HRP20211777T1 - Postupak u jednoj posudi za pripremu racemičnog nikotina reakcijom etil nikotinata s n-vinilpirolidonom u prisutnosti natrij etanolata ili kalij etanolata ili njihovih mješavina - Google Patents
Postupak u jednoj posudi za pripremu racemičnog nikotina reakcijom etil nikotinata s n-vinilpirolidonom u prisutnosti natrij etanolata ili kalij etanolata ili njihovih mješavina Download PDFInfo
- Publication number
- HRP20211777T1 HRP20211777T1 HRP20211777TT HRP20211777T HRP20211777T1 HR P20211777 T1 HRP20211777 T1 HR P20211777T1 HR P20211777T T HRP20211777T T HR P20211777TT HR P20211777 T HRP20211777 T HR P20211777T HR P20211777 T1 HRP20211777 T1 HR P20211777T1
- Authority
- HR
- Croatia
- Prior art keywords
- tartaric acid
- dibenzoyl
- reaction
- process according
- ethanolate
- Prior art date
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- XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 title claims 6
- 238000006243 chemical reaction Methods 0.000 title claims 4
- 239000000203 mixture Substances 0.000 title claims 4
- 229940064982 ethylnicotinate Drugs 0.000 title claims 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 title claims 2
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 title claims 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 title 1
- 238000005580 one pot reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 4
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- YONLFQNRGZXBBF-ZIAGYGMSSA-L (2r,3r)-2,3-dibenzoyloxybutanedioate Chemical compound O([C@@H](C(=O)[O-])[C@@H](OC(=O)C=1C=CC=CC=1)C([O-])=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-L 0.000 claims 2
- MYKUKUCHPMASKF-VIFPVBQESA-N (S)-nornicotine Chemical compound C1CCN[C@@H]1C1=CC=CN=C1 MYKUKUCHPMASKF-VIFPVBQESA-N 0.000 claims 2
- DUBOBNPDMCGUTR-UHFFFAOYSA-N 1-ethenyl-3-(pyridine-3-carbonyl)pyrrolidin-2-one Chemical compound C(C1=CN=CC=C1)(=O)C1C(N(CC1)C=C)=O DUBOBNPDMCGUTR-UHFFFAOYSA-N 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 2
- MYKUKUCHPMASKF-UHFFFAOYSA-N Nornicotine Natural products C1CCNC1C1=CC=CN=C1 MYKUKUCHPMASKF-UHFFFAOYSA-N 0.000 claims 2
- 239000003849 aromatic solvent Substances 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- DPNGWXJMIILTBS-UHFFFAOYSA-N dehydronornicotine Natural products C1CCN=C1C1=CC=CN=C1 DPNGWXJMIILTBS-UHFFFAOYSA-N 0.000 claims 2
- 235000019253 formic acid Nutrition 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 229930040373 Paraformaldehyde Natural products 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- 230000001035 methylating effect Effects 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 229920002866 paraformaldehyde Polymers 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 150000003892 tartrate salts Chemical class 0.000 claims 1
Classifications
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- 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
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- 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
- C07B2200/07—Optical isomers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Addiction (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Manufacture Of Tobacco Products (AREA)
Claims (12)
1. Postupak za pripremu spoja formule I-a, koji uključuje
[image]
(i) reakciju etil nikotinata i N-vinilpirolidona u prisutnosti alkoholne baze u 3-nikotinoil-1-vinilpirolidin-2-on;
(ii) reakciju 3-nikotinoil-1-vinilpirolidin-2-ona s kiselinom u miozmin;
(iii) redukciju miozmina u nornikotin korištenjem redukcijskog sredstva; i
(iv) metiliranje nornikotina da se dobije spoj formule Ia,
pri čemu je baza alkohola u koraku (i) alkoholat alkalnog metala odabran između natrijevog etanolata, kalijevog etanolata, i njihove mješavine, i
pri čemu se postupak provodi u jednoj posudi.
2. Postupak prema zahtjevu 1, naznačen time što se korak (i) provodi u prisutnosti aromatskog otapala.
3. Postupak prema zahtjevu 2, naznačen time što je aromatično otapalo benzen, toluen ili njihova mješavina.
4. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što se alkoholna baza dodaje u koraku (i) u količini između 1.4 i 2 ekvivalenta, na temelju 1 ekvivalenta etil nikotinata.
5. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što se korak (ii) provodi uporabom anorganske kiseline na temperaturi između 90 i 115°C, poželjno između 100 i 105°C.
