EA037384B1 - Ингибиторы протеинкиназ - Google Patents
Ингибиторы протеинкиназ Download PDFInfo
- Publication number
- EA037384B1 EA037384B1 EA201992793A EA201992793A EA037384B1 EA 037384 B1 EA037384 B1 EA 037384B1 EA 201992793 A EA201992793 A EA 201992793A EA 201992793 A EA201992793 A EA 201992793A EA 037384 B1 EA037384 B1 EA 037384B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- quinazoline
- pyrido
- oxo
- carboxamide
- cyclohexyl
- Prior art date
Links
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
- 239000003909 protein kinase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
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- 101000970023 Homo sapiens NUAK family SNF1-like kinase 1 Proteins 0.000 claims description 28
- -1 N-cyclohexyl-2-cyclopropyl-11-oxo-11H-pyrido [2,1-b] quinazoline-6-carboxyamide Chemical compound 0.000 claims description 28
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- HWHQDEHKRIXJQN-UHFFFAOYSA-N quinazoline-6-carboxamide Chemical compound N1=CN=CC2=CC(C(=O)N)=CC=C21 HWHQDEHKRIXJQN-UHFFFAOYSA-N 0.000 claims description 20
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
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- 229910052731 fluorine Inorganic materials 0.000 claims description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
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- 230000006907 apoptotic process Effects 0.000 description 1
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- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 description 1
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- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- WLVKDFJTYKELLQ-UHFFFAOYSA-N cyclopropylboronic acid Chemical compound OB(O)C1CC1 WLVKDFJTYKELLQ-UHFFFAOYSA-N 0.000 description 1
- 230000003436 cytoskeletal effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 229950008830 decernotinib Drugs 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
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- 208000035475 disorder Diseases 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 230000008482 dysregulation Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000019439 energy homeostasis Effects 0.000 description 1
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- 230000007705 epithelial mesenchymal transition Effects 0.000 description 1
- 230000010437 erythropoiesis Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000002825 functional assay Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000007274 generation of a signal involved in cell-cell signaling Effects 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 231100001252 long-term toxicity Toxicity 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000004066 metabolic change Effects 0.000 description 1
- 230000006609 metabolic stress Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- OOKUTMZSIGOCSB-UHFFFAOYSA-N methyl 2-amino-5-(4-fluorophenyl)benzoate Chemical compound C1=C(N)C(C(=O)OC)=CC(C=2C=CC(F)=CC=2)=C1 OOKUTMZSIGOCSB-UHFFFAOYSA-N 0.000 description 1
- PNNRKISKHNTAHL-UHFFFAOYSA-N methyl 2-amino-5-thiophen-2-ylbenzoate Chemical compound C1=C(N)C(C(=O)OC)=CC(C=2SC=CC=2)=C1 PNNRKISKHNTAHL-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000009437 off-target effect Effects 0.000 description 1
- 108091008819 oncoproteins Proteins 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 229950005157 peficitinib Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 108091006106 transcriptional activators Proteins 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24C—DOMESTIC STOVES OR RANGES ; DETAILS OF DOMESTIC STOVES OR RANGES, OF GENERAL APPLICATION
- F24C7/00—Stoves or ranges heated by electric energy
- F24C7/08—Arrangement or mounting of control or safety devices
- F24C7/082—Arrangement or mounting of control or safety devices on ranges, e.g. control panels, illumination
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24C—DOMESTIC STOVES OR RANGES ; DETAILS OF DOMESTIC STOVES OR RANGES, OF GENERAL APPLICATION
- F24C7/00—Stoves or ranges heated by electric energy
- F24C7/08—Arrangement or mounting of control or safety devices
- F24C7/087—Arrangement or mounting of control or safety devices of electric circuits regulating heat
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES201730759 | 2017-06-01 | ||
| PCT/ES2018/070396 WO2018220252A1 (es) | 2017-06-01 | 2018-05-31 | Derivados de piridoquinazolina eficaces como inhibidores de proteína quinasa |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201992793A1 EA201992793A1 (ru) | 2020-03-26 |
| EA037384B1 true EA037384B1 (ru) | 2021-03-23 |
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| EA201992793A EA037384B1 (ru) | 2017-06-01 | 2018-05-31 | Ингибиторы протеинкиназ |
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| EP (1) | EP3632912B1 (enExample) |
