AR113818A2 - Pirazolo-quinazolinas como inhibidores de proteína quinasa - Google Patents
Pirazolo-quinazolinas como inhibidores de proteína quinasaInfo
- Publication number
- AR113818A2 AR113818A2 ARP180103174A ARP180103174A AR113818A2 AR 113818 A2 AR113818 A2 AR 113818A2 AR P180103174 A ARP180103174 A AR P180103174A AR P180103174 A ARP180103174 A AR P180103174A AR 113818 A2 AR113818 A2 AR 113818A2
- Authority
- AR
- Argentina
- Prior art keywords
- group
- cycloalkyl
- aryl
- heterocyclyl
- compounds
- Prior art date
Links
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title 1
- 239000003909 protein kinase inhibitor Substances 0.000 title 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 2
- 102000001253 Protein Kinase Human genes 0.000 abstract 2
- 201000010099 disease Diseases 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 2
- 108060006633 protein kinase Proteins 0.000 abstract 2
- GNOYRJIXSUNXIH-UHFFFAOYSA-N N1=CNC2=C3C=NN=C3C=CC2=C1 Chemical class N1=CNC2=C3C=NN=C3C=CC2=C1 GNOYRJIXSUNXIH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000002074 deregulated effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
Abstract
La presente se refiere a pirazolo-quinazolinas, caracterizadas por un residuo aril-orto-sustituido-amino, heterociclilamino- o C₃₋₇ cicloalquilamino en la posición 8, y un arilo, heterociclilo o C₃₋₇ cicloalquilo como sustituyente de una carboxamida en la posición 3 del esqueleto de la molécula. Los compuestos de esta modulan la actividad de las proteína quinasas, y por lo tanto son útiles para tratar enfermedades causadas por una actividad de proteína quinasa desregulada, en particular MPS1 / TTK. La presente también proporciona métodos para preparar estos compuestos, composiciones farmacéuticas que comprenden estos compuestos, y métodos para tratar enfermedades utilizando composiciones farmacéuticas que comprenden estos compuestos. Reivindicación 1: Un compuesto caracterizado porque tiene la fórmula (1), donde: R¹ es un grupo arilo orto-sustituido o un heterociclilo o un grupo C₃₋₇ cicloalquilo; R² es un átomo de hidrógeno o un grupo C₁₋₆ alquilo recto o ramificado, C₂₋₆ alquenilo, C₂₋₆ alquinilo, C₃₋₇ cicloalquilo o heterociclilo; R³ es un grupo arilo; R⁴ es un átomo de hidrógeno, hidroxilo o un grupo C₁₋₆ alquilo, cuyo grupo puede ser opcionalmente ciclado junto con uno de los átomos del grupo que puede representar R³, para formar un grupo cíclico C₄₋₇ fusionado; R⁵ y R⁶: son cada uno independientemente un átomo de hidrógeno, C₁₋₆ alquilo, o son opcionalmente ciclados juntos con el átomo de carbono al cual están unidos para formar un grupo C₃₋₇ cicloalquilo; donde los grupos arilo orto-sustituido, arilo, heterociclilo, C₃₋₇ cicloalquilo, C₄₋₇ cicloalquilo, C₁₋₆ alquilo, C₂₋₆ alquenilo y C₂₋₆ alquinilo pueden estar opcionalmente sustituidos (adicionalmente); y sus sales farmacéuticamente aceptables.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08159114 | 2008-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR113818A2 true AR113818A2 (es) | 2020-06-17 |
