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AZILSARTAN SPECTRAL VISIT

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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

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:
  • UNII-F9NUX55P23;
  • 1H-Benzimidazole-7-carboxylic acid,1-[[2′-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1′-biphenyl]-4-yl]methyl]-2-ethoxy;
  • TAK 536;
  • azilsartan acid;
  • Azilsartan;
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

 

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

 

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

(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
Synonyms:
View More

  • Azilsartan Medoxomil;
  • Azilsartan (medoxomil);
  • Azilsartan;
  • azilsartan medoxomilo;
  • azilsartanum medoxomilum;
  • UNII-LL0G25K7I2;
  • (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-1-((2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate;
  • [14C]-Azilsartan medoxomil;
  • Edarbi;
  • TAK 491;
  • Azilsartan kamedoxomil;
  • (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester of 1-[[2′-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1′-biphenyl]-4-yl]methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic acid;
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

(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

 

 

 

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

REFERENCES [1] M. Gasparo, K. J. Catt, T. Inagami, J.W. Wright, T. Unger, Pharmacol. Rev.2000, 52, 415

[2] W.B. White, M.A. Weber, D. Sica, G.L. Bakris,A. Perez,C. Cao, S. Kupfer, Hypertension.2011, 57, 413.

[3] G.L.Bakris, D.Sica, M.Weber, W.B. White,A. Roberts,A. Perez, C. Cao, S. J. Kupfer, Clin. Hypertens.2011, 13, 81.

[4] D. Sica, W.B. White, M.A. Weber, G.L. Bakris, A. Perez,C. Cao,A. Handley, S. Kupfer, J. Clin. Hypertens. 2011, 13, 467.

[5] H. Rakugi, K. Enya, K. Sugiura, Y. Ikeda, Hypertens. Res.2012, 35, 552.

[6] Y. Kohara, E. Imamiya, K. Kubo, T. Wada, Y. Inada, T. Naka, Bioorg. Med. Chem. Lett.1995, 5, 1903.

[7] T. Naka,Y. Inada, U.S. Patent 5583141 (1996) [8] T. Naka, Y. Inada, Eur Pat. Appl. EP 0520423, (1992)

[9] Y. Kohara, K. Kubo,E. Imamiya, T. Wada, Y. Inada, T. Naka, J. Med. Chem.1996, 39, 5228.

[10] T. Kuroita, H. Sakamoto,M.Ojima, U.S. Pat. Appl. 0187269 (2005) [11] T. Kuroita, H. Sakamoto, M. Ojima, U.S. Pat. Appl. 7157584 (2007) [12] S. Radl, J. Cerny,J. Stach, Z. Gablíkova, Org. Process Res. Dev.2013, 17, 77

[13] A. Agarwal, D. Bansal, A.S. Choudhary, S.K. Dubey, H. Mishra, D. Vir, WO 2012107814 A8 (2012)

[14] S.D. Dwivedi, K.K. Singh, J.T. Gajera, US 20140113942 A1, (2014)

[15] D. Bansal,H. Mishra,S.K. Dubey, A.S. Choudhary, D. Vir, A. Agarwal, A. Daz, US 20130317230 A1 (2013)

[16] International Conference of Harmonization (ICH). Q3A(R) Related substance/Impurities in New Drug Substance, Feb. 2002.


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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 29 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 29 year tenure till date Aug 2016, Around 30 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 25 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 13 lakh plus views on New Drug Approvals Blog in 212 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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