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2-(2-methacrylamide triglycyl) aminomalonate ester as well as preparation method and application thereof

A technology of methacrylamidotriglycyl and aminomalonate is applied in chemical instruments and methods, organic chemistry, peptides, etc., and can solve the problems of low total yield, high cost, complicated synthesis method and the like

Inactive Publication Date: 2010-06-09
JIANGSU AOSAIKANG PHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] Above-mentioned aminomalonate platinum complex Prolindac synthetic method is loaded down with trivial details, especially prepare target product aminomalonate platinum complex Prolindac from raw material hydroxypropyl methacrylate (HPMA) and need pass through three-step reaction, cause total yield Low, high cost, not easy for industrial production

Method used

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  • 2-(2-methacrylamide triglycyl) aminomalonate ester as well as preparation method and application thereof
  • 2-(2-methacrylamide triglycyl) aminomalonate ester as well as preparation method and application thereof
  • 2-(2-methacrylamide triglycyl) aminomalonate ester as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Preparation of Diethyl 2-(2-Methacrylamidoglycylglycylglycylglycyl)aminomalonate

[0084] (1) Preparation of 2-(Fmoc-glycylglycylglycyl)aminomalonate diethyl ester

[0085] Drop into diethyl aminomalonate hydrochloride 21.2g (0.1mol) and 40ml deionized water in the reaction flask, slowly add 11.5 grams (0.14mol) sodium bicarbonate powder after stirring and dissolving, a large amount of bubbles are released, add After completion, the reaction was stirred for 20 minutes, extracted with ethyl acetate (50ml*3), the organic layers were combined, dried, filtered to remove the desiccant, and concentrated under reduced pressure to remove the solvent to obtain diethyl aminomalonate (for use).

[0086] Put 2g of 1-hydroxybenzotriazole (HOBT) (0.015mol), 800ml of acetonitrile, pre-prepared diethyl aminomalonate (0.1mol) and 37 grams of Fmoc-glycylglycine into another reaction flask Acylglycine (0.09mol), under nitrogen protection, cooled to about 0°C, added 20.6g of dicyclohexylc...

Embodiment 2

[0103] Preparation of Diethyl 2-(2-Methacrylamidoglycylglycylglycylglycyl)aminomalonate

[0104] (1) Preparation of 2-(Boc-glycylglycylglycyl)aminomalonate diethyl ester

[0105] Drop into diethyl aminomalonate hydrochloride 318g (1.5mol) and 700ml deionized water in the reaction flask, slowly add 161 grams (1.92mol) sodium bicarbonate powder under stirring, stir and react for 20 minutes after adding, Extract with ethyl acetate (800ml*3), combine the organic layers, dry, filter to remove the desiccant, and concentrate under reduced pressure to remove the solvent to obtain diethyl aminomalonate.

[0106] Put 30 g of 1-hydroxybenzotriazole (HOBT) (0.22 mol), 12 L of acetonitrile, pre-prepared diethyl aminomalonate (1.5 mol) and 389 g of Boc-glycylglycyl in a reaction kettle Glycine (1.35mol), under nitrogen protection, cooled to about 0°C, added 309g of dicyclohexylcarbodiimide (1.5mol) in portions, and controlled the temperature below 5°C. After the addition, it was reacted a...

Embodiment 3

[0123] Preparation of dimethyl 2-(2-methacrylamidoglycylglycylglycylglycyl)aminomalonate

[0124] (1) Preparation of dimethyl 2-(Fmoc-glycylglycylglycyl)aminomalonate

[0125] Drop into dimethyl aminomalonate hydrochloride 14.7g (0.1mol) and 40ml deionized water in the reaction bottle, slowly add 12.6 grams (0.15mol) sodium bicarbonate powder after stirring and dissolving, a large amount of bubbles are released, add After completion, the reaction was stirred for 20 minutes, extracted with ethyl acetate (50ml*3), the organic layers were combined, dried, filtered to remove the desiccant, and concentrated under reduced pressure to remove the solvent to obtain dimethyl aminomalonate (for use).

[0126] Put 1.35g of 1-hydroxybenzotriazole (HOBT) (0.01mol), 800ml of acetonitrile, dimethyl aminomalonate (0.1mol) and 30.8 grams of Fmoc-glycylglycylglycine into another reaction flask (0.075mol), under nitrogen protection, cooled to about 0°C and added 20.6g of dicyclohexylcarbodiimide...

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Abstract

The invention relates to 2-(2-methacrylamide triglycyl) aminomalonate ester (I) with a structural formula as below as well as a preparation method and application thereof. The 2-(2-methacrylamide triglycyl) aminomalonate ester (I) can be applied to preparing an aminomalonate platinum complex Prolindac; the preparation method has short synthesis steps, simple and convenient operation, good product quality, high yield and easy industrialized production; and wherein R is equal to (C1 to C5) alkyl.

Description

technical field [0001] The present invention relates to a kind of 2-(2-methacrylamido triglycyl) aminomalonate compound and preparation of 2-(2-methacrylamido triglycyl) aminomalonate Methods and applications of ester compounds. Background technique [0002] Aminomalonate platinum complex Prolindac (also known as: AP5346) is a new type of cyclohexanediamine platinum tumor targeting drug, developed by Access Pharmaceuticals, Inc.; aminomalonic acid Platinum ester complex Prolindac (AP5346) is a compound developed to solve the sensory neurotoxicity within the dose range of oxaliplatin. At present, platinum aminomalonate complex Prolindac (AP5346) has completed the clinical trial of ovarian cancer in Europe. Phase II clinical research, with satisfactory clinical research results. [0003] Aminomalonate platinum complex Prolindac (AP5346) chemical structural formula is as follows: [0004] [0005] (q=36-47, r=2.3, s=1) [0006] Aminomalonate platinum complex Prolindac (A...

Claims

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Application Information

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IPC IPC(8): C07K5/103C07F15/00A61P35/00
CPCY02P20/55
Inventor 赵俊宗在伟伏世建杨建楠
Owner JIANGSU AOSAIKANG PHARMA CO LTD
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