CA2724788C - Hepatoprotectant acetaminophen mutual prodrugs - Google Patents

Hepatoprotectant acetaminophen mutual prodrugs Download PDF

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Publication number
CA2724788C
CA2724788C CA2724788A CA2724788A CA2724788C CA 2724788 C CA2724788 C CA 2724788C CA 2724788 A CA2724788 A CA 2724788A CA 2724788 A CA2724788 A CA 2724788A CA 2724788 C CA2724788 C CA 2724788C
Authority
CA
Canada
Prior art keywords
compound
acetaminophen
pharmaceutically acceptable
solvate
foregoing
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
CA2724788A
Other languages
English (en)
French (fr)
Other versions
CA2724788A1 (en
Inventor
Naweed Muhammad
Keith R. Bley
Jeffrey Tobias
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.)
Acorda Therapeutics Inc
Original Assignee
Acorda Therapeutics 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 Acorda Therapeutics Inc filed Critical Acorda Therapeutics Inc
Priority to CA2946445A priority Critical patent/CA2946445C/en
Publication of CA2724788A1 publication Critical patent/CA2724788A1/en
Application granted granted Critical
Publication of CA2724788C publication Critical patent/CA2724788C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • 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
    • A61P9/10—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Emergency Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Cardiology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Rheumatology (AREA)
  • Biomedical Technology (AREA)
  • Physiology (AREA)
  • Nutrition Science (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Toxicology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicinal Preparation (AREA)
CA2724788A 2008-05-20 2009-05-20 Hepatoprotectant acetaminophen mutual prodrugs Expired - Fee Related CA2724788C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2946445A CA2946445C (en) 2008-05-20 2009-05-20 Hepatoprotectant acetaminophen mutual prodrugs

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US5477708P 2008-05-20 2008-05-20
US61/054,777 2008-05-20
PCT/US2009/044749 WO2009143299A1 (en) 2008-05-20 2009-05-20 Hepatoprotectant acetaminophen mutual prodrugs

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA2946445A Division CA2946445C (en) 2008-05-20 2009-05-20 Hepatoprotectant acetaminophen mutual prodrugs

Publications (2)

Publication Number Publication Date
CA2724788A1 CA2724788A1 (en) 2009-11-26
CA2724788C true CA2724788C (en) 2016-12-06

Family

ID=41340540

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2724788A Expired - Fee Related CA2724788C (en) 2008-05-20 2009-05-20 Hepatoprotectant acetaminophen mutual prodrugs
CA2946445A Expired - Fee Related CA2946445C (en) 2008-05-20 2009-05-20 Hepatoprotectant acetaminophen mutual prodrugs

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2946445A Expired - Fee Related CA2946445C (en) 2008-05-20 2009-05-20 Hepatoprotectant acetaminophen mutual prodrugs

Country Status (12)

Country Link
US (3) US20110263545A1 (enExample)
EP (1) EP2285419A4 (enExample)
JP (6) JP5701750B2 (enExample)
KR (1) KR101717145B1 (enExample)
CN (1) CN102149412A (enExample)
AU (1) AU2009249071A1 (enExample)
BR (1) BRPI0912820A2 (enExample)
CA (2) CA2724788C (enExample)
IL (1) IL209384A0 (enExample)
MX (1) MX2010012647A (enExample)
RU (1) RU2010151951A (enExample)
WO (1) WO2009143299A1 (enExample)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5757864B2 (ja) 2008-05-20 2015-08-05 ニューロジェシックス， インコーポレイテッド 水溶性アセトアミノフェン類似体
KR101677126B1 (ko) * 2008-05-20 2016-11-22 노이로제스엑스, 인코포레이티드 탄산염 프로드러그 및 그것의 사용 방법
BRPI0912820A2 (pt) 2008-05-20 2015-10-13 Neurogesx Inc pró-fármacos de relação hepatoprotetora de acetaminofeno
AU2012312136B2 (en) * 2011-09-22 2017-06-29 Acorda Therapeutics, Inc. Acetaminophen conjugates, compositions and methods of use thereof
US20140179615A1 (en) * 2012-07-12 2014-06-26 Hainan Weikang Pharmaceutical (Qianshan) Co., Ltd. Glutathione and Acetaminophen Composition and Preparation Method Thereof
AU2014306759B2 (en) 2013-08-12 2018-04-26 Pharmaceutical Manufacturing Research Services, Inc. Extruded immediate release abuse deterrent pill
US10172797B2 (en) 2013-12-17 2019-01-08 Pharmaceutical Manufacturing Research Services, Inc. Extruded extended release abuse deterrent pill
US9492444B2 (en) 2013-12-17 2016-11-15 Pharmaceutical Manufacturing Research Services, Inc. Extruded extended release abuse deterrent pill
EP3169315B1 (en) 2014-07-17 2020-06-24 Pharmaceutical Manufacturing Research Services, Inc. Immediate release abuse deterrent liquid fill dosage form
US20170246194A1 (en) * 2014-08-15 2017-08-31 Purdue Pharma L.P. Acetaminophen-Containing Analgesic Formulations With Reduced Hepatotoxicity
US20160106737A1 (en) 2014-10-20 2016-04-21 Pharmaceutical Manufacturing Research Services, Inc. Extended Release Abuse Deterrent Liquid Fill Dosage Form
WO2021041800A1 (en) * 2019-08-30 2021-03-04 Remedy Diagnostics LLC Transdermal device comprising pain molecules

