CA2258044C - Muscarinic antagonists - Google Patents

Muscarinic antagonists Download PDF

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Publication number
CA2258044C
CA2258044C CA002258044A CA2258044A CA2258044C CA 2258044 C CA2258044 C CA 2258044C CA 002258044 A CA002258044 A CA 002258044A CA 2258044 A CA2258044 A CA 2258044A CA 2258044 C CA2258044 C CA 2258044C
Authority
CA
Canada
Prior art keywords
alkyl
compound
pharmaceutically acceptable
group
cycloalkyl
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
CA002258044A
Other languages
English (en)
French (fr)
Other versions
CA2258044A1 (en
Inventor
Joseph A. Kozlowski
Derek B. Lowe
Wei K. Chang
Sundeep Dugar
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.)
Merck Sharp and Dohme LLC
Original Assignee
Schering Corp
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 Schering Corp filed Critical Schering Corp
Publication of CA2258044A1 publication Critical patent/CA2258044A1/en
Application granted granted Critical
Publication of CA2258044C publication Critical patent/CA2258044C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
    • 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
    • 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
    • C07D211/36—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 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • 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
    • C07D295/08—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 singly bound oxygen or sulfur atoms
    • C07D295/084—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • C07D295/08—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 singly bound oxygen or sulfur atoms
    • C07D295/096—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered

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)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA002258044A 1996-07-01 1997-06-26 Muscarinic antagonists Expired - Fee Related CA2258044C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US67439196A 1996-07-01 1996-07-01
US08/674,391 1996-07-01
PCT/US1997/010696 WO1998000412A1 (en) 1996-07-01 1997-06-26 Muscarinic antagonists

Publications (2)

Publication Number Publication Date
CA2258044A1 CA2258044A1 (en) 1998-01-08
CA2258044C true CA2258044C (en) 2007-09-04

Family

ID=24706404

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002258044A Expired - Fee Related CA2258044C (en) 1996-07-01 1997-06-26 Muscarinic antagonists

Country Status (12)

