CA2984203C - PHENYLCYCLOPROPYLAMINE COMPOUNDS AS A LYSINE-SPECIFIC DEMETHYLASE-1 (LSD1) INHIBITOR - Google Patents
PHENYLCYCLOPROPYLAMINE COMPOUNDS AS A LYSINE-SPECIFIC DEMETHYLASE-1 (LSD1) INHIBITORInfo
- Publication number
- CA2984203C CA2984203C CA2984203A CA2984203A CA2984203C CA 2984203 C CA2984203 C CA 2984203C CA 2984203 A CA2984203 A CA 2984203A CA 2984203 A CA2984203 A CA 2984203A CA 2984203 C CA2984203 C CA 2984203C
- Authority
- CA
- Canada
- Prior art keywords
- cancer
- xrpd
- solid form
- 2theta
- particular embodiment
- 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.)
- Active
Links
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
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/40—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing only non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Virology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15166641.9 | 2015-05-06 | ||
| EP15166641.9A EP3090998A1 (en) | 2015-05-06 | 2015-05-06 | Solid forms |
| PCT/EP2016/059726 WO2016177656A1 (en) | 2015-05-06 | 2016-05-02 | Solid forms |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2984203A1 CA2984203A1 (en) | 2016-11-10 |
| CA2984203C true CA2984203C (en) | 2024-07-02 |
Family
ID=53039825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2984203A Active CA2984203C (en) | 2015-05-06 | 2016-05-02 | PHENYLCYCLOPROPYLAMINE COMPOUNDS AS A LYSINE-SPECIFIC DEMETHYLASE-1 (LSD1) INHIBITOR |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US10221125B2 (cg-RX-API-DMAC7.html) |
| EP (2) | EP3090998A1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP7005007B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102666390B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN107735394B (cg-RX-API-DMAC7.html) |
| AR (1) | AR104505A1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2016259054B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR112017023740B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2984203C (cg-RX-API-DMAC7.html) |
| ES (1) | ES2969970T3 (cg-RX-API-DMAC7.html) |
| HU (1) | HUE065558T2 (cg-RX-API-DMAC7.html) |
| IL (1) | IL255194B (cg-RX-API-DMAC7.html) |
| MX (1) | MX378732B (cg-RX-API-DMAC7.html) |
| PL (1) | PL3292100T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2016177656A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2768805B1 (en) | 2011-10-20 | 2020-03-25 | Oryzon Genomics, S.A. | (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors |
| EP3090998A1 (en) | 2015-05-06 | 2016-11-09 | F. Hoffmann-La Roche AG | Solid forms |
| CA3253937A1 (en) | 2016-03-15 | 2025-03-04 | Oryzon Genomics, S.A. | Combinations of Lysine-Specific Demethylase 1 Inhibitors for the Treatment of Hematological Maligna |
| CA3017411C (en) | 2016-03-15 | 2024-06-25 | Oryzon Genomics, S.A. | Combinations of lsd1 inhibitors for use in the treatment of solid tumors |
| EP3430015B9 (en) | 2016-03-16 | 2025-12-31 | Oryzon Genomics, S.A. | METHODS FOR DETERMINING THE ENGAGEMENT OF A KDM1A TARGET AND CORRESPONDING USEFUL CHEMOPROBE |
| ES2732669T3 (es) | 2016-06-10 | 2019-11-25 | Oryzon Genomics Sa | Tratamiento de la esclerosis múltiple |
| AU2018309372B2 (en) | 2017-08-03 | 2024-08-15 | Oryzon Genomics, S.A. | Methods of treating behavior alterations |
| CN112040934A (zh) * | 2018-05-04 | 2020-12-04 | 奥莱松基因组股份有限公司 | 稳定的药物制剂 |
| AU2020242302B2 (en) | 2019-03-20 | 2025-10-30 | Oryzon Genomics, S.A. | Methods of treating borderline personality disorder |
| CN113631164A (zh) | 2019-03-20 | 2021-11-09 | 奥莱松基因组股份有限公司 | 使用kdm1a抑制剂如化合物伐菲德司他治疗注意缺陷多动症的方法 |
| WO2020193631A1 (en) * | 2019-03-25 | 2020-10-01 | Oryzon Genomics, S.A. | Combinations of iadademstat for cancer therapy |
| JP2022546908A (ja) | 2019-07-05 | 2022-11-10 | オリゾン・ゲノミクス・ソシエダッド・アノニマ | Ｋｄｍ１ａ阻害剤を使用した小細胞肺がんの個別化された処置のためのバイオマーカーおよび方法 |
| AU2022254484A1 (en) | 2021-04-08 | 2023-11-09 | Oryzon Genomics, S.A. | Combinations of lsd1 inhibitors for treating myeloid cancers |
| WO2023217758A1 (en) | 2022-05-09 | 2023-11-16 | Oryzon Genomics, S.A. | Methods of treating malignant peripheral nerve sheath tumor (mpnst) using lsd1 inhibitors |
| JP2025516648A (ja) | 2022-05-09 | 2025-05-30 | オリゾン・ゲノミクス・ソシエダッド・アノニマ | Ｌｓｄ１阻害薬を用いるｎｆ１変異腫瘍の治療法 |
| KR20250109775A (ko) | 2022-11-24 | 2025-07-17 | 오리존 지노믹스 에스.에이. | 암 치료를 위한 lsd1 억제제 및 메닌 억제제의 조합 |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2591717A1 (en) | 2004-12-16 | 2006-07-06 | President And Fellows Of Harvard College | Histone demethylation mediated by the nuclear amine oxidase homolog lsd1 |
| DE602005022826D1 (de) | 2005-02-18 | 2010-09-23 | Universitaetsklinikum Freiburg | Kontrolle der Androgen Rezeptor-abhängigen Gen Expression durch Hemmung der Aminoxidase Aktivität der Lysin spezifischen Demethylase (LSD1) |
| JP5484728B2 (ja) | 2005-08-10 | 2014-05-07 | ジョンズ ホプキンス ユニバーシティ | 抗寄生虫治療薬および抗癌治療薬ならびにリジン特異的デメチラーゼ阻害物質として有用なポリアミン類 |
| JP2010523685A (ja) | 2007-04-13 | 2010-07-15 | ザ・ジョンズ・ホプキンス・ユニバーシティー | リジン特異的デメチラーゼ阻害剤 |
| EP2317992A2 (en) | 2008-07-24 | 2011-05-11 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Preventing or treating viral infection using an inhibitor of the lsd1 protein, a mao inhibitor or an inhibitor of lsd1 and a mao inhibitor |
| WO2010043721A1 (en) | 2008-10-17 | 2010-04-22 | Oryzon Genomics, S.A. | Oxidase inhibitors and their use |
| US8993808B2 (en) | 2009-01-21 | 2015-03-31 | Oryzon Genomics, S.A. | Phenylcyclopropylamine derivatives and their medical use |
| US8389580B2 (en) | 2009-06-02 | 2013-03-05 | Duke University | Arylcyclopropylamines and methods of use |
| EP2258865A1 (en) | 2009-06-05 | 2010-12-08 | Universitätsklinikum Freiburg | Lysine-specific demethylase 1 (LSD1) is a biomarker for breast cancer |
| JPWO2010143582A1 (ja) | 2009-06-11 | 2012-11-22 | 公立大学法人名古屋市立大学 | フェニルシクロプロピルアミン誘導体及びｌｓｄ１阻害剤 |
| EP2467359A4 (en) | 2009-08-18 | 2013-01-09 | Univ Johns Hopkins | (BIS-) UREA- AND (BIS-) THIOMINE COMPOUNDS AS EPIGENE MODULATORS OF THE LYSINE-SPECIFIC DEMETHYLASE 1 AND METHODS OF DISEASE TREATMENT THEREWITH |
| BR112012006572A2 (pt) | 2009-09-25 | 2016-04-26 | Oryzon Genomics Sa | inibidores de demetilase-1 de lisina específicos e seu uso |
| WO2011042217A1 (en) | 2009-10-09 | 2011-04-14 | Oryzon Genomics S.A. | Substituted heteroaryl- and aryl- cyclopropylamine acetamides and their use |
| WO2011106573A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with hepadnaviridae |
| US9616058B2 (en) | 2010-02-24 | 2017-04-11 | Oryzon Genomics, S.A. | Potent selective LSD1 inhibitors and dual LSD1/MAO-B inhibitors for antiviral use |
| WO2011113005A2 (en) | 2010-03-12 | 2011-09-15 | The Johns Hopkins University | Compositions and methods for combinations of oligoamines with 2-difluoromethylornithine (dfmo) |
| AU2011244325B2 (en) | 2010-04-19 | 2015-12-17 | Oryzon Genomics S.A. | Lysine specific demethylase-1 inhibitors and their use |
| PL2560949T3 (pl) | 2010-04-20 | 2017-01-31 | Università Degli Studi Di Roma "La Sapienza" | Pochodne tranylocyprominy jako inhibitory demetylazy histonowej LSD1 i/lub LSD2 |
| CA2806008C (en) | 2010-07-29 | 2019-07-09 | Oryzon Genomics S.A. | Arylcyclopropylamine based demethylase inhibitors of lsd1 and their medical use |
| WO2012013727A1 (en) | 2010-07-29 | 2012-02-02 | Oryzon Genomics S.A. | Cyclopropylamine derivatives useful as lsd1 inhibitors |
| US9527805B2 (en) | 2010-09-10 | 2016-12-27 | Robert A. Casero | Small molecules as epigenetic modulators of lysine-specific demethylase 1 and methods of treating disorders |
| US20130303545A1 (en) | 2010-09-30 | 2013-11-14 | Tamara Maes | Cyclopropylamine derivatives useful as lsd1 inhibitors |
| WO2012045883A1 (en) | 2010-10-08 | 2012-04-12 | Oryzon Genomics S.A. | Cyclopropylamine inhibitors of oxidases |
| WO2012072713A2 (en) | 2010-11-30 | 2012-06-07 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with flaviviridae |
| WO2012107499A1 (en) | 2011-02-08 | 2012-08-16 | Oryzon Genomics S.A. | Lysine demethylase inhibitors for myeloproliferative or lymphoproliferative diseases or disorders |
| EP3981395A1 (en) | 2011-02-08 | 2022-04-13 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for myeloproliferative disorders |
| KR101884493B1 (ko) | 2011-03-25 | 2018-08-01 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | Lsd1 억제제로서의 시클로프로필아민 |
| WO2012156531A2 (en) | 2011-05-19 | 2012-11-22 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for inflammatory diseases or conditions |
| US20140296255A1 (en) | 2011-05-19 | 2014-10-02 | Oryzong Genomics, S.A. | Lysine demethylase inhibitors for thrombosis and cardiovascular diseases |
| EP2768805B1 (en) | 2011-10-20 | 2020-03-25 | Oryzon Genomics, S.A. | (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors |
| KR102079406B1 (ko) | 2011-10-20 | 2020-02-19 | 오리존 지노믹스 에스.에이. | Lsd1 억제제로서의 (헤테로)아릴 사이클로프로필아민 화합물 |
| EP3090998A1 (en) | 2015-05-06 | 2016-11-09 | F. Hoffmann-La Roche AG | Solid forms |
| US20180284095A1 (en) | 2015-06-12 | 2018-10-04 | Oryzon Genomics, S.A. | Biomarkers associated with lsd1 inhibitors and uses thereof |
| WO2017013061A1 (en) | 2015-07-17 | 2017-01-26 | Oryzon Genomics, S.A. | Biomarkers associated with lsd1 inhibitors and uses thereof |
| WO2017060319A1 (en) | 2015-10-09 | 2017-04-13 | F. Hoffmann-La Roche Ag | Gene expression biomarkers for personalized cancer care to epigenetic modifying agents |
| CA3253937A1 (en) | 2016-03-15 | 2025-03-04 | Oryzon Genomics, S.A. | Combinations of Lysine-Specific Demethylase 1 Inhibitors for the Treatment of Hematological Maligna |
| CA3017411C (en) | 2016-03-15 | 2024-06-25 | Oryzon Genomics, S.A. | Combinations of lsd1 inhibitors for use in the treatment of solid tumors |
| EP3430015B9 (en) | 2016-03-16 | 2025-12-31 | Oryzon Genomics, S.A. | METHODS FOR DETERMINING THE ENGAGEMENT OF A KDM1A TARGET AND CORRESPONDING USEFUL CHEMOPROBE |
| WO2018083138A1 (en) | 2016-11-03 | 2018-05-11 | Oryzon Genomics, S.A. | Pharmacodynamic biomarkers for personalized cancer care using epigenetic modifying agents |
| US20190256930A1 (en) | 2016-11-03 | 2019-08-22 | Oryzon Genomics, S.A. | Biomarkers for determining responsiveness to lsd1 inhibitors |
-
2015
- 2015-05-06 EP EP15166641.9A patent/EP3090998A1/en not_active Ceased
-
2016
- 2016-05-02 BR BR112017023740-7A patent/BR112017023740B1/pt active IP Right Grant
- 2016-05-02 CN CN201680025229.8A patent/CN107735394B/zh active Active
- 2016-05-02 EP EP16719864.7A patent/EP3292100B1/en active Active
- 2016-05-02 PL PL16719864.7T patent/PL3292100T3/pl unknown
- 2016-05-02 WO PCT/EP2016/059726 patent/WO2016177656A1/en not_active Ceased
- 2016-05-02 JP JP2017557899A patent/JP7005007B2/ja active Active
- 2016-05-02 HU HUE16719864A patent/HUE065558T2/hu unknown
- 2016-05-02 ES ES16719864T patent/ES2969970T3/es active Active
- 2016-05-02 US US15/571,945 patent/US10221125B2/en active Active
- 2016-05-02 KR KR1020177035160A patent/KR102666390B1/ko active Active
- 2016-05-02 CA CA2984203A patent/CA2984203C/en active Active
- 2016-05-02 AU AU2016259054A patent/AU2016259054B2/en active Active
- 2016-05-02 MX MX2017014035A patent/MX378732B/es unknown
- 2016-05-03 AR ARP160101249A patent/AR104505A1/es unknown
-
2017
- 2017-10-22 IL IL255194A patent/IL255194B/en active IP Right Grant
-
2021
- 2021-03-31 JP JP2021060013A patent/JP2021119136A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES2969970T3 (es) | 2024-05-23 |
| MX378732B (es) | 2025-03-11 |
| CN107735394B (zh) | 2021-11-02 |
| HK1252089A1 (en) | 2019-05-17 |
| EP3090998A1 (en) | 2016-11-09 |
| HUE065558T2 (hu) | 2024-06-28 |
| IL255194B (en) | 2021-03-25 |
| KR102666390B1 (ko) | 2024-05-21 |
| PL3292100T3 (pl) | 2024-04-22 |
| EP3292100C0 (en) | 2023-11-15 |
| MX2017014035A (es) | 2018-03-01 |
| HK1245235A1 (zh) | 2018-08-24 |
| AR104505A1 (es) | 2017-07-26 |
| AU2016259054B2 (en) | 2020-08-13 |
| CN107735394A (zh) | 2018-02-23 |
| JP2018516883A (ja) | 2018-06-28 |
| BR112017023740A2 (pt) | 2018-07-17 |
| AU2016259054A1 (en) | 2017-11-16 |
| BR112017023740B1 (pt) | 2023-11-07 |
| JP2021119136A (ja) | 2021-08-12 |
| IL255194A0 (en) | 2017-12-31 |
| WO2016177656A1 (en) | 2016-11-10 |
| CA2984203A1 (en) | 2016-11-10 |
| KR20180022660A (ko) | 2018-03-06 |
| JP7005007B2 (ja) | 2022-02-04 |
| US20180086692A1 (en) | 2018-03-29 |
| EP3292100A1 (en) | 2018-03-14 |
| EP3292100B1 (en) | 2023-11-15 |
| US10221125B2 (en) | 2019-03-05 |
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