CA2970550C - Pyridazinone macrocycles as irak inhibitors and uses thereof - Google Patents
Pyridazinone macrocycles as irak inhibitors and uses thereof Download PDFInfo
- Publication number
- CA2970550C CA2970550C CA2970550A CA2970550A CA2970550C CA 2970550 C CA2970550 C CA 2970550C CA 2970550 A CA2970550 A CA 2970550A CA 2970550 A CA2970550 A CA 2970550A CA 2970550 C CA2970550 C CA 2970550C
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- CA
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- Prior art keywords
- compound
- disease
- crr
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- irak
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- 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.)
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-
- 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
- C07D487/12—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 three hetero rings
- C07D487/18—Bridged 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
- C07D498/22—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 four or more hetero rings
-
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-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
- A61K31/495—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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/504—Pyridazines; Hydrogenated pyridazines forming part of bridged ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P31/04—Antibacterial agents
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- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D471/18—Bridged systems
-
- 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
- C07D471/22—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 systems contains four or more hetero rings
-
- 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
- C07D487/22—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 four or more hetero rings
-
- 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
- C07D498/12—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 three hetero rings
- C07D498/16—Peri-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
- C07D498/12—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 three hetero rings
- C07D498/18—Bridged systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Dermatology (AREA)
- Oncology (AREA)
- Nutrition Science (AREA)
- Communicable Diseases (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562112793P | 2015-02-06 | 2015-02-06 | |
| US62/112,793 | 2015-02-06 | ||
| PCT/US2016/016708 WO2016127024A1 (en) | 2015-02-06 | 2016-02-05 | Pyridazinone macrocycles as irak inhibitors and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2970550A1 CA2970550A1 (en) | 2016-08-11 |
| CA2970550C true CA2970550C (en) | 2023-09-19 |
Family
ID=55436166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2970550A Active CA2970550C (en) | 2015-02-06 | 2016-02-05 | Pyridazinone macrocycles as irak inhibitors and uses thereof |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US9624246B2 (OSRAM) |
| EP (1) | EP3253763B1 (OSRAM) |
| JP (1) | JP6920202B2 (OSRAM) |
| KR (1) | KR102551597B1 (OSRAM) |
| CN (1) | CN107428765B (OSRAM) |
| AU (1) | AU2016215184B2 (OSRAM) |
| BR (1) | BR112017014970B1 (OSRAM) |
| CA (1) | CA2970550C (OSRAM) |
| ES (1) | ES2841452T3 (OSRAM) |
| IL (1) | IL253519B (OSRAM) |
| MX (1) | MX380929B (OSRAM) |
| RU (1) | RU2708066C2 (OSRAM) |
| SG (1) | SG11201704651UA (OSRAM) |
| WO (1) | WO2016127024A1 (OSRAM) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2841452T3 (es) * | 2015-02-06 | 2021-07-08 | Merck Patent Gmbh | Macrociclos de piridazinona como inhibidores de IRAK y sus usos |
| TWI794171B (zh) | 2016-05-11 | 2023-03-01 | 美商滬亞生物國際有限公司 | Ｈｄａｃ抑制劑與ｐｄ-ｌ１抑制劑之組合治療 |
| TWI808055B (zh) | 2016-05-11 | 2023-07-11 | 美商滬亞生物國際有限公司 | Hdac 抑制劑與 pd-1 抑制劑之組合治療 |
| TWI733982B (zh) | 2017-02-16 | 2021-07-21 | 美商基利科學股份有限公司 | 吡咯并[1,2-b]嗒衍生物 |
| WO2019111218A1 (en) | 2017-12-08 | 2019-06-13 | Cadila Healthcare Limited | Novel heterocyclic compounds as irak4 inhibitors |
| WO2019120267A1 (zh) * | 2017-12-22 | 2019-06-27 | 成都先导药物开发股份有限公司 | 一种咪唑并[1,2-b]哒嗪大环类激酶抑制剂 |
| MX2020009234A (es) * | 2018-04-05 | 2020-10-12 | Merck Patent Gmbh | Compuestos de heteroarilo como inhibidores de cinasas asociadas con receptores de interleucina-1 (irak) tipo ii y usos de los mismos. |
| TWI721483B (zh) | 2018-07-13 | 2021-03-11 | 美商基利科學股份有限公司 | 吡咯并[1,2-b]嗒𠯤衍生物 |
| JP7164705B2 (ja) | 2018-08-13 | 2022-11-01 | ギリアード サイエンシーズ， インコーポレイテッド | ＩＲＡＫ４阻害剤としてのピロロ［１，２－ｂ］ピリダジン誘導体 |
| US11572362B2 (en) | 2018-08-13 | 2023-02-07 | Gilead Sciences, Inc. | Pyrrolo[1,2-b]pyridazine derivatives |
| TWI727392B (zh) | 2018-08-13 | 2021-05-11 | 美商基利科學股份有限公司 | 噻二唑irak4抑制劑 |
| US11998534B2 (en) * | 2020-02-12 | 2024-06-04 | Eubulus Biotherapeutics Inc. | GPX4 inhibitor in combination with anticancer agent for treating proliferative disease |
| CN111603471B (zh) * | 2020-06-24 | 2021-07-09 | 山东省科学院生物研究所 | 一种邻二氮杂环化合物在制备抑制tlr4受体的药物中的用途 |
| EP4223368B1 (en) | 2020-09-30 | 2025-05-21 | Asahi Kasei Pharma Corporation | Macrocyclic compounds incorporating piperidine and quinoline or qunaxoline as irak-4 inhibitors for the treatment of inflammatory conditions |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000247959A (ja) * | 1999-02-26 | 2000-09-12 | Kowa Co | ピリダジン−３−オン誘導体及びこれを含有する医薬 |
| JP2010138073A (ja) * | 2007-03-30 | 2010-06-24 | Taisho Pharmaceutical Co Ltd | ピコリン酸アミド化合物 |
| US8703768B2 (en) * | 2010-06-09 | 2014-04-22 | Hoffmann-La Roche Inc. | Nitrogen containing heteroaryl compounds |
| US9586948B2 (en) * | 2012-10-08 | 2017-03-07 | Merck Sharp & Dohme Corp. | Inhibitors of IRAK4 activity |
| RU2660435C2 (ru) * | 2013-02-07 | 2018-07-06 | Мерк Патент Гмбх | Макроциклические производные пиридазинона |
| HUE032863T2 (en) * | 2013-02-07 | 2017-11-28 | Merck Patent Gmbh | Piridazinonamid derivatives |
| ES2841452T3 (es) * | 2015-02-06 | 2021-07-08 | Merck Patent Gmbh | Macrociclos de piridazinona como inhibidores de IRAK y sus usos |
-
2016
- 2016-02-05 ES ES16706471T patent/ES2841452T3/es active Active
- 2016-02-05 SG SG11201704651UA patent/SG11201704651UA/en unknown
- 2016-02-05 CA CA2970550A patent/CA2970550C/en active Active
- 2016-02-05 CN CN201680018681.1A patent/CN107428765B/zh not_active Expired - Fee Related
- 2016-02-05 RU RU2017130761A patent/RU2708066C2/ru active
- 2016-02-05 AU AU2016215184A patent/AU2016215184B2/en not_active Ceased
- 2016-02-05 WO PCT/US2016/016708 patent/WO2016127024A1/en not_active Ceased
- 2016-02-05 KR KR1020177020262A patent/KR102551597B1/ko active Active
- 2016-02-05 US US15/016,584 patent/US9624246B2/en not_active Expired - Fee Related
- 2016-02-05 BR BR112017014970-2A patent/BR112017014970B1/pt not_active IP Right Cessation
- 2016-02-05 JP JP2017539435A patent/JP6920202B2/ja not_active Expired - Fee Related
- 2016-02-05 MX MX2017009624A patent/MX380929B/es unknown
- 2016-02-05 EP EP16706471.6A patent/EP3253763B1/en active Active
-
2017
- 2017-03-06 US US15/450,463 patent/US10517872B2/en active Active
- 2017-07-17 IL IL253519A patent/IL253519B/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP6920202B2 (ja) | 2021-08-18 |
| BR112017014970A2 (pt) | 2018-03-27 |
| AU2016215184B2 (en) | 2020-11-12 |
| AU2016215184A1 (en) | 2017-06-29 |
| IL253519B (en) | 2021-01-31 |
| IL253519A0 (en) | 2017-09-28 |
| RU2708066C2 (ru) | 2019-12-04 |
| MX2017009624A (es) | 2017-11-20 |
| US20160229871A1 (en) | 2016-08-11 |
| KR102551597B1 (ko) | 2023-07-05 |
| NZ732527A (en) | 2022-03-25 |
| KR20170113551A (ko) | 2017-10-12 |
| RU2017130761A3 (OSRAM) | 2019-07-17 |
| RU2017130761A (ru) | 2019-03-06 |
| MX380929B (es) | 2025-03-12 |
| JP2018505166A (ja) | 2018-02-22 |
| CN107428765B (zh) | 2020-12-29 |
| WO2016127024A1 (en) | 2016-08-11 |
| BR112017014970B1 (pt) | 2022-11-16 |
| US20170173019A1 (en) | 2017-06-22 |
| EP3253763A1 (en) | 2017-12-13 |
| US9624246B2 (en) | 2017-04-18 |
| HK1246287A1 (zh) | 2018-09-07 |
| CA2970550A1 (en) | 2016-08-11 |
| EP3253763B1 (en) | 2020-09-30 |
| SG11201704651UA (en) | 2017-07-28 |
| ES2841452T3 (es) | 2021-07-08 |
| CN107428765A (zh) | 2017-12-01 |
| US10517872B2 (en) | 2019-12-31 |
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