CA2326804C - Compounds with activity on muscarinic receptors - Google Patents

Compounds with activity on muscarinic receptors Download PDF

Info

Publication number
CA2326804C
CA2326804C CA002326804A CA2326804A CA2326804C CA 2326804 C CA2326804 C CA 2326804C CA 002326804 A CA002326804 A CA 002326804A CA 2326804 A CA2326804 A CA 2326804A CA 2326804 C CA2326804 C CA 2326804C
Authority
CA
Canada
Prior art keywords
compound
alkyl
alkoxy
pharmaceutically acceptable
nr3r4
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.)
Expired - Fee Related
Application number
CA002326804A
Other languages
English (en)
French (fr)
Other versions
CA2326804A1 (en
Inventor
Mark Robert Brann
Terri Messier
Erika Anne Currier
Katharan Lauri Duggento
Mikael Friberg
Niels Skjaerbaek
Tracy Spalding
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Acadia Pharmaceuticals Inc
Original Assignee
Acadia Pharmaceuticals Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Acadia Pharmaceuticals Inc filed Critical Acadia Pharmaceuticals Inc
Priority to CA002543133A priority Critical patent/CA2543133A1/en
Publication of CA2326804A1 publication Critical patent/CA2326804A1/en
Application granted granted Critical
Publication of CA2326804C publication Critical patent/CA2326804C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • A61P25/28—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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA002326804A 1998-03-31 1999-03-31 Compounds with activity on muscarinic receptors Expired - Fee Related CA2326804C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA002543133A CA2543133A1 (en) 1998-03-31 1999-03-31 Compounds with activity on muscarinic receptors

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US8013398P 1998-03-31 1998-03-31
US60/080,133 1998-03-31
PCT/US1999/007057 WO1999050247A1 (en) 1998-03-31 1999-03-31 Compounds with activity on muscarinic receptors

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA002543133A Division CA2543133A1 (en) 1998-03-31 1999-03-31 Compounds with activity on muscarinic receptors

Publications (2)

Publication Number Publication Date
CA2326804A1 CA2326804A1 (en) 1999-10-07
CA2326804C true CA2326804C (en) 2006-05-02

Family

ID=22155464

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002326804A Expired - Fee Related CA2326804C (en) 1998-03-31 1999-03-31 Compounds with activity on muscarinic receptors

Country Status (14)

Country Link
EP (1) EP1068185A1 (ru)
JP (1) JP2002509918A (ru)
KR (2) KR20060120715A (ru)
CN (1) CN1303376A (ru)
AR (1) AR014974A1 (ru)
AU (1) AU762726B2 (ru)
BR (1) BR9909277A (ru)
CA (1) CA2326804C (ru)
MX (1) MXPA00009569A (ru)
NO (1) NO319835B1 (ru)
NZ (2) NZ507204A (ru)
RU (2) RU2230740C2 (ru)
WO (1) WO1999050247A1 (ru)
ZA (1) ZA200005149B (ru)

