EA036518B1 - Производные 9h-пирролодипиридина - Google Patents
Производные 9h-пирролодипиридина Download PDFInfo
- Publication number
- EA036518B1 EA036518B1 EA201791733A EA201791733A EA036518B1 EA 036518 B1 EA036518 B1 EA 036518B1 EA 201791733 A EA201791733 A EA 201791733A EA 201791733 A EA201791733 A EA 201791733A EA 036518 B1 EA036518 B1 EA 036518B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- pyrrolo
- dipyridine
- methyl
- dipyridin
- mmol
- Prior art date
Links
- 239000012216 imaging agent Substances 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- -1 benzyl methyl group Chemical group 0.000 claims description 314
- 150000001875 compounds Chemical class 0.000 claims description 163
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 66
- 239000000203 mixture Substances 0.000 claims description 60
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 30
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- 239000011737 fluorine Substances 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 23
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- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000004481 post-translational protein modification Effects 0.000 description 1
- 102000035123 post-translationally modified proteins Human genes 0.000 description 1
- 108091005626 post-translationally modified proteins Proteins 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
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- 235000004252 protein component Nutrition 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 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
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 229930185107 quinolinone Chemical class 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000002739 subcortical effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical compound I[I-]I WRTMQOHKMFDUKX-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 210000004885 white matter Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07D471/12—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 three hetero rings
- C07D471/14—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
- A61K31/435—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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0455—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0459—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0463—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- 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
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15153448 | 2015-02-02 | ||
| PCT/EP2016/051993 WO2016124508A1 (en) | 2015-02-02 | 2016-01-29 | 9h-pyrrolo-dipyridine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201791733A1 EA201791733A1 (ru) | 2018-01-31 |
| EA036518B1 true EA036518B1 (ru) | 2020-11-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201791733A EA036518B1 (ru) | 2015-02-02 | 2016-01-29 | Производные 9h-пирролодипиридина |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US20180022748A1 (OSRAM) |
| EP (1) | EP3253762B1 (OSRAM) |
| JP (1) | JP6579670B2 (OSRAM) |
| KR (1) | KR102621513B1 (OSRAM) |
| CN (1) | CN107207508B (OSRAM) |
| AU (1) | AU2016214537B2 (OSRAM) |
| BR (1) | BR112017016311A2 (OSRAM) |
| CA (1) | CA2973648C (OSRAM) |
| CL (1) | CL2017001923A1 (OSRAM) |
| DK (1) | DK3253762T3 (OSRAM) |
| EA (1) | EA036518B1 (OSRAM) |
| ES (1) | ES2875734T3 (OSRAM) |
