NETOGLITAZONE, isaglitazone
- 5-((6-((2-fluorophenyl)methoxy)-2-naphthalenyl)methyl)-2,4-thiazolidinedione
- MCC 555
- MCC-555
- netoglitazone
- RWJ-241947
Netoglitazone (MCC-555) is a hypoglycemic agent.
Synthesis
US 5594016
http://www.google.co.in/patents/US5594016
Reaction of aldehyde (III) with 2-fluorobenzyl alcohol (VIII) by means of triphenylphosphine and diethyl azodicarboxylate (DEAD) in THF furnishes 6-(2-fluorobenzyloxy)naphthalene-2-carbaldehyde (IX) , which is then reduced with NaBH4 in ethanol/THF to give the naphthalenemethanol derivative (X). Halogenation of (X) by means of iodide, triphenylphosphine and imidazole in THF yields the naphthylmethyl iodide derivative (XI), which is finally condensed with thiazolidine-2,4-dione (IV) by means of HMPA and butyl lithium in THF.
Ueno, H.; Oe, T.; Suehiro, I.; Nakamura, F. (Mitsubishi Chemical Corp.); Naphthalene derivs.. EP 0604983; JP 1994247945; US 5594016 .
http://www.google.co.in/patents/EP0604983B1?cl=en
References
Sorbera, L.A.; Castañer, J.; Del Fresno, M.; Silvestre, J. (2002). “Netoglitazone”. Drugs of the Future 27 (2): 132.doi:10.1358/dof.2002.027.02.657482.
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| Systematic (IUPAC) name | |
|---|---|
| 5-[(6-[(2-fluorophenyl)methoxy]naphthalen-2-yl)methyl]-1,3-thiazolidine-2,4-dione | |
| Clinical data | |
| Legal status |
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| Identifiers | |
| CAS number | 161600-01-7  |
| ATC code | ? |
| PubChem | CID 204109 |
| UNII | QOV2JZ647A |
| KEGG | D05150 |
| Chemical data | |
| Formula | C21H16FNO3S |
| Mol. mass | 381.420 g/mol |
| Pharmaceutical composition comprising a glitazone and a 4-oxobutanoic acid, and the use thereof for treating diabetes [US2005085489] | 2005-04-21 | |
| Compositions of a cyclooxygenase-2 selective inhibitor and a peroxisome proliferator activated receptor agonist for the treatment of ischemic mediated central nervous system disorders [US2005107387] | 2005-05-19 | |
| Pharmaceutical composition comprising an ACAT inhibitor and an insulin resistance reducing agent [US2005119314] | 2005-06-02 | |
| Medical devices to treat or inhibit restenosis [US2005149174] | 2005-07-07 | |
| Medicinal compositions containing diuretic and insulin resistance-improving agent [US2005288339] | 2005-12-29 | |
| Crystals of 5-[{6-(2-fluorobenzyl)oxy-2-naphthyl}methyl]-2,4-thiazolidinedione [US2006149075] | 2006-07-06 | |
| Concomitant drug as therapeutic agent for inflammatory bowel disease [US2006177444] | 2006-08-10 | |
| Combination of FBPase inhibitors and insulin sensitizers for the treatment of diabetes [US2004167178] | 2004-08-26 | |
| Crystals of 5-[{6-(2-fluorobenzyl)oxy-2-naphthyl}methyl]-2,4-thiazolidinedione [US2003158241] | 2003-08-21 | |
| Pharmacological method for treatment of neuropathic pain [US2007249561] | 2007-10-25 |
| Patent | Submitted | Granted |
|---|---|---|
| Medicinal composition containing diabetes remedy [US7943584] | 2008-02-14 | 2011-05-17 |
| Medicinal compositions containing diuretic and insulin resistance-improving agent [US7199139] | 2004-03-18 | 2007-04-03 |
| Crystals of 5-[{6-(2-fluorobenzyl)oxy-2-naphthyl}methyl]-2,4-thiazolidinedione [US6541493] | 2003-04-01 | |
| Combination of FBPase inhibitors and insulin sensitizers for the treatment of diabetes [US6756360] | 2004-06-29 | |
| Roflumilast for the Treatment of Diabetes Mellitus [US8017633] | 2008-09-04 | 2011-09-13 |
| Combination of FBPase Inhibitors and Insulin Sensitizers for the Treatment of Diabetes [US2008004226] | 2008-01-03 | |
| Pharmaceutical Composition Comprising Ppar Regulator [US2008153882] | 2008-06-26 | |
| Pharmaceutical combination comprising vitamin k [US2009137614] | 2009-05-28 | |
| Pharmaceutical Composition Containing PPARgamma Agonist [US2009137626] | 2009-05-28 | |
| Pharmaceutical agent comprising insulin resistance improving agent [US2009124626] | 2009-05-14 | |
| ROFLUMILAST FOR THE TREATMENT OF DIABETES MELLITUS [US2011269750] | 2011-11-03 | |
| Combination treatment for diabetes mellitus [US2010179131] | 2010-07-15 | |
| Therapeutic agent for diabetes containing insulin resistance improving agent [US2007049515] | 2007-03-01 | |
| PHARMACEUTICAL COMBINATION COMPRISING VITAMIN K [US2011028499] | 2011-02-03 | |
| RESPIRATORY DISEASE TREATMENT [US8236786] | 2011-03-03 | 2012-08-07 |
Filed under: DIABETES, Uncategorized Tagged: NETOGLITAZONE
