Compound Dahpe, preparation method and application thereof

A compound, the technology of heptyloxy, which is applied in the preparation of organic compounds, cyanide reaction preparation, chemical instruments and methods, etc., can solve the problems of limited application of transdermal absorption enhancers and low yield, and achieve the promotion of transdermal absorption , Yield increase, enhance the efficacy of the drug

Inactive Publication Date: 2018-07-06
HANSHAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] The object of the present invention is to solve the above-mentioned defects of the prior art, provide a kind of brand-new compound Dahpe and its preparation method and application, aim to solve the limited application of existing transdermal absorption enhancers in clinical transdermal preparations of cardiovascular and cerebrovascular drugs, And 2-(N, N-dihydroxyethyl) alanine ester compound preparation method yield is low etc.

Method used

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  • Compound Dahpe, preparation method and application thereof
  • Compound Dahpe, preparation method and application thereof
  • Compound Dahpe, preparation method and application thereof

Examples

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preparation example Construction

[0019] On the other hand, the embodiment of the present invention also provides a preparation method of the above-mentioned compound Dahpe, the preparation method comprising the following steps:

[0020] S01: Obtain three raw materials of 5-heptyloxy-1-pentanol, 2-chloropropionyl chloride and diethylaminol;

[0021] S02: acylating 5-heptyloxy-1-pentanol and 2-chloropropionyl chloride in step S01 to obtain intermediate 2-chloropropionic acid-5-heptyloxy-1-pentyl ester;

[0022] S03: Dechlorination of the intermediate 2-chloropropionic acid-5-heptyloxy-1-pentyl ester in step S02 and diethylamino alcohol in step S01 to obtain the compound Dahpe of the above-mentioned invention embodiment .

[0023] The reaction process of the above-mentioned preparation method is as follows. The preparation method not only has simple process, easy operation and low cost, but also has no pollution to the environment during the preparation process. Compared with the preparation method of the prio...

Embodiment 1

[0044] This embodiment provides a compound Dahpe, whose chemical name is: 2-(N,N-dihydroxyethyl)alanine-5-heptyloxy-1-pentyl ester; the structural formula is shown in the aforementioned formula I.

[0045] The preparation method of above-mentioned compound Dahpe is as follows:

[0046] S11: Obtain three raw materials of 5-heptyloxy-1-pentanol, 2-chloropropionyl chloride and diethylaminol;

[0047] S12: Acylation reaction of 5-heptyloxy-1-pentanol and 2-chloropropionyl chloride to obtain intermediate 2-chloropropionic acid-5-heptyloxy-1-pentyl ester;

[0048] S13: Dechlorination of the intermediate 2-chloropropionic acid-5-heptyloxy-1-pentyl ester and diethylamino alcohol was carried out to obtain the compound Dahpe of the above-mentioned embodiment of the invention.

[0049] Concrete above-mentioned step S12 acylation reaction, the synthesis process of intermediate 2-chloropropionic acid-5-heptyloxy-1-pentyl ester is:

[0050] S121: In a 50mL three-neck flask, place 9.47g (4...

Embodiment 2

[0059] This embodiment provides a compound Dahpe, whose chemical name is: 2-(N,N-dihydroxyethyl)alanine-5-heptyloxy-1-pentyl ester; the structural formula is shown in the aforementioned formula I.

[0060] The preparation method of above-mentioned compound Dahpe is as follows:

[0061] S21: Obtain three raw materials of 5-heptyloxy-1-pentanol, 2-chloropropionyl chloride and diethylaminol;

[0062] S22: Acylation reaction of 5-heptyloxy-1-pentanol and 2-chloropropionyl chloride to obtain intermediate 2-chloropropionic acid-5-heptyloxy-1-pentyl ester;

[0063] S23: Dechlorination of the intermediate 2-chloropropionic acid-5-heptyloxy-1-pentyl ester and diethylamino alcohol was carried out to obtain the compound Dahpe of the above-mentioned embodiment of the invention.

[0064] Concrete above-mentioned step S22 acylation reaction, the synthesis process of intermediate 2-chloropropionic acid-5-heptyloxy-1-pentyl ester is:

[0065] S221: In a 50mL three-necked flask, place 8.68g ...

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Abstract

Belonging to the field of chemical medicine, the invention in particular relates to a compound Dahpe, a preparation method and application thereof. The molecular structural formula of the compound Dahpe is shown as formula I in the specification. The preparation method of the compound Dahpe includes the steps of: acquiring the following three raw materials: 5-heptyloxy-1-pentanol, 2-chloropropionyl chloride and diethylamine alcohol; subjecting the 5-heptyloxy-1-pentanol and 2-chloropropionyl chloride to acylation reaction to obtain an intermediate 2-chloropropionic acid-5-heptyloxy-1-amyl ester; and subjecting the intermediate 2-chloropropionic acid-5-heptyloxy-1-amyl ester and the diethylamine alcohol to dechlorination amination reaction so as to obtain the compound Dahpe. The compound Dahpe can be applied to transdermal delivery preparations of cardiovascular and cerebrovascular drugs, significantly promote transdermal absorption of cardiovascular and cerebrovascular drugs, and enhance the efficacy of the drugs, and the transdermal penetration promoting activity is significantly superior to the prior art.

Description

technical field [0001] The invention belongs to the field of chemical medicine, and in particular relates to a compound Dahpe and its preparation method and application. Background technique [0002] Transdermal drug delivery systems (TDDS) refer to controlled-release preparations that are administered through the skin and have a systemic therapeutic effect. There is no "first-pass effect" of the liver, and it is not damaged by digestive enzymes in the gastrointestinal tract. It has the advantages of long time, less toxic and side effects and adverse reactions, and high curative effect. Due to the barrier effect of the skin and the physical and chemical properties of the drug itself, some drugs have a low penetration rate through the skin, and it is difficult for the drug to reach the effective therapeutic concentration through the skin. Therefore, how to strengthen the transdermal absorption of the drug is the key Research hotspots now. At present, the commonly used metho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/12C07C227/08A61K47/18A61K31/4422A61P9/00
CPCA61K9/0014A61K31/4422A61K47/183C07C227/08C07C229/12
Inventor 李伟杰肖叶玉
Owner HANSHAN NORMAL UNIV
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