ES2566482T3 - Derivados de oxazol sustituidos, composición farmacéutica que contiene los derivados, y método para tratar la enfermedad de Parkinson utilizando los mismos - Google Patents
Derivados de oxazol sustituidos, composición farmacéutica que contiene los derivados, y método para tratar la enfermedad de Parkinson utilizando los mismos Download PDFInfo
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- ES2566482T3 ES2566482T3 ES10746439.8T ES10746439T ES2566482T3 ES 2566482 T3 ES2566482 T3 ES 2566482T3 ES 10746439 T ES10746439 T ES 10746439T ES 2566482 T3 ES2566482 T3 ES 2566482T3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
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- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- 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
- C07D413/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Un derivado de azol sustituido representado por la siguiente Fórmula (I) o sales farmacéuticamente aceptables del mismo: **Fórmula** en donde, R se selecciona del grupo que consiste de C7-C15 arilalquilo no sustituido o sustituido por al menos uno seleccionado del grupo que consiste de halógeno, trifluorometilo, trifluoroalcoxi, -NO2, C(>=O)OCH3, C1-C6 alquilo lineal o ramificado, C1-C6 alcoxi, fenilo, feniloxi, benciloxi, -C(>=O)H, -OH y -CH>=N-OH; C4-C15 heteroarilalquilo no sustituido o sustituido por al menos uno seleccionado del grupo que consiste de halógeno, C(>=O)OCH3, C1-C6 alquilo lineal o ramificado, C1-C6 alcoxi, fenilo, feniloxi y benciloxi; C1-C10 alquilo lineal, ramificado o cíclico sustituido por al menos uno seleccionado del grupo que consiste de C1-C3alquiloxi, C1-C3alquiltio, carbamato, (-OC(>=O)NH2), tert-butil- OC(>=O)NH-, -NH3+, -NH2, -OH, -C(>=O)OCH2CH3, NHC(>=O)NH2, trifluorometilsufanilo, trifluorometilo, y -CN, Y se selecciona del grupo que consiste de O y -N-R1; R1 se selecciona del grupo que consiste de H y C1-C3 alquilo lineal o ramificado; R2 se selecciona del grupo que consiste de H y halógeno; A se selecciona del grupo que consiste de O y S; B se selecciona del grupo que consiste de C y N; Z se selecciona del grupo que consiste de imidazol, pirrolidina, y tetrazol sustituido o no sustituido por al menos un sustituyente seleccionado del grupo que consiste de OH, carbamato, C1-C4 alquilo lineal o ramificado, halógeno, - NO2, -NH2,-CF3, -CN y fenilo; -OC(>=O)NR3R4; NR5R6; NHC(>=NH)NH2, y -NHC(>=O)NH2; cada uno de R3 y R4 se selecciona independientemente del grupo que consiste de H; C1-C5 alquilo no sustituido o sustituido por al menos uno seleccionado del grupo que consiste de NH2, y NR7R8; piperidina, piperazina, y diazepam no sustituido o sustituido por C1-C3 alquilo; oR3 y R4 juntos pueden formar piperidina, piperazina, imidazol, pirrolidina, triazol, tetrazol, diazepam o morfolina no sustituido o sustituido por C1-C3 alquilo; cada uno de R5 y R6 es independientemente seleccionado del grupo que consiste de C2-C3 alqueno; C2-C3 alquino; y C1-C4 alquilo lineal o ramificado sustituido por al menos uno seleccionado del grupo que consiste de -OH, -C(O)NH2, C1-C3 alcoxi, y carbamato; cada uno de R7 y R8 es al menos uno seleccionado del grupo que consiste de H y C1-C3 alquilo lineal o ramificado, cada uno de m y n es independientemente 0 o 1.
Description
Claims (1)
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imagen1 imagen2 imagen3 imagen4
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20090015856 | 2009-02-25 | ||
| KR20090015856 | 2009-02-25 | ||
| KR1020100016686A KR101220182B1 (ko) | 2009-02-25 | 2010-02-24 | 치환된 아졸 유도체 화합물, 이를 포함하는 약제학적 조성물 및 이를 이용한 파킨슨씨 병 치료방법 |
| KR20100016686 | 2010-02-24 | ||
| PCT/KR2010/001186 WO2010098600A2 (en) | 2009-02-25 | 2010-02-25 | Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating parkinson's disease using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2566482T3 true ES2566482T3 (es) | 2016-04-13 |
Family
ID=43004459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10746439.8T Active ES2566482T3 (es) | 2009-02-25 | 2010-02-25 | Derivados de oxazol sustituidos, composición farmacéutica que contiene los derivados, y método para tratar la enfermedad de Parkinson utilizando los mismos |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8828992B2 (es) |
| EP (1) | EP2401263B1 (es) |
| JP (1) | JP5717031B2 (es) |
| KR (1) | KR101220182B1 (es) |
| CN (1) | CN102333764B (es) |
| AU (1) | AU2010218584B2 (es) |
| BR (1) | BRPI1008727B8 (es) |
| CA (1) | CA2751343C (es) |
| ES (1) | ES2566482T3 (es) |
| MX (1) | MX2011008910A (es) |
| PL (1) | PL2401263T3 (es) |
| RU (1) | RU2578596C2 (es) |
| WO (1) | WO2010098600A2 (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101799429B1 (ko) * | 2010-05-03 | 2017-11-21 | 에스케이바이오팜 주식회사 | 신경 세포 사멸 또는 신경 퇴화를 억제하기 위한 약학적 조성물 |
| EP2817304A4 (en) * | 2011-07-14 | 2015-01-21 | Biochromix Newco Ab | Novel compounds and their use in therapy |
| US9505728B2 (en) | 2012-03-09 | 2016-11-29 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| KR102191562B1 (ko) | 2012-11-07 | 2020-12-15 | 에스케이바이오팜 주식회사 | 난용성 약물의 고체분산체 및 이의 제조방법 |
| EP2935228B9 (en) | 2012-12-20 | 2017-12-06 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| BR112015022202A2 (pt) | 2013-03-14 | 2017-07-18 | Dart Neuroscience Cayman Ltd | compostos substituídos de naftiridina e quinolina como inibidores da mao |
| PE20160880A1 (es) | 2013-09-06 | 2016-09-22 | Inception 2 Inc | Compuestos de triazolona y usos de los mismos |
| WO2016097004A1 (en) * | 2014-12-17 | 2016-06-23 | King's College London | BICYCLOHETEROARYL-HETEROARYL-BENZOIC ACID COMPOUNDS AS RETINOIC ACID RECEPTOR BETA (RARβ) AGONISTS |
| KR101896398B1 (ko) * | 2017-11-14 | 2018-09-07 | 에스케이바이오팜 주식회사 | 신경 세포 사멸 또는 신경 퇴화를 억제하기 위한 약학적 조성물 |
| CN108676001A (zh) * | 2018-06-12 | 2018-10-19 | 江西师范大学 | 一种3-取代-5-异噁唑基-4-取代-1-1,2,3-三氮唑基甲烷化合物 |
| US11517548B2 (en) * | 2018-07-19 | 2022-12-06 | Impel Pharmaceuticals Inc. | Respiratory tract delivery of levodopa and DOPA decarboxylase inhibitor for treatment of Parkinson's Disease |
| KR20200109537A (ko) | 2019-03-13 | 2020-09-23 | 충북대학교 산학협력단 | 1-(4-클로로-3-(트리플루오로메틸)페닐)-3-(4-((5-(트리플루오로메틸)피리딘-2-일)옥시)사이클로헥실)유레아를 유효성분으로 하는 파킨슨 질환 예방 또는 치료용 약학적 조성물 |
| KR102186761B1 (ko) * | 2020-06-03 | 2020-12-04 | 옙바이오 주식회사 | 2-(4-(1-하이드록시프로판-2-일)페닐)이소인돌린-1-온 화합물을 포함하는 파킨슨병 예방 또는 치료용 약학적 조성물 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE248589C (es) | ||||
| NL120029C (es) * | 1959-09-29 | |||
| GB965925A (en) * | 1961-03-04 | 1964-08-06 | Francesco Angelini | Improvements in or relating to 1,2,4-oxadiazole derivatives |
| GB969813A (en) * | 1962-03-26 | 1964-09-16 | Francesco Angelini | Improvements in or relating to 1,2,4-oxadiazole derivatives |
| US3245989A (en) * | 1962-12-15 | 1966-04-12 | Acraf | 3-aminophenyl-5-aminoloweralkyl-1, 2, 4-oxadiazoles |
| NL302496A (es) | 1962-12-22 | |||
| FR1386543A (fr) * | 1962-12-22 | 1965-01-22 | Shionigi & Co | Préparation de composés d'isoxazole et nouveaux produits ainsi obtenus |
| DD248589A1 (de) * | 1986-04-24 | 1987-08-12 | Univ Berlin Humboldt | Verfahren zur herstellung von substituierten 1,2,4-triazolen |
| DD263987A1 (de) * | 1987-08-07 | 1989-01-18 | Univ Berlin Humboldt | Verfahren zur herstellung von 5-(omega-aminoalkyl)-1,2,4-oxadiazolsalzen |
| JPH04295470A (ja) * | 1991-03-22 | 1992-10-20 | Wakamoto Pharmaceut Co Ltd | モノアミンオキシダーゼ−b酵素阻害活性を有する1,2,4−オキサジアゾール誘導体及びその製造法 |
