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Ipragliflozin

Ipragliflozin Struktur
761423-87-4
CAS-Nr.
761423-87-4
Englisch Name:
Ipragliflozin
Synonyma:
Suglat;CS-1580;Igliazine;Ipragliflozin;Iprag iflozin;Ipragliflozin-002;Ipragliflozin, >=98%;Ipragliflozin impuity;Ipragliflozin (Suglat);IpragliflozinL-Proline
CBNumber:
CB02589633
Summenformel:
C21H21FO5S
Molgewicht:
404.45
MOL-Datei:
761423-87-4.mol

Ipragliflozin Eigenschaften

Schmelzpunkt:
155-157°C
Siedepunkt:
628.8±55.0 °C(Predicted)
Dichte
1.452
storage temp. 
Refrigerator
L?slichkeit
DMSO (Slightly), Methanol (Slightly)
pka
13.27±0.70(Predicted)
Aggregatzustand
Solid
Farbe
White to Off-White

Sicherheit

Ipragliflozin Chemische Eigenschaften,Einsatz,Produktion Methoden

History

Ipragliflozin L-proline was approved in Japan in January 2014 for the treatment of type 2 diabetes. The drug was discovered by Astellas Pharma and co-developed and marketed with Kotobuki Pharmaceutical and Merck Sharp Dohme as Suglat?. Similar to empagliflozin (XIII), ipragliflozin L-proline is a sodium-glucose 1956 A. C. Flick et al. / Bioorg. Med. Chem. 24 (2016) 1937–1980 co-transporter-2 inhibitor which prevents glucose reabsorption by excreting excess glucose in the urine. Ipragliflozin exhibits remarkable selectivity over SLGT-1 (>250x).

Verwenden

Ipragliflozin is a potent and selective inhibitor of sodium-glucose cotransporter-2 (SGLT2) and can serve as a potential agent for the treatment of type 1 and type 2 diabetes.

Synthese

Commercial 5-bromo-2-fluorobenzaldehyde (123) was subjected to nucleophilic attack upon subjection to lithiated benzo[b]thiophene (124) to afford the dibenzylic alcohol 125 in 85% yield. This alcohol was then halogenated by means of thionyl chloride in acetonitrile to give 126, which was followed by treatment with sodium borohydride to give rise to 2-(5-bromo-2-fluorophenyl)- 1-benzothiophene (127), which was isolated by crystallization from 2-propanol and methanol in 81% yield across the two steps. Bromide 127 then underwent lithium¨Chalogen exchange prior to exposure to 2,3,4,6-tetrakis-O-(trimethylsilyl)- D-glucono-1,5-lactone (128) in toluene. Without workup, the resulting mixture was treated with a solution of methanol and HCl at 0 C to give a globally desilylated a-glucopyranoside intermediate. Subjection to acetic anhydride and 4-dimethylaminopyridine furnished tetra-O-acetyl ipragliflozin (129) in 75% yield for the 3 steps. Polyacetate 129 was then saponified using aqueous sodium hydroxide and the product was crystallized from methanol and water and subsequently treated with D-proline in ethanol to furnish the desired product ipragliflozin D-proline (XVI) in 68% yield.

Synthesis_761423-87-4

Mode of action

Ipragliflozin is a selective SGLT2 (sodium-glucose co-transporter 2) inhibitor discovered through research collaboration with Kotobuki Pharmaceutical Co., Ltd. SGLTs are membrane proteins that exist on the cell surface and transfer glucose into cells. SGLT2 is a subtype of the sodium-glucose co-transporters and plays a key role in the reuptake of glucose in the proximal tubule of the kidneys. Ipragliflozin reduces blood glucose levels by inhibiting the reuptake of glucose.

Ipragliflozin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Ipragliflozin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 199)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578
sales@hbmojin.com China 12834 58
Hebei Chuanghai Biotechnology Co,.LTD
+86-13131129325
sales1@chuanghaibio.com China 5889 58
Cangzhou Kangrui Pharma Tech Co. Ltd.,
+86-18632776803 +86-13833998158
cangzhoukangrui@126.com China 738 58
Shanghai Daken Advanced Materials Co.,Ltd
+86-371-66670886
info@dakenam.com China 18751 58
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
sales01@cooperate-pharm.com CHINA 1803 55
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21634 55
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 - 03@
sales03@shyrchem.com CHINA 738 60
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795
ivan@atkchemical.com China 32957 60
Anqing Chico Pharmaceutical Co., Ltd.
15380796838
chloewu@chicopharm.cn CHINA 340 58
career henan chemical co
+86-0371-86658258 +8613203830695
sales@coreychem.com China 29880 58

  • Ipragliflozin, >=98%
  • IpragliflozinL-Proline
  • Ipragliflozin (ASP1941)
  • Ipragliflozin impuity
  • (1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-glucitol
  • Ipragliflozin
  • ASP-1941/D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-, (1S)-
  • Ipragliflozin, (1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)Methyl]-4-fluorophenyl]-D-glucitol
  • (2S,3R,4R,5S,6R)-2-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
  • Ipragliflozin (Suglat)
  • IpragliflozinL-Proline int
  • Ipragliflozin-002
  • Ipragliflozin Impurity
  • CS-1580
  • D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylmethyl)-4-fluorophenyl]-, (1S)-
  • Suglat
  • Iprag iflozin
  • Igliazine
  • 761423-87-4
  • C21H21FO5S
  • Inhibitors
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