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)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Emergency Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Toxicology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (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 (https=)
EP (1) EP2285419A4 (https=)
JP (6) JP5701750B2 (https=)
KR (1) KR101717145B1 (https=)
CN (1) CN102149412A (https=)
AU (1) AU2009249071A1 (https=)
BR (1) BRPI0912820A2 (https=)
CA (2) CA2724788C (https=)
IL (1) IL209384A0 (https=)
MX (1) MX2010012647A (https=)
RU (1) RU2010151951A (https=)
WO (1) WO2009143299A1 (https=)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101717145B1 (ko) 2008-05-20 2017-03-16 노이로제스엑스, 인코포레이티드 간보호제 아세트아미노펜 공통 프로드러그
RU2010151953A (ru) 2008-05-20 2012-06-27 Ньюроджесэкс, Инк. (Us) Карбонатные продукты и способы их применения
KR101698028B1 (ko) 2008-05-20 2017-01-26 노이로제스엑스, 인코포레이티드 수용성 아세트아미노펜 유사체
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
CA3042642A1 (en) 2013-08-12 2015-02-19 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
CA2955229C (en) 2014-07-17 2020-03-10 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
WO2016064873A1 (en) 2014-10-20 2016-04-28 Pharmaceutical Manufacturing Research Services, Inc. Extended release abuse deterrent liquid fill dosage form
US11389409B2 (en) * 2019-08-30 2022-07-19 Remedy Diagnostics LLC Transdermal device comprising acetaminophen prodrug

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Also Published As

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

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