BRPI1014174B8 - uso de um composto selecionado a partir de 4-((1s)-1-{[5-cloro-2-(4-fluorofenóxi)benzoil]amino}etil)ácido benzóico, 4-[(1s)-1-({[5-cloro-2-(3-fluorofenóxi)piridin-3-il]carbonil}amino)etil]ácido benzóico e 3-[2-(4-{2-etil-4,6-dimetil-1h-imidazo[4,5-c]piridin-1-il}fenil)etil]-1-[(4-metilbenzeno)sulfonil]urea para tratamento de um câncer epitelial relacionado à pge2 - Google Patents
uso de um composto selecionado a partir de 4-((1s)-1-{[5-cloro-2-(4-fluorofenóxi)benzoil]amino}etil)ácido benzóico, 4-[(1s)-1-({[5-cloro-2-(3-fluorofenóxi)piridin-3-il]carbonil}amino)etil]ácido benzóico e 3-[2-(4-{2-etil-4,6-dimetil-1h-imidazo[4,5-c]piridin-1-il}fenil)etil]-1-[(4-metilbenzeno)sulfonil]urea para tratamento de um câncer epitelial relacionado à pge2Info
- Publication number
- BRPI1014174B8 BRPI1014174B8 BRPI1014174A BRPI1014174A BRPI1014174B8 BR PI1014174 B8 BRPI1014174 B8 BR PI1014174B8 BR PI1014174 A BRPI1014174 A BR PI1014174A BR PI1014174 A BRPI1014174 A BR PI1014174A BR PI1014174 B8 BRPI1014174 B8 BR PI1014174B8
- Authority
- BR
- Brazil
- Prior art keywords
- ethyl
- fluorophenoxy
- pyridin
- chloro
- amino
- Prior art date
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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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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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
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
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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
-
- 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
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
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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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2121/00—Preparations for use in therapy
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
uso de um composto da formula (i), (ii) (ill) ou (iv) ou um sal farmaceuticamente aceitável seu para a fabricação de um medicamento para o tratamento de câncer em um humano ou um animal; método para o tratamento de câncer, pacote comercial,método para redução de células cancerosas e kit para o tratamento de câncer. esta invenção prove um medicamento para o tratamento do câncer, que provoca a redução do câncer. esta invenção refere-se ao uso de um composto que tem atividade inibidoras contra o receptor de prostaglandina e2 (receptor de ep4) e é representado pela seguinte formula geral (i), (il), (ill) ou (iv) ou um sal farmaceuticamente aceitável seu, ou uma composição farmacêutica compreendendo composto ou o sal para a fabricação de um medicamento para o tratamento de câncer. a invenção refere-se a um método para tratamento do câncer compreendendo administrar o composto ou um sal farmaceuticamente aceitável seu, ou uma composição farmacêutica compreendendo o composto ou o sal aos humanos ou animais.o composto ou um sal farmaceuticamente aceitável seu, ou a composição farmacêutica pode ser usado em combinação com um ou mais segundos agentes ativos.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009104568 | 2009-04-22 | ||
| JP2009104568 | 2009-04-22 | ||
| JP2010015445 | 2010-01-27 | ||
| JP2010015445 | 2010-01-27 | ||
| PCT/JP2010/057114 WO2010123049A1 (ja) | 2009-04-22 | 2010-04-22 | 癌治療のための選択的ep4受容体拮抗物質 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| BRPI1014174A2 BRPI1014174A2 (pt) | 2016-04-05 |
| BRPI1014174B1 BRPI1014174B1 (pt) | 2020-10-06 |
| BRPI1014174B8 true BRPI1014174B8 (pt) | 2021-05-25 |
Family
ID=43011165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI1014174A BRPI1014174B8 (pt) | 2009-04-22 | 2010-04-22 | uso de um composto selecionado a partir de 4-((1s)-1-{[5-cloro-2-(4-fluorofenóxi)benzoil]amino}etil)ácido benzóico, 4-[(1s)-1-({[5-cloro-2-(3-fluorofenóxi)piridin-3-il]carbonil}amino)etil]ácido benzóico e 3-[2-(4-{2-etil-4,6-dimetil-1h-imidazo[4,5-c]piridin-1-il}fenil)etil]-1-[(4-metilbenzeno)sulfonil]urea para tratamento de um câncer epitelial relacionado à pge2 |
Country Status (11)
| Country | Link |
|---|---|
| US (5) | US8921391B2 (pt) |
| EP (3) | EP2965756B1 (pt) |
| JP (1) | JP5668219B2 (pt) |
| KR (1) | KR101575706B1 (pt) |
| CN (2) | CN105596320B (pt) |
| BR (1) | BRPI1014174B8 (pt) |
| CA (1) | CA2754702C (pt) |
| ES (3) | ES2698508T3 (pt) |
| MX (2) | MX369117B (pt) |
| RU (1) | RU2563817C2 (pt) |
| WO (1) | WO2010123049A1 (pt) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2754702C (en) * | 2009-04-22 | 2016-06-07 | Yukinori Take | Selective ep4 antagonistic substance for treatment of cancer |
| SG11201609770TA (en) * | 2014-05-23 | 2016-12-29 | Eisai R&D Man Co Ltd | Combination therapies for the treatment of cancer |
| US10342785B2 (en) * | 2016-11-04 | 2019-07-09 | Askat Inc. | Use of EP4 receptor antagonists for the treatment of NASH-associated liver cancer |
| CN107383004B (zh) * | 2017-07-05 | 2020-04-17 | 浙江大学 | 2-氨基咪唑并吡啶类衍生物及制备和应用 |
| CN112292128A (zh) * | 2018-04-16 | 2021-01-29 | 阿瑞斯医疗有限公司 | Ep4抑制剂和其用途 |
| US20210315909A1 (en) | 2018-07-11 | 2021-10-14 | Arrys Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| IL280051B2 (en) * | 2018-07-11 | 2024-03-01 | Arrys Therapeutics Inc | EP4 inhibitors and their synthesis |
| CA3113468A1 (en) * | 2018-09-27 | 2020-04-02 | Arrys Therapeutics, Inc. | Grapiprant unit dosage forms |
| LT3860998T (lt) | 2018-10-05 | 2024-06-25 | Annapurna Bio Inc. | Junginiai ir kompozicijos, skirti gydyti būkles, susijusias su apj receptoriaus aktyvumu |
| CN114206866A (zh) * | 2019-06-11 | 2022-03-18 | 泰昂治疗公司 | 前列腺素e2受体4拮抗剂及其用途 |
| GB201914585D0 (en) | 2019-10-09 | 2019-11-20 | Heptares Therapeutics Ltd | Prostaglandin ep4 receptor antagonist compounds |
| WO2022247881A1 (zh) * | 2021-05-28 | 2022-12-01 | 凯复(苏州)生物医药有限公司 | 治疗肿瘤的联合疗法 |
| CN119634669B (zh) * | 2024-11-12 | 2025-11-14 | 北京航空材料研究院股份有限公司 | 含有多角度管腔的蜡模制备方法 |
| CN119657828B (zh) * | 2024-11-12 | 2025-11-14 | 北京航空材料研究院股份有限公司 | 一种带多角度管腔型壳的制备方法及模具 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1080728A1 (en) * | 1999-03-16 | 2001-03-07 | Toray Industries, Inc. | Prostaglandin ep4 receptor agonist and treatment method |
| AU6836200A (en) * | 1999-08-10 | 2001-03-05 | Glaxo Group Limited | Use of ep4 receptor ligands in the treatment of, inter alia, neuropathic pain and colon cancer |
| US6710205B2 (en) | 2000-02-22 | 2004-03-23 | Ono Pharmaceutical Co., Ltd. | Benzoic acid derivatives, processes for producing the same and drugs containing the same as the active ingredient |
