AU2013396752B2 - Method for manufacturing a shaped cross-linked hyaluronic acid product - Google Patents
Method for manufacturing a shaped cross-linked hyaluronic acid product Download PDFInfo
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- AU2013396752B2 AU2013396752B2 AU2013396752A AU2013396752A AU2013396752B2 AU 2013396752 B2 AU2013396752 B2 AU 2013396752B2 AU 2013396752 A AU2013396752 A AU 2013396752A AU 2013396752 A AU2013396752 A AU 2013396752A AU 2013396752 B2 AU2013396752 B2 AU 2013396752B2
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- Prior art keywords
- cross
- hyaluronic acid
- linked
- gel
- linking
- Prior art date
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- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 title claims abstract description 444
- 229920002674 hyaluronan Polymers 0.000 title claims abstract description 440
- 229960003160 hyaluronic acid Drugs 0.000 title claims abstract description 436
- 238000000034 method Methods 0.000 title claims abstract description 135
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 93
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- 239000000243 solution Substances 0.000 claims description 64
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 claims description 47
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- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims description 6
- HEGWNIMGIDYRAU-UHFFFAOYSA-N 3-hexyl-2,4-dioxabicyclo[1.1.0]butane Chemical compound O1C2OC21CCCCCC HEGWNIMGIDYRAU-UHFFFAOYSA-N 0.000 claims description 6
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- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 5
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- GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 claims 1
- 229960004399 carbocisteine Drugs 0.000 claims 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 1
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- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical class CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 description 62
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- 108010003272 Hyaluronate lyase Proteins 0.000 description 8
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 6
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
- A61K31/728—Hyaluronic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/042—Gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F9/00—Artificial filaments or the like of other substances; Manufacture thereof; Apparatus specially adapted for the manufacture of carbon filaments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/91—Injection
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Birds (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Dispersion Chemistry (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Biomedical Technology (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Materials For Medical Uses (AREA)
- Medicinal Preparation (AREA)
- Heart & Thoracic Surgery (AREA)
- Surgery (AREA)
- Vascular Medicine (AREA)
- Inorganic Chemistry (AREA)
Applications Claiming Priority (1)
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| PCT/EP2013/063716 WO2014206500A1 (en) | 2013-06-28 | 2013-06-28 | Method for manufacturing a shaped cross-linked hyaluronic acid product |
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| AU2013396752A1 AU2013396752A1 (en) | 2016-02-18 |
| AU2013396752B2 true AU2013396752B2 (en) | 2018-11-08 |
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| KR101831948B1 (ko) | 2015-02-13 | 2018-02-23 | 주식회사 엔도더마 | 가교된 히알루론산 하이드로젤을 이용한 마이크로구조체 및 이의 제조방법 |
| WO2017016917A1 (en) | 2015-07-27 | 2017-02-02 | Galderma Sa | A process for efficient cross-linking of hyaluronic acid |
| KR101709608B1 (ko) * | 2015-09-03 | 2017-03-09 | (주)진우바이오 | 용융 방사에 의한 히알루론산염 파이버의 제조방법 및 이로부터 제조된 히알루론산염 파이버 |
| EP3350240B1 (en) * | 2015-09-18 | 2023-08-09 | Arkema, Inc. | Polyol pre-mixes having improved shelf life |
| KR20170090965A (ko) * | 2016-01-29 | 2017-08-08 | 한미약품 주식회사 | 복합 히알루론산 가교물 및 그 제조방법 |
| CN109996566A (zh) * | 2016-10-18 | 2019-07-09 | 奥尔胡斯大学 | 打印的透明质酸支架 |
| WO2018122344A1 (en) | 2016-12-29 | 2018-07-05 | Nestlé Skin Health Sa | Composition comprising a crosslinked hyaluronic acid (ha) in combination with a low-molecular ha and/or an agent stimulating endogenous ha synthesis |
| WO2018122342A1 (en) * | 2016-12-29 | 2018-07-05 | Nestlé Skin Health Sa | Micro- or nanoparticular multilamellar vesicles, compositions comprising the same and method for their use in skin care |
| EP3562469A1 (en) | 2016-12-29 | 2019-11-06 | Nestlé Skin Health SA | Micro- or nanoparticular vesicles comprising crosslinked hyaluronic acid, compositions comprising the same and method for their use in skin care |
