GB2535004A - A process for the preparation of Lenalidomide - Google Patents

A process for the preparation of Lenalidomide Download PDF

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Publication number
GB2535004A
GB2535004A GB1522674.9A GB201522674A GB2535004A GB 2535004 A GB2535004 A GB 2535004A GB 201522674 A GB201522674 A GB 201522674A GB 2535004 A GB2535004 A GB 2535004A
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GB
United Kingdom
Prior art keywords
isoindol
dione
piperidine
dihydro
oxo
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.)
Granted
Application number
GB1522674.9A
Other versions
GB2535004B (en
GB201522674D0 (en
Inventor
Kalvins Ivars
Ponomarjovs Jurijs
Varaceva Larisa
Cernobrovijs Aleksandrs
Lebedevs Antons
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.)
Latvian Institute of Organic Synthesis
Original Assignee
Latvian Institute of Organic Synthesis
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Filing date
Publication date
Application filed by Latvian Institute of Organic Synthesis filed Critical Latvian Institute of Organic Synthesis
Publication of GB201522674D0 publication Critical patent/GB201522674D0/en
Publication of GB2535004A publication Critical patent/GB2535004A/en
Application granted granted Critical
Publication of GB2535004B publication Critical patent/GB2535004B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Improvements in the preparation process of 3-(4-amino-1-oxo-1,3-dihydro-2H- isoindol-2-yl)piperidine-2,6-dione (Ienalidomide), wherein the intermediate 2-methyl- 3-nitrobenzoic acid methyl ester is brominatcd with N-bromosuccinimide in methyl acetate and the end product is obtained from 3-(4-nitro-l-oxo-l,3-dihydro- 2H-isoindol-2-yl)piperidine-2,6-dione by reducing with iron and ammonium chloride reducing system.
GB1522674.9A 2013-10-14 2014-10-03 A process for the preparation of Lenalidomide Active GB2535004B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
LVP-13-152A LV14985B (en) 2013-10-14 2013-10-14 Method for production of lenalidomide
PCT/LV2014/000010 WO2015057043A1 (en) 2013-10-14 2014-10-03 A process for the preparation of lenalidomide

Publications (3)

Publication Number Publication Date
GB201522674D0 GB201522674D0 (en) 2016-02-03
GB2535004A true GB2535004A (en) 2016-08-10
GB2535004B GB2535004B (en) 2019-01-02

Family

ID=51794944

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1522674.9A Active GB2535004B (en) 2013-10-14 2014-10-03 A process for the preparation of Lenalidomide

Country Status (3)

Country Link
GB (1) GB2535004B (en)
LV (1) LV14985B (en)
WO (1) WO2015057043A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX369968B (en) * 2014-08-19 2019-11-27 Synthon Bv Process for making crystalline form a of lenalidomide.
CN109400579B (en) * 2017-08-18 2020-06-23 新发药业有限公司 Production method of lenalidomide
CN107337666B (en) * 2017-08-30 2019-06-04 上海万巷制药有限公司 It is a kind of for treating the preparation method of the lenalidomide of Huppert's disease

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1847532A1 (en) * 2005-01-27 2007-10-24 Kyowa Hakko Kogyo Co., Ltd. Igf-1r inhibitor
WO2010061209A1 (en) * 2008-11-03 2010-06-03 Generics [Uk] Limited A crystalline form of lenalidomide and a process for its preparation
WO2011111053A1 (en) * 2010-03-08 2011-09-15 Natco Pharma Limited Anhydrous lenalidomide form-i