Families Citing this family (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6528529B1 (en) 1998-03-31 2003-03-04 Acadia Pharmaceuticals Inc. Compounds with activity on muscarinic receptors
US6624162B2 (en) 2001-10-22 2003-09-23 Pfizer Inc. Imidazopyridine compounds as 5-HT4 receptor modulators
US7307075B2 (en) 2001-12-28 2007-12-11 Acadia Pharmaceuticals Inc. Tetrahydroquinoline analogues as muscarinic agonists
US7550459B2 (en) 2001-12-28 2009-06-23 Acadia Pharmaceuticals, Inc. Tetrahydroquinoline analogues as muscarinic agonists
MXPA03000145A (es) 2002-01-07 2003-07-15 Pfizer Compuestos de oxo u oxi-piridina como moduladores de receptores 5-ht4.
GB0211230D0 (en) 2002-05-16 2002-06-26 Medinnova Sf Treatment of heart failure
DOP2003000703A (es) 2002-09-20 2004-03-31 Pfizer Compuestos de imidazopiradina como agonistas del receptor 5-ht4
JP2006502180A (ja) 2002-09-20 2006-01-19 ファイザー株式会社 ５−ｈｔ４レセプターモジュレーターとしてのｎ−置換されたピペリジニル−イミダゾピリジン化合物
HU227534B1 (en) 2003-08-04 2011-08-29 Richter Gedeon Nyrt (thio)carbamoyl-cyclohexane derivatives, process for producing them and pharmaceutical compositions containing them
EP1651235A4 (en) * 2003-08-05 2008-12-17 Samaritan Pharmaceuticals Inc SIGMA-1 RECEPTOR LIGAND WITH ACETYLCHOLINESTERASE-INHIBITORY PROPERTIES
WO2005033079A1 (ja) 2003-09-30 2005-04-14 Eisai Co., Ltd. ヘテロ環化合物を含有する新規な抗真菌剤
BRPI0510453A (pt) 2004-04-30 2007-10-30 Warner Lambert Co composto substituìdos com morfolina para o tratamento de distúrbios do sistema nervoso central
KR100875558B1 (ko) 2004-06-15 2008-12-23 화이자 인코포레이티드 벤즈이미다졸론 카복실산 유도체
US7737163B2 (en) 2004-06-15 2010-06-15 Pfizer Inc. Benzimidazolone carboxylic acid derivatives
UA89514C2 (ru) 2004-12-30 2010-02-10 Janssen Pharmaceutica Nv Производные фениламидов 4-(бензил)-пиперазин-1-карбоновых кислот и родственные соединения как модуляторы гидролазы амидов жирных кислот для лечения тревоги, боли и других состояний
EP2395000A1 (en) 2004-12-30 2011-12-14 Astex Therapeutics Limited Benzimidazole compounds that modulate the activity of CDK, GSK and aurora kinases
WO2006106711A1 (ja) 2005-03-30 2006-10-12 Eisai R & D Management Co., Ltd. ピリジン誘導体を含有する抗真菌剤
US8097610B2 (en) 2005-08-26 2012-01-17 Shionogi & Co., Ltd. Derivative having PPAR agonistic activity
EP2258359A3 (en) 2005-08-26 2011-04-06 Braincells, Inc. Neurogenesis by muscarinic receptor modulation with sabcomelin
JP2009506069A (ja) 2005-08-26 2009-02-12 ブレインセルス，インコーポレイティド ムスカリン性受容体調節による神経発生
TWI385169B (zh) 2005-10-31 2013-02-11 Eisai R&D Man Co Ltd 經雜環取代之吡啶衍生物及含有彼之抗真菌劑
JP5474354B2 (ja) 2005-12-30 2014-04-16 アステックス、セラピューティックス、リミテッド 医薬化合物
US8435970B2 (en) 2006-06-29 2013-05-07 Astex Therapeutics Limited Pharmaceutical combinations of 1-cyclopropyl-3-[3-(5-morpholin-4-ylmethyl-1H-benzoimidazol-2-yl)-1H-pyrazol-4-yl]-urea
CL2008000119A1 (es) 2007-01-16 2008-05-16 Wyeth Corp Compuestos derivados de pirazol, antagonistas del receptor nicotinico de acetilcolina; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como demencia senil, alzheimer y esquizofrenia.
HUP0700353A2 (en) 2007-05-18 2008-12-29 Richter Gedeon Nyrt Metabolites of (thio)carbamoyl-cyclohexane derivatives
US7875610B2 (en) 2007-12-03 2011-01-25 Richter Gedeon Nyrt. Pyrimidinyl-piperazines useful as D3/D2 receptor ligands
US8513287B2 (en) 2007-12-27 2013-08-20 Eisai R&D Management Co., Ltd. Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same
CN102118970A (zh) 2008-07-16 2011-07-06 吉瑞工厂 包含多巴胺受体配体的药物制剂
HU230067B1 (hu) 2008-12-17 2015-06-29 Richter Gedeon Nyrt Új piperazin só és eljárás előállítására
HUP0800766A2 (en) 2008-12-18 2010-11-29 Richter Gedeon Vegyeszet Process for the preparation of piperazine derivatives
HUP0800765A2 (en) 2008-12-18 2010-11-29 Richter Gedeon Nyrt A new process for the preparation of piperazine derivatives and their hydrochloric salts
UA108233C2 (uk) 2010-05-03 2015-04-10 Модулятори активності гідролази амідів жирних кислот
GB201106817D0 (en) 2011-04-21 2011-06-01 Astex Therapeutics Ltd New compound
CN102558026A (zh) * 2011-12-27 2012-07-11 盛世泰科生物医药技术(苏州)有限公司 关于4-n-丁基-1-[4-(2-甲基苯基)-4-酮-1-丁基]哌啶的合成及工艺优化
US8912197B2 (en) 2012-08-20 2014-12-16 Forest Laboratories Holdings Ltd. Crystalline form of carbamoyl-cyclohexane derivatives
CN102997438A (zh) * 2012-10-16 2013-03-27 李誊 改善热量利用率的电热水器控制方法
GB201218850D0 (en) 2012-10-19 2012-12-05 Astex Therapeutics Ltd Bicyclic heterocycle compounds and their uses in therapy
US9980973B2 (en) 2012-10-19 2018-05-29 Astex Therapeutics Limited Bicyclic heterocycle compounds and their uses in therapy
GB201218862D0 (en) 2012-10-19 2012-12-05 Astex Therapeutics Ltd Bicyclic heterocycle compounds and their uses in therapy
GB201218864D0 (en) 2012-10-19 2012-12-05 Astex Therapeutics Ltd Bicyclic heterocycle compounds and their uses in therapy
PE20161035A1 (es) 2013-03-15 2016-11-13 Global Blood Therapeutics Inc Compuestos y usos de estos para la modulacion de la hemoglobina
EA201992707A1 (ru) 2013-11-18 2020-06-30 Глобал Блад Терапьютикс, Инк. Соединения и их применения для модуляции гемоглобина
RS62301B1 (sr) 2013-12-20 2021-09-30 Astex Therapeutics Ltd Biciklična heterociklična jedinjenja i njihove upotrebe u terapiji
US11274087B2 (en) 2016-07-08 2022-03-15 Richter Gedeon Nyrt. Industrial process for the preparation of cariprazine
AU2018289303B2 (en) 2017-06-20 2023-12-21 Imbria Pharmaceuticals, Inc. Compositions and methods for increasing efficiency of cardiac metabolism
US11547707B2 (en) 2019-04-10 2023-01-10 Richter Gedeon Nyrt. Carbamoyl cyclohexane derivatives for treating autism spectrum disorder
US11780811B2 (en) 2020-06-30 2023-10-10 Imbria Pharmaceuticals, Inc. Methods of synthesizing 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethyl pyridine-3-carboxylate
US11530184B2 (en) 2020-06-30 2022-12-20 Imbria Pharmaceuticals, Inc. Crystal forms of 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethyl pyridine-3-carboxylate
US11883396B2 (en) 2021-05-03 2024-01-30 Imbria Pharmaceuticals, Inc. Methods of treating kidney conditions using modified forms of trimetazidine

