Orlistat nanosphere and application of same in preparation of obesity treatment drugs

A technology of orlistat and nano-microspheres, which is applied in the field of medicine, can solve the problems of inability to provide nano-products at the same time, and achieve the effect of making up for the lack of fat-soluble vitamins

Active Publication Date: 2018-09-14
ZHONGSHAN WANHAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] There is no technical teaching in the prior art that can provide orlistat and nano-prod...

Method used

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  • Orlistat nanosphere and application of same in preparation of obesity treatment drugs
  • Orlistat nanosphere and application of same in preparation of obesity treatment drugs
  • Orlistat nanosphere and application of same in preparation of obesity treatment drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1 Preparation and Structure Confirmation of Vitamin A Methacrylate (Compound 3a)

[0062]

[0063] Preparation: Take 28.65g vitamin A (0.100mol), put it in a 500mL three-necked flask, add petroleum ether to it under stirring, until vitamin A is completely dissolved, then add 5mg DCC (N,N'-dicyclohexyldi imine), and then add 13.21g of methacrylic acid (Compound 2, 0.15mol) in saturated petroleum ether solution, slowly raise the temperature to 50°C under stirring for reaction, and use high performance liquid chromatography to track the reaction to the end. Petroleum ether was distilled off under reduced pressure, and the resulting solid was washed with water and freeze-dried to obtain 31.55 g (0.089 mol) of a light yellow solid with a melting point of 51-52° C. and a yield of 89%.

[0064] Structural Confirmation:

[0065] Compound 2: 1 H-NMR (CDCl 3 ) δ (ppm): 6.69 (1H, s), 6.55 (1H, s), 2.03 (3H, s).

[0066] Vitamin A: 1 H-NMR (CDCl 3 )δ (ppm): 6.55 (1...

Embodiment 2

[0068] Example 2 Preparation and Structure Confirmation of Vitamin E Methacrylate (Compound 3b)

[0069]

[0070] Preparation: Take 43.72g of vitamin E (0.100mol), put it in a 500mL three-necked flask, add ether to it under stirring until the vitamin E is completely dissolved, then add 5mg of DMAP (4-dimethylaminopyridine) to it, and then add 13.23 g of methacrylic acid (compound 2, 0.16 mol) in saturated diethyl ether solution was slowly heated to 50° C. for reaction under stirring, and the reaction was tracked to the end point by high performance liquid chromatography. Ethyl ether was distilled off under reduced pressure, and the resulting solid was washed with water and then freeze-dried to obtain 45.39 g (0.091 mol) of off-white solid with a melting point of 42-43°C and a yield of 91%.

[0071] Structural Confirmation:

[0072] Compound 2: 1 H-NMR (CDCl 3 ) δ (ppm): 6.69 (1H, s), 6.55 (1H, s), 2.03 (3H, s).

[0073] Vitamin E: 1 H-NMR (CDCl 3 )δ (ppm): 2.74 (2H, t...

Embodiment 3

[0075] Example 3 Vitamin D 2 Preparation and Structure Confirmation of Methacrylate (Compound 3c)

[0076]

[0077] Preparation: Take 36.69g vitamin D 2 (0.101mol), placed in a 500mL three-necked flask, added diethyl ether therein under stirring until the vitamin E was completely dissolved, then added 5mg DMAP (4-dimethylaminopyridine) to it, then added 13.22g methacrylic acid (compound 2, 0.15 mol) of saturated ether solution, the temperature was slowly raised to 50°C under stirring for reaction, and the reaction was tracked to the end point by high performance liquid chromatography. Diethyl ether was distilled off under reduced pressure, and the obtained solid was washed with water and then freeze-dried to obtain 44.15 g (0.095 mol) of an off-white solid with a melting point of 85-87° C. and a yield of 95%.

[0078] Structural Confirmation:

[0079] Compound 2: 1 H-NMR (CDCl 3 ) δ (ppm): 6.69 (1H, s), 6.55 (1H, s), 2.03 (3H, s).

[0080] Vitamin D 2 : 1 H-NMR (CDC...

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Abstract

The invention relates to the technical field of medicine, in particular to an orlistat nanosphere and application of the same in preparation of obesity treatment drugs. The nanosphere comprises orlistat and a copolymer, wherein the copolymer is selected from one of a vitamin-A methacrylate-2-methacryloyloxyethyl phosphorylcholine copolymer, a vitamin-E methacrylate-2-methacryloyloxyethyl phosphorylcholine copolymer or a vitamin-D2 methacrylate-2-methacryloyloxyethyl phosphorylcholine copolymer. The encapsulation efficiency of the nanosphere is 82.67-93.83%. Animal experiments show that the vitamin absorption level of rats after the nanosphere is taken by the rats orally is obviously higher than the vitamin absorption level of rats after the orlistat and vitamins are taken by the rats orally at the same time (at the interval of two hours), and is similar to the vitamin absorption level of rats after the vitamins are taken by the rats individually and orally under fasting, so that deficiency of fat-soluble vitamin due to oral administration of the orlistat can be make up effectively, and safety weight loss can be realized.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to an orlistat nano-microsphere and its application in preparing medicine for treating obesity. Background technique [0002] Orlistat (orlistat) is a lipase inhibitor weight loss drug developed by Roche Pharmaceuticals. The trade name is Xenical. It was first launched in Europe and the United States in the late 1990s. Approved by the Food and Drug Administration to switch to an over-the-counter drug. Its chemical name is N-formyl-L-leucine (s)-1-[(2s,3s)-3-hexyl-4oxy-2-epoxypropylmethyl]dodecyl ester, also known as Tetrahydrolipstatin (THL) is a semi-synthetic lipstatin derivative, and its chemical structure is shown in the figure below: [0003] [0004] Orlistat forms a covalent bond with the serine residue of gastropancreatic lipase, thereby inactivating the enzyme and unable to hydrolyze triglycerides in food into absorbable fatty acids, thereby reducing the amount of fat...

Claims

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Application Information

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IPC IPC(8): A61K9/52A61K47/32A61K31/365A61P3/04
CPCA61K9/5026A61K31/365A61P3/04
Inventor 向飞杜志博彭韪
Owner ZHONGSHAN WANHAN PHARM CO LTD
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