AR090955A1 - Aminas biciclicas c-17 de triterpenoides con actividad inhibidora de la maduracion del vih - Google Patents
Aminas biciclicas c-17 de triterpenoides con actividad inhibidora de la maduracion del vihInfo
- Publication number
- AR090955A1 AR090955A1 ARP130101545A ARP130101545A AR090955A1 AR 090955 A1 AR090955 A1 AR 090955A1 AR P130101545 A ARP130101545 A AR P130101545A AR P130101545 A ARP130101545 A AR P130101545A AR 090955 A1 AR090955 A1 AR 090955A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- group
- coor2
- substituted
- nr2so2r3
- Prior art date
Links
- 230000035800 maturation Effects 0.000 title abstract 2
- 230000002401 inhibitory effect Effects 0.000 title 1
- 150000003648 triterpenes Chemical class 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 16
- 150000001875 compounds Chemical class 0.000 abstract 10
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 208000030507 AIDS Diseases 0.000 abstract 1
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- -1 bicyclic triterpenoid amines Chemical class 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 101150008563 spir gene Proteins 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
- C07D487/08—Bridged systems
-
- 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
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- 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
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
-
- 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
- C07D498/02—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 two hetero rings
- C07D498/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Oncology (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- AIDS & HIV (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Compuestos que tienen propiedades farmacológicas y que afectan el aspecto biológico, sus composiciones farmacéuticas y métodos de uso. En particular, las aminas bicíclicas C-17 de triterpenoides que tienen una actividad antiviral única se proveen como inhibidores de la maduración del VIH. Estos compuestos son útiles para el tratamiento del VIH y del SIDA. Reivindicación 1: Un compuesto, que incluye sales de este aceptables desde el punto de vista farmacéutico, caracterizado porque se selecciona del grupo de: un compuesto de la fórmula (1); un compuesto de la fórmula (2); y un compuesto de la fórmula (3); en donde R¹ es isopropenilo o isopropilo; J y E son, cada uno, independientemente -H o -CH₃, y E está ausente cuando el enlace doble está presente; X se selecciona del grupo de fenilo, anillo heteroarilo, anillo cicloalquilo C₄₋₈, cicloalquenilo C₄₋₈, spirocicloalquilo C₄₋₉, spirocicloalquenilo C₄₋₉, oxacicloalquilo C₄₋₈, dioxacicloalquilo C₄₋₈, oxacicloalquenilo C₆₋₈, dioxacicloalquenilo C₆₋₈, ciclodialquenilo C₆, oxaciclodialquenilo C₆, oxaspirocicloalquilo C₆₋₉ y oxaspirocicloalquenilo C₆₋₉; X también se puede seleccionar del grupo que consiste en los compuestos del grupo de fórmulas (4); y para los compuestos de las fórmulas (2) y (3), X también puede ser el compuesto de fórmula (5); en donde X se sustituye con A, y A es al menos un miembro seleccionado del grupo de -H, -halo, -hidroxilo, -alquilo C₁₋₆, -alcoxi C₁₋₆, -haloalquilo C₁₋₆, -NR²R², -COOR², -C(O)NR²R², -C(O)NR²SO₂R³, -SO₂NR²R², -NR²SO₂R², -SO₂NR²R², -cicloalquil C₁₋₆-COOR², -alquenil