CN108368046B - 哌啶酮甲酰肽2受体和甲酰肽1受体激动剂 - Google Patents
哌啶酮甲酰肽2受体和甲酰肽1受体激动剂 Download PDFInfo
- Publication number
- CN108368046B CN108368046B CN201680072467.4A CN201680072467A CN108368046B CN 108368046 B CN108368046 B CN 108368046B CN 201680072467 A CN201680072467 A CN 201680072467A CN 108368046 B CN108368046 B CN 108368046B
- Authority
- CN
- China
- Prior art keywords
- alkyl
- phenyl
- substituted
- urea
- oxopiperidin
- Prior art date
- 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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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/45—Non condensed piperidines, e.g. piperocaine having oxo groups directly attached to the heterocyclic ring, e.g. cycloheximide
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
-
- 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
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C07D405/10—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 aromatic rings
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562265885P | 2015-12-10 | 2015-12-10 | |
| US62/265885 | 2015-12-10 | ||
| PCT/US2016/065504 WO2017100390A1 (en) | 2015-12-10 | 2016-12-08 | Piperidinone formyl peptide 2 receptor and formyl peptide 1 receptor agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108368046A CN108368046A (zh) | 2018-08-03 |
| CN108368046B true CN108368046B (zh) | 2022-01-14 |
Family
ID=57590898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201680072467.4A Active CN108368046B (zh) | 2015-12-10 | 2016-12-08 | 哌啶酮甲酰肽2受体和甲酰肽1受体激动剂 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US10717708B2 (https=) |
| EP (1) | EP3414227B1 (https=) |
| JP (1) | JP6811241B2 (https=) |
| KR (1) | KR102772801B1 (https=) |
| CN (1) | CN108368046B (https=) |
| AU (1) | AU2016366211B2 (https=) |
| BR (1) | BR112018011046A2 (https=) |
| CA (1) | CA3007972A1 (https=) |
| EA (1) | EA034227B1 (https=) |
| ES (1) | ES2901471T3 (https=) |
| IL (1) | IL259791B (https=) |
| MX (1) | MX386387B (https=) |
| SG (1) | SG11201804589TA (https=) |
| WO (1) | WO2017100390A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2018005756A (es) * | 2015-11-24 | 2018-08-01 | Squibb Bristol Myers Co | Ubicacion como objetivo del receptor 2 de formilo-peptido/receptor de lipoxina a4 (fpr2/alx) para el tratamiento de enfermedades cardiacas. |
| JP6811241B2 (ja) | 2015-12-10 | 2021-01-13 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | ピペリジノンホルミルペプチド受容体２およびホルミルペプチド受容体１アゴニスト |
| EP3634958B1 (en) | 2017-06-09 | 2021-07-21 | Bristol-Myers Squibb Company | Cyclopropyl urea formyl peptide 2 receptor and formyl peptide 1 receptor agonists |
| WO2018227065A1 (en) * | 2017-06-09 | 2018-12-13 | Bristol-Myers Squibb Company | Piperidinone formyl peptide 2 receptor and formyl peptide 1 receptor agonists |
| KR102615099B1 (ko) | 2017-06-09 | 2023-12-15 | 브리스톨-마이어스 스큅 컴퍼니 | 아릴 헤테로시클릭 피페리디논 포르밀 펩티드 2 수용체 및 포르밀 펩티드 1 수용체 효능제 |
| KR102615095B1 (ko) * | 2017-06-09 | 2023-12-15 | 브리스톨-마이어스 스큅 컴퍼니 | 피페리디논 포르밀 펩티드 2 수용체 효능제 |
| KR102803660B1 (ko) * | 2018-03-05 | 2025-05-02 | 브리스톨-마이어스 스큅 컴퍼니 | 페닐피롤리디논 포르밀 펩티드 2 수용체 효능제 |
| AR114383A1 (es) * | 2018-03-09 | 2020-08-26 | Gruenenthal Gmbh | Piperidinas o piperidonas sustituidas con urea y fenilo |
| CN113166134B (zh) | 2018-11-26 | 2024-06-14 | 百时美施贵宝公司 | 作为甲酰肽2受体激动剂的吡咯烷酮衍生物 |
| EP3986903B1 (en) * | 2019-06-18 | 2023-05-10 | Bristol-Myers Squibb Company | Biaryl dialkyl phosphine oxide fpr2 agonists |
| EP3789378A1 (en) * | 2019-09-06 | 2021-03-10 | Grünenthal GmbH | Piperidines or piperidones substituted with urea and heteroaryl |
| CA3185263A1 (en) | 2020-07-09 | 2022-01-13 | James A. Johnson | Pyrazolone formyl peptide 2 receptor agonists |
| KR20230051525A (ko) * | 2020-08-12 | 2023-04-18 | 브리스톨-마이어스 스큅 컴퍼니 | 옥소피롤리딘 우레아 fpr2 효능제 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006063113A2 (en) * | 2004-12-07 | 2006-06-15 | Portola Pharmaceuticals, Inc. | Ureas as factor xa inhibitors |
| WO2015079692A1 (ja) * | 2013-11-28 | 2015-06-04 | 杏林製薬株式会社 | ウレア誘導体、またはその薬理学的に許容される塩 |
