AR111841A1 - ANILLOS 5-5 FUSIONADOS COMO INHIBIDORES DE C5a - Google Patents
ANILLOS 5-5 FUSIONADOS COMO INHIBIDORES DE C5aInfo
- Publication number
- AR111841A1 AR111841A1 ARP180101445A ARP180101445A AR111841A1 AR 111841 A1 AR111841 A1 AR 111841A1 AR P180101445 A ARP180101445 A AR P180101445A AR P180101445 A ARP180101445 A AR P180101445A AR 111841 A1 AR111841 A1 AR 111841A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- group
- haloalkyl
- ring
- independently selected
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 15
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical class 0.000 abstract 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 4
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 abstract 4
- 125000005842 heteroatom Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 3
- 229910052717 sulfur Inorganic materials 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- -1 cyano, hydroxyl Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- 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
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4162—1,2-Diazoles condensed with heterocyclic ring systems
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Liquid Crystal Substances (AREA)
- Glass Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Insulating Materials (AREA)
Abstract
Reivindicación 1: Un compuesto caracterizado porque es de la fórmula (1), o una sal farmacéuticamente aceptable del mismo, en donde: el vértice del anillo A¹ se selecciona entre el grupo que consiste en N, CH, C(O) y C(R⁴); el vértice del anillo A² se selecciona entre el grupo que consiste en N, CH, y C(R⁴); cada uno de los vértices del anillo A³, A⁴, A⁵ y A⁶ se selecciona independientemente entre el grupo que consiste en CH y C(R⁴); cada uno de los enlaces en línea discontinua indica independientemente un enlace doble o simple; R¹ se selecciona entre el grupo que consiste en -alquilen C₁₋₈-heteroarilo, -alquilen C₁₋₈-arilo C₆₋₁₀, alquilo C₁₋₈, haloalquilo C₁₋₈, -C(O)-alquilo C₁₋₈, -C(O)-arilo C₆₋₁₀, -C(O)-heteroarilo, -C(O)-cicloalquilo C₃₋₆, -C(O)-heterocicloalquilo, -C(O)NR¹ᵃR¹ᵇ, -SO₂-arilo C₆₋₁₀, -SO₂-heteroarilo, -C(O)-alquilen C₁₋₈-O-heteroarilo, -C(O)-alquilen C₁₋₈-O-arilo C₆₋₁₀, -C(O)-alquilen C₁₋₈-O-heterocicloalquilo, -C(O)-alquilen C₁₋₈-O-cicloalquilo C₃₋₆, -C(O)-alquilen C₁₋₈-heteroarilo, -C(O)-alquilen C₁₋₈-arilo C₆₋₁₀, -C(O)-alquilen C₁₋₈-heterocicloalquilo, -C(O)-alquilen C₁₋₈-cicloalquilo C₃₋₆ y -CO₂R¹ᵃ; el heterocicloalquilo es un anillo de 4 a 8 miembros que tiene desde 1 hasta 3 heteroátomos como vértices del anillo seleccionados entre N, O y S; y el grupo heteroarilo es un anillo aromático de 5 a 10 miembros que tiene desde 1 hasta 3 heteroátomos como vértices del anillo seleccionados entre N, O y S; en donde R¹ᵃ y R¹ᵇ se seleccionan, cada uno independientemente, entre el grupo que consiste en hidrógeno, alquilo C₁₋₈, y haloalquilo C₁₋₈; en donde R¹ está opcionalmente sustituido con 1 a 5 sustituyentes R⁵; R²ᵃ y R²ᵉ se seleccionan, cada uno independientemente, entre el grupo que consiste en alquilo C₁₋₆, alcoxi C₁₋₆, haloalquilo C₁₋₆, haloalquilo-O-C₁₋₆, -S-alquilo C₁₋₆, -alquilo C₁₋₆-O-alquilo C₁₋₆, -alquilo C₁₋₆-S-alquilo C₁₋₆, CN, y halógeno; R²ᵇ, R²ᶜ, y R²ᵈ se seleccionan, cada uno independientemente, entre