RU2018123714A - 1,3,4-тиадиазольные соединения и их применение в лечении рака - Google Patents
1,3,4-тиадиазольные соединения и их применение в лечении рака Download PDFInfo
- Publication number
- RU2018123714A RU2018123714A RU2018123714A RU2018123714A RU2018123714A RU 2018123714 A RU2018123714 A RU 2018123714A RU 2018123714 A RU2018123714 A RU 2018123714A RU 2018123714 A RU2018123714 A RU 2018123714A RU 2018123714 A RU2018123714 A RU 2018123714A
- Authority
- RU
- Russia
- Prior art keywords
- methoxy
- acetamide
- amino
- thiadiazol
- pyridazin
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title claims 5
- 201000011510 cancer Diseases 0.000 title claims 5
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 17
- -1 1,2,4-triazin-3-yl Chemical group 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 14
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 2
- ASGBEFFYGLHCBE-BEFAXECRSA-N (2S)-2-(3,5-dimethoxyphenyl)-2-ethoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound COC=1C=C(C=C(C=1)OC)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)OCC ASGBEFFYGLHCBE-BEFAXECRSA-N 0.000 claims 1
- ORRGLFGRVLUXNY-CJNGLKHVSA-N (2S)-2-(3,5-dimethoxyphenyl)-2-methoxy-N-[5-[[(3R)-1-(1,2,4-triazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound COC=1C=C(C=C(C=1)OC)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CN=1)OC ORRGLFGRVLUXNY-CJNGLKHVSA-N 0.000 claims 1
- DXYFFQSFEMTYKX-ZBFHGGJFSA-N (2S)-2-[3-(3,3-difluoroazetidin-1-yl)phenyl]-2-methoxy-N-[5-[[(3R)-1-(1,2,4-triazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC1(CN(C1)C=1C=C(C=CC=1)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CN=1)OC)F DXYFFQSFEMTYKX-ZBFHGGJFSA-N 0.000 claims 1
- IXAKTBDCLYIDBZ-QAPCUYQASA-N (2S)-2-[3-(3,3-difluoroazetidin-1-yl)phenyl]-2-methoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC1(CN(C1)C=1C=C(C=CC=1)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)OC)F IXAKTBDCLYIDBZ-QAPCUYQASA-N 0.000 claims 1
- ZHRNCBVUEKDLAI-UZLBHIALSA-N (2S)-2-[3-(3-fluoroazetidin-1-yl)-5-methoxyphenyl]-2-methoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC1CN(C1)C=1C=C(C=C(C=1)OC)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)OC ZHRNCBVUEKDLAI-UZLBHIALSA-N 0.000 claims 1
- NSGZZBXIXXUHJV-WBVHZDCISA-N (2S)-2-[3-(3-fluoroazetidin-1-yl)phenyl]-2-methoxy-N-[5-[[(3R)-1-(1,2,4-triazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC1CN(C1)C=1C=C(C=CC=1)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CN=1)OC NSGZZBXIXXUHJV-WBVHZDCISA-N 0.000 claims 1
- ZDCKWVSAJLNKEB-APWZRJJASA-N (2S)-2-[3-(3-fluoroazetidin-1-yl)phenyl]-2-methoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC1CN(C1)C=1C=C(C=CC=1)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)OC ZDCKWVSAJLNKEB-APWZRJJASA-N 0.000 claims 1
- SIFSZFVWICOXGZ-BEFAXECRSA-N (2S)-2-[4-fluoro-3-(3-fluoroazetidin-1-yl)phenyl]-2-methoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC1=C(C=C(C=C1)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)OC)N1CC(C1)F SIFSZFVWICOXGZ-BEFAXECRSA-N 0.000 claims 1
