CA2844388A1 - Process and intermediates for preparing macrolactams - Google Patents
Process and intermediates for preparing macrolactams Download PDFInfo
- Publication number
- CA2844388A1 CA2844388A1 CA2844388A CA2844388A CA2844388A1 CA 2844388 A1 CA2844388 A1 CA 2844388A1 CA 2844388 A CA2844388 A CA 2844388A CA 2844388 A CA2844388 A CA 2844388A CA 2844388 A1 CA2844388 A1 CA 2844388A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- salt
- compounds
- added
- making
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/04—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a three or four-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C271/34—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/013—Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
- C07K5/126—Tetrapeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161525462P | 2011-08-19 | 2011-08-19 | |
| US61/525,462 | 2011-08-19 | ||
| US201161533439P | 2011-09-12 | 2011-09-12 | |
| US61/533,439 | 2011-09-12 | ||
| US201161533915P | 2011-09-13 | 2011-09-13 | |
| US61/533,915 | 2011-09-13 | ||
| US201161539540P | 2011-09-27 | 2011-09-27 | |
| US61/539,540 | 2011-09-27 | ||
| PCT/US2012/051177 WO2013028470A1 (en) | 2011-08-19 | 2012-08-16 | Process and intermediates for preparing macrolactams |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2844388A1 true CA2844388A1 (en) | 2013-02-28 |
Family
ID=47746773
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2844388A Abandoned CA2844388A1 (en) | 2011-08-19 | 2012-08-16 | Process and intermediates for preparing macrolactams |
| CA2844386A Abandoned CA2844386A1 (en) | 2011-08-19 | 2012-08-16 | Crystal forms of a hcv protease inhibitor |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2844386A Abandoned CA2844386A1 (en) | 2011-08-19 | 2012-08-16 | Crystal forms of a hcv protease inhibitor |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US9238604B2 (enExample) |
| EP (3) | EP2744331A4 (enExample) |
| JP (2) | JP2014521750A (enExample) |
| KR (2) | KR20140053330A (enExample) |
| CN (2) | CN103874414A (enExample) |
| AU (2) | AU2012299218A1 (enExample) |
| BR (2) | BR112014003802A2 (enExample) |
| CA (2) | CA2844388A1 (enExample) |
| MX (2) | MX2014001945A (enExample) |
| RU (2) | RU2014110399A (enExample) |
| WO (3) | WO2013028470A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011014487A1 (en) | 2009-07-30 | 2011-02-03 | Merck Sharp & Dohme Corp. | Hepatitis c virus ns3 protease inhibitors |
| US8957203B2 (en) | 2011-05-05 | 2015-02-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| EP2744331A4 (en) | 2011-08-19 | 2015-01-21 | Merck Sharp & Dohme | METHOD AND INTERMEDIATE PRODUCTS FOR THE MANUFACTURE OF MACROLACTAMEN |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| BR112015007879A2 (pt) | 2012-10-19 | 2017-07-04 | Bristol Myers Squibb Co | inibidores do vírus da hepatite c |
| WO2014070964A1 (en) | 2012-11-02 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US9334279B2 (en) | 2012-11-02 | 2016-05-10 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2014070974A1 (en) | 2012-11-05 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EP2764866A1 (en) | 2013-02-07 | 2014-08-13 | IP Gesellschaft für Management mbH | Inhibitors of nedd8-activating enzyme |