| JP (1) | JP7110335B2 (enExample) |
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| CN (1) | CN111247143B (enExample) |
| AU (1) | AU2018278283B2 (enExample) |
| CY (1) | CY1124087T1 (enExample) |
| DK (1) | DK3632912T3 (enExample) |
| EA (1) | EA037384B1 (enExample) |
| ES (1) | ES2881960T3 (enExample) |
| HR (1) | HRP20210814T1 (enExample) |
| HU (1) | HUE054792T2 (enExample) |
| LT (1) | LT3632912T (enExample) |
| MX (1) | MX385475B (enExample) |
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| PT (1) | PT3632912T (enExample) |
| RS (1) | RS61833B1 (enExample) |
| SI (1) | SI3632912T1 (enExample) |
| SM (1) | SMT202100312T1 (enExample) |
| WO (1) | WO2018220252A1 (enExample) |
| ZA (1) | ZA201908372B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11978921B2 (en) | 2020-01-31 | 2024-05-07 | Lg Energy Solution, Ltd. | Method of manufacturing separator-composite electrode comprising multilayer-structured inorganic layer and separator-composite electrode manufactured thereby |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998023617A1 (en) * | 1996-11-26 | 1998-06-04 | American Cyanamid Company | Hetero-biaryl-pyridoquinazolinone derivatives as anti-cancer agents |
| WO2015143293A1 (en) * | 2014-03-20 | 2015-09-24 | The Johns Hopkins University | Compounds which inhibit rna polymerase, compositions including such compounds, and their use |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4551460A (en) | 1982-05-10 | 1985-11-05 | Hoffmann-La Roche Inc. | Pyrido[2,1-b]quinazoline derivatives useful as agents for treatment of allergic conditions and vascular disorders involving thrombosis |
| WO2005048953A2 (en) | 2003-11-13 | 2005-06-02 | Ambit Biosciences Corporation | Amide derivatives as kinase modulators |
| AU2008345225A1 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| KR101361027B1 (ko) | 2008-11-28 | 2014-02-11 | 코와 가부시키가이샤 | 피리딘-3-카르복시아미드 유도체 |
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2018
- 2018-05-31 RS RS20210545A patent/RS61833B1/sr unknown
- 2018-05-31 SM SM20210312T patent/SMT202100312T1/it unknown
- 2018-05-31 AU AU2018278283A patent/AU2018278283B2/en active Active
- 2018-05-31 LT LTEP18759146.6T patent/LT3632912T/lt unknown
- 2018-05-31 WO PCT/ES2018/070396 patent/WO2018220252A1/es not_active Ceased
- 2018-05-31 MX MX2019014436A patent/MX385475B/es unknown
- 2018-05-31 CN CN201880048531.4A patent/CN111247143B/zh active Active
- 2018-05-31 JP JP2020516962A patent/JP7110335B2/ja active Active
- 2018-05-31 DK DK18759146.6T patent/DK3632912T3/da active
- 2018-05-31 KR KR1020197038842A patent/KR102629854B1/ko active Active
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- 2018-05-31 EA EA201992793A patent/EA037384B1/ru unknown
- 2018-05-31 PL PL18759146T patent/PL3632912T3/pl unknown
- 2018-05-31 HR HRP20210814TT patent/HRP20210814T1/hr unknown
- 2018-05-31 SI SI201830289T patent/SI3632912T1/sl unknown
- 2018-05-31 HU HUE18759146A patent/HUE054792T2/hu unknown
- 2018-05-31 US US16/615,867 patent/US11021479B2/en active Active
- 2018-05-31 ES ES18759146T patent/ES2881960T3/es active Active
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2019
- 2019-12-13 ZA ZA2019/08372A patent/ZA201908372B/en unknown
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2021
- 2021-05-20 CY CY20211100437T patent/CY1124087T1/el unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998023617A1 (en) * | 1996-11-26 | 1998-06-04 | American Cyanamid Company | Hetero-biaryl-pyridoquinazolinone derivatives as anti-cancer agents |
| WO2015143293A1 (en) * | 2014-03-20 | 2015-09-24 | The Johns Hopkins University | Compounds which inhibit rna polymerase, compositions including such compounds, and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| SMT202100312T1 (it) | 2021-07-12 |
| EA201992793A1 (ru) | 2020-03-26 |
| US11021479B2 (en) | 2021-06-01 |
| EP3632912B1 (en) | 2021-03-17 |
| PT3632912T (pt) | 2021-06-02 |
| HUE054792T2 (hu) | 2021-09-28 |
| RS61833B1 (sr) | 2021-06-30 |
| CN111247143B (zh) | 2022-07-05 |
| MX385475B (es) | 2025-03-18 |
| PL3632912T3 (pl) | 2021-09-06 |
| ZA201908372B (en) | 2021-04-28 |
| BR112019024892A2 (pt) | 2020-06-16 |
| US20200148676A1 (en) | 2020-05-14 |
| CA3066009A1 (en) | 2018-12-06 |
| KR102629854B1 (ko) | 2024-01-25 |
| JP2020521817A (ja) | 2020-07-27 |
| WO2018220252A1 (es) | 2018-12-06 |
| AU2018278283A1 (en) | 2019-12-19 |
| KR20200011990A (ko) | 2020-02-04 |
| SI3632912T1 (sl) | 2021-08-31 |
| JP7110335B2 (ja) | 2022-08-01 |
| MX2019014436A (es) | 2020-02-10 |
| CN111247143A (zh) | 2020-06-05 |
| HRP20210814T1 (hr) | 2021-06-25 |
| EP3632912A1 (en) | 2020-04-08 |
| LT3632912T (lt) | 2021-06-10 |
| CY1124087T1 (el) | 2022-05-27 |
| AU2018278283B2 (en) | 2021-06-17 |
| DK3632912T3 (da) | 2021-05-10 |
| ES2881960T3 (es) | 2021-11-30 |
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