CA2882964A1 - Chlorhexidine gluconate solubilized in a hydrophobic monoacylglyceride - Google Patents
Chlorhexidine gluconate solubilized in a hydrophobic monoacylglyceride Download PDFInfo
- Publication number
- CA2882964A1 CA2882964A1 CA2882964A CA2882964A CA2882964A1 CA 2882964 A1 CA2882964 A1 CA 2882964A1 CA 2882964 A CA2882964 A CA 2882964A CA 2882964 A CA2882964 A CA 2882964A CA 2882964 A1 CA2882964 A1 CA 2882964A1
- Authority
- CA
- Canada
- Prior art keywords
- monoacylglyceride
- composition
- weight
- chg
- chlorhexidine gluconate
- 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
- 230000002209 hydrophobic effect Effects 0.000 title claims abstract description 34
- 229960003333 chlorhexidine gluconate Drugs 0.000 title claims abstract description 15
- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 title claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 20
- KUXUALPOSMRJSW-IFWQJVLJSA-N 2-[6-[[amino-[[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 KUXUALPOSMRJSW-IFWQJVLJSA-N 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 230000027455 binding Effects 0.000 claims description 15
- ASKIVFGGGGIGKH-UHFFFAOYSA-N 2,3-dihydroxypropyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(O)CO ASKIVFGGGGIGKH-UHFFFAOYSA-N 0.000 claims description 10
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 claims description 10
- ARIWANIATODDMH-UHFFFAOYSA-N Lauric acid monoglyceride Natural products CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 claims description 4
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- ARIWANIATODDMH-AWEZNQCLSA-N 1-lauroyl-sn-glycerol Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)CO ARIWANIATODDMH-AWEZNQCLSA-N 0.000 claims description 3
- 125000003892 C18 acyl group Chemical group 0.000 claims description 3
- 239000013008 thixotropic agent Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000004088 simulation Methods 0.000 description 5
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 238000000329 molecular dynamics simulation Methods 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 3
- 239000012457 nonaqueous media Substances 0.000 description 3
- -1 Alkyl CHG Chemical compound 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 229940087068 glyceryl caprylate Drugs 0.000 description 2
- 229940068939 glyceryl monolaurate Drugs 0.000 description 2
- 229940075507 glyceryl monostearate Drugs 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 1
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000353097 Molva molva Species 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229960003260 chlorhexidine Drugs 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 235000012209 glucono delta-lactone Nutrition 0.000 description 1
- 229960003681 gluconolactone Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012900 molecular simulation Methods 0.000 description 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- RARSHUDCJQSEFJ-UHFFFAOYSA-N p-Hydroxypropiophenone Chemical compound CCC(=O)C1=CC=C(O)C=C1 RARSHUDCJQSEFJ-UHFFFAOYSA-N 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000008866 synergistic binding Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- 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
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/43—Guanidines
-
- 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
- A61K9/08—Solutions
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- 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
- A61K2800/10—General cosmetic use
-
- 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
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/30—Characterized by the absence of a particular group of ingredients
- A61K2800/31—Anhydrous
-
- 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
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/524—Preservatives
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Birds (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261694080P | 2012-08-28 | 2012-08-28 | |
| US61/694,080 | 2012-08-28 | ||
| PCT/US2013/056802 WO2014035971A2 (en) | 2012-08-28 | 2013-08-27 | Chlorhexidine gluconate solubilized in a hydrophobic monoacylglyceride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2882964A1 true CA2882964A1 (en) | 2014-03-06 |
Family
ID=49151333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2882964A Abandoned CA2882964A1 (en) | 2012-08-28 | 2013-08-27 | Chlorhexidine gluconate solubilized in a hydrophobic monoacylglyceride |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20150238444A1 (enExample) |
