WO2008094053A1 - Dosage regimen for comt inhibitors - Google Patents

Dosage regimen for comt inhibitors Download PDF

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Publication number
WO2008094053A1
WO2008094053A1 PCT/PT2007/000043 PT2007000043W WO2008094053A1 WO 2008094053 A1 WO2008094053 A1 WO 2008094053A1 PT 2007000043 W PT2007000043 W PT 2007000043W WO 2008094053 A1 WO2008094053 A1 WO 2008094053A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
term
day
dopa
compound
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.)
Ceased
Application number
PCT/PT2007/000043
Other languages
English (en)
French (fr)
Inventor
David Alexander Learmonth
Laszlo Erno Kiss
Pedro Nuno Leal Palma
Humberto Dos Santos Ferreira
Patrício Manuel Vieira Araújo Soares da SILVA
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.)
Bial Portela and Cia SA
Original Assignee
Bial Portela and Cia SA
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
Priority to EP07834911.5A priority Critical patent/EP2124947B1/en
Priority to CA2678391A priority patent/CA2678391C/en
Priority to ES07834911.5T priority patent/ES2644049T3/es
Priority to CN200780050737.2A priority patent/CN101631548B/zh
Priority to US12/524,848 priority patent/US8524746B2/en
Priority to DK07834911.5T priority patent/DK2124947T3/da
Priority to AU2007346018A priority patent/AU2007346018A1/en
Priority to JP2009548186A priority patent/JP5517629B2/ja
Priority to KR1020097016752A priority patent/KR101522157B1/ko
Priority to MX2009008051A priority patent/MX2009008051A/es
Priority to BRPI0721213-5A priority patent/BRPI0721213B1/pt
Priority to RU2009132188/04A priority patent/RU2518483C2/ru
Application filed by Bial Portela and Cia SA filed Critical Bial Portela and Cia SA
Priority to ARP080100382A priority patent/AR065098A1/es
Publication of WO2008094053A1 publication Critical patent/WO2008094053A1/en
Priority to IL200020A priority patent/IL200020A/en
Anticipated expiration legal-status Critical
Priority to NO20092905A priority patent/NO20092905L/no
Priority to US13/950,661 priority patent/US20130331416A1/en
Priority to US14/689,397 priority patent/US9745290B2/en
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • 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
    • 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
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • 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
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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

Definitions

  • the condensation and dehydration reaction is carried out in the presence of an organic or inorganic base.
  • Suitable preferred bases include triethylamine, tributylamine, 2,6-lutidine, N-methylmorpholine, pyridine, imidazole, N-methylimidazole and 4-dimethylaminopyridine.
  • Particularly preferred bases include pyridine, N-methylimidazole and 4-dimethylaminopyridine.
  • Rats fasted overnight were administered orally with tolcapone and compounds of general formula I (3 mg/kg) or vehicle (0.5% carboxymethylcellulose, 4 ml/kg).
  • rats were administered orally with L-DOPA (12 mg/kg) plus benserazide (3 mg/kg) or with vehicle (0.5% carboxymethylcellulose, 4 ml/kg).
  • L-DOPA 12 mg/kg
  • benserazide 3 mg/kg
  • vehicle 0.5% carboxymethylcellulose, 4 ml/kg
  • rats were anaesthetised with sodium pentobarbitone (60 mg/kg, i.p.), blood was collected through the vena cava and the whole brain was quickly removed. Brains were stored in perchloric acid 0.2 M for subsequent assay of L-DOPA, 3-O-methyl-L-DOPA, dopamine, DOPAC and HVA.
  • FIG. 1 Effect of compound A and tolcapone (3 mg/kg) on liver COMT activity at 0.5, 1, 3, 6, 9, 24 and 48 h after the administration of the COMT inhibitor. Symbols represent means ⁇ SEM of 5 experiments per group. Significantly different from corresponding controls values (* P ⁇ 0.05).
  • Suitable exemplary pharmaceutical formulations are prepared according to the following specifications:

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychology (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
PCT/PT2007/000043 2007-01-31 2007-10-10 Dosage regimen for comt inhibitors Ceased WO2008094053A1 (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
BRPI0721213-5A BRPI0721213B1 (pt) 2007-01-31 2007-10-10 Uso de nitrocatecóis substituídos, e embalagem
ES07834911.5T ES2644049T3 (es) 2007-01-31 2007-10-10 Régimen de dosificación para inhibidores de COMT
CN200780050737.2A CN101631548B (zh) 2007-01-31 2007-10-10 Comt抑制剂的单次药物剂量单元和药物组合物
US12/524,848 US8524746B2 (en) 2007-01-31 2007-10-10 Dosage regimen for COMT inhibitors
DK07834911.5T DK2124947T3 (da) 2007-01-31 2007-10-10 Doseringsskema for comt-inhibitorer
AU2007346018A AU2007346018A1 (en) 2007-01-31 2007-10-10 Dosage regimen for COMT inhibitors
JP2009548186A JP5517629B2 (ja) 2007-01-31 2007-10-10 Ｃｏｍｔ阻害剤用の投薬計画
KR1020097016752A KR101522157B1 (ko) 2007-01-31 2007-10-10 Ｃｏｍｔ 억제제의 투약 방법
MX2009008051A MX2009008051A (es) 2007-01-31 2007-10-10 Regimen posologico para inhibidores de comt.
EP07834911.5A EP2124947B1 (en) 2007-01-31 2007-10-10 Dosage regimen for comt inhibitors
CA2678391A CA2678391C (en) 2007-01-31 2007-10-10 Dosage regimen for comt inhibitors
RU2009132188/04A RU2518483C2 (ru) 2007-01-31 2007-10-10 Режим дозирования ингибиторов комт
ARP080100382A AR065098A1 (es) 2007-01-31 2008-01-30 Regimen posologico para inhibidores de comt
IL200020A IL200020A (en) 2007-01-31 2009-07-22 Dosing procedure for comt inhibitors
NO20092905A NO20092905L (no) 2007-01-31 2009-08-28 Doseringsregime for COMT-ihibitorer
US13/950,661 US20130331416A1 (en) 2007-01-31 2013-07-25 Dosage regimen for comt inhibitors
US14/689,397 US9745290B2 (en) 2007-01-31 2015-04-17 Dosage regimen for COMT inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07002091.2 2007-01-31
EP07002091 2007-01-31

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/524,848 A-371-Of-International US8524746B2 (en) 2007-01-31 2007-10-10 Dosage regimen for COMT inhibitors
US13/950,661 Continuation US20130331416A1 (en) 2007-01-31 2013-07-25 Dosage regimen for comt inhibitors

Publications (1)

Publication Number Publication Date
WO2008094053A1 true WO2008094053A1 (en) 2008-08-07

Family

ID=38961862

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/PT2007/000043 Ceased WO2008094053A1 (en) 2007-01-31 2007-10-10 Dosage regimen for comt inhibitors

Country Status (24)