| IL (1) | IL253381B (OSRAM) |
| MX (1) | MX378155B (OSRAM) |
| MY (1) | MY191590A (OSRAM) |
| SG (1) | SG11201705727TA (OSRAM) |
| WO (1) | WO2016124508A1 (OSRAM) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2247558T5 (pl) | 2008-02-14 | 2024-10-14 | Eli Lilly And Company | Nowe środki obrazujące do wykrywania czynnościowych zaburzeń neurologicznych |
| SG11201705727TA (en) * | 2015-02-02 | 2017-08-30 | Ucb Biopharma Sprl | 9h-pyrrolo-dipyridine derivatives |
| CN115650982A (zh) * | 2016-07-22 | 2023-01-31 | Ac免疫有限公司 | 用于成像tau蛋白聚集体的化合物 |
| EP3487545A1 (en) | 2016-07-22 | 2019-05-29 | AC Immune S.A. | Compounds for imaging tau protein aggregates |
| ES2847903T3 (es) * | 2016-09-09 | 2021-08-04 | Hoffmann La Roche | Procedimiento para la preparación de 2-(6-nitropiridin-3-il)-9H-dipirido[2,3-b;3',4'-d]pirrol |
| KR20230127371A (ko) * | 2016-11-01 | 2023-08-31 | 아비나스 오퍼레이션스, 인코포레이티드 | 타우(Tau)-단백질 표적화 프로탁(PROTAC) 및 관련 사용 방법 |
| US11660287B2 (en) | 2017-06-02 | 2023-05-30 | Fujifilm Toyama Chemical Co., Ltd. | Agent for preventing or treating spinocerebellar ataxia |
| MX393052B (es) | 2017-06-02 | 2025-03-24 | Fujifilm Toyama Chemical Co Ltd | Agente para prevenir o tratar atrofia cerebral. |
| WO2018221731A1 (ja) * | 2017-06-02 | 2018-12-06 | 富山化学工業株式会社 | タウオパチー予防または治療剤 |
| EP3636262A4 (en) | 2017-06-02 | 2020-06-10 | FUJIFILM Toyama Chemical Co., Ltd. | AGENT FOR PREVENTING OR TREATING ALZHEIMER-LIKE DEMENTIA |
| BR112019024983A2 (pt) | 2017-06-02 | 2020-06-23 | Fujifilm Toyama Chemical Co., Ltd. | Agente para reduzir a quantidade de proteína b amiloide |
| EP3705121B1 (en) | 2017-10-30 | 2023-08-30 | FUJIFILM Toyama Chemical Co., Ltd. | Emopamil binding protein binding agent and use thereof |
| CN111868062B (zh) * | 2018-01-24 | 2023-07-07 | Ac免疫有限公司 | 制备显像化合物的方法 |
| EP3743426A1 (en) * | 2018-01-24 | 2020-12-02 | AC Immune SA | Azacarboline compounds for the detection of tau aggregates |
| EP3743423A1 (en) | 2018-01-24 | 2020-12-02 | AC Immune SA | Gamma-carboline compounds for the detection of tau aggregates |
| US11912699B2 (en) | 2019-07-17 | 2024-02-27 | Arvinas Operations, Inc. | Tau-protein targeting compounds and associated |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008132454A1 (en) * | 2007-04-26 | 2008-11-06 | Ge Healthcare Limited | Carbolines and their use as imaging agents |
| WO2009102498A1 (en) * | 2008-02-14 | 2009-08-20 | Siemens Medical Solutions Usa, Inc. | Novel imaging agents for detecting neurological dysfunction |
| WO2013176698A1 (en) * | 2012-05-22 | 2013-11-28 | Eli Lilly And Company | Carboline and carbazole based imaging agents for detecting neurological dysfunction |
| WO2015052105A1 (en) * | 2013-10-08 | 2015-04-16 | F. Hoffmann-La Roche Ag | Diazacarbazole derivatives as tau-pet-ligands |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1268771A (en) | 1968-03-15 | 1972-03-29 | Glaxo Lab Ltd | Azacarbazoles |
| JP5557849B2 (ja) * | 2008-12-19 | 2014-07-23 | ブリストル−マイヤーズ スクイブ カンパニー | カルバゾールおよびカルボリンキナーゼ阻害剤 |
| US20160115162A1 (en) * | 2013-05-31 | 2016-04-28 | The General Hospital Corporation | Radiosynthesis of Tau Radiopharmaceuticals |
| US9774356B2 (en) * | 2013-07-24 | 2017-09-26 | Telefonaktiebolaget Lm Ericsson (Publ) | Method and apparatus relating to reception of radio signals |
| WO2015110263A1 (en) * | 2014-01-21 | 2015-07-30 | Ac Immune Sa | Carbazole and carboline compounds for use in the diagnosis, treatment, alleviation or prevention of disorders associated with amyloid or amyolid-like proteins |
