

Benzisoxazol-derivater Download PDF

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DK1856114T3
DK1856114T3 DK06710393.7T DK06710393T DK1856114T3 DK 1856114 T3 DK1856114 T3 DK 1856114T3 DK 06710393 T DK06710393 T DK 06710393T DK 1856114 T3 DK1856114 T3 DK 1856114T3
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methyl
oxy
benzisoxazol
piperidin
pyran
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DK06710393.7T
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Hirohide Noguchi
Isao Sakurada
Chikara Uchida
Nobuaki Waizumi
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Raqualia Pharma Inc
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/10—Laxatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/16—Central respiratory analeptics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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Claims (9)

1. Forbindelse af formlen (I):
(I) eller et farmaceutisk acceptabelt salt og ester deraf, hvor: A er -C(R2)(R3)- eller C3-C6-cycloalkylen; hvor nævnte C3-C6-cycloalkylen er usubsti-tueret eller substitueret med 1 til 4 substituenter uafhængigt af hinanden valgt fra gruppen bestående af halogen, hydroxy, Ci-C4-alkyl og Ci-C4-alkoxy; hvor R2 og R3 er uafhængigt af hinanden valgt fra gruppen bestående af halogen og Ci-C4-alkyl, hvor nævnte Ci-C4-alkyl er usubstitueret eller substitueret med 1 til 4 substituenter uafhængigt af hinanden valgt fra gruppen bestående af halogen, hydroxy og Ci-C4-alkoxy; eller R2 og R3, sammen med atomet til hvilke de er bundet til, danner en 3-6-leddet ring; hvor ringen er usubstitueret eller substitueret med 1 til 4 substituenter uafhængigt af hinanden valgt fra gruppen bestående af halogen, hydroxy, Ci-C4-alkyl og Ci-C4-alkoxy; B er -O- eller -N(H)-; R1 er carboxy, tetrazolyl, 5-oxo-l,2,4-oxadiazole-3-yl, 5-oxo-l,2,4-thiadiazole-3-yl eller hydroxy; R4 er en gruppe valgt fra gruppen bestående af C4-C6-cycloalkyl, heterocyclyl og -CH2-R5; hvor nævnte C4-C8-cycloalkyl er usubstitueret eller substitueret med 1 til 4 substituenter uafhængigt af hinanden valgt fra gruppen bestående af hydroxy, oxo og Ci-C4-alkoxy; hvor R5 er valgt fra gruppen bestående af trifluormethyl, isopropyl og C4-C8-cycloalkyl; hvor C4- nævnte C5-cycloalkyl er usubstitueret eller substitueret med 1 til 4 substituenter uafhængigt af hinanden valgt fra gruppen bestående af hydroxy, oxo, Ci-C4-alkoxy og hy-droxy-Ci-C4 alkyl; m er 1 eller 2; og n er 1 eller 2.
