IN2014DN09234A - - Google Patents
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- Publication number
- IN2014DN09234A IN2014DN09234A IN9234DEN2014A IN2014DN09234A IN 2014DN09234 A IN2014DN09234 A IN 2014DN09234A IN 9234DEN2014 A IN9234DEN2014 A IN 9234DEN2014A IN 2014DN09234 A IN2014DN09234 A IN 2014DN09234A
- Authority
- IN
- India
- Prior art keywords
- germanium
- acid
- derivative
- producing
- water
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 abstract 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract 3
- 229910052732 germanium Inorganic materials 0.000 abstract 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 abstract 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 2
- 150000001413 amino acids Chemical class 0.000 abstract 2
- 230000000840 anti-viral effect Effects 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 abstract 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- 150000003212 purines Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 abstract 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical class NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004475 Arginine Substances 0.000 abstract 1
- 239000004471 Glycine Substances 0.000 abstract 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 abstract 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 abstract 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 abstract 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004472 Lysine Substances 0.000 abstract 1
- JNTOCHDNEULJHD-UHFFFAOYSA-N Penciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(CCC(CO)CO)C=N2 JNTOCHDNEULJHD-UHFFFAOYSA-N 0.000 abstract 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004473 Threonine Substances 0.000 abstract 1
- HDOVUKNUBWVHOX-QMMMGPOBSA-N Valacyclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 HDOVUKNUBWVHOX-QMMMGPOBSA-N 0.000 abstract 1
- OIRDTQYFTABQOQ-UHTZMRCNSA-N Vidarabine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O OIRDTQYFTABQOQ-UHTZMRCNSA-N 0.000 abstract 1
- 229960004150 aciclovir Drugs 0.000 abstract 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 abstract 1
- 235000015165 citric acid Nutrition 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229960002963 ganciclovir Drugs 0.000 abstract 1
- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 abstract 1
- 229940119177 germanium dioxide Drugs 0.000 abstract 1
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000004310 lactic acid Substances 0.000 abstract 1
- 235000014655 lactic acid Nutrition 0.000 abstract 1
- 239000001630 malic acid Substances 0.000 abstract 1
- 235000011090 malic acid Nutrition 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229960001179 penciclovir Drugs 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 238000011282 treatment Methods 0.000 abstract 1
- 241001529453 unidentified herpesvirus Species 0.000 abstract 1
- 229940093257 valacyclovir Drugs 0.000 abstract 1
- 229960003636 vidarabine Drugs 0.000 abstract 1
- 230000003612 virological effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12
-
- 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
- A61K31/28—Compounds containing heavy metals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/52—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an inorganic compound, e.g. an inorganic ion that is complexed with the active ingredient
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/542—Carboxylic acids, e.g. a fatty acid or an amino acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/547—Chelates, e.g. Gd-DOTA or Zinc-amino acid chelates; Chelate-forming compounds, e.g. DOTA or ethylenediamine being covalently linked or complexed to the pharmacologically- or therapeutically-active agent
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/30—Germanium compounds
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Inorganic Chemistry (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
The invention relates to the development of drugs intended for the prophylaxis and/or treatment of viral diseases caused, in particular, by herpes viruses. What are proposed are complex compounds of germanium having the general structural formula: Gex [AD][CA]y[AA]z (I), where AD is a derivative of a nitrogenous base of the purine series that has antiviral activity and can be selected from guanine derivatives, such as aciclovir, valaciclovir, ganciclovir and penciclovir, or from adenine derivatives, such as vidarabine; CA is a hydroxycarboxylic acid which can be selected from acids such as (but not limited to) citric acid, lactic acid and malic acid; AA is an amino acid which can be selected from various a-amino acids, such as arginine, glycine, lysine and threonine, and where x = 1-2, у = 2-4 and z = 0-2. Complex compounds of germanium have a high level of antiviral and immune-stimulating activity and are readily soluble in water. The above-mentioned compounds are produced by producing an aqueous suspension of germanium dioxide, adding a hydroxycarboxylic acid, a derivative of a nitrogenous base of the purine series and, optionally, but prefer - ably, an amino acid thereto, heating the mixture produced at a temperature of 40-100°C for 3-14 hours while stirring and removing the water from the solution, thus producing a complex compound of germanium.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2012120329/04A RU2487878C1 (en) | 2012-05-16 | 2012-05-16 | Complexes of germanium with purine nitrogenous bases, methods for production thereof and medicinal agents containing said complexes |
| PCT/RU2012/000897 WO2013172732A1 (en) | 2012-05-16 | 2012-11-01 | Complex compounds of germanium, methods for producing same, and drugs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IN2014DN09234A true IN2014DN09234A (en) | 2015-07-10 |
Family
ID=48791166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IN9234DEN2014 IN2014DN09234A (en) | 2012-05-16 | 2012-11-01 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US9745337B2 (en) |
| EP (1) | EP2851368B1 (en) |
| JP (1) | JP5993088B2 (en) |
| KR (1) | KR101717280B1 (en) |
| CN (1) | CN104302651B (en) |
| AU (1) | AU2012380376B2 (en) |
| BR (1) | BR112014027919B1 (en) |
| CA (1) | CA2873390C (en) |
| DK (1) | DK2851368T3 (en) |
| ES (1) | ES2710915T3 (en) |
| IN (1) | IN2014DN09234A (en) |
| PL (1) | PL2851368T3 (en) |
| PT (1) | PT2851368T (en) |
| RU (1) | RU2487878C1 (en) |
| TR (1) | TR201901561T4 (en) |
| WO (1) | WO2013172732A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2626954C2 (en) * | 2015-11-11 | 2017-08-02 | Общество С Ограниченной Ответственностью "Вдс Фарма" | Complex germanium connections with amino acids and lipoic acid |
| RU2752934C1 (en) * | 2020-10-16 | 2021-08-11 | Александр Дмитриевич Исаев | Complex compounds of germanium with acyclic polyols and method for synthesis thereof |
| CN114133398B (en) * | 2021-12-31 | 2022-11-22 | 中南民族大学 | Amino acid substituted acyclovir tricyclic nucleoside derivative and synthesis method and application thereof |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3616208A (en) * | 1967-09-29 | 1971-10-26 | Parke Davis & Co | Fermentation process for 9-(beta-d-arabinofuranosyl)adenine |
| JPS4924213B1 (en) * | 1969-04-02 | 1974-06-21 | ||
| JPS4924213A (en) | 1972-06-19 | 1974-03-04 | ||
| DE3212817A1 (en) * | 1982-04-06 | 1983-10-13 | Sanum-Kehlbeck GmbH & Co KG, 2812 Hoya | PHARMACEUTICALLY EFFECTIVE ORGANIC GERMANIUM COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF |
| EP0477871A3 (en) | 1990-09-28 | 1992-12-02 | Nippon Kayaku Kabushiki Kaisha | Antiviral composition, containing guanine derivatives |
| CN1154359A (en) | 1996-01-12 | 1997-07-16 | 常达正 | Method for prepn. and application of germanium amino-acidic |
| EP0931084B1 (en) | 1996-09-05 | 2002-02-06 | Primamedic Limited | 1,3-dicarboxylic germanium complex and its therapeutic use |
| RU2104032C1 (en) * | 1997-03-11 | 1998-02-10 | Общество с ограниченной ответственностью "Снежный барс" | Method of potentiation of medicinal agent curative effect |
| RU2233286C2 (en) * | 1998-08-17 | 2004-07-27 | Евгений Владимирович Соловьев | Germanium biochemical complexes with high therapeutic activity and broad spectrum applying |
| ES2185576T3 (en) | 1999-02-22 | 2003-05-01 | Gernot Treusch | MIXTURE OF THERAPEUTIC ACTION SUBSTANCES CONTAINING S-ACETILGLUTATION AND ACICLOVIR. |
| RU2240792C2 (en) | 2002-07-30 | 2004-11-27 | Государственное учреждение Научно-исследовательский институт вирусологии им. Д.И. Ивановского РАМН | Combinations based on netropsin or its bis-derivative eliciting anti-herpetic activity |
| RU2233280C1 (en) | 2003-03-25 | 2004-07-27 | Научно-исследовательский институт физической и органической химии Ростовского государственного университета | 10-ω-ARYLOXYALKYL-2,3,4,10-TETRAHYDROPYRIMIDO[1,2-A]BENZIMIDAZOLE SALTS ELICITING TOPICALLY ANESTHETIC EFFECT |
| DE10343365A1 (en) | 2003-09-17 | 2005-04-14 | Biosphings Ag | Pharmaceutical Formulations of Xanthogenates and Inhibitors of Viral Nucleic Acid Replication |
| RU2476436C1 (en) * | 2012-01-25 | 2013-02-27 | Общество С Ограниченной Ответственностью "Вдс Фарма" | Complex compounds of germanium with amino acids and carbocylic acids |
-
2012
- 2012-05-16 RU RU2012120329/04A patent/RU2487878C1/en active
- 2012-11-01 PL PL12876796T patent/PL2851368T3/en unknown
- 2012-11-01 EP EP12876796.9A patent/EP2851368B1/en active Active
- 2012-11-01 AU AU2012380376A patent/AU2012380376B2/en not_active Ceased
- 2012-11-01 ES ES12876796T patent/ES2710915T3/en active Active
- 2012-11-01 IN IN9234DEN2014 patent/IN2014DN09234A/en unknown
- 2012-11-01 PT PT12876796T patent/PT2851368T/en unknown
- 2012-11-01 KR KR1020147035216A patent/KR101717280B1/en active IP Right Grant
- 2012-11-01 CN CN201280073187.7A patent/CN104302651B/en active Active
- 2012-11-01 DK DK12876796.9T patent/DK2851368T3/en active
- 2012-11-01 US US14/400,081 patent/US9745337B2/en active Active
- 2012-11-01 JP JP2015512600A patent/JP5993088B2/en active Active
- 2012-11-01 WO PCT/RU2012/000897 patent/WO2013172732A1/en active Application Filing
- 2012-11-01 BR BR112014027919A patent/BR112014027919B1/en active IP Right Grant
- 2012-11-01 TR TR2019/01561T patent/TR201901561T4/en unknown
- 2012-11-01 CA CA2873390A patent/CA2873390C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2851368A1 (en) | 2015-03-25 |
| PL2851368T3 (en) | 2019-06-28 |
| CN104302651A (en) | 2015-01-21 |
| CA2873390C (en) | 2017-10-24 |
| CN104302651B (en) | 2017-04-12 |
| JP5993088B2 (en) | 2016-09-14 |
| EP2851368A4 (en) | 2016-02-10 |
| RU2487878C1 (en) | 2013-07-20 |
| EP2851368B1 (en) | 2019-01-02 |
| BR112014027919B1 (en) | 2020-02-04 |
| CA2873390A1 (en) | 2013-11-21 |
| KR101717280B1 (en) | 2017-03-17 |
| ES2710915T3 (en) | 2019-04-29 |
| AU2012380376A1 (en) | 2014-12-04 |
| US9745337B2 (en) | 2017-08-29 |
| DK2851368T3 (en) | 2019-02-25 |
| BR112014027919A2 (en) | 2017-06-27 |
| PT2851368T (en) | 2019-02-11 |
| AU2012380376B2 (en) | 2015-10-01 |
| WO2013172732A1 (en) | 2013-11-21 |
| KR20150011386A (en) | 2015-01-30 |
| US20150126726A1 (en) | 2015-05-07 |
| TR201901561T4 (en) | 2019-02-21 |
| JP2015518823A (en) | 2015-07-06 |
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