RU2020122121A - Соли органических сульфокислот со сложными эфирами аминокислот и способ их получения - Google Patents
Соли органических сульфокислот со сложными эфирами аминокислот и способ их получения Download PDFInfo
- Publication number
- RU2020122121A RU2020122121A RU2020122121A RU2020122121A RU2020122121A RU 2020122121 A RU2020122121 A RU 2020122121A RU 2020122121 A RU2020122121 A RU 2020122121A RU 2020122121 A RU2020122121 A RU 2020122121A RU 2020122121 A RU2020122121 A RU 2020122121A
- Authority
- RU
- Russia
- Prior art keywords
- group
- organic sulfonic
- carbon atoms
- sulfonic acid
- lactam
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 11
- 150000001413 amino acids Chemical class 0.000 title claims 5
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- -1 amino acid ester Chemical class 0.000 claims 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 150000003951 lactams Chemical class 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 150000003460 sulfonic acids Chemical class 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 150000002009 diols Chemical class 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical group C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 229920005628 alkoxylated polyol Polymers 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 150000005215 alkyl ethers Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims 1
- 229920005862 polyol Polymers 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000005846 sugar alcohols Polymers 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 125000005425 toluyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 150000003955 ε-lactams Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/65—Mixtures of anionic with cationic compounds
-
- 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
- C07C227/22—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from lactams, cyclic ketones or cyclic oximes, e.g. by reactions involving Beckmann rearrangement
-
- 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
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
-
- 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
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/143—Sulfonic acid esters
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/30—Amines; Substituted amines ; Quaternized amines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/3409—Alkyl -, alkenyl -, cycloalkyl - or terpene sulfates or sulfonates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/3418—Toluene -, xylene -, cumene -, benzene - or naphthalene sulfonates or sulfates
-
- 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
- C07C309/31—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 by alkyl groups containing at least three carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17205357 | 2017-12-05 | ||
| EP17205357.1 | 2017-12-05 | ||
| PCT/EP2018/082663 WO2019110371A1 (en) | 2017-12-05 | 2018-11-27 | Organic sulfonic acid salts of amino acid esters and process for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2020122121A true RU2020122121A (ru) | 2022-01-10 |
Family
ID=60574478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2020122121A RU2020122121A (ru) | 2017-12-05 | 2018-11-27 | Соли органических сульфокислот со сложными эфирами аминокислот и способ их получения |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US11780802B2 (https=) |
| EP (1) | EP3720838B1 (https=) |
| JP (2) | JP7420718B2 (https=) |
| CN (1) | CN111433184B (https=) |
| BR (1) | BR112020009418B1 (https=) |
| ES (1) | ES2924880T3 (https=) |
| MX (1) | MX2020005956A (https=) |
| PL (1) | PL3720838T3 (https=) |
| RU (1) | RU2020122121A (https=) |
| WO (1) | WO2019110371A1 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112020009418B1 (pt) * | 2017-12-05 | 2023-10-10 | Basf Se | Processo para a síntese de sais de ácido sulfônico orgânico de ésteres de aminoácido, e, sal de ácido sulfônico orgânico de um éster de aminoácido |
| ES2928825T3 (es) * | 2018-07-03 | 2022-11-22 | Nouryon Chemicals Int Bv | Esteres de ácidos amino carboxílicos y un proceso para prepararlos |
| EP3845519A1 (en) * | 2019-12-30 | 2021-07-07 | Nouryon Chemicals International B.V. | Esters of amino carboxylic acids and a process to prepare them |
| TWI856233B (zh) * | 2020-01-29 | 2024-09-21 | 美商艾德凡斯化學公司 | 胺基酸界面活性劑 |
| AU2021236069B9 (en) * | 2020-03-11 | 2024-02-01 | Advansix Resins & Chemicals Llc | Surfactants for oil and gas production |
| EP3933017B1 (en) | 2020-07-03 | 2026-04-08 | The Procter & Gamble Company | Fabric and home care product comprising a sulfatized esteramine |
| JP2023532715A (ja) | 2020-07-03 | 2023-07-31 | ビーエーエスエフ ソシエタス・ヨーロピア | 硫酸化エステルアミン |
| BR112023000343A2 (pt) * | 2020-07-09 | 2023-01-31 | Advansix Resins & Chemicals Llc | Tensoativos de aminoácido ramificado |
| AU2021306216B2 (en) * | 2020-07-09 | 2023-12-21 | Advansix Resins & Chemicals Llc | Branched amino acid surfactants |
| CN116075582B (zh) * | 2020-07-13 | 2025-08-19 | 艾德凡斯化学公司 | 用于清洁产品的支链氨基酸表面活性剂 |
