AR083523A1 - Procedimiento de obtencion del olmesartan medoxomilo - Google Patents
Procedimiento de obtencion del olmesartan medoxomiloInfo
- 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
Links
- 238000000034 method Methods 0.000 title abstract 3
- 239000005480 Olmesartan Substances 0.000 title 1
- VTRAEEWXHOVJFV-UHFFFAOYSA-N olmesartan Chemical compound CCCC1=NC(C(C)(C)O)=C(C(O)=O)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 VTRAEEWXHOVJFV-UHFFFAOYSA-N 0.000 title 1
- 229960005117 olmesartan Drugs 0.000 title 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 11
- 150000001875 compounds Chemical class 0.000 abstract 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 3
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002051 C09CA08 - Olmesartan medoxomil Substances 0.000 abstract 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 abstract 2
- UQGKUQLKSCSZGY-UHFFFAOYSA-N Olmesartan medoxomil Chemical compound C=1C=C(C=2C(=CC=CC=2)C2=NNN=N2)C=CC=1CN1C(CCC)=NC(C(C)(C)O)=C1C(=O)OCC=1OC(=O)OC=1C UQGKUQLKSCSZGY-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000002425 crystallisation Methods 0.000 abstract 2
- 230000008025 crystallization Effects 0.000 abstract 2
- 238000010511 deprotection reaction Methods 0.000 abstract 2
- 229960001199 olmesartan medoxomil Drugs 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 238000000746 purification Methods 0.000 abstract 2
- 238000007127 saponification reaction Methods 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- -1 1-trityl-1H-tetrazol-5-yl Chemical group 0.000 abstract 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 abstract 1
- QCLFSYYUWPUWQR-UHFFFAOYSA-N 4-(chloromethyl)-5-methyl-1,3-dioxol-2-one Chemical compound CC=1OC(=O)OC=1CCl QCLFSYYUWPUWQR-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 abstract 1
- KZBJJAFGNMRRHN-UHFFFAOYSA-N ethyl 5-(2-hydroxypropan-2-yl)-2-propyl-1h-imidazole-4-carboxylate Chemical compound CCCC1=NC(C(=O)OCC)=C(C(C)(C)O)N1 KZBJJAFGNMRRHN-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES201031597 | 2010-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR083523A1 true AR083523A1 (es) | 2013-03-06 |
Family
ID=44913259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP110103905 AR083523A1 (es) | 2010-10-29 | 2011-10-21 | Procedimiento de obtencion del olmesartan medoxomilo |
Country Status (4)
| Country | Link |
|---|---|
| AR (1) | AR083523A1 (es) |
| TW (1) | TW201217363A (es) |
| UY (1) | UY33691A (es) |
| WO (1) | WO2012055994A1 (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103012382B (zh) * | 2012-12-05 | 2016-10-05 | 迪沙药业集团有限公司 | 一种奥美沙坦酯的制备方法 |
| CN103435602A (zh) * | 2013-07-31 | 2013-12-11 | 山东省医学科学院药物研究所 | 一种奥美沙坦酯的制备方法 |
| CN103724333B (zh) * | 2013-12-26 | 2016-06-08 | 南通康鑫药业有限公司 | 一种奥美沙坦酯的合成方法 |
| CN104592213A (zh) * | 2014-12-15 | 2015-05-06 | 山东新华制药股份有限公司 | 奥美沙坦酯中间体的制备方法 |
| CN107311990B (zh) * | 2017-07-25 | 2021-09-03 | 浙江华海致诚药业有限公司 | 一种奥美沙坦酯的制备方法 |
Family Cites Families (13)
| 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 |
| EP1706401A1 (en) | 2004-09-02 | 2006-10-04 | Teva Pharmaceutical Industries Ltd. | Preparation of olmesartan medoxomil |
| US20070054948A1 (en) | 2004-09-02 | 2007-03-08 | Lilach Hedvati | Purification of olmesartan medoxomil |
| KR20090102883A (ko) | 2004-09-02 | 2009-09-30 | 테바 파마슈티컬 인더스트리즈 리미티드 | 올메살탄 메독소밀의 정제 |
| CA2591694A1 (en) | 2004-12-30 | 2006-07-13 | Teva Pharmaceutical Industries Ltd. | 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 |
| EP1910343B1 (en) | 2005-07-29 | 2014-10-29 | Krka | Process for the preparation of olmesartan medoxomil |
| EP1816131A1 (en) | 2006-02-06 | 2007-08-08 | KRKA, tovarna zdravil, d.d., Novo mesto | 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 (cs) | 2005-10-27 | 2008-12-29 | Zentiva, A. S | Zpusob odstranování trifenylmethanové chránicí skupiny u prekurzoru antihypertenzních léciv |
| WO2007148344A2 (en) | 2006-06-19 | 2007-12-27 | Matrix Laboratories Limited | Process for the preparation of olmesartan medoxomil |
| AU2007306171B2 (en) | 2006-10-09 | 2013-02-21 | 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 |
-
2011
- 2011-10-21 AR ARP110103905 patent/AR083523A1/es unknown
- 2011-10-27 TW TW100139070A patent/TW201217363A/zh unknown
- 2011-10-27 UY UY33691A patent/UY33691A/es unknown
- 2011-10-28 WO PCT/EP2011/068963 patent/WO2012055994A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| TW201217363A (en) | 2012-05-01 |
| UY33691A (es) | 2012-04-30 |
| WO2012055994A1 (en) | 2012-05-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |