CA2347469C - Esters of (+)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 100,907 - Google Patents

Esters of (+)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 100,907 Download PDF

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Publication number
CA2347469C
CA2347469C CA002347469A CA2347469A CA2347469C CA 2347469 C CA2347469 C CA 2347469C CA 002347469 A CA002347469 A CA 002347469A CA 2347469 A CA2347469 A CA 2347469A CA 2347469 C CA2347469 C CA 2347469C
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Canada
Prior art keywords
compound
ethyl
fluorophenyl
piperidinemethanol
dimethoxyphenyl
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Expired - Fee Related
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CA002347469A
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English (en)
French (fr)
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CA2347469A1 (en
Inventor
Albert A. Carr
Luc E. Van Hijfte
Raymond W. Kosley, Jr.
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Aventis Pharmaceuticals Inc
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Aventis Pharmaceuticals Inc
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Publication of CA2347469A1 publication Critical patent/CA2347469A1/en
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Publication of CA2347469C publication Critical patent/CA2347469C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • 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
    • A61P9/06—Antiarrhythmics
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Psychiatry (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Addiction (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA002347469A 1998-10-14 1998-10-14 Esters of (+)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 100,907 Expired - Fee Related CA2347469C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1998/021608 WO2000021930A1 (en) 1998-10-14 1998-10-14 Esters of (+)-alpha-( 2,3- dimethoxyphenyl) -1-[2-(4- fluorophenyl) ethyl]-4- piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 110,907

Publications (2)

Publication Number Publication Date
CA2347469A1 CA2347469A1 (en) 2000-04-20
CA2347469C true CA2347469C (en) 2006-02-28

Family

ID=22268079

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002347469A Expired - Fee Related CA2347469C (en) 1998-10-14 1998-10-14 Esters of (+)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 100,907

Country Status (21)

Country Link
EP (1) EP1121345A1 (ru)
JP (1) JP2002527422A (ru)
KR (1) KR100515429B1 (ru)
CN (1) CN1160333C (ru)
AU (1) AU1083099A (ru)
BR (1) BR9816049A (ru)
CA (1) CA2347469C (ru)
CZ (1) CZ20011331A3 (ru)
EA (1) EA003667B1 (ru)
EE (1) EE200100219A (ru)
HK (1) HK1039332A1 (ru)
HR (1) HRP20010278A2 (ru)
HU (1) HUP0200517A3 (ru)
IL (2) IL142479A0 (ru)
NO (1) NO320417B1 (ru)
NZ (1) NZ510631A (ru)
PL (1) PL193306B1 (ru)
SK (1) SK5082001A3 (ru)
TR (1) TR200101047T2 (ru)
UA (1) UA57859C2 (ru)
WO (1) WO2000021930A1 (ru)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020099076A1 (en) * 2000-05-25 2002-07-25 Richard Scheyer D. Use of (+)-a-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol or its prodrug in the treatment of symptoms of dementia and dopamine induced psychosis
CN102241667B (zh) * 2010-05-14 2013-10-23 中国人民解放军军事医学科学院毒物药物研究所 1-[(4-羟基哌啶-4基)甲基]吡啶-2(1h)-酮衍生物及其制备方法和用途
CN106892897A (zh) * 2015-12-21 2017-06-27 上海科胜药物研发有限公司 一种羟哌吡酮游离碱新晶型及其制备方法
CN106928187A (zh) * 2015-12-31 2017-07-07 上海奥博生物医药技术有限公司 一种盐酸羟哌吡酮新晶型及其制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU652759B2 (en) * 1990-06-01 1994-09-08 Aventisub Ii Inc. (+)-alpha-(2,3-dimethoxyphenyl)-1-(2-(4-fluorophenyl)ethyl)- 4-piperidinemethanol

Also Published As

Publication number Publication date
NZ510631A (en) 2003-07-25
UA57859C2 (ru) 2003-07-15
HUP0200517A3 (en) 2002-12-28
CN1160333C (zh) 2004-08-04
EA003667B1 (ru) 2003-08-28
EA200100361A1 (ru) 2001-10-22
NO20011805L (no) 2001-06-08
CA2347469A1 (en) 2000-04-20
SK5082001A3 (en) 2001-11-06
PL347318A1 (en) 2002-03-25
CN1314887A (zh) 2001-09-26
AU1083099A (en) 2000-05-01
IL142479A0 (en) 2002-03-10
EE200100219A (et) 2002-08-15
PL193306B1 (pl) 2007-01-31
EP1121345A1 (en) 2001-08-08
NO20011805D0 (no) 2001-04-09
HRP20010278A2 (en) 2002-06-30
HK1039332A1 (en) 2002-04-19
HUP0200517A2 (en) 2002-06-29
JP2002527422A (ja) 2002-08-27
KR100515429B1 (ko) 2005-09-20
KR20010106517A (ko) 2001-11-29
IL142479A (en) 2006-06-11
NO320417B1 (no) 2005-12-05
CZ20011331A3 (cs) 2001-08-15
WO2000021930A1 (en) 2000-04-20
TR200101047T2 (tr) 2001-08-21
BR9816049A (pt) 2001-07-03

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EP1289527B1 (en) (+)-alpha-(2,3-dimethoxyphenyl)-1(2-(4-fluorophenyl)ethyl)-4-piperidinemethanol or its prodrug to treat dementia or cognitive impairment
AU2001264842A1 (en) Use of (+)-alpha -(2,3-dimethoxyphenyl)-1-(2-(4-fluorophenyl)ethyl)-4- piperidinemerthanol or its prodrug in the treatment of symptoms of dementia and dopamine induced psychosis
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