| US9580463B2 (en) | 2013-03-07 | 2017-02-28 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| MX2015013224A (es) | 2013-03-15 | 2015-12-11 | Gilead Sciences Inc | Inhibidores macrociclicos y biciclicos del virus de la hepatitis c. |
| US9873707B2 (en) | 2013-10-18 | 2018-01-23 | Merck Sharp & Dohme Corp. | Methods and intermediates for preparing macrolactams |
| WO2015095437A1 (en) * | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | Methods and intermediates for the preparation of macrolactams |
| DK3636649T3 (da) * | 2014-01-24 | 2024-05-21 | Turning Point Therapeutics Inc | Diarylmakrocykler som modulatorer af proteinkinaser |
| AU2015269306B2 (en) * | 2014-06-06 | 2020-06-25 | Abbvie Inc. | Crystal forms |
| EP3317285B1 (en) | 2015-07-02 | 2021-01-27 | Turning Point Therapeutics, Inc. | Chiral diaryl macrocycles as modulators of protein kinases |
| WO2017007759A1 (en) * | 2015-07-06 | 2017-01-12 | Tp Therapeutics, Inc. | Diaryl macrocycle polymorph |
| DK3733187T3 (da) * | 2015-07-21 | 2025-01-02 | Turning Point Therapeutics Inc | Chiral diarylmakrocyklus og anvendelse deraf i behandling af cancer |
| EP3454856B1 (en) | 2016-05-10 | 2024-09-11 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| CN109641874A (zh) | 2016-05-10 | 2019-04-16 | C4医药公司 | 用于靶蛋白降解的c3-碳连接的戊二酰亚胺降解决定子体 |
| ES2990061T3 (es) | 2016-05-10 | 2024-11-28 | C4 Therapeutics Inc | Degronímeros espirocíclicos para la degradación de proteínas diana |
| WO2017197051A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Amine-linked c3-glutarimide degronimers for target protein degradation |
| US10689400B2 (en) | 2016-07-28 | 2020-06-23 | Turning Point Therapeutics, Inc. | Macrocycle kinase inhibitors |
| TWI808958B (zh) | 2017-01-25 | 2023-07-21 | 美商特普醫葯公司 | 涉及二芳基巨環化合物之組合療法 |
| EP3641762A4 (en) | 2017-06-20 | 2021-03-10 | C4 Therapeutics, Inc. | N / O-LINKED DEGRONES AND DEGRONIMERS FOR PROTEIN DEGRADATION |
| JP7224334B2 (ja) | 2017-07-28 | 2023-02-17 | ターニング・ポイント・セラピューティクス・インコーポレイテッド | 大環式化合物およびその使用 |
| PT3728271T (pt) | 2017-12-19 | 2022-10-06 | Turning Point Therapeutics Inc | Compostos macrocíclicos para tratar doenças |
| CN111057045A (zh) * | 2019-12-18 | 2020-04-24 | 安徽红杉生物医药科技有限公司 | Hcv ns3/4a蛋白酶抑制剂中间体及其合成方法、应用 |
| CN112174982A (zh) * | 2020-09-10 | 2021-01-05 | 上海希迈医药科技有限公司 | 一种洛普替尼晶型及其制备方法 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4871868A (en) | 1987-03-11 | 1989-10-03 | Takeda Chemical Industries, Ltd. | Production of substituted acetylenic compounds |
| GB9207987D0 (en) | 1992-04-10 | 1992-05-27 | Smithkline Beecham Plc | Novel container and closure |
| US5716960A (en) * | 1995-01-13 | 1998-02-10 | U.S. Bioscience Inc. And Individuals | Crystalline trimetrexate salts and the process for making the same |
| ZA98879B (en) * | 1997-02-04 | 1998-08-03 | Ono Pharmaceutical Co | Omega-cycloalkyl-prostaglandin e2 derivatives |
| NO317155B1 (no) | 1997-02-04 | 2004-08-30 | Ono Pharmaceutical Co | <omega>-cykloalkyl-prostagladin-E<N>2</N>-derivater |
| KR20130076903A (ko) * | 2005-02-18 | 2013-07-08 | 미쓰비시 타나베 파마 코퍼레이션 | 프롤린 유도체의 염 또는 그 용매화물 및 그 제조 방법 |
| US7834145B2 (en) | 2005-03-22 | 2010-11-16 | Merck Sharp & Dohme Corp. | HCV protease substrates |
| AU2006242475B2 (en) | 2005-05-02 | 2011-07-07 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| AR057456A1 (es) | 2005-07-20 | 2007-12-05 | Merck & Co Inc | Inhibidores de la proteasa ns3 del vhc |
| CN101228181B (zh) * | 2005-07-20 | 2013-09-18 | 默沙东公司 | Hcv ns3蛋白酶抑制剂 |
| US8278322B2 (en) | 2005-08-01 | 2012-10-02 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| MX2008011079A (es) | 2006-03-07 | 2008-09-05 | Procter & Gamble | Composiciones para teñir oxidativamente fibras de queratina y metodos p ara utilizar tales composiciones. |
| GB0609492D0 (en) | 2006-05-15 | 2006-06-21 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| GB0612423D0 (en) | 2006-06-23 | 2006-08-02 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| US8309540B2 (en) | 2006-10-24 | 2012-11-13 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| WO2008051477A2 (en) | 2006-10-24 | 2008-05-02 | Merck & Co., Inc. | Hcv ns3 protease inhibitors |
| US8377874B2 (en) | 2006-10-27 | 2013-02-19 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| JP5268927B2 (ja) | 2006-10-27 | 2013-08-21 | メルク・シャープ・アンド・ドーム・コーポレーション | Ｈｃｖｎｓ３プロテアーゼ阻害剤 |
| BRPI0811020A2 (pt) | 2007-05-03 | 2015-07-21 | Intermune Inc | Composto, composição farmacêutica e métodos de inibição da atividade da protease ns3/ns4, de tratamento da fibrose hepática, de intensificação da função hepática em indivíduo com infecção do vírus da hepatite c e métodos de síntese de compostos, de administração de inibidor da infecção do vírus da hepatite c (hcv) e de distribuição de forma de dosagem oral. |
| US8927569B2 (en) | 2007-07-19 | 2015-01-06 | Merck Sharp & Dohme Corp. | Macrocyclic compounds as antiviral agents |
| CA2714604A1 (en) | 2008-02-25 | 2009-09-03 | Merck Sharp & Dohme Corp. | Macrocyclic hcv ns3 protease inhibitors |
| WO2009131196A1 (ja) * | 2008-04-24 | 2009-10-29 | 武田薬品工業株式会社 | 置換ピロリジン誘導体およびその用途 |
| JP2011518836A (ja) * | 2008-04-24 | 2011-06-30 | インサイト・コーポレイション | 大環状化合物およびそれらのキナーゼ阻害剤としての使用 |
| JP2011518882A (ja) | 2008-04-28 | 2011-06-30 | メルク・シャープ・エンド・ドーム・コーポレイション | Ｈｃｖｎｓ３プロテアーゼ阻害剤 |
| PE20110212A1 (es) * | 2008-07-22 | 2011-04-10 | Merck Sharp & Dohme | (1aR, 5S, 8S, 10R, 22aR)-5-TERT-BUTIL-N-{(1R, 2S)-1-{[(CICLOPROPILSULFONIL) AMINO] CARBONIL}-2-VINILCICLOPROPIL}-14-METOXI-3,6-DIOXO-1, 1a, 3, 4, 5, 6, 9, 10, 18, 19, 20, 21, 22, 22a-TETRADECAHIDRO-8H-7, 10-METANOCICLOPROPA[18, 19] [1, 10, 3, 6] DIOXADIAZACICLONONADECINO[11, 12-b] QUINOXALIN-8-CARBOXAMIDA COMO INHIBIDOR DE LA PROTEASA HCV NS3 |
| WO2011014487A1 (en) | 2009-07-30 | 2011-02-03 | Merck Sharp & Dohme Corp. | Hepatitis c virus ns3 protease inhibitors |
| EP2470189A4 (en) * | 2009-08-27 | 2013-01-23 | Merck Sharp & Dohme | METHOD FOR PRODUCING PROTEASE INHIBITORS OF HEPATITIS C VIRUS |
| EP2744331A4 (en) | 2011-08-19 | 2015-01-21 | Merck Sharp & Dohme | METHOD AND INTERMEDIATE PRODUCTS FOR THE MANUFACTURE OF MACROLACTAMEN |
