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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CA3088684A
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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)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurosurgery (AREA)
  • Veterinary Medicine (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicinal Preparation (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (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
GB1121413.7 2011-12-13
GBGB1121413.7A GB201121413D0 (en) 2011-12-13 2011-12-13 Chemical compounds and processes
US61/570,141 2011-12-13
US201261593625P 2012-02-01 2012-02-01
US61/593,625 2012-02-01
GB1201758.8 2012-02-01
GBGB1201758.8A GB201201758D0 (en) 2012-02-01 2012-02-01 Chemical compounds and processes
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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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
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

Family Applications After (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 (enExample)
EP (2) EP2791134B1 (enExample)
JP (3) JP6456143B2 (enExample)
BR (1) BR112014014341A2 (enExample)
CA (2) CA3088684C (enExample)
CY (1) CY1122580T1 (enExample)
DK (1) DK2791134T3 (enExample)
ES (2) ES2758659T3 (enExample)
HR (1) HRP20192133T8 (enExample)
HU (1) HUE047856T2 (enExample)
PL (1) PL2791134T3 (enExample)
PT (2) PT2791134T (enExample)
RS (1) RS59666B1 (enExample)
SI (1) SI2791134T1 (enExample)
WO (1) WO2013089573A1 (enExample)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007013830A1 (en) 2005-07-26 2007-02-01 Portela & Ca. S.A. Nitrocatechol derivatives as comt inhibitors
EP1845097A1 (en) 2006-04-10 2007-10-17 Portela & Ca., S.A. Oxadiazole derivatives as COMT inhibitors
DK2481410T3 (en) 2007-01-31 2016-10-24 Bial - Portela & Ca S A Nitrocatecholderivater as COMT inhibitors administered in a specific dosage regimen
BRPI0908731A2 (pt) 2008-03-17 2017-05-16 Bial - Portela & C A S A formas cristalinas de 5-[3-(2,5-dicloro-4,6-dimetil-1-óxi-piridina-3-il)[1,2,4]oxadiazol-5-il]-3-nitrobenzeno-1,2-diol
CN102448444B (zh) 2009-04-01 2016-05-25 巴尔-波特拉及康邦亚股份有限公司 包括硝基儿茶酚衍生物的药物制剂及其制备方法
US20140045900A1 (en) 2011-02-11 2014-02-13 Bial-Portela & Ca, S.A. Administration regime for nitrocatechols
US9126988B2 (en) 2011-12-13 2015-09-08 Bial—Portela & Ca, S.A. Intermediate for preparing a catechol-O-methyltransferase inhibitor
WO2016083863A1 (en) 2014-11-28 2016-06-02 Bial - Portela & Ca, S.A. Medicaments for slowing parkinson's disease
GB2563858A (en) * 2017-06-27 2019-01-02 Azad Pharmaceutical Ingredients Ag New route of synthesis for opicapone
EP3728241A4 (en) * 2017-12-18 2021-02-24 Unichem Laboratories Ltd PROCESS FOR THE MANUFACTURING OF OPICAPON AND INTERMEDIATE PRODUCTS THEREOF
WO2020072884A1 (en) 2018-10-05 2020-04-09 Neurocrine Biosciences, Inc. Methods for the administration of comt inhibitors
EP3860603A1 (en) 2018-10-05 2021-08-11 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
JP2023517690A (ja) * 2020-03-13 2023-04-26 ビアル－ポルテラ エ コンパニア，ソシエダッド アノニマ 微粉化オピカポン
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
WO2022131944A1 (en) 2020-12-17 2022-06-23 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
CN121487727A (zh) 2023-05-25 2026-02-06 巴尔-波特拉及康邦亚股份有限公司 用于早期特发性帕金森病的治疗方案
EP4727649A1 (en) 2023-06-19 2026-04-22 Medichem, S.A. Process for preparing opicapone
JP2026524539A (ja) 2023-07-11 2026-07-22 テイ・セラピューティクス・リミテッド Ｐｔｃリードスルー剤としてのナフチリジン又はピリドピリミジン核を含む化合物
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

Family Cites Families (72)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1532178A (en) 1921-07-25 1925-04-07 Louis A Godbold Lubricator
FR1260080A (fr) 1960-03-22 1961-05-05 Materiel De Forage Soc De Fab Trépan à molettes étanche
IL31990A (en) 1968-04-26 1974-05-16 Chinoin Gyogyszer Es Vegyeszet Pyridyl 1,2,4-oxadiazole derivatives,process for the preparation thereof and pharmaceutical compositions containing same
US4022901A (en) 1975-03-05 1977-05-10 E. R. Squibb & Sons, Inc. 3-Pyridinyl-5-isothiocyanophenyl oxadiazoles
US4264573A (en) 1979-05-21 1981-04-28 Rowell Laboratories, Inc. Pharmaceutical formulation for slow release via controlled surface erosion
US4386668A (en) 1980-09-19 1983-06-07 Hughes Tool Company Sealed lubricated and air cooled rock bit bearing
US5236952A (en) 1986-03-11 1993-08-17 Hoffmann-La Roche Inc. Catechol derivatives
DK175069B1 (da) 1986-03-11 2004-05-24 Hoffmann La Roche Pyrocatecholderivater
YU213587A (en) 1986-11-28 1989-06-30 Orion Yhtymae Oy Process for obtaining new pharmacologic active cateholic derivatives
DE3840954A1 (de) 1988-12-05 1990-06-07 Shell Int Research Herstellung von 2-chlornicotinsaeureestern
EP0462639A1 (en) 1990-06-05 1991-12-27 Shell Internationale Researchmaatschappij B.V. Preparation of 2-chloropyridine derivatives
DE69013689T2 (de) 1990-11-29 1995-03-02 Wei Ming Pharmaceutical Mfg Co Hilfsträger für direkte Verpressung.
