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Insulin derivative

An insulin derivative, insulin technology, applied in the direction of insulin, hormone peptides, animal/human proteins, etc., can solve problems such as tissue inflammation

Inactive Publication Date: 2009-05-20
NOVO NORDISK AS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Another drawback is that solid particles of insulin can act as a local irritant, causing inflammation of the tissue at the injection site

Method used

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  • Insulin derivative
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[1194] Nε B29 - Synthesis of ω-carboxy-pentadecanoyl-γ-L-glutamine desB30 human insulin

[1195]

[1196] Step 1: Mono-tert-Butyl Hexadecandioate

[1197] Hexadecanedioic acid (40.0 g, 140 mmol) was suspended in toluene (250 ml), and the mixture was heated to reflux. N,N-Dimethylformamide di-tert-butyl acetal (76.3 g, 375 mmol) was added dropwise over a period of 4 hours. The mixture was refluxed overnight. The solvent was removed in vacuo at 50°C, the crude product was suspended in DCM / AcOEt (500ml, 1:1) and stirred for 15 minutes. The solid was collected by filtration and triturated with DCM (200ml). The filtrate was evaporated in vacuo to give crude mono-tert-butyl hexadecandioate, 30 g. The product was suspended in DCM (50ml), cooled with ice for 10 minutes, and filtered. The solvent was removed in vacuo to give 25 g of crude mono-tert-butyl hexadecanedioate, which was recrystallized in heptane (200 ml) to give mono-tert-butyl hexadecandioate, 15.9 g (33%)...

Embodiment 2

[1212] Nε B29 - Synthesis of ω-carboxy-pentadecanoyl-γ-amino-butyryl desB30 human insulin

[1213]

[1214] This compound was prepared in a manner similar to Example 1 from hexadecanedioic acid and γ-aminobutyric acid.

[1215] ω-tert-Butyl-carboxy-pentadecanoyl-γ-amino-butyric acid succinimidyl ester

[1216] 1 H-NMR (CDCl 3 )δ: 5.80(m, 1H), 3.36(dd, 2H), 2.84(s, 4H), 2.65(t, 2H), 2.21-2.13(m, 4H), 1.99(p, 2H), 1.44(s , 9H), 1.66-1.51 (m, 6H), 1.25 (br, 20H).

[1217] Nε B29 -omega-carboxy-pentadecanoyl-gamma-amino-butyryl desB30 human insulin LCMS 6059.9;C 273 h 411 N 65 o 79 S 6 The calculated value is 6060.1.

Embodiment 3

[1219] Nε B29 - Synthesis of ω-carboxy-tetradecanoyl-γ-L-glutamine desB30 human insulin

[1220]

[1221] This compound was prepared in a similar manner to Example 1 from pentadecanedioic acid and L-glutamine.

[1222] LCMS 6088.2;C 273 h 410 N 66 o 80 S 6 The calculated value is 6089.1.

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Abstract

The present invention relates to novel human insulin derivatives which are soluble at physiological pH values and have a prolonged profile of action. The invention also relates to methods of providing such derivatives, to pharmaceutical compositions containing them, to methods of treating diabetes and hyperglycaemia using the insulin derivatives of the invention and to the use of such insulin derivatives in the treatment of diabetes and hyperglycaemia.

Description

field of invention [0001] The present invention relates to novel human insulin derivatives which are soluble at physiological pH and have a prolonged action profile. The present invention also relates to methods for providing the above-mentioned derivatives, pharmaceutical compositions containing them, methods for treating diabetes and hyperglycemia using the insulin derivatives of the present invention, and applications of the insulin derivatives in treating diabetes and hyperglycemia. Background of the invention [0002] Currently, the treatment of diabetes, both type 1 and type 2 diabetes, increasingly relies on so-called intensive insulin therapy. In this regimen, patients are treated with multiple daily insulin injections consisting of one or two daily injections of long-acting insulin to cover basal insulin requirements, supplemented with large boluses of fast-acting insulin to cover meal-related insulin need. [0003] Long-acting insulin compositions are well known ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/62A61K38/28
CPCC07K14/62A61K38/28
Inventor F·休巴莱克T·霍格-詹森I·约纳森P·W·加里贝P·雅各森S·哈夫伦德J·T·克德拉
Owner NOVO NORDISK AS