HRP20210062T1 - Kristal spoja s aktivnošću inhibiranja jak - Google Patents
Kristal spoja s aktivnošću inhibiranja jak Download PDFInfo
- Publication number
- HRP20210062T1 HRP20210062T1 HRP20210062TT HRP20210062T HRP20210062T1 HR P20210062 T1 HRP20210062 T1 HR P20210062T1 HR P20210062T T HRP20210062T T HR P20210062TT HR P20210062 T HRP20210062 T HR P20210062T HR P20210062 T1 HRP20210062 T1 HR P20210062T1
- Authority
- HR
- Croatia
- Prior art keywords
- crystal
- compound
- diffraction
- pyrazolo
- thiazol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 10
- 239000013078 crystal Substances 0.000 title claims 8
- 230000002401 inhibitory effect Effects 0.000 title 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 6
- 229910052802 copper Inorganic materials 0.000 claims 6
- 239000010949 copper Substances 0.000 claims 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims 6
- 230000005855 radiation Effects 0.000 claims 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims 3
- BFEXLLUICRTAHW-AWEZNQCLSA-N N-[1-[6-[[(1S)-1-cyclopropylethyl]amino]-2-pyrazolo[5,1-b][1,3]thiazol-7-ylpyrimidine-4-carbonyl]piperidin-4-yl]cyclopropanecarboxamide Chemical compound C1(CC1)[C@H](C)NC1=CC(=NC(=N1)C=1C=NN2C=1SC=C2)C(=O)N1CCC(CC1)NC(=O)C1CC1 BFEXLLUICRTAHW-AWEZNQCLSA-N 0.000 claims 1
- AYQCQOVDKCVGCI-OAHLLOKOSA-N N-[1-[6-[[(2R)-3,3-dimethylbutan-2-yl]amino]-2-pyrazolo[5,1-b][1,3]thiazol-7-ylpyrimidine-4-carbonyl]piperidin-4-yl]cyclopropanecarboxamide Chemical compound CC([C@@H](C)NC1=CC(=NC(=N1)C=1C=NN2C=1SC=C2)C(=O)N1CCC(CC1)NC(=O)C1CC1)(C)C AYQCQOVDKCVGCI-OAHLLOKOSA-N 0.000 claims 1
- GVJXJONZFOQVDX-AWEZNQCLSA-N ethyl N-[1-[6-[[(1S)-1-cyclopropylethyl]amino]-2-pyrazolo[5,1-b][1,3]thiazol-7-ylpyrimidine-4-carbonyl]piperidin-4-yl]carbamate Chemical compound C1(CC1)[C@H](C)NC1=CC(=NC(=N1)C=1C=NN2C=1SC=C2)C(=O)N1CCC(CC1)NC(OCC)=O GVJXJONZFOQVDX-AWEZNQCLSA-N 0.000 claims 1
- HKUQUNWLBNUYJP-ZDUSSCGKSA-N methyl N-[1-[6-[[(1S)-1-cyclopropylethyl]amino]-2-pyrazolo[5,1-b][1,3]thiazol-7-ylpyrimidine-4-carbonyl]piperidin-4-yl]carbamate Chemical group C1(CC1)[C@H](C)NC1=CC(=NC(=N1)C=1C=NN2C=1SC=C2)C(=O)N1CCC(CC1)NC(OC)=O HKUQUNWLBNUYJP-ZDUSSCGKSA-N 0.000 claims 1
- BOHNHVVPOFTMJA-CYBMUJFWSA-N methyl N-[1-[6-[[(2R)-butan-2-yl]amino]-2-pyrazolo[5,1-b][1,3]thiazol-7-ylpyrimidine-4-carbonyl]piperidin-4-yl]carbamate Chemical group C[C@H](CC)NC1=CC(=NC(=N1)C=1C=NN2C=1SC=C2)C(=O)N1CCC(CC1)NC(OC)=O BOHNHVVPOFTMJA-CYBMUJFWSA-N 0.000 claims 1
- BOHNHVVPOFTMJA-ZDUSSCGKSA-N methyl N-[1-[6-[[(2S)-butan-2-yl]amino]-2-pyrazolo[5,1-b][1,3]thiazol-7-ylpyrimidine-4-carbonyl]piperidin-4-yl]carbamate Chemical group C[C@@H](CC)NC1=CC(=NC(=N1)C=1C=NN2C=1SC=C2)C(=O)N1CCC(CC1)NC(OC)=O BOHNHVVPOFTMJA-ZDUSSCGKSA-N 0.000 claims 1
Classifications
-
- 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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory 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
-
- 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]
-
- 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
-
- 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
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Transplantation (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (15)
1. Spoj, naznačen time što je monohidrat tosilata metil-[1-({6-[(2S)-butan-2-ilamino]-2-(pirazolo[5,1-b][1,3]tiazol-7-il)pirimidin-4-il}karbonil)piperidin-4-il]karbamata.
