CA3088684C - Compound 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitrobenzene-1,2-diol in microparticulate form and its use in the treatment of parkinson's disease - Google Patents

Compound 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitrobenzene-1,2-diol in microparticulate form and its use in the treatment of parkinson's disease Download PDF

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Publication number
CA3088684C
CA3088684C CA3088684A CA3088684A CA3088684C CA 3088684 C CA3088684 C CA 3088684C CA 3088684 A CA3088684 A CA 3088684A CA 3088684 A CA3088684 A CA 3088684A CA 3088684 C CA3088684 C CA 3088684C
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compound
formula
product
acid
circle diameter
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English (en)
French (fr)
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CA3088684A1 (en
Inventor
Domenico Russo
Laszlo Erno Kiss
Jorge Bruno Reis Wahnon
David Alexander Learmonth
Tibor Eszenyi
Axel Zimmerman
Bjoern Schlummer
Michael Kreis
Klaus Reiter
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Bial Portela and Cia SA
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Bial Portela and Cia SA
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Priority claimed from GBGB1121413.7A external-priority patent/GB201121413D0/en
Priority claimed from GBGB1201758.8A external-priority patent/GB201201758D0/en
Application filed by Bial Portela and Cia SA filed Critical Bial Portela and Cia SA
Publication of CA3088684A1 publication Critical patent/CA3088684A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurology (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)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Neurosurgery (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicinal Preparation (AREA)
CA3088684A 2011-12-13 2012-12-12 Compound 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitrobenzene-1,2-diol in microparticulate form and its use in the treatment of parkinson's disease Active CA3088684C (en)

Applications Claiming Priority (11)

Application Number Priority Date Filing Date Title
US201161570141P 2011-12-13 2011-12-13
US61/570,141 2011-12-13
GBGB1121413.7A GB201121413D0 (en) 2011-12-13 2011-12-13 Chemical compounds and processes
GB1121413.7 2011-12-13
US201261593625P 2012-02-01 2012-02-01
GBGB1201758.8A GB201201758D0 (en) 2012-02-01 2012-02-01 Chemical compounds and processes
GB1201758.8 2012-02-01
US61/593,625 2012-02-01
US201261718589P 2012-10-25 2012-10-25
US61/718,589 2012-10-25
CA2858025A CA2858025C (en) 2011-12-13 2012-12-12 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-2-hydroxy-3-methoxy-1-nitrobenzene as an intermediate to prepare a catechol-o-methyltransferase inhibitor

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2858025A Division CA2858025C (en) 2011-12-13 2012-12-12 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-2-hydroxy-3-methoxy-1-nitrobenzene as an intermediate to prepare a catechol-o-methyltransferase inhibitor

Publications (2)

Publication Number Publication Date
CA3088684A1 CA3088684A1 (en) 2013-06-20
CA3088684C true CA3088684C (en) 2021-10-26

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Family Applications (2)

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CA2858025A Active CA2858025C (en) 2011-12-13 2012-12-12 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-2-hydroxy-3-methoxy-1-nitrobenzene as an intermediate to prepare a catechol-o-methyltransferase inhibitor
CA3088684A Active CA3088684C (en) 2011-12-13 2012-12-12 Compound 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitrobenzene-1,2-diol in microparticulate form and its use in the treatment of parkinson's disease

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CA2858025A Active CA2858025C (en) 2011-12-13 2012-12-12 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-2-hydroxy-3-methoxy-1-nitrobenzene as an intermediate to prepare a catechol-o-methyltransferase inhibitor

Country Status (15)

Country Link
US (2) US9126988B2 (OSRAM)
EP (2) EP3604299B1 (OSRAM)
JP (3) JP6456143B2 (OSRAM)
BR (1) BR112014014341A2 (OSRAM)
CA (2) CA2858025C (OSRAM)
CY (1) CY1122580T1 (OSRAM)
DK (1) DK2791134T3 (OSRAM)
ES (2) ES2960805T3 (OSRAM)
HR (1) HRP20192133T8 (OSRAM)
HU (1) HUE047856T2 (OSRAM)
PL (1) PL2791134T3 (OSRAM)
PT (2) PT3604299T (OSRAM)
RS (1) RS59666B1 (OSRAM)
SI (1) SI2791134T1 (OSRAM)
WO (1) WO2013089573A1 (OSRAM)

