WO2004043995A3 - Process for the preparation of glatiramer acetate by polymerisation of n-carboxy anhydrides of l-alanine, l-tyrosine, benzyl l-glutamate and benzyloxycarbonyl l-lysine - Google Patents

Process for the preparation of glatiramer acetate by polymerisation of n-carboxy anhydrides of l-alanine, l-tyrosine, benzyl l-glutamate and benzyloxycarbonyl l-lysine Download PDF

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Publication number
WO2004043995A3
WO2004043995A3 PCT/CA2003/001744 CA0301744W WO2004043995A3 WO 2004043995 A3 WO2004043995 A3 WO 2004043995A3 CA 0301744 W CA0301744 W CA 0301744W WO 2004043995 A3 WO2004043995 A3 WO 2004043995A3
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WO
WIPO (PCT)
Prior art keywords
alanine
tyrosine
lysine
polypeptide
glutamate
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.)
Ceased
Application number
PCT/CA2003/001744
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French (fr)
Other versions
WO2004043995A2 (en
Inventor
Elena Bejan
Gamini Weeratunga
Stephen E Horne
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.)
Apotex Pharmachem Inc
Original Assignee
Apotex Pharmachem 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
Priority claimed from CA002411786A external-priority patent/CA2411786C/en
Application filed by Apotex Pharmachem Inc filed Critical Apotex Pharmachem Inc
Priority to EP03775017A priority Critical patent/EP1565486A2/en
Priority to AU2003283152A priority patent/AU2003283152A1/en
Publication of WO2004043995A2 publication Critical patent/WO2004043995A2/en
Publication of WO2004043995A3 publication Critical patent/WO2004043995A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Peptides Or Proteins (AREA)
  • Polyamides (AREA)

Abstract

A process for the preparation of a polypeptide designated in the present invention as 1, composed of the following amino acid units in the structure, namely: L-alanine, L-glutamic acid, L-lysine and L-tyrosine randomly arranged in the polypeptide 1, or pharmaceutically acceptable salts thereof, comprising the steps of: (a) polymerization of a mixture of the N-carboxyanhydrides of L-alanine, L-tyrosine, a protected L-glutamate and a protected L-lysine to obtain protected copolymer 6 or salt thereof; formula (I), (b) deprotection of the protected copolymer 6 (or salt thereof) to produce polypeptide 1 or a pharmaceutically acceptable salt thereof in one single step; formula (II), (c) separation and purification of the polypeptide 1 (or a pharmaceutically acceptable salt) to obtain a purified polypeptide 1. Formula (III).
PCT/CA2003/001744 2002-11-13 2003-11-13 Process for the preparation of glatiramer acetate by polymerisation of n-carboxy anhydrides of l-alanine, l-tyrosine, benzyl l-glutamate and benzyloxycarbonyl l-lysine Ceased WO2004043995A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP03775017A EP1565486A2 (en) 2002-11-13 2003-11-13 Process for the preparation of glatiramer acetate by polymerisation of n-carboxy anhydrides of l-alanine, l-tyrosine, benzyl l-glutamate and benzyloxycarbonyl l-lysine
AU2003283152A AU2003283152A1 (en) 2002-11-13 2003-11-13 Process for the preparation of glatiramer acetate by polymerisation of n-carboxy anhydrides of l-alanine, l-tyrosine, benzyl l-glutamate and benzyloxycarbonyl l-lysine

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CA002411786A CA2411786C (en) 2002-11-13 2002-11-13 A process for the preparation of polypeptides from n-carboxyanhydrides of amino acids
CA2,411,786 2002-11-13
US10/326,994 2002-12-24
US10/326,994 US7049399B2 (en) 2002-11-13 2002-12-24 Process for the preparation of polypeptide 1

Publications (2)

Publication Number Publication Date
WO2004043995A2 WO2004043995A2 (en) 2004-05-27
WO2004043995A3 true WO2004043995A3 (en) 2004-10-07

Family

ID=32313425

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA2003/001744 Ceased WO2004043995A2 (en) 2002-11-13 2003-11-13 Process for the preparation of glatiramer acetate by polymerisation of n-carboxy anhydrides of l-alanine, l-tyrosine, benzyl l-glutamate and benzyloxycarbonyl l-lysine

Country Status (3)

Country Link
EP (1) EP1565486A2 (en)
AU (1) AU2003283152A1 (en)
WO (1) WO2004043995A2 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9402874B2 (en) 2009-08-20 2016-08-02 Yeda Research & Development Co., Ltd. Low frequency glatiramer acetate therapy
US9499868B2 (en) 2011-10-10 2016-11-22 Teva Pharmaceutical Industries, Ltd. Determination of single nucleotide polymorphisms useful to predict response for glatiramer acetate