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1048246C (en) 1993-06-25 2000-01-12 组合化学工业株式会社 Indazolesulfonylurea derivative, use thereof, and intermediate for production thereof
US6281230B1 (en) 1996-07-24 2001-08-28 Celgene Corporation Isoindolines, method of use, and pharmaceutical compositions
NZ531294A (en) 2001-08-06 2005-11-25 Childrens Medical Center Synthesis and anti-tumor activity of nitrogen substituted thalidomide analogs
DE102006025317A1 (en) 2006-05-31 2007-12-06 Bayer Healthcare Aktiengesellschaft Isoindolin-1-one, isoindolin-3-one and isoindoline-1,3-dione derivatives and their use
WO2009114601A2 (en) 2008-03-11 2009-09-17 Dr. Reddy's Laboratories Ltd. Preparation of lenalidomide
EP2373165B1 (en) 2008-11-14 2013-10-30 Concert Pharmaceuticals, Inc. Substituted dioxopiperidinyl phthalimide derivaties
EP2350055A4 (en) 2008-11-17 2012-04-18 Reddys Lab Ltd Dr Lenalidomide solvates and processes
DK2403845T3 (en) 2009-03-02 2014-08-04 Generics Uk Ltd Improved process.
CN101580501B (en) 2009-06-01 2011-03-09 南京卡文迪许生物工程技术有限公司 Synthetic method of 3-(substituted dihydro-isoindolone-2-group)-2,6-dioxopiperidine and intermediate thereof
AU2010290822A1 (en) 2009-09-03 2012-03-29 Ranbaxy Laboratories Limited Process for the preparation of lenalidomide
WO2011050962A1 (en) 2009-10-29 2011-05-05 Ratiopharm Gmbh Acid addition salts of lenalidomide
WO2011069608A1 (en) 2009-12-09 2011-06-16 Ratiopharm Gmbh S-lenalidomide, polymorphic forms thereof and blend comprising s- und r-lenalidomide
MX2012010367A (en) 2010-03-12 2012-11-23 Celgene Corp Methods for the treatment of non-hodgkin's lymphomas using lenalidomide, and gene and protein biomarkers as a predictor.

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1847532A1 (en) * 2005-01-27 2007-10-24 Kyowa Hakko Kogyo Co., Ltd. Igf-1r inhibitor
WO2010061209A1 (en) * 2008-11-03 2010-06-03 Generics [Uk] Limited A crystalline form of lenalidomide and a process for its preparation
WO2011111053A1 (en) * 2010-03-08 2011-09-15 Natco Pharma Limited Anhydrous lenalidomide form-i

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
A. N. BALAEV, K. A. OKHMANOVICH, V. E. FEDOROV: "Alternative synthesis of lenalidomide", PHARMACEUTICAL CHEMISTRY JOURNAL, vol. 46, no. 11, 1 February 2013 (2013-02-01), pages 676 - 678, XP055152353, ISSN: 0091150X, DOI: 10.1007/s11094-013-0868-7 *
LUKE W. JUDD, ANTHONY P. DAVIS: "From cholapod to cholaphane transmembrane anion carriers: accelerated transport through binding site enclosure", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, vol. 46, no. 13, 1 January 2010 (2010-01-01), pages 2227, XP055152266, ISSN: 13597345, DOI: 10.1039/b927005a *
MARIA BARBOSA, CASTRO BARBOSA, THIAGO JOSÉ, FIGUEIRA RAMOS, ANA CAROLINA SANTOS DE ARANTES, MARCO AURÉLIO MARTINS, PATRÍCIA MACHAD: "Synthesis and Pharmacological Evaluation of Novel Phenyl Sulfonamide Derivatives Designed as Modulators of Pulmonary Inflammatory Response", MOLECULES, vol. 17, no. 12, 1 January 2012 (2012-01-01), pages 14651 - 14672, XP055152660, DOI: 10.3390/molecules171214651 *
MULLER, G.W. CHEN, R. HUANG, S.-Y. CORRAL, L.G. WONG, L.M. PATTERSON, R.T. CHEN, Y. KAPLAN, G. STIRLING, D.I.: "Amino-substituted thalidomide analogs: potent inhibitors of TNF-@a production", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, AMSTERDAM, NL, vol. 9, no. 11, 7 June 1999 (1999-06-07), AMSTERDAM, NL, pages 1625 - 1630, XP004169632, ISSN: 0960-894X, DOI: 10.1016/S0960-894X(99)00250-4 *

Also Published As

Publication number Publication date
GB2535004B (en) 2019-01-02
LV14985A (en) 2015-04-20
LV14985B (en) 2015-06-20
GB201522674D0 (en) 2016-02-03
WO2015057043A1 (en) 2015-04-23

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