AzilsartanMedoxomil Potassium
(5-methyl-2-oxo-l,3-dioxol-4-yl)methyl 2- ethoxy- 1 – { [2′-(5-oxo-4,5-dihydro- 1 ,2,4-oxadiazol-3-yl)biphenyl-4yl]methyl} – 1 H- benzimidazole-7-carboxylate monopotassium salt
NMR http://file.selleckchem.com/downloads/nmr/S305702-Azilsartan-Medoxomil-NMR-Selleck.pdf
AzilsartanMedoxomil Potassium is chemically named as (5-Methyl-2-oxo-1, 3-dioxol-4yl) methyl 2-ethoxy-1-{[2- (5-oxo-4, 5-dihydro-1, 2, 4-oxadiazol-3-yl) biphenyl-4-yl]methyl}- 1H-benzimidazole-7-carboxylatemonopotassium salt. Azilsartanmedoxomil is the prodrug of 2-ethoxy-1-([2′-(5-oxo4,5 – dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4- yl]methyl) 1H-benimidazole-7-carboxylic acid.It is a white crystalline powder insoluble in water, slightly soluble in solvents such as acetone, and acetonitrile, freely soluble in methanol, dimethylsulfoxide, and dimethylformamide, soluble in solvents such as acetic acid, and very slightly soluble in solvents tetrahydrofuran and 1-octanol.
The US Food and Drug Administration (FDA) has approved Edarbi tablet (AzilsartanMedoxomil Potassium) on February 25, 2011, to treat hypertension in adults. It is available in 80mg and 40 mg dosages, with the recommended dosage set at 80mg once in a day [1].
Angiotensin II hormone plays a vital role in activation of renin-angiotensinaldosterone systems well as in regulation of blood pressure, fluid-electrolyte balance, and also in pathophysiology of hypertension. Activation of type 1 angiotensin receptor which is a member of G protein coupled receptor efficiently controls the numerous effects of AII which are vasoconstriction, secretion of aldosterone and vasopressin and cellular proliferation. So blocking of AII receptor will also block receptor-1, and it will lead to termination of the whole course of action mentioned above;
so all blocker will be helpful in the management of cardiovascular and renal diseases as therapeutic agent.The active moiety of AMP is revealed by hydrolysis of the medoxomil ester and it converts into azilsartan which is an active angiotensin II receptor blocker and more effective in lowering blood pressure within 24 hours as compared to valsartan and olmesartan[2-5].There are several methods that are reported for preparation of azilsartan [6-15].
The presence of related substances in an active pharmaceutical ingredient (API) can have a significant impact on the quality and safety of the drug products. Therefore, it is necessary to study the impurity (related substance) profile of the API to be used in the manufacturing of the drug product. International Conference on Harmonization (ICH)guidelines recommends identifying and characterizing all related substancesthat are present at level less than 0.10% [16].
![2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid](http://pic6.molbase.net/molpic/ad/02/198350.png?246x193)
AZILSARTAN
| 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid | |
| CAS No.: | 147403-03-0 |
|---|---|
| Synonyms: |
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| Formula: | C25H20N4O5 |
| Exact Mass: | 456.14300 |
1H NMR
![2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid NMR spectra analysis, Chemical CAS NO. 147403-03-0 NMR spectral analysis, 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid H-NMR spectrum](http://pic11.molbase.net/nmr/nmr_image/2014-07-26/000/198/350/147403-03-0-1h.png)
13 C NMR
![2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid NMR spectra analysis, Chemical CAS NO. 147403-03-0 NMR spectral analysis, 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid C-NMR spectrum](http://pic11.molbase.net/nmr/nmr_image/2014-07-26/000/198/350/147403-03-0-13c.png)
AZILSARTAN MEDOXIMIL
![(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate](http://pic2.molbase.net/molpic/70/54/1535556.png?342x204)
| (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate | |
| CAS No.: | 863031-21-4 |
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| Synonyms: |
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| Formula: | C30H24N4O8 |
| Exact Mass: | 568.15900 |
![(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate NMR spectra analysis, Chemical CAS NO. 863031-21-4 NMR spectral analysis, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate H-NMR spectrum](http://pic11.molbase.net/nmr/nmr_image/2014-08-30/001/535/556/863031-21-4-1h.png)
![(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate NMR spectra analysis, Chemical CAS NO. 863031-21-4 NMR spectral analysis, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate C-NMR spectrum](http://pic11.molbase.net/nmr/nmr_image/2014-08-30/001/535/556/863031-21-4-13c.png)
| Cited Patent | Filing date | Publication date | Applicant | Title |
|---|---|---|---|---|
| WO2012107814A1 * | Jan 24, 2012 | Aug 16, 2012 | Jubilant Life Sciences Limited | An improved process for the preparation of azilsartan medoxomil |
| US5243054 * | Jun 25, 1992 | Sep 7, 1993 | Takeda Chemical Industries, Ltd. | Compound which is angiotensin ii antagonist |
| US20050187269 * | Jan 7, 2005 | Aug 25, 2005 | Takeda Pharmaceutical Company Limited | Benzimidazole derivative and use thereof |
| Citing Patent | Filing date | Publication date | Applicant | Title |
|---|---|---|---|---|
| WO2013186792A2 * | Jun 6, 2013 | Dec 19, 2013 | Msn Laboratories Limited | Process for the preparation of (5-methyl-2-oxo-l,3-dioxoi-4-vl)methvl 2- ethoxv-l-{[2′-(5-oxo-4,5-dihvdro-l,2,4-oxadiazol-3-vl)biphenyi-4-vl]methyl}- lh-benzimidazole-7-carboxyiate and its salts |
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[16] International Conference of Harmonization (ICH). Q3A(R) Related substance/Impurities in New Drug Substance, Feb. 2002.
Filed under: Uncategorized Tagged: AZILSARTAN