| CA3185065A1 (en) * | 2020-07-13 | 2022-01-20 | Edward Asirvatham | Branched amino acid surfactants for agricultural products |
| AU2021307397B2 (en) * | 2020-07-13 | 2024-06-13 | Advansix Resins & Chemicals Llc | Branched amino acid surfactants for use in healthcare products |
| WO2022015604A1 (en) | 2020-07-13 | 2022-01-20 | Advansix Resins & Chemicals Llc | Branched amino acid surfactants for personal care and cosmetic products |
| CA3298099A1 (en) | 2020-07-13 | 2026-03-02 | Advansix Resins & Chemicals Llc | Branched amino acid surfactants for electronics products |
| EP4179038A1 (en) * | 2020-07-13 | 2023-05-17 | AdvanSix Resins & Chemicals LLC | Branched amino acid surfactants for oil and gas production |
| CN116057130B (zh) * | 2020-07-13 | 2024-05-28 | 艾德凡斯化学公司 | 用于油墨、涂料和胶粘剂的支链氨基酸表面活性剂 |
| EP4019615A1 (en) | 2020-12-28 | 2022-06-29 | The Procter & Gamble Company | Liquid hand dishwashing cleaning composition |
| EP4019614A1 (en) * | 2020-12-28 | 2022-06-29 | The Procter & Gamble Company | Cleaning product |
| WO2024042005A1 (en) | 2022-08-22 | 2024-02-29 | Basf Se | Process for producing sulfatized esteramines |
| GB2627342A (en) * | 2022-12-16 | 2024-08-21 | Basf Se | Process for the preparation of amino acids esters and organic sulfonic acids salts thereof and amino acid esters and their salts |
| DE102023135175A1 (de) | 2022-12-16 | 2024-06-27 | Basf Se | Verfahren zur Herstellung von Aminosäureestern und organischen Sulfonsäuresalzen sowie Aminosäureestern und deren Salzen |
| EP4386074B1 (en) | 2022-12-16 | 2025-12-03 | The Procter & Gamble Company | Fabric and home care composition |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL270754A (https=) * | 1960-10-28 | 1900-01-01 | ||
| US3939200A (en) | 1966-01-06 | 1976-02-17 | Rohm And Haas Company | Aliphatic acyl-containing amine hydrochlorides |
| US4176232A (en) * | 1968-06-27 | 1979-11-27 | Rohm And Haas Company | Sulfonic acid salts of acyloxyalkylamines |
| FR2208976B1 (https=) * | 1972-11-30 | 1978-02-24 | Modokemi Ab | |
| US4154956A (en) * | 1973-12-21 | 1979-05-15 | Toray Industries, Inc. | Method for producing lysine ester |
| JPS5339410B2 (https=) * | 1973-12-21 | 1978-10-21 | ||
| US4340730A (en) * | 1980-06-09 | 1982-07-20 | G. D. Searle & Co. | N6 -Substituted adenosines |
| SU1276661A1 (ru) * | 1983-02-17 | 1986-12-15 | Институт фармакологии АМН СССР | Гексадецилсульфаты гексадециловых эфиров аминокислот,обладающие нейротропной и ноотропной активностью |
| US4550137A (en) * | 1983-03-28 | 1985-10-29 | Ppg Industries, Inc. | Lactam derived salts of sulfonic acids as latent acid catalysts |
| JP3792295B2 (ja) * | 1996-05-09 | 2006-07-05 | 花王株式会社 | 新規なアミノ酸エステル塩及びその製造法並びにそれを含有する柔軟剤組成物 |
| KR101580067B1 (ko) * | 2007-01-12 | 2015-12-23 | 노파르티스 아게 | 5-바이페닐-4-아미노-2-메틸 펜탄산의 제조 방법 |
| FR2977585B1 (fr) | 2011-07-06 | 2015-08-28 | Ard Sa | Procede de preparation d'esters |
| TWI591045B (zh) | 2012-08-03 | 2017-07-11 | 祥翊製藥股份有限公司 | 作為有效藥劑成分之６－胺基己酸的製造方法 |
| ES2895710T3 (es) | 2014-05-09 | 2022-02-22 | Inolex Investment Corp | Emulsionantes catiónicos de origen no petroquímico y composiciones y métodos relacionados |
| MX380337B (es) | 2014-09-08 | 2025-03-11 | Mexicano Inst Petrol | Proceso mejorado para la obtencion de esteres de amioacidos ionicos. |
| AU2016236239B2 (en) * | 2015-03-24 | 2020-06-25 | H. Lundbeck A/S | Manufacture of 4,5,6,7-tetrahydroisozaxolo[5,4-c]pyridin-3-ol |
| BR112020009418B1 (pt) * | 2017-12-05 | 2023-10-10 | Basf Se | Processo para a síntese de sais de ácido sulfônico orgânico de ésteres de aminoácido, e, sal de ácido sulfônico orgânico de um éster de aminoácido |
-
2018
- 2018-11-27 BR BR112020009418-8A patent/BR112020009418B1/pt active IP Right Grant
- 2018-11-27 MX MX2020005956A patent/MX2020005956A/es unknown
- 2018-11-27 PL PL18804653.6T patent/PL3720838T3/pl unknown
- 2018-11-27 WO PCT/EP2018/082663 patent/WO2019110371A1/en not_active Ceased
- 2018-11-27 ES ES18804653T patent/ES2924880T3/es active Active
- 2018-11-27 EP EP18804653.6A patent/EP3720838B1/en active Active
- 2018-11-27 CN CN201880078186.9A patent/CN111433184B/zh active Active
- 2018-11-27 RU RU2020122121A patent/RU2020122121A/ru unknown
- 2018-11-27 JP JP2020531125A patent/JP7420718B2/ja active Active
- 2018-11-27 US US16/770,080 patent/US11780802B2/en active Active
-
2023
- 2023-10-02 JP JP2023171226A patent/JP2024001105A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP7420718B2 (ja) | 2024-01-23 |
| JP2021505614A (ja) | 2021-02-18 |
| CN111433184B (zh) | 2025-06-06 |
| ES2924880T3 (es) | 2022-10-11 |
| MX2020005956A (es) | 2020-08-24 |
| EP3720838A1 (en) | 2020-10-14 |
| CN111433184A (zh) | 2020-07-17 |
| WO2019110371A1 (en) | 2019-06-13 |
| BR112020009418B1 (pt) | 2023-10-10 |
| BR112020009418A2 (pt) | 2020-10-13 |
| JP2024001105A (ja) | 2024-01-09 |
| US20210188764A1 (en) | 2021-06-24 |
| PL3720838T3 (pl) | 2022-12-19 |
| US11780802B2 (en) | 2023-10-10 |
| EP3720838B1 (en) | 2022-08-03 |
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