PE20211992A1 - Proceso para preparar un agonista dual de gip/glp1 - Google Patents
Proceso para preparar un agonista dual de gip/glp1Info
- Publication number
- PE20211992A1 PE20211992A1 PE2021001218A PE2021001218A PE20211992A1 PE 20211992 A1 PE20211992 A1 PE 20211992A1 PE 2021001218 A PE2021001218 A PE 2021001218A PE 2021001218 A PE2021001218 A PE 2021001218A PE 20211992 A1 PE20211992 A1 PE 20211992A1
- Authority
- PE
- Peru
- Prior art keywords
- seq
- disclosed
- peptide
- tirzepatide
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- 102100025101 GATA-type zinc finger protein 1 Human genes 0.000 title abstract 2
- 108091016366 Histone-lysine N-methyltransferase EHMT1 Proteins 0.000 title abstract 2
- 229940125542 dual agonist Drugs 0.000 title abstract 2
- 239000000543 intermediate Substances 0.000 abstract 4
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 4
- 108091004331 tirzepatide Proteins 0.000 abstract 3
- BTSOGEDATSQOAF-SMAAHMJQSA-N tirzepatide Chemical compound CC[C@H](C)[C@@H](C(N[C@@H](C)C(N[C@@H](CCC(N)=O)C(N[C@@H](CCCCNC(COCCOCCNC(COCCOCCNC(CC[C@H](C(O)=O)NC(CCCCCCCCCCCCCCCCCCC(O)=O)=O)=O)=O)=O)C(N[C@@H](C)C(N[C@@H](CC1=CC=CC=C1)C(N[C@@H](C(C)C)C(N[C@@H](CCC(N)=O)C(N[C@@H](CC1=CNC2=C1C=CC=C2)C(N[C@@H](CC(C)C)C(N[C@@H]([C@@H](C)CC)C(N[C@@H](C)C(NCC(NCC(N(CCC1)[C@@H]1C(N[C@@H](CO)C(N[C@@H](CO)C(NCC(N[C@@H](C)C(N(CCC1)[C@@H]1C(N(CCC1)[C@@H]1C(N(CCC1)[C@@H]1C(N[C@@H](CO)C(N)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)NC([C@H](CCCCN)NC([C@H](CC(O)=O)NC([C@H](CC(C)C)NC(C(C)(C)NC([C@H]([C@@H](C)CC)NC([C@H](CO)NC([C@H](CC(C=C1)=CC=C1O)NC([C@H](CC(O)=O)NC([C@H](CO)NC([C@H]([C@@H](C)O)NC([C@H](CC1=CC=CC=C1)NC([C@H]([C@@H](C)O)NC(CNC([C@H](CCC(O)=O)NC(C(C)(C)NC([C@H](CC(C=C1)=CC=C1O)N)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O BTSOGEDATSQOAF-SMAAHMJQSA-N 0.000 abstract 3
- 229940121512 tirzepatide Drugs 0.000 abstract 3
- 239000004472 Lysine Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- MGXWVYUBJRZYPE-YUGYIWNOSA-N incretin Chemical class C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)[C@@H](C)O)[C@@H](C)CC)C1=CC=C(O)C=C1 MGXWVYUBJRZYPE-YUGYIWNOSA-N 0.000 abstract 2
- 239000000859 incretin Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 abstract 1
- CCTFAOUOYLVUFG-UHFFFAOYSA-N 2-(1-amino-1-imino-2-methylpropan-2-yl)azo-2-methylpropanimidamide Chemical compound NC(=N)C(C)(C)N=NC(C)(C)C(N)=N CCTFAOUOYLVUFG-UHFFFAOYSA-N 0.000 abstract 1
- 108010002156 Depsipeptides Proteins 0.000 abstract 1
- 108010004460 Gastric Inhibitory Polypeptide Proteins 0.000 abstract 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 abstract 1
- LBSPZZSGTIBOFG-UHFFFAOYSA-N bis[2-(4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene;dihydrochloride Chemical compound Cl.Cl.N=1CCNC=1C(C)(C)N=NC(C)(C)C1=NCCN1 LBSPZZSGTIBOFG-UHFFFAOYSA-N 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 238000006477 desulfuration reaction Methods 0.000 abstract 1
- 230000023556 desulfurization Effects 0.000 abstract 1
- 230000003009 desulfurizing effect Effects 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- -1 lysine amino acid Chemical class 0.000 abstract 1
- 238000001728 nano-filtration Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 abstract 1
- 239000002699 waste material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/06—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by azeotropic distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/645—Secretins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
- C07K1/113—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/605—Glucagons
