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Medicinal salts of saxagliptin and preparation methods of medicinal salts

A technology of medicinal salt and maleate, which is applied in the field of pharmacy, can solve the problems of complex preparation process, difficulty in realizing industrial production, and difficulty in quality control

Inactive Publication Date: 2011-06-08
廖国超
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Because the conventional oral preparations of saxagliptin hydrochloride are difficult to achieve industrial production, the quality is difficult to control, the preparation process is complicated and the production cost is high, which seriously limits its clinical large-scale application.

Method used

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  • Medicinal salts of saxagliptin and preparation methods of medicinal salts
  • Medicinal salts of saxagliptin and preparation methods of medicinal salts
  • Medicinal salts of saxagliptin and preparation methods of medicinal salts

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] The preparation of embodiment 1 saxagliptin mesylate

[0082] Saxagliptin (0.50g, 1.59mmol) was dissolved in 8ml ethanol solution, stirred, heated to 40°C, slowly added 2ml ethanol containing methanesulfonic acid (0.15g, 1.59mmol), cooled to room temperature after addition, Add 16ml of diethyl ether, continue stirring for 1 hour, cool down to 0°C and stir overnight, filter, and vacuum-dry the filter cake at 30°C to obtain 0.43g of light yellow powdery solid, yield 66.2%.

[0083] 1 HNMR (CD 3 OD), δ(ppm): 0.94(m, 1H), 1.10(m, 1H), 1.52-1.88(m, 12H), 2.02(m, 1H), 2.27(s, 2H), 2.34(m, 1H ), 2.60(m, 1H), 2.89(s, 3H), 3.93(m, 1H), 4.28(s, 1H), 5.20(m, 1H).

[0084] ESI-MS m / z: 316.2[M+H] + .

[0085] Elemental analysis (C 19 h 29 N 3 o 5 S·H 2 O): Tested value (%): C, 53.02; H, 7.35; N, 9.63 (calculated value (%): C, 53.13; H, 7.27; N, 9.78).

Embodiment 2

[0086] The preparation of embodiment 2 saxagliptin maleate (1: 1)

[0087] Saxagliptin (3.50 g, 11.1 mmol) was dissolved in 25 ml of ethyl acetate solution, stirred, heated to 45° C., slowly added in maleic acid (1.29 g, 11.1 mmol) in batches, and stirred for 10 minutes after the addition was completed. Cool down to room temperature, slowly add 25ml of cyclohexane, continue to stir for 1 hour, cool down to 0°C and stir overnight, filter, and vacuum-dry the filter cake at 30°C to obtain 3.46g of white powdery solid with a yield of 72.2%.

[0088] 1 HNMR (CD 3 OD), δ(ppm): 0.95(m, 1H), 1.12(m, 1H), 1.54-1.88(m, 12H), 2.01(m, 1H), 2.27(s, 2H), 2.34(m, 1H ), 2.61 (m, 1H), 3.93 (m, 1H), 4.28 (s, 1H), 5.19 (m, 1H), 6.28 (s, 2H).

[0089] ESI-MS m / z: 316.2[M+H] + .

[0090] Elemental analysis (C 22 h 29 N 3 o 6 ): Tested value (%): C, 61.09; H, 6.81; N, 9.48 (calculated value (%): C, 61.24; H, 6.77; N, 9.74).

Embodiment 3

[0091] The preparation of embodiment 3 saxagliptin maleate (2: 1)

[0092] Saxagliptin (0.50g, 1.59mmol) was dissolved in 5ml of ethyl acetate solution, stirred, heated to 45°C, slowly added in maleic acid (0.09g, 0.78mmol) in batches, and stirred for 10 minutes after the addition was complete. Cool down to room temperature, slowly add 5ml of cyclohexane, continue to stir for 1 hour, cool down to 0°C and stir overnight, filter, and vacuum-dry the filter cake at 30°C to obtain 0.38g of white powdery solid with a yield of 64.4%.

[0093] 1 HNMR (CD 3 OD), δ(ppm): 0.95(m, 2H), 1.10(m, 2H), 1.52-1.86(m, 24H), 2.00(m, 2H), 2.28(s, 4H), 2.34(m, 2H ), 2.61 (m, 2H), 3.93 (m, 2H), 4.28 (s, 2H), 5.19 (m, 2H), 6.30 (s, 2H).

[0094] ESI-MS m / z: 316.2[M+H] + .

[0095] Elemental analysis (C 40 h 54 N 6 o 8 ): Tested value (%): C, 64.47; H, 7.35; N, 11.09 (calculated value (%): C, 64.32; H, 7.29; N, 11.25).

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Abstract

The invention provides medicinal salts of saxagliptin, and particularly relates to mesylate, meleate, malate, succinate and citrate as well as preparation methods of the medicinal salts. The medicinal salts have the advantage of good stability, and are not easy to degrade. Preparations with controllable quality and low cost, which are suitable for industrial production, are prepared from the medicinal salts and pharmaceutically acceptable carriers through a conventional preparation technology. The medicinal salts can be used for treating and / or preventing diabetes mellitus.

Description

1. Technical field [0001] The invention belongs to the field of pharmacy, and more specifically relates to a new pharmaceutically acceptable salt of dipeptidyl-peptidase-IV (DPP-IV) inhibitor saxagliptin, a preparation method thereof and an application in treating diabetes. 2. Background technology [0002] Diabetes is a multi-cause metabolic disease that seriously endangers health. About 5% of people in the world suffer from this chronic life-long disease. Disability and high mortality rate seriously affect the physical and mental health of patients. With the change of people's lifestyle and the acceleration of the aging process in our country, the prevalence of diabetes is rising rapidly. Its incidence has risen from 0.67% in 1979 to 5.6% in recent years, and the total number of patients exceeds 70 million. After cardiovascular and cerebrovascular diseases and tumors, another important chronic disease that seriously endangers people's health brings a heavy burden to indiv...

Claims

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Application Information

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IPC IPC(8): C07D209/52A61K31/403A61P3/10
Inventor 廖国超曲昌海谢寅省
Owner 廖国超
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