CA2126976A1 (en) 1991-12-31 1993-07-08 Hisashi Takasugi Oxadiazole derivatives having acetylcholinesterase-inhibitory and muscarinic agonist activity
FR2730322B1 (fr) 1995-02-02 1997-04-30 Imago Monture de lunettes metallique
DE19628617A1 (de) 1996-07-16 1998-01-22 Basf Ag Direkttablettierhilfsmittel
US6206110B1 (en) 1996-09-09 2001-03-27 Smith International, Inc. Protected lubricant reservoir with pressure control for sealed bearing earth boring drill bit
AU762245B2 (en) 1998-09-18 2003-06-19 Vertex Pharmaceuticals Incorporated Inhibitors of p38
GB2344819A (en) 1998-12-18 2000-06-21 Portela & Ca Sa 2-Phenyl-1-(3,4-dihydroxy-5-nitrophenyl)-1-ethanones
FI109453B (fi) 1999-06-30 2002-08-15 Orion Yhtymae Oyj Farmaseuttinen koostumus
ATE307129T1 (de) 1999-08-19 2005-11-15 Nps Pharma Inc Heteropolycyclische verbindungen und ihre verwendung als antagonisten von metabotropen glutamatrezeptoren
US6660753B2 (en) 1999-08-19 2003-12-09 Nps Pharmaceuticals, Inc. Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
FI20000635A0 (fi) 2000-03-17 2000-03-17 Orion Yhtymae Oyj COMT-inhibiittoreiden käyttö analgeettina
SE0001438D0 (sv) 2000-04-18 2000-04-18 Axon Chemicals Bv New chemical compounds and their use in therapy
DE10029201A1 (de) 2000-06-19 2001-12-20 Basf Ag Verfahren zur Herstellung fester oraler Darreichungsformen mit retardierender Wirkstoffreisetzung
GB2363792A (en) 2000-06-21 2002-01-09 Portela & Ca Sa Nitrocatechols
CN1166626C (zh) 2000-08-30 2004-09-15 李凌松 三或四取代苯基化合物、其制备方法及应用
WO2002044209A2 (en) 2000-11-28 2002-06-06 Zymogenetics, Inc. Cytonkine receptor zcytor19
WO2002051442A1 (en) 2000-12-26 2002-07-04 Takeda Chemical Industries, Ltd. Concomitant drugs
US20040097555A1 (en) 2000-12-26 2004-05-20 Shinegori Ohkawa Concomitant drugs
PL369598A1 (en) 2001-02-21 2005-05-02 Nps Pharmaceuticals, Inc. Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
US20030208067A1 (en) 2001-05-30 2003-11-06 Cao Sheldon Xiaodong Inhibitors of protein kinase for the treatment of disease
US7041685B2 (en) 2001-06-08 2006-05-09 Cytovia, Inc. Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof
ATE352302T1 (de) 2001-07-26 2007-02-15 Merck Patent Gmbh Verwendung von 2- 5-(4-fluorphenyl)-3- pyridylmethylaminomethyl-chroman und seiner physiologisch annehmbaren salze
JP4379853B2 (ja) 2001-10-05 2009-12-09 惠民製藥股▲分▼有限公司 直接錠剤化用調合物および補助剤の調合方法
JP2006516250A (ja) 2002-12-18 2006-06-29 サイトビア インコーポレイティッド カスパーゼ活性化剤およびアポトーシス誘導物質としての３，５−二置換−［１，２，４］−オキサジアゾールおよびそれらの誘導体ならびにそれらの使用
WO2005006945A2 (en) 2003-07-03 2005-01-27 The Salk Institute For Biological Studies Methods for treating neural disorders and compounds useful therefor
ATE455546T1 (de) 2003-08-06 2010-02-15 Vertex Pharma Aminotriazol-verbindungen als proteinkinase- hemmer
DE10338174A1 (de) 2003-08-20 2005-03-24 Lts Lohmann Therapie-Systeme Ag Transdermale Arzneimittelzubereitungen mit Wirkstoffkombinationen zur Behandlung der Parkinson-Krankheit
US7300406B2 (en) 2003-09-30 2007-11-27 Carter Vandette B Medical examination apparatus
GB0325956D0 (en) 2003-11-06 2003-12-10 Addex Pharmaceuticals Sa Novel compounds
EP1751133B1 (en) 2004-04-28 2010-04-14 Vertex Pharmaceuticals Incorporated Compositions useful as inhibitors of rock and other protein kinases
GB0510143D0 (en) 2005-05-18 2005-06-22 Addex Pharmaceuticals Sa Novel compounds A1
US20060173074A1 (en) 2004-11-10 2006-08-03 Juha Ellmen Treatment of restless legs syndrome
EP1827453A1 (en) 2004-12-06 2007-09-05 Themis Laboratories Private Limited Sulfonylurea compositions and a process for its preparation
EP1833804A1 (en) 2004-12-28 2007-09-19 AstraZeneca AB Aryl sulphonamide modulators
US20080051441A1 (en) 2004-12-28 2008-02-28 Astrazeneca Ab Aryl Sulphonamide Modulators
CA2606087A1 (en) 2005-04-26 2006-11-02 Neurosearch A/S Novel oxadiazole derivatives and their medical use
US20060257473A1 (en) 2005-05-11 2006-11-16 Porranee Puranajoti Extended release tablet
GB0510139D0 (en) 2005-05-18 2005-06-22 Addex Pharmaceuticals Sa Novel compounds B1
ES2371774T3 (es) 2005-06-03 2012-01-10 Abbott Laboratories Derivados de ciclobutilamina.