Family
ID=40887152
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090102378A AR072374A1 (es) | 2008-06-26 | 2009-06-26 | Pirazolo-quinazolinas, composicion farmaceutica que las comprende y su uso en la preparacion de medicamentos para el tratamiento de enfermedades asociadas a la actividad de la proteina quinasa alterada. |
| ARP180103174A AR113818A2 (es) | 2008-06-26 | 2018-10-31 | Pirazolo-quinazolinas como inhibidores de proteína quinasa |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090102378A AR072374A1 (es) | 2008-06-26 | 2009-06-26 | Pirazolo-quinazolinas, composicion farmaceutica que las comprende y su uso en la preparacion de medicamentos para el tratamiento de enfermedades asociadas a la actividad de la proteina quinasa alterada. |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8846701B2 (es) |
| EP (1) | EP2303891B1 (es) |
| JP (1) | JP5542133B2 (es) |
| CN (1) | CN102076689B (es) |
| AR (2) | AR072374A1 (es) |
| AU (1) | AU2009264431B2 (es) |
| BR (1) | BRPI0914649B1 (es) |
| CA (1) | CA2729436C (es) |
| CL (1) | CL2010001538A1 (es) |
| CY (1) | CY1117595T1 (es) |
| DK (1) | DK2303891T3 (es) |
| EA (1) | EA020703B9 (es) |
| ES (1) | ES2572360T3 (es) |
| HR (1) | HRP20160243T1 (es) |
| HU (1) | HUE027527T2 (es) |
| MX (1) | MX2010013843A (es) |
| PL (1) | PL2303891T3 (es) |
| SI (1) | SI2303891T1 (es) |
| TW (1) | TWI464172B (es) |
| WO (1) | WO2009156315A1 (es) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5400791B2 (ja) * | 2007-12-04 | 2014-01-29 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | 置換ジヒドロプテリジン−６−オン誘導体、その製造方法及びキナーゼ阻害剤としてのその使用 |
| EP2417125B1 (en) * | 2009-03-27 | 2015-09-09 | Nerviano Medical Sciences S.r.l. | N-aryl-2-(2-arylaminopyrimidin-4-yl)pyrrol-4-carboxamide derivatives as mps1 kinase inhibitors |
| JP5997143B2 (ja) * | 2010-07-30 | 2016-09-28 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | タンパク質キナーゼ活性の調整剤としてのイソオキサゾロ−キナゾリン |
| UA113280C2 (xx) | 2010-11-11 | 2017-01-10 | АМІНОСПИРТЗАМІЩЕНІ ПОХІДНІ 2,3-ДИГІДРОІМІДАЗО$1,2-c]ХІНАЗОЛІНУ, ПРИДАТНІ ДЛЯ ЛІКУВАННЯ ГІПЕРПРОЛІФЕРАТИВНИХ ПОРУШЕНЬ І ЗАХВОРЮВАНЬ, ПОВ'ЯЗАНИХ З АНГІОГЕНЕЗОМ | |
| CN103370322B (zh) * | 2010-12-17 | 2016-02-10 | 拜耳知识产权有限责任公司 | 在过度增殖性病症的治疗中用作mps-1和tkk抑制剂的2-取代的咪唑并吡嗪 |
| RU2652638C2 (ru) * | 2010-12-17 | 2018-04-28 | НЕРВИАНО МЕДИКАЛ САЙЕНСИЗ С.р.л. | Замещенные пиразолхиназолиновые производные в качестве ингибиторов киназы |
| CA3142576A1 (en) * | 2011-01-21 | 2012-07-26 | Basilea Pharmaceutica Ag | Use of bubr1 as a biomarker of drug response to furazanobenzimidazoles |
| EP2668188B1 (en) | 2011-01-26 | 2016-05-18 | Nerviano Medical Sciences S.r.l. | Tricyclic derivatives, process for their preparation and their use as kinase inhibitors |
