CA3044137C - Improved synthesis of lysine acetylsalicylate · glycine particles - Google Patents
Improved synthesis of lysine acetylsalicylate · glycine particles Download PDFInfo
- Publication number
- CA3044137C CA3044137C CA3044137A CA3044137A CA3044137C CA 3044137 C CA3044137 C CA 3044137C CA 3044137 A CA3044137 A CA 3044137A CA 3044137 A CA3044137 A CA 3044137A CA 3044137 C CA3044137 C CA 3044137C
- Authority
- CA
- Canada
- Prior art keywords
- glycine
- lysine
- acetylsalicylic acid
- mixture
- less
- 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.)
- Active
Links
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title claims abstract description 166
- 239000002245 particle Substances 0.000 title claims abstract description 91
- 239000004471 Glycine Substances 0.000 title claims abstract description 89
- JJBCTCGUOQYZHK-UHFFFAOYSA-N 2-acetyloxybenzoate;(5-amino-1-carboxypentyl)azanium Chemical compound OC(=O)C(N)CCCC[NH3+].CC(=O)OC1=CC=CC=C1C([O-])=O JJBCTCGUOQYZHK-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 14
- 238000003786 synthesis reaction Methods 0.000 title description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 90
- 239000000243 solution Substances 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 66
- 239000000203 mixture Substances 0.000 claims abstract description 61
- JJBCTCGUOQYZHK-ZSCHJXSPSA-N 2-acetyloxybenzoic acid;(2s)-2,6-diaminohexanoic acid Chemical compound NCCCC[C@H](N)C(O)=O.CC(=O)OC1=CC=CC=C1C(O)=O JJBCTCGUOQYZHK-ZSCHJXSPSA-N 0.000 claims abstract description 40
- 239000000047 product Substances 0.000 claims abstract description 39
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims abstract description 37
- 229960001138 acetylsalicylic acid Drugs 0.000 claims abstract description 34
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000004472 Lysine Substances 0.000 claims abstract description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000003756 stirring Methods 0.000 claims abstract description 16
- 239000013078 crystal Substances 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000007864 aqueous solution Substances 0.000 claims abstract description 14
- 239000002244 precipitate Substances 0.000 claims abstract description 13
- 229910001868 water Inorganic materials 0.000 claims abstract description 12
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 229960003646 lysine Drugs 0.000 claims description 31
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 26
- 238000011534 incubation Methods 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 5
- 230000001954 sterilising effect Effects 0.000 claims description 3
- HZRUTVAFDWTKGD-JEDNCBNOSA-N (2s)-2,6-diaminohexanoic acid;hydrate Chemical compound O.NCCCC[C@H](N)C(O)=O HZRUTVAFDWTKGD-JEDNCBNOSA-N 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 229960002306 lysine monohydrate Drugs 0.000 claims description 2
- 235000018977 lysine Nutrition 0.000 description 23
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 9
- 238000002156 mixing Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- HZRUTVAFDWTKGD-UHFFFAOYSA-N 2,6-diaminohexanoic acid;hydrate Chemical compound O.NCCCCC(N)C(O)=O HZRUTVAFDWTKGD-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 2
- YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 244000126002 Ziziphus vulgaris Species 0.000 description 1
- -1 acetylsalicylic acid lysinate Acetylsalicylic acid lysinate Chemical compound 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-M lysinate Chemical compound NCCCCC(N)C([O-])=O KDXKERNSBIXSRK-UHFFFAOYSA-M 0.000 description 1
- 229960005337 lysine hydrochloride Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/26—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing carboxyl groups by reaction with HCN, or a salt thereof, and amines, or from aminonitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
- C07C227/42—Crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/26—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one amino group bound to the carbon skeleton, e.g. lysine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16206723 | 2016-12-23 | ||
| EP16206723.5 | 2016-12-23 | ||
| PCT/EP2017/084369 WO2018115434A1 (en) | 2016-12-23 | 2017-12-22 | Improved synthesis of lysine acetylsalicylate · glycine particles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA3044137A1 CA3044137A1 (en) | 2018-06-28 |
| CA3044137C true CA3044137C (en) | 2021-06-15 |
Family
ID=57680128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3044137A Active CA3044137C (en) | 2016-12-23 | 2017-12-22 | Improved synthesis of lysine acetylsalicylate · glycine particles |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10882811B2 (enExample) |
| EP (1) | EP3558920B1 (enExample) |
| JP (1) | JP7012725B2 (enExample) |
| CN (1) | CN110114333B (enExample) |
| AU (1) | AU2017383071B2 (enExample) |
| CA (1) | CA3044137C (enExample) |
| DK (1) | DK3558920T3 (enExample) |
| ES (1) | ES2877856T3 (enExample) |
| PT (1) | PT3558920T (enExample) |
| RU (1) | RU2764573C2 (enExample) |
| WO (1) | WO2018115434A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113105326A (zh) * | 2021-03-24 | 2021-07-13 | 海南卓华制药有限公司 | 赖氨匹林的制备方法及应用 |
| AU2023205426A1 (en) | 2022-01-05 | 2024-06-13 | Aspiair Gmbh | Improved synthesis of lysine acetylsalicylate · glycine particles |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2101867A (en) | 1934-08-18 | 1937-12-14 | Clemmy O Miller | Manufacture of water-soluble, storage-stable acetylsalicylic acid products |
| FR1295304A (fr) | 1956-05-07 | 1962-06-08 | Equilibre Biolog L | Nouveau sel de l'acide acétyl-salicylique et son procédé de préparation |
| US3392195A (en) | 1963-09-09 | 1968-07-09 | Galat Alexander | Amino acid derivatives |
| ES385222A1 (es) | 1970-11-05 | 1973-04-01 | Liade Sa Lab | Procedimiento de obtencion de una sal soluble del acido a- cetil salicilico. |
| JPS5610110A (en) | 1979-07-06 | 1981-02-02 | Green Cross Corp:The | Acetyl salicylate salt preparation for injection |
| US4446132A (en) | 1982-03-11 | 1984-05-01 | Dynatech Laboratories Incorporated | Nontoxic aspirin composition |
| FR2611501B1 (fr) | 1987-03-04 | 1991-12-06 | Corbiere Jerome | Nouvelles compositions pharmaceutiques pour la voie buccale a base d'acetylsalielylate de lysine et leur procede d'obtention |
| CN1043138C (zh) * | 1992-05-22 | 1999-04-28 | 安徽省蚌埠安宝药厂 | 赖氨匹林的制造方法 |
| DE10034802A1 (de) * | 2000-07-18 | 2002-01-31 | Bayer Ag | Stabile Salze von O-Acetylsalicylsäure mit basischen Aminosäuren |
| DE10202019A1 (de) * | 2002-01-18 | 2003-07-24 | Bayer Ag | Stabile Salze von o-Acetylsalicylsäure mit basischen Aminosäuren II |
| US20060166901A1 (en) | 2005-01-03 | 2006-07-27 | Yu Ruey J | Compositions comprising O-acetylsalicyl derivatives of aminocarbohydrates and amino acids |
| DE102005025283A1 (de) * | 2005-06-02 | 2006-12-07 | Bayer Healthcare Ag | Stabiler Wirkstoffkomplex von Salzen der o-Acetylsalicylsäure mit basischen Aminosäuren und Glycin |
| DE102005049293A1 (de) | 2005-10-15 | 2007-04-26 | Bayer Healthcare Ag | Kombinationspräparate von Salzen oder o-Acetylsalicylsäure |
| DE102008004386A1 (de) | 2008-01-14 | 2009-07-23 | Activaero Gmbh | Verwendung eines Acetylsalicylsäuresalzes zur Behandlung viraler Infektionen |
| FR2965261B1 (fr) * | 2009-09-30 | 2012-10-26 | Holis Technologies | Procede de preparation d'un sel d'acide o-acetylsalicylique d'un acide amine basique et composition obtenue par ce procede |
| FR2973370B1 (fr) | 2011-03-29 | 2013-05-03 | Holis Technologies | Procede a faible cout pour la preparation d'un acide o-acetylsalicyclique et d'un acide amine basique |
| CN102503845A (zh) * | 2011-09-28 | 2012-06-20 | 广州普星药业有限公司 | 一种dl-赖氨酸阿司匹林盐的制备方法及其应用 |
| ITMI20121144A1 (it) | 2012-06-28 | 2013-12-29 | Dipharma Francis Srl | Procedimento per la preparazione di un sale di un farmaco antinfiammatorio non steroideo |
| FR3021654B1 (fr) | 2014-05-28 | 2016-06-24 | Unither Pharmaceuticals | Procede de preparation d'un sel d'acide acetylsalicylique et d'un acide amine basique |
| DK3393517T3 (da) * | 2015-12-22 | 2021-11-01 | Aspiair Gmbh | Acetylsalicylsyre til anvendelse til behandling af moderat til alvorlig influenza |
-
2017
- 2017-12-22 ES ES17822689T patent/ES2877856T3/es active Active
- 2017-12-22 PT PT178226890T patent/PT3558920T/pt unknown
- 2017-12-22 RU RU2019115337A patent/RU2764573C2/ru active
- 2017-12-22 JP JP2019533172A patent/JP7012725B2/ja active Active
- 2017-12-22 DK DK17822689.0T patent/DK3558920T3/da active
- 2017-12-22 CN CN201780080190.4A patent/CN110114333B/zh active Active
- 2017-12-22 US US16/472,726 patent/US10882811B2/en active Active
- 2017-12-22 AU AU2017383071A patent/AU2017383071B2/en active Active
- 2017-12-22 EP EP17822689.0A patent/EP3558920B1/en active Active
- 2017-12-22 CA CA3044137A patent/CA3044137C/en active Active
- 2017-12-22 WO PCT/EP2017/084369 patent/WO2018115434A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP3558920B1 (en) | 2021-04-07 |
| PT3558920T (pt) | 2021-06-09 |
| CA3044137A1 (en) | 2018-06-28 |
| DK3558920T3 (da) | 2021-07-05 |
| WO2018115434A1 (en) | 2018-06-28 |
| ES2877856T3 (es) | 2021-11-17 |
| RU2019115337A3 (enExample) | 2021-03-12 |
| AU2017383071A1 (en) | 2019-06-06 |
| JP7012725B2 (ja) | 2022-01-28 |
| AU2017383071B2 (en) | 2021-04-29 |
| CN110114333A (zh) | 2019-08-09 |
| CN110114333B (zh) | 2022-12-02 |
| JP2020514261A (ja) | 2020-05-21 |
| RU2019115337A (ru) | 2021-02-01 |
| RU2764573C2 (ru) | 2022-01-18 |
| EP3558920A1 (en) | 2019-10-30 |
| US20190322610A1 (en) | 2019-10-24 |
| US10882811B2 (en) | 2021-01-05 |
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