el grupo que consiste en hidrógeno, alquilo C₁₋₆, alcoxi C₁₋₆, haloalquilo C₁₋₆, -O-haloalquilo C₁₋₆, -S-alquilo C₁₋₆, -alquilo C₁₋₆-O-alquilo C₁₋₆, -alquilo C₁₋₆-S-alquilo C₁₋₆, ciano, y halógeno; cada R³ se selecciona independientemente entre el grupo que consiste en alquilo C₁₋₆, haloalquilo C₁₋₆, halógeno e hidroxilo, y opcionalmente dos grupos R³ en el mismo átomo de carbono se combinan para formar oxo (=O) o para formar un anillo cicloalquilo de tres a cinco miembros; cada R⁴ se selecciona independientemente entre el grupo que consiste en alquilo C₁₋₆, alcoxi C₁₋₆, hidroxialquilo C₁₋₆, haloalquilo C₁₋₆, haloalcoxi C₁₋₆, -O-haloalquilo C₁₋₆, halógeno, ciano, hidroxilo, -S-alquilo C₁₋₆, -alquilo C₁₋₆-O-alquilo C₁₋₆, -alquilo C₁₋₆-S-alquilo C₁₋₆, -NR⁴ᵃR⁴ᵇ, -CONR⁴ᵃR⁴ᵇ, -CO₂R⁴ᵃ, -COR⁴ᵃ, -OC(O)NR⁴ᵃR⁴ᵇ, -NR⁴ᵃC(O)R⁴ᵇ, -NR⁴ᵃC(O)₂R⁴ᵇ, y -NR⁴ᵃ-C(O)NR⁴ᵃR⁴ᵇ; cada R⁴ᵃ y R⁴ᵇ se selecciona independientemente entre el grupo que consiste en hidrógeno, alquilo C₁₋₄, y haloalquilo C₁₋₄; cada R⁵ se selecciona independientemente entre el grupo que consiste en alquilo C₁₋₈, alcoxi C₁₋₈, haloalquilo C₁₋₈, haloalcoxi C₁₋₈, hidroxialquilo C₁₋₈, -alquilen C₁₋₈-heterocicloalquilo, -alquilen C₁₋₈-cicloalquilo C₃₋₆, cicloalquilo C₃₋₆, heterocicloalquilo, halógeno, OH, alquenilo C₂₋₈, alquinilo C₂₋₈, CN, C(O)R⁵ᵃ, -NR⁵ᵇC(O)R⁵ᵃ, -CONR⁵ᵃR⁵ᵇ, -NR⁵ᵃR⁵ᵇ, -alquileno C₁₋₈-NR⁵ᵃR⁵ᵇ, -S-alquilo C₁₋₆, -alquilen C₁₋₆-O-alquilo C₁₋₆, -alquilen C₁₋₆-S-alquilo C₁₋₆, -OC(O)NR⁵ᵃR⁵ᵇ, -NR⁵ᵃC(O)₂R⁵ᵇ, -NR⁵ᵃ-C(O)NR⁵ᵇR⁵ᵇ, y CO₂R⁵ᵃ; en donde el grupo heterocicloalquilo es un anillo de 4 a 8 miembros que tiene desde 1 hasta 3 heteroátomos como vértices del anillo seleccionados entre N, O, y S; en donde cada R⁵ᵃ y R⁵ᵇ se selecciona independientemente entre el grupo que consiste en hidrógeno, alquilo C₁₋₈, y haloalquilo C₁₋₈, o cuando R⁵ᵃ y R⁵ᵇ están unidos al mismo átomo de nitrógeno, se combinan con el átomo de nitrógeno para formar un anillo de 5 ó 6 miembros que tiene desde 0 a 1 heteroátomos adicionales como vértices del anillo seleccionados entre N, O, o S; y el subíndice n es 0, 1, 2 ó 3.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762513025P | 2017-05-31 | 2017-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR111841A1 true AR111841A1 (es) | 2019-08-21 |
Family
ID=64455572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP180101445A AR111841A1 (es) | 2017-05-31 | 2018-05-31 | ANILLOS 5-5 FUSIONADOS COMO INHIBIDORES DE C5a |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US10683294B2 (es) |
| EP (1) | EP3630774B1 (es) |
| JP (1) | JP7141129B2 (es) |
| KR (1) | KR102586710B1 (es) |
| CN (1) | CN111032658B (es) |
| AR (1) | AR111841A1 (es) |
| AU (1) | AU2018277523B2 (es) |
| CA (1) | CA3064025A1 (es) |
| ES (1) | ES2934507T3 (es) |
| IL (1) | IL270842B2 (es) |
| MA (1) | MA48800A (es) |
| MX (1) | MX391392B (es) |
| TW (1) | TWI813570B (es) |
| WO (1) | WO2018222601A1 (es) |
| ZA (1) | ZA201907755B (es) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA48800A (fr) | 2017-05-31 | 2020-04-08 | Chemocentryx Inc | Cycles 5-5 fusionnés utilisés en tant qu'inhibiteurs de c5a |
| WO2018222598A1 (en) | 2017-05-31 | 2018-12-06 | Chemocentryx, Inc. | 6-5 FUSED RINGS AS C5a INHIBITORS |
| AU2018388657C1 (en) | 2017-12-22 | 2023-03-23 | Chemocentryx, Inc. | Diaryl substituted 5,5-fused ring compounds as C5aR inhibitors |
| SG11202005791QA (en) * | 2017-12-22 | 2020-07-29 | Chemocentryx Inc | DIARYL SUBSTITUTED 6,5-FUSED RING COMPOUNDS AS C5aR INHIBITORS |
| AR114464A1 (es) | 2018-04-02 | 2020-09-09 | Chemocentryx Inc | PROFÁRMACOS DE ANTAGONISTAS DE C5aR BICÍCLICOS FUSIONADOS |
| WO2021007386A1 (en) | 2019-07-10 | 2021-01-14 | Chemocentryx, Inc. | Indanes as pd-l1 inhibitors |
| CN112300169B (zh) * | 2019-07-26 | 2022-03-04 | 上海美迪西生物医药股份有限公司 | 吡咯并吡唑类衍生物、其制备方法及其在医药上的应用 |
| PH12022550877A1 (en) | 2019-10-16 | 2023-03-27 | Chemocentryx Inc | Heteroaryl-biphenyl amines for the treatment of pd-l1 diseases |
| BR112022006018A2 (pt) | 2019-10-16 | 2022-07-12 | Chemocentryx Inc | Heteroaril-bifenil amidas para o tratamento de doenças relacionadas à pd-l1 |
| JP2023542789A (ja) * | 2020-09-28 | 2023-10-12 | シチュアン ケルン-バイオテック バイオファーマシューティカル カンパニー リミテッド | ピラゾール化合物並びにその調製方法及び使用 |
| CA3192880A1 (en) | 2020-10-28 | 2022-05-05 | Chemocentryx, Inc. | Methods of treating hidradenitis suppurativa |
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| DE60143041D1 (de) | 2000-08-10 | 2010-10-21 | Pfizer Italia Srl | Bizyklische pyrazole wirksam als kinase inhibitoren, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
| ATE404553T1 (de) | 2000-09-29 | 2008-08-15 | Neurogen Corp | Hochaffine kleinmolekülige c5a-rezeptor- modulatoren |
| SE524438C2 (sv) | 2000-10-05 | 2004-08-10 | Magnus Georg Goertz | Fjärrstyrt dörrelaterat låsarrangemang, första och andra datorpogramprodukt, bärande medium och ett datorlösbart medium |
| JP4196678B2 (ja) | 2001-04-26 | 2008-12-17 | 味の素株式会社 | 複素環化合物 |
| ITMI20012025A1 (it) | 2001-09-28 | 2003-03-28 | Dompe Spa | Sali di ammonio quaternari di omega-amminoalchilammidi di acidi r 2-aril-propionici e composizioni farmaceutiche che li contengono |
| CA2479930A1 (en) | 2002-03-28 | 2003-10-09 | Neurogen Corporation | Substituted tetrahydroisoquinolines as c5a receptor modulators |
| EP1487796A4 (en) | 2002-03-28 | 2005-11-16 | Neurogen Corp | SUBSTITUTED BIARYLAMIDES AS MODULATORS OF THE C5A RECEPTOR |
| CA2480082A1 (en) | 2002-03-29 | 2003-10-16 | Neurogen Corporation | Combination therapy for the treatment of conditions with pathogenic inflammatory components |
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| US7169775B2 (en) | 2002-08-21 | 2007-01-30 | Neurogen Corporation | Amino methyl imidazoles as C5a receptor modulators |
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| US7145012B2 (en) | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
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| AU2003902354A0 (en) | 2003-05-15 | 2003-05-29 | Harkin, Denis W. | Treatment of haemorrhagic shock |
| WO2005007087A2 (en) | 2003-07-03 | 2005-01-27 | Neurogen Corporation | Substituted (heterocycloalkyl)methyl azole derivatives as c5a receptor modulators |
| WO2006042102A2 (en) | 2004-10-05 | 2006-04-20 | Neurogen Corporation | Pyrrolo-pyridine, pyrrolo-pyrimidine and related heterocyclic compounds |
| US7598255B2 (en) | 2005-08-04 | 2009-10-06 | Janssen Pharmaceutica Nv | Pyrimidine compounds as serotonin receptor modulators |
| US20070112015A1 (en) | 2005-10-28 | 2007-05-17 | Chemocentryx, Inc. | Substituted dihydropyridines and methods of use |