| CN103339134B (zh) * | 2011-01-26 | 2015-12-23 | 内尔维阿诺医学科学有限公司 | 三环吡咯并衍生物、它们的制备方法和它们作为激酶抑制剂的应用 |
| EP2702055A1 (en) | 2011-04-11 | 2014-03-05 | Nerviano Medical Sciences S.r.l. | Pyrazolyl-pyrimidine derivatives as kinase inhibitors |
| CN104379563B (zh) * | 2012-04-10 | 2018-12-21 | 加利福尼亚大学董事会 | 用于治疗癌症的组合物和方法 |
| WO2014020041A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| WO2014020043A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| CN103130810B (zh) * | 2013-03-11 | 2015-02-25 | 河南师范大学 | 一种吡唑并[1,5-c]喹唑啉类化合物的合成方法 |
| CN106132963B (zh) * | 2014-04-07 | 2019-08-06 | 荷兰转化研究中心有限责任公司 | (5,6-二氢)嘧啶并[4,5-e]吲嗪 |
| CN107567503B (zh) | 2015-04-17 | 2022-03-22 | 荷兰转化研究中心有限责任公司 | 用于ttk抑制剂化疗的预后生物标记 |
| UY37778A (es) * | 2017-06-29 | 2019-01-31 | Servier Lab | NUEVA SAL DE N-(2,6-DIETILFENIL)-8-({4-[4-(DIMETILAMINO)PIPERIDIN-1-IL]-2- METOXIFENIL}AMINO)-1-METIL-4,5-DIHIDRO- 1H-PIRAZOLO[4,3-h]QUINAZOLINA-3- CARBOXAMIDA, SU PREPARACIÓN, Y LAS FORMULACIONES QUE LA CONTIENEN |
| WO2019002542A1 (en) * | 2017-06-30 | 2019-01-03 | Les Laboratoires Servier | COMBINATION OF AN INHIBITOR OF MPS1 AND A TAXANE COMPOUND, USES THEREOF AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAME |
| WO2019011715A1 (en) * | 2017-07-11 | 2019-01-17 | Nerviano Medical Sciences S.R.L. | PYRAZOLO-QUINAZOLINE DERIVATIVES AS INHIBITORS OF CHOLINE KINASE |
| KR102464677B1 (ko) * | 2017-08-11 | 2022-11-10 | 셍커 파마슈티컬스 (지앙수) 엘티디. | 단백질 인산화효소 억제제로 작용하는 1h-피라졸로[4,3-h]퀴나졸린 화합물 |
| CA3171979A1 (en) | 2020-03-27 | 2021-09-30 | Josep Bassaganya-Riera | Plxdc2 ligands |
| US20230416271A1 (en) * | 2020-11-26 | 2023-12-28 | Chengdu Cynogen Bio-Pharmaceutical Technology Co., Ltd. | Heteroarylquinazoline compounds as protein kinase inhibitors |
| CN114685520B (zh) * | 2020-12-25 | 2024-08-30 | 武汉誉祥医药科技有限公司 | 三并环化合物及其药物组合物和应用 |
| CN116528871A (zh) * | 2020-12-31 | 2023-08-01 | 恒元生物医药科技(苏州)有限公司 | 一种吡唑并喹唑啉类化合物、其制备方法及应用 |
| WO2023113478A1 (en) * | 2021-12-15 | 2023-06-22 | Sillajen, Inc. | Methods of treating neoplastic diseases |
| WO2025021587A1 (en) | 2023-07-21 | 2025-01-30 | Nerviano Medical Sciences S.R.L. | Combination of a mps1 inhibitor and immune checkpoint inhibitors, uses and pharmaceutical compositions thereof |
| EP4506015A1 (en) | 2023-08-09 | 2025-02-12 | Nerviano Medical Sciences S.r.l. | Combination of a mps1 inhibitor and an antibody drug conjugate |
| CN119060058A (zh) * | 2024-08-21 | 2024-12-03 | 武汉九州钰民医药科技有限公司 | 一种甲苯磺酸利特昔替尼的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998028281A1 (en) * | 1996-12-23 | 1998-07-02 | Celltech Therapeutics Limited | Fused polycyclic 2-aminopyrimidine derivatives, their preparation and their use as protein tyrosine kinase inhibitors |
| MXPA04008130A (es) * | 2002-02-19 | 2004-11-26 | Pharmacia Corp | Derivados triciclicos de pirazol para el tratamiento de la inflamacion. |