JP2007024970A (ja) 2005-07-12 2007-02-01 Miyakawa:Kk 液晶表示装置の開口効率を上昇させるための樹脂レンズ製造法及びその製造装置
US20090000437A1 (en) 2005-07-14 2009-01-01 Provo Craft And Novelty, Inc. Methods for Cutting
WO2007013830A1 (en) * 2005-07-26 2007-02-01 Portela & Ca. S.A. Nitrocatechol derivatives as comt inhibitors
FR2889525A1 (fr) 2005-08-04 2007-02-09 Palumed Sa Nouveaux derives de polyquinoleines et leur utilisation therapeutique.
US20070048384A1 (en) 2005-08-26 2007-03-01 Joerg Rosenberg Pharmaceutical compositions
US20090111778A1 (en) 2005-11-18 2009-04-30 Richard Apodaca 2-Keto-Oxazoles as Modulators of Fatty Acid Amide Hydrolase
US8022075B2 (en) 2005-11-30 2011-09-20 Fujifilm Ri Pharma Co., Ltd. Diagnostic and remedy for disease caused by amyloid aggregation and/or deposition
GB0606774D0 (en) 2006-04-03 2006-05-10 Novartis Ag Organic compounds
EP1845097A1 (en) 2006-04-10 2007-10-17 Portela & Ca., S.A. Oxadiazole derivatives as COMT inhibitors
PE20080906A1 (es) 2006-08-17 2008-07-05 Kemia Inc Derivados heteroarilo como inhibidores de citocina
US20080167286A1 (en) 2006-12-12 2008-07-10 Abbott Laboratories Pharmaceutical compositions and their methods of use
US8486979B2 (en) 2006-12-12 2013-07-16 Abbvie Inc. 1,2,4 oxadiazole compounds and methods of use thereof
DK2481410T3 (en) * 2007-01-31 2016-10-24 Bial - Portela & Ca S A Nitrocatecholderivater as COMT inhibitors administered in a specific dosage regimen
US8222243B2 (en) 2007-08-27 2012-07-17 Dart Neuroscience (Cayman) Ltd Therapeutic isoxazole compounds
EP2259777A2 (en) 2008-02-28 2010-12-15 BIAL - Portela & Ca., S.A. Pharmaceutical composition for poorly soluble drugs
BRPI0908731A2 (pt) * 2008-03-17 2017-05-16 Bial - Portela & C A S A formas cristalinas de 5-[3-(2,5-dicloro-4,6-dimetil-1-óxi-piridina-3-il)[1,2,4]oxadiazol-5-il]-3-nitrobenzeno-1,2-diol
BRPI0913913A2 (pt) 2008-07-29 2015-10-13 Bial Portela & Ca Sa regime de dosagem para nitrocatecóis
CN102448444B (zh) 2009-04-01 2016-05-25 巴尔-波特拉及康邦亚股份有限公司 包括硝基儿茶酚衍生物的药物制剂及其制备方法
PT2413913T (pt) 2009-04-01 2022-06-09 Bial Portela & Ca Sa Formulações farmacêuticas que compreendem derivados de nitrocatecol e métodos para os preparar
JP5774610B2 (ja) 2010-03-04 2015-09-09 オリオン コーポレーション パーキンソン病の治療方法
US20140045900A1 (en) 2011-02-11 2014-02-13 Bial-Portela & Ca, S.A. Administration regime for nitrocatechols
US9126988B2 (en) * 2011-12-13 2015-09-08 Bial—Portela & Ca, S.A. Intermediate for preparing a catechol-O-methyltransferase inhibitor

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