| WO2001062708A1 (fr) * | 2000-02-22 | 2001-08-30 | Ono Pharmaceutical Co., Ltd. | Derives d'acide benzoique, procede de production desdits derives, et medicament contenant ces derives comme principe actif |
| HN2001000224A (es) * | 2000-10-19 | 2002-06-13 | Pfizer | Compuestos de imidazol condensado con arilo o heteroarilo como agentes anti - inflamatorios y analgesicos. |
| MXPA04009961A (es) | 2002-04-12 | 2004-12-13 | Pfizer | Compuestos de imidazol como agentes anti-inflamatorios y analgesicos. |
| CN1646122A (zh) | 2002-04-16 | 2005-07-27 | 藤泽药品工业株式会社 | 用于预防和/或治疗慢性排斥的药物 |
| CA2536870C (en) | 2003-09-03 | 2009-10-27 | Pfizer Inc. | Phenyl or pyridyl amide compounds as prostaglandin e2 antagonists |
| JP2007533723A (ja) * | 2004-04-20 | 2007-11-22 | ファイザー・プロダクツ・インク | α2δリガンドを含む組合せ |
| AU2005238291A1 (en) | 2004-05-04 | 2005-11-10 | Pfizer Inc. | Substituted methyl aryl or heteroaryl amide compounds |
| KR20070006890A (ko) * | 2004-05-04 | 2007-01-11 | 화이자 인코포레이티드 | 오르토 치환된 아릴 또는 헤테로아릴 아마이드 화합물 |
| AU2006221699A1 (en) | 2005-03-11 | 2006-09-14 | Pfizer Inc. | Crystal forms of an imidazole derivative |
| ATE533766T1 (de) | 2005-05-19 | 2011-12-15 | Merck Canada Inc | Chinolinderivate als ep4-antagonisten |
| CA2754702C (en) | 2009-04-22 | 2016-06-07 | Yukinori Take | Selective ep4 antagonistic substance for treatment of cancer |
| KR101539436B1 (ko) | 2013-12-30 | 2015-07-24 | 주식회사 효성 | 가스 절연 개폐기의 부분 방전 검출 장치 |
-
2010
- 2010-04-22 CA CA2754702A patent/CA2754702C/en active Active
- 2010-04-22 MX MX2016008394A patent/MX369117B/es unknown
- 2010-04-22 BR BRPI1014174A patent/BRPI1014174B8/pt active IP Right Grant
- 2010-04-22 MX MX2011011058A patent/MX345032B/es active IP Right Grant
- 2010-04-22 EP EP15182580.9A patent/EP2965756B1/en active Active
- 2010-04-22 WO PCT/JP2010/057114 patent/WO2010123049A1/ja not_active Ceased
- 2010-04-22 ES ES15182580T patent/ES2698508T3/es active Active
- 2010-04-22 EP EP10767106.7A patent/EP2422779B1/en active Active
- 2010-04-22 JP JP2011510353A patent/JP5668219B2/ja active Active
- 2010-04-22 CN CN201510982848.3A patent/CN105596320B/zh active Active
- 2010-04-22 ES ES10767106.7T patent/ES2562814T3/es active Active
- 2010-04-22 ES ES18191714T patent/ES2960438T3/es active Active
- 2010-04-22 CN CN201080017743.XA patent/CN102421429B/zh active Active
- 2010-04-22 RU RU2011147194/15A patent/RU2563817C2/ru active
- 2010-04-22 US US13/265,216 patent/US8921391B2/en active Active
- 2010-04-22 EP EP18191714.7A patent/EP3431085B1/en active Active
- 2010-04-22 KR KR1020117027678A patent/KR101575706B1/ko active Active
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2014
- 2014-11-19 US US14/547,247 patent/US9688674B2/en active Active
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2017
- 2017-05-23 US US15/602,686 patent/US10611761B2/en active Active
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2020
- 2020-02-27 US US16/803,163 patent/US10947235B2/en active Active
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2021
- 2021-03-15 US US17/201,102 patent/US11840530B2/en active Active
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