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RU2010139315A (ru) 2008-03-17 2012-04-27 Биал - Портела Энд Ка., С.А. (Pt) Кристаллические формы 5-[3-(2,5-дихлор-4,6-диметил-1-окси-пиридин-3-ил)[1,2,4]оксадиазол-5-ил]-3-нитробензол-1,2-диола
RU2701731C2 (ru) 2009-04-01 2019-10-01 Биал-Портела Энд Ка, С.А. Фармацевтические препараты, содержащие производные нитрокатехина, и способы их получения
US20140045900A1 (en) 2011-02-11 2014-02-13 Bial-Portela & Ca, S.A. Administration regime for nitrocatechols
EP3604299B1 (en) * 2011-12-13 2023-07-26 Bial-Portela & CA, S.A. Chemical compound useful as intermediate for preparing a catechol-0-methyl transferase inhibitor
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WO2020072886A1 (en) 2018-10-05 2020-04-09 Neurocrine Biosciences, Inc. Methods for the administration of comt inhibitors
CA3112994A1 (en) 2018-10-05 2020-04-09 Neurocrine Biosciences, Inc. Methods for the administration of comt inhibitors
CN109529881A (zh) * 2018-11-12 2019-03-29 刘晓菊 一种治疗帕金森药物用中间体5-硝基香草酸的制备方法
CA3174918A1 (en) 2020-03-13 2021-09-16 Bial - Portela & Ca, S.A. Micronised opicapone
TW202200138A (zh) * 2020-05-26 2022-01-01 日商小野藥品工業股份有限公司 包含奧匹卡朋（ｏｐｉｃａｐｏｎｅ）之錠劑
GB202011709D0 (en) 2020-07-28 2020-09-09 Bial Portela & Ca Sa Solid dispersion of opicapone
GB202016425D0 (en) 2020-10-16 2020-12-02 Bial Portela & Ca Sa Treatment regimens for parkinson's disease
EP4262798A1 (en) 2020-12-17 2023-10-25 Bial-Portela & CA, S.A. Treatment regimens for early idiopathic parkinson's disease
CN112375014A (zh) * 2020-12-17 2021-02-19 重庆柳江医药科技有限公司 一种奥匹卡朋工艺杂质及制备方法和用途
US20240300930A1 (en) * 2021-02-26 2024-09-12 Msn Laboratories Private Limited, R&D Center Novel process for the preparation of 2,5-dichloro-3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-4,6-dimethylpyridine-1-oxide
CN113292489B (zh) * 2021-06-16 2022-08-30 泓博智源(开原)药业有限公司 二氯代二烷基烟腈的制备方法
GB202204798D0 (en) 2022-04-01 2022-05-18 Bial Portela & Ca Sa Prodrugs of opicapone
GB202212082D0 (en) 2022-08-18 2022-10-05 Bial Portela & Ca Sa Treatment regimens for parkinson's disease
GB202219669D0 (en) 2022-12-23 2023-02-08 Bial Portela & Ca Sa Processes and intermediates for synthesising opicapone
WO2024242579A1 (en) 2023-05-25 2024-11-28 Bial-Portela & Ca., S.A. Treatment regimens for early idiopathic parkinson's disease
WO2024260874A1 (en) * 2023-06-19 2024-12-26 Medichem, S.A. Process for preparing opicapone
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CN119775271A (zh) * 2024-12-31 2025-04-08 南京海纳医药科技股份有限公司 一种奥吡卡朋粗品的精制方法
CN120081837A (zh) * 2025-02-14 2025-06-03 江苏天士力帝益药业有限公司 一种低单杂高纯度的奥匹卡朋中间体05的制备方法

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Publication number Publication date
US9126988B2 (en) 2015-09-08
EP3604299A1 (en) 2020-02-05
CA2858025C (en) 2020-09-22
CA3088684A1 (en) 2013-06-20
HRP20192133T8 (hr) 2021-02-19
ES2758659T3 (es) 2020-05-06
US20140350057A1 (en) 2014-11-27
CY1122580T1 (el) 2021-01-27
JP2018052949A (ja) 2018-04-05
JP6456143B2 (ja) 2019-01-23
PL2791134T3 (pl) 2020-03-31
EP2791134A1 (en) 2014-10-22
US20160009700A1 (en) 2016-01-14
US9630955B2 (en) 2017-04-25
JP6721558B2 (ja) 2020-07-15
BR112014014341A2 (pt) 2017-08-22
SI2791134T1 (sl) 2020-01-31
EP2791134B1 (en) 2019-09-25
HUE047856T2 (hu) 2020-05-28
RS59666B1 (sr) 2020-01-31
CA2858025A1 (en) 2013-06-20
HRP20192133T1 (hr) 2020-02-21
ES2960805T3 (es) 2024-03-06
PT3604299T (pt) 2023-10-31
WO2013089573A1 (en) 2013-06-20
JP2015500335A (ja) 2015-01-05
JP2020059729A (ja) 2020-04-16
PT2791134T (pt) 2019-12-18
EP3604299B1 (en) 2023-07-26
DK2791134T3 (da) 2019-12-09

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