JP2016530248A5 - - Google Patents
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- JP2016530248A5 JP2016530248A5 JP2016530446A JP2016530446A JP2016530248A5 JP 2016530248 A5 JP2016530248 A5 JP 2016530248A5 JP 2016530446 A JP2016530446 A JP 2016530446A JP 2016530446 A JP2016530446 A JP 2016530446A JP 2016530248 A5 JP2016530248 A5 JP 2016530248A5
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- 238000000034 method Methods 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 8
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- 150000001450 anions Chemical class 0.000 claims 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 4
- 125000006239 protecting group Chemical group 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 239000012351 deprotecting agent Substances 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims 2
- 239000005695 Ammonium acetate Substances 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 235000019257 ammonium acetate Nutrition 0.000 claims 2
- 229940043376 ammonium acetate Drugs 0.000 claims 2
- 235000019270 ammonium chloride Nutrition 0.000 claims 2
- 150000003863 ammonium salts Chemical class 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- YCNIBOIOWCTRCL-UHFFFAOYSA-N azane;2,2,2-trifluoroacetic acid Chemical compound [NH4+].[O-]C(=O)C(F)(F)F YCNIBOIOWCTRCL-UHFFFAOYSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamic acid group Chemical class C(N)(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 239000004251 Ammonium lactate Substances 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical class C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 claims 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical group 0.000 claims 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims 1
- 229940059265 ammonium lactate Drugs 0.000 claims 1
- 235000019286 ammonium lactate Nutrition 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- QKWNIOMGXBERHJ-RXSVEWSESA-N azane;(2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one Chemical compound N.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QKWNIOMGXBERHJ-RXSVEWSESA-N 0.000 claims 1
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 claims 1
- PHKGGXPMPXXISP-DFWYDOINSA-N azanium;(4s)-4-amino-5-hydroxy-5-oxopentanoate Chemical compound [NH4+].[O-]C(=O)[C@@H]([NH3+])CCC([O-])=O PHKGGXPMPXXISP-DFWYDOINSA-N 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- YEOCBTKAGVNPMO-JIZZDEOASA-N diazanium;(2s)-2-aminobutanedioate Chemical compound [NH4+].[NH4+].[O-]C(=O)[C@@H](N)CC([O-])=O YEOCBTKAGVNPMO-JIZZDEOASA-N 0.000 claims 1
- -1 dicarboxylic acids anions Chemical class 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000004693 imidazolium salts Chemical class 0.000 claims 1
- 235000013917 monoammonium glutamate Nutrition 0.000 claims 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims 1
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 239000003586 protic polar solvent Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical group [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1313465.5A GB201313465D0 (en) | 2013-07-29 | 2013-07-29 | Methods of preparing nicotinamide riboside and derivatives thereof |
| GB1313465.5 | 2013-07-29 | ||
| PCT/EP2014/065971 WO2015014722A1 (en) | 2013-07-29 | 2014-07-24 | Methods of preparing nicotinamide riboside and derivatives thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016530248A JP2016530248A (ja) | 2016-09-29 |
| JP2016530248A5 true JP2016530248A5 (enExample) | 2017-09-07 |
| JP6208352B2 JP6208352B2 (ja) | 2017-10-04 |
Family
ID=49167061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016530446A Active JP6208352B2 (ja) | 2013-07-29 | 2014-07-24 | ニコチンアミドリボシドおよびその誘導体を調製する方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (7) | US10000519B2 (enExample) |
| EP (2) | EP3321274A1 (enExample) |
| JP (1) | JP6208352B2 (enExample) |
| KR (2) | KR102414886B1 (enExample) |
| CN (2) | CN108707174A (enExample) |
| AU (4) | AU2014298629B2 (enExample) |
| BR (1) | BR112016001774B1 (enExample) |
| CA (2) | CA3192957A1 (enExample) |
| ES (1) | ES2652654T3 (enExample) |
| GB (1) | GB201313465D0 (enExample) |
| HK (1) | HK1255037A1 (enExample) |
| MX (1) | MX349969B (enExample) |
| WO (1) | WO2015014722A1 (enExample) |
| ZA (1) | ZA201802315B (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201313465D0 (en) | 2013-07-29 | 2013-09-11 | Queens University Of The Belfast | Methods of preparing nicotinamide riboside and derivatives thereof |
| WO2015186068A1 (en) * | 2014-06-02 | 2015-12-10 | Glaxosmithkline Intellectual Property (No.2) Limited | Preparation and use of crystalline beta-d-nicotinamide riboside |
| RU2016149767A (ru) | 2014-06-06 | 2018-07-16 | Глэксосмитклайн Интеллекчуал Проперти (Но.2) Лимитед | Аналоги никотинамидрибозида и фармацевтические композиции и их применение |
| CN106715454B (zh) * | 2014-07-24 | 2020-06-16 | 格雷斯公司 | 烟酰胺核苷的结晶形式 |
| CA2978069C (en) | 2015-03-09 | 2021-10-12 | W.R. Grace & Co.-Conn. | Crystalline form of nicotinamide riboside |
| BR112017019696A2 (pt) * | 2015-03-16 | 2018-09-04 | ChromaDex Inc. | composto e usos de um composto |
| US10392414B2 (en) | 2015-07-15 | 2019-08-27 | Cornell University | Syntheses, activities, and methods of use of dihydronicotinamide riboside derivatives |
| AU2016302005B2 (en) | 2015-08-05 | 2021-03-04 | Metro International Biotech, Llc | Nicotinamide mononucleotide derivatives and their uses |
| GB2542881B (en) | 2015-10-02 | 2020-01-01 | Carr Andrew | Crystal forms of ß-nicotinamide mononucleotide |
| WO2017079195A1 (en) * | 2015-11-02 | 2017-05-11 | Mitobridge, Inc. | Nicotinamide riboside and nicotinamide mononucleotide derivatives for use in the treatments of mitochondrial-related diseases |
| WO2017145151A1 (en) | 2016-02-23 | 2017-08-31 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Process for preparation of nicotinamide riboside (nr) and cosmetic composition comprising (nr and a phosphate-binding agent |
| US10000520B2 (en) | 2016-03-16 | 2018-06-19 | ChromaDex Inc. | B-vitamin and amino acid conjugates ofnicotinoyl ribosides and reduced nicotinoyl ribosides, derivatives thereof, and methods of preparation thereof |
| MX393076B (es) | 2016-04-20 | 2025-03-24 | Chromadex Inc | Uso de derivados de ribósido de ácido nicotínico o ribósido de nicotinamida, y derivados reducidos de estos, como precursores que incrementan nad+ |
| WO2017218580A1 (en) | 2016-06-14 | 2017-12-21 | Rejuvenation Therapeutics Corporation | Synthetic methods for the preparation of nicotinamide riboside and related compounds |
| GB2553001A (en) * | 2016-08-19 | 2018-02-21 | The Queen's Univ Of Belfast | Lactone intermediates of nicotinamide riboside and nicotinate riboside |
| EP3538099A4 (en) | 2016-11-11 | 2020-06-17 | The Queen's University of Belfast | EFFICIENT AND SCALABLE SYNTHESIS OF NICOTINOYL RIBOSIDES AND REDUCED NICOTINOYL RIBOSIDES, MODIFIED DERIVATIVES THEREOF, PHOSPHORYLATED ANALOGS OF THEM, ADENYLYDINUCLEOTIDE CONJUGATES THEREOF AND NEW-WAY CRYSTALS |
| US11071747B2 (en) | 2016-11-29 | 2021-07-27 | University Of Iowa Research Foundation | Use of NAD precursors for breast enhancement |
| EP3554285A4 (en) | 2016-11-29 | 2021-01-20 | University of Iowa Research Foundation | USE OF NAD PRECURSORS TO IMPROVE THE HEALTH OF MOTHER AND / OR OFFspring |
| EP3642214A2 (en) | 2017-06-19 | 2020-04-29 | Gangadhara Ganapati | Nicotinamide riboside derivatives and their uses |
| JP2020526511A (ja) * | 2017-06-30 | 2020-08-31 | エリジウム・ヘルス・インコーポレイテッド | ニコチンアミドリボシドの合成方法 |
| WO2019122084A1 (en) | 2017-12-22 | 2019-06-27 | Stemtek Therapeutics, S.L. | Process for the preparation of nicotinamide riboside chloride derivatives |
| US11414407B2 (en) | 2017-12-22 | 2022-08-16 | Elysium Health, Inc. | Crystalline forms of nicotinamide riboside chloride |
| WO2019152416A1 (en) | 2018-01-30 | 2019-08-08 | Metro International Biotech, Llc | Nicotinamide riboside analogs, pharmaceutical compositions, and uses thereof |
| CN110283221A (zh) * | 2018-03-19 | 2019-09-27 | 药源药物化学（上海）有限公司 | 杂环化合物的制备和纯化方法 |
| CN110452277A (zh) * | 2018-05-07 | 2019-11-15 | 明特奇点医疗科技(成都)有限公司 | 一种烟酰胺核糖的制备方法 |
| CN113490675B (zh) * | 2018-05-22 | 2026-01-09 | 江普斯塔特生育有限公司 | 作为抗衰老剂的烟酸核苷的氨基酸盐 |
| US12403152B2 (en) | 2018-06-21 | 2025-09-02 | Societe Des Produits Nestle S.A. | Compositions and methods using a nicotinamide adenine dinucleotide (NAD+) precursor and at least one ketone or ketone precursor |
| CN108774278A (zh) * | 2018-09-10 | 2018-11-09 | 张洪喜 | 一种制备尼克酰胺核苷盐的方法 |
| KR102060374B1 (ko) * | 2018-12-14 | 2019-12-30 | 주식회사 휴메딕스 | 지방알코올 컨쥬게이션된 니코틴아미드 리보사이드 유도체 |
| US11833167B2 (en) | 2018-12-17 | 2023-12-05 | Mitopower Llc | Nicotinyl riboside compounds and their uses |
| US10618927B1 (en) | 2019-03-22 | 2020-04-14 | Metro International Biotech, Llc | Compositions and methods for modulation of nicotinamide adenine dinucleotide |
| US11939348B2 (en) | 2019-03-22 | 2024-03-26 | Metro International Biotech, Llc | Compositions comprising a phosphorus derivative of nicotinamide riboside and methods for modulation of nicotinamide adenine dinucleotide |
| CN119684381A (zh) | 2019-07-19 | 2025-03-25 | 生物合成股份公司 | 烟酰胺呋喃核糖苷盐的结晶形式以及包含其的营养补充剂和药物组合物 |
| CN114555619A (zh) * | 2019-08-14 | 2022-05-27 | 麦德龙国际生物科技有限责任公司 | 用于烟酰胺腺嘌呤二核苷酸的差分调节的化合物和组合物 |
| CN110642897B (zh) * | 2019-09-27 | 2021-04-06 | 武汉一若生物材料有限公司 | 一种β-烟酰胺核糖氯化物的制备方法 |
| CN110658224B (zh) * | 2019-10-15 | 2022-11-22 | 中国中医科学院中药研究所 | 一种氢核磁定量分析技术测定nmn绝对含量的方法 |
| CN111153953A (zh) * | 2020-01-07 | 2020-05-15 | 杭州洁汉化工有限公司 | 一种烟酰胺核糖氯化物的高效合成方法 |
| CN111454311B (zh) * | 2020-04-03 | 2021-10-19 | 深圳市迪克曼科技开发有限公司 | 烟酰胺核糖的有机酸盐及其组合物与制备方法 |
| CN111647032B (zh) * | 2020-06-29 | 2023-02-24 | 上海舒泽生物科技研究所 | 一种β-烟酰胺单核苷酸的合成方法 |
| CN111848710A (zh) * | 2020-08-20 | 2020-10-30 | 深圳市迪克曼科技开发有限公司 | 烟酰胺核糖及其还原态、盐的制备方法 |
| US20230271995A1 (en) * | 2020-09-15 | 2023-08-31 | Societe Des Produits Nestle S.A. | Methods for producing dihydronicotinamide riboside from nicotinamide riboside chloride |
| CN112851730B (zh) * | 2021-01-08 | 2023-02-21 | 厦门瑞林药业有限公司 | 一种nmn中间体nr氯化物合成方法 |
| WO2022233923A1 (en) | 2021-05-04 | 2022-11-10 | Bohan & Co As. | A process for synthesis of nicotinamide riboside chloride (nrcl) |
| IL308577A (en) | 2021-05-27 | 2024-01-01 | Metro Int Biotech Llc | Crystalline solids of nicotinic acid mononucleotides and their esters and methods for their preparation and use |
| AU2023227391A1 (en) | 2022-03-04 | 2024-10-17 | Bohan & Co As. | Process for synthesis of 1,4-dihydronicotinamide riboside (nrh) from nicotinamide-beta-riboside triacetate chloride (nra-cl) |
| CN116462727A (zh) * | 2023-04-23 | 2023-07-21 | 安徽瑞邦生物科技有限公司 | 一种β-烟酰胺核糖氯化物的制备方法 |
| WO2024259359A2 (en) * | 2023-06-14 | 2024-12-19 | ChromaDex Inc. | Nicotinamide riboside and derivatives thereof in intravenous formulations and methods of use thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5633158A (en) | 1991-10-23 | 1997-05-27 | Cancer Research Campaign Technology Limited | Bacterial nitroreductase for the reduction of CB 1954 and analogues thereof to a cytotoxic form |
| US6689760B1 (en) | 2000-07-10 | 2004-02-10 | Enzrel Inc. | Anti-mycobacterial compositions |
| ES2670927T3 (es) * | 2005-11-18 | 2018-06-04 | Cornell Research Foundation, Inc. | Composiciones de nicotinoil ribósido y métodos de uso |
| WO2011081942A1 (en) | 2009-12-14 | 2011-07-07 | Cornell University | Activation and activators of sirt5 |
| KR20130044382A (ko) * | 2010-03-01 | 2013-05-02 | 마이렉시스 인코포레이티드 | 화합물 및 그의 치료 용도 |
| GB201313465D0 (en) | 2013-07-29 | 2013-09-11 | Queens University Of The Belfast | Methods of preparing nicotinamide riboside and derivatives thereof |
| RU2016149767A (ru) * | 2014-06-06 | 2018-07-16 | Глэксосмитклайн Интеллекчуал Проперти (Но.2) Лимитед | Аналоги никотинамидрибозида и фармацевтические композиции и их применение |
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2013
- 2013-07-29 GB GBGB1313465.5A patent/GB201313465D0/en not_active Ceased
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2014
- 2014-07-24 WO PCT/EP2014/065971 patent/WO2015014722A1/en not_active Ceased
- 2014-07-24 AU AU2014298629A patent/AU2014298629B2/en active Active
- 2014-07-24 MX MX2016001211A patent/MX349969B/es active IP Right Grant
- 2014-07-24 EP EP17191481.5A patent/EP3321274A1/en active Pending
- 2014-07-24 EP EP14744082.0A patent/EP3027635B1/en active Active
- 2014-07-24 CN CN201810413840.9A patent/CN108707174A/zh active Pending
- 2014-07-24 KR KR1020217009552A patent/KR102414886B1/ko active Active
- 2014-07-24 CN CN201480043268.1A patent/CN105636973B/zh active Active
- 2014-07-24 CA CA3192957A patent/CA3192957A1/en active Pending
- 2014-07-24 JP JP2016530446A patent/JP6208352B2/ja active Active
- 2014-07-24 BR BR112016001774-9A patent/BR112016001774B1/pt active IP Right Grant
- 2014-07-24 US US14/908,831 patent/US10000519B2/en active Active
- 2014-07-24 KR KR1020167005556A patent/KR102303966B1/ko active Active
- 2014-07-24 ES ES14744082.0T patent/ES2652654T3/es active Active
- 2014-07-24 CA CA2918955A patent/CA2918955C/en active Active
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2018
- 2018-02-27 US US15/905,922 patent/US10815262B2/en active Active
- 2018-04-09 ZA ZA2018/02315A patent/ZA201802315B/en unknown
- 2018-08-01 AU AU2018211238A patent/AU2018211238A1/en not_active Abandoned
- 2018-11-06 HK HK18114160.5A patent/HK1255037A1/en unknown
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2020
- 2020-02-21 AU AU2020201254A patent/AU2020201254B2/en active Active
- 2020-05-29 US US16/886,985 patent/US11584770B2/en active Active
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2022
- 2022-05-04 US US17/736,834 patent/US11981698B2/en active Active
- 2022-05-12 AU AU2022203196A patent/AU2022203196B2/en active Active
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2023
- 2023-04-26 US US18/307,733 patent/US12252506B2/en active Active
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2024
- 2024-03-07 US US18/598,617 patent/US20240239831A1/en active Pending
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2025
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