CA2439838C - (2-hydroxy)ethyl-thioureas useful as modulators of alpha2b adrenergic receptors - Google Patents

(2-hydroxy)ethyl-thioureas useful as modulators of alpha2b adrenergic receptors Download PDF

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Publication number
CA2439838C
CA2439838C CA2439838A CA2439838A CA2439838C CA 2439838 C CA2439838 C CA 2439838C CA 2439838 A CA2439838 A CA 2439838A CA 2439838 A CA2439838 A CA 2439838A CA 2439838 C CA2439838 C CA 2439838C
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Canada
Prior art keywords
compound
accordance
methyl
bond
formula
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Expired - Fee Related
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CA2439838A
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English (en)
French (fr)
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CA2439838A1 (en
Inventor
Ken Chow
Daniel W. Gil
Wenkui Ken Fang
Michael E. Garst
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Allergan Inc
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Allergan Inc
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Publication of CA2439838A1 publication Critical patent/CA2439838A1/en
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Publication of CA2439838C publication Critical patent/CA2439838C/en
Anticipated expiration legal-status Critical
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04Derivatives of thiourea
    • C07C335/06Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
    • C07C335/10Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04Derivatives of thiourea
    • C07C335/06Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
    • C07C335/08Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04Derivatives of thiourea
    • C07C335/14Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of rings other than six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/06Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/06Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/18Systems containing only non-condensed rings with a ring being at least seven-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2439838A 2001-02-27 2002-02-19 (2-hydroxy)ethyl-thioureas useful as modulators of alpha2b adrenergic receptors Expired - Fee Related CA2439838C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/794,874 2001-02-27
US09/794,874 US6534542B2 (en) 2001-02-27 2001-02-27 (2-hydroxy)ethyl-thioureas useful as modulators of α2B adrenergic receptors
PCT/US2002/005021 WO2002068384A2 (en) 2001-02-27 2002-02-19 (2-hydroxy)ethyl-thioureas useful as modulators of alpha2b adrenergic receptors

Publications (2)

Publication Number Publication Date
CA2439838A1 CA2439838A1 (en) 2002-09-06
CA2439838C true CA2439838C (en) 2012-01-24

Family

ID=25163943

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2439838A Expired - Fee Related CA2439838C (en) 2001-02-27 2002-02-19 (2-hydroxy)ethyl-thioureas useful as modulators of alpha2b adrenergic receptors

Country Status (6)

Country Link
US (1) US6534542B2 (enExample)
EP (1) EP1381593A2 (enExample)
JP (1) JP4159363B2 (enExample)
AU (1) AU2002242203B2 (enExample)
CA (1) CA2439838C (enExample)
WO (1) WO2002068384A2 (enExample)

