DR ANTHONY MELVIN CRASTO,WorldDrugTracker, helping millions, A 90 % paralysed man in action for you, I am suffering from transverse mylitis and bound to a wheel chair, With death on the horizon, nothing will not stop me except God................DR ANTHONY MELVIN CRASTO Ph.D ( ICT, Mumbai) , INDIA 25Yrs Exp. in the feld of Organic Chemistry,Working for GLENMARK GENERICS at Navi Mumbai, INDIA. Serving chemists around the world. Helping them with websites on Chemistry.Million hits on google, world acclamation from industry, academia, drug authorities for websites, blogs and educational contribution
Showing posts with label MITOGLITAZONE. Show all posts
Showing posts with label MITOGLITAZONE. Show all posts

Tuesday, 14 October 2014

MITOGLITAZONE


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
J. Med. Chem.199639 (26), pp 5053–5063
DOI: 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 6and 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 67, and 9roughly equivalent to 2. These data suggest that metabolites 67, 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.
……………………………….
1H NMR PREDICTION 
mitoglitazone
13C NMR PREDICTION
mitoglitazone
……………………………
WILL BE UPDATED…….keep watching this post