| WO2016189876A1 (en) * | 2015-05-27 | 2016-12-01 | Kyorin Pharmaceutical Co., Ltd. | Urea derivative or pharmacologically acceptable salt thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002060859A2 (en) | 2000-12-20 | 2002-08-08 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| KR102223384B1 (ko) * | 2013-03-06 | 2021-03-05 | 알러간, 인코포레이티드 | 피부 질환 치료용 포르밀 펩티드 수용체 2의 항진제의 용도 |
| JP6746614B2 (ja) | 2015-05-27 | 2020-08-26 | 杏林製薬株式会社 | ウレア誘導体、またはその薬理学的に許容される塩 |
| MX2018005756A (es) | 2015-11-24 | 2018-08-01 | Squibb Bristol Myers Co | Ubicacion como objetivo del receptor 2 de formilo-peptido/receptor de lipoxina a4 (fpr2/alx) para el tratamiento de enfermedades cardiacas. |
| JP6811241B2 (ja) | 2015-12-10 | 2021-01-13 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | ピペリジノンホルミルペプチド受容体２およびホルミルペプチド受容体１アゴニスト |
| WO2018227065A1 (en) | 2017-06-09 | 2018-12-13 | Bristol-Myers Squibb Company | Piperidinone formyl peptide 2 receptor and formyl peptide 1 receptor agonists |
| EP3634958B1 (en) | 2017-06-09 | 2021-07-21 | Bristol-Myers Squibb Company | Cyclopropyl urea formyl peptide 2 receptor and formyl peptide 1 receptor agonists |
| KR102615099B1 (ko) | 2017-06-09 | 2023-12-15 | 브리스톨-마이어스 스큅 컴퍼니 | 아릴 헤테로시클릭 피페리디논 포르밀 펩티드 2 수용체 및 포르밀 펩티드 1 수용체 효능제 |
| KR102615095B1 (ko) | 2017-06-09 | 2023-12-15 | 브리스톨-마이어스 스큅 컴퍼니 | 피페리디논 포르밀 펩티드 2 수용체 효능제 |
-
2016
- 2016-12-08 JP JP2018530001A patent/JP6811241B2/ja active Active
- 2016-12-08 AU AU2016366211A patent/AU2016366211B2/en not_active Ceased
- 2016-12-08 CN CN201680072467.4A patent/CN108368046B/zh active Active
- 2016-12-08 US US15/776,933 patent/US10717708B2/en active Active
- 2016-12-08 BR BR112018011046A patent/BR112018011046A2/pt active Search and Examination
- 2016-12-08 EP EP16816564.5A patent/EP3414227B1/en active Active
- 2016-12-08 WO PCT/US2016/065504 patent/WO2017100390A1/en not_active Ceased
- 2016-12-08 EA EA201891143A patent/EA034227B1/ru not_active IP Right Cessation
- 2016-12-08 KR KR1020187019246A patent/KR102772801B1/ko active Active
- 2016-12-08 CA CA3007972A patent/CA3007972A1/en not_active Abandoned
- 2016-12-08 SG SG11201804589TA patent/SG11201804589TA/en unknown
- 2016-12-08 ES ES16816564T patent/ES2901471T3/es active Active
- 2016-12-08 MX MX2018006635A patent/MX386387B/es unknown
-
2018
- 2018-06-04 IL IL259791A patent/IL259791B/en unknown
-
2020
- 2020-06-11 US US16/898,889 patent/US11530183B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006063113A2 (en) * | 2004-12-07 | 2006-06-15 | Portola Pharmaceuticals, Inc. | Ureas as factor xa inhibitors |
| WO2015079692A1 (ja) * | 2013-11-28 | 2015-06-04 | 杏林製薬株式会社 | ウレア誘導体、またはその薬理学的に許容される塩 |
| WO2016189876A1 (en) * | 2015-05-27 | 2016-12-01 | Kyorin Pharmaceutical Co., Ltd. | Urea derivative or pharmacologically acceptable salt thereof |
Non-Patent Citations (1)
| Title |
|---|
| Design of a Bioactive Small Molecule That Targets the Myotonic Dystrophy Type 1 RNA via an RNA Motif-Ligand Database and Chemical Similarity Searching;Raman Parkesh等;《Journal of the American Chemical Society》;20120202;第134卷;第4731-4742页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP6811241B2 (ja) | 2021-01-13 |
| IL259791A (en) | 2018-07-31 |
| EP3414227A1 (en) | 2018-12-19 |
| EA034227B1 (ru) | 2020-01-20 |
| MX2018006635A (es) | 2018-08-01 |
| US11530183B2 (en) | 2022-12-20 |
| EA201891143A1 (ru) | 2018-11-30 |
| CN108368046A (zh) | 2018-08-03 |
| AU2016366211B2 (en) | 2021-06-17 |
| EP3414227B1 (en) | 2021-11-24 |
| KR20180091876A (ko) | 2018-08-16 |
| SG11201804589TA (en) | 2018-06-28 |
| CA3007972A1 (en) | 2017-06-15 |
| AU2016366211A1 (en) | 2018-07-26 |
| JP2018536687A (ja) | 2018-12-13 |
| MX386387B (es) | 2025-03-18 |
| KR102772801B1 (ko) | 2025-02-24 |
| IL259791B (en) | 2021-08-31 |
| US10717708B2 (en) | 2020-07-21 |
| US20180327358A1 (en) | 2018-11-15 |
| WO2017100390A1 (en) | 2017-06-15 |
| ES2901471T3 (es) | 2022-03-22 |
| US20200299237A1 (en) | 2020-09-24 |
| BR112018011046A2 (pt) | 2018-11-21 |
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