C₂₋₆-COOR², -alquinil C₂₋₆-COOR², -alquil C₁₋₆-COOR², -NHC(O)(CH₂)ₙ-COOR², -SO₂NR²C(O)R², -tetrazol y heteroaril-COOR² bicíclico; Y se selecciona del grupo de -COOR², -C(O)NR²SO₂R³, -C(O)NHSO₂NR²R², -NR²SO₂R³, -SO₂NR²R², -cicloalquil C₃₋₆-COOR², -alquenil C₂₋₆-COOR², -alquinil C₂₋₆-COOR², -alquil C₁₋₆-COOR², -NHC(O)(CH₂)ₙ-COOR², -SO₂NR²C(O)R², -tetrazol y -CONHOH; en donde n = 1 - 6; W es -CH₂ o -CO; Z se selecciona del grupo que consiste en los compuestos del grupo de fórmulas (6); V se selecciona del grupo de -CR⁸R⁹-, -SO₂-, -O- y -NR¹⁰-; U se selecciona del grupo de -CR⁸R⁹-, -SO₂- y -NR¹⁰-; M se selecciona del grupo de -CHR⁸R⁹, -SO₂R⁴, -SO₂NR³R³, -OH y -NR¹⁰R¹¹-; R² es -H, -alquilo C₁₋₆, alquilo C₁₋₆ sustituido con -alquilo o alquilo C₁₋₆ sustituido con -arilo; R³ es -alquilo C₁₋₆ o alquilo C₁₋₆ sustituido con -alquilo; R⁴ se selecciona del grupo de -alquilo C₁₋₆, alquilo C₁₋₆ sustituido con -alquilo, -cicloalquilo C₃₋₆, -arilo y -heteroarilo; R⁵ se selecciona del grupo de -H, -alquilo C₁₋₆, alquilo C₁₋₆ sustituido con -alquilo y -alquilo C₁₋₆-OH; R⁶ y R⁷ se seleccionan, cada uno, independientemente del grupo de -H, -alquilo C₁₋₆, alquilo C₁₋₆ sustituido con -alquilo, -CO₂R², -CH₂OH, -CHF₂ y -CF₃; R⁸ y R⁹ se seleccionan, cada uno, independientemente del grupo de -H, -alquilo C₁₋₆, alquilo C₁₋₆ sustituido con -alquilo, -SO₂R³, -SO₂NR²R² o -OH, -NR²R², -NR²SO₂R³, -NR²COR³ y -NR²CONR²R²; siempre que solo uno de R⁸ y R⁹ se puedan seleccionar del grupo de -OH, -NR²R², -NR²SO₂R³, -NR²COR³ y -NR²CONR²R²; y R¹⁰ y R¹¹ se seleccionan, cada uno, independientemente del grupo de -H, -alquilo C₁₋₆, alquilo C₁₋₆ sustituido con -alquilo, -alquil C₁₋₃arilo, alquil C₁₋₃heteroarilo, -CO₂R² y -SO₂R³; siempre que solo uno de R¹⁰ y R¹¹ se pueda seleccionar del grupo de -COR² o -SO₂R³.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261643483P | 2012-05-07 | 2012-05-07 | |
| US13/799,479 US8889854B2 (en) | 2012-05-07 | 2013-03-13 | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR090955A1 true AR090955A1 (es) | 2014-12-17 |
Family
ID=49513043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP130101545A AR090955A1 (es) | 2012-05-07 | 2013-05-06 | Aminas biciclicas c-17 de triterpenoides con actividad inhibidora de la maduracion del vih |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US8889854B2 (es) |
| EP (1) | EP2847208B1 (es) |
| JP (1) | JP6212545B2 (es) |
| KR (1) | KR20150013157A (es) |
| CN (1) | CN104540844B (es) |
| AR (1) | AR090955A1 (es) |
| AU (1) | AU2013259894B2 (es) |
| BR (1) | BR112014027669A2 (es) |
| CA (1) | CA2872891C (es) |
| EA (1) | EA027133B1 (es) |
| ES (1) | ES2652510T3 (es) |
| IL (1) | IL235465A (es) |
| MX (1) | MX354914B (es) |
| PT (1) | PT2847208T (es) |
| SG (1) | SG11201407189XA (es) |
| TW (1) | TWI574973B (es) |
| WO (1) | WO2013169578A1 (es) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8906889B2 (en) * | 2012-02-15 | 2014-12-09 | Bristol-Myers Squibb Company | C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity |
| JP6186010B2 (ja) | 2013-02-06 | 2017-08-23 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｈｉｖ成熟阻害活性を有するｃ−１９修飾トリテルペノイド類 |
| KR20150121712A (ko) | 2013-02-25 | 2015-10-29 | 브리스톨-마이어스 스큅 컴퍼니 | Hiv의 치료에 유용한 c-3 알킬 및 알케닐 개질된 베툴린산 유도체 |
| UY36070A (es) | 2014-04-11 | 2015-10-30 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Triterpenoides con actividad inhibidora de la maduración de hiv |
