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
Application number
PCT/CA2003/001744
Other languages
French (fr)
Other versions
WO2004043995A2 (en
Inventor
Elena Bejan
Gamini Weeratunga
Stephen E Horne
Original Assignee
Apotex Pharmachem Inc
Elena Bejan
Gamini Weeratunga
Stephen E Horne
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, Elena Bejan, Gamini Weeratunga, Stephen E Horne filed Critical Apotex Pharmachem Inc
Priority to AU2003283152A priority Critical patent/AU2003283152A1/en
Priority to EP03775017A priority patent/EP1565486A2/en
Publication of WO2004043995A2 publication Critical patent/WO2004043995A2/en
Publication of WO2004043995A3 publication Critical patent/WO2004043995A3/en

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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 WO2004043995A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
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
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

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CA2,411,786 2002-11-13
CA002411786A CA2411786C (en) 2002-11-13 2002-11-13 A process for the preparation of polypeptides from n-carboxyanhydrides of amino acids
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

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA2003/001744 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 (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SI1459065T1 (en) 2001-12-04 2010-11-30 Teva Pharma Processes for the measurement of the potency of glatiramer acetate
DE602005018800D1 (en) * 2004-09-09 2010-02-25 Teva Pharma METHOD FOR THE PRODUCTION OF POLYPEPTIDE MIXTURES USING PURIFICED BROMINE HYDROGEN ACID
EP1797109B1 (en) * 2004-09-09 2016-02-24 Yeda Research And Development Co., Ltd. Mixtures of polypeptides, compositions containing and processes for preparing same, and uses thereof
JP5297653B2 (en) 2004-10-29 2013-09-25 サンド・アクチエンゲゼルシヤフト Manufacturing method of glatiramer
UA93669C2 (en) * 2005-02-02 2011-03-10 Тева Фармасьютикл Индастриз, Лтд. Process for producing 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
EP2381254B2 (en) 2007-06-21 2017-07-19 Momenta Pharmaceuticals, Inc. Copolymer assay
US8993722B2 (en) 2007-07-31 2015-03-31 Natco Pharma Limited Process for the preparation glatiramer acetate (copolymer-1)
EP2277050B2 (en) 2008-04-16 2022-09-28 Momenta Pharmaceuticals, Inc. Analysis of amino acid copolymer compositions
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
NZ609938A (en) 2010-10-11 2015-11-27 Teva Pharma 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
EP3600553A4 (en) 2017-03-26 2020-09-02 Mapi Pharma Ltd. Glatiramer depot systems for treating progressive forms of multiple sclerosis

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

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