AR105193A1 - Síntesis de shishijimicina a y sus análogos - Google Patents
Síntesis de shishijimicina a y sus análogosInfo
- Publication number
- AR105193A1 AR105193A1 ARP160101973A ARP160101973A AR105193A1 AR 105193 A1 AR105193 A1 AR 105193A1 AR P160101973 A ARP160101973 A AR P160101973A AR P160101973 A ARP160101973 A AR P160101973A AR 105193 A1 AR105193 A1 AR 105193A1
- Authority
- AR
- Argentina
- Prior art keywords
- substituted
- hydrogen
- alkyl
- alkoxy
- groups
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 19
- 229910052739 hydrogen Inorganic materials 0.000 abstract 16
- 239000001257 hydrogen Substances 0.000 abstract 16
- 125000003545 alkoxy group Chemical group 0.000 abstract 13
- 150000002431 hydrogen Chemical group 0.000 abstract 13
- 150000001875 compounds Chemical class 0.000 abstract 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 9
- 125000002252 acyl group Chemical group 0.000 abstract 7
- 125000003282 alkyl amino group Chemical group 0.000 abstract 6
- 125000005843 halogen group Chemical group 0.000 abstract 4
- -1 hydroxy, mercapto Chemical group 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 229910052717 sulfur Inorganic materials 0.000 abstract 3
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229910003827 NRaRb Inorganic materials 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 239000000611 antibody drug conjugate Substances 0.000 abstract 1
- 229940049595 antibody-drug conjugate Drugs 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61K47/68—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 antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
- A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
- A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
- A61K47/6807—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug or compound being a sugar, nucleoside, nucleotide, nucleic acid, e.g. RNA antisense
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
En otro aspecto, la presente divulgación también provee métodos de preparación de dichos compuestos. En otro aspecto, la presente divulgación también provee composiciones farmacéuticas y métodos de uso de los compuestos. Adicionalmente, se proveen conjugados anticuerpo-fármaco que contienen los compuestos. Reivindicación 1: Un compuesto de la fórmula (1), donde: R¹ es -alcanodiilo C£₈-(S)ˣ-A³ o -alcanodiilo C£₈-(S)ˣ-A³ sustituido; donde: A³ es hidrógeno o alquilo C£₁₂, cicloalquilo C£₁₂, alquenilo C£₁₂, alquinilo C£₁₂, arilo C£₁₂, heteroarilo C£₁₂, aralquilo C£₁₂, acilo C£₁₂, o una versión sustituida de cualquiera de estos grupos; y x es 1, 2 ó 3; R² es hidroxilo, o alcoxilo C£₈, aciloxilo C£₈, o una versión sustituida de cualquiera de estos grupos; R³ es NHC(Y²)R¹⁶, donde: Y² es O, NH, o NOH; y R¹⁶ es alcoxilo C£₈, alqueniloxi C£₈, alquilamino C£₈, dialquilamino C£₈, o una versión sustituida de cualquiera de estos grupos; R⁴ y R⁵ se seleccionan en forma independiente entre si entre hidrógeno y halo; X¹ es O, S, o NH; A¹ es -alcanodiilo C£₁₂-C(O)-A² o -alcanodiilo C£₁₂-C(O)-A² sustituido, o un compuesto de fórmula (2) donde: X⁴ es -CH₂- o -O-; R⁸ es hidrógeno, alquilo C£₈, cicloalquilo C£₈, alquilo C£₈ sustituido, o cicloalquilo C£₈ sustituido; R⁹ es hidrógeno, halo, hidroxilo, mercapto, alquilo C£₈, alquilo C£₈, sustituido, alcoxilo C£₈, alcoxilo C£₈ sustituido, alquiltio C£₈, alquiltio C£₈ sustituido; R¹⁰ es hidroxilo, oxo, o R¹⁰ es tomado junto con R¹¹ y es -OCHA⁴O-; con la salvedad de que cuando R¹⁰ es oxo entonces R¹⁰ y el átomo de carbono al cual está unido están unidos mediante una unión doble, y cuando R¹⁰ es tomado junto con R¹¹ entonces R¹⁰ y el átomo de carbono al cual está unido están unidos mediante una unión simple; donde A⁴ es arilo C£₁₂ o arilo C£₁₂ sustituido, o un resto de fórmula (3) donde: X⁵ es O, S, o NR¹⁸; donde: R¹⁸ es hidrógeno, alquilo C£₈, alquilo C£₈ sustituido, acilo C£₈, o acilo C£₈ sustituido; Z¹ es CH o N; y R¹⁷ es hidrógeno, hidroxilo, amino, hidrazino, carboxilo, halo, o nitro; o alquilo C£₁₂, alcoxilo C£₁₂, o una versión sustituida de cualquiera de estos grupos; R¹¹ es hidrógeno, hidroxilo, alcoxilo C£₈, o alcoxilo C£₈ sustituido; R¹² es hidrógeno, hidroxilo, alcoxilo C£₈, alcoxilo C£₈ sustituido, o -O-alcanodiilo C£₈-alquilamino C£₁₂, -OC(O)-alcanodiilo C£₈-alquilamino C£₁₂, o -OC(O)NH-alcanodiilo C£₈-alquilamino C£₁₂, o una versión sustituida de cualquiera de estos grupos; o el compuesto de fórmula (4) donde: R¹⁴ es amino o hidroxilo; o alcoxilo C£₁₂, alquilamino C£₁₂, dialquil-amino C£₁₂, o una versión sustituida de cualquiera de estos grupos, o -NRᵃRᵇ, donde: Rᵃ y Rᵇ, son cada uno hidrógeno, alquilo C£₁₂, alquilo C£₁₂ sustituido, alquenilo C£₁₂, alquenilo C£₁₂ sustituido, -C(O)O-alcanodiilo C£₆-Rᶜ, -C(O)-alcanodiilo C£₆-Rᶜ, alcanodiilo C£₆-Rᶜ, o una versión sustituida de cualquiera de estos grupos; donde: Rᶜ es hidrógeno, amino, carboxilo, hidroxilo, acilo C£₈, alcoxilo C£₈, alquilamino C£₈, dialquilamino C£₈, alquilsulfonilo C£₈, arilsulfonilo C£₈, o una versión sustituida de cualquiera de estos grupos; R¹⁵ es hidrógeno, hidroxilo, alcoxilo C£₈, o alcoxilo C£₈ sustituido; R²⁰ y R²¹ son hidrógeno, alquilo C£₈, alquilo C£₈ sustituido, alcoxilo C£₈, o alcoxilo C£₈ sustituido; A² es hidrógeno o un compuesto de fórmula (5); donde: X⁵ es O, S, o NR¹⁸; donde: R¹⁸ es hidrógeno, alquilo C£₈, alquilo C£₈ sustituido, acilo C£₈, o acilo C£₈ sustituido; n es 1, 2, 3, 4, ó 5; Z², Z³ y Z⁴ son en forma independiente entre sí N o CR¹³; y R¹³ es hidrógeno, amino, carboxilo, hidroxilo, hidrazino, halo, nitro, o mercapto; alquilo C£₁₂, acilo C£₁₂, alcoxilo C£₁₂, aciloxilo C£₁₂, o una versión sustituida de cualquiera de estos grupos; o A¹ es el compuesto de fórmula (6) donde: Y¹ es alcanodiilo C£₈; o alcanodiilo C£₈ sustituido; X² y X³ se seleccionan en forma independiente entre si entre -O-, -S-, o -NR¹⁹-, donde: R¹⁹ es hidrógeno, alquilo C£₈, o alquilo C£₈ sustituido; R⁶ es arilo C£₁₈, heteroarilo C£₁₈, o una versión sustituida de cualquiera de estos grupos; R⁷ es alquilo C£₁₂ o alquilo C£₁₂ sustituido; con la salvedad de que el compuesto no sea los compuestos de fórmulas (7), (8), ó (9); o una sal aceptable farmacéuticamente del mismo.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562186191P | 2015-06-29 | 2015-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR105193A1 true AR105193A1 (es) | 2017-09-13 |
Family
ID=57609044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP160101973A AR105193A1 (es) | 2015-06-29 | 2016-06-29 | Síntesis de shishijimicina a y sus análogos |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US10590158B2 (es) |
| EP (1) | EP3313389A1 (es) |
| JP (1) | JP2018525346A (es) |
| KR (1) | KR20180053294A (es) |
| CN (1) | CN108348489A (es) |
| AR (1) | AR105193A1 (es) |
| AU (1) | AU2016286071A1 (es) |
| BR (1) | BR112017028557A2 (es) |
| CA (1) | CA2990206A1 (es) |
| CL (1) | CL2017003500A1 (es) |
| HK (1) | HK1254923A1 (es) |
| IL (1) | IL256345A (es) |
| MA (1) | MA42273A (es) |
| MX (1) | MX2017016885A (es) |
| PE (1) | PE20180658A1 (es) |
| PH (1) | PH12018500014A1 (es) |
| RU (1) | RU2018102808A (es) |
| TW (1) | TW201713634A (es) |
| WO (1) | WO2017004172A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110357785B (zh) * | 2019-07-26 | 2020-03-24 | 东莞市领创环保材料科技有限公司 | 一种氰酸酯树脂增塑剂的制备方法 |
| CN115197188B (zh) * | 2021-04-12 | 2023-12-26 | 南开大学 | 一类具有五环骨架的倍半萜氢醌化合物及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5264586A (en) * | 1991-07-17 | 1993-11-23 | The Scripps Research Institute | Analogs of calicheamicin gamma1I, method of making and using the same |
| US5261586A (en) * | 1992-03-26 | 1993-11-16 | Chen Jen Fu | Yarn feeding device with a guiding flange |
| US5550246A (en) * | 1994-09-07 | 1996-08-27 | The Scripps Research Institute | Calicheamicin mimics |
| JP2003238584A (ja) * | 2002-02-08 | 2003-08-27 | Yamanouchi Pharmaceut Co Ltd | 新規エンジイン化合物 |
| TW200539855A (en) * | 2004-03-15 | 2005-12-16 | Wyeth Corp | Calicheamicin conjugates |
| WO2014080251A1 (en) * | 2012-11-24 | 2014-05-30 | Hangzhou Dac Biotech Co., Ltd. | Hydrophilic linkers and their uses for conjugation of drugs to cell binding molecules |
-
2016
- 2016-06-29 KR KR1020187002549A patent/KR20180053294A/ko unknown
- 2016-06-29 EP EP16818662.5A patent/EP3313389A1/en not_active Withdrawn
- 2016-06-29 BR BR112017028557A patent/BR112017028557A2/pt not_active IP Right Cessation
- 2016-06-29 CA CA2990206A patent/CA2990206A1/en not_active Abandoned
- 2016-06-29 TW TW105120685A patent/TW201713634A/zh unknown
- 2016-06-29 AR ARP160101973A patent/AR105193A1/es unknown
- 2016-06-29 US US15/740,656 patent/US10590158B2/en active Active
- 2016-06-29 RU RU2018102808A patent/RU2018102808A/ru not_active Application Discontinuation
- 2016-06-29 MA MA042273A patent/MA42273A/fr unknown
- 2016-06-29 JP JP2017568032A patent/JP2018525346A/ja active Pending
- 2016-06-29 WO PCT/US2016/040047 patent/WO2017004172A1/en active Application Filing
- 2016-06-29 AU AU2016286071A patent/AU2016286071A1/en not_active Abandoned
- 2016-06-29 PE PE2017002877A patent/PE20180658A1/es unknown
- 2016-06-29 MX MX2017016885A patent/MX2017016885A/es unknown
- 2016-06-29 CN CN201680050079.6A patent/CN108348489A/zh active Pending
-
2017
- 2017-12-17 IL IL256345A patent/IL256345A/en unknown
- 2017-12-29 CL CL2017003500A patent/CL2017003500A1/es unknown
-
2018
- 2018-01-03 PH PH12018500014A patent/PH12018500014A1/en unknown
- 2018-11-02 HK HK18114023.2A patent/HK1254923A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20180327439A1 (en) | 2018-11-15 |
| AU2016286071A8 (en) | 2019-08-08 |
| MX2017016885A (es) | 2018-09-06 |
| IL256345A (en) | 2018-02-28 |
| CN108348489A (zh) | 2018-07-31 |
| MA42273A (fr) | 2018-05-02 |
| CL2017003500A1 (es) | 2018-04-27 |
| RU2018102808A3 (es) | 2020-04-30 |
| TW201713634A (zh) | 2017-04-16 |
| WO2017004172A1 (en) | 2017-01-05 |
| EP3313389A1 (en) | 2018-05-02 |
| KR20180053294A (ko) | 2018-05-21 |
| AU2016286071A1 (en) | 2018-02-01 |
| RU2018102808A (ru) | 2019-07-30 |
| JP2018525346A (ja) | 2018-09-06 |
| BR112017028557A2 (pt) | 2018-09-04 |
| PH12018500014A1 (en) | 2018-07-09 |
| PE20180658A1 (es) | 2018-04-17 |
| US10590158B2 (en) | 2020-03-17 |
| WO2017004172A8 (en) | 2018-01-11 |
| CA2990206A1 (en) | 2017-01-05 |
| HK1254923A1 (zh) | 2019-08-02 |
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