AR083523A1 - PROCEDURE FOR OBTAINING OLMESARTAN MEDOXOMILO - Google Patents

PROCEDURE FOR OBTAINING OLMESARTAN MEDOXOMILO

Info

Publication number
AR083523A1
AR083523A1 ARP110103905A AR083523A1 AR 083523 A1 AR083523 A1 AR 083523A1 AR P110103905 A ARP110103905 A AR P110103905A AR 083523 A1 AR083523 A1 AR 083523A1
Authority
AR
Argentina
Prior art keywords
formula
compound
acetone
medium
acetonitrile
Prior art date
Application number
Other languages
Spanish (es)
Inventor
Iban Jove
Francisco Marquillas
Original Assignee
Interquim Sa
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 Interquim Sa filed Critical Interquim Sa
Publication of AR083523A1 publication Critical patent/AR083523A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Abstract

Procedimiento de obtención del olmesartan medoxomilo por reacción del 5-(1-hidroxi-1-metiletil)-2-propil-3-[2’-(1-tritil-1H-tetrazol-5-il)bifeniI-4-ilmetiI]-3H-imidazoI-4-carboxilato sódico, obtenido por reacción entre 5-(1-hidroxi-1-metiletil)-2-propil-3H-imidazol-4-carboxilato de etilo y 5-(4’-bromometilbifenil-2-il)-1-tritil-1H-tetrazol seguido de saponificación, con 4-(clorometil)-5-metil-1,3-dioxol-2-ona, desprotección y purificación.Reivindicación 1: Procedimiento de obtención del olmesartan medoxomilo de formula (6) caracterizado porque comprende las siguientes etapas: (i) alquilación del compuesto de fórmula (1) con el compuesto de fórmula (2) en presencia de tert-butóxido potásico y en un medio que comprende un disolvente seleccionado del grupo consistente acetato de etilo, acetona, dimetilsulfóxido, metiletilcetona, metil tert-butil éter, tetrahidrofurano y tolueno, y sus mezclas; (ii) saponificación del compuesto formado en (i), de fórmula (3) en presencia de hidróxido sódico, y en un medio que comprende un disolvente seleccionado del grupo consistente en dimetilsulfóxido, 2-metil tetrahidrofurano y tetrahidrofurano, y sus mezclas, para dar la sal intermedia de fórmula (3-Na) que reacciona in situ con el compuesto de fórmula (4) en presencia de carbonato potásico, y en un medio que comprende un disolvente seleccionado del grupo consistente en acetona, dimetilsulfóxido, 2-metiltetrahidrofurano y tetrahidrofurano, y sus mezclas; (iii) desprotección del compuesto formado en (ii), de fórmula (5) en un medio que comprende una disolución acuosa de un ácido mineral seleccionado del grupo consistente en los ácidos clorhídrico, bromhídrico, fosfórico, nítrico y sulfúrico, y acetona o acetonitrilo, seguido de separación del compuesto resultante de fórmula (6) por cristalización mediante adición de tolueno ajustando el pH de la fase acuosa a 4.5 - 6.0, eliminación a presión reducida de la acetona o el acetonitrilo, y filtración; y (iv) purificación final del compuesto de fórmula (6) por disolución en un medio que comprende acetonitrilo o mezclas de acetonitrilo con metanol o con acetona, a reflujo, seguido de cristalización.Procedure for obtaining olmesartan medoxomil by reaction of 5- (1-hydroxy-1-methylethyl) -2-propyl-3- [2 '- (1-trityl-1H-tetrazol-5-yl) biphenyI-4-ylmetiI] -3H-sodium imidazoI-4-carboxylate, obtained by reaction between ethyl 5- (1-hydroxy-1-methylethyl) -2-propyl-3H-imidazol-4-carboxylate and 5- (4'-bromomethylbiphenyl-2- il) -1-trityl-1H-tetrazole followed by saponification, with 4- (chloromethyl) -5-methyl-1,3-dioxol-2-one, deprotection and purification. Claim 1: Method for obtaining olmesartan medoxomil of formula (6) characterized in that it comprises the following steps: (i) alkylation of the compound of formula (1) with the compound of formula (2) in the presence of potassium tert-butoxide and in a medium comprising a solvent selected from the group consisting of acetate of ethyl, acetone, dimethylsulfoxide, methyl ethyl ketone, methyl tert-butyl ether, tetrahydrofuran and toluene, and mixtures thereof; (ii) saponification of the compound formed in (i), of formula (3) in the presence of sodium hydroxide, and in a medium comprising a solvent selected from the group consisting of dimethylsulfoxide, 2-methyl tetrahydrofuran and tetrahydrofuran, and mixtures thereof, for giving the intermediate salt of formula (3-Na) which reacts in situ with the compound of formula (4) in the presence of potassium carbonate, and in a medium comprising a solvent selected from the group consisting of acetone, dimethyl sulfoxide, 2-methyltetrahydrofuran and tetrahydrofuran, and mixtures thereof; (iii) deprotection of the compound formed in (ii), of formula (5) in a medium comprising an aqueous solution of a mineral acid selected from the group consisting of hydrochloric, hydrobromic, phosphoric, nitric and sulfuric acids, and acetone or acetonitrile , followed by separation of the resulting compound of formula (6) by crystallization by adding toluene by adjusting the pH of the aqueous phase to 4.5 - 6.0, removal under reduced pressure of acetone or acetonitrile, and filtration; and (iv) final purification of the compound of formula (6) by dissolution in a medium comprising acetonitrile or mixtures of acetonitrile with methanol or with acetone, at reflux, followed by crystallization.