2. Kristal spoja u skladu s patentnim zahtjevom 1, naznačen time što ima uzorak difrakcije rendgenskih zraka na prahu dobiven uz pomoć zračenja Kα s bakra, koji sadrži difrakcijske maksimume pod difrakcijskim kutovima (2θ) od 12,6°, 13,3°, 17,3°, 20,0°, 20,4°, 21,3° i 22,3°.
3. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s patentnim zahtjevom 1 ili 2 kao aktivni sastojak.
4. Spoj, naznačen time što je monohidrat tosilata metil-[1-({6-[(2R)-butan-2-ilamino]-2-(pirazolo[5,1-b][1,3]tiazol-7-il)pirimidin-4-il}karbonil)piperidin-4-il]karbamata.
5. Kristal spoja u skladu s patentnim zahtjevom 4, naznačen time što ima uzorak difrakcije rendgenskih zraka na prahu dobiven uz pomoć zračenja Kα s bakra, koji sadrži difrakcijske maksimume pod difrakcijskim kutovima (2θ) od 12,6°, 13,3°, 17,3°, 20,0°, 20,4°, 21,3° i 22,3°.
6. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s patentnim zahtjevom 4 ili 5 kao aktivni sastojak.
7. Spoj, naznačen time što je monohidrat tosilata metil-(1-{[6-{[(1S)-1-ciklopropiletil]amino}-2-(pirazolo[5,1-b][1,3]tiazol-7-il)pirimidin-4-il]karbonil}piperidin-4-il)karbamata.
8. Kristal spoja u skladu s patentnim zahtjevom 7, naznačen time što ima uzorak difrakcije rendgenskih zraka na prahu dobiven uz pomoć zračenja Kα s bakra, koji sadrži difrakcijske maksimume pod difrakcijskim kutovima (2θ) od 12,6°, 13,3°, 17,2°, 20,6° i 21,8°.
9. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s patentnim zahtjevom 7 ili 8 kao aktivni sastojak.
10. Kristal etil-(1-{[6-{[(1S)-1-ciklopropiletil]amino}-2-(pirazolo[5,1-b][1,3]tiazol-7-il)pirimidin-4-il]karbonil}piperidin-4-il)karbamata, naznačen time što ima uzorak difrakcije rendgenskih zraka na prahu dobiven uz pomoć zračenja Kα s bakra, koji sadrži difrakcijske maksimume pod difrakcijskim kutovima (2θ) od 12,0°, 13,8°, 15,0°, 16,0°, 19,4°, 20,9° i 21,9°.
11. Farmaceutski pripravak, naznačen time što sadrži kristal u skladu s patentnim zahtjevom 10 kao aktivni sastojak.
12. Kristal N-(1-{[6-{[(1S)-1-ciklopropiletil]amino}-2-(pirazolo[5,1-b][1,3]tiazol-7-il)pirimidin-4-il]karbonil}piperidin-4-il)ciklopropankarboksamida, naznačen time što ima uzorak difrakcije rendgenskih zraka na prahu dobiven uz pomoć zračenja Kα s bakra, koji sadrži difrakcijske maksimume pod difrakcijskim kutovima (2θ) od 11,1°, 12,9°, 15,4°, 17,8°, 21,2° i 22,3°.
13. Farmaceutski pripravak, naznačen time što sadrži kristal u skladu s patentnim zahtjevom 12 kao aktivni sastojak.
14. Kristal N-(1-{[6-{[(2R)-3,3-dimetilbutan-2-il]amino}-2-(pirazolo[5,1-b][1,3]tiazol-7-il)pirimidin-4-il]karbonil}piperidin-4-il)ciklopropankarboksamida, naznačen time što ima uzorak difrakcije rendgenskih zraka na prahu dobiven uz pomoć zračenja Kα s bakra, koji sadrži difrakcijske maksimume pod difrakcijskim kutovima (2θ) od 10,6°, 13,0°, 14,6°, 17,4°, 17,7°, 21,3° i 21,7°.