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2695295A (en) * 1952-12-19 1954-11-23 Mcneilab Inc Unsymmetrical n, n'-substituted ethylenediamine and piperazine compounds
GB874206A (en) * 1956-09-05 1961-08-02 Knoll Ag Basic derivatives of salicylamide
NL271658A (ru) * 1960-12-01
FR1382425A (fr) * 1963-01-14 1964-12-18 Ciba Geigy Procédé de préparation de diaza-cyclo-alcanes, entre autres de la 3-méthyl-4-phényl-1-(2-phénylmercapto-éthyl)-pipérazine
GB1053301A (ru) * 1963-01-14
US3488352A (en) * 1966-10-11 1970-01-06 Shulton Inc Basically substituted alkoxy anthranilamides,their corresponding 2-nitro compounds and derivatives thereof
FR1543944A (fr) * 1967-03-10 1968-10-31 Bruneau & Cie Lab Dérivés amidés de l'acide salicylique et leur préparation
DE2335432A1 (de) * 1973-07-12 1975-01-30 Boehringer Mannheim Gmbh 3,4-dihydro-2h-naphthalinon-(1)5-oxy-propyl-piperazin-derivate und verfahren zu ihrer herstellung
BE792187A (fr) * 1971-12-03 1973-03-30 Sumitomo Chemical Co Nouveaux derives d'alkylamines
GB1459506A (en) * 1974-02-18 1976-12-22 Wyeth John & Brother Ltd Piperidine derivatives
GB1498884A (en) * 1975-04-15 1978-01-25 Wyeth John & Brother Ltd Aminoacetamide-pyridyl-tetrahydropyridyl and-piperidyl derivatives
IL117149A0 (en) * 1995-02-23 1996-06-18 Schering Corp Muscarinic antagonists
US5889006A (en) * 1995-02-23 1999-03-30 Schering Corporation Muscarinic antagonists
PL331536A1 (en) * 1996-08-15 1999-07-19 Schering Corp Muscarinic antagonists with an etheric bond

Also Published As

Publication number Publication date
NO20004912D0 (no) 2000-09-29
KR20010042248A (ko) 2001-05-25
EP1068185A1 (en) 2001-01-17
CN1303376A (zh) 2001-07-11
NO319835B1 (no) 2005-09-19
AR014974A1 (es) 2001-04-11
AU762726B2 (en) 2003-07-03
WO1999050247A1 (en) 1999-10-07
CA2326804A1 (en) 1999-10-07
KR100672186B1 (ko) 2007-01-19
RU2278111C2 (ru) 2006-06-20
MXPA00009569A (es) 2002-08-06
KR20060120715A (ko) 2006-11-27
ZA200005149B (en) 2002-01-08
AU3218799A (en) 1999-10-18
NZ525108A (en) 2005-02-25
JP2002509918A (ja) 2002-04-02
BR9909277A (pt) 2001-10-16
RU2004107218A (ru) 2005-08-20
NZ507204A (en) 2003-12-19
RU2230740C2 (ru) 2004-06-20
NO20004912L (no) 2000-11-23

Similar Documents

Publication Publication Date Title
CA2326804C (en) Compounds with activity on muscarinic receptors
US7485651B2 (en) Compounds with activity on muscarinic receptors
DE60225162T2 (de) Phenylpiperazinderivate als serotonin wiederaufnahmehemmer
DE69705819T2 (de) Angiogenesis hemmende pyridazinamine
EP1119557B1 (de) Indeno-, naphtho- und benzocyclohepta-dihydrothiazol derivate, deren herstellung und deren verwendung als anorektische arzneimittel
SU1255050A3 (ru) Способ получени рацемических или стереоизомерных производных нафталин- или азанафталинкарбоксамидов
JP4012068B2 (ja) ムスカリンアンタゴニスト
JPH03181461A (ja) 抗不整脈剤
JP2009508963A (ja) アミド化合物および医薬組成物としてのその使用
US4539322A (en) Dihydropyridine derivatives and their use in treating heart conditions and hypertension
JP4076234B2 (ja) テトラヒドロベンズインドール化合物
JPH0283375A (ja) ２−置換ピペラジニル−２−（１，２−ベンズイソキサゾール−３−イル）酢酸誘導体
EP0682015A1 (en) Piperidine derivates and anti-platelet agents containing the same
NZ243337A (en) 1-piperidyl substituted quinoline derivatives and pharmaceutical compositions
DE69925160T2 (de) Arylpiperidin- und aryl-1,2,5,6-tetrahydropyridinamid-derivate mit 5ht1a rezeptor aktivität
CA2543133A1 (en) Compounds with activity on muscarinic receptors
EP0336555A1 (en) 4,5,6,7-Tetrahydroisothiazolo (4,5-c)pyridine derivatives and isomers
NZ270567A (en) N-(4-(trimethoxybenzyl)piperazin-1-ylalkyl) sulphonamide derivatives and pharmaceutical compositions
CN108329282B (zh) 一种苯基哌嗪类衍生物及其制备方法和应用
EP0578419B1 (en) Pyridine derivatives and pharmaceutical compositions containing them
CA2259218C (en) Tetrahydrobenzindole compound
JPH0673010A (ja) ピリジン誘導体
FR2717174A1 (fr) Utilisation de pipéridinoéthyl esters de l'acide 4-amino-5-chloro-2-méthoxybenzoïque comme 5-HT4 agonistes.
WO1996013488A1 (fr) Nouveau derive de benzodiazepinone et composition medicinale constituee de celui-ci

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed