CA2980960C - Solution phase method for preparing etelcalcetide - Google Patents

Solution phase method for preparing etelcalcetide Download PDF

Info

Publication number
CA2980960C
CA2980960C CA2980960A CA2980960A CA2980960C CA 2980960 C CA2980960 C CA 2980960C CA 2980960 A CA2980960 A CA 2980960A CA 2980960 A CA2980960 A CA 2980960A CA 2980960 C CA2980960 C CA 2980960C
Authority
CA
Canada
Prior art keywords
etelcalcetide
protected
arg
ala
coupling
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
Application number
CA2980960A
Other languages
English (en)
French (fr)
Other versions
CA2980960A1 (en
Inventor
Sheng CUI
Krishnakumar Ranganathan
Richard Crockett
Ying Chen
Aleksander Swietlow
Kevin CROSSLEY
Yun SHI
Karel DECROOS
Etienne MONIOTTE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Amgen Inc
Original Assignee
Amgen Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Amgen Inc filed Critical Amgen Inc
Publication of CA2980960A1 publication Critical patent/CA2980960A1/en
Application granted granted Critical
Publication of CA2980960C publication Critical patent/CA2980960C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07K1/026—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution by fragment condensation in solution
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
    • A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
    • 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
    • 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
    • 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
    • C07K1/14—Extraction; Separation; Purification
    • C07K1/16—Extraction; Separation; Purification by chromatography
    • C07K1/18—Ion-exchange chromatography
    • 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
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/081—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
    • 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
    • C07K5/1019—Tetrapeptides with the first amino acid being basic
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Diabetes (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Endocrinology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Rheumatology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2980960A 2015-03-26 2016-03-25 Solution phase method for preparing etelcalcetide Active CA2980960C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562138903P 2015-03-26 2015-03-26
US62/138,903 2015-03-26
PCT/US2016/024308 WO2016154580A1 (en) 2015-03-26 2016-03-25 Solution phase method for preparing etelcalcetide

Publications (2)

Publication Number Publication Date
CA2980960A1 CA2980960A1 (en) 2016-09-29
CA2980960C true CA2980960C (en) 2024-05-28

Family

ID=55911037

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2980960A Active CA2980960C (en) 2015-03-26 2016-03-25 Solution phase method for preparing etelcalcetide

Country Status (7)

Country Link
US (1) US10858389B2 (enExample)
EP (1) EP3274360B1 (enExample)
JP (1) JP6783787B2 (enExample)
AU (1) AU2016238233B2 (enExample)
CA (1) CA2980960C (enExample)
ES (1) ES2806200T3 (enExample)
WO (1) WO2016154580A1 (enExample)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10858389B2 (en) 2015-03-26 2020-12-08 Amgen Inc. Solution phase method for preparing etelcalcetide
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
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
CN106967155B (zh) * 2017-03-17 2018-05-15 兰州凯博药业股份有限公司 一种多肽液相合成缩宫素的方法
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
EP3613757A1 (en) * 2018-08-20 2020-02-26 Wntresearch AB Solution phase routes for wnt hexapeptides
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
CN109734778A (zh) * 2019-03-07 2019-05-10 苏州科技大学 一种维拉卡肽的制备方法
CN112175042B (zh) * 2019-07-03 2022-05-31 深圳翰宇药业股份有限公司 Etelcalcetide的合成方法
WO2021038431A1 (en) 2019-08-26 2021-03-04 Auro Peptides Ltd An improved process for the preparation of etelcalcetide hydrochloride
CN112521450A (zh) * 2019-09-19 2021-03-19 深圳市健翔生物制药有限公司 一种固液相结合制备维拉卡肽的方法
CN110668984B (zh) * 2019-12-03 2020-04-10 凯莱英医药集团（天津）股份有限公司 一种依特卡肽中间体及依特卡肽的合成方法
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
EP4204434A1 (en) 2020-08-31 2023-07-05 USV Private Limited An improved process for fmoc synthesis of etelcalcetide
WO2026002733A1 (en) * 2024-06-24 2026-01-02 Fresenius Kabi Ipsum S.R.L. Method for the synthesis of a peptide with amino acids having basic side-chains
CN120699096B (zh) * 2025-07-07 2026-01-23 苏州天马医药集团天吉生物制药有限公司 一种依特卡肽的制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4738683B2 (ja) * 1999-07-19 2011-08-03 ジーイー・ヘルスケア・アクスイェ・セルスカプ 保護されたチオールを脱保護する方法
WO2009152850A1 (en) 2008-06-17 2009-12-23 Solvay (Société Anonyme) Peptide manufacturing process
ES2729051T3 (es) 2009-07-29 2019-10-30 Kai Pharmaceuticals Inc Agentes terapéuticos para reducir los niveles de hormona paratiroidea
WO2012068187A1 (en) 2010-11-19 2012-05-24 Merck Sharp & Dohme Corp. Poly(amide) polymers for the delivery of oligonucleotides
CA2916222C (en) * 2013-06-28 2021-05-18 Amgen Inc. Stable liquid formulation of amg 416 (etelcalcetide)
US10858389B2 (en) 2015-03-26 2020-12-08 Amgen Inc. Solution phase method for preparing etelcalcetide

Also Published As

Publication number Publication date
ES2806200T3 (es) 2021-02-16
EP3274360B1 (en) 2020-05-06
US20180079777A1 (en) 2018-03-22
US10858389B2 (en) 2020-12-08
CA2980960A1 (en) 2016-09-29
AU2016238233B2 (en) 2019-11-21
WO2016154580A1 (en) 2016-09-29
JP2018512415A (ja) 2018-05-17
JP6783787B2 (ja) 2020-11-11
EP3274360A1 (en) 2018-01-31
AU2016238233A1 (en) 2017-10-19

Similar Documents

Publication Publication Date Title
CA2980960C (en) Solution phase method for preparing etelcalcetide
US20230099078A1 (en) Method for preparing amg 416 (etelcalcetide)
US6255285B1 (en) Phenethylamine derivatives
EP4269422A1 (en) Method for producing peptide compound containing n-substituted-amino acid residue
US6235876B1 (en) Liquid phase process for the preparation of GNRH peptides
JP5212371B2 (ja) ペプチドの製造方法
JP5445456B2 (ja) ジベンゾフルベンの除去方法
JP2000044595A (ja) フェネチルアミン誘導体
HK40036914A (en) Method for preparing amg 416
JP3554399B2 (ja) ペプチド誘導体
EP4436980A1 (en) Synthetic process for production of modified gcc receptor agonists
HK1233655A1 (en) Method for preparing amg 416
HK1233655B (en) Method for preparing amg 416
NO177100B (no) Peptider
WO2006097693A1 (en) Convergent solid phase peptide synthesis by reaction of two fragments bound to solid support
HK1028409A (en) Phenethylamine derivatives

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20210104

EEER Examination request

Effective date: 20210104

EEER Examination request

Effective date: 20210104

EEER Examination request

Effective date: 20210104

EEER Examination request

Effective date: 20210104

EEER Examination request

Effective date: 20210104

EEER Examination request

Effective date: 20210104

EEER Examination request

Effective date: 20210104

EEER Examination request

Effective date: 20210104

EEER Examination request

Effective date: 20210104

EEER Examination request

Effective date: 20210104

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 9TH ANNIV.) - STANDARD

Year of fee payment: 9

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20250226

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20250226