KR20110002462A - 5-[3-(2,5-디클로로-4,6-디메틸-1-옥시-피리딘-3-일)-[1,2,4]옥사디아졸-5-일]-3-나이트로벤젠-1,2-디올의 결정형 - Google Patents
5-[3-(2,5-디클로로-4,6-디메틸-1-옥시-피리딘-3-일)-[1,2,4]옥사디아졸-5-일]-3-나이트로벤젠-1,2-디올의 결정형 Download PDFInfo
- Publication number
- KR20110002462A KR20110002462A KR1020107022717A KR20107022717A KR20110002462A KR 20110002462 A KR20110002462 A KR 20110002462A KR 1020107022717 A KR1020107022717 A KR 1020107022717A KR 20107022717 A KR20107022717 A KR 20107022717A KR 20110002462 A KR20110002462 A KR 20110002462A
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- South Korea
- Prior art keywords
- peaks
- crystalline
- ray powder
- powder diffraction
- pharmaceutical composition
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 41
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 56
- 239000013078 crystal Substances 0.000 claims description 29
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 23
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 21
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 21
- 230000001747 exhibiting effect Effects 0.000 claims description 20
- 238000002076 thermal analysis method Methods 0.000 claims description 15
- 238000001069 Raman spectroscopy Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 238000004458 analytical method Methods 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 10
- 238000003860 storage Methods 0.000 claims description 10
- 230000008859 change Effects 0.000 claims description 9
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- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 238000012986 modification Methods 0.000 claims description 4
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- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
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- 238000010998 test method Methods 0.000 claims description 3
- 238000012360 testing method Methods 0.000 claims description 3
- 208000027534 Emotional disease Diseases 0.000 claims description 2
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- ASOADIZOVZTJSR-UHFFFAOYSA-N opicapone Chemical compound CC1=C(Cl)C(C)=[N+]([O-])C(Cl)=C1C1=NOC(C=2C=C(C(O)=C(O)C=2)[N+]([O-])=O)=N1 ASOADIZOVZTJSR-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 102000006378 Catechol O-methyltransferase Human genes 0.000 description 8
- 108020002739 Catechol O-methyltransferase Proteins 0.000 description 8
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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- 229910052757 nitrogen Inorganic materials 0.000 description 4
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- YHKWFDPEASWKFQ-UHFFFAOYSA-N 3-nitrobenzene-1,2-diol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1O YHKWFDPEASWKFQ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000004164 analytical calibration Methods 0.000 description 2
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- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
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- 229910052751 metal Inorganic materials 0.000 description 2
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- 239000012925 reference material Substances 0.000 description 2
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- 230000001225 therapeutic effect Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PFDUUKDQEHURQC-ZETCQYMHSA-N 3-O-methyldopa Chemical compound COC1=CC(C[C@H](N)C(O)=O)=CC=C1O PFDUUKDQEHURQC-ZETCQYMHSA-N 0.000 description 1
- 102100027473 Cartilage oligomeric matrix protein Human genes 0.000 description 1
- 101710176668 Cartilage oligomeric matrix protein Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000005004 MAS NMR spectroscopy Methods 0.000 description 1
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- 208000005793 Restless legs syndrome Diseases 0.000 description 1
- 229920002472 Starch Chemical class 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003543 catechol methyltransferase inhibitor Substances 0.000 description 1
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- 238000005119 centrifugation Methods 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
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- 238000005388 cross polarization Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
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- 201000010099 disease Diseases 0.000 description 1
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- 229960003638 dopamine Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