| SG11201705727TA (en) * | 2015-02-02 | 2017-08-30 | Ucb Biopharma Sprl | 9h-pyrrolo-dipyridine derivatives |
-
2016
- 2016-01-29 SG SG11201705727TA patent/SG11201705727TA/en unknown
- 2016-01-29 BR BR112017016311A patent/BR112017016311A2/pt not_active Application Discontinuation
- 2016-01-29 DK DK16702121.1T patent/DK3253762T3/da active
- 2016-01-29 KR KR1020177024371A patent/KR102621513B1/ko active Active
- 2016-01-29 US US15/547,980 patent/US20180022748A1/en not_active Abandoned
- 2016-01-29 EA EA201791733A patent/EA036518B1/ru not_active IP Right Cessation
- 2016-01-29 MY MYPI2017702668A patent/MY191590A/en unknown
- 2016-01-29 MX MX2017009505A patent/MX378155B/es unknown
- 2016-01-29 AU AU2016214537A patent/AU2016214537B2/en active Active
- 2016-01-29 EP EP16702121.1A patent/EP3253762B1/en active Active
- 2016-01-29 JP JP2017540724A patent/JP6579670B2/ja active Active
- 2016-01-29 ES ES16702121T patent/ES2875734T3/es active Active
- 2016-01-29 CN CN201680008314.3A patent/CN107207508B/zh active Active
- 2016-01-29 CA CA2973648A patent/CA2973648C/en active Active
- 2016-01-29 WO PCT/EP2016/051993 patent/WO2016124508A1/en not_active Ceased
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2017
- 2017-07-10 IL IL253381A patent/IL253381B/en active IP Right Grant
- 2017-07-27 CL CL2017001923A patent/CL2017001923A1/es unknown
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2020
- 2020-01-22 US US16/749,537 patent/US11312716B2/en active Active
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2022
- 2022-03-21 US US17/700,075 patent/US12006316B2/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008132454A1 (en) * | 2007-04-26 | 2008-11-06 | Ge Healthcare Limited | Carbolines and their use as imaging agents |
| WO2009102498A1 (en) * | 2008-02-14 | 2009-08-20 | Siemens Medical Solutions Usa, Inc. | Novel imaging agents for detecting neurological dysfunction |
| WO2013176698A1 (en) * | 2012-05-22 | 2013-11-28 | Eli Lilly And Company | Carboline and carbazole based imaging agents for detecting neurological dysfunction |
| WO2015052105A1 (en) * | 2013-10-08 | 2015-04-16 | F. Hoffmann-La Roche Ag | Diazacarbazole derivatives as tau-pet-ligands |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107207508A (zh) | 2017-09-26 |
| CL2017001923A1 (es) | 2018-02-16 |
| CA2973648C (en) | 2023-09-26 |
| EA201791733A1 (ru) | 2018-01-31 |
| US20220213103A1 (en) | 2022-07-07 |
| JP6579670B2 (ja) | 2019-09-25 |
| MX2017009505A (es) | 2017-11-02 |
| US12006316B2 (en) | 2024-06-11 |
| BR112017016311A2 (pt) | 2018-03-27 |
| KR102621513B1 (ko) | 2024-01-04 |
| CA2973648A1 (en) | 2016-08-11 |
| MX378155B (es) | 2025-03-10 |
| ES2875734T3 (es) | 2021-11-11 |
| CN107207508B (zh) | 2020-02-28 |
| EP3253762B1 (en) | 2021-05-05 |
| EP3253762A1 (en) | 2017-12-13 |
| JP2018503673A (ja) | 2018-02-08 |
| MY191590A (en) | 2022-06-30 |
| AU2016214537A1 (en) | 2017-08-03 |
| SG11201705727TA (en) | 2017-08-30 |
| US11312716B2 (en) | 2022-04-26 |
| IL253381A0 (en) | 2017-09-28 |
| US20180022748A1 (en) | 2018-01-25 |
| WO2016124508A1 (en) | 2016-08-11 |
| DK3253762T3 (da) | 2021-07-19 |
| IL253381B (en) | 2020-10-29 |
| KR20170113607A (ko) | 2017-10-12 |
| AU2016214537B2 (en) | 2018-05-10 |
| US20210047326A1 (en) | 2021-02-18 |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
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