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
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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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- 230000008707 rearrangement Effects 0.000 claims description 3
- 238000010998 test method Methods 0.000 claims description 3
- 238000012360 testing method Methods 0.000 claims description 3
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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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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 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
- 230000005540 biological transmission Effects 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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- 239000012925 reference material Substances 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 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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- 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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- 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
- 230000001419 dependent effect Effects 0.000 description 1
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- 201000010099 disease Diseases 0.000 description 1
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- 239000006185 dispersion Substances 0.000 description 1
- 229960003638 dopamine 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)
- 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 | |
| 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 (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 (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 |
|---|---|---|---|---|
| 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 |
| 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 |
| RU2017120184A (ru) | 2014-11-28 | 2018-12-28 | БИАЛ - ПОРТЕЛА ЭНД Ка, С.А. | Лекарства для замедления течения болезни паркинсона |
| EP3298008B1 (en) * | 2015-05-20 | 2019-11-20 | Idorsia Pharmaceuticals Ltd | Crystalline form of the compound (s)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol |
| RU2659987C2 (ru) * | 2016-12-07 | 2018-07-04 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) | Планарный твердофазный оптический сенсор для определения белковых соединений методом спектроскопии гигантского комбинационного рассеяния и его применение для детектирования белковых соединений |
| JP2023517690A (ja) * | 2020-03-13 | 2023-04-26 | ビアル－ポルテラ エ コンパニア，ソシエダッド アノニマ | 微粉化オピカポン |
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| 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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|---|---|
| JP2011514380A (ja) | 2011-05-06 |
| 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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