- RXRILZDMSDDVGK-QRWLVFNGSA-N (2S)-2-[4-fluoro-3-(3-methoxyazetidin-1-yl)phenyl]-2-methoxy-N-[5-[(3R)-3-(pyridazin-3-ylamino)pyrrolidin-1-yl]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC1=C(C=C(C=C1)[C@@H](C(=O)NC=1SC(=NN=1)N1C[C@@H](CC1)NC=1N=NC=CC=1)OC)N1CC(C1)OC RXRILZDMSDDVGK-QRWLVFNGSA-N 0.000 claims 1
- WDDBMFLLFAMIRF-WBMJQRKESA-N (2S)-2-[4-fluoro-3-(trifluoromethoxy)phenyl]-2-methoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC1=C(C=C(C=C1)[C@@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)OC)OC(F)(F)F WDDBMFLLFAMIRF-WBMJQRKESA-N 0.000 claims 1
- RZACPCSTHBDOLY-PBHICJAKSA-N (2S)-2-ethoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]-2-[3-(trifluoromethoxy)phenyl]acetamide Chemical compound C(C)O[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)C1=CC(=CC=C1)OC(F)(F)F RZACPCSTHBDOLY-PBHICJAKSA-N 0.000 claims 1
- JAXWZAXQAUTYLQ-QAPCUYQASA-N (2S)-2-methoxy-2-[3-(3-methoxyazetidin-1-yl)phenyl]-N-[5-[[(3R)-1-(1,2,4-triazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound CO[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CN=1)C1=CC(=CC=C1)N1CC(C1)OC JAXWZAXQAUTYLQ-QAPCUYQASA-N 0.000 claims 1
- SMLCGOSBZPGHOV-UTKZUKDTSA-N (2S)-2-methoxy-2-[3-(3-methoxyazetidin-1-yl)phenyl]-N-[5-[[(3R)-1-(6-methylpyridazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound CO[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC(=CC=1)C)C1=CC(=CC=C1)N1CC(C1)OC SMLCGOSBZPGHOV-UTKZUKDTSA-N 0.000 claims 1
- YNGDVDDWQYYAAN-UZLBHIALSA-N (2S)-2-methoxy-2-[3-(3-methoxyazetidin-1-yl)phenyl]-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound CO[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)C1=CC(=CC=C1)N1CC(C1)OC YNGDVDDWQYYAAN-UZLBHIALSA-N 0.000 claims 1
- MHCDCRNHIYHNIK-MJGOQNOKSA-N (2S)-2-methoxy-2-[3-(oxetan-3-yl)phenyl]-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound CO[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)C1=CC(=CC=C1)C1COC1 MHCDCRNHIYHNIK-MJGOQNOKSA-N 0.000 claims 1
- BVXKPJNFBXKDMN-QRWLVFNGSA-N (2S)-N-[5-[[(3R)-1-(6-fluoropyridazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]-2-methoxy-2-[3-(3-methoxyazetidin-1-yl)phenyl]acetamide Chemical compound FC1=CC=C(N=N1)N1C[C@@H](CC1)NC1=NN=C(S1)NC([C@H](C1=CC(=CC=C1)N1CC(C1)OC)OC)=O BVXKPJNFBXKDMN-QRWLVFNGSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052731 fluorine Chemical group 0.000 claims 1
- 239000011737 fluorine Chemical group 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
-
- 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
- C07D417/14—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 three 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
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562260789P | 2015-11-30 | 2015-11-30 | |
| US62/260,789 | 2015-11-30 | ||
| PCT/EP2016/079250 WO2017093299A1 (en) | 2015-11-30 | 2016-11-30 | 1,3,4-thiadiazole compounds and their use in treating cancer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2018123714A true RU2018123714A (ru) | 2020-01-09 |
Family
ID=57485461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2018123714A RU2018123714A (ru) | 2015-11-30 | 2016-11-30 | 1,3,4-тиадиазольные соединения и их применение в лечении рака |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US10323028B2 (OSRAM) |
| EP (1) | EP3383873B1 (OSRAM) |
| JP (1) | JP6999550B2 (OSRAM) |
| KR (1) | KR20180083942A (OSRAM) |
| CN (1) | CN108349966B (OSRAM) |
| AR (1) | AR106874A1 (OSRAM) |
| AU (1) | AU2016363718B2 (OSRAM) |
| BR (1) | BR112018010806A2 (OSRAM) |
| CA (1) | CA3005495C (OSRAM) |
| CL (1) | CL2018001407A1 (OSRAM) |
| CO (1) | CO2018006928A2 (OSRAM) |
| EA (1) | EA201891241A1 (OSRAM) |
| ES (1) | ES2914333T3 (OSRAM) |
| IL (1) | IL259510A (OSRAM) |
| MX (1) | MX2018006532A (OSRAM) |
| NI (1) | NI201800064A (OSRAM) |
| PH (1) | PH12018501131A1 (OSRAM) |
| RU (1) | RU2018123714A (OSRAM) |
| SG (1) | SG11201803810XA (OSRAM) |
| SV (1) | SV2018005702A (OSRAM) |
| TN (1) | TN2018000127A1 (OSRAM) |
| TW (1) | TW201733587A (OSRAM) |
| WO (1) | WO2017093299A1 (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201520959D0 (en) | 2015-11-27 | 2016-01-13 | Astrazeneca Ab And Cancer Res Technology Ltd | Bis-pyridazine compounds and their use in treating cancer |
| US10323028B2 (en) | 2015-11-30 | 2019-06-18 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| TW201730188A (zh) | 2015-11-30 | 2017-09-01 | 阿斯特捷利康公司 | 1,3,4-噻二唑化合物及其在治療癌症中之用途 |
| TW201731511A (zh) * | 2015-11-30 | 2017-09-16 | 阿斯特捷利康公司 | １，３，４-噻二唑化合物及其在治療癌症中之用途 |
| JP7275053B2 (ja) * | 2017-06-13 | 2023-05-17 | メッドシャイン ディスカバリー インコーポレイテッド | Ｇｌｓ１阻害剤としての化合物 |
| US11230544B1 (en) | 2018-10-16 | 2022-01-25 | Medshine Discovery Inc. | Substituted 1,3,4-thiadiazoles as GLS1 inhibitors |
| WO2025196446A1 (en) * | 2024-03-22 | 2025-09-25 | Sitryx Therapeutics Limited | Thiadiazoles as glutaminase 1 inhibitors |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6451828B1 (en) * | 2000-08-10 | 2002-09-17 | Elan Pharmaceuticals, Inc. | Selective inhibition of glutaminase by bis-thiadiazoles |
| EA026656B1 (ru) * | 2011-11-21 | 2017-05-31 | Калитера Байосайенсиз Инк. | Гетероциклические ингибиторы глютаминазы |
| EP3954686A1 (en) * | 2012-11-16 | 2022-02-16 | Calithera Biosciences, Inc. | Heterocyclic glutaminase inhibitors |
| US9029531B2 (en) | 2012-11-22 | 2015-05-12 | Agios Pharmaceuticals, Inc. | Compounds and their methods of use |
| KR20160100407A (ko) | 2014-01-06 | 2016-08-23 | 리젠 파마슈티컬스 소시에떼 아노님 | 신규한 글루타미나제의 저해제 |
| US20150258082A1 (en) * | 2014-03-14 | 2015-09-17 | Francesco Parlati | Combination therapy with glutaminase inhibitors |
| GB201409624D0 (en) | 2014-05-30 | 2014-07-16 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| GB201520959D0 (en) | 2015-11-27 | 2016-01-13 | Astrazeneca Ab And Cancer Res Technology Ltd | Bis-pyridazine compounds and their use in treating cancer |
| US10323028B2 (en) | 2015-11-30 | 2019-06-18 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| TW201730188A (zh) * | 2015-11-30 | 2017-09-01 | 阿斯特捷利康公司 | 1,3,4-噻二唑化合物及其在治療癌症中之用途 |
| TW201731511A (zh) | 2015-11-30 | 2017-09-16 | 阿斯特捷利康公司 | １，３，４-噻二唑化合物及其在治療癌症中之用途 |
-
2016
- 2016-11-29 US US15/363,030 patent/US10323028B2/en active Active
- 2016-11-29 TW TW105139337A patent/TW201733587A/zh unknown
- 2016-11-30 SG SG11201803810XA patent/SG11201803810XA/en unknown
- 2016-11-30 BR BR112018010806A patent/BR112018010806A2/pt not_active Application Discontinuation
- 2016-11-30 KR KR1020187018472A patent/KR20180083942A/ko not_active Withdrawn
- 2016-11-30 RU RU2018123714A patent/RU2018123714A/ru not_active Application Discontinuation
- 2016-11-30 WO PCT/EP2016/079250 patent/WO2017093299A1/en not_active Ceased
- 2016-11-30 CA CA3005495A patent/CA3005495C/en active Active
- 2016-11-30 EA EA201891241A patent/EA201891241A1/ru unknown
- 2016-11-30 MX MX2018006532A patent/MX2018006532A/es unknown
- 2016-11-30 TN TNP/2018/000127A patent/TN2018000127A1/en unknown
- 2016-11-30 AU AU2016363718A patent/AU2016363718B2/en active Active
- 2016-11-30 CN CN201680067245.3A patent/CN108349966B/zh active Active
- 2016-11-30 ES ES16806028T patent/ES2914333T3/es active Active
- 2016-11-30 EP EP16806028.3A patent/EP3383873B1/en active Active
- 2016-11-30 AR ARP160103663A patent/AR106874A1/es unknown
- 2016-11-30 JP JP2018526716A patent/JP6999550B2/ja active Active
-
2018
- 2018-05-22 IL IL259510A patent/IL259510A/en unknown
- 2018-05-24 CL CL2018001407A patent/CL2018001407A1/es unknown
- 2018-05-29 NI NI201800064A patent/NI201800064A/es unknown
- 2018-05-29 SV SV2018005702A patent/SV2018005702A/es unknown
- 2018-05-29 PH PH12018501131A patent/PH12018501131A1/en unknown
- 2018-06-29 CO CONC2018/0006928A patent/CO2018006928A2/es unknown
-
2019
- 2019-05-03 US US16/402,825 patent/US10981904B2/en active Active
-
2021
- 2021-04-15 US US17/231,164 patent/US11753405B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN108349966B (zh) | 2022-02-15 |
| AU2016363718A1 (en) | 2018-07-12 |
| WO2017093299A1 (en) | 2017-06-08 |
| US10981904B2 (en) | 2021-04-20 |
| IL259510A (en) | 2018-07-31 |
| EP3383873B1 (en) | 2022-03-09 |
| SG11201803810XA (en) | 2018-06-28 |
| PH12018501131A1 (en) | 2019-01-21 |
| CA3005495A1 (en) | 2017-06-08 |
| CO2018006928A2 (es) | 2018-10-10 |
| EP3383873A1 (en) | 2018-10-10 |
| SV2018005702A (es) | 2018-11-27 |
| JP6999550B2 (ja) | 2022-02-10 |
| EA201891241A1 (ru) | 2019-01-31 |
| ES2914333T3 (es) | 2022-06-09 |
| TW201733587A (zh) | 2017-10-01 |
| US20190389853A1 (en) | 2019-12-26 |
| TN2018000127A1 (en) | 2019-10-04 |
| MX2018006532A (es) | 2019-05-15 |
| US20170152255A1 (en) | 2017-06-01 |
| CL2018001407A1 (es) | 2018-10-12 |
| BR112018010806A2 (pt) | 2018-11-27 |
| NI201800064A (es) | 2018-10-18 |
| AR106874A1 (es) | 2018-02-28 |
| US20210246131A1 (en) | 2021-08-12 |
| CA3005495C (en) | 2023-12-12 |
| CN108349966A (zh) | 2018-07-31 |
| US11753405B2 (en) | 2023-09-12 |
| US10323028B2 (en) | 2019-06-18 |
| AU2016363718B2 (en) | 2019-11-14 |
| KR20180083942A (ko) | 2018-07-23 |
| JP2018535986A (ja) | 2018-12-06 |
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