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 PDFInfo
- Publication number
- 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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- pharmaceutical composition
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- 239000013078 crystal Substances 0.000 title description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 21
- 230000008569 process Effects 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 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 23
- 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 23
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 17
- 239000000843 powder Substances 0.000 claims description 12
- 238000001757 thermogravimetry curve Methods 0.000 claims description 12
- 238000001237 Raman spectrum Methods 0.000 claims description 11
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 8
- 208000018737 Parkinson disease Diseases 0.000 claims description 7
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 208000027232 peripheral nervous system disease Diseases 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 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 claims 3
- 102100038238 Aromatic-L-amino-acid decarboxylase Human genes 0.000 claims 2
- 101710151768 Aromatic-L-amino-acid decarboxylase Proteins 0.000 claims 2
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- 239000008186 active pharmaceutical agent Substances 0.000 abstract description 7
- 238000000634 powder X-ray diffraction Methods 0.000 description 35
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- 229960004502 levodopa Drugs 0.000 description 21
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- 229910002483 Cu Ka Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000004090 dissolution Methods 0.000 description 8
- 238000005079 FT-Raman Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000010899 nucleation Methods 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
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- 102000006378 Catechol O-methyltransferase Human genes 0.000 description 5
- 108020002739 Catechol O-methyltransferase Proteins 0.000 description 5
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- 230000009471 action Effects 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229920001778 nylon Polymers 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
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- 239000000126 substance Substances 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-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
- 230000005540 biological transmission Effects 0.000 description 2
- 239000003543 catechol methyltransferase inhibitor Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 238000007416 differential thermogravimetric analysis Methods 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 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
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
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- 238000007069 methylation reaction Methods 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YHKWFDPEASWKFQ-UHFFFAOYSA-N 3-nitrobenzene-1,2-diol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1O YHKWFDPEASWKFQ-UHFFFAOYSA-N 0.000 description 1
- 229910016523 CuKa Inorganic materials 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
- 229920000881 Modified starch Polymers 0.000 description 1
- 208000016285 Movement disease Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010030312 On and off phenomenon Diseases 0.000 description 1
- 208000005793 Restless legs syndrome Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000004308 accommodation Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004164 analytical calibration Methods 0.000 description 1
- 230000000181 anti-adherent effect Effects 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000005388 cross polarization Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 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
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 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
- 230000001771 impaired effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 230000008863 intramolecular interaction Effects 0.000 description 1
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- 239000000155 melt Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
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- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
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- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002636 symptomatic treatment 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Anesthesiology (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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 |
Family
