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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

 

Pharmaceutical composition comprising a glitazone and a 4-oxobutanoic acid, and the use thereof for treating diabetes [US2005085489] 2005-04-21
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Medical devices to treat or inhibit restenosis [US2005149174] 2005-07-07
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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
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Pharmaceutical agent comprising insulin resistance improving agent [US2009124626] 2009-05-14
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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

 

 

 


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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 LIFE SCIENCES LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 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, Dr T.V. Radhakrishnan and Dr B. K. Kulkarni, 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 Open superstar 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 30 PLUS year tenure till date June 2021, Around 35 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, 90 Lakh plus views on dozen plus blogs, 233 countries, 7 continents, 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 33 lakh plus views on New Drug Approvals Blog in 233 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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