Country Link
EP (1) EP0912534B1 (enExample)
JP (2) JP2000514060A (enExample)
KR (1) KR20000022380A (enExample)
AT (1) ATE224884T1 (enExample)
AU (1) AU717431B2 (enExample)
CA (1) CA2258044C (enExample)
DE (1) DE69715865T2 (enExample)
ES (1) ES2179353T3 (enExample)
HU (1) HUP9904167A3 (enExample)
IL (1) IL127858A0 (enExample)
NZ (1) NZ333322A (enExample)
WO (1) WO1998000412A1 (enExample)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9726736D0 (en) * 1997-12-18 1998-02-18 Zeneca Ltd Chemical compounds
US6528529B1 (en) 1998-03-31 2003-03-04 Acadia Pharmaceuticals Inc. Compounds with activity on muscarinic receptors
GB9914015D0 (en) * 1999-06-17 1999-08-18 Zeneca Ltd Chemical compounds
JP2002533447A (ja) * 1998-12-24 2002-10-08 アストラゼネカ・アクチエボラーグ 神経疾患の治療に有用な１，４−ジアザシクロヘプタン誘導体
GB9900078D0 (en) * 1999-01-05 1999-02-24 Zeneca Ltd Chemical compounds
GB9914022D0 (en) * 1999-06-17 1999-08-18 Zeneca Ltd Chemical compounds
GB9914024D0 (en) * 1999-06-17 1999-08-18 Zeneca Ltd Chemical compounds
GB9914025D0 (en) * 1999-06-17 1999-08-18 Zeneca Ltd Chemical compounds
US7067539B2 (en) * 2001-02-08 2006-06-27 Schering Corporation Cannabinoid receptor ligands
BR0214649A (pt) * 2001-12-03 2004-11-03 Hoffmann La Roche Derivados de aminotetralina como antagonistas do receptor muscarìnico
WO2004048322A1 (en) 2002-11-25 2004-06-10 Schering Corporation Cannabinoid receptor ligands
WO2005037830A1 (en) 2003-10-10 2005-04-28 Wyeth Piperidinylchromen-6-ylsulfonamide compounds as 5-hydroxytryptamine-6 ligands
ES2431524T3 (es) * 2004-04-13 2013-11-26 Incyte Corporation Derivados de piperazinilpiperidina como antagonistas de los receptores de quimiocinas
US7378415B2 (en) 2004-09-30 2008-05-27 Roche Palo Alto Llc Benzoxazine and quinoxaline derivatives and uses thereof
BRPI0515835A (pt) * 2004-12-21 2008-08-12 Hoffmann La Roche derivados de tetralina e de indano e seus usos
WO2006102958A1 (en) * 2005-03-29 2006-10-05 Newron Pharmaceuticals S.P.A. Substituted aminoalkyl- and amidoalkyl-benzopyran derivatives
CA2620333A1 (en) 2005-08-26 2007-03-01 Braincells, Inc. Neurogenesis by muscarinic receptor modulation
EP2258357A3 (en) 2005-08-26 2011-04-06 Braincells, Inc. Neurogenesis with acetylcholinesterase inhibitor
ATE499355T1 (de) 2005-11-03 2011-03-15 Hoffmann La Roche Arylsulfonylchromane als 5-ht6-inhibitoren
KR101064001B1 (ko) 2006-06-20 2011-09-08 에프. 호프만-라 로슈 아게 아릴설폰아미딜 테트랄린 유도체 및 이의 용도
CA2653758A1 (en) 2006-06-20 2007-12-27 F. Hoffmann-La Roche Ag Tetralin and indane derivatives and uses thereof
WO2007147763A1 (en) 2006-06-20 2007-12-27 F. Hoffmann-La Roche Ag Arylsulfonyl naphthalene derivatives and uses thereof
WO2010081851A1 (en) 2009-01-14 2010-07-22 Genoscience Pharma Piperidin-4-ylpiperazine compounds for the treatment of hcv infection
AU2011216950A1 (en) 2010-02-16 2012-08-23 Pfizer Inc. (R)-4-((4-((4-(tetrahydrofuran-3-yloxy) benzo[d]isoxazol-3-yloxy)methyl)piperidin-1-yl)methyl)tetrahydro-2H-pyran-4-ol, a partial agonist of 5-HT4 receptors
WO2017015349A1 (en) * 2015-07-20 2017-01-26 Chase Pharmaceuticals Corporation Muscarinic combination of a selective m2-antagonist and a peripheral non-selective antagonist for treating hypocholinergic disorders
MX386501B (es) * 2015-09-28 2025-03-19 Genentech Inc Compuestos terapeuticos y sus metodos de uso
WO2023283425A1 (en) 2021-07-09 2023-01-12 Plexium, Inc. Aryl compounds and pharmaceutical compositions that modulate ikzf2

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD113545A5 (enExample) * 1973-03-30 1975-06-12
DE3064285D1 (en) * 1979-09-28 1983-08-25 Beecham Group Plc Chromanol derivatives, a process for their preparation and a pharmaceutical composition comprising them
DK691488A (da) * 1987-12-14 1989-06-15 Beecham Group Plc Hidtil ukendte forbindelser
DK286990D0 (da) * 1990-12-04 1990-12-04 Lundbeck & Co As H Indanderivater
ES2164054T3 (es) * 1991-11-05 2002-02-16 Smithkline Beecham Corp Antagonistas de receptores de endotelina.
WO1994012493A1 (en) * 1992-11-25 1994-06-09 Sandoz, Ltd. 2,2-dialkyl- and 2,2-dialkyl-3,4-dihydro-3-hydroxy-2h-1-benzopyr ans, their use as pharmaceuticals

Also Published As

Publication number Publication date
ES2179353T3 (es) 2003-01-16
DE69715865D1 (de) 2002-10-31
EP0912534A1 (en) 1999-05-06
AU3495397A (en) 1998-01-21
HUP9904167A3 (en) 2000-07-28
HUP9904167A2 (hu) 2000-05-28
IL127858A0 (en) 1999-10-28
ATE224884T1 (de) 2002-10-15
WO1998000412A1 (en) 1998-01-08
JP2000514060A (ja) 2000-10-24
EP0912534B1 (en) 2002-09-25
JP2009040778A (ja) 2009-02-26
KR20000022380A (ko) 2000-04-25
NZ333322A (en) 2000-06-23
DE69715865T2 (de) 2003-08-07
AU717431B2 (en) 2000-03-23
CA2258044A1 (en) 1998-01-08

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