Country Link
US (3) US8524746B2 (https=)
EP (2) EP2481410B1 (https=)
JP (1) JP5517629B2 (https=)
KR (1) KR101522157B1 (https=)
CN (1) CN101631548B (https=)
AR (2) AR065098A1 (https=)
AU (1) AU2007346018A1 (https=)
BR (1) BRPI0721213B1 (https=)
CA (1) CA2678391C (https=)
CY (1) CY1118311T1 (https=)
DK (2) DK2124947T3 (https=)
ES (2) ES2644049T3 (https=)
HR (1) HRP20161261T8 (https=)
HU (1) HUE031317T2 (https=)
IL (1) IL200020A (https=)
LT (1) LT2481410T (https=)
MX (1) MX2009008051A (https=)
NO (1) NO20092905L (https=)
PL (1) PL2481410T3 (https=)
PT (2) PT2481410T (https=)
RU (1) RU2518483C2 (https=)
SI (1) SI2481410T1 (https=)
WO (1) WO2008094053A1 (https=)
ZA (1) ZA200905940B (https=)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009116882A1 (en) * 2008-03-17 2009-09-24 Portela & Ca., S.A. 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
WO2010014025A1 (en) * 2008-07-29 2010-02-04 Bial - Portela & Ca., S.A. Administration regime for nitrocatechols
WO2010114404A1 (en) * 2009-04-01 2010-10-07 Bial - Portela & Ca., S.A. Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making thereof
US20100256194A1 (en) * 2009-04-01 2010-10-07 Bial - Portela & Ca, S.A. Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making the same
US7834039B2 (en) 2006-12-15 2010-11-16 Abbott Laboratories Oxadiazole compounds
WO2011069075A3 (en) * 2009-12-04 2011-07-28 Grant Jon E Treating impulse control disorders with catechol-o- methyl-transferase inhibitors
US8168793B2 (en) 2005-07-26 2012-05-01 Portela & Ca., S.A. Nitrocatechol derivatives as COMT inhibitors
WO2012107708A1 (en) * 2011-02-11 2012-08-16 Bial - Portela & Ca, S.A. Administration regime for nitrocatechols
WO2013089573A1 (en) * 2011-12-13 2013-06-20 BIAL - PORTELA & Cª., S.A. Chemical compound useful as intermediate for preparing a catechol-o-methyltransferase inhibitor
US8524746B2 (en) 2007-01-31 2013-09-03 Bial-Portela & Ca., S.A. Dosage regimen for COMT inhibitors
US8536203B2 (en) 2006-04-10 2013-09-17 Bial-Portela & Ca, S.A. Pharmaceutical compounds
US10357468B2 (en) 2014-11-28 2019-07-23 Bial—Portela & Ca, S.A. Medicaments for slowing Parkinson's disease
WO2020072884A1 (en) 2018-10-05 2020-04-09 Neurocrine Biosciences, Inc. Methods for the administration of comt inhibitors
WO2020072886A1 (en) 2018-10-05 2020-04-09 Neurocrine Biosciences, Inc. Methods for the administration of comt inhibitors
WO2023191648A1 (en) 2022-04-01 2023-10-05 Bial - Portela & Ca, S.A. Prodrugs of opicapone

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL169855A (en) * 2005-07-25 2014-05-28 Elta Systems Ltd A system and method for locating a receiver location
MX2010009043A (es) * 2008-02-28 2010-10-25 Bial Portela & Ca Sa Composicion farmaceutica para farmacos poco solubles.
WO2016123577A1 (en) * 2015-01-30 2016-08-04 Lieber Institute For Brain Development Comt inhibiting methods and compositions
JP6858712B2 (ja) 2015-01-30 2021-04-14 リーバー インスティテュート フォー ブレイン ディベロップメントＬｉｅｂｅｒ Ｉｎｓｔｉｔｕｔｅ Ｆｏｒ Ｂｒａｉｎ Ｄｅｖｅｌｏｐｍｅｎｔ Ｃｏｍｔ阻害方法及び組成物
EP3380471B8 (en) 2015-11-25 2022-01-19 Lieber Institute Inc. DBA Lieber Institute For Brain Development Tetrahydro-8h-pyrido[1,2-a]pyrazine-8-ones as comt inhibitors for the treatment of neurodegenerative disorders
CA3078652A1 (en) 2017-10-12 2019-04-18 Novo Nordisk A/S Semaglutide in medical therapy
USD912395S1 (en) * 2019-11-01 2021-03-09 Jondarius Brown Apparatus for storing earphones

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5476875A (en) 1986-03-11 1995-12-19 Hoffman-La Roche Inc. Catechol derivatives
WO2007013830A1 (en) 2005-07-26 2007-02-01 Portela & Ca. S.A. Nitrocatechol derivatives as comt inhibitors
WO2007117165A1 (en) 2006-04-10 2007-10-18 Bial - Portela & Ca, S.A. New pharmaceutical compounds

