Lipid-lowering antidiabetic agent

a lipid-lowering and anti-diabetic agent technology, applied in the field of poly unsaturated fatty acids, can solve the problems of limiting the use of hypoglycemic agents, affecting and abnormally elevated glucose levels, etc., to achieve the effect of improving the bioavailability of their component moities and high water solubility

Inactive Publication Date: 2012-07-12
THETIS PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0025]Compounds of the present invention can be considered as designer dual-acting drugs and additionally possess a means for improving the bioavailability of their component moieties as a result of their high degree of water solubility.

Problems solved by technology

It is also known that abnormally elevated glucose levels have an adverse impact on glutathione levels in key diabetic tissues.
In spite of the early discovery of insulin and its subsequent widespread use in the treatment of diabetes, and the later discovery of and use of sulfonylureas, and thiazolidenediones, such as troglitazone, rosiglitazone or pioglitazone, as oral hypoglycemic agents, the treatment of diabetes remains less than satisfactory.
However, the clinically available hypoglycemic agents can either have side effects limiting their use, or an agent may not be effective with a particular patient.
Metformin does not promote weight gain and has beneficial effects on several cardiovascular risk factors.
The body uses triglycerides to store fat but high (>200 mg / dl) and very high (>500 mg / dl) triglycerides are associated with atherosclerosis which increases the patients risk of heart attack and stroke.
Clinically, pre-diabetes means that blood sugar level is higher than normal, but it's not yet increased enough to be classified as type 2 diabetes.
Still, without intervention, prediabetes is likely to become type 2 diabetes over time
Also diabetic patients have impaired circulation which manifests itself in the slow healing of wounds in the foot and lower leg and puts the patient at risk for amputation.

Method used

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  • Lipid-lowering antidiabetic agent
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  • Lipid-lowering antidiabetic agent

Examples

Experimental program
Comparison scheme
Effect test

example 2

Preparation of {[amino(imino)methyl]amino } (dimethylamino)methaniminium (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate

[0044]N,N-dimethylimidodicarbonimidic diamide. N,N-dimethylimidodicarbonimidic diamide hydrochloride (4.06 g, 24.5 mmol) was dissolved in IN sodium hydroxide (24.5 mL, 24.5 mmol) and stirred at room temperature for 30 minutes. The solution was concentrated in vacuum and to the residue was added ethanol (80 mL). The mixture was carefully concentrated to azeotropically remove water. To the resulting solid was added (60 mL) and the suspension was filtered to remove precipitated sodium chloride. The filtrate was concentrated and the resulting solid was placed on high vaccum overnight to yield 3.22 g (102%) of N,N-dimethylimidodicarbonimidic diamide as a white solid.

{[Amino(imino)methyl] amino}(dimethylamino)methaniminium (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate

[0045]N,N-Dimethylimidodicarbonimidic diamide (968 mg, 7.61 mmol) was dissolved in ...

example 3

Preparation of {[amino(imino)methyl]amino}(dimethylamino)methaniminium (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoate

[0046]N,N-dimethylimidodicarbonimidic diamide.

[0047]Metformin hydrochloride (331.25 g, 2 moles) was weighed into a 4000 mL beaker containing a stir bar. 1N KOH (1980 mL, 1.998 moles) was added, the beaker was covered, and the mixture was stirred for 2 h. The solids were collected by vacuum filtration, and the filtrate was concentrated to a damp solid. Isopropanol (500 mL) was added and after brief swirling, the mixture was concentrated. The residual white solid was dried for 16 h in a vacuum oven (yield: 269.08 g).

{[Amino(imino)methyl]amino}(dimethylamino)methaniminium (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoate

[0048]Metformin free base (50.10 g, 0.366 mole) was weighed into a 4000 mL beaker containing a stir bar. CH3CN (2000 mL) was added and the mixture was rapidly stirred until all metformin had dissolved. A fine white solid was removed by vacuum filtr...

example 4

[0049]The solubility of the compound of Example 1 in water was compared with that of eicosapentaenoic acid (EPA).

[0050]Measurement of the water solubility of the test compounds is accomplished by using methods well known to those skilled in the art. Specifically, to a weighed amount of the test compound of Example 1 distilled water is added in small portions until a clear solution is obtained. The total-volume of the solution is measured. The water solubility is calculated by dividing the weight of the salt, in mg, by the volume of the solution, in mL. The water solubility of the compound of Example 1 when measured using the above technique, was determined to be 50 mg / ml. Likewise, the water solubility of EPA was found to be <0.2 mg / mL. The compound of Example 1 is therefore, at least, 250 times more soluble in water than EPA itself. This is a clear indication of an unexpectedly high degree of bioavailability of the compositions of the invention. Highly water soluble medicinal prepa...

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Abstract

A composition which includes a salt of metformin and the use of the composition for treatment of or use in prediabetes, diabetes, lowering triglycerides and/or other conditions in mammals.

Description

CROSS REFERENCE TO RELATED APPLICATION[0001]The present application claims priority from U.S. provisional patent application 61 / 461,113 filed on Jan. 12, 2011, the contents of which are herein incorporated by reference.BACKGROUND OF THE INVENTION[0002]1. Field of the Invention[0003]The present invention relates to salts of poly unsaturated fatty acids with biguanides.[0004]2. Technical Background[0005]Diabetes mellitus has become pandemic and according to a forecast by the World Health Organization, there will be a sharp increase in the number of diabetic patients by the year 2030. This is an ominous forecast, because managing the long-term complications of diabetes, which include nephropathy, neuropathy, retinopathy, and cardiovascular complications, will have a serious impact on public health budgets. The hallmark of diabetes is chronically elevated blood glucose levels. It is also known that abnormally elevated glucose levels have an adverse impact on glutathione levels in key di...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/202A61P3/10A61P9/10A61P3/04A61P9/06A61P9/00C07C251/08A61P7/00
CPCA61K31/202A61K31/155C07C279/04C07C57/03C07C279/26A61P3/04A61P3/06A61P7/00A61P9/00A61P9/06A61P9/10A61P3/10C07C251/08A01N37/52
Inventor MYLARI, BANAVARA L.SCIAVOLINO, FRANK C.
Owner THETIS PHARMA
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