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Preparation method of triazine derivative

A compound and alkyl technology, applied in the field of preparation of triazine derivatives, can solve the problems of reducing the probability of side effects and reducing the dosage of drugs

Pending Publication Date: 2022-07-19
JIANGSU HENGRUI MEDICINE CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is clinically desirable to use this highly active enantiomer instead of the racemate, and it is possible to reduce the overall dose of the drug, and the lower dose reduces the chance of side effects

Method used

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  • Preparation method of triazine derivative
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  • Preparation method of triazine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0127] Example 1 - Preparation of 1,6-dihydro-2-amino-4-dimethylamino-6-methyl-1,3,5-triazine

[0128] Option A:

[0129]

[0130] Metformin hydrochloride (16.5 g, 0.1 mol) was added to a methanol / water mixed solvent, and an aqueous solution of potassium hydroxide (1 eq) and a methanol solution of vinyl acetate (1 eq) were added dropwise, and then reacted at room temperature. After the reaction, the reaction solution was concentrated under reduced pressure, then ethanol was added and heated to 60° C., filtered while hot, and the filtrate was concentrated to obtain the compound of formula I-a (14.7 g, yield 95%).

[0131] HRMS(ESI)Calcd.for C6H14N5 + [M+H] + 156.1249; Found: 156.1256.

[0132] 1 H NMR (400MHz, D 2 O): 4.93-4.88(m, 1H), 3.07(s, 6H), 1.45-1.44(d, 6Hz, 3H).

[0133] Option B:

[0134]

[0135] Metformin acetate (18.9 g, 0.1 mol) was added to methanol, and ammonia water (2 eq) and vinyl acetate (1.2 eq) were added dropwise, and then reacted at 60°C. A...

Embodiment 2

[0139] Example 2—Preparation and Resolution of 1,6-dihydro-2-amino-4-dimethylamino-6-methyl-1,3,5-triazine

[0140] (1) Metformin acetate (18.9 g, 0.1 mol) was added to methanol, and ammonia water (2 eq) and vinyl acetate (1.2 eq) were added dropwise, and then reacted at 60°C. After the reaction was completed, the reaction solution was concentrated under reduced pressure, the solution was concentrated to dryness, isobutanol was added and refluxed until fully dissolved, cooled to 65 ° C, acetone was added, the temperature was lowered to 0 ° C again, stirred for 1 hour, filtered, and the filter cake was washed twice with acetone , and dried to obtain the compound of formula I-a (17.6 g, yield 82%).

[0141] (2) Dissolve the racemic compound of formula I-a (8.43g, 39.2mmol) in methanol, add a methanol solution of di-O,O'-p-toluoyl-D-tartaric acid (10.65g, 27.6mmol), After stirring and crystallization for 2 hours, the filter cake was dried to obtain di-p-toluoyl-D-tartrate (10.3g...

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PUM

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Abstract

The invention relates to a preparation method of a triazine derivative. Specifically, the invention relates to a preparation method of a compound as shown in a formula I-a and a derivative thereof, the preparation method comprises a step of reacting a biguanide substrate with vinyl ester or vinyl amide, and the invention also relates to a method for resolving enantiomers of the compound as shown in the formula I-a and the derivative thereof through chiral acid. The preparation method is few in steps, low in cost and suitable for industrial production, and the obtained product is high in purity.

Description

technical field [0001] The present disclosure relates to the field of medicinal chemistry, in particular to a preparation method of a class of triazine derivatives. Background technique [0002] Dihydro-1,3,5-triazine derivatives have been shown to be useful in the treatment of conditions associated with insulin resistance, especially type II diabetes. There have been some prior art reports on the synthesis of dihydro-1,3,5-triazine derivatives. For example, WO2001055122 discloses the synthesis of biguanide and aldehyde, acetal or hemiacetal compounds under acidic conditions to obtain dihydro- Methods for 1,3,5-triazine derivatives; WO2009095159 discloses methods for synthesizing biguanide and polyaldehyde compounds under acidic conditions to obtain dihydro-1,3,5-triazine derivatives; WO2009141040 and WO2009062483 disclose A method for synthesizing biguanide compounds and aldehyde compounds under basic conditions to obtain dihydro-1,3,5-triazine derivatives. [0003] Furth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/10C07C69/78A61K31/53A61P35/00
CPCC07D251/10C07C69/78A61P35/00C07B2200/07C07B2200/13
Inventor 赵思涵张辉薛州洋赵鸿樊波
Owner JIANGSU HENGRUI MEDICINE CO LTD
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