| EP (1) | EP2890362B1 (enExample) |
| JP (1) | JP6158928B2 (enExample) |
| CN (1) | CN104684536B (enExample) |
| AU (1) | AU2013308992B2 (enExample) |
| BR (1) | BR112015004178A2 (enExample) |
| CA (1) | CA2882964A1 (enExample) |
| MX (1) | MX367220B (enExample) |
| WO (1) | WO2014035971A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2373270B8 (en) | 2009-01-07 | 2023-04-12 | entrotech life sciences, inc. | Chlorhexidine-containing antimicrobial laminates |
| BR112015004600A2 (pt) | 2012-08-28 | 2017-07-04 | 3M Innovative Properties Co | composições de gluconato de clorexidina, sistemas e artigos de resina |
| US11039615B2 (en) | 2014-04-18 | 2021-06-22 | Entrotech Life Sciences, Inc. | Methods of processing chlorhexidine-containing polymerizable compositions and antimicrobial articles formed thereby |
| WO2017160785A1 (en) | 2016-03-18 | 2017-09-21 | 3M Innovative Properties Company | Adhesive compositions with (meth) acrylic-based block copolymers |
| WO2020109934A1 (en) * | 2018-11-30 | 2020-06-04 | 3M Innovative Properties Company | Topical antimicrobial microemulsions with fluorescent materials |
| WO2021019339A1 (en) | 2019-08-01 | 2021-02-04 | 3M Innovative Properties Company | An antimicrobial device for an insertion needle |
| US12179472B2 (en) | 2019-11-04 | 2024-12-31 | Solventum Intellectual Properties Company | Reinforced adhesive substrate |
| EP4061901A1 (en) | 2019-11-20 | 2022-09-28 | 3M Innovative Properties Company | Medical tapes with high optical clarity when over-taped |
| EP4259737A1 (en) | 2020-12-11 | 2023-10-18 | 3M Innovative Properties Company | Perforated tapes for medical applications |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1599159A (en) * | 1977-02-08 | 1981-09-30 | Roussel Lab Ltd | Pharmaceutical compositions containing chlorhexidine |
| JPH02140167A (ja) * | 1988-11-22 | 1990-05-29 | Saraya Kk | 手指消毒用組成物 |
| JPH0399010A (ja) * | 1989-09-13 | 1991-04-24 | Taisho Pharmaceut Co Ltd | 医薬組成物 |
| US5093109A (en) * | 1990-04-04 | 1992-03-03 | Chanel, Inc. | Cosmetic composition |
| US6458341B1 (en) * | 1998-06-04 | 2002-10-01 | 3M Innovative Properties Company | Devices with coatings containing chlorhexidine gluconate, compositions and methods |
| US20030031694A1 (en) * | 2001-04-20 | 2003-02-13 | 3M Innovative Properties Company | Controlled release particles |
| DE20204160U1 (de) * | 2002-03-14 | 2002-07-04 | Köhler Pharma GmbH, 64665 Alsbach-Hähnlein | Hauptpflegemittel |
| AU2003282358A1 (en) * | 2002-11-21 | 2004-06-15 | J.P.M.E.D. Ltd. | Compositions for treating infected skin and mucous membrane comprising an anti-microbial agent and an essential oil |
| US20050245738A1 (en) * | 2004-05-03 | 2005-11-03 | Lupin Ltd | Stable bioavailable crystalline form or cefdinir and a process for the preparation thereof |
| US20050271611A1 (en) * | 2004-06-08 | 2005-12-08 | Shiseido Co., Ltd. | Cosmetic |
| US20060205838A1 (en) * | 2005-03-10 | 2006-09-14 | Velamakanni Bhaskar V | Hardenable antimicrobial dental compositions and methods |
| JP2007217394A (ja) * | 2006-02-16 | 2007-08-30 | I-Nage:Kk | 医薬組成物 |
| CN101489379B (zh) * | 2006-10-27 | 2014-06-04 | 3M创新有限公司 | 抗微生物组合物 |
-
2013
- 2013-08-27 CA CA2882964A patent/CA2882964A1/en not_active Abandoned
- 2013-08-27 MX MX2015002542A patent/MX367220B/es active IP Right Grant
- 2013-08-27 AU AU2013308992A patent/AU2013308992B2/en not_active Ceased
- 2013-08-27 JP JP2015529929A patent/JP6158928B2/ja not_active Expired - Fee Related
- 2013-08-27 CN CN201380045403.1A patent/CN104684536B/zh not_active Expired - Fee Related
- 2013-08-27 US US14/424,198 patent/US20150238444A1/en not_active Abandoned
- 2013-08-27 WO PCT/US2013/056802 patent/WO2014035971A2/en not_active Ceased
- 2013-08-27 EP EP13759935.3A patent/EP2890362B1/en not_active Not-in-force
- 2013-08-27 BR BR112015004178A patent/BR112015004178A2/pt active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| MX2015002542A (es) | 2015-06-23 |
| MX367220B (es) | 2019-08-09 |
| JP2015526518A (ja) | 2015-09-10 |
| BR112015004178A2 (pt) | 2017-07-04 |
| EP2890362A2 (en) | 2015-07-08 |
| EP2890362B1 (en) | 2020-11-11 |
| AU2013308992B2 (en) | 2016-06-23 |
| WO2014035971A2 (en) | 2014-03-06 |
| CN104684536B (zh) | 2018-01-12 |
| US20150238444A1 (en) | 2015-08-27 |
| JP6158928B2 (ja) | 2017-07-05 |
| WO2014035971A3 (en) | 2014-10-30 |
| CN104684536A (zh) | 2015-06-03 |
| AU2013308992A1 (en) | 2015-03-12 |
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