| US7482354B2 (en) * | 2003-05-22 | 2009-01-27 | Nerviano Medical Sciences S.R.L. | Pyrazolo-quinazoline derivatives, process for their preparation and their use as kinase inhibitors |
| KR101512284B1 (ko) * | 2006-12-21 | 2015-04-15 | 네르비아노 메디칼 사이언시스 에스.알.엘. | 치환된 피라졸로-퀴나졸린 유도체, 이의 제조방법, 및 키나제 억제제로서의 이의 용도 |
-
2009
- 2009-06-17 EP EP09769164.6A patent/EP2303891B1/en active Active
- 2009-06-17 EA EA201170090A patent/EA020703B9/ru unknown
- 2009-06-17 CN CN200980123813.7A patent/CN102076689B/zh active Active
- 2009-06-17 PL PL09769164T patent/PL2303891T3/pl unknown
- 2009-06-17 US US13/001,331 patent/US8846701B2/en active Active
- 2009-06-17 JP JP2011515314A patent/JP5542133B2/ja active Active
- 2009-06-17 HR HRP20160243TT patent/HRP20160243T1/hr unknown
- 2009-06-17 CA CA2729436A patent/CA2729436C/en active Active
- 2009-06-17 HU HUE09769164A patent/HUE027527T2/en unknown
- 2009-06-17 DK DK09769164.6T patent/DK2303891T3/en active
- 2009-06-17 WO PCT/EP2009/057512 patent/WO2009156315A1/en not_active Ceased
- 2009-06-17 MX MX2010013843A patent/MX2010013843A/es active IP Right Grant
- 2009-06-17 SI SI200931429A patent/SI2303891T1/sl unknown
- 2009-06-17 ES ES09769164T patent/ES2572360T3/es active Active
- 2009-06-17 BR BRPI0914649-0A patent/BRPI0914649B1/pt active IP Right Grant
- 2009-06-17 AU AU2009264431A patent/AU2009264431B2/en active Active
- 2009-06-25 TW TW098121326A patent/TWI464172B/zh active
- 2009-06-26 AR ARP090102378A patent/AR072374A1/es not_active Application Discontinuation
-
2010
- 2010-12-23 CL CL2010001538A patent/CL2010001538A1/es unknown
-
2016
- 2016-05-12 CY CY20161100403T patent/CY1117595T1/el unknown
-
2018
- 2018-10-31 AR ARP180103174A patent/AR113818A2/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2572360T3 (es) | 2016-05-31 |
| TW201004960A (en) | 2010-02-01 |
| US8846701B2 (en) | 2014-09-30 |
| EA201170090A1 (ru) | 2011-08-30 |
| HK1154383A1 (en) | 2012-04-20 |
| PL2303891T3 (pl) | 2016-08-31 |
| BRPI0914649A2 (pt) | 2015-07-07 |
| AU2009264431B2 (en) | 2013-11-07 |
| JP2011525516A (ja) | 2011-09-22 |
| HUE027527T2 (en) | 2016-10-28 |
| CA2729436A1 (en) | 2009-12-30 |
| AU2009264431A1 (en) | 2009-12-30 |
| EP2303891A1 (en) | 2011-04-06 |
| US20110105542A1 (en) | 2011-05-05 |
| AU2009264431A2 (en) | 2011-02-17 |
| CN102076689B (zh) | 2014-10-15 |
| CA2729436C (en) | 2016-08-09 |
| EA020703B9 (ru) | 2015-12-30 |
| BRPI0914649B1 (pt) | 2021-07-06 |
| HRP20160243T1 (hr) | 2016-04-08 |
| WO2009156315A1 (en) | 2009-12-30 |
| DK2303891T3 (en) | 2016-05-30 |
| EA020703B1 (ru) | 2015-01-30 |
| CL2010001538A1 (es) | 2012-02-03 |
| AR072374A1 (es) | 2010-08-25 |
| TWI464172B (zh) | 2014-12-11 |
| SI2303891T1 (sl) | 2016-06-30 |
| EP2303891B1 (en) | 2016-02-17 |
| MX2010013843A (es) | 2011-01-21 |
| CY1117595T1 (el) | 2017-04-26 |
| JP5542133B2 (ja) | 2014-07-09 |
| CN102076689A (zh) | 2011-05-25 |
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