HRP20200527T1 - Postupak za pripravu amg 416 - Google Patents
Postupak za pripravu amg 416 Download PDFInfo
- Publication number
- HRP20200527T1 HRP20200527T1 HRP20200527TT HRP20200527T HRP20200527T1 HR P20200527 T1 HRP20200527 T1 HR P20200527T1 HR P20200527T T HRP20200527T T HR P20200527TT HR P20200527 T HRP20200527 T HR P20200527T HR P20200527 T1 HRP20200527 T1 HR P20200527T1
- Authority
- HR
- Croatia
- Prior art keywords
- arg
- cys
- amg
- peptide
- ala
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 11
- ANIAZGVDEUQPRI-ZJQCGQFWSA-N etelcalcetide Chemical compound NC(N)=NCCC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCCN=C(N)N)NC(=O)[C@@H](CCCN=C(N)N)NC(=O)[C@@H](CCCN=C(N)N)NC(=O)[C@@H](C)NC(=O)[C@@H](CSSC[C@H](N)C(O)=O)NC(C)=O ANIAZGVDEUQPRI-ZJQCGQFWSA-N 0.000 title claims 5
- 229950006502 etelcalcetide Drugs 0.000 title claims 5
- 108091022127 etelcalcetide hydrochloride Proteins 0.000 title claims 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims 5
- 239000000047 product Substances 0.000 claims 5
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- 239000002244 precipitate Substances 0.000 claims 3
- 238000004128 high performance liquid chromatography Methods 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 238000004108 freeze drying Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- 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
- 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
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
-
- 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
- C07K1/1072—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 by covalent attachment of residues or functional groups
- C07K1/1075—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 by covalent attachment of residues or functional groups by covalent attachment of amino acids or peptide residues
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/18—Drugs for disorders of the endocrine system of the parathyroid hormones
- A61P5/20—Drugs for disorders of the endocrine system of the parathyroid hormones for decreasing, blocking or antagonising the activity of PTH
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Glass Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (8)
1. Postupak za pripravu AMG 416 kako je navedeno u formuli (I):
[image]
navedeni postupak uključuje:
dovođenje u kontakt peptida sa strukturom Ac-D-Cys(SPy)-D-Ala-D-Arg-D-Arg-D-Arg-D-Ala-D-Arg-NH2 (SEQ ID NO:4) s L-Cys radi dobivanja konjugiranog proizvoda formule (I).
2. Postupak prema patentnom zahtjevu 1, naznačen time što navedeno dovođenje u kontakt uključuje otapanje peptida u vodenoj otopini koja sadrži L-Cys i trifluorooctenu kiselinu (TFA).
3. Postupak prema patentnom zahtjevu 1, naznačen time što nadalje sadrži liofilizaciju konjugiranog proizvoda.
4. Postupak prema patentnom zahtjevu 1, naznačen time što nadalje sadrži dovođenje u kontakt konjugiranog proizvoda s vodenom otopinom koja sadrži izopropil alkohol (IPA) i HCl, stvarajući talog koji sadrži AMG 416 HCL iz SEQ ID NO: 1.
5. Postupak prema patentnom zahtjevu 4, naznačen time što nadalje sadrži pročišćavanje taloga putem HPLC.
6. Postupak za pripravu AMG 416 kako je navedeno u formuli (I):
[image]
navedeni postupak uključuje:
pročišćavanje pomoću HPLC peptida koji ima strukturu Ac-D-Cys(SPy)-D-Ala-D-Arg-D-Arg-D-Arg-D-Ala-D-Arg-NH2 (SEQ ID NO:4) u otopini trifluoroctene kiseline (TFA);
provođenje izmjene otapala azeotropnom destilacijom na pročišćenom peptidu; i
dovođenje u kontakt pročišćenog peptida s L-Cys radi dobivanja konjugiranog proizvoda formule (I).