ID=40585552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1907382E (pt) | 2005-07-26 | 2015-09-25 | Bial Portela & Ca Sa | Derivados de nitrocatecol como inibidores de comt |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| CA2678391C (en) | 2007-01-31 | 2017-01-17 | David Alexander Learmonth | Dosage regimen for comt inhibitors |
| CL2009000628A1 (es) | 2008-03-17 | 2010-04-09 | Bial Portela & Companhia S A | Forma cristalina de 5-[3-(2,5-dicloro-4,6-dimetil-1-oxi-piridin-3-il)-[1,2,4]oxadiazol-5-il]-3-nitrobenceno-1,2-diol, composicion farmaceutica que la comprende, proceso para obtenerla y su uso para tratar trastornos del animo, enfermedad de parkinson y trastornos parkinsonianos, alteraciones gastrointestinales, entre otros. |
| EP2307020B1 (en) * | 2008-07-29 | 2019-02-20 | Bial-Portela & CA, S.A. | Administration regime for nitrocatechols |
| CN102438595B (zh) * | 2009-04-01 | 2016-04-27 | 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 |
| RU2701731C2 (ru) | 2009-04-01 | 2019-10-01 | Биал-Портела Энд Ка, С.А. | Фармацевтические препараты, содержащие производные нитрокатехина, и способы их получения |
| 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 |
| PL2791134T3 (pl) | 2011-12-13 | 2020-03-31 | BIAL - PORTELA & Cª S.A. | Związek chemiczny użyteczny jako związek pośredni do wytwarzania inhibitora katechol-o-metylotransferazy |
| 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 |
| DK3298008T3 (da) * | 2015-05-20 | 2020-02-10 | Idorsia Pharmaceuticals Ltd | Krystallinsk form af forbindelsen (s)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propan-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 |
| AU2021235850A1 (en) | 2020-03-13 | 2022-10-06 | BIAL - PORTELA & Cª, S.A. | Micronised opicapone |
| 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 |
| KR20230118933A (ko) | 2020-12-17 | 2023-08-14 | 바이알 - 포르텔라 앤드 씨에이 에스에이 | 초기 특발성 파킨슨병에 대한 치료 요법 |
| GB202219669D0 (en) | 2022-12-23 | 2023-02-08 | Bial Portela & Ca Sa | Processes and intermediates for synthesising opicapone |
| WO2024242579A1 (en) | 2023-05-25 | 2024-11-28 | Bial-Portela & Ca., S.A. | Treatment regimens for early idiopathic parkinson's disease |
Family Cites Families (76)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102438595B (zh) | 2009-04-01 | 2016-04-27 | 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 |
| RU2701731C2 (ru) | 2009-04-01 | 2019-10-01 | Биал-Портела Энд Ка, С.А. | Фармацевтические препараты, содержащие производные нитрокатехина, и способы их получения |
| BR112012018256A8 (pt) | 2010-03-04 | 2017-12-19 | Orion Corp | método de tratamento de doença de parkinson |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| PL2791134T3 (pl) | 2011-12-13 | 2020-03-31 | BIAL - PORTELA & Cª S.A. | Związek chemiczny użyteczny jako związek pośredni do wytwarzania inhibitora katechol-o-metylotransferazy |
-
2009
- 2009-03-16 CL CL2009000628A patent/CL2009000628A1/es unknown
- 2009-03-16 ES ES09722681.5T patent/ES2565080T3/es active Active
- 2009-03-16 RU RU2010139315/04A patent/RU2010139315A/ru unknown
- 2009-03-16 EP EP09722681.5A patent/EP2276758B1/en active Active
- 2009-03-16 CN CN2009801099261A patent/CN102015696A/zh active Pending
- 2009-03-16 TW TW098108415A patent/TW200942531A/zh unknown
- 2009-03-16 MX MX2010009610A patent/MX2010009610A/es not_active Application Discontinuation
- 2009-03-16 US US12/933,044 patent/US8975410B2/en active Active
- 2009-03-16 WO PCT/PT2009/000013 patent/WO2009116882A1/en not_active Ceased
- 2009-03-16 KR KR1020107022717A patent/KR20110002462A/ko not_active Withdrawn
- 2009-03-16 JP JP2011500722A patent/JP2011514380A/ja active Pending
- 2009-03-16 BR BRPI0908731A patent/BRPI0908731A2/pt not_active IP Right Cessation
- 2009-03-16 CA CA2718772A patent/CA2718772C/en active Active
- 2009-03-16 AU AU2009226221A patent/AU2009226221A1/en not_active Abandoned
- 2009-03-16 AR ARP090100933A patent/AR070907A1/es unknown
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2010
- 2010-08-29 IL IL207854A patent/IL207854A0/en unknown
-
2014
- 2014-10-31 JP JP2014222625A patent/JP2015044837A/ja active Pending
-
2015
- 2015-02-23 US US14/628,630 patent/US9845316B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| RU2010139315A (ru) | 2012-04-27 |
| TW200942531A (en) | 2009-10-16 |
| IL207854A0 (en) | 2010-12-30 |
| AR070907A1 (es) | 2010-05-12 |
| EP2276758A1 (en) | 2011-01-26 |
| WO2009116882A1 (en) | 2009-09-24 |
| CL2009000628A1 (es) | 2010-04-09 |
| CN102015696A (zh) | 2011-04-13 |
| KR20110002462A (ko) | 2011-01-07 |
| US9845316B2 (en) | 2017-12-19 |
| US8975410B2 (en) | 2015-03-10 |
| US20150166519A1 (en) | 2015-06-18 |
| AU2009226221A1 (en) | 2009-09-24 |
| JP2011514380A (ja) | 2011-05-06 |
| ES2565080T3 (es) | 2016-03-31 |
| BRPI0908731A2 (pt) | 2017-05-16 |
| EP2276758B1 (en) | 2016-01-06 |
| US20110112301A1 (en) | 2011-05-12 |
| MX2010009610A (es) | 2010-09-30 |
| CA2718772A1 (en) | 2009-09-24 |
| JP2015044837A (ja) | 2015-03-12 |
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