-
2012
- 2012-08-16 EP EP12825726.8A patent/EP2744331A4/en not_active Withdrawn
- 2012-08-16 JP JP2014526217A patent/JP2014521750A/ja active Pending
- 2012-08-16 WO PCT/US2012/051177 patent/WO2013028470A1/en not_active Ceased
- 2012-08-16 CN CN201280050361.6A patent/CN103874414A/zh active Pending
- 2012-08-16 KR KR1020147006858A patent/KR20140053330A/ko not_active Withdrawn
- 2012-08-16 AU AU2012299218A patent/AU2012299218A1/en not_active Abandoned
- 2012-08-16 MX MX2014001945A patent/MX2014001945A/es unknown
- 2012-08-16 RU RU2014110399/04A patent/RU2014110399A/ru not_active Application Discontinuation
- 2012-08-16 BR BR112014003802A patent/BR112014003802A2/pt not_active IP Right Cessation
- 2012-08-16 KR KR1020147006888A patent/KR20140059236A/ko not_active Withdrawn
- 2012-08-16 CN CN201280050382.8A patent/CN103889439A/zh active Pending
- 2012-08-16 WO PCT/US2012/051182 patent/WO2013028471A1/en not_active Ceased
- 2012-08-16 JP JP2014526215A patent/JP2014524442A/ja active Pending
- 2012-08-16 US US14/239,393 patent/US9238604B2/en active Active
- 2012-08-16 BR BR112014003798A patent/BR112014003798A2/pt not_active IP Right Cessation
- 2012-08-16 US US14/239,389 patent/US9242917B2/en active Active
- 2012-08-16 CA CA2844388A patent/CA2844388A1/en not_active Abandoned
- 2012-08-16 US US14/239,391 patent/US9073825B2/en active Active
- 2012-08-16 MX MX2014001944A patent/MX2014001944A/es unknown
- 2012-08-16 EP EP12825540.3A patent/EP2744507A4/en not_active Withdrawn
- 2012-08-16 CA CA2844386A patent/CA2844386A1/en not_active Abandoned
- 2012-08-16 EP EP12826404.1A patent/EP2744336B1/en not_active Not-in-force
- 2012-08-16 AU AU2012299223A patent/AU2012299223A1/en not_active Abandoned
- 2012-08-16 RU RU2014110400/04A patent/RU2014110400A/ru not_active Application Discontinuation
- 2012-08-16 WO PCT/US2012/051168 patent/WO2013028465A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP2744331A1 (en) | 2014-06-25 |
| KR20140053330A (ko) | 2014-05-07 |
| AU2012299223A1 (en) | 2014-02-27 |
| CA2844386A1 (en) | 2013-02-28 |
| CN103889439A (zh) | 2014-06-25 |
| KR20140059236A (ko) | 2014-05-15 |
| EP2744507A1 (en) | 2014-06-25 |
| EP2744336A1 (en) | 2014-06-25 |
| US9242917B2 (en) | 2016-01-26 |
| US9238604B2 (en) | 2016-01-19 |
| EP2744336A4 (en) | 2014-12-31 |
| JP2014524442A (ja) | 2014-09-22 |
| US9073825B2 (en) | 2015-07-07 |
| CN103874414A (zh) | 2014-06-18 |
| RU2014110400A (ru) | 2015-09-27 |
| BR112014003802A2 (pt) | 2017-06-13 |
| WO2013028471A1 (en) | 2013-02-28 |
| JP2014521750A (ja) | 2014-08-28 |
| WO2013028470A1 (en) | 2013-02-28 |
| US20140243519A1 (en) | 2014-08-28 |
| BR112014003798A2 (pt) | 2017-03-01 |
| US20140200343A1 (en) | 2014-07-17 |
| US20140206605A1 (en) | 2014-07-24 |
| EP2744336B1 (en) | 2017-07-05 |
| EP2744507A4 (en) | 2015-01-28 |
| EP2744331A4 (en) | 2015-01-21 |
| MX2014001944A (es) | 2014-03-27 |
| AU2012299218A1 (en) | 2014-02-20 |
| MX2014001945A (es) | 2014-03-27 |
| RU2014110399A (ru) | 2015-09-27 |
| WO2013028465A1 (en) | 2013-02-28 |
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