Metformin r-(+) lipoate as an antidiabetic agent for control of diabetic hyperglycemia and diabetic complications

一种二甲双胍、硫辛酸盐的技术，应用在作为抗糖尿病药用于控制糖尿病高血糖症和糖尿病并发症的二甲双胍R－(+)硫辛酸盐领域

Inactive Publication Date: 2009-09-02
INDIGENE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many diabetics develop resistance to metformin

Method used

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  • Metformin r-(+) lipoate as an antidiabetic agent for control of diabetic hyperglycemia and diabetic complications
  • Metformin r-(+) lipoate as an antidiabetic agent for control of diabetic hyperglycemia and diabetic complications
  • Metformin r-(+) lipoate as an antidiabetic agent for control of diabetic hyperglycemia and diabetic complications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1: Preparation of metformin R-(+)-lipoate

[0066] Step 1.1 Preparation of metformin free base:

[0067] Amberlyst A26(OH) ion exchange resin (60 g) was washed 3 times with deionized water and 2 times with 2% (v / v) deionized water in methanol. The resin was packed into a 2.5 cm diameter glass column (packed column height 20 cm). The column was further rinsed with 300 mL of 2% (v / v) deionized water in methanol. Metformin hydrochloride (6.5 g) was dissolved in 180 mL of 2% (v / v) deionized water in methanol and eluted through an ion exchange column. The column was further washed with 200 mL of 2% (v / v) deionized water in methanol. The combined eluates were concentrated under reduced pressure to give a white powder. The powder was dissolved in acetone, filtered through celite and the eluate containing metformin free base was concentrated under reduced pressure.

[0068] or

[0069] In a beaker, Amberlyst A-26(OH) ion exchange resin (60.097) was mixed with ...

Embodiment 2

[0072] Example 2: Preparation of metformin R-(+)-lipoate in acetone

[0073] Dissolve the metformin (free base) prepared in step 1.1 above in 70 mL of acetone. Dissolve R-(+)-lipoic acid in 10 mL of acetone. The two solutions were combined and stirred for 10 minutes. The resulting precipitate was filtered and the solid residue was vacuum dried to afford metformin R-(+)-lipoic acid salt (yield 95%).

Embodiment 3

[0074] Example 3: Preparation of metformin R-(+)-lipoic acid salt in acetonitrile

[0075] Dissolve the metformin (free base) prepared in step 1.1 above in 50 mL of acetonitrile. R-(+)-lipoic acid was dissolved in 20 mL of acetonitrile. The two solutions were combined and stirred for 10 minutes. The resulting precipitate was filtered and the solid residue was vacuum dried to afford metformin R-(+)-lipoic acid salt (yield 95%).

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Abstract

Described herein is a compound of Formula (I), which is the metformin salt of the naturally occurring endogenous biological compound, (R)-(+) a lipoic acid, pharmaceutical compositions containing the compound of Formula (I), and methods of treatment of diabetes or diabetic complications with the compound of Formula (I).

Description

Background of the invention [0001] Diabetes is already widespread and according to the World Health Organization, the number of people with diabetes will increase dramatically by 2030. This is an ominous forecast, as addressing the long-term complications of diabetes, including nephropathy, neuropathy, retinopathy, and cardiovascular complications, will have serious implications for public health budgets. The hallmark of diabetes is chronically elevated blood glucose levels. Abnormally elevated glucose levels are also known to have adverse effects on glutathione levels in predominantly diabetic tissues. Additionally, hyperglycemic conditions involve increased oxidative stress and increased production of reactive oxygen species. [0002] Despite the early discovery of insulin and its subsequent widespread use in the treatment of diabetes, and the later discovery and application of sulfonylureas and thiazolidinediones, such as troglitazone, rosiglitazone, or pioglitazone as or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/04A61K31/385
CPCC07D339/04A61P13/12A61P25/00A61P27/12A61P9/00A61P9/10A61P3/10
Inventor B·L·迈拉里N·E·瓦曼劳
Owner INDIGENE PHARMA
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