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US20060280774A1 (en) * 1995-06-02 2006-12-14 Allergan, Inc. Compositions and methods for treating glaucoma
US5869079A (en) * 1995-06-02 1999-02-09 Oculex Pharmaceuticals, Inc. Formulation for controlled release of drugs by combining hydrophilic and hydrophobic agents
US6329369B1 (en) * 1997-12-04 2001-12-11 Allergan Sales, Inc. Methods of treating pain and other conditions
US6726918B1 (en) 2000-07-05 2004-04-27 Oculex Pharmaceuticals, Inc. Methods for treating inflammation-mediated conditions of the eye
ES2250504T3 (es) 2000-11-29 2006-04-16 Allergan Inc. Prevencion del rechazo de injerto en el ojo.
US7091232B2 (en) * 2002-05-21 2006-08-15 Allergan, Inc. 4-(substituted cycloalkylmethyl) imidazole-2-thiones, 4-(substituted cycloalkenylmethyl) imidazole-2-thiones, 4-(substituted cycloalkylmethyl) imidazol-2-ones and 4-(substituted cycloalkenylmethyl) imidazol-2-ones and related compounds
US7276522B2 (en) * 2002-05-21 2007-10-02 Allergan, Inc. 4-(substituted cycloalkylmethyl) imidazole-2-thiones, 4-(substituted cycloalkenylmethyl) imidazole-2-thiones, 4-(substituted cycloalkylmethyl) imidazol-2-ones, 4-(substituted cycloalkenylmethyl) imidazol-2-ones and related compounds
US7323485B2 (en) * 2002-05-21 2008-01-29 Allergan, Inc. 4-(substituted cycloalkylmethyl) imidazole-2-thiones, 4-(substituted cycloalkenylmethyl) imidazole-2-thiones, 4-(substituted cycloalkylmethyl) imidazol-2-ones and 4-(substituted cycloalkenylmethyl) imidazol-2-ones and related compounds
US7358269B2 (en) 2002-05-21 2008-04-15 Allergan, Inc. 2-((2-Thioxo-2,3-dihydro-1H-imidazol-4-yl)methyl)-3,4-dihydronapthalen-1(2H)-one
US20050048099A1 (en) 2003-01-09 2005-03-03 Allergan, Inc. Ocular implant made by a double extrusion process
US20050244469A1 (en) 2004-04-30 2005-11-03 Allergan, Inc. Extended therapeutic effect ocular implant treatments
EP1791833A2 (en) * 2004-09-24 2007-06-06 Allergan, Inc. 4-(condensed cyclicmethyl)-imidazole-2-thiones acting as alpha2 adrenergic agonists
BRPI0516025A (pt) 2004-09-24 2008-08-19 Allergan Sales Inc 4-(heteroaril-metil e heteroaril-metil substituìda)-imidazol-2-tionas que atuam como agonistas alfa2 adrenérgicos
US20070178138A1 (en) * 2006-02-01 2007-08-02 Allergan, Inc. Biodegradable non-opthalmic implants and related methods
US20070298073A1 (en) * 2006-06-23 2007-12-27 Allergan, Inc. Steroid-containing sustained release intraocular implants and related methods
US8802128B2 (en) 2006-06-23 2014-08-12 Allergan, Inc. Steroid-containing sustained release intraocular implants and related methods
WO2008014299A2 (en) * 2006-07-27 2008-01-31 Allergan, Inc. Use of an alpha2-agonist composition for the treatment of hyperlipidemia
AU2007337097A1 (en) 2006-12-22 2008-07-03 Allergan, Inc. Alpha-2B adrenergic receptor agonist and serotonin-norepinephrine reuptake inhibitor compositions for treating chronic pain
US20120083508A1 (en) 2006-12-22 2012-04-05 Allergan, Inc. Alpha-2b receptor agonist and anticonvulsant compositions for treating chronic pain
US20080153927A1 (en) * 2006-12-22 2008-06-26 Allergan, Inc. Alpha-2b receptor agonist and relaxant compositions for treating gastrointestinal motility disorders
US20080153825A1 (en) * 2006-12-22 2008-06-26 Allergan Inc. Alpha-2b receptor agonist and 5ht4 serotonin receptor compositions for treating gastrointestinal motility disorders
US20080153874A1 (en) * 2006-12-22 2008-06-26 Allergan Inc. Alpha-2b receptor agonist and anticonvulsant compositions for treating chronic pain
US20080153881A1 (en) * 2006-12-22 2008-06-26 Allergan, Inc. Alpha-2b receptor agonist and acid reducer compositions for treating gastrointestinal motility disorders
WO2009052075A2 (en) * 2007-10-18 2009-04-23 Allergan, Inc. Method of treating motor disorders with alpha-2b adrenergic receptor agonists
US20100216857A1 (en) * 2007-10-18 2010-08-26 Luhrs Lauren M B Method of treating motor disorders with 4-(1-(2,3-dimethylphenyl)ethyl)-1h-imidazole-2(3h)-thione
US8455548B2 (en) * 2007-10-18 2013-06-04 Allergan, Inc. Method of treating sensorimotor disorders with alpha-2 adrenergic receptor agonists
CA2772354A1 (en) 2009-08-26 2011-03-10 Daniel W. Gil Method of treating compulsive disorders with alpha-2b adrenergic receptor agonists
RU2599495C2 (ru) 2010-08-16 2016-10-10 Аллерган, Инк. Способ активации регуляторных т-клеток агонистами альфа-2в адренергических рецепторов
CN109336917A (zh) * 2013-06-04 2019-02-15 塞勒创尼克斯公司 腈-取代的硅烷和电解质组合物和包含它们的电化学装置
WO2015037665A1 (ja) 2013-09-12 2015-03-19 信越化学工業株式会社 β-シクロラバンジュラール及びその誘導体の製造方法
CN105531251A (zh) * 2013-09-12 2016-04-27 信越化学工业株式会社 用于制备环薰衣草醇及其衍生物的方法
RU2552529C1 (ru) * 2013-11-29 2015-06-10 Федеральное государственное бюджетное учреждение "Медицинский радиологический научный центр" Министерства здравоохранения Российской Федерации (ФГБУ МРНЦ Минздрава России) Вазопрессорное средство
US12440821B2 (en) 2021-12-13 2025-10-14 Saudi Arabian Oil Company Method for tracing subterranean formations with oil-soluble organic molecular tracers and extracting them of from oil phases
US11725139B2 (en) 2021-12-13 2023-08-15 Saudi Arabian Oil Company Manipulating hydrophilicity of conventional dye molecules for water tracer applications
US12188350B2 (en) * 2022-06-08 2025-01-07 Saudi Arabian Oil Company Fluorescent dye oil tracer compositions

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US2161772A (en) * 1936-04-17 1939-06-06 Monsanto Chemicals Phenol stabilization
US3686303A (en) * 1967-04-20 1972-08-22 Du Pont Certain substituted cyclohexyl ureas and thioureas
SU795462A3 (ru) 1975-03-14 1981-01-07 Эдьт Дьедьесерведьесети Дьяр (Фирма) Способ получени тиокарбамидныхпРОизВОдНыХ
US5212176A (en) 1990-06-29 1993-05-18 Abbott Laboratories R(+)-terazosin
US5580892A (en) * 1993-10-22 1996-12-03 Allergan Method for using 2-(2-alkylphenylamino)-oxazolines as adrenergic agents
TWI283669B (en) 1999-06-10 2007-07-11 Allergan Inc Compounds and method of treatment having agonist-like activity selective at alpha 2B or 2B/2C adrenergic receptors
US6313172B1 (en) * 2000-04-13 2001-11-06 Allergan Sales, Inc. Methods and compositions for modulating alpha adrenergic receptor activity

Also Published As

Publication number Publication date
AU2002242203B2 (en) 2007-01-18
JP2004524312A (ja) 2004-08-12
WO2002068384A3 (en) 2003-03-06
US6534542B2 (en) 2003-03-18
EP1381593A2 (en) 2004-01-21
JP4159363B2 (ja) 2008-10-01
WO2002068384A2 (en) 2002-09-06
CA2439838A1 (en) 2002-09-06
US20020161051A1 (en) 2002-10-31

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Effective date: 20140219