JP2011514380A - 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 - Google Patents
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 Download PDFInfo
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- JP2011514380A JP2011514380A JP2011500722A JP2011500722A JP2011514380A JP 2011514380 A JP2011514380 A JP 2011514380A JP 2011500722 A JP2011500722 A JP 2011500722A JP 2011500722 A JP2011500722 A JP 2011500722A JP 2011514380 A JP2011514380 A JP 2011514380A
- Authority
- JP
- Japan
- Prior art keywords
- crystal modification
- further characterized
- polymorph
- following
- peaks
- 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.)
- Pending
Links
- 239000013078 crystal Substances 0.000 title claims description 44
- 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 title claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 45
- 239000008186 active pharmaceutical agent Substances 0.000 claims abstract description 8
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 50
- 230000004048 modification Effects 0.000 claims description 40
- 238000012986 modification Methods 0.000 claims description 40
- 230000009466 transformation Effects 0.000 claims description 24
- 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 22
- 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 22
- 239000007787 solid Substances 0.000 claims description 18
- 238000001757 thermogravimetry curve Methods 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 12
- 238000004458 analytical method Methods 0.000 claims description 11
- 238000003860 storage Methods 0.000 claims description 10
- 238000001237 Raman spectrum Methods 0.000 claims description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 7
- 230000001747 exhibiting effect Effects 0.000 claims description 7
- 238000001069 Raman spectroscopy Methods 0.000 claims description 6
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 238000010899 nucleation Methods 0.000 claims description 5
- 238000010998 test method Methods 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 239000002002 slurry Substances 0.000 claims description 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 208000019022 Mood disease Diseases 0.000 claims description 2
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- 208000027089 Parkinsonian disease Diseases 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 208000015114 central nervous system disease Diseases 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims description 2
- 208000027232 peripheral nervous system disease Diseases 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 4
- 102100038238 Aromatic-L-amino-acid decarboxylase Human genes 0.000 claims 1
- 101710151768 Aromatic-L-amino-acid decarboxylase Proteins 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 16
- 229960004502 levodopa Drugs 0.000 description 21
- 239000000203 mixture Substances 0.000 description 18
- 238000000844 transformation Methods 0.000 description 10
- 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
- 238000005079 FT-Raman Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 230000005855 radiation Effects 0.000 description 7
- 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 6
- 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
- 210000004556 brain Anatomy 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- 239000004677 Nylon Substances 0.000 description 5
- 230000009471 action Effects 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
- 239000000463 material Substances 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
- 230000008499 blood brain barrier function Effects 0.000 description 3
- 210000001218 blood-brain barrier Anatomy 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000003595 spectral effect Effects 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
- 238000005481 NMR spectroscopy Methods 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
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 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
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000013480 data collection Methods 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 235000019253 formic acid Nutrition 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
- 230000002503 metabolic effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 238000000386 microscopy Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-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
- 229910002483 Cu Ka Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- 206010030312 On and off phenomenon 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
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004164 analytical calibration Methods 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
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000011049 filling Methods 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
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000010438 heat treatment 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
- 238000001727 in vivo Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 230000008863 intramolecular interaction Effects 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000002360 preparation method Methods 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
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 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
- 208000011580 syndromic disease Diseases 0.000 description 1
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)
- 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 | |
| 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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014222625A Division JP2015044837A (ja) | 2008-03-17 | 2014-10-31 | 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011514380A true JP2011514380A (ja) | 2011-05-06 |
| JP2011514380A5 JP2011514380A5 (enExample) | 2012-05-10 |
Family
ID=40585552
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011500722A Pending JP2011514380A (ja) | 2008-03-17 | 2009-03-16 | 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 |
| JP2014222625A Pending JP2015044837A (ja) | 2008-03-17 | 2014-10-31 | 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 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014222625A Pending JP2015044837A (ja) | 2008-03-17 | 2014-10-31 | 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 |
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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015500335A (ja) * | 2011-12-13 | 2015-01-05 | 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 |
| 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 |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1907382T1 (sl) | 2005-07-26 | 2015-10-30 | Bial-Portela & Ca S.A., | Nitrokateholni derivati kot inhibitorji COMT |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| ES2597705T3 (es) | 2007-01-31 | 2017-01-20 | Bial - Portela & Ca., S.A. | Derivados de nitrocatecol como inhibidores de COMT administrados con un régimen de dosificación específico |
| EP2276758B1 (en) | 2008-03-17 | 2016-01-06 | 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-nit robenzene-1, 2-diol |
| PT2307020T (pt) * | 2008-07-29 | 2019-05-28 | Bial Portela & Ca Sa | Regime de administração de nitrocatecólicos |
| KR102329271B1 (ko) * | 2009-04-01 | 2021-11-22 | 바이알 - 포르텔라 앤드 씨에이 에스에이 | 니트로카테콜 유도체를 포함하는 제약 제제 및 그의 제조 방법 |
| AU2010231962B2 (en) * | 2009-04-01 | 2015-05-21 | Bial - Portela & Ca., S.A. | Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making the same |
| US9848134B2 (en) | 2010-04-23 | 2017-12-19 | Flir Systems, Inc. | Infrared imager with integrated metal layers |
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- 2009-03-16 ES ES09722681.5T patent/ES2565080T3/es active Active
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| JP2015500335A (ja) * | 2011-12-13 | 2015-01-05 | 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 |
| 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 |
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| KR20110002462A (ko) | 2011-01-07 |
| MX2010009610A (es) | 2010-09-30 |
| EP2276758B1 (en) | 2016-01-06 |
| IL207854A0 (en) | 2010-12-30 |
| EP2276758A1 (en) | 2011-01-26 |
| US9845316B2 (en) | 2017-12-19 |
| CA2718772A1 (en) | 2009-09-24 |
| CA2718772C (en) | 2017-05-02 |
| AU2009226221A1 (en) | 2009-09-24 |
| TW200942531A (en) | 2009-10-16 |
| AR070907A1 (es) | 2010-05-12 |
| BRPI0908731A2 (pt) | 2017-05-16 |
| RU2010139315A (ru) | 2012-04-27 |
| JP2015044837A (ja) | 2015-03-12 |
| CN102015696A (zh) | 2011-04-13 |
| ES2565080T3 (es) | 2016-03-31 |
| WO2009116882A1 (en) | 2009-09-24 |
| US20150166519A1 (en) | 2015-06-18 |
| US8975410B2 (en) | 2015-03-10 |
| US20110112301A1 (en) | 2011-05-12 |
| CL2009000628A1 (es) | 2010-04-09 |
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