2. Forbindelse eller det farmaceutisk acceptable salt deraf ifølge krav 1, hvor: A er -C(R2)(R3)- eller C3-C6-cycloalkylen; hvor R2 og R3 er uafhængigt af hinanden valgt fra gruppen bestående af halogen og Ci-C4-alkyl; eller R2 og R3, sammen med atomet til hvilke de er bundet til, danner C3-C6-cycloalkyl eller heterocyclyl; hvor nævnte C3-C6-cycloalkyl og heterocyclyl er usubstituere-de; R1 er carboxy eller hydroxy; R4 er en gruppe valgt fra gruppen bestående af trifluoroethyl, isobutyl, cyclobutyl-methyl, cyclopentyl methyl, cyclopentyl, tetrahydro-2FI-pyran-4-yl, (1-hydroxycyclopentyl)methyl, 2-hydroxycyclopentyl, 2-methoxycyclopentyl, 2- oxocyclopentyl, 3-hydroxycyclopentyl, 2-hydroxycyclohexyl, 4-hydroxycyclohexyl, 4-(hydroxymethyl)cyclohexyl, [l-(hydroxymethyl)cyclobutyl]methyl og [1- (hydroxymethyl)cyclopentyl]methyl; m er 1 eller 2; og n er 1.
3. Forbindelse eller det farmaceutisk acceptable salt deraf ifølge krav 1, hvor: A er -C(R2)(R3)-; hvor R2 og R3 er uafhængigt af hinanden valgt fra gruppen bestående af fluor, methyl og ethyl; eller R2 og R3, sammen med atomet til hvilke de er bundet til, danner en ring valgt fra gruppen bestående af
y B er -0-R1 er carboxy; R4 er trifluoroethy, isobutyl eller cyclobutylmethyl; m er 1; og n er 1.
4. Forbindelse ifølge krav 1, som er valgt blandt: 4-{[4-({[4-(2,2,2-trifluorethoxy)-l,2-benzisoxazol-3-yl]oxy}methyl)piperidin-l- yl]methyl}tetrahydro-2/7-pyran-4-carboxylsyre; l-{[4-({[4-(2,2,2-trifluorethoxy)-l,2-benzisoxazol-3-yl]oxy}methyl)piperidin-l- yl]methyl}cyclobutane-carboxylsyre; 2.2- dimethyl-3-[4-({[4-(2,2,2-trifluorethoxy)-l,2-benzisoxazol-3-yl]oxy}methyl)piperidin-l-yl]-propionsyre; trans-4-{[4-({[4-(2,2,2-trifluorethoxy)-l,2-benzisoxazol-3-yl]oxy>methyl)piperidin- l-yl]methyl}-cyclohexancarboxylsyre 4-{2-[4-({[4-(2,2,2-trifluorethoxy)-l,2-benzisoxazo!-3-yl]oxy>methyl)piperidin-l- yl]ethyl}tetrahydro-2/7-pyran-4-carboxylsyre; 2.2- difluor-3-[4-({[4-(2,2,2-trifluorethoxy)-l,2-benzisoxazol-3-yl]oxy>methyl)piperidin-l-yl]propionsyre; 4-{[4-(2-{[4-(2,2,2-trifluorethoxy)-l,2-benzisoxazol-3-yl]oxy>ethyl)piperidin-l- yl]methyl}tetrahydro-2A7-pyran-4-carboxylsyre; 4-[((4-{[(4-isobutoxy-l,2-benzisoxazol-3-yl)oxy]methyl>piperidin-l- yl)methyl]tetrahydro-2H-pyran-4-carboxylsyre; l-[((4-{[(4-isobutoxy-l,2-benzisoxazol-3-yl)oxy]methyl>piperidin-l- yl)methyl]cyclobutanecarboxylsyre; 4-[2-(4-{[(4-isobutoxy-l,2-benzisoxazol-3-yl)oxy]methyl}piperidin-l- yl)ethyl]tetrahydro-2H-pyran-4-carboxylsyre; frans-4-[(4-{[(4-isobutoxy-l,2-benzisoxazol-3-yl)oxy]methyl}piperidin-l- yl)methyl]cyclohexancarboxylsyre; 4-[((4-{[(4-isobutoxy-l,2-benzisoxazol-3-yl)amino]methyl}piperidin-l- yl)methyl]tetrahydro-2H-pyran-4-carboxylsyre; 4-{[4-({[4-(cyclobutylmethoxy)-l,2-benzisoxazol-3-yl]oxy}methyl)piperidin-l- yl]methyl}tetrahydro-2H-pyran-4-carboxylsyre; 3- [4-({[4-(cyclobutylmethoxy)-l,2-benzisoxazol-3-yl]oxy}methyl)piperidin-l-yl]- 2.2- dimethylpropionsyre; og 4- {[4-({[4-(2,2,2-trifluorethoxy)-l,2-benzisoxazol-3-yl]amino>methyl)piperidin-l-yl]methyl}tetrahydro-2H-pyran-4-carboxylsyre; eller et farmaceutisk acceptabelt salt deraf.
