CA2718772C - Crystal forms of 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridine-3-yl)[1,2,4]oxadiazol-5-yl]-3-nit robenzene-1,2-diol - Google Patents

Crystal forms of 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridine-3-yl)[1,2,4]oxadiazol-5-yl]-3-nit robenzene-1,2-diol Download PDF

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CA2718772C
CA2718772C CA2718772A CA2718772A CA2718772C CA 2718772 C CA2718772 C CA 2718772C CA 2718772 A CA2718772 A CA 2718772A CA 2718772 A CA2718772 A CA 2718772A CA 2718772 C CA2718772 C CA 2718772C
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polymorph
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pharmaceutical composition
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French (fr)
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CA2718772A1 (en
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David Alexander Learmonth
Keith Lorimer
Kevin Wayne Meyer
Tibor Eszenyi
Almosne Kovach
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Bial Portela and Cia SA
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Bial Portela and Cia SA
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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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/10—Antioedematous agents; Diuretics
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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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)
  • Medicinal Chemistry (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)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Psychology (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2718772A 2008-03-17 2009-03-16 Crystal forms of 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridine-3-yl)[1,2,4]oxadiazol-5-yl]-3-nit robenzene-1,2-diol Active CA2718772C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US6972108P 2008-03-17 2008-03-17
US61/069,721 2008-03-17
PCT/PT2009/000013 WO2009116882A1 (en) 2008-03-17 2009-03-16 Crystal forms of 5- [3- (2, 5-dichloro-4, 6-dimethyl-1-oxy-pyridine-3-yl) [1,2,3] oxadiazol-5-yl] -3-nit robenzene-1, 2-diol

Publications (2)

Publication Number Publication Date
CA2718772A1 CA2718772A1 (en) 2009-09-24
CA2718772C true CA2718772C (en) 2017-05-02

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CA2718772A Active CA2718772C (en) 2008-03-17 2009-03-16 Crystal forms of 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridine-3-yl)[1,2,4]oxadiazol-5-yl]-3-nit robenzene-1,2-diol

Country Status (16)

Country Link
US (2) US8975410B2 (enExample)
EP (1) EP2276758B1 (enExample)
JP (2) JP2011514380A (enExample)
KR (1) KR20110002462A (enExample)
CN (1) CN102015696A (enExample)
AR (1) AR070907A1 (enExample)
AU (1) AU2009226221A1 (enExample)
BR (1) BRPI0908731A2 (enExample)
CA (1) CA2718772C (enExample)
CL (1) CL2009000628A1 (enExample)
ES (1) ES2565080T3 (enExample)
IL (1) IL207854A0 (enExample)
MX (1) MX2010009610A (enExample)
RU (1) RU2010139315A (enExample)
TW (1) TW200942531A (enExample)
WO (1) WO2009116882A1 (enExample)

Families Citing this family (19)

* 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
BRPI0913913A2 (pt) * 2008-07-29 2015-10-13 Bial Portela & Ca Sa regime de dosagem para nitrocatecóis
PT2413913T (pt) * 2009-04-01 2022-06-09 Bial Portela & Ca Sa Formulações farmacêuticas que compreendem derivados de nitrocatecol e métodos para os preparar
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
US9848134B2 (en) 2010-04-23 2017-12-19 Flir Systems, Inc. Infrared imager with integrated metal layers
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
ES2770348T3 (es) * 2015-05-20 2020-07-01 Idorsia Pharmaceuticals Ltd Forma cristalina del compuesto (s)-3-{4-[5-(2-ciclopentil-6-metoxi-piridin-4-il)-[1,2,4]oxadiazol-3-il]-2-etil-6-metil-fenoxi}-propano-1,2-diol
RU2659987C2 (ru) * 2016-12-07 2018-07-04 Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) Планарный твердофазный оптический сенсор для определения белковых соединений методом спектроскопии гигантского комбинационного рассеяния и его применение для детектирования белковых соединений
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
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
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

Family Cites Families (76)

* 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
DK175069B1 (da) 1986-03-11 2004-05-24 Hoffmann La Roche Pyrocatecholderivater
US5236952A (en) 1986-03-11 1993-08-17 Hoffmann-La Roche Inc. Catechol derivatives
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
IL131037A (en) 1999-07-22 2004-06-20 Israel Atomic Energy Comm Method for making threedimensional photonic band-gap crystals
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
IL150524A0 (en) * 2000-01-07 2003-02-12 Transform Pharmaceuticals Inc High-throughput formation, identification, and analysis of diverse solid-forms
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
US6966488B2 (en) 2000-08-24 2005-11-22 Sagawa Express Co., Ltd. Card payment method for service charge concerning to physical distribution or transportation
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
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
US6627646B2 (en) * 2001-07-17 2003-09-30 Sepracor Inc. Norastemizole polymorphs
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
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.
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
JP2008162955A (ja) 2006-12-28 2008-07-17 Chugai Pharmaceut Co Ltd バリン含有高密度顆粒剤
DK2481410T3 (en) 2007-01-31 2016-10-24 Bial - Portela & Ca S A Nitrocatecholderivater as COMT inhibitors administered in a specific dosage regimen
AR065802A1 (es) 2007-03-22 2009-07-01 Schering Corp Formulaciones de comprimidos que contienen sales de 8- [( 1- ( 3,5- bis- (trifluorometil) fenil) -etoxi ) - metil) -8- fenil -1, 7- diaza- spiro [ 4,5] decan -2- ona y comprimidos elaborados a partir de estas
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
US8827197B2 (en) 2008-11-04 2014-09-09 Microgreen Polymers Inc Apparatus and method for interleaving polymeric roll for gas impregnation and solid-state foam processing
PT2413913T (pt) 2009-04-01 2022-06-09 Bial Portela & Ca Sa Formulações farmacêuticas que compreendem derivados de nitrocatecol e métodos para os preparar
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
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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Publication number Publication date
MX2010009610A (es) 2010-09-30
TW200942531A (en) 2009-10-16
JP2015044837A (ja) 2015-03-12
RU2010139315A (ru) 2012-04-27
CA2718772A1 (en) 2009-09-24
IL207854A0 (en) 2010-12-30
ES2565080T3 (es) 2016-03-31
US20150166519A1 (en) 2015-06-18
WO2009116882A1 (en) 2009-09-24
US9845316B2 (en) 2017-12-19
AU2009226221A1 (en) 2009-09-24
CL2009000628A1 (es) 2010-04-09
US8975410B2 (en) 2015-03-10
AR070907A1 (es) 2010-05-12
KR20110002462A (ko) 2011-01-07
US20110112301A1 (en) 2011-05-12
CN102015696A (zh) 2011-04-13
JP2011514380A (ja) 2011-05-06
EP2276758A1 (en) 2011-01-26
EP2276758B1 (en) 2016-01-06
BRPI0908731A2 (pt) 2017-05-16

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