Family Cites Families (72)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US660753A (en) * 1899-11-27 1900-10-30 Ferdinand-Christoph Von Heydebrand Und Der Lasa Artificial fuel.
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
US3647809A (en) * 1968-04-26 1972-03-07 Chinoin Gyogyszer Es Vegyeszet Certain pyridyl-1 2 4-oxadiazole derivatives
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
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
US5206372A (en) 1990-06-05 1993-04-27 Shell Research Limited Preparation of 2-chloropyridine derivatives
ES2066092T3 (es) 1990-11-29 1995-03-01 Wei Ming Pharmaceutical Mfg Co Coadyuvante para la formacion directa de comprimidos.
EP0619814A1 (en) 1991-12-31 1994-10-19 Fujisawa Pharmaceutical Co., Ltd. Oxadiazole derivatives having acetylcholinesterase-inhibitory and muscarinic agonist activity
GB9419274D0 (en) * 1994-09-23 1994-11-09 Orion Yhtymae Oy New method for the preparation of 3,4-dihydroxy-5-nitrobenzaldehyde
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
JP2002526482A (ja) * 1998-09-18 2002-08-20 バーテックス ファーマシューティカルズ インコーポレイテッド ｐ３８のインヒビター
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
KR100875222B1 (ko) 1999-08-19 2008-12-19 아스트라제네카 아베 헤테로폴리사이클릭 화합물 및 간접 글루타메이트 수용체길항제로서의 그들의 용도
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
EP1329825A4 (en) 2000-08-24 2006-03-22 Sagawa Express Co Ltd CARD PAYMENT PROCEDURE FOR SERVICE FEES RELATING TO PHYSICAL DISTRIBUTION OR TRANSPORT
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
JP2004532611A (ja) 2000-11-28 2004-10-28 ザイモジェネティクス，インコーポレイティド サイトカイン受容体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
MXPA03007513A (es) 2001-02-21 2004-07-30 Nps Pharma Inc Compuestos heteropoliciclicos y su uso como antagonistas del receptor metabotropico de glutamato.
WO2002096867A2 (en) 2001-05-30 2002-12-05 Lg Biomedical Institute Inhibitors of protein kinase for the treatment of disease
JP2005504014A (ja) 2001-06-08 2005-02-10 サイトビア インコーポレイテッド カスパーゼの活性化因子およびアポトーシスの誘導因子としての置換された３−アリール−５−アリール−［１，２，４］−オキサジアゾール類および類似体、並びにその使用法
PT1408964E (pt) 2001-07-26 2007-05-31 Merck Patent Gmbh Utilização de 2-5-(4-fluorofenil) -3-piridilmetilaminometil-cromano e de seus sais fisiologicamente aceitáveis.
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
CN100364531C (zh) * 2002-12-18 2008-01-30 西托维亚公司 3,5－二取代－[1,2,4]－二唑及类似物和其用途
WO2005006945A2 (en) * 2003-07-03 2005-01-27 The Salk Institute For Biological Studies Methods for treating neural disorders and compounds useful therefor
WO2005013982A1 (en) 2003-08-06 2005-02-17 Vertex Pharmaceuticals Incorporated Aminotriazole compounds useful as inhibitors of protein kinases
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
WO2005105780A2 (en) 2004-04-28 2005-11-10 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