| WO2015195776A1 (en) | 2014-06-19 | 2015-12-23 | Bristol-Myers Squibb Company | Betulinic acid derivatives with hiv maturation inhibitory activity |
| EP3283467A1 (en) * | 2015-04-14 | 2018-02-21 | VIIV Healthcare UK(No.4) Limited | Methods of producing an hiv maturation inhibitor |
| WO2017017609A1 (en) | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| US20180194799A1 (en) | 2015-07-28 | 2018-07-12 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| KR20180054826A (ko) | 2015-09-24 | 2018-05-24 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | Hiv 성숙 억제 활성을 갖는 화합물 |
| EP3405474A1 (en) | 2016-01-20 | 2018-11-28 | Glaxosmithkline Intellectual Property (No. 2) Limited | Amine derivatives of lupanes with hiv maturation inhibitory activity |
| AR107512A1 (es) * | 2016-02-04 | 2018-05-09 | VIIV HEALTHCARE UK Nº 5 LTD | Triterpenoides modificados en c-3 y c-17 como inhibidores del vih-1 |
| IL273078B2 (en) | 2017-09-13 | 2025-06-01 | Emmyon Inc | Ursolic acid morpholine and diethanolamine salts |
| ES2970042T3 (es) | 2018-04-24 | 2024-05-24 | Viiv Healthcare Uk No 5 Ltd | Compuestos con actividad inhibidora de la maduración del VIH |
| CN109705189B (zh) * | 2018-12-29 | 2020-06-05 | 中国医学科学院药用植物研究所 | 具有式i所示结构的三萜衍生物及其制备方法和应用 |
| AU2020222299C1 (en) * | 2019-02-11 | 2024-05-16 | Hetero Labs Limited | Novel triterpene derivatives as HIV inhibitors |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
| US5962527A (en) | 1995-03-21 | 1999-10-05 | The Board Of Trustees Of The University Of Illinois | Method and composition for treating cancers |
| US5869535A (en) | 1995-03-21 | 1999-02-09 | The Board Of Trustees Of The University Of Illinois | Method and composition for selectively inhibiting melanoma |
| US5679828A (en) | 1995-06-05 | 1997-10-21 | Biotech Research Labs, Inc. | Betulinic acid and dihydrobetulinic acid derivatives and uses therefor |
| US20040110785A1 (en) | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| WO2004014881A2 (en) | 2002-08-09 | 2004-02-19 | Astra Zeneca Ab | '1,2,4'oxadiazoles as modulators of metabotropic glutamate receptor-5 |
| US7365221B2 (en) | 2002-09-26 | 2008-04-29 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| WO2004089357A2 (en) | 2003-04-02 | 2004-10-21 | Regents Of The University Of Minnesota | Anti-fungal formulation of triterpene and essential oil |
| US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
| BRPI0508854A (pt) | 2004-03-17 | 2007-08-28 | Panacos Pharmaceuticals Inc | sais farmacêuticos de ácido-3-o-(3',3'-dimetilsuccinil) betulìnico |
| CN101142227A (zh) * | 2004-11-12 | 2008-03-12 | 帕纳克斯医药公司 | 新颖的桦木醇衍生物、其制备和其用途 |
| TW200628161A (en) | 2004-11-12 | 2006-08-16 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
| WO2008127364A2 (en) | 2006-10-13 | 2008-10-23 | Myriad Genetics, Inc. | Antiviral compounds and use thereof |
| WO2008115281A2 (en) | 2006-10-16 | 2008-09-25 | Myriad Genetics, Inc. | Compounds for treating viral infections |
| CA2714049A1 (en) | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | Novel 17.beta. lupane derivatives |
| US9067966B2 (en) | 2009-07-14 | 2015-06-30 | Hetero Research Foundation, Hetero Drugs Ltd. | Lupeol-type triterpene derivatives as antivirals |
| KR101445012B1 (ko) | 2009-12-17 | 2014-09-26 | 머크 샤프 앤드 돔 코포레이션 | Ｓｙｋ 억제제로서의 아미노피리미딘 |