| HUP9602763A3 (en) * | 1996-10-09 | 1999-05-28 | Egyt Gyogyszervegyeszeti Gyar | 3-phenyl isoxazole derivatives, process for producing them and pharmaceutical compositions containing the same |
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| TWI292316B (en) * | 1999-10-11 | 2008-01-11 | Sod Conseils Rech Applic | Pharmaceutical composition of thiazole derivatives intended to inhibit mao and/or lipidic peroxidation and/or to act as modulators of sodium channels and the use thereof |
| CN1151150C (zh) * | 2001-02-13 | 2004-05-26 | 王建武 | 一类非肽血管紧张素Ⅱ受体拮抗剂Jwsartan化合物及其合成方法与用途 |
| US20050171358A1 (en) | 2002-03-07 | 2005-08-04 | Noriko Shimozono | Substituted isoxazole alkylamine derivative and agri-and horticultural fungicide |
| HRP20040952A2 (en) * | 2002-04-26 | 2005-06-30 | F. Hoffmann - La Roche Ag | Isoquinoline derivatives |
| PE20050077A1 (es) * | 2002-09-20 | 2005-03-01 | Hoffmann La Roche | Derivados de 4-pirrolidino-fenil-bencil-eter |
| US7903538B2 (en) | 2003-08-06 | 2011-03-08 | Intel Corporation | Technique to select transmission parameters |
| DE602004017206D1 (de) * | 2003-10-23 | 2008-11-27 | Hoffmann La Roche | Benzazepin-derivate als mao-b-hemmer |
| ATE544765T1 (de) * | 2003-12-22 | 2012-02-15 | Leuven K U Res & Dev | Imidazoä4,5-cüpyridinverbindungen und verfahren zur antiviralen behandlung |
| US7790730B2 (en) | 2004-07-27 | 2010-09-07 | Gilead Sciences, Inc. | Imidazo[4,5-d]pyrimidines, their uses and methods of preparation |
| AU2005268894B2 (en) * | 2004-08-02 | 2010-12-16 | F. Hoffmann-La Roche Ag | Benzyloxy derivatives as MAOB inhibitors |
| US7750015B2 (en) * | 2005-05-17 | 2010-07-06 | Schering Corporation | Nitrogen-containing heterocyclic compounds and methods of use thereof |
| CN100488979C (zh) * | 2005-10-14 | 2009-05-20 | 天津药物研究院 | 甘草次酸-30-酰胺类衍生物及其用途 |
| US20070197532A1 (en) | 2005-11-18 | 2007-08-23 | Cao Sheldon X | Glucokinase activators |
| JP2010513283A (ja) * | 2006-12-15 | 2010-04-30 | アボット・ラボラトリーズ | 新規なオキサジアゾール化合物 |
| KR20100056462A (ko) * | 2007-07-13 | 2010-05-27 | 글락소스미스클라인 엘엘씨 | 항바이러스 화합물, 조성물 및 용도 |
| WO2009010479A2 (en) | 2007-07-13 | 2009-01-22 | Euroscreen S.A. | Heterocyclic methylene piperidine derivatives and their use |
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2010
- 2010-02-24 KR KR1020100016686A patent/KR101220182B1/ko active Active
- 2010-02-25 MX MX2011008910A patent/MX2011008910A/es active IP Right Grant
- 2010-02-25 CA CA2751343A patent/CA2751343C/en active Active
- 2010-02-25 EP EP10746439.8A patent/EP2401263B1/en active Active
- 2010-02-25 US US13/202,449 patent/US8828992B2/en active Active
- 2010-02-25 BR BRPI1008727A patent/BRPI1008727B8/pt not_active IP Right Cessation
- 2010-02-25 ES ES10746439.8T patent/ES2566482T3/es active Active
- 2010-02-25 JP JP2011551984A patent/JP5717031B2/ja active Active
- 2010-02-25 WO PCT/KR2010/001186 patent/WO2010098600A2/en not_active Ceased
- 2010-02-25 PL PL10746439T patent/PL2401263T3/pl unknown
- 2010-02-25 AU AU2010218584A patent/AU2010218584B2/en not_active Ceased
- 2010-02-25 RU RU2011134423/04A patent/RU2578596C2/ru not_active Application Discontinuation
- 2010-02-25 CN CN201080009749.2A patent/CN102333764B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2401263B1 (en) | 2016-02-17 |
| US8828992B2 (en) | 2014-09-09 |
| US20110301150A1 (en) | 2011-12-08 |
| KR20100097059A (ko) | 2010-09-02 |
| CA2751343C (en) | 2017-04-25 |
| MX2011008910A (es) | 2011-09-08 |
| EP2401263A4 (en) | 2012-11-28 |
| JP2012518683A (ja) | 2012-08-16 |
| JP5717031B2 (ja) | 2015-05-13 |
| BRPI1008727A2 (pt) | 2016-03-08 |
| AU2010218584A1 (en) | 2011-08-18 |
| CN102333764A (zh) | 2012-01-25 |
| KR101220182B1 (ko) | 2013-01-11 |
| EP2401263A2 (en) | 2012-01-04 |
| WO2010098600A3 (en) | 2011-01-06 |
| BRPI1008727B1 (pt) | 2020-07-28 |
| RU2011134423A (ru) | 2013-04-10 |
| HK1165798A1 (zh) | 2012-10-12 |
| AU2010218584B2 (en) | 2015-12-03 |
| RU2578596C2 (ru) | 2016-03-27 |
| PL2401263T3 (pl) | 2016-08-31 |
| CN102333764B (zh) | 2016-01-06 |
| CA2751343A1 (en) | 2010-09-02 |
| BRPI1008727B8 (pt) | 2021-05-25 |
| WO2010098600A2 (en) | 2010-09-02 |
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