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Endocrinology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- Water Supply & Treatment (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La presente invencion se refiere a los procesos y productos intermedios para preparar un peptido agonista dual de GIP/GLP1, tal como la tirzepatida (SEQ ID NO 1) o una sal aceptable de esta. Los compuestos intermedios son tal como se revelan en las SEQ ID NO 17, SEQ ID NO 11, SEQ ID NO 22, SEQ ID NO 21, SEQ ID NO 20, SEQ ID NO 2, SEQ ID NO 4, entre otros. El proceso de preparacion comprende: i) nanofiltracion de un producto intermedio de tirzepatida; ii) desproteccion de un compuesto tal como se revela en la SEC ID NO 22 o una sal farmaceuticamente aceptable de este; iii) acilar selectivamente un aminoacido lisina en un peptido que comprende el acoplamiento de un peptido-lisina-NH2 unido a la resina, tal como el revelado en la SEQ ID NO 24, con t-butil-eicosanodioil-Glu-(O-terc-butil)-(acido-8-amino-3,6-dioxaoctanoico)-(acido-8-amino-3,6-dioxaoctanoico)-OH; iv) conversion de un isomero del depsipeptido, tal como lo revelado en la SEQ ID NO 40, en el peptido deseado, tal como la incretina de SEQ ID NO: 35; v) desulfurar la incretina mediante la reaccion con un iniciador de radicales, tal como diclorhidrato de 2,2'-azobis[2-(2-imidazolin-2-il)propano] y diclorhidrato de 2,2'-azobis(2-metilpropionamidina), donde el proceso de desulfuracion proporciona un peptido de SEQ ID NO 1. Dicho proceso es eficiente y ecologico, que incluye productos intermedios estables para proporcionar la tirzepatida con menos etapas de purificacion, y produce corrientes de desechos minimo para la seguridad mejorada tanto para el medio ambiente como para el operador.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962797963P | 2019-01-29 | 2019-01-29 | |
| US201962815053P | 2019-03-07 | 2019-03-07 | |
| US201962818342P | 2019-03-14 | 2019-03-14 | |
| PCT/US2020/015353 WO2020159949A1 (en) | 2019-01-29 | 2020-01-28 | Process for preparing a gip/glp1 dual agonist |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20211992A1 true PE20211992A1 (es) | 2021-10-18 |
Family
ID=69724140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2021001218A PE20211992A1 (es) | 2019-01-29 | 2020-01-28 | Proceso para preparar un agonista dual de gip/glp1 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20220135639A1 (es) |
| EP (1) | EP3917950A1 (es) |
| JP (2) | JP7315683B2 (es) |
| KR (1) | KR20210110349A (es) |
| CN (1) | CN113330024A (es) |
| AU (3) | AU2020216922A1 (es) |
| BR (1) | BR112021012368A2 (es) |
| CA (2) | CA3224820A1 (es) |
| CL (1) | CL2021001905A1 (es) |
| CO (1) | CO2021009662A2 (es) |
| EC (1) | ECSP21056124A (es) |
| IL (1) | IL284446A (es) |
| MA (1) | MA54862A (es) |
| MX (1) | MX2021008965A (es) |
| PE (1) | PE20211992A1 (es) |
| SG (1) | SG11202107123TA (es) |
| TW (1) | TWI799680B (es) |
| WO (1) | WO2020159949A1 (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110642935A (zh) * | 2019-09-25 | 2020-01-03 | 成都奥达生物科技有限公司 | 一种替瑞帕肽类似物 |
| CA3200881A1 (en) * | 2020-12-02 | 2022-06-09 | Zhixiang PAN | Lactam-modified polypeptide compounds |
| WO2022159395A1 (en) * | 2021-01-20 | 2022-07-28 | Viking Therapeutics, Inc. | Compositions and methods for the treatment of metabolic and liver disorders |
| CN117866050A (zh) * | 2021-05-28 | 2024-04-12 | 广东众生睿创生物科技有限公司 | 多肽的制备及其应用 |
| WO2023089594A1 (en) | 2021-11-22 | 2023-05-25 | Sun Pharmaceutical Industries Limited | Process for the preparation of tirzepatide or pharmaceutically acceptable salt thereof |
| TW202404996A (zh) | 2022-04-04 | 2024-02-01 | 美商美國禮來大藥廠 | 製備glp-1/升糖素雙重促效劑之方法 |