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- 238000010828 elution Methods 0.000 description 1
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- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
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- 239000006082 mold release agent Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 1
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
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- 238000002411 thermogravimetry Methods 0.000 description 1
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Classifications
-
- 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
Landscapes
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6972108P | 2008-03-17 | 2008-03-17 | |
| US61/069,721 | 2008-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20110002462A true KR20110002462A (ko) | 2011-01-07 |
Family
ID=40585552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020107022717A Withdrawn KR20110002462A (ko) | 2008-03-17 | 2009-03-16 | 5-[3-(2,5-디클로로-4,6-디메틸-1-옥시-피리딘-3-일)-[1,2,4]옥사디아졸-5-일]-3-나이트로벤젠-1,2-디올의 결정형 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US8975410B2 (OSRAM) |
| EP (1) | EP2276758B1 (OSRAM) |
| JP (2) | JP2011514380A (OSRAM) |
| KR (1) | KR20110002462A (OSRAM) |
| CN (1) | CN102015696A (OSRAM) |
| AR (1) | AR070907A1 (OSRAM) |
| AU (1) | AU2009226221A1 (OSRAM) |
| BR (1) | BRPI0908731A2 (OSRAM) |
| CA (1) | CA2718772C (OSRAM) |
| CL (1) | CL2009000628A1 (OSRAM) |
| ES (1) | ES2565080T3 (OSRAM) |
| IL (1) | IL207854A0 (OSRAM) |
| MX (1) | MX2010009610A (OSRAM) |
| RU (1) | RU2010139315A (OSRAM) |
| TW (1) | TW200942531A (OSRAM) |
| WO (1) | WO2009116882A1 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9848134B2 (en) | 2010-04-23 | 2017-12-19 | Flir Systems, Inc. | Infrared imager with integrated metal layers |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0613859B8 (pt) | 2005-07-26 | 2021-05-25 | Bial Portela & Ca Sa | inibidores da comt, seus usos, e composição farmacêutica |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| SI2481410T1 (sl) | 2007-01-31 | 2017-01-31 | Bial - Portela & Ca., S.A. | Derivati nitrokatehola kot COMT inhibitorji, ki se dajejo s specifičnim dozirnim režimom |
| TW200942531A (en) * | 2008-03-17 | 2009-10-16 | Bial Portela & Companhia S A | Crystal forms of a nitrocatechol |
| AR072846A1 (es) * | 2008-07-29 | 2010-09-22 | Bial Portela & Ca Sa | RÉGIMEN DE ADMINISTRACIoN DE NITROCATECOLES PARA LA PREVENCIoN O TRATAMIENTO DE TRASTORNOS ASOCIADOS AL SISTEMA NERVIOSO CENTRAL. |
| US20100256194A1 (en) * | 2009-04-01 | 2010-10-07 | Bial - Portela & Ca, S.A. | Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making the same |
| 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 |
| EP2791134B1 (en) * | 2011-12-13 | 2019-09-25 | BIAL - Portela & Cª S.A. | Chemical compound useful as intermediate for preparing a catechol-o-methyltransferase inhibitor |
| JP2018500300A (ja) | 2014-11-28 | 2018-01-11 | ノヴィファーマ，エス．アー． | パーキンソン病を遅延させるための医薬 |
| PT3298008T (pt) * | 2015-05-20 | 2020-02-03 | Idorsia Pharmaceuticals Ltd | Forma cristalina do composto (s)-3-{4-[5-(2-ciclopentil-6- metoxi-piridin-4-il)-[1,2,4]oxadiazol-3-il]-2-etil-6-metilfenoxi}- 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 |
| BR112022017401A2 (pt) | 2020-03-13 | 2022-10-18 | Bial Portela & Ca Sa | Opicapona micronizada |
| 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 |
| GB202219669D0 (en) | 2022-12-23 | 2023-02-08 | Bial Portela & Ca Sa | Processes and intermediates for synthesising opicapone |
| AU2023449890A1 (en) | 2023-05-25 | 2025-11-27 | Bial-Portela & Ca., S.A. | Treatment regimens for early idiopathic parkinson's disease |
Family Cites Families (76)
| 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 |
| 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 |
| 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 |
| ATE113202T1 (de) | 1990-11-29 | 1994-11-15 | Wei Ming Pharmaceutical Mfg Co | Hilfsträger für direkte verpressung. |
| EP0619814A1 (en) | 1991-12-31 | 1994-10-19 | Fujisawa Pharmaceutical Co., Ltd. | 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 |
| US6660753B2 (en) | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| CA2381975A1 (en) | 1999-08-19 | 2001-02-22 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| AU2930501A (en) * | 2000-01-07 | 2001-07-24 | 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 |
| 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 |
| US20040097555A1 (en) | 2000-12-26 | 2004-05-20 | Shinegori Ohkawa | Concomitant drugs |
