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MITOGLITAZONE

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Chemical structure for Mitoglitazone

MITOGLITAZONE

MSDC-0160; CAY 10415; 146062-49-9

5-[4-[2-(5-Ethylpyridin-2-yl)-2-oxoethoxy]benzyl]thiazolidine-2,4-dione

5-[[4-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

5-(4-(2-(5-cthylpyridin-2-yl)- 2-oxoethoxy)benzyl)-1,3 -thiazolidiiie-2,4-dione

Pfizer, INNOVATOR  phase 2

MSD-9
MSDC-0160
PNU-91325
U-91325

BACKGROUND

Thiazolidinedione analogs either prevent or ameliorate an insulin resistance state, which occurs genetically or is induced by dietary means. 5-(4-(2-(5-Ethylpyridin-2-yl)-2- oxoethoxy)benzyl)-l,3-thiazolidine-2,4-dione of Formula (I) (Mitoglitazonc) is an antidiabetic thiazolidinedione being evaluated for the treatment of non-insulin-dependent diabetes mellitus. Non-insulin-dependent diabetes mellitus (NIDDM) is a metabolic disease characterized by a reduction in the response of the peripheral target tissue to insulin and the inability of pancreatic insulin reserves to overcome the reduced response. Improvement of insulin sensitivity of the target tissue not only reduces the consequences of the disease but actually aids in the prevention of NIDDM.

The synthesis of Mitoglitazone has been reported (J. Med. Chem. , 1996, 39, 5053- 5063; Org. Pro. Res. & Dev. (OPRD), 2002, 6, 721-728 and U.S. PaL No. 5,441,971).

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http://www.google.com/patents/WO1992018501A1?cl=en


 

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Org. Proc. Res. Dev., 2002, 6 (5), pp 721–728
DOI: 10.1021/op025549s

http://pubs.acs.org/doi/abs/10.1021/op025549s

Abstract Image

An efficient six-step synthesis has been developed for the preparation of the thiazolidinedione analogue PNU-91325 (3) from the commercially available olefin 12. This process involves a novel epoxide ring opening with a deactivated phenol under phase-transfer conditions. Significant improvements were made in the oxidation of a secondary alcohol to the ketone and the 1,4-reduction of an enone from a previous process. Overall, this route allows for the preparation of PNU-91325 in 25% yield.

 

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US5,441,971

http://www.google.com/patents/US5441971

 

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J. Med. Chem., 1996, 39 (26), pp 5053–5063
DOI: 10.1021/jm9605694

http://pubs.acs.org/doi/abs/10.1021/jm9605694

Pioglitazone (5-(4-(2-(5-ethyl-2-pyridyl)ethoxy)benzyl)-2,4-thiazolidinedione, 2) is a prototypical antidiabetic thiazolidinedione that had been evaluated for possible clinical development. Metabolites 69 have been identified after dosing of rats and dogs. Ketone 10has not yet been identified as a metabolite but has been added to the list as a putative metabolite by analogy to alcohol 6 and ketone 7. We have developed improved syntheses of pioglitazone (2) metabolites 69 and the putative metabolite ketone 10. These entities have been compared in the KKAy mouse model of human type-II diabetes to pioglitazone (2). Ketone 10 has proven to be the most potent of these thiazolidinediones in this in vivo assay. When 610 were compared in vitro in the 3T3-L1 cell line to 2, for their ability to augment insulin-stimulated lipogenesis, 10 was again the most potent compound with 6, 7, and 9roughly equivalent to 2. These data suggest that metabolites 6, 7, and 9 are likely to contribute to the pharmacological activity of pioglitazone (2), as had been previously reported for ciglitazone (1).

5-((4-(2-(5-Ethyl-2-pyridyl)-1-oxoethoxy)phenyl)methyl)-2,4-thiazolidinedione (10). MITOGLITAZONE

free flowing white powdery solid

(mp 146−147 °C):

TLC (Merck; MeOH−CH2Cl2, 5:95, UV(+)) Rf = 0.21;

1H-NMR (CDCl3) δ 8.95 (brs, 1), 8.52 (d, J = 2.0 Hz, 1), 8.02 (d, J = 8.0 Hz, 1),

7.70 (dd, J = 8.0, 2.0 Hz, 1), 7.16 (d, J = 8.7 Hz, 2), 6.94 (d, J = 8.7 Hz, 2),

5.62 (s, 2), 4.49 (dd, J = 9.7, 3.8 Hz, 1), 3.47 (dd, J = 14.2, 3.8 Hz, 1),

3.08 (dd, J = 14.2, 9.7 Hz, 1), 2.76 (q, J = 7.6 Hz, 2), 1.31 (t, J = 7.6 Hz, 3);

 

13C-NMR (CDCl3) δ 194.7, 174.1, 170.4, 157.7, 149.7, 148.9, 144.7, 136.3, 130.3, 128.4, 121.9, 115.2, 70.5, 53.7, 37.8, 26.4, 15.0;

EI/MS (70 eV) 370 (M+, 19.4), 341 (6.9), 254 (20.6), 148 (base).

Anal. (C19H18N2O4S) C, H, N, S.

 

 

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1H NMR PREDICTION 

mitoglitazone

 

13C NMR PREDICTION

mitoglitazone

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WILL BE UPDATED…….keep watching this post

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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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