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7429374B2 (en) 2001-12-04 2008-09-30 Teva Pharmaceutical Industries, Ltd. Process for the measurement of the potency of glatiramer acetate
ZA200702591B (en) 2004-09-09 2009-03-25 Teva Pharma Process for preparation of mixtures of polypeptides using purified hydrobromic acid
HRP20160455T1 (en) 2004-09-09 2016-07-15 Yeda Research And Development Co., Ltd. Mixtures of polypeptides, their compositions and methods for their preparation, and their uses
AR052321A1 (en) 2004-10-29 2007-03-14 Sandoz Ag PROCESSES FOR THE PREPARATION OF A POLYPEPTIDE
JP2008528589A (en) * 2005-02-02 2008-07-31 テバ ファーマシューティカル インダストリーズ リミティド Method for making polypeptide mixtures using hydrogenolysis
JP2009542864A (en) * 2006-07-05 2009-12-03 モメンタ ファーマシューティカルズ インコーポレイテッド Improved method for the preparation of copolymer 1
US8753833B2 (en) 2007-06-21 2014-06-17 Momenta Pharmaceuticals, Inc. Copolymer assay
US8993722B2 (en) 2007-07-31 2015-03-31 Natco Pharma Limited Process for the preparation glatiramer acetate (copolymer-1)
ES2449865T5 (en) 2008-04-16 2022-11-18 Momenta Pharmaceuticals Inc Analysis of compositions of amino acid copolymers
USRE49251E1 (en) 2010-01-04 2022-10-18 Mapi Pharma Ltd. Depot systems comprising glatiramer or pharmacologically acceptable salt thereof
US8759302B2 (en) 2010-03-16 2014-06-24 Teva Pharmaceutical Industries, Ltd. Methods of treating a subject afflicted with an autoimmune disease using predictive biomarkers of clinical response to glatiramer acetate therapy in multiple sclerosis
CA2814500A1 (en) 2010-10-11 2012-04-19 Teva Pharmaceutical Industries Ltd Cytokine biomarkers as predictive biomarkers of clinical response for glatiramer acetate
WO2013009885A2 (en) 2011-07-11 2013-01-17 Momenta Pharmaceuticals, Inc. Evaluation of copolymer diethylamide
US12097292B2 (en) 2016-08-28 2024-09-24 Mapi Pharma Ltd. Process for preparing microparticles containing glatiramer acetate
CN109982712A (en) 2016-08-31 2019-07-05 Mapi医药公司 Depot system containing glatiramer acetate
CN110382052A (en) 2017-03-26 2019-10-25 Mapi医药公司 The copaxone store system of multiple sclerosis for therapeutic advance type form

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3849550A (en) * 1971-04-21 1974-11-19 Yeda Res & Dev Therapeutic copolymer

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3849550A (en) * 1971-04-21 1974-11-19 Yeda Res & Dev Therapeutic copolymer

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
EPTON R ET AL: "CATALYTIC TRANSFER HYDROGENATION OF POLY(ACRYLOYLMORPHOLINE)-BASED PEPTIDE-RESIN ASSEMBLIES AND OF DERIVED PEPTIDE SEGMENTS", POLYMER OCT 1982, vol. 23, no. 11, October 1982 (1982-10-01), pages 1685 - 1687, XP001180305 *
FELIX A M ET AL: "RAPID REMOVAL OF PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH 1 4 CYCLO HEXADIENE", JOURNAL OF ORGANIC CHEMISTRY, vol. 43, no. 21, 1978, pages 4194 - 4196, XP002273767, ISSN: 0022-3263 *
GOWDA D CHANNE ET AL: "Heterogeneous catalytic transfer hydrogenation in peptide synthesis.", LETTERS IN PEPTIDE SCIENCE, vol. 9, no. 4-5, 2002, pages 153 - 165, XP009027879, ISSN: 0929-5666 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9402874B2 (en) 2009-08-20 2016-08-02 Yeda Research & Development Co., Ltd. Low frequency glatiramer acetate therapy
US9499868B2 (en) 2011-10-10 2016-11-22 Teva Pharmaceutical Industries, Ltd. Determination of single nucleotide polymorphisms useful to predict response for glatiramer acetate

Also Published As

Publication number Publication date
EP1565486A2 (en) 2005-08-24
AU2003283152A1 (en) 2004-06-03
WO2004043995A2 (en) 2004-05-27
AU2003283152A8 (en) 2004-06-03

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