AR122579A1 - Proceso para preparar un agonista dual glp-1 / glucagón - Google Patents
Proceso para preparar un agonista dual glp-1 / glucagónInfo
- Publication number
- AR122579A1 AR122579A1 ARP210101573A ARP210101573A AR122579A1 AR 122579 A1 AR122579 A1 AR 122579A1 AR P210101573 A ARP210101573 A AR P210101573A AR P210101573 A ARP210101573 A AR P210101573A AR 122579 A1 AR122579 A1 AR 122579A1
- Authority
- AR
- Argentina
- Prior art keywords
- compound
- seq
- lys
- side chain
- following formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 title abstract 2
- 102000051325 Glucagon Human genes 0.000 title abstract 2
- 108060003199 Glucagon Proteins 0.000 title abstract 2
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](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=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 title abstract 2
- 102100040918 Pro-glucagon Human genes 0.000 title abstract 2
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(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](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)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(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 title abstract 2
- 229960004666 glucagon Drugs 0.000 title abstract 2
- 229940125542 dual agonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 8
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 abstract 4
- 125000006239 protecting group Chemical group 0.000 abstract 3
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 abstract 1
- 208000008589 Obesity Diseases 0.000 abstract 1
- -1 [2-(2-aminoethoxy)-ethoxy]-acetyl Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000021615 conjugation Effects 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
- 235000020824 obesity Nutrition 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 238000010532 solid phase synthesis reaction Methods 0.000 abstract 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic
-
- 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
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
-
- 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
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Endocrinology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La presente invención proporciona procesos y compuestos para la preparación de compuestos coagonistas de glucagón y GLP-1 que son útiles en el tratamiento de diabetes tipo 2, obesidad, enfermedad del hígado graso no alcohólico (NAFLD) y/o esteatohepatitis no alcohólica (NASH). Reivindicación 1: Un proceso para la preparación de un compuesto de la siguiente fórmula: H₂N-H-Aib-Q-G-T-F-T-S-D-Y-S-K-Y-L-D-E-K-K-A-K-E-F-V-E-W-L-L-E-G-G-PS-S-G-NH₂ en donde la Lys en la posición 20 se modifica químicamente por conjugación del grupo amino épsilon de la cadena lateral de la Lys con ([2-(2-aminoetoxi)-etoxi]-acetil)₂-(g-Glu)-CO-(CH₂)₁₈CO₂H (SEQ ID Nº 1), dicho proceso comprende las etapas de: (i) síntesis en fase sólida de un compuesto de la siguiente fórmula (1) en donde PG¹ es un grupo protector de cadena lateral estable frente a base, en donde Thr en la posición 5 está opcionalmente protegido por PG¹, y en donde PG² es un grupo protector de cadena lateral ivDde, Dde o Alloc (SEQ ID Nº 2); (ii) acilar selectivamente el compuesto en la Lys en la posición 20 (SEQ ID Nº 7) mediante la desprotección selectiva de dicha Lys y el acoplamiento de la Lys-NH₂ resultante (SEQ ID Nº 5) con ᵗBuO-C₂₀-gGlu(ᵗBu)-AEEA-AEEA-OH; y (iii) escindir el compuesto acilado del soporte sólido y eliminar los grupos protectores de la cadena lateral restantes; y (iv) purificar el compuesto. Reivindicación 28: Un compuesto que tiene la siguiente fórmula (2) (SEQ ID Nº 3).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202063038363P | 2020-06-12 | 2020-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR122579A1 true AR122579A1 (es) | 2022-09-21 |
Family
ID=76731121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP210101573A AR122579A1 (es) | 2020-06-12 | 2021-06-09 | Proceso para preparar un agonista dual glp-1 / glucagón |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20230220000A1 (es) |
| EP (1) | EP4165058A1 (es) |
| JP (2) | JP2023529200A (es) |
| KR (1) | KR20230021740A (es) |
| CN (1) | CN115943151A (es) |
| AR (1) | AR122579A1 (es) |
| AU (1) | AU2021286660B2 (es) |
| BR (1) | BR112022023722A2 (es) |
| CA (1) | CA3182429A1 (es) |
| CL (1) | CL2022003459A1 (es) |
| CO (1) | CO2022017726A2 (es) |
| EC (1) | ECSP22094067A (es) |
| IL (1) | IL298265A (es) |
| MX (1) | MX2022015577A (es) |
