Alogliptin benzoate Basic information |
Indications and Usage Mechanisms of Action Adverse reactions |
Product Name: | Alogliptin benzoate |
Synonyms: | (R)-2-((6-(3-aMinopiperidin-1-yl)-3-Methyl-2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)Methyl)benzonitrile benzoate;Alogliptin benzoate 2-[[6-[(3R)-3-Amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]benzonitrile benzoate;Alogliptin(Alogliptin benzoate;2-[6-[3(R)-AMinopiperidin-1-yl]-3-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyriMidin-1-ylMethyl]benzonitrile benzoate Monobenzoate;Alogliptin API;ALOGLIPTIN(SYK-322) BENZOATE;(R)-2-((6-(3-Aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benz;2-[[6-[(3R)-3-aMino-1-piperidinyl]-3,4-dihydro-3-Methyl-2,4-dioxo-1(2H)-pyriMidinyl]Methyl]-Benzonitrile Monobenzoate |
CAS: | 850649-62-6 |
MF: | C25H27N5O4 |
MW: | 461.52 |
EINECS: | 691-730-4 |
Product Categories: | antidiabetic;Inhibitors;Final material;pharmaceutical intermediate;API |
Mol File: | 850649-62-6.mol |
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Alogliptin benzoate Chemical Properties |
Safety Information |
Alogliptin benzoate Usage And Synthesis |
Indications and Usage | Alogliptin (benzoic acid) is a type-2 diabetes medication, and it is a type of serine protease dipeptidyl peptidase IV (DPP-4) inhibitor developed by the Japanese company Takeda. Alogliptin, used alone or in combination with other blood sugar-lowering medication, is usually well-tolerated in type-2 diabetes patients. This medication has a low risk of hypoglycemia, with Alogliptin treatment groups ≤8.3% and placebo groups ≤10.5%, and shows no difference between young and elderly patients. In addition to effectively lowering blood sugar, this medicine also lowers the risks of hypoglycemia and weight increase, overcoming great obstacles in patient treatment and providing new hope for diabetes treatment. |
Mechanisms of Action | Alogliptin selectively inhibits DPP-4 to reduce the inactivation of glucagon-like peptide 1 (GLP-1) and increase the GLP-1 levels in the body, thus lowering blood sugar. Once blood sugar reaches normal levels, it will cease its sugar-lowering effects, thus effectively reducing the risks of hypoglycemia. Additionally, DPP-4 inhibitor also slows gastric emptying, increases the feeling of fullness, and controls appetite, thus helping patients control their weight. |
Adverse reactions | Common side effects of Alogliptin include nasopharyngitis, headaches, and upper respiratory tract infection. Most side effects are light to moderate and are unrelated to dosage. |
Uses | Treatment of type 2 diabetes. |
Definition | ChEBI: A benzoate salt obtained by combining equimolar amounts of alogliptin and benzoic acid. Used for treatment of type 2 diabetes. |
Clinical Use | Alogliptin benzoate is a dipeptidyl peptidase IV (DPPIV) inhibitor discovered by Takeda Pharmaceuticals and approved in Japan in 2010 for the treatment of type II diabetes mellitus. Alogliptin is an oral drug for once a day dosing to complement diet and exercise. Alogliptin is the most selective marketed DPPIV inhibition and has similar PK and PD properties compared to previous entries. The discovery, structure-activity relationship of related analogs, and synthesis of this compound have been recently published. |
Chemical Synthesis | The most convenient synthesis for scale-up will be highlighted from several published routes. Commercially available 2-cycanobenzyl amine 1 was reacted with methylisocyanate in DCM at ambient temperature to provide N-methyl urea 2 in 85% yield. Reaction of the urea 2 with dimethyl malonate in refluxing ethanol with sodium ethoxide as base gave the cyclized trione 3 in 78-85% yield. The trione 3 was then refluxed in neat POCl3 to provide the penultimate chloride crude 4 in 95% yield which was reacted with Boc-protected diamine 5 in the presense of potassium carbonate in DMF to furnish alogliptin I in 93-96% yield. Treatment of alogliptin with benzoic acid in ethanol at 60-70 °C followed by crystallization delivered the desired alogliptin benzoate (I).
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Not classified.
Pictogram(s) | No symbol. |
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Signal word | No signal word |
Hazard statement(s) | none |
Precautionary statement(s) | |
Prevention | none |
Response | none |
Storage | none |
Disposal | none |
no data available
Chemical name | Common names and synonyms | CAS number | EC number | Concentration |
---|---|---|---|---|
2-[[6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl] benzonitrile;benzoic acid | 2-[[6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl] benzonitrile;benzoic acid | 850649-62-6 | 691-730-4 | 100% |
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