| IL269506B2 (en) | 2017-03-22 | 2024-04-01 | Genentech Inc | Hydrogel cross-linked hyaluronic acid prodrug compositions and methods |
| WO2019073364A1 (en) * | 2017-10-12 | 2019-04-18 | Solyplus Berlin Gmbh | CROSSLINKING BIOPOLYMERS IN A SEMI-SOLID STATE |
| US12097277B2 (en) * | 2018-06-15 | 2024-09-24 | Croma-Pharma Gmbh | Hydrogel composition comprising a crosslinked polymer |
| MX2021011444A (es) * | 2019-03-24 | 2022-01-04 | Allergan Pharmaceuticals Int Ltd | Geles inyectables homogeneos que comprenden multiples formas de acido hialuronico y metodos para su fabricacion. |
| JP2022529953A (ja) * | 2019-04-19 | 2022-06-27 | ジョインセラピュイティクス エッセ．エッレ．エッレ． | 官能化ヒアルロン酸の架橋ポリマーと、炎症状態の治療におけるその使用 |
| EP3797800A1 (en) * | 2019-05-02 | 2021-03-31 | Institut National De La Sante Et De La Recherche Medicale - Inserm | Hyaluronic acid hydrogels with prolonged antimicrobial activity |
| WO2020234167A1 (en) * | 2019-05-17 | 2020-11-26 | ETH Zürich | Printable hydrogel, method for generating a printable hydrogel, lyophilizate, printed product and 3d printing method |
| CN112147029A (zh) * | 2019-06-28 | 2020-12-29 | 杭州协合医疗用品有限公司 | 一种交联透明质酸钠凝胶溶胀度的测定方法 |
| US20220298310A1 (en) * | 2019-09-27 | 2022-09-22 | Lg Chem, Ltd. | A method of preparing polymeric microparticles, polymeric microparticles, medical composition, cosmetic composition, medical articles and cosmetic articles using the same |
| KR102173790B1 (ko) * | 2020-02-26 | 2020-11-03 | (주) 제이피케어즈 | 가교 히알루론산을 이용한 약물 전달 조성물 및 이의 제조방법 |
| WO2021262986A1 (en) * | 2020-06-24 | 2021-12-30 | Anika Therapeutics, Inc. | Composite medical textile with non-resorbable fibers and bioresorbable hyaluronan-based fibers |
| US12324867B2 (en) * | 2020-11-26 | 2025-06-10 | Jinwoo Bio Co., Ltd. | Hyaluronate fiber and manufacturing method thereof |
| KR102527095B1 (ko) | 2020-12-18 | 2023-04-28 | 충남대학교산학협력단 | 가교 처리된 히알루론산 조성물의 가교율 측정방법 |
| CN113045779B (zh) * | 2021-03-22 | 2022-09-02 | 华熙生物科技股份有限公司 | 一种交联透明质酸凝胶粗品及其制备方法 |
| US20240352158A1 (en) * | 2021-10-15 | 2024-10-24 | Prohibix Llc | Crosslinked hyaluronic acid precipitates |
| CN114404355B (zh) * | 2021-12-28 | 2024-05-24 | 常州药物研究所有限公司 | 透明质酸钠凝胶及其制备方法、应用 |
| EP4473021A1 (en) | 2022-02-01 | 2024-12-11 | Galderma Holding SA | Methods of producing crosslinked hyaluronic acid hydrogels |
| CN114894789B (zh) * | 2022-06-28 | 2025-08-15 | 华熙生物科技股份有限公司 | 一种透明质酸类物质指示剂组合物及其在快速检测透明质酸类物质中的应用 |
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-
2013
- 2013-06-28 EP EP19202714.2A patent/EP3617236B1/en active Active
- 2013-06-28 EP EP13732529.6A patent/EP3013865B1/en active Active
- 2013-06-28 US US14/901,546 patent/US10077321B2/en active Active
- 2013-06-28 CN CN201380079033.3A patent/CN105473622B/zh active Active
- 2013-06-28 BR BR112015031589A patent/BR112015031589A2/pt not_active Application Discontinuation
- 2013-06-28 KR KR1020167002526A patent/KR102048395B1/ko active Active
- 2013-06-28 MX MX2015017526A patent/MX369409B/es active IP Right Grant
- 2013-06-28 JP JP2016522286A patent/JP6434003B2/ja not_active Expired - Fee Related
- 2013-06-28 RU RU2016101734A patent/RU2640865C2/ru not_active IP Right Cessation
- 2013-06-28 CA CA2916119A patent/CA2916119A1/en not_active Abandoned
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- 2013-06-28 AU AU2013396752A patent/AU2013396752B2/en not_active Ceased
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2018
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2020
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2021
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| US20070066816A1 (en) * | 2002-12-31 | 2007-03-22 | Industrial Technology Research Institute | Method for producing double-crosslinked hyaluronate material |
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| US11702484B2 (en) | 2023-07-18 |
| EP3013865B1 (en) | 2019-10-23 |
| KR102048395B1 (ko) | 2019-11-25 |
| HK1224314A1 (en) | 2017-08-18 |
| US20210214468A1 (en) | 2021-07-15 |
| JP6434003B2 (ja) | 2018-12-05 |
| CN109734825A (zh) | 2019-05-10 |
| EP3617236A1 (en) | 2020-03-04 |
| MX2015017526A (es) | 2016-08-05 |
| RU2640865C2 (ru) | 2018-01-12 |
| AU2013396752A1 (en) | 2016-02-18 |
| CN105473622A (zh) | 2016-04-06 |
| US20160145357A1 (en) | 2016-05-26 |
| US10982016B2 (en) | 2021-04-20 |
| MX369409B (es) | 2019-11-07 |
| KR20160027095A (ko) | 2016-03-09 |
| US20200247913A1 (en) | 2020-08-06 |
| US20180362670A1 (en) | 2018-12-20 |
| JP2016524016A (ja) | 2016-08-12 |
| CN109734825B (zh) | 2022-01-28 |
| CA2916119A1 (en) | 2014-12-31 |
| RU2016101734A (ru) | 2017-08-02 |
| BR112015031589A2 (pt) | 2017-07-25 |
| CN105473622B (zh) | 2019-01-29 |
| EP3617236B1 (en) | 2024-07-31 |
| EP3013865A1 (en) | 2016-05-04 |
| WO2014206500A1 (en) | 2014-12-31 |
| US10077321B2 (en) | 2018-09-18 |
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