Sergliflozin

 Sergliflozin

408504-26-7 cas no

ethyl [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-[(4-methoxyphenyl)methyl]phenoxy]oxan-2-yl]methyl carbonate
 
2-(4-methoxybenzyl)phenyl 6-O-ethoxycarbonyl-beta-D-glucopyranoside
ethyl [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-[(4-methoxyphenyl)methyl]phenoxy]tetrahydropyran-2-yl]methyl carbonate
ethyl [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{2-[(4-methoxyphenyl)methyl]phenoxy}oxan-2-yl]methyl carbonate

PHASE 2..........TYPE 3 DIABETES AND OBESITY
A SGLT-2 inhibitor potentially for the treatment of type 2 diabetes and obesity.

  

GW-869682; GW-869682X; KGT-1251

 MW 448.4, C23H28O9

KISSEI INNOVATOR
GSK DEVELOPER

Sergliflozin Etabonate is a benzylphenol glucoside and selective sodium-glucose co-transporter subtype 2 (SGLT2) inhibitor with antihyperglycemic activity. Its prodrug form, sergliflozin etabonate, is orally available and is converted to sergiflozin upon absorption.
 

Sergliflozin etabonate (INN/USAN,^[1][2] codenamed GW869682X) is an investigational anti-diabetic drug being developed by GlaxoSmithKline. It did not undergo further development after phase II.

Sergliflozin inhibits subtype 2 of the sodium-glucose transport proteins (SGLT2), which is responsible for at least 90% of the glucose reabsorption in the kidney. Blocking this transporter causes blood glucose to be eliminated through the urine.^[3][4]

Chemistry

Etabonate refers to the ethyl carbonate group. The remaining structure, which is the active substance, is called sergliflozin.

Sergliflozin

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Design, Syntheses, and SAR Studies of Carbocyclic Analogues of Sergliflozin as Potent SodiumDependent Glucose Cotransporter 2 In

 Sergliflozin Etabonate is a benzylphenol glucoside and selective sodium-glucose co-transporter subtype 2 (SGLT2) inhibitor with antihyperglycemic activity. Its prodrug form, sergliflozin etabonate, is orally available and is converted to sergiflozin upon absorption.



 

sergliflozin and prodrugs of sergliflozin, in particular sergliflozin etabonate, including hydrates and solvates thereof, and crystalline forms thereof. Methods for its manufacture are described in the patent applications EP 1344780 and EP 1489089 for example.

The compounds are described in EP 1 329 456 A1 and a crystalline form ofSergliflozin etabonate is described in EP 1 489 089 A1.

1.  World Health Organization (2008). "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 59". WHO Drug Information 22 (1): 66.
2. Jump up "Statement on a nonproprietary name adopted by the USAN council: Sergliflozin etabonate". American Medical Association. Retrieved 2008-08-10.
3. Jump up Katsuno K, Fujimori Y, Takemura Y, et al. (January 2007). "Sergliflozin, a novel selective inhibitor of low-affinity sodium glucose cotransporter (SGLT2), validates the critical role of SGLT2 in renal glucose reabsorption and modulates plasma glucose level". J Pharmacol Exp Ther 320 (1): 323–30.doi:10.1124/jpet.106.110296. PMID 17050778.
4. Jump up Prous Science: Molecule of the Month November 2007

Patent	Submitted	Granted
Progression Inhibitor For Disease Attributed To Abnormal Accumulation Of Liver Fat [US2008045466]	2008-02-21
NOVEL SUBSTITUTED TETRAHYDRONAPHTHALENES, PROCESS FOR THE PREPARATION THEREOF AND THE USE THEREOF AS MEDICAMENTS [US2010249097]	2010-09-30
(CARBOXYLALKYLENEPHENYL)PHENYLOXAMIDES, METHOD FOR THE PRODUCTION THEREOF AND USE OF SAME AS A MEDICAMENT [US2010261645]	2010-10-14
(CYCLOPROPYLPHENYL)PHENYLOXAMIDES, METHOD FOR THE PRODUCTION THEREOF, AND USE OF SAME AS A MEDICAMENT [US8148375]	2010-10-14	2012-04-03
Crystals of glucopyranosyloxybenzyl benzene derivative [US7371730]	2005-06-02	2008-05-13
CERTAIN CRYSTALLINE DIPHENYLAZETIDINONE HYDRATES, PHARMACEUTICAL COMPOSITIONS THEREOF AND METHODS FOR THEIR USE [US8003636]	2009-08-13	2011-08-23
NOVEL DIPHENYLAZETIDINONE SUBSTITUTED BY PIPERAZINE-1-SULFONIC ACID AND HAVING IMPROVED PHARMACOLOGICAL PROPERTIES [US2009264402]	2009-10-22
Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, process for preparing them, medicaments comprising these compounds, and their use [US7759366]	2009-08-27	2010-07-20
Glucopyranosyloxybenzylbenzene derivatives and medicinal compositions containing the same [US2005065098]	2005-03-24
Glucopyranosyloxybenzylbenzene derivatives and medicinal compositions containing the same [US6872706]	2004-01-29	2005-03-29

Patent	Submitted	Granted
PROGRESSION INHIBITOR FOR DISEASE ATTRIBUTED TO ABNORMAL ACCUMULATION OF LIVER FAT [US2009286751]	2009-11-19
THERAPEUTIC USES OF SGLT2 INHIBITORS [US2011077212]	2011-03-31
PHARMACEUTICAL COMPOSITION COMPRISING A SGLT2 INHIBITOR IN COMBINATION WITH A DPP-IV INHIBITOR [US2011098240]	2011-04-28
Substituted imidazoline-2,4-diones, process for preparation thereof, medicaments comprising these compounds and use thereof [US2011112097]	2011-05-12
Heterocycle-substituted imidazolidine-2,4-diones, process for preparation thereof, medicaments comprising them and use thereof [US2011046105]	2011-02-24
Arylchalcogenoarylalkyl-substituted imidazolidine-2,4-diones, process for preparation thereof, medicaments comprising these compounds and use thereof [US2011046185]	2011-02-24
Arylchalcogenoarylalkyl-substituted imidazolidine-2,4-diones, process for preparation thereof, medicaments comprising these compounds and use thereof [US2011053947]	2011-03-03
Novel aromatic fluoroglycoside derivatives, pharmaceuticals comprising said compounds and the use thereof [US2011059910]	2011-03-10
Novel phenyl-substituted imidazolidines, process for preparation thereof, medicaments comprising said compounds and use thereof [US2011178134]	2011-07-21
HETEROCYCLIC COMPOUNDS, PROCESSES FOR THEIR PREPARATION, MEDICAMENTS COMPRISING THESE COMPOUNDS, AND THE USE THEREOF [US2011183998]	2011-07-28

Sergliflozin etabonate

Systematic (IUPAC) name
2-(4-methoxybenzyl)phenyl 6-O-(ethoxycarbonyl)-β-D-glucopyranoside
Clinical data
Routes of administration	Oral
Identifiers
CAS Number	408504-26-7
ATC code	None
PubChem	CID: 9824918
IUPHAR/BPS	4587
ChemSpider	21234810
ChEMBL	CHEMBL450044
Chemical data
Formula	C23H28O9
Molecular mass	448.463 g/mol

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CCOC(=O)OCC1C(C(C(C(O1)OC2=CC=CC=C2CC3=CC=C(C=C3)OC)O)O)O
CCOC(=O)OCC1C(C(C(C(O1)Oc2ccccc2Cc3ccc(cc3)OC)O)O)O