5. Forbindelse ifølge krav 1, som er valgt blandt: 4-{[4-({[4-(2,2i2-trifluorethoxy)-l,2-benzisoxazol-3-yl]oxy}methyl)piperidin-l- yl]methyl}tetrahydro-2H-pyran-4-carboxylsyre; l'{[4-({[4-(2,2i2-trifluorethoxy)-l,2-benzisoxazol-3-yl]oxy}methyl)piperidin-l- yl]methyl}cyclobutan-carboxylsyre; 2,2-dimethyl-3-[4-({[4-(2,2,2-trifluorethoxy)-l,2-benzisoxazol-3- yi]oxy>methyl)piperidin-l-yl]-propionsyre; trans-4-{[4-({[4-(2/2/2-trifluorethoxy)-l/2-benzisoxazol-3-yl]oxy>methyl)piperidin-1-yl] methyl >-cyclohexancarboxylsyre 4-{2-[4-({[4-(2,2,2-trifluorethoxy)-l,2-benzisoxazol-3-yl]oxy>methyl)piperidin-l- yl]ethyl}tetrahydro-2A7-pyran-4-carboxylsyre; 4-[((4-{[(4-isobutoxy-l,2-benzisoxazol-3-yl)oxy]methyl}piperidin-l- yl)methyl]tetrahydro-2H-pyran-4-carboxylsyre; l-[((4-{[(4-isobutoxy-l,2-benzisoxazol-3-yl)oxy]methyl}piperidin-l- yl)methyl]cyclobutancarboxylsyre; 4-[2-(4-{[(4-isobutoxy-l,2-benzisoxazol-3-yl)oxy]methyl>piperidin-l- yl)ethyl]tetrahydro-2/-/-pyran-4-carboxylsyre; frans-4-[(4-{[(4-isobutoxy-l,2-benzisoxazol-3-yl)oxy]methyl}piperidin-l- yl)methyl]cyclohexancarboxylsyre; 4-[((4-{[(4-isobutoxy-l,2-benzisoxazol-3-yl)amino]methyl>piperidin-l- yl)methyl]tetrahydro-2/-/-pyran-4-carboxylsyre; 4-{[4-({[4-(cyclobutylmethoxy)-l,2-benzisoxazol-3-yl]oxy>methyl)piperidin-l- yl]methyl}tetrahydro-2H-pyran-4-carboxylsyre; 3- [4-({[4-(cyclobutylmethoxy)-l,2-benzisoxazol-3-yl]oxy>methyl)piperidin-l-yl]- 2.2- dimethylpropionsyre; og 4- {[4-({[4-(2,2,2-trifluorethoxy)-l,2-benzisoxazol-3-yl]amino>methyl)piperidin-l-yl]methyl}tetrahydro-2A7-pyran-4-carboxylsyre; eller et farmaceutisk acceptabelt salt deraf.
6. Farmaceutisk sammensætning omfattende forbindelsen eller det farmaceutisk acceptable salt deraf, ifølge et hvilket som helst af krav 1 til 5 og et farmaceutisk acceptabelt bærestof.
7. Farmaceutisk sammensætning ifølge krav 6, yderligere omfattende et andet farmakologisk aktivt middel.
8. Forbindelse ifølge formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge et hvilket som helst af krav 1 til 5, til anvendelse i behandling af en tilstand medieret af 5-FIT4-receptoraktivitet.
9. Forbindelse til anvendelse ifølge krav 8, hvor tilstanden er gastroøsofageal reflukssygdom, gastrointestinal sygdom, gastisk bevægelseslidelse, ikke-ulcerøs dyspepsi, funktionel dyspepsi, irritabel tyktarm (IBS), forstoppelse, dyspepsi, øsofagit, gastroøsofageal sygdom, kvalme, centralnervesystem sygdom, Alzheimers sygdom, kognitiv lidelse, opkastning, migræne, neurologisk sygdom, smerte, cardiovaskulær lidelser, hjertesvigt, hjertearrhytmi, diabetes eller apnø-syndrom.
DK06710393.7T 2005-02-25 2006-02-15 Benzisoxazol-derivater DK1856114T3 (da)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US65665305P 2005-02-25 2005-02-25
US71597705P 2005-09-09 2005-09-09
PCT/IB2006/000313 WO2006090224A1 (en) 2005-02-25 2006-02-15 Benzisoxazole derivatives

