Minodronic Acid

Bezeichnung:Minodronic Acid

CAS-Nr155648-60-5

Englisch Name:Minodronic Acid

CBNumberCB82521286

SummenformelC9H14N2O8P2

Molgewicht340.163582

MOL-Datei155648-60-5.mol

Minodronic Acid physikalisch-chemischer Eigenschaften

storage temp.	2-8°C
Wasserlöslichkeit	Insoluble in water
Aggregatzustand	powder to crystal
Farbe	White to Light yellow to Light red
InChI	InChI=1S/C9H12N2O7P2.H2O/c12-9(19(13,14)15,20(16,17)18)5-7-6-10-8-3-1-2-4-11(7)8;/h1-4,6,12H,5H2,(H2,13,14,15)(H2,16,17,18);1H2
InChIKey	GPAPAOGRNKUFGH-UHFFFAOYSA-N
SMILES	C(P(O)(O)=O)(O)(P(O)(O)=O)CC1N2C(=NC=1)C=CC=C2.[H]O[H]

Sicherheit

RIDADR	2811
RTECS-Nr.	SZ8562470
HS Code	2933.99.8290
HazardClass	6.1
PackingGroup	III

Gefahreninformationscode (GHS)

Minodronic Acid Chemische Eigenschaften,Einsatz,Produktion Methoden

Mechanism of action
Third-generation bisphosphonates, including minodronic acid hydrate, contain an amino group in the imidazole ring and are even more powerful inhibitors of bone resorption. With regard to inhibition of bone resorption, minodronic acid hydrate is 1000 times more effective than etidronate and 10–100 times more effective than alendronic acid. Following administration, minodronic acid hydrate specifically accumulates in the bone. It is then separated from the bone by acid released by osteoclasts during the bone resorption process and selectively taken up by osteoclasts. Conventional bisphosphonates were believed to inhibit bone resorption through the induction of osteoclast apoptosis after being taken up by these cells[1].
Clinical Use
The bone resorption inhibitor minodronic acid hydrate was approved and introduced last year in Japan, bringing the total number of bis-phosphonates marketed for this indication to seven. There are an estimated 10 million current and potential osteoporosis sufferers in Japan, a number that is expected to continue growing due to the country’s aging population. Minodronic acid is the first drug to show a significant effect in preventing bone fractures as compared to placebo in a Japanese patient population. Minodronic acid was co-developed by Astellas and Ono, who are marketing the drug as Bonoteo and Recalbon, respectively.
Synthese
Several syntheses of minodronic acid have been reported,a scalable preparation is described in the scheme. Commercially available acid chloride 71 was first reduced with lithium tritertbutoxy aluminum hydride to the aldehyde 72 at 80??C in 61% yield. Next, reaction of aldehyde 72 with TMSCl and triethylamine generated the corresponding silyl enol ether, which was then treated with bromine to give a-bromoaldehyde 73 in 62% yield. Condensation with 2-amino pyridine furnished imidazopyridine 74, which was hydrolyzed with HCl to acid 75 in 58% yield. Reaction with H3PO3 at 120??C to provide minodronic acid hydrate (XII) in 53% yield.
Einzelnachweise
[1] Shinji Tanishima, Yasuo Morio. “A review of minodronic acid hydrate for the treatment of osteoporosis.” Clinical Interventions in Aging 8 (2013): 185–9.

Minodronic Acid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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