WO2006061697A1 (en) 2004-12-06 2006-06-15 Themis Laboratories Private Limited Sulfonylurea compositions and a process for its preparation
US20080051441A1 (en) * 2004-12-28 2008-02-28 Astrazeneca Ab Aryl Sulphonamide Modulators
WO2006071184A1 (en) 2004-12-28 2006-07-06 Astrazeneca Ab Aryl sulphonamide modulators
US8017631B2 (en) 2005-04-26 2011-09-13 Neurosearch A/S 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
US7553964B2 (en) * 2005-06-03 2009-06-30 Abbott Laboratories Cyclobutyl amine derivatives
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
GB0515327D0 (en) * 2005-07-26 2005-08-31 Portela & Ca Sa 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
EP1954137A4 (en) * 2005-11-18 2008-12-17 Janssen Pharmaceutica Nv 2-KETO-OXAZOLE AS MODULATORS OF FATTY ACID AMIDHYDROLASE
WO2007063946A1 (ja) * 2005-11-30 2007-06-07 Fujifilm Ri Pharma Co., Ltd. アミロイドの凝集及び／又は沈着に起因する疾患の診断薬及び治療薬
GB0606774D0 (en) 2006-04-03 2006-05-10 Novartis Ag Organic compounds
PE20080906A1 (es) 2006-08-17 2008-07-05 Kemia Inc Derivados heteroarilo como inhibidores de citocina
US8486979B2 (en) * 2006-12-12 2013-07-16 Abbvie Inc. 1,2,4 oxadiazole compounds and methods of use thereof
US20080167286A1 (en) * 2006-12-12 2008-07-10 Abbott Laboratories Pharmaceutical compositions and their methods of use
BRPI0721213B1 (pt) 2007-01-31 2021-11-09 Bial - Portela & Ca, S.A. Uso de nitrocatecóis substituídos, e embalagem
KR101669432B1 (ko) 2007-08-27 2016-10-26 다트 뉴로사이언스 (케이만) 엘티디. 치료적 이속사졸 화합물
MX2010009043A (es) * 2008-02-28 2010-10-25 Bial Portela & Ca Sa Composicion farmaceutica para farmacos poco solubles.
WO2009116882A1 (en) 2008-03-17 2009-09-24 Portela & Ca., S.A. 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
ES2723729T3 (es) 2008-07-29 2019-08-30 Bial Portela & Ca Sa Régimen de administración de nitrocatecoles
PT2413912T (pt) 2009-04-01 2019-06-11 Bial Portela & Ca Sa Formulações farmacêuticas compreendendo derivados de nitrocatecol e métodos para as produzir
BRPI1016132B8 (pt) 2009-04-01 2021-05-25 Bial Portela & Ca Sa composição, formulação farmacêutica, processo de obtenção de uma formulação farmacêutica estável
EA026419B1 (ru) 2010-03-04 2017-04-28 Орион Корпорейшн Применение леводопы, карбидопы и энтакапона для лечения болезни паркинсона
US20140045900A1 (en) 2011-02-11 2014-02-13 Bial-Portela & Ca, S.A. Administration regime for nitrocatechols
JP6456143B2 (ja) 2011-12-13 2019-01-23 ノヴィファーマ，エス．アー． カテコール−ｏ−メチル転移酵素阻害剤を調製するための中間体として有用な化学的化合物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5476875A (en) 1986-03-11 1995-12-19 Hoffman-La Roche Inc. Catechol derivatives
WO2007013830A1 (en) 2005-07-26 2007-02-01 Portela & Ca. S.A. Nitrocatechol derivatives as comt inhibitors
WO2007117165A1 (en) 2006-04-10 2007-10-18 Bial - Portela & Ca, S.A. New pharmaceutical compounds

