CN103200822B - 2-取代-8-烷基-7-氧代-7,8-二氢吡啶并[2,3-d]嘧啶-6-腈和其应用 - Google Patents
2-取代-8-烷基-7-氧代-7,8-二氢吡啶并[2,3-d]嘧啶-6-腈和其应用 Download PDFInfo
- Publication number
- CN103200822B CN103200822B CN201180038325.3A CN201180038325A CN103200822B CN 103200822 B CN103200822 B CN 103200822B CN 201180038325 A CN201180038325 A CN 201180038325A CN 103200822 B CN103200822 B CN 103200822B
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- China
- Prior art keywords
- compound
- pyrimidine
- oxo
- cancer
- formula
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- SNNHLSHDDGJVDM-UHFFFAOYSA-N CCOC(c(c(Cl)n1)cnc1SC)=O Chemical compound CCOC(c(c(Cl)n1)cnc1SC)=O SNNHLSHDDGJVDM-UHFFFAOYSA-N 0.000 description 1
- 0 CSc1ncc(C=O)c(N*)n1 Chemical compound CSc1ncc(C=O)c(N*)n1 0.000 description 1
- KBPPTUDYXRJMOR-UHFFFAOYSA-N N#CC(C(N1C2CCCC2)=O)=Cc2c1nc(Nc(cc1)ccc1N1CCNCC1)nc2 Chemical compound N#CC(C(N1C2CCCC2)=O)=Cc2c1nc(Nc(cc1)ccc1N1CCNCC1)nc2 KBPPTUDYXRJMOR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Oncology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37094610P | 2010-08-05 | 2010-08-05 | |
| US61/370,946 | 2010-08-05 | ||
| PCT/US2011/044807 WO2012018540A1 (en) | 2010-08-05 | 2011-07-21 | 2-substituted-8-alkyl-7-oxo-7,8-dihydropyrido[2,3-d] pyrimidine-6-carbonitriles and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103200822A CN103200822A (zh) | 2013-07-10 |
| CN103200822B true CN103200822B (zh) | 2014-12-24 |
Family
ID=45559737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180038325.3A Active CN103200822B (zh) | 2010-08-05 | 2011-07-21 | 2-取代-8-烷基-7-氧代-7,8-二氢吡啶并[2,3-d]嘧啶-6-腈和其应用 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US8987267B2 (enExample) |
| EP (1) | EP2600719B1 (enExample) |
| JP (1) | JP5512894B2 (enExample) |
| KR (1) | KR101434841B1 (enExample) |
| CN (1) | CN103200822B (enExample) |
| AU (1) | AU2011286282B2 (enExample) |
| BR (1) | BR112013002375B1 (enExample) |
| CA (1) | CA2807498C (enExample) |
| DK (1) | DK2600719T3 (enExample) |
| EA (1) | EA022527B1 (enExample) |
| ES (1) | ES2525866T3 (enExample) |
| IL (1) | IL224555A (enExample) |
| MX (1) | MX2013001427A (enExample) |
| NZ (1) | NZ606281A (enExample) |
| PL (1) | PL2600719T3 (enExample) |
| PT (1) | PT2600719E (enExample) |
| WO (1) | WO2012018540A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112013002375B1 (pt) * | 2010-08-05 | 2020-05-12 | Temple University - Of The Commonwealth System Of Higher Education | Composto, processo de preparação do mesmo, composição farmacêutica, e, usos de um composto |
| WO2014031571A1 (en) * | 2012-08-21 | 2014-02-27 | Icahn School Of Medicine At Mount Sinai | Treatment of viral infections |
| EP3733184B1 (en) | 2013-03-14 | 2023-08-30 | Icahn School of Medicine at Mount Sinai | Pyrimidine compounds for use in the treatment of cancer |
| WO2015154064A2 (en) | 2014-04-04 | 2015-10-08 | Del Mar Pharmaceuticals | Use of dianhydrogalactitol and analogs or derivatives thereof to treat non-small-cell carcinoma of the lung and ovarian cancer |
| AU2015296322B2 (en) | 2014-07-26 | 2019-09-19 | Sunshine Lake Pharma Co., Ltd. | 2-amino-pyrido[2,3-d]pyrimidin-7(8h)-one derivatives as CDK inhibitors and uses thereof |
| CN104447739B (zh) * | 2014-11-07 | 2016-02-17 | 郑州泰基鸿诺药物科技有限公司 | 一种氘代Palbociclib衍生物、制备方法及应用 |
| CN104496983B (zh) | 2014-11-26 | 2016-06-08 | 苏州明锐医药科技有限公司 | 一种帕博西尼的制备方法 |
| CN104447743B (zh) * | 2014-11-26 | 2016-03-02 | 苏州明锐医药科技有限公司 | 帕博西尼的制备方法 |
| CN104478874B (zh) * | 2014-12-08 | 2016-03-02 | 新发药业有限公司 | 一种帕博赛布的制备方法 |
| CN104610254B (zh) * | 2015-01-26 | 2017-02-01 | 新发药业有限公司 | 一种帕博赛布的低成本制备方法 |
| CN105111205B (zh) * | 2015-09-12 | 2017-01-04 | 山东罗欣药业集团股份有限公司 | 一种帕博西尼的制备方法 |
| JP7044801B2 (ja) | 2016-12-16 | 2022-03-30 | シーストーン・ファーマスーティカルズ・(スージョウ)・カンパニー・リミテッド | Cdk4/6阻害剤 |
| BR112020015431A2 (pt) | 2018-02-15 | 2020-12-08 | Nuvation Bio Inc. | Compostos heterocíclicos como inibidores de quinase |
| KR102286701B1 (ko) * | 2018-09-28 | 2021-08-06 | 재단법인 대구경북첨단의료산업진흥재단 | 피리도[2,3-d]피리미딘 유도체, 이의 제조방법 및 이를 유효성분으로 포함하는 암의 예방 또는 치료용 약학적 조성물 |
| US20220002293A1 (en) * | 2018-11-12 | 2022-01-06 | Onconova Therapeutics, Inc. | 8-cyclopentyl-7-oxo-2-(4-piperazin-1-yl-phenylamino)-7, 8-dihydro-pyrido [2,3-d]pyrimidine-6-carbonitrile and uses thereof in treating proliferative disorders |
| TWI818930B (zh) * | 2018-11-12 | 2023-10-21 | 美商昂可諾法治療股份有限公司 | 8-環戊基-7-側氧基-2-(4-哌嗪-1-基-苯基胺基)-7,8-二氫-吡啶[2,3-d]嘧啶-6-氰基及其用於治療增生性疾病的用途 |
| WO2020140053A1 (en) * | 2018-12-28 | 2020-07-02 | Spv Therapeutics Inc. | Cyclin-dependent kinase inhibitors |
| AU2019413683B2 (en) * | 2018-12-28 | 2025-05-22 | Spv Therapeutics Inc. | Cyclin-dependent kinase inhibitors |
| CN114340634A (zh) * | 2019-07-02 | 2022-04-12 | 诺维逊生物股份有限公司 | 作为激酶抑制剂的杂环化合物 |
| US11697648B2 (en) | 2019-11-26 | 2023-07-11 | Theravance Biopharma R&D Ip, Llc | Fused pyrimidine pyridinone compounds as JAK inhibitors |
| US20230132667A1 (en) * | 2020-05-28 | 2023-05-04 | University Of Washington | Drug-like molecules and methods for the therapeutic targeting of viral rna structures |
| KR20240115979A (ko) | 2021-11-08 | 2024-07-26 | 프로젠토스 테라퓨틱스, 인크. | 혈소판-유래 성장 인자 수용체(pdgfr) 알파 억제제 및 이의 용도 |
| JP2024542205A (ja) * | 2021-11-18 | 2024-11-13 | オンコノヴァ セラピューティクス, インコーポレイテッド | がんを処置するための方法および組成物 |
| EP4433060A1 (en) * | 2021-11-18 | 2024-09-25 | Onconova Therapeutics, Inc. | Methods and compositions for treating cancer |
| WO2023230288A1 (en) * | 2022-05-25 | 2023-11-30 | Onconova Therapeutics, Inc. | Methods and compositions for treating cancer |
| WO2024107730A1 (en) * | 2022-11-14 | 2024-05-23 | Onconova Therapeutics, Inc. | Methods and compositions for treating cancer |
| EP4618992A1 (en) * | 2022-11-17 | 2025-09-24 | Onconova Therapeutics, Inc. | Methods and compositions for treating cancer |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1302301A (zh) * | 1998-05-26 | 2001-07-04 | 沃尼尔·朗伯公司 | 用作细胞增殖抑制剂的二环嘧啶及二环3,4-二氢嘧啶化合物 |
| US20010027196A1 (en) * | 2000-02-25 | 2001-10-04 | Borroni Edilio Maurizio | Adenosine receptor ligands and their use in the treatment of disease |
| US6498163B1 (en) * | 1997-02-05 | 2002-12-24 | Warner-Lambert Company | Pyrido[2,3-D]pyrimidines and 4-aminopyrimidines as inhibitors of cellular proliferation |
| CN1422268A (zh) * | 2000-03-06 | 2003-06-04 | 沃尼尔·朗伯公司 | 5-烷基吡啶并[2,3-d]嘧啶酪氨酸激酶抑制剂 |
| CN1433417A (zh) * | 2000-01-27 | 2003-07-30 | 沃尼尔·朗伯公司 | 用于治疗神经变性疾病的吡啶并嘧啶酮衍生物 |
| US20080004285A1 (en) * | 2004-12-30 | 2008-01-03 | De Jonghe Steven C A | Pyrido(3,2-d)pyrimidines and pharmaceutical compositions useful for medical treatment |
| US20090062274A1 (en) * | 2005-10-07 | 2009-03-05 | Exelixis, Inc | Pyridopyrimidinone inhibitors of pi3kalpha |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5620981A (en) | 1995-05-03 | 1997-04-15 | Warner-Lambert Company | Pyrido [2,3-D]pyrimidines for inhibiting protein tyrosine kinase mediated cellular proliferation |
| JP4291696B2 (ja) | 2002-01-22 | 2009-07-08 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 2−(ピリジン−2−イルアミノ)−ピリド[2,3−d]ピリミジン−7−オン |
| CA2555724A1 (en) | 2004-02-18 | 2005-09-09 | Warner-Lambert Company Llc | 2-(pyridin-3-ylamino)-pyrido[2,3-d]pyrimidin-7-ones |
| WO2005105097A2 (en) | 2004-04-28 | 2005-11-10 | Gpc Biotech Ag | Pyridopyrimidines for treating inflammatory and other diseases |
| US20060142312A1 (en) | 2004-12-23 | 2006-06-29 | Pfizer Inc | C6-aryl and heteroaryl substituted pyrido[2,3-D] pyrimidin-7-ones |
| RU2007128961A (ru) * | 2004-12-30 | 2009-02-10 | 4 Аза Ип Ив (Be) | ПИРИДО(3,2-d)ПИРИМИДИНЫ И ФАРМАЦЕВТИЧЕСКИЕ ПРЕПАРАТЫ, ПОЛЕЗНЫЕ ДЛЯ КОНСЕРВАТИВНОГО ЛЕЧЕНИЯ |
| EP1899332A1 (en) * | 2005-06-24 | 2008-03-19 | Gilead Sciences, Inc. | Pyrido(3,2-d)pyrimidines and pharmaceutical compositions useful for treating hepatitis c. |
| EP1940839B1 (en) * | 2005-10-07 | 2013-07-31 | Exelixis, Inc. | PYRIDOPYRIMIDINONE INHIBITORS OF PI3Kalpha |
| US20090191193A1 (en) | 2006-08-02 | 2009-07-30 | Temple University-Of The Commonwealth System Of Higher Education | Aryl Vinyl Sulfides, Sulfones, Sulfoxides and Sulfonamides, Derivatives Thereof and Therapeutic Uses Thereof |
| EP2084159A1 (en) | 2006-10-16 | 2009-08-05 | GPC Biotech Inc. | Pyrido ý2, 3-d¨pyrimidines and their use as kinase inhibitors |
| WO2008150260A1 (en) | 2007-06-06 | 2008-12-11 | Gpc Biotech, Inc. | 8-oxy-2-aminopyrido (2, 3-d) pyrimidin-7-one derivatives as kinase inhibitors and anticancer agents |
| WO2011075616A1 (en) | 2009-12-18 | 2011-06-23 | Temple University - Of The Commonwealth System Of Higher Education | Substituted pyrido[2,3-d]pyrimidin-7(8h)-ones and therapeutic uses thereof |
| BR112013002375B1 (pt) * | 2010-08-05 | 2020-05-12 | Temple University - Of The Commonwealth System Of Higher Education | Composto, processo de preparação do mesmo, composição farmacêutica, e, usos de um composto |
-
2011
- 2011-07-21 BR BR112013002375-9A patent/BR112013002375B1/pt active IP Right Grant
- 2011-07-21 PT PT118150127T patent/PT2600719E/pt unknown
- 2011-07-21 MX MX2013001427A patent/MX2013001427A/es active IP Right Grant
- 2011-07-21 CA CA2807498A patent/CA2807498C/en active Active
