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NETOGLITAZONE

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Figure US08017633-20110913-C00025

NETOGLITAZONE, isaglitazone

161600-01-7

 

  1. 5-((6-((2-fluorophenyl)methoxy)-2-naphthalenyl)methyl)-2,4-thiazolidinedione
  2. MCC 555
  3. MCC-555
  4. netoglitazone
  5. RWJ-241947

Netoglitazone (MCC-555) is a hypoglycemic agent.

Synthesis

Netoglitazone.png

 

Netoglitazone.png

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.

Netoglitazone
Netoglitazone.svg
Systematic (IUPAC) name
5-[(6-[(2-fluorophenyl)methoxy]naphthalen-2-yl)methyl]-1,3-thiazolidine-2,4-dione
Clinical data
Legal status
  • Uncontrolled
Identifiers
CAS number 161600-01-7 Yes
ATC code ?
PubChem CID 204109
UNII QOV2JZ647A Yes
KEGG D05150 Yes
Chemical data
Formula C21H16FNO3S 
Mol. mass 381.420 g/mol

 

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Filed under: DIABETES, Uncategorized Tagged: NETOGLITAZONE

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