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PARASHOS, S.A. ET AL., CLIN. NEUROPHARMACOL., vol. 27, no. 3, 2004, pages 119 - 123
SMITH, K.S. ET AL., CHEM. RES. TOXICOL., vol. 16, 2003, pages 123 - 128

Cited By (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9550759B2 (en) 2005-07-26 2017-01-24 Bial—Portela & Ca, S.A. Nitrocatechol derivatives as COMT inhibitors
US8907099B2 (en) 2005-07-26 2014-12-09 Bial-Portela & Ca, S.A. Nitrocatechol derivatives as COMT inhibitors
US10336740B2 (en) 2005-07-26 2019-07-02 Bial—Portela & Ca, S.A. Nitrocatechol derivatives as COMT inhibitors
US8168793B2 (en) 2005-07-26 2012-05-01 Portela & Ca., S.A. Nitrocatechol derivatives as COMT inhibitors
US9446012B2 (en) 2006-04-10 2016-09-20 Bial—Portela & Ca, S.A. Pharmaceutical compounds
US8536203B2 (en) 2006-04-10 2013-09-17 Bial-Portela & Ca, S.A. Pharmaceutical compounds
US7834039B2 (en) 2006-12-15 2010-11-16 Abbott Laboratories Oxadiazole compounds
US9745290B2 (en) 2007-01-31 2017-08-29 Bial—Portela & Ca, S.A. Dosage regimen for COMT inhibitors
US8524746B2 (en) 2007-01-31 2013-09-03 Bial-Portela & Ca., S.A. Dosage regimen for COMT inhibitors
JP2011514380A (ja) * 2008-03-17 2011-05-06 バイアル−ポルテラ アンド シーエー，エス．エー． ５−［３−（２，５−ジクロロ−４，６−ジメチル−１−オキシ−ピリジン−３−イル）［１，２，４］オキサジアゾール−５−イル］−３−ニトロベンゼン−１，２−ジオールの結晶形
US9845316B2 (en) 2008-03-17 2017-12-19 BIAL—Portela & CA., S.A. Crystal forms of 5-[3-(2,5-dichloro-4, 6-dimethyl-1-oxy-pyridine-3-yl)[1,2,4]oxadiazol-5-yl]-3-nitrobenzene-1,2-diol
WO2009116882A1 (en) * 2008-03-17 2009-09-24 Portela & Ca., S.A. 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
JP2015044837A (ja) * 2008-03-17 2015-03-12 ノヴィファーマ，エス．アー． ５−［３−（２，５−ジクロロ−４，６−ジメチル−１−オキシ−ピリジン−３−イル）［１，２，４］オキサジアゾール−５−イル］−３−ニトロベンゼン−１，２−ジオールの結晶形
US8975410B2 (en) 2008-03-17 2015-03-10 BIAL—Portela & CA., S.A. Crystal forms of 5-[3-(2,5-dichloro-4, 6-dimethyl-1-oxy-pyridine-3-yl)[1,2,4] oxadiazol-5-yl]-3-nitrobenzene-1,2-diol
AU2009277196B2 (en) * 2008-07-29 2015-06-18 Bial - Portela & Ca., S.A. Administration regime for nitrocatechols
WO2010014025A1 (en) * 2008-07-29 2010-02-04 Bial - Portela & Ca., S.A. Administration regime for nitrocatechols
JP2015232030A (ja) * 2009-04-01 2015-12-24 ノヴィファーマ ソシエテ アノニム ニトロカテコール誘導体を含む医薬製剤及びその製造方法
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WO2011069075A3 (en) * 2009-12-04 2011-07-28 Grant Jon E Treating impulse control disorders with catechol-o- methyl-transferase inhibitors
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AU2011358842B2 (en) * 2011-02-11 2017-02-02 Bial - Portela & Ca, S.A. Administration regime for nitrocatechols
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US12129247B2 (en) * 2011-02-11 2024-10-29 Bial-Portela & Ca, S.A. Administration regime for nitrocatechols
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US9126988B2 (en) 2011-12-13 2015-09-08 Bial—Portela & Ca, S.A. Intermediate for preparing a catechol-O-methyltransferase inhibitor
WO2013089573A1 (en) * 2011-12-13 2013-06-20 BIAL - PORTELA & Cª., S.A. Chemical compound useful as intermediate for preparing a catechol-o-methyltransferase inhibitor
US9630955B2 (en) 2011-12-13 2017-04-25 BIAL—Portela & Cª., S.A Chemical compound useful as intermediate for preparing a catechol-O-methyltransferase inhibitor
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US10357468B2 (en) 2014-11-28 2019-07-23 Bial—Portela & Ca, S.A. Medicaments for slowing Parkinson's disease
WO2020072886A1 (en) 2018-10-05 2020-04-09 Neurocrine Biosciences, Inc. Methods for the administration of comt inhibitors
WO2020072884A1 (en) 2018-10-05 2020-04-09 Neurocrine Biosciences, Inc. Methods for the administration of comt inhibitors
WO2023191648A1 (en) 2022-04-01 2023-10-05 Bial - Portela & Ca, S.A. Prodrugs of opicapone

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