| PE (1) | PE20230776A1 (es) |
| PH (1) | PH12022553393A1 (es) |
| TW (1) | TWI810586B (es) |
| UA (1) | UA128300C2 (es) |
| WO (1) | WO2021252829A1 (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| IL318334A (en) * | 2022-07-20 | 2025-03-01 | Viking Therapeutics Inc | Pharmaceutical formulations and methods for treating metabolic and liver disorders |
| KR20250096895A (ko) | 2022-10-05 | 2025-06-27 | 일라이 릴리 앤드 캄파니 | 인크레틴 합성을 위한 펩티드 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080318837A1 (en) * | 2003-12-26 | 2008-12-25 | Nastech Pharmaceutical Company Inc. | Pharmaceutical Formation For Increased Epithelial Permeability of Glucose-Regulating Peptide |
| CA2569662A1 (en) * | 2004-06-10 | 2005-12-22 | Enkam Pharmaceuticals A/S | Heparin binding peptide |
| TWI362392B (en) * | 2005-03-18 | 2012-04-21 | Novo Nordisk As | Acylated glp-1 compounds |
| EP1987052B1 (en) * | 2006-02-08 | 2011-04-27 | Lonza AG | Synthesis of glucagon-like peptides |
| CA2759468A1 (en) * | 2009-05-01 | 2010-11-04 | F. Hoffmann-La Roche Ag | Insulinotropic peptide synthesis using solid and solution phase combination techniques |
| MX2015016564A (es) * | 2013-06-20 | 2016-04-15 | Novo Nordisk As | Derivados de peptido similar al glucaton tipo 1 (glp-1) y uso de los mismos. |
| CA2929459C (en) * | 2013-11-06 | 2022-05-03 | Zealand Pharma A/S | Gip-glp-1 dual agonist compounds and methods |
| JP6018129B2 (ja) * | 2014-07-04 | 2016-11-02 | ジーランド ファーマ アクティーゼルスカブ | グルカゴン類似体 |
| CN106519015B (zh) * | 2014-09-23 | 2020-04-17 | 深圳市图微安创科技开发有限公司 | 胃泌酸调节素类似物 |
| AR104932A1 (es) * | 2015-06-22 | 2017-08-23 | Lilly Co Eli | Compuestos co-agonistas del glucagón y péptido-1 similar al glugacón (glp-1) |
| AR105284A1 (es) * | 2015-07-10 | 2017-09-20 | Sanofi Sa | Derivados de exendina-4 como agonistas peptídicos duales específicos de los receptores de glp-1 / glucagón |
| CN106928343A (zh) * | 2015-12-30 | 2017-07-07 | 深圳翰宇药业股份有限公司 | 索玛鲁肽的制备方法 |
| EP3517543B1 (en) * | 2018-01-30 | 2020-11-04 | Bachem AG | Manufacture of glucagon peptides |
| CN109456401B (zh) * | 2018-12-03 | 2019-06-25 | 成都诺和晟泰生物科技有限公司 | 一种索马鲁肽的合成方法 |
| KR20210102362A (ko) * | 2018-12-08 | 2021-08-19 | 엔진 바이오사이언스 리미티드 | 플레카나타이드의 개선된 제조 방법 |
| CN109369798B (zh) * | 2018-12-25 | 2020-09-15 | 苏州天马医药集团天吉生物制药有限公司 | 一种合成索玛鲁肽的方法 |
| CN111217901A (zh) * | 2019-10-31 | 2020-06-02 | 成都圣诺生物制药有限公司 | 一种索马鲁肽的制备方法 |
-
2021
- 2021-06-09 AR ARP210101573A patent/AR122579A1/es unknown
- 2021-06-10 TW TW110121175A patent/TWI810586B/zh active
- 2021-06-11 PE PE2022002871A patent/PE20230776A1/es unknown
- 2021-06-11 UA UAA202204666A patent/UA128300C2/uk unknown
- 2021-06-11 EP EP21736918.0A patent/EP4165058A1/en active Pending
- 2021-06-11 AU AU2021286660A patent/AU2021286660B2/en active Active
- 2021-06-11 JP JP2022575911A patent/JP2023529200A/ja active Pending
- 2021-06-11 PH PH1/2022/553393A patent/PH12022553393A1/en unknown
- 2021-06-11 CN CN202180041909.XA patent/CN115943151A/zh active Pending
- 2021-06-11 WO PCT/US2021/036914 patent/WO2021252829A1/en not_active Ceased
- 2021-06-11 US US18/000,853 patent/US20230220000A1/en active Pending
- 2021-06-11 KR KR1020237000871A patent/KR20230021740A/ko active Pending
- 2021-06-11 CA CA3182429A patent/CA3182429A1/en active Pending
- 2021-06-11 BR BR112022023722A patent/BR112022023722A2/pt unknown
- 2021-06-11 IL IL298265A patent/IL298265A/en unknown
- 2021-06-11 MX MX2022015577A patent/MX2022015577A/es unknown
-
2022
- 2022-12-06 CL CL2022003459A patent/CL2022003459A1/es unknown
- 2022-12-07 CO CONC2022/0017726A patent/CO2022017726A2/es unknown
- 2022-12-12 EC ECSENADI202294067A patent/ECSP22094067A/es unknown
-
2025
- 2025-08-05 JP JP2025130749A patent/JP2025169298A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU2021286660A1 (en) | 2022-12-22 |
| US20230220000A1 (en) | 2023-07-13 |
| JP2025169298A (ja) | 2025-11-12 |
| JP2023529200A (ja) | 2023-07-07 |
| AU2021286660B2 (en) | 2025-03-13 |
| CL2022003459A1 (es) | 2023-06-16 |
| CA3182429A1 (en) | 2021-12-16 |
| TWI810586B (zh) | 2023-08-01 |
| ECSP22094067A (es) | 2023-01-31 |
| UA128300C2 (uk) | 2024-05-29 |
| EP4165058A1 (en) | 2023-04-19 |
| KR20230021740A (ko) | 2023-02-14 |
| TW202214678A (zh) | 2022-04-16 |
| PE20230776A1 (es) | 2023-05-09 |
| BR112022023722A2 (pt) | 2022-12-20 |
| CN115943151A (zh) | 2023-04-07 |
| WO2021252829A1 (en) | 2021-12-16 |
| PH12022553393A1 (en) | 2024-03-25 |
| IL298265A (en) | 2023-01-01 |
| MX2022015577A (es) | 2023-01-30 |
| CO2022017726A2 (es) | 2022-12-20 |
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