BAZEDOXIFENE ACETATE Struktur

BAZEDOXIFENE ACETATE

Bezeichnung:BAZEDOXIFENE ACETATE

CAS-Nr198481-33-3

Englisch Name:BAZEDOXIFENE ACETATE

CBNumberCB71011079

SummenformelC32H38N2O5

Molgewicht530.67

MOL-Datei198481-33-3.mol

BAZEDOXIFENE ACETATE physikalisch-chemischer Eigenschaften

Schmelzpunkt	174-178°
storage temp.	-20°C
Löslichkeit	DMSO: soluble15mg/mL, clear
Aggregatzustand	powder
Farbe	white to beige
InChIKey	DGEPGJZKMFNSDD-UHFFFAOYSA-N
SMILES	C(=O)(O)C.C(C1C=CC(OCCN2CCCCCC2)=CC=1)N1C2C=CC(O)=CC=2C(C)=C1C1C=CC(O)=CC=1

Sicherheit

WGK Germany

Gefahreninformationscode (GHS)

BAZEDOXIFENE ACETATE Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Pale Beige Solid
Verwenden
Bazedoxifene acetate has been used to study its efficacy in inhibiting the interleukin-6 (IL-6)/IL-6R/glycoprotein 130 pathway and its effects on medulloblastoma cells.
Verwenden
Bazedoxifene Acetate is a nonsteroidal selective estrogen receptor modulator (SERM). Bazedoxifene Acetate is used as an antiosteoporotic.
Biologische Aktivität
bazedoxifene, a novel selective estrogen receptor modulator (serm), has been developed to have favorable effects on bone and the lipid profile while minimizing stimulation of uterine or breast tissues. two large phase iii
Biochem/physiol Actions
Bazedoxifene is a third generation nonsteroidal selective estrogen receptor modulator (SERM), used clinically to treat postmenopausal osteoporosis. Bazedoxifene binds to estrogen receptor-α with IC50 = 26 nM, similar to that of raloxifene, but lower affinity than 17-β estradiol. Bazedoxifene did not stimulate proliferation of MCF-7 cells, instead inhibited 17β -estradiol-induced proliferation with IC50 = 0.19 nM, exhibiting a desirable profile of agonist/antagonist activity.
Clinical Use
The selective estrogen receptor modulator bazedoxifene acetate was approved in Spain for the treatment of osteoporosis in postmenopausal women. The drug was discovered by Wyeth (now Pfizer) and licensed to Almirall. Clinical trials with bazedoxifene along with conjugated estrogens demonstrated significant improvement in bone mineral density and prevented bone loss in postmenopausal women without osteoporosis. It also reduces fracture risks among women with postmenopausal osteroporosis.
Synthese
Among many syntheses reported for this drug, the most recent process scale synthesis (multi-kg scale) is highlighted and involves the union of azepane ether 9 and indole 12. 4-Hydroxybenzyl alcohol (6) was converted in two steps to chloride 9 (the Scheme). The reaction of 6 with 2-chloroethyl azepane hydrochloride (7) in a biphasic mixture of sodium hydroxide and toluene in the presence of tetrabutylammonium bromide (TBAB) gave the desired intermediate alcohol 8 in 61% yield. Treatment of 8 with thionyl chloride (SOCl2) gave the requisite chloride 9 in 61% yield. The reaction of 2-bromopropiophenone (10) with an excess of 4-benzyloxy aniline hydrochloride (11) in the presence of triethylamine (TEA) in N,N-dimethylformamide (DMF) at elevated temperatures resulted in indole 12 in 65% yield. Alkylation of 12 with benzylchloride 9 in the presence of sodium hydride (NaH) afforded N-alkylated compound 13. The benzyl ether functionalities from compound 13 were removed via hydrogenolysis and subsequently subjected to acidic conditions, providing diol 14 as the hydrochloride salt in 91% yield. The hydrochloride was then exchanged for the acetate via free base preparation with 5% sodium bicarbonate or triethylamine, followed by treatment with acetic acid giving bazedoxifene acetate (II) in 73¨C85% yield.

BAZEDOXIFENE ACETATE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

198481-33-3, BAZEDOXIFENE ACETATE Verwandte Suche:

Send Inquriy