15. Farmaceutski pripravak, naznačen time što sadrži kristal u skladu s patentnim zahtjevom 14 kao aktivni sastojak.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016039315 | 2016-03-01 | ||
| EP17759943.8A EP3424930B1 (en) | 2016-03-01 | 2017-02-28 | Crystal of compound having jak-inhibiting activity |
| PCT/JP2017/007594 WO2017150477A1 (ja) | 2016-03-01 | 2017-02-28 | Ｊａｋ阻害作用を有する化合物の結晶 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20210062T1 true HRP20210062T1 (hr) | 2021-03-05 |
Family
ID=59743962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20210062TT HRP20210062T1 (hr) | 2016-03-01 | 2021-01-13 | Kristal spoja s aktivnošću inhibiranja jak |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US10822350B2 (hr) |
| EP (1) | EP3424930B1 (hr) |
| JP (1) | JP6791239B2 (hr) |
| KR (1) | KR102653231B1 (hr) |
| CN (1) | CN108699082B (hr) |
| BR (1) | BR112018016523B1 (hr) |
| CA (2) | CA3206830A1 (hr) |
| CY (1) | CY1123607T1 (hr) |
| DK (1) | DK3424930T3 (hr) |
| ES (1) | ES2844978T3 (hr) |
| HR (1) | HRP20210062T1 (hr) |
| HU (1) | HUE051615T2 (hr) |
| LT (1) | LT3424930T (hr) |
| MX (1) | MX2018010334A (hr) |
| PL (1) | PL3424930T3 (hr) |
| PT (1) | PT3424930T (hr) |
| RS (1) | RS61238B1 (hr) |
| RU (1) | RU2705721C1 (hr) |
| SI (1) | SI3424930T1 (hr) |
| TW (1) | TWI712604B (hr) |
| WO (1) | WO2017150477A1 (hr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI712604B (zh) * | 2016-03-01 | 2020-12-11 | 日商日本新藥股份有限公司 | 具jak抑制作用之化合物之結晶 |
| CA3192219A1 (en) * | 2020-09-14 | 2022-03-17 | Heiko HABERMULLER | N-heterocyclic compounds used as nitrification inhibitor |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3600390A1 (de) | 1986-01-09 | 1987-07-16 | Hoechst Ag | Diarylalkyl-substituierte alkylamine, verfahren zu ihrer herstellung, ihre verwendung sowie sie enthaltende arzneimittel |
| BRPI0506817A (pt) | 2004-01-12 | 2007-05-29 | Cytopia Res Pty Ltd | inibidores seletivos de quinase |
| KR20080063809A (ko) * | 2005-09-30 | 2008-07-07 | 버텍스 파마슈티칼스 인코포레이티드 | 야누스 키나아제의 억제제로서 유용한 데아자퓨린 |
| EP2537849A3 (en) | 2006-01-17 | 2013-04-03 | Vertex Pharmaceuticals, Inc. | Azaindoles useful as inhibitors of janus kinases |
| ES2602577T3 (es) | 2008-03-11 | 2017-02-21 | Incyte Holdings Corporation | Derivados de azetidina y ciclobutano como inhibidores de JAK |
| JO3041B1 (ar) | 2008-07-25 | 2016-09-05 | Galapagos Nv | مركبات جديدة مفيدة لمعالجة الأمراض التنكسية والالتهابية |
| WO2010070060A1 (en) * | 2008-12-19 | 2010-06-24 | Nerviano Medical Sciences S.R.L. | Bicyclic pyrazoles as protein kinase inhibitors |
| TWI462920B (zh) * | 2009-06-26 | 2014-12-01 | 葛萊伯格有限公司 | 用於治療退化性及發炎疾病之新穎化合物 |
| ES2461967T3 (es) | 2009-12-18 | 2014-05-21 | Pfizer Inc. | Compuestos de pirrolo[2,3-d]pirimidina |
| EP2338888A1 (en) | 2009-12-24 | 2011-06-29 | Almirall, S.A. | Imidazopyridine derivatives as JAK inhibitors |
| JP2011136925A (ja) | 2009-12-28 | 2011-07-14 | Dainippon Sumitomo Pharma Co Ltd | 含窒素二環性化合物 |
| KR20140015162A (ko) | 2010-01-12 | 2014-02-06 | 에프. 호프만-라 로슈 아게 | 트라이사이클릭 헤테로사이클릭 화합물, 조성물 및 이의 사용 방법 |
| UY33213A (es) | 2010-02-18 | 2011-09-30 | Almirall Sa | Derivados de pirazol como inhibidores de jak |
| WO2012022045A1 (en) | 2010-08-20 | 2012-02-23 | Hutchison Medipharma Limited | Pyrrolopyrimidine compounds and uses thereof |
| WO2012037132A1 (en) | 2010-09-14 | 2012-03-22 | Exelixis, Inc. | Phtalazine derivatives as jak1 inhibitors |
| WO2012054364A2 (en) | 2010-10-22 | 2012-04-26 | Merck Sharp & Dohme Corp. | Bicyclic diamines as janus kinase inhibitors |
| WO2012085176A1 (en) | 2010-12-23 | 2012-06-28 | F. Hoffmann-La Roche Ag | Tricyclic pyrazinone compounds, compositions and methods of use thereof as janus kinase inhibitors |
| WO2013025628A1 (en) * | 2011-08-15 | 2013-02-21 | Ligand Pharmaceuticals Incorporated | Janus kinase inhibitor compounds and methods |
| TWI679205B (zh) * | 2014-09-02 | 2019-12-11 | 日商日本新藥股份有限公司 | 吡唑并噻唑化合物及醫藥 |
| TWI712604B (zh) * | 2016-03-01 | 2020-12-11 | 日商日本新藥股份有限公司 | 具jak抑制作用之化合物之結晶 |
-
2017
- 2017-02-08 TW TW106104074A patent/TWI712604B/zh active
- 2017-02-28 SI SI201730521T patent/SI3424930T1/sl unknown
- 2017-02-28 PT PT177599438T patent/PT3424930T/pt unknown
- 2017-02-28 US US16/077,889 patent/US10822350B2/en active Active
- 2017-02-28 CN CN201780014551.5A patent/CN108699082B/zh active Active
- 2017-02-28 JP JP2018503309A patent/JP6791239B2/ja active Active
- 2017-02-28 MX MX2018010334A patent/MX2018010334A/es unknown
- 2017-02-28 KR KR1020187027122A patent/KR102653231B1/ko active IP Right Grant
- 2017-02-28 BR BR112018016523-9A patent/BR112018016523B1/pt active IP Right Grant
- 2017-02-28 RU RU2018134041A patent/RU2705721C1/ru active
- 2017-02-28 WO PCT/JP2017/007594 patent/WO2017150477A1/ja active Application Filing
- 2017-02-28 DK DK17759943.8T patent/DK3424930T3/da active
- 2017-02-28 CA CA3206830A patent/CA3206830A1/en active Pending
- 2017-02-28 ES ES17759943T patent/ES2844978T3/es active Active
- 2017-02-28 LT LTEP17759943.8T patent/LT3424930T/lt unknown
- 2017-02-28 PL PL17759943T patent/PL3424930T3/pl unknown
- 2017-02-28 HU HUE17759943A patent/HUE051615T2/hu unknown
- 2017-02-28 CA CA3015464A patent/CA3015464C/en active Active
- 2017-02-28 EP EP17759943.8A patent/EP3424930B1/en active Active
- 2017-02-28 RS RS20201509A patent/RS61238B1/sr unknown
-
2020
- 2020-09-29 US US17/035,947 patent/US11377453B2/en active Active
- 2020-12-02 CY CY20201101142T patent/CY1123607T1/el unknown
-
2021
- 2021-01-13 HR HRP20210062TT patent/HRP20210062T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR102653231B1 (ko) | 2024-04-01 |
| WO2017150477A1 (ja) | 2017-09-08 |
| EP3424930B1 (en) | 2020-11-04 |
| US20190048023A1 (en) | 2019-02-14 |
| TWI712604B (zh) | 2020-12-11 |
| JPWO2017150477A1 (ja) | 2018-12-27 |
| EP3424930A4 (en) | 2019-07-10 |
| PL3424930T3 (pl) | 2021-05-04 |
| ES2844978T3 (es) | 2021-07-23 |
| LT3424930T (lt) | 2021-01-11 |
| SI3424930T1 (sl) | 2021-01-29 |
| TW201731855A (zh) | 2017-09-16 |
| CA3015464C (en) | 2024-04-23 |
| BR112018016523B1 (pt) | 2024-02-06 |
| RU2705721C1 (ru) | 2019-11-11 |
| CN108699082B (zh) | 2021-04-09 |
| US10822350B2 (en) | 2020-11-03 |
| CY1123607T1 (el) | 2022-03-24 |
| EP3424930A1 (en) | 2019-01-09 |
| BR112018016523A2 (pt) | 2018-12-26 |
| MX2018010334A (es) | 2018-11-09 |
| DK3424930T3 (da) | 2021-01-11 |
| PT3424930T (pt) | 2020-12-04 |
| HUE051615T2 (hu) | 2021-03-01 |
| RS61238B1 (sr) | 2021-01-29 |
| US20210017191A1 (en) | 2021-01-21 |
| JP6791239B2 (ja) | 2020-11-25 |
| KR20180116341A (ko) | 2018-10-24 |
| CN108699082A (zh) | 2018-10-23 |
| CA3206830A1 (en) | 2017-09-08 |
| US11377453B2 (en) | 2022-07-05 |
| CA3015464A1 (en) | 2017-09-08 |
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