7. Postupak prema patentnom zahtjevu 6, naznačen time što je L-Cys u otopini vode i IPA.
8. Postupak prema patentnom zahtjevu 7, naznačen time što nadalje sadrži dovođenje u kontakt konjugiranog proizvoda s vodenom otopinom koja sadrži IPA i HCl, stvarajući talog koji sadrži AMG 416 HCL iz SEQ ID NO: 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461974899P | 2014-04-03 | 2014-04-03 | |
| PCT/US2015/024347 WO2015154031A1 (en) | 2014-04-03 | 2015-04-03 | Method for preparing amg 416 |
| EP15773570.5A EP3126373B1 (en) | 2014-04-03 | 2015-04-03 | Method for preparing amg 416 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20200527T1 true HRP20200527T1 (hr) | 2020-06-26 |
Family
ID=54241346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20200527TT HRP20200527T1 (hr) | 2014-04-03 | 2020-04-01 | Postupak za pripravu amg 416 |
Country Status (27)
| Country | Link |
|---|---|
| US (3) | US10407464B2 (hr) |
| EP (3) | EP3708576B1 (hr) |
| JP (1) | JP6710158B2 (hr) |
| KR (1) | KR102397271B1 (hr) |
| CN (1) | CN106795201A (hr) |
| AU (1) | AU2015240527B2 (hr) |
| BR (1) | BR112016022868A2 (hr) |
| CA (1) | CA2944194C (hr) |
| CL (1) | CL2016002513A1 (hr) |
| CY (1) | CY1123100T1 (hr) |
| DK (1) | DK3126373T3 (hr) |
| EA (1) | EA032597B1 (hr) |
| ES (2) | ES2943671T3 (hr) |
| HR (1) | HRP20200527T1 (hr) |
| HU (1) | HUE048489T2 (hr) |
| IL (1) | IL248059B2 (hr) |
| LT (1) | LT3126373T (hr) |
| MA (2) | MA52906A (hr) |
| ME (1) | ME03781B (hr) |
| MX (1) | MX2016012965A (hr) |
| PL (1) | PL3126373T3 (hr) |
| PT (1) | PT3126373T (hr) |
| RS (1) | RS60187B1 (hr) |
| SG (1) | SG11201608176VA (hr) |
| SI (1) | SI3126373T1 (hr) |
| WO (1) | WO2015154031A1 (hr) |
| ZA (1) | ZA201606844B (hr) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CR20160002A (es) | 2013-06-28 | 2018-02-13 | Amgen Inc | Formulación estable líquida de etelcalcetide (amg 461) |
| MX2016012965A (es) | 2014-04-03 | 2017-07-06 | Amgen Inc | Metodo para preparar amg 416. |
| CN106928320B (zh) * | 2015-12-31 | 2021-01-15 | 深圳翰宇药业股份有限公司 | 一种合成Etelcalcetide的方法 |
| CN106928321B (zh) * | 2015-12-31 | 2019-07-26 | 深圳翰宇药业股份有限公司 | 一种合成Etelcalcetide的方法 |
| JP6991196B2 (ja) * | 2016-03-23 | 2022-02-03 | バッヘン・ホールディング・アクチエンゲゼルシャフト | グルカゴン様ペプチドを製造するための方法 |
| US10858390B2 (en) | 2016-09-02 | 2020-12-08 | Cem Corporation | Use of excess carbodiimide for peptide synthesis at elevated temperatures |
| CN108101959B (zh) * | 2016-11-24 | 2021-07-09 | 四川科伦药物研究院有限公司 | 一种制备高纯度多肽或其类似物的方法 |
| CN106928171B (zh) * | 2017-05-03 | 2019-08-13 | 成都郑源生化科技有限公司 | Fmoc-Arg（Pbf）-OH的合成方法 |
| TW201915009A (zh) * | 2017-10-03 | 2019-04-16 | 中化合成生技股份有限公司 | 合成依特卡肽（Ｅｔｅｌｃａｌｃｅｔｉｄｅ）或其鹽類之方法 |
| CN110498835B (zh) * | 2018-05-17 | 2021-06-08 | 深圳翰宇药业股份有限公司 | 一种合成etelcalcetide的方法 |
| CN109280078B (zh) * | 2018-10-30 | 2019-06-25 | 成都诺和晟泰生物科技有限公司 | 一种制备维拉卡肽的方法 |
| CN112062811B (zh) * | 2019-06-10 | 2022-03-25 | 深圳翰宇药业股份有限公司 | 一种维拉卡肽的合成方法 |
| EP4021920A4 (en) * | 2019-08-26 | 2023-08-16 | Auro Peptides LTD | IMPROVED PROCESS FOR THE PREPARATION OF ETELCALKETIDE HYDROCHLORIDE |
| EP3875466A1 (en) * | 2020-03-05 | 2021-09-08 | Fresenius Kabi iPSUM S.r.l. | Process for the synthesis of etelcalcetide |
| TW202210498A (zh) | 2020-06-03 | 2022-03-16 | 日商中外製藥股份有限公司 | 高難度序列之有效率的胜肽縮合法 |
| CN111925415A (zh) * | 2020-08-10 | 2020-11-13 | 海南中和药业股份有限公司 | 一种维拉卡肽杂质的制备方法 |
| TWI792442B (zh) * | 2021-07-23 | 2023-02-11 | 建誼生技股份有限公司 | 依特卡肽鹽酸鹽之製造方法 |
| CN114524860A (zh) * | 2021-12-29 | 2022-05-24 | 深圳翰宇药业股份有限公司 | 一种Etelcalcetide的合成方法及其应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3941763A (en) | 1975-03-28 | 1976-03-02 | American Home Products Corporation | PGlu-D-Met-Trp-Ser-Tyr-D-Ala-Leu-Arg-Pro-Gly-NH2 and intermediates |
| EP0339695A3 (en) | 1988-04-29 | 1990-05-30 | Stichting Voor De Technische Wetenschappen | A process for preparing an antigenic or immunogenic conjugate as well as the use of such conjugates |
| SE9603465D0 (sv) | 1996-09-23 | 1996-09-23 | Astra Ab | New compounds |
| NO311807B1 (no) * | 1999-03-04 | 2002-01-28 | Bionor Immuno As | HIV-peptider, antigener, vaksinepreparater, immunoassay- testsett og en metode for påvisning av antistoffer fremkalt av HIV |
| JP5473925B2 (ja) | 2007-10-27 | 2014-04-16 | コーデン ファーマ コロラド インコーポレイテッド | 固相および溶液相の組み合わせ技法を使用するインスリン分泌性ペプチドの合成 |
| CN101250172B (zh) | 2008-03-07 | 2012-05-02 | 上海瀚鸿化工科技有限公司 | 精氨酸双保护制备工艺 |
| US8742028B2 (en) | 2009-05-06 | 2014-06-03 | Mallinckrodt Llc | Solid support for Fmoc-solid phase synthesis of peptide acids |
| PT2459208T (pt) | 2009-07-29 | 2017-01-03 | Kai Pharmaceuticals Inc | Agentes terapêuticos para redução dos niveis de hormona paratiroideia |
| WO2011133346A1 (en) * | 2010-04-21 | 2011-10-27 | Pharmacofore, Inc. | Peripheral opioid agonists and peripheral opioid antagonists |
| WO2012031327A1 (en) * | 2010-09-08 | 2012-03-15 | Howard Florey Institute Of Experimental Physiology And Medicine | Modified relaxin polypeptides |
| WO2013042129A1 (en) | 2011-09-23 | 2013-03-28 | Natco Pharma Limited | Improved process for preparation of bivalirudin |
| CR20160002A (es) | 2013-06-28 | 2018-02-13 | Amgen Inc | Formulación estable líquida de etelcalcetide (amg 461) |
| MX2016012965A (es) | 2014-04-03 | 2017-07-06 | Amgen Inc | Metodo para preparar amg 416. |
| CN105504012A (zh) * | 2014-09-30 | 2016-04-20 | 深圳翰宇药业股份有限公司 | 一种多肽的制备方法 |
| CN107434820A (zh) * | 2017-08-07 | 2017-12-05 | 南京工业大学 | 一种维拉卡肽的合成方法 |
-
2015
- 2015-04-03 MX MX2016012965A patent/MX2016012965A/es active IP Right Grant
- 2015-04-03 EP EP20160369.3A patent/EP3708576B1/en active Active
- 2015-04-03 MA MA052906A patent/MA52906A/fr unknown
- 2015-04-03 CA CA2944194A patent/CA2944194C/en active Active
- 2015-04-03 BR BR112016022868-5A patent/BR112016022868A2/pt active Search and Examination
- 2015-04-03 HU HUE15773570A patent/HUE048489T2/hu unknown
- 2015-04-03 ES ES20160369T patent/ES2943671T3/es active Active
- 2015-04-03 WO PCT/US2015/024347 patent/WO2015154031A1/en active Application Filing
- 2015-04-03 JP JP2016560462A patent/JP6710158B2/ja active Active
- 2015-04-03 ES ES15773570T patent/ES2786225T3/es active Active
- 2015-04-03 CN CN201580029560.2A patent/CN106795201A/zh active Pending
- 2015-04-03 MA MA39628A patent/MA39628B1/fr unknown
- 2015-04-03 EP EP15773570.5A patent/EP3126373B1/en active Active
- 2015-04-03 AU AU2015240527A patent/AU2015240527B2/en active Active
- 2015-04-03 PT PT157735705T patent/PT3126373T/pt unknown
- 2015-04-03 ME MEP-2020-83A patent/ME03781B/me unknown
- 2015-04-03 EA EA201692001A patent/EA032597B1/ru not_active IP Right Cessation
- 2015-04-03 KR KR1020167030590A patent/KR102397271B1/ko active IP Right Grant
- 2015-04-03 DK DK15773570.5T patent/DK3126373T3/da active
- 2015-04-03 SI SI201531173T patent/SI3126373T1/sl unknown
- 2015-04-03 EP EP23150870.6A patent/EP4219526A3/en active Pending
- 2015-04-03 LT LTEP15773570.5T patent/LT3126373T/lt unknown
- 2015-04-03 US US15/300,209 patent/US10407464B2/en active Active
- 2015-04-03 IL IL248059A patent/IL248059B2/en unknown
- 2015-04-03 RS RS20200448A patent/RS60187B1/sr unknown
- 2015-04-03 SG SG11201608176VA patent/SG11201608176VA/en unknown
- 2015-04-03 PL PL15773570T patent/PL3126373T3/pl unknown
-
2016
- 2016-10-03 CL CL2016002513A patent/CL2016002513A1/es unknown
- 2016-10-05 ZA ZA2016/06844A patent/ZA201606844B/en unknown
-
2019
- 2019-08-05 US US16/532,344 patent/US11377474B2/en active Active
-
2020
- 2020-04-01 HR HRP20200527TT patent/HRP20200527T1/hr unknown
- 2020-04-29 CY CY20201100391T patent/CY1123100T1/el unknown
-
2022
- 2022-06-28 US US17/852,263 patent/US20230099078A1/en not_active Abandoned
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