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 | |
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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 |
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Patent | Submitted | Granted |
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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