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| US20110275639A1 (en) | 2008-12-22 | 2011-11-10 | Chemocentryx, Inc. | C5aR ANTAGONISTS |
| DK2585064T3 (en) | 2010-06-24 | 2017-07-24 | Chemocentryx Inc | C5aR antagonists |
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| CN103421006B (zh) | 2013-08-18 | 2016-06-22 | 上海师范大学 | 2,3,5,7-四取代二氢吡唑并六氢吡啶衍生物及其制备方法和应用 |
| GB201321746D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
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| MA48800A (fr) | 2017-05-31 | 2020-04-08 | Chemocentryx Inc | Cycles 5-5 fusionnés utilisés en tant qu'inhibiteurs de c5a |
| WO2018222598A1 (en) | 2017-05-31 | 2018-12-06 | Chemocentryx, Inc. | 6-5 FUSED RINGS AS C5a INHIBITORS |
| SG11202005791QA (en) | 2017-12-22 | 2020-07-29 | Chemocentryx Inc | DIARYL SUBSTITUTED 6,5-FUSED RING COMPOUNDS AS C5aR INHIBITORS |
| AU2018388657C1 (en) | 2017-12-22 | 2023-03-23 | Chemocentryx, Inc. | Diaryl substituted 5,5-fused ring compounds as C5aR inhibitors |
| AR114464A1 (es) | 2018-04-02 | 2020-09-09 | Chemocentryx Inc | PROFÁRMACOS DE ANTAGONISTAS DE C5aR BICÍCLICOS FUSIONADOS |
-
2018
- 2018-05-29 MA MA048800A patent/MA48800A/fr unknown
- 2018-05-29 US US15/991,747 patent/US10683294B2/en active Active
- 2018-05-29 EP EP18809125.0A patent/EP3630774B1/en active Active
- 2018-05-29 KR KR1020197038670A patent/KR102586710B1/ko active Active
- 2018-05-29 ES ES18809125T patent/ES2934507T3/es active Active
- 2018-05-29 CN CN201880036650.8A patent/CN111032658B/zh active Active
- 2018-05-29 MX MX2019014292A patent/MX391392B/es unknown
- 2018-05-29 CA CA3064025A patent/CA3064025A1/en active Pending
- 2018-05-29 AU AU2018277523A patent/AU2018277523B2/en active Active
- 2018-05-29 JP JP2019565826A patent/JP7141129B2/ja active Active
- 2018-05-29 WO PCT/US2018/034908 patent/WO2018222601A1/en not_active Ceased
- 2018-05-31 TW TW107118603A patent/TWI813570B/zh active
- 2018-05-31 AR ARP180101445A patent/AR111841A1/es unknown
-
2019
- 2019-11-21 IL IL270842A patent/IL270842B2/en unknown
- 2019-11-22 ZA ZA2019/07755A patent/ZA201907755B/en unknown
-
2020
- 2020-05-04 US US16/865,648 patent/US11479553B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20180346471A1 (en) | 2018-12-06 |
| IL270842B2 (en) | 2023-05-01 |
| EP3630774B1 (en) | 2022-11-23 |
| MX391392B (es) | 2025-03-21 |
| AU2018277523A1 (en) | 2019-12-05 |
| CN111032658A (zh) | 2020-04-17 |
| JP7141129B2 (ja) | 2022-09-22 |
| AU2018277523B2 (en) | 2022-06-23 |
| IL270842B1 (en) | 2023-01-01 |
| EP3630774A4 (en) | 2020-10-07 |
| KR20200013720A (ko) | 2020-02-07 |
| CN111032658B (zh) | 2022-12-20 |
| ES2934507T3 (es) | 2023-02-22 |
| BR112019025230A2 (pt) | 2020-06-16 |
| MA48800A (fr) | 2020-04-08 |
| ZA201907755B (en) | 2023-05-31 |
| TWI813570B (zh) | 2023-09-01 |
| EP3630774A1 (en) | 2020-04-08 |
| JP2020522483A (ja) | 2020-07-30 |
| TW201902897A (zh) | 2019-01-16 |
| RU2019142985A (ru) | 2021-06-30 |
| CA3064025A1 (en) | 2018-12-06 |
| KR102586710B1 (ko) | 2023-10-10 |
| US11479553B2 (en) | 2022-10-25 |
| WO2018222601A1 (en) | 2018-12-06 |
| MX2019014292A (es) | 2022-04-07 |
| US20210009594A1 (en) | 2021-01-14 |
| RU2019142985A3 (es) | 2021-09-03 |
| IL270842A (en) | 2020-01-30 |
| US10683294B2 (en) | 2020-06-16 |
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