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Polymorphs of alogliptin benzoate

A benzoic acid, form of technology, applied in the field of new form of alogliptin benzoate, can solve unmet problems

Inactive Publication Date: 2013-04-24
MAPI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] There is still an unmet need for additional solid state forms of alogliptin or salts thereof having good physicochemical properties, desirable bioavailability and favorable pharmaceutical parameters

Method used

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  • Polymorphs of alogliptin benzoate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Embodiment 1: General preparation method of alogliptin benzoate polymorph

[0075] 1. Reagents

[0076] Acetonitrile, HPLC grade, Sigma, lot number MKBC1316

[0077] Ethanol, AR, SCRC, lot number T10000418

[0078] DMSO, HPLC grade, Sigma, lot number 05737BH

[0079] Dichloromethane, AR, SCRC, Lot No. 80047318

[0080] Methanol, AR, SCRC, Lot No. 80080418

[0081] Ethanol Acetate (Ethanol Acetate), AR, Yixing Secondary Chemical Company (YixingSecondary Chemical Company), batch number 090607

[0082] MIBK, AR, SCRC, batch number T20080411

[0083] Isopropanol, AR, Sinopharm Chemical Reagent Co.Ltd, batch number T20090813

[0084] Acetone, AR, Sinopharm Chemical Reagent Co.Ltd, batch number 10000418

[0085] Toluene, AR, SCRC, batch number T20090603

[0086] tert-Butyl methyl ether, HPLC grade, Fluka, lot number 1359496

[0087]THF, AR, Yixing Secondary Chemical Company (Yixing Secondary Chemical), batch number 090901

[0088] n-Butanol, AR, SCRC, batch number...

Embodiment 2

[0138] Example 2: Amorphous Alogliptin Benzoate Form I (Method I)

[0139] Implement general method I. Thus, the alogliptin API was heated to 200° C., followed by rapid cooling (quenching) or slow cooling. This new polymorphic form exhibits an amorphous powder ( figure 1 , panels A and B) characteristic broad X-ray diffraction peaks between about 10 and about 35 [2θ°]. The amorphous phase is stable even after heating to 300°C. figure 2 A characteristic DSC curve is shown. The DSC curve of the amorphous alogliptin benzoate Form I of the present invention is significantly different from the DSC curve of the amorphous alogliptin benzoate disclosed in WO2007 / 035372. For example, the amorphous alogliptin benzoate form I of the present invention exhibits a relatively smooth DSC curve with no exothermic peak at 132°C and no endothermic peak at 183°C, unlike the amorphous alogliptin benzoate in WO 2007 / 035372 Form 1 is the opposite. According to WO 2007 / 035372, recrystallizat...

Embodiment 3

[0141] Example 3: Amorphous Alogliptin Benzoate Form II (Method II)

[0142] Implement general method II. Thus, alogliptin API was dissolved in EtOH at room temperature until a saturated solution of alogliptin was obtained. The solvent was then removed by rotary evaporation below 50 °C. This new polymorphic form exhibits an amorphous powder ( Figure 7 , Panel C) characteristic broad X-ray diffraction peaks between about 10 and about 35 [2θ°]. Figure 8 A characteristic DSC curve is shown with an exothermic peak at about 128°C followed by an endothermic peak at 182°C. After DSC measurement, this amorphous form crystallized into alogliptin API. Amorphous Form II of the present invention is further characterized by modulating the DSC in order to determine its glass transition temperature ( Figure 9 ). The glass transition temperature is between about 68°C and about 73°C (variation between batches is mainly due to the effect of residual solvent). Figure 10 Characterist...

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Abstract

The present invention provides new amorphous forms of alogliptin benzoate, pharmaceutical compositions comprising same, methods for their preparation and use thereof in treating conditions mediated by DPP-IV, in particular, type 2 diabetes.

Description

technical field [0001] The present invention relates to a new form of alogliptin benzoate, a pharmaceutical composition containing the new form of alogliptin benzoate and its application in the treatment of type 2 diabetes. Background technique [0002] Alogliptin is a selective serine protease dipeptidyl peptidase IV (DPP IV) inhibitor, through the control of glucagon-like peptide 1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP, also known as It is the incretin activity of gastric inhibitory peptide), which can effectively maintain blood sugar homeostasis (glucose homeostasis, glucose homeostasis). Therefore, it has been proposed as a powerful drug in the treatment of type 2 diabetes. The benzoate salt of alogliptin (SYR-322) has shown encouraging antidiabetic efficacy. [0003] Alogliptin is chemically named 2-[6-[3(R)-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro Pyrimidin-1-ylmethyl]benzonitrile, represented by the following chemical struc...

Claims

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Application Information

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IPC IPC(8): A61K31/513C07D213/84
CPCA61K31/513C07D401/04A61P3/10
Inventor 埃胡德·马罗姆塞·鲁比诺夫
Owner MAPI PHARMA
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