6. Postupak prema zahtjevu 5, naznačen time što je anorganska kiselina HCl.
7. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što se korak (iv) provodi uporabom mravlje kiseline i paraformaldehida, ili mravlje kiseline i formaldehida, poželjno na temperaturi između i uključujući 40 do 95°C, dalje poželjno između i uključujući 60 do 85°C, još više poželjno pri temperaturi od 60 do 70°C, još više poželjno 65 ± 2°C.
8. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što se korak (iii) provodi uporabom NaBH4 kao redukcijskog sredstva.
9. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što dalje uključuje reakciju spoja formule I-a s organskom bazom na temperaturi između 140 i 160°C.
10. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što dalje uključuje odvajanje enantiomera spoja formule I-a dodatkom kiralne O,O'-disupstituirane vinske kiseline, poželjno dibenzoil vinske kiseline.
11. Postupak prema zahtjevu 10, naznačen time što je dibenzoil vinska kiselina O,O’-dibenzoil-L-vinska kiselina.
12. Postupak prema zahtjevu 10, naznačen time da je dibenzoil vinska kiselina mješavina O,O'-dibenzoil-L-vinske kiseline (L-DBTA) i O,O'-dibenzoil-D-vinske kiseline (D-DBTA) sa molarnim omjerom L-DBTA prema D-DBTA od 80:20 ili više.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17210187 | 2017-12-22 | ||
| PCT/EP2018/085437 WO2019121644A1 (en) | 2017-12-22 | 2018-12-18 | Preparation of racemic nicotine by reaction of ethyl nicotinate with n-vinylpyrrolidone in the presence of an alcoholate base and subsequent process steps |
| EP18816110.3A EP3728215B1 (en) | 2017-12-22 | 2018-12-18 | One-pot process for the preparation of racemic nicotine by reaction of ethyl nicotinate with n-vinylpyrrolidone in the presence of sodium ethanolate or potassium ethanolate or mixtures thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20211777T1 true HRP20211777T1 (hr) | 2022-03-04 |
Family
ID=60782090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20211777TT HRP20211777T1 (hr) | 2017-12-22 | 2018-12-18 | Postupak u jednoj posudi za pripremu racemičnog nikotina reakcijom etil nikotinata s n-vinilpirolidonom u prisutnosti natrij etanolata ili kalij etanolata ili njihovih mješavina |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US11407730B2 (hr) |
| EP (1) | EP3728215B1 (hr) |
| JP (1) | JP7085641B2 (hr) |
| KR (1) | KR102575964B1 (hr) |
| CN (1) | CN111511726A (hr) |
| AU (1) | AU2018391652B2 (hr) |
| BR (1) | BR112020012457A2 (hr) |
| CA (1) | CA3085245C (hr) |
| CL (1) | CL2020001657A1 (hr) |
| CY (1) | CY1124741T1 (hr) |
| DK (1) | DK3728215T3 (hr) |
| ES (1) | ES2898315T3 (hr) |
| HR (1) | HRP20211777T1 (hr) |
| HU (1) | HUE057748T2 (hr) |
| IL (1) | IL275584B2 (hr) |
| LT (1) | LT3728215T (hr) |
| PE (1) | PE20211237A1 (hr) |
| PL (1) | PL3728215T3 (hr) |
| PT (1) | PT3728215T (hr) |
| RS (1) | RS62759B1 (hr) |
| RU (1) | RU2753548C1 (hr) |
| SG (1) | SG11202005639UA (hr) |
| SI (1) | SI3728215T1 (hr) |
| WO (1) | WO2019121644A1 (hr) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2753492C1 (ru) | 2017-12-22 | 2021-08-17 | Зигфрид АГ | Хиральное разделение смеси энантиомеров никотина |
