A kind of preparation technology of amd3465

A preparation process and disease technology, which is applied in the new process field of compound AMD3465 synthesis, can solve the problems of large-scale production operation difficulty, difficult source of tetraazacyclotetradecane, high price, etc., achieve good promotion and application prospects, and be easy to industrialize The effect of large production and easy operation

Active Publication Date: 2016-04-13
SHANDONG LUBEI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This method will use column chromatography to separate when the product is separated in the reaction, and the source of 1,4,8,11-tetraazacyclotetradecane itself is more difficult, and the price is also higher, so the large-scale production of this method very difficult to operate

Method used

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  • A kind of preparation technology of amd3465
  • A kind of preparation technology of amd3465
  • A kind of preparation technology of amd3465

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Add 109 grams of 2-aminomethylpyridine, 264 grams of p-dibromobenzyl, 200 grams of anhydrous potassium carbonate, and 1800 mL of acetonitrile into a reaction flask, heat to 70°C, react for 2 hours, cool to room temperature, and filter out potassium carbonate. The solvent was evaporated to dryness under reduced pressure, and the residue was poured into 1000 mL of water, stirred for 30 minutes, and filtered to obtain a light yellow solid. The solid was added to 1000 mL of methanol and stirred at room temperature for 1 hour, and filtered to obtain 252.3 g of solid (4-(bromomethyl)benzyl)-N-(pyridin-2-ylmethyl)methanamine, with a yield of 87.0%. ESI (M / Z) 291.2 (M+H+), elemental analysis (C14H15N2Br) measured value (theoretical value) C57.70% (57.75%), H5.20% (5.19%), N9.61% (9.62%) .

[0013] Dissolve 252 grams of (4-(bromomethyl)benzyl)-N-(pyridin-2-ylmethyl)methanamine, 210.0 grams of tricarbonyl ring ring, and 110 grams of anhydrous potassium carbonate in 1500 mL of ac...

Embodiment 2

[0016] Add 109 grams of 2-aminomethylpyridine, 264 grams of p-dibromobenzyl, 200 grams of anhydrous sodium carbonate, and 800 mL of DMF into a reaction flask, heat to 80°C, react for 2 hours, cool to room temperature, and filter out anhydrous sodium carbonate. The remainder of the reaction solution was poured into 2000 mL of ice water, stirred for 30 minutes, and filtered to obtain a light yellow solid. The solid was added to 1000 mL of methanol and stirred at room temperature for 1 hour, and filtered to obtain 239.3 g of solid (4-(bromomethyl)benzyl)-N-(pyridin-2-ylmethyl)methanamine, with a yield of 87.0%. ESI (M / Z) 291.2 (M+H+), elemental analysis (C14H15N2Br) measured value (theoretical value) C57.70% (57.75%), H5.20% (5.19%), N9.61% (9.62%) .

[0017] Dissolve 239 grams of (4-(bromomethyl)benzyl)-N-(pyridin-2-ylmethyl)methanamine, 220.0 grams of tricarbonyl ring ring, and 120 grams of anhydrous potassium carbonate in 1500 mL of acetonitrile, 80 After reacting at ℃ for 3...

Embodiment 3

[0020] Add 115 grams of 2-aminomethylpyridine, 302 grams of p-dibromobenzyl, 205 grams of anhydrous sodium carbonate, and 800 mL of DMF into a reaction flask, heat to 80°C, react for 2 hours, cool to room temperature, and filter out anhydrous sodium carbonate. The remainder of the reaction solution was poured into 2000 mL of ice water, stirred for 35 minutes, and filtered to obtain a light yellow solid. The solid was added to 1000 mL of methanol and stirred at room temperature for 1 hour, and filtered to obtain 241.5 g of solid (4-(bromomethyl)benzyl)-N-(pyridin-2-ylmethyl)methanamine, with a yield of 87.6%. ESI (M / Z) 291.2 (M+H+), elemental analysis (C14H15N2Br) measured value (theoretical value) C57.70% (57.75%), H5.20% (5.19%), N9.61% (9.62%) .

[0021] Dissolve 241.5 grams of (4-(bromomethyl)benzyl)-N-(pyridin-2-ylmethyl)methanamine, 231.0 grams of tricarbonyl ring ring, and 116 grams of anhydrous sodium carbonate in 1500 mL of acetonitrile, 75 After reacting at ℃ for 3 ...

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Abstract

The invention discloses a novel preparation technology of molecule AMD3465 for treating hematopoietic stem cell symptoms. The chemical name of the molecule AMD3465 is 2-pyridine methylamino, N-((3-(1,4,8,11-tetraazacyclotetradecane-methyl)benzyl)methyl-). The novel preparation technology comprises the steps of: with 2-(aminomethyl)pyridine as a raw material, singly butting the 2-(aminomethyl)pyridine with p-Xylylene dibromide, then butting with tricarbonyl torus, and reducing to obtain the product AMD3465 (I), wherein the purity of the product AMD3465 (I) is above 99.5 percent. The novel preparation technology is reasonable in process route and simple and convenient to operation and has broad prospects of popularization and application.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a new process for compound AMD3465 synthesis. Background technique [0002] The chemical name of AMD3465 is 2-picolylamino, N-((3-(1,4,8,11-tetraazidocyclotetradecane-methyl)benzyl)methyl-), Pharmacokinetics of AMD3465 Clinical studies in mice and dogs, rapid absorption subcutaneous administration, AMD3465 was cleared from canine plasma in a biphasic manner with a terminal half-life of 1.56-4.63h. Comparison of exposed intravenous and subcutaneous injections showed 100% bioavailability for subcutaneous administration. AMD3465 induced leukocytosis in mice and dogs when administered subcutaneously, with peak mobilization occurring between 0.5 and 1.5 hours following subcutaneous administration in mice, and peak plasma concentrations of the compound with maximal mobilization at subcutaneous administration Canines have shown that AMD3465 has the potential to mobi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12
Inventor 王克柳王美海
Owner SHANDONG LUBEI PHARMA
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