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DK1856114T3 true DK1856114T3 (da) 2014-11-17

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US (1) US8816090B2 (da)
EP (1) EP1856114B1 (da)
JP (2) JP4970290B2 (da)
CA (1) CA2598516C (da)
DK (1) DK1856114T3 (da)
ES (1) ES2523459T3 (da)
WO (1) WO2006090224A1 (da)

Families Citing this family (13)

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GB0525068D0 (en) 2005-12-08 2006-01-18 Novartis Ag Organic compounds
AU2009352490B2 (en) 2009-09-14 2013-06-20 Suven Life Sciences Limited 1, 2-dihydro-2-oxoquinoline compounds as 5-HT 4 receptor ligands
CN102762554A (zh) 2010-02-16 2012-10-31 辉瑞大药厂 5-ht4受体的部分激动剂(r)-4-((4-((4-(四氢呋喃-3-基氧基)苯并[d]异*唑-3-基氧基)甲基)哌啶-1-基)甲基)四氢-2h-吡喃-4-醇
KR101671341B1 (ko) 2011-02-25 2016-11-01 주식회사유한양행 다이아미노피리미딘 유도체 및 그의 제조방법
EP2688648B1 (en) * 2011-03-23 2016-01-06 RaQualia Pharma Inc. A 5-ht4 receptor agonist as a prokinetic agent
EP2710002B1 (en) 2011-05-18 2017-03-01 RaQualia Pharma Inc Polymorph form of 4-{[4-({[4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazol-3-yl]oxy}methyl)piperidin-1-yl]methyl}-tetrahydro-2h-pyran-4-carboxylic acid
PL2758394T3 (pl) 2011-09-19 2015-08-31 Suven Life Sciences Ltd Związki heteroarylowe jako ligandy receptora 5-HT4
WO2014080633A1 (en) 2012-11-21 2014-05-30 Raqualia Pharma Inc. Polymorph forms
ES2674993T3 (es) 2013-03-20 2018-07-05 Suven Life Sciences Limited Derivados de 5-amino-quinolina-8-carboxamida como agonistas del receptor 5-HT4
EP3099675B1 (en) 2013-12-16 2018-02-14 Suven Life Sciences Limited Indazole compounds as 5-ht4 receptor agonists
CA2948890C (en) 2014-05-16 2022-05-10 Raqualia Pharma Inc. 5-ht4 receptor agonist for gastroparesis
KR102471082B1 (ko) * 2014-05-20 2022-11-25 라퀄리아 파마 인코포레이티드 벤즈이소옥사졸 유도체염
SI3265459T1 (sl) 2015-02-13 2019-09-30 Suven Life Sciences Limited, Amidne spojine kot 5-HT4 receptor agonisti

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PT1054885E (pt) * 1998-02-09 2007-10-03 Duphar Int Res Derivativos de benzisoxazole tendo uma actividade d4-antagonista

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EP1856114B1 (en) 2014-08-20
JP5509236B2 (ja) 2014-06-04
JP2008531539A (ja) 2008-08-14
EP1856114A1 (en) 2007-11-21
JP4970290B2 (ja) 2012-07-04
US20080207690A1 (en) 2008-08-28
CA2598516C (en) 2010-05-11
JP2012144547A (ja) 2012-08-02
US8816090B2 (en) 2014-08-26
WO2006090224A1 (en) 2006-08-31
CA2598516A1 (en) 2006-08-31

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