- 2011-07-21 US US13/813,023 patent/US8987267B2/en active Active
- 2011-07-21 ES ES11815012.7T patent/ES2525866T3/es active Active
- 2011-07-21 DK DK11815012.7T patent/DK2600719T3/da active
- 2011-07-21 CN CN201180038325.3A patent/CN103200822B/zh active Active
- 2011-07-21 AU AU2011286282A patent/AU2011286282B2/en active Active
- 2011-07-21 EP EP11815012.7A patent/EP2600719B1/en active Active
- 2011-07-21 PL PL11815012T patent/PL2600719T3/pl unknown
- 2011-07-21 EA EA201390199A patent/EA022527B1/ru not_active IP Right Cessation
- 2011-07-21 JP JP2013523185A patent/JP5512894B2/ja active Active
- 2011-07-21 WO PCT/US2011/044807 patent/WO2012018540A1/en not_active Ceased
- 2011-07-21 NZ NZ606281A patent/NZ606281A/en unknown
- 2011-07-21 KR KR1020137004979A patent/KR101434841B1/ko active Active
-
2013
- 2013-02-03 IL IL224555A patent/IL224555A/en active IP Right Grant
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6498163B1 (en) * | 1997-02-05 | 2002-12-24 | Warner-Lambert Company | Pyrido[2,3-D]pyrimidines and 4-aminopyrimidines as inhibitors of cellular proliferation |
| CN1302301A (zh) * | 1998-05-26 | 2001-07-04 | 沃尼尔·朗伯公司 | 用作细胞增殖抑制剂的二环嘧啶及二环3,4-二氢嘧啶化合物 |
| CN1433417A (zh) * | 2000-01-27 | 2003-07-30 | 沃尼尔·朗伯公司 | 用于治疗神经变性疾病的吡啶并嘧啶酮衍生物 |
| US20010027196A1 (en) * | 2000-02-25 | 2001-10-04 | Borroni Edilio Maurizio | Adenosine receptor ligands and their use in the treatment of disease |
| CN1422268A (zh) * | 2000-03-06 | 2003-06-04 | 沃尼尔·朗伯公司 | 5-烷基吡啶并[2,3-d]嘧啶酪氨酸激酶抑制剂 |
| US20080004285A1 (en) * | 2004-12-30 | 2008-01-03 | De Jonghe Steven C A | Pyrido(3,2-d)pyrimidines and pharmaceutical compositions useful for medical treatment |
| US20090062274A1 (en) * | 2005-10-07 | 2009-03-05 | Exelixis, Inc | Pyridopyrimidinone inhibitors of pi3kalpha |
Non-Patent Citations (1)
| Title |
|---|
| synthesis and reactivity of 2,6-diamino-4-methyl-3-pyridinecabonitrile;Alan R.Katritzky etal;《Journal of heterocyclic chemistry》;19951231;第32卷(第3期);第1-18页,参见第第15页图解1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DK2600719T3 (da) | 2014-12-15 |
| US8987267B2 (en) | 2015-03-24 |
| US20130131058A1 (en) | 2013-05-23 |
| EP2600719B1 (en) | 2014-10-08 |
| EA022527B1 (ru) | 2016-01-29 |
| CA2807498A1 (en) | 2012-02-09 |
| EP2600719A1 (en) | 2013-06-12 |
| CN103200822A (zh) | 2013-07-10 |
| IL224555A (en) | 2016-03-31 |
| KR101434841B1 (ko) | 2014-08-29 |
| PL2600719T3 (pl) | 2015-03-31 |
| EP2600719A4 (en) | 2014-01-01 |
| PT2600719E (pt) | 2014-12-22 |
| EA201390199A1 (ru) | 2013-07-30 |
| AU2011286282B2 (en) | 2014-08-21 |
| NZ606281A (en) | 2014-09-26 |
| JP5512894B2 (ja) | 2014-06-04 |
| KR20130098314A (ko) | 2013-09-04 |
| WO2012018540A1 (en) | 2012-02-09 |
| BR112013002375A2 (pt) | 2016-05-24 |
| JP2013538196A (ja) | 2013-10-10 |
| MX2013001427A (es) | 2013-06-13 |
| BR112013002375B1 (pt) | 2020-05-12 |
| CA2807498C (en) | 2017-02-07 |
| AU2011286282A1 (en) | 2013-02-14 |
| ES2525866T3 (es) | 2014-12-30 |
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