ARP110103905 2010-10-29 2011-10-21 PROCEDURE FOR OBTAINING OLMESARTAN MEDOXOMILO AR083523A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES201031597 2010-10-29

Publications (1)

Publication Number Publication Date
AR083523A1 true AR083523A1 (en) 2013-03-06

Family

ID=44913259

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP110103905 AR083523A1 (en) 2010-10-29 2011-10-21 PROCEDURE FOR OBTAINING OLMESARTAN MEDOXOMILO

Country Status (4)

Country Link
AR (1) AR083523A1 (en)
TW (1) TW201217363A (en)
UY (1) UY33691A (en)
WO (1) WO2012055994A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103012382B (en) * 2012-12-05 2016-10-05 迪沙药业集团有限公司 A kind of preparation method of olmesartan medoxomil
CN103435602A (en) * 2013-07-31 2013-12-11 山东省医学科学院药物研究所 Preparation method of olmesartan medoxomil
CN103724333B (en) * 2013-12-26 2016-06-08 南通康鑫药业有限公司 A kind of synthetic method of olmesartan medoxomil
CN104592213A (en) * 2014-12-15 2015-05-06 山东新华制药股份有限公司 Preparation method of olmesartan intermediate
CN107311990B (en) * 2017-07-25 2021-09-03 浙江华海致诚药业有限公司 Preparation method of olmesartan medoxomil

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5616599A (en) 1991-02-21 1997-04-01 Sankyo Company, Limited Angiotensin II antagosist 1-biphenylmethylimidazole compounds and their therapeutic use
US20070054948A1 (en) 2004-09-02 2007-03-08 Lilach Hedvati Purification of olmesartan medoxomil
CA2573800A1 (en) 2004-09-02 2006-03-16 Teva Pharmaceutical Industries Ltd. Preparation of olmesartan medoxomil
US20060074117A1 (en) 2004-09-02 2006-04-06 Lilach Hedvati Purification of olmesartan medoxomil
KR20070086402A (en) 2004-12-30 2007-08-27 테바 파마슈티컬 인더스트리즈 리미티드 Process for preparing olmesartan medoxomil at ph higher than 2.5
US20060258727A1 (en) 2005-01-03 2006-11-16 Lilach Hedvati Olmesartan medoxomil with reduced levels of impurities
EP1816131A1 (en) 2006-02-06 2007-08-08 KRKA, tovarna zdravil, d.d., Novo mesto Process for the preparation of olmesartan medoxomil
EP1910343B1 (en) 2005-07-29 2014-10-29 Krka Process for the preparation of olmesartan medoxomil
WO2007047838A2 (en) 2005-10-20 2007-04-26 Dr. Reddy's Laboratories Ltd. Process for preparing olmesartan medoxomil
CZ299902B6 (en) 2005-10-27 2008-12-29 Zentiva, A. S Method of removing triphenylmethane-protecting group from precursors of antihypertensive drugs
WO2007148344A2 (en) 2006-06-19 2007-12-27 Matrix Laboratories Limited Process for the preparation of olmesartan medoxomil
US8076492B2 (en) 2006-10-09 2011-12-13 Cipla Limited Process for preparing trityl olmesartan medoxomil and olmesartan medoxomil
EP1916246A3 (en) 2006-10-11 2008-06-18 Cadila Pharmaceuticals Limited An improved process for the preparation of olmesartan medoxomil

Also Published As

Publication number Publication date
UY33691A (en) 2012-04-30
WO2012055994A1 (en) 2012-05-03
TW201217363A (en) 2012-05-01

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