| CN110256403B (zh) * | 2019-07-02 | 2020-06-19 | 深圳市馨艺坊生物科技有限公司 | 一种人工合成尼古丁的制备方法 |
| WO2021127986A1 (zh) * | 2019-12-24 | 2021-07-01 | 深圳雾芯科技有限公司 | 一种制备尼古丁的方法 |
| CN112125883A (zh) * | 2020-10-22 | 2020-12-25 | 东莞市鸿馥生物科技有限公司 | 一种消旋烟碱的合成方法 |
| CN114437025B (zh) * | 2020-11-05 | 2023-08-25 | 上海零诺生物科技有限公司 | 消旋6-甲基烟碱及其制备方法、以及应用 |
| CN112795603B (zh) * | 2020-12-14 | 2022-06-24 | 山东金城医药化工有限公司 | 一种制备(s)-2-(3-吡啶)-吡咯烷的方法 |
| CN112409327A (zh) * | 2020-11-18 | 2021-02-26 | 山东金城医药化工有限公司 | 一种高光学纯度烟碱的制备方法 |
| CN113087697A (zh) * | 2021-04-12 | 2021-07-09 | 深圳市优绿信生物科技有限公司 | 一种尼古丁的合成方法 |
| CN114702474B (zh) * | 2021-04-21 | 2023-03-28 | 黄冈中有生物科技有限公司 | 一种左旋烟碱的制备方法 |
| CN114644614B (zh) * | 2021-04-21 | 2023-03-28 | 黄冈中有生物科技有限公司 | 一种左旋烟碱的制备方法 |
| CN115260088A (zh) * | 2021-04-30 | 2022-11-01 | 武汉中有药业有限公司 | 烟碱及其中间体的制备方法 |
| CN113475739B (zh) * | 2021-07-10 | 2022-11-11 | 深圳市真味生物科技有限公司 | 一种s-尼古丁的制备方法 |
| CN113475740B (zh) * | 2021-07-10 | 2022-10-21 | 深圳市真味生物科技有限公司 | 一种手性合成尼古丁的制备方法 |
| CN113416180A (zh) * | 2021-08-09 | 2021-09-21 | 东莞市鸿馥生物科技有限公司 | 一种(s)-1-甲基-2-(3-吡啶基)吡咯烷的拆分方法 |
| CN114195759B (zh) * | 2021-08-26 | 2023-10-20 | 上海零诺生物科技有限公司 | 一种2-甲基-5-（1-甲基吡咯烷-2-基）吡啶制备方法 |
| CN113788815A (zh) * | 2021-09-27 | 2021-12-14 | 成昌梅 | 一种烟碱中间体的合成制备方法 |
| CN113999201B (zh) * | 2021-11-03 | 2023-11-03 | 成昌梅 | 一种烟碱的合成制备方法 |
| WO2023084498A1 (en) | 2021-11-15 | 2023-05-19 | Nicoventures Trading Limited | Oral products with nicotine-polymer complex |
| CN114989135A (zh) * | 2022-01-19 | 2022-09-02 | 广州天然科技有限公司 | 一种2-甲基-5-(1-甲基吡咯烷-2-基)吡啶的有机酸盐及其制备方法 |
| CN114671852A (zh) * | 2022-04-24 | 2022-06-28 | 仙居两山生物科技有限公司 | 一种高纯度左旋烟碱医药中间体的制备方法 |
| CN115093394A (zh) * | 2022-07-20 | 2022-09-23 | 北京世桥生物制药有限公司 | S-(-)-尼古丁(-)-二苯甲酰-l-酒石酸盐晶型、制备方法及应用 |
| EP4332098A1 (en) | 2022-08-31 | 2024-03-06 | Siegfried AG | Chiral synthesis of nornicotine and nicotine |
| WO2024079722A1 (en) | 2022-10-14 | 2024-04-18 | Nicoventures Trading Limited | Capsule-containing pouched products |
| CN115594662A (zh) * | 2022-10-19 | 2023-01-13 | 昆明理工大学（Cn） | 一种(s)-烟碱的制备方法 |
| WO2024095163A1 (en) | 2022-11-01 | 2024-05-10 | Nicoventures Trading Limited | Oral composition comprising encapsulated ph adjusting agent |
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| US7166619B2 (en) | 2002-08-14 | 2007-01-23 | Ppd Discovery , Inc. | Prenylation inhibitors and methods of their synthesis and use |
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| CN102617547B (zh) | 2011-01-27 | 2016-02-10 | 上海特化医药科技有限公司 | 一种制备消旋尼古丁的方法 |
| US8378111B2 (en) * | 2011-02-02 | 2013-02-19 | Divi's Laboratories, Ltd. | Process for the resolution of (R,S)-nicotine |
| US8367837B2 (en) * | 2011-02-14 | 2013-02-05 | Divi's Laboratories, Ltd. | Process for the preparation of (R,S)-nicotine |
| US10943111B2 (en) * | 2014-09-29 | 2021-03-09 | Sony Interactive Entertainment Inc. | Method and apparatus for recognition and matching of objects depicted in images |
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| WO2016061751A1 (en) | 2014-10-22 | 2016-04-28 | Merck Sharp & Dohme Corp. | Ethyl n-boc piperidinyl pyrazolo pyridones as janus kinase inhibitors |
| US9809567B2 (en) | 2014-12-09 | 2017-11-07 | Njoy, Llc | Synthesis and resolution of nicotine |
| KR20180111822A (ko) | 2015-12-30 | 2018-10-11 | 넥스트 제너레이션 랩스, 엘엘씨 | 합성 니코틴을 포함하는 니코틴 대체 요법 물질 |
| WO2017119003A1 (en) | 2016-01-08 | 2017-07-13 | Council Of Scientific & Industrial Research | A process for the preparation of nicotine |
| RU2753492C1 (ru) | 2017-12-22 | 2021-08-17 | Зигфрид АГ | Хиральное разделение смеси энантиомеров никотина |
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2018
- 2018-12-18 DK DK18816110.3T patent/DK3728215T3/da active
- 2018-12-18 HU HUE18816110A patent/HUE057748T2/hu unknown
- 2018-12-18 SI SI201830438T patent/SI3728215T1/sl unknown
- 2018-12-18 AU AU2018391652A patent/AU2018391652B2/en active Active
- 2018-12-18 PT PT188161103T patent/PT3728215T/pt unknown
- 2018-12-18 LT LTEPPCT/EP2018/085437T patent/LT3728215T/lt unknown
- 2018-12-18 HR HRP20211777TT patent/HRP20211777T1/hr unknown
- 2018-12-18 CN CN201880083272.9A patent/CN111511726A/zh active Pending
- 2018-12-18 WO PCT/EP2018/085437 patent/WO2019121644A1/en unknown
- 2018-12-18 PE PE2020000801A patent/PE20211237A1/es unknown
- 2018-12-18 SG SG11202005639UA patent/SG11202005639UA/en unknown
- 2018-12-18 KR KR1020207020579A patent/KR102575964B1/ko active IP Right Grant
- 2018-12-18 RU RU2020120574A patent/RU2753548C1/ru active
- 2018-12-18 US US16/957,006 patent/US11407730B2/en active Active
- 2018-12-18 PL PL18816110T patent/PL3728215T3/pl unknown
- 2018-12-18 BR BR112020012457-5A patent/BR112020012457A2/pt active Search and Examination
- 2018-12-18 CA CA3085245A patent/CA3085245C/en active Active
- 2018-12-18 JP JP2020554569A patent/JP7085641B2/ja active Active
- 2018-12-18 ES ES18816110T patent/ES2898315T3/es active Active
- 2018-12-18 RS RS20211593A patent/RS62759B1/sr unknown
- 2018-12-18 EP EP18816110.3A patent/EP3728215B1/en active Active
-
2020
- 2020-06-18 CL CL2020001657A patent/CL2020001657A1/es unknown
- 2020-06-22 IL IL275584A patent/IL275584B2/en unknown
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2021
- 2021-11-25 CY CY20211101024T patent/CY1124741T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LT3728215T (lt) | 2021-12-10 |
| RS62759B1 (sr) | 2022-01-31 |
| JP2021517901A (ja) | 2021-07-29 |
| DK3728215T3 (da) | 2021-11-08 |
| CA3085245C (en) | 2023-06-13 |
| CY1124741T1 (el) | 2022-07-22 |
| BR112020012457A2 (pt) | 2020-11-24 |
| AU2018391652A1 (en) | 2020-07-02 |
| AU2018391652B2 (en) | 2022-03-10 |
| CA3085245A1 (en) | 2019-06-27 |
| IL275584B1 (en) | 2023-04-01 |
| CN111511726A (zh) | 2020-08-07 |
| PE20211237A1 (es) | 2021-07-09 |
| US20200331884A1 (en) | 2020-10-22 |
| PL3728215T3 (pl) | 2022-05-16 |
| EP3728215A1 (en) | 2020-10-28 |
| IL275584A (en) | 2020-08-31 |
| WO2019121644A1 (en) | 2019-06-27 |
| JP7085641B2 (ja) | 2022-06-16 |
| SG11202005639UA (en) | 2020-07-29 |
| PT3728215T (pt) | 2021-11-22 |
| EP3728215B1 (en) | 2021-10-13 |
| HUE057748T2 (hu) | 2022-06-28 |
| RU2753548C1 (ru) | 2021-08-17 |
| SI3728215T1 (sl) | 2022-01-31 |
| KR102575964B1 (ko) | 2023-09-06 |
| KR20200103033A (ko) | 2020-09-01 |
| IL275584B2 (en) | 2023-08-01 |
| CL2020001657A1 (es) | 2020-11-13 |
| US11407730B2 (en) | 2022-08-09 |
| ES2898315T3 (es) | 2022-03-07 |
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