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Method for preparing cardiotonic drug LCZ696

A biphenyl, solid technology, applied in the field of preparation of pharmaceutical compounds, can solve the problems of high content, low purity of LCZ696, difficult to remove, etc.

Active Publication Date: 2015-08-26
BEIJING BOQUANJIAN PHARMA TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0025] The disadvantage of the above preparation method is that the obtained LCZ696 has low purity, and the impurities include (2R,4S)-5-biphenyl-4-yl-4-(3-carboxypropionylamino)-2-methyl-pentane Acid, ethyl (2R,4S)-5-biphenyl-4-yl-4-(2,5-dioxopyrrolidin-1-yl)-2-methylpentanoate, the content of both is high, And it is difficult to remove. Although the content of LCZ696 obtained by the above-mentioned prior art can be greater than 98.5%, the content of the above-mentioned two related impurities is greater than 0.3%, which affects the quality of the product. improvement of

Method used

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  • Method for preparing cardiotonic drug LCZ696
  • Method for preparing cardiotonic drug LCZ696
  • Method for preparing cardiotonic drug LCZ696

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Preparation of LCZ696

[0059] step 1,

[0060] Add 10g (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid hydrochloride and 60ml absolute ethanol into the reaction flask, stir Raise the temperature to 65-70°C; keep at 65-70°C, drop 5.6g of thionyl chloride into the reaction bottle under stirring; after the addition, keep stirring at 65-70°C for 3 hours; check the reaction with TCL (if the reaction is not complete, then Add an appropriate amount of thionyl chloride); after the reaction is completed, the solvent is evaporated under reduced pressure, and the temperature is 50°C, and steamed until no liquid flows out; 100ml of n-heptane is added to the residue, stirred and crystallized at room temperature for 1 hour; the temperature is lowered to 0~ Stir and crystallize at 10°C for 2 hours; filter, rinse the filter cake with 50ml of n-heptane, and dry in vacuum for 4 hours at a temperature of 50-55°C; obtain 10.8g of (2R,4S)-5-([1,1'- Biphenyl]-4-yl)-4-amino...

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Abstract

The invention relates to a preparation method of a pharmaceutical compound and particularly relates to a method for preparing a cardiotonic drug LCZ696. Particularly the synthetic route of the compound is as shown in the specification.

Description

technical field [0001] The invention relates to a preparation of a pharmaceutical compound, in particular to a preparation method of an anti-heart failure drug LCZ696. Background technique [0002] LCZ696, the chemical structure is as follows [0003] [0004] LCZ696 is a dual angiotensin receptor type 2 (AT II) and neprilysin inhibitor, consisting of valsartan and the NEP inhibitor drug sacubitril in a 1:1 ratio. The chemical name is as follows: [3-((1S,3R)-1-biphenyl-4-ylmethyl-3-ethoxycarbonyl-1-butylcarbamoyl)propanoic acid-(S)-3'- Methyl-2'-(pentanoyl{2"-(tetrazole-5-ylate)biphenyl-4'-ylmethyl}amino)butanoic acid]trisodium hemipentahydrate. [0005] As a combined substance, valsartan is an angiotensin receptor antagonist, which can be used for various types of hypertension, and has a better protective effect on the heart, brain and kidney. Hypertensive patients such as myocardial infarction, heart failure, proteinuria, and diabetes can be used routinely, and can b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/04C07C233/51C07C231/24C07C231/02C07C229/34
CPCC07C227/18C07C231/02C07C231/24C07D257/04C07C233/51C07C229/34
Inventor 王浩宇
Owner BEIJING BOQUANJIAN PHARMA TECH CO LTD
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