| CN116023444B (zh) * | 2022-08-12 | 2023-08-01 | 重庆宸安生物制药有限公司 | 一种gip和glp-1双受体激动剂多肽化合物及其应用 |
| WO2024077149A2 (en) * | 2022-10-05 | 2024-04-11 | Eli Lilly And Company | Peptides for incretin synthesis |
| WO2024112617A2 (en) | 2022-11-21 | 2024-05-30 | Eli Lilly And Company | Process for preparing a gip/glp1 dual agonist |
| WO2024134676A1 (en) * | 2022-12-19 | 2024-06-27 | Dr. Reddy’S Laboratories Limited | Process for the preparation of tirzepatide |
| KR20240102887A (ko) * | 2022-12-23 | 2024-07-03 | 한미약품 주식회사 | 신규한 glp-1, gip, 및 글루카곤 수용체 모두에 활성을 갖는 삼중 활성체 및 이를 포함하는 비만의 예방 또는 치료용 약학적 조성물 |
| CN116731154A (zh) * | 2023-08-14 | 2023-09-12 | 苏州金顶生物有限公司 | 一种全液相法制备替西帕肽的方法 |
| CN117736273B (zh) * | 2023-12-08 | 2024-05-07 | 广东省卓肽医药有限公司 | 一种替尔泊肽的纯化方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1076066A1 (en) * | 1999-07-12 | 2001-02-14 | Zealand Pharmaceuticals A/S | Peptides for lowering blood glucose levels |
| CN102414220A (zh) * | 2009-05-01 | 2012-04-11 | 霍夫曼-拉罗奇有限公司 | 使用固相和液相组合技术的促胰岛素肽合成 |
| JOP20200119A1 (ar) | 2015-01-09 | 2017-06-16 | Lilly Co Eli | مركبات مساعد مشترك من gip وglp-1 |
| CN106928086B (zh) * | 2015-12-31 | 2019-05-31 | 深圳翰宇药业股份有限公司 | 一种长链化合物的制备方法 |
-
2020
- 2020-01-22 TW TW109102657A patent/TWI799680B/zh active
- 2020-01-28 CA CA3224820A patent/CA3224820A1/en active Pending
- 2020-01-28 EP EP20707971.6A patent/EP3917950A1/en active Pending
- 2020-01-28 AU AU2020216922A patent/AU2020216922A1/en not_active Abandoned
- 2020-01-28 KR KR1020217024133A patent/KR20210110349A/ko not_active Application Discontinuation
- 2020-01-28 US US17/310,247 patent/US20220135639A1/en active Pending
- 2020-01-28 CA CA3128023A patent/CA3128023A1/en active Pending
- 2020-01-28 CN CN202080011536.7A patent/CN113330024A/zh active Pending
- 2020-01-28 BR BR112021012368-7A patent/BR112021012368A2/pt unknown
- 2020-01-28 PE PE2021001218A patent/PE20211992A1/es unknown
- 2020-01-28 MX MX2021008965A patent/MX2021008965A/es unknown
- 2020-01-28 JP JP2021542153A patent/JP7315683B2/ja active Active
- 2020-01-28 MA MA054862A patent/MA54862A/fr unknown
- 2020-01-28 WO PCT/US2020/015353 patent/WO2020159949A1/en unknown
- 2020-01-28 SG SG11202107123TA patent/SG11202107123TA/en unknown
-
2021
- 2021-06-28 IL IL284446A patent/IL284446A/en unknown
- 2021-07-19 CL CL2021001905A patent/CL2021001905A1/es unknown
- 2021-07-23 CO CONC2021/0009662A patent/CO2021009662A2/es unknown
- 2021-07-29 EC ECSENADI202156124A patent/ECSP21056124A/es unknown
-
2023
- 2023-02-16 JP JP2023022752A patent/JP2023078130A/ja active Pending
- 2023-05-15 AU AU2023203001A patent/AU2023203001B2/en active Active
-
2024
- 2024-02-16 AU AU2024201004A patent/AU2024201004A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU2020216922A1 (en) | 2021-07-15 |
| TWI799680B (zh) | 2023-04-21 |
| CN113330024A (zh) | 2021-08-31 |
| CA3224820A1 (en) | 2020-08-06 |
| BR112021012368A2 (pt) | 2021-09-14 |
| MX2021008965A (es) | 2021-08-24 |
| AU2024201004A1 (en) | 2024-03-07 |
| MA54862A (fr) | 2022-05-04 |
| IL284446A (en) | 2021-08-31 |
| US20220135639A1 (en) | 2022-05-05 |
| JP2023078130A (ja) | 2023-06-06 |
| KR20210110349A (ko) | 2021-09-07 |
| WO2020159949A1 (en) | 2020-08-06 |
| JP7315683B2 (ja) | 2023-07-26 |
| ECSP21056124A (es) | 2021-08-31 |
| CL2021001905A1 (es) | 2022-03-11 |
| AU2023203001A1 (en) | 2023-06-08 |
| CA3128023A1 (en) | 2020-08-06 |
| EP3917950A1 (en) | 2021-12-08 |
| AU2023203001B2 (en) | 2024-03-28 |
| JP2022517834A (ja) | 2022-03-10 |
| CO2021009662A2 (es) | 2021-08-09 |
| TW202043260A (zh) | 2020-12-01 |
| SG11202107123TA (en) | 2021-08-30 |
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