| RS54239B1 (sr) | 2010-06-04 | 2015-12-31 | Bristol-Myers Squibb Company | C-28 amidi modifikovanih derivata c-3 betulinske kiseline kao inhibitori sazrevanja hiv-a |
| US8754068B2 (en) | 2010-06-04 | 2014-06-17 | Bristol-Myers Squibb Company | Modified C-3 betulinic acid derivatives as HIV maturation inhibitors |
| MX2012015097A (es) | 2010-07-02 | 2013-05-28 | Gilead Sciences Inc | Derivados de acido naft-2-ilacetico para tratar sida. |
| HUE026371T2 (en) * | 2011-01-31 | 2016-05-30 | Bristol Myers Squibb Co | C-28 amines from modified C-3 betulinic acid derivatives as anti-HIV matrices |
| US8846647B2 (en) * | 2011-01-31 | 2014-09-30 | Bristol-Myers Squibb Company | C-17 and C-3 modified triterpenoids with HIV maturation inhibitory activity |
| MX2014002936A (es) | 2011-09-21 | 2014-04-25 | Bristol Myers Squibb Co | Nuevos derivados de acido betulinico con actividad antiviral. |
| US8906889B2 (en) | 2012-02-15 | 2014-12-09 | Bristol-Myers Squibb Company | C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity |
-
2013
- 2013-03-13 US US13/799,479 patent/US8889854B2/en active Active
- 2013-05-03 PT PT137229472T patent/PT2847208T/pt unknown
- 2013-05-03 ES ES13722947.2T patent/ES2652510T3/es active Active
- 2013-05-03 SG SG11201407189XA patent/SG11201407189XA/en unknown
- 2013-05-03 AU AU2013259894A patent/AU2013259894B2/en not_active Ceased
- 2013-05-03 BR BR112014027669A patent/BR112014027669A2/pt not_active Application Discontinuation
- 2013-05-03 MX MX2014013089A patent/MX354914B/es active IP Right Grant
- 2013-05-03 JP JP2015511548A patent/JP6212545B2/ja active Active
- 2013-05-03 CA CA2872891A patent/CA2872891C/en not_active Expired - Fee Related
- 2013-05-03 WO PCT/US2013/039389 patent/WO2013169578A1/en not_active Ceased
- 2013-05-03 KR KR1020147031255A patent/KR20150013157A/ko not_active Ceased
- 2013-05-03 EA EA201492016A patent/EA027133B1/ru not_active IP Right Cessation
- 2013-05-03 EP EP13722947.2A patent/EP2847208B1/en active Active
- 2013-05-03 CN CN201380023798.5A patent/CN104540844B/zh not_active Expired - Fee Related
- 2013-05-06 AR ARP130101545A patent/AR090955A1/es unknown
- 2013-05-06 TW TW102116106A patent/TWI574973B/zh not_active IP Right Cessation
-
2014
- 2014-11-03 IL IL235465A patent/IL235465A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TWI574973B (zh) | 2017-03-21 |
| JP6212545B2 (ja) | 2017-10-11 |
| PT2847208T (pt) | 2017-12-14 |
| EP2847208A1 (en) | 2015-03-18 |
| MX2014013089A (es) | 2014-12-08 |
| US20130296554A1 (en) | 2013-11-07 |
| MX354914B (es) | 2018-03-26 |
| WO2013169578A1 (en) | 2013-11-14 |
| CA2872891C (en) | 2018-10-23 |
| EA027133B1 (ru) | 2017-06-30 |
| TW201350499A (zh) | 2013-12-16 |
| IL235465A (en) | 2015-11-30 |
| CN104540844A (zh) | 2015-04-22 |
| EP2847208B1 (en) | 2017-10-04 |
| AU2013259894B2 (en) | 2017-07-13 |
| AU2013259894A1 (en) | 2015-01-15 |
| CN104540844B (zh) | 2016-12-07 |
| CA2872891A1 (en) | 2013-11-14 |
| SG11201407189XA (en) | 2014-12-30 |
| US8889854B2 (en) | 2014-11-18 |
| KR20150013157A (ko) | 2015-02-04 |
| BR112014027669A2 (pt) | 2017-06-27 |
| EA201492016A1 (ru) | 2015-02-27 |
| ES2652510T3 (es) | 2018-02-02 |
| JP2015516422A (ja) | 2015-06-11 |
Similar Documents
| Publication | Publication Date | Title |
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