| WO2002051442A1 (en) | 2000-12-26 | 2002-07-04 | Takeda Chemical Industries, Ltd. | Concomitant drugs |
| CA2438991C (en) | 2001-02-21 | 2010-08-17 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| AU2002310187A1 (en) | 2001-05-30 | 2002-12-09 | Lg Biomedical Institute | Inhibitors of protein kinase for the treatment of disease |
| AU2002313633B2 (en) | 2001-06-08 | 2007-03-01 | Cytovia, Inc. | Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs |
| US6627646B2 (en) * | 2001-07-17 | 2003-09-30 | Sepracor Inc. | Norastemizole polymorphs |
| HUP0402092A3 (en) | 2001-07-26 | 2010-06-28 | Merck Patent Gmbh | Use of 2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]-chromane and its physiologically acceptable salts for preparation of pharmaceutical compositions |
| 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 |
| 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 |
| DE602005020611D1 (de) | 2004-04-28 | 2010-05-27 | Vertex Pharma | Als inhibitoren von rock und anderen proteinkinasen geeignete zusammensetzungen |
| GB0510143D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds A1 |
| JP2008519811A (ja) | 2004-11-10 | 2008-06-12 | オリオン コーポレーション | 下肢静止不能症候群の治療 |
| 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 |
| KR20080000622A (ko) | 2005-04-26 | 2008-01-02 | 뉴로서치 에이/에스 | 신규한 옥사디아졸 유도체 및 이의 의학적 용도 |
| 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 |
| BRPI0613859B8 (pt) | 2005-07-26 | 2021-05-25 | Bial Portela & Ca Sa | inibidores da comt, seus usos, e composição farmacêutica |
| 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 |
| WO2007061862A2 (en) | 2005-11-18 | 2007-05-31 | Janssen Pharmaceutica N.V. | 2-keto-oxazoles as modulators of fatty acid amide hydrolase |
| JP4738419B2 (ja) | 2005-11-30 | 2011-08-03 | 富士フイルムＲｉファーマ株式会社 | 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 |
| 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 |
| 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 |
| JP2008162955A (ja) | 2006-12-28 | 2008-07-17 | Chugai Pharmaceut Co Ltd | バリン含有高密度顆粒剤 |
| SI2481410T1 (sl) | 2007-01-31 | 2017-01-31 | Bial - Portela & Ca., S.A. | Derivati nitrokatehola kot COMT inhibitorji, ki se dajejo s specifičnim dozirnim režimom |
| PE20081891A1 (es) | 2007-03-22 | 2008-12-27 | Opko Health Inc | 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 |
| JP5718053B2 (ja) | 2007-08-27 | 2015-05-13 | ヘリコン・セラピューティクス・インコーポレーテッド | 治療用イソオキサゾール化合物 |
| KR20100126452A (ko) * | 2008-02-28 | 2010-12-01 | 바이알 - 포르텔라 앤드 씨에이 에스에이 | 난용성 약물용 약학적 조성물 |
| TW200942531A (en) | 2008-03-17 | 2009-10-16 | Bial Portela & Companhia S A | Crystal forms of a nitrocatechol |
| AR072846A1 (es) | 2008-07-29 | 2010-09-22 | Bial Portela & Ca Sa | RÉGIMEN DE ADMINISTRACIoN DE NITROCATECOLES PARA LA PREVENCIoN O TRATAMIENTO DE TRASTORNOS ASOCIADOS AL SISTEMA NERVIOSO CENTRAL. |
| 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 |
| RU2701731C2 (ru) | 2009-04-01 | 2019-10-01 | Биал-Портела Энд Ка, С.А. | Фармацевтические препараты, содержащие производные нитрокатехина, и способы их получения |
| US20100256194A1 (en) | 2009-04-01 | 2010-10-07 | Bial - Portela & Ca, S.A. | Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making the same |
| CN102781424B (zh) | 2010-03-04 | 2016-03-30 | 奥赖恩公司 | 左旋多巴、卡比多巴和恩他卡朋用于治疗帕金森病的应用 |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| EP2791134B1 (en) | 2011-12-13 | 2019-09-25 | BIAL - Portela & Cª S.A. | Chemical compound useful as intermediate for preparing a catechol-o-methyltransferase inhibitor |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9848134B2 (en) | 2010-04-23 | 2017-12-19 | Flir Systems, Inc. | Infrared imager with integrated metal layers |
Also Published As
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| EP2276758A1 (en) | 2011-01-26 |
| JP2011514380A (ja) | 2011-05-06 |
| US20150166519A1 (en) | 2015-06-18 |
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| US8975410B2 (en) | 2015-03-10 |
| RU2010139315A (ru) | 2012-04-27 |
| CA2718772A1 (en) | 2009-09-24 |
| WO2009116882A1 (en) | 2009-09-24 |
| MX2010009610A (es) | 2010-09-30 |
| AU2009226221A1 (en) | 2009-09-24 |
| JP2015044837A (ja) | 2015-03-12 |
| ES2565080T3 (es) | 2016-03-31 |
| CL2009000628A1 (es) | 2010-04-09 |
| AR070907A1 (es) | 2010-05-12 |
| CA2718772C (en) | 2017-05-02 |
| CN102015696A (zh) | 2011-04-13 |
| BRPI0908731A2 (pt) | 2017-05-16 |
| TW200942531A (en) | 2009-10-16 |
| EP2276758B1 (en) | 2016-01-06 |
| US9845316B2 (en) | 2017-12-19 |
| US20110112301A1 (en) | 2011-05-12 |
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