Family Cites Families (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4035507A (en) * 1975-04-17 1977-07-12 Interx Research Corporation Novel, transient pro-drug forms of L-DOPA to treat Parkinson's disease
GB1583602A (en) 1977-05-26 1981-01-28 Sterwin Ag N-acetyl-para-aminophenyl-n'-acetyl-amino-thioalkanoic acid ester derivatives
US4562024A (en) 1982-07-06 1985-12-31 Sterling Drug Inc. Process for preparing granulate containing poorly compressible medicinally active matter
CH654302A5 (de) * 1983-05-04 1986-02-14 Sandoz Ag Acylaminophenolderivate, ihre herstellung und arzneimittel, welche sie enthalten.
US5001115A (en) * 1989-05-17 1991-03-19 University Of Florida Prodrugs of biologically active hydroxyaromatic compounds
US5474757A (en) * 1992-10-16 1995-12-12 Rutgers University Prevention of acetaminophen overdose toxicity with organosulfur compounds
DE4327462A1 (de) * 1993-08-16 1995-02-23 Carl Heinrich Dr Weischer Neue N-Acetyl-p-Aminophenol-Derivate zur Bekämpfung von Schmerzzuständen
US5916910A (en) 1997-06-04 1999-06-29 Medinox, Inc. Conjugates of dithiocarbamates with pharmacologically active agents and uses therefore
US6710086B1 (en) 2000-02-25 2004-03-23 Medinox, Inc. Protected forms of pharmacologically active agents and uses therefor
AU6011301A (en) 2000-03-14 2001-09-24 Actelion Pharmaceuticals Ltd 1,2,3,4-tetrahydroisoquinoline derivatives
WO2001068069A2 (en) 2000-03-15 2001-09-20 King's College London Pharmaceutical composition comprising paracetamol
IT1319202B1 (it) 2000-10-12 2003-09-26 Nicox Sa Farmaci per le malattie a base infiammatoria.
US20030073618A1 (en) * 2001-02-08 2003-04-17 Kozhemyakin Leonid A. Compounds comprising disulfide-containing peptides and nitrogenous bases, and medical uses thereof
US7087600B2 (en) 2001-05-31 2006-08-08 Medarex, Inc. Peptidyl prodrugs and linkers and stabilizers useful therefor
IL158882A0 (en) 2001-06-05 2004-05-12 Control Delivery Sys Inc Sustained-release analgesic compounds
WO2003043657A1 (en) 2001-11-19 2003-05-30 Control Delivery Systems, Inc. Topical delivery of codrugs
US20050164994A1 (en) 2001-12-10 2005-07-28 Control Deliver Systems, Inc. Treatment of genitourinary tract disorders
US20030170286A1 (en) 2001-12-10 2003-09-11 Paul Ashton Treatment of genitourinary tract disorders
MXPA04006875A (es) 2002-01-18 2004-12-06 Control Delivery Sys Inc Sistema de gel polimerico para suministro controlado de cofarmacos.
US20040058946A1 (en) 2002-07-05 2004-03-25 Buchwald Stephen L. Abuse-resistant prodrugs of oxycodone and other pharmaceuticals
US7381721B2 (en) 2003-03-17 2008-06-03 Adolor Corporation Substituted piperidine compounds
AU2004278414B2 (en) 2003-10-01 2012-05-24 Adolor Corporation Spirocyclic heterocyclic derivatives and methods of their use
ATE497489T1 (de) 2003-11-12 2011-02-15 Applied Nanosystems Bv Nichtsymmetrisches geliermittel
US20050113294A1 (en) 2003-11-21 2005-05-26 Adolor Corporation. Carboxamide and amino derivatives and methods of their use
TW200616604A (en) 2004-08-26 2006-06-01 Nicholas Piramal India Ltd Nitric oxide releasing prodrugs containing bio-cleavable linker
US7598261B2 (en) 2005-03-31 2009-10-06 Adolor Corporation Spirocyclic heterocyclic derivatives and methods of their use
WO2007016108A1 (en) 2005-07-27 2007-02-08 Orexigen Therapeutics, Inc. Compositions for affecting weight loss
PA8720901A1 (es) 2006-03-24 2008-11-19 Wyeth Corp Tratamiento del dolor
JP2010511717A (ja) 2006-12-05 2010-04-15 ニューロジェシックス， インコーポレイテッド プロドラッグおよびその作成ならびに使用方法
JP5757864B2 (ja) 2008-05-20 2015-08-05 ニューロジェシックス， インコーポレイテッド 水溶性アセトアミノフェン類似体
KR101677126B1 (ko) 2008-05-20 2016-11-22 노이로제스엑스, 인코포레이티드 탄산염 프로드러그 및 그것의 사용 방법
BRPI0912820A2 (pt) 2008-05-20 2015-10-13 Neurogesx Inc pró-fármacos de relação hepatoprotetora de acetaminofeno

Also Published As

Publication number Publication date
BRPI0912820A2 (pt) 2015-10-13
CA2724788A1 (en) 2009-11-26
US20160326107A1 (en) 2016-11-10
US20190062273A1 (en) 2019-02-28
KR101717145B1 (ko) 2017-03-16
IL209384A0 (en) 2011-01-31
JP5701750B2 (ja) 2015-04-15
JP2021036001A (ja) 2021-03-04
CA2946445A1 (en) 2009-11-26
EP2285419A4 (en) 2012-05-02
CN102149412A (zh) 2011-08-10
KR20110011694A (ko) 2011-02-08
US20110263545A1 (en) 2011-10-27
US9951001B2 (en) 2018-04-24
CA2946445C (en) 2019-01-08
AU2009249071A1 (en) 2009-11-26
JP2011523645A (ja) 2011-08-18
JP2019081793A (ja) 2019-05-30
JP2014111632A (ja) 2014-06-19
WO2009143299A1 (en) 2009-11-26
RU2010151951A (ru) 2012-06-27
JP2015227384A (ja) 2015-12-17
JP2017186380A (ja) 2017-10-12
MX2010012647A (es) 2010-12-14
EP2285419A1 (en) 2011-02-23

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