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Inclusion compound of cannabidiol with cucurbituril and derivatives of cucurbituril, and preparation method for inclusion compound

A technology of cannabidiol and cucurbituril, which is applied in the direction of drug combination, active ingredients of hydroxyl compounds, medical preparations of non-active ingredients, etc., can solve the problems of no cannabidiol and other problems, and overcome the extremely poor water solubility and stability High and mild reaction conditions

Active Publication Date: 2020-03-31
云南省农业科学院经济作物研究所
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there is no report on the inclusion compound of cannabidiol, cucurbituril and its derivatives

Method used

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  • Inclusion compound of cannabidiol with cucurbituril and derivatives of cucurbituril, and preparation method for inclusion compound
  • Inclusion compound of cannabidiol with cucurbituril and derivatives of cucurbituril, and preparation method for inclusion compound
  • Inclusion compound of cannabidiol with cucurbituril and derivatives of cucurbituril, and preparation method for inclusion compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: cannabidiol and cucurbit[7] urea (n=7, R 1 =H,R 2 =H) preparation of clathrates

[0021] Add 1mmol / mL cucurbit[7]urea (n=1, R 1 = R 2 = H) 10mL aqueous solution, then add 100mmol cannabidiol crystals, cucurbit [7] urea: cannabidiol substance ratio is 1:10, stir at 500rpm at 20°C in the dark for 7d, after the reaction is completed, use 0.1 The microporous membrane of μm was filtered to remove undissolved solids, and the filtrate was vacuum-dried (100Pa, 12h) to obtain a white powder, and the NMR test results showed that it was the inclusion compound of cannabidiol and cucurbit[7]uril ( 1 H NMR data, 500MHz, D 2 O:δ0.5-2.5(H of CBD,8H),3.0-4.0(H of CBD,4H),4.25-4.38(H of CB,7H),5.0-5.2(H of CBD,2H),5.4- 5.55 (H of CB, 14H), 5.6-5.75 (H of CB, 7H)). pass 1 The HNMR data conversion can be obtained, calculated based on the solubility of cannabidiol in water, the solubility is 8.41mg / mL.

Embodiment 2

[0022] Embodiment 2: cannabidiol and cucurbit[7] urea (n=3, R 1 =-OH,R 2 =-OH) inclusion compound preparation

[0023] The cucurbit [7] urea (n=3, R 1 =-OH, R 2 =-OH) has a chemical structural formula as follows:

[0024]

[0025] Add 1mmol / mL cucurbit[7]urea (n=3, R 1 = R 2 =-OH) N,N-dimethylformamide-water solution 30mL (solvent is a mixed solvent of N,N-dimethylformamide and water, N,N-dimethylformamide and water v:v= 1:9), then add 10mL of 3mmol / mL cannabidiol acetone-water suspension (the solvent is acetone-water mixed solvent, v:v=2:1 of acetone and water), cucurbit[7]urea (n= 3, R 1 =-OH, R 2 =-OH): the molar ratio of cannabidiol is 1:1, stirred at 1500rpm in the dark for 1d at 65°C, filtered through a 0.1μm microporous membrane to remove undissolved solids, and the filtrate was vacuum-dried (100Pa, 12h ) to obtain a white powder, the NMR test results show that it is cannabidiol and cucurbit [7] urea (n = 3, R 1 = R 2 =-OH) clathrate ( 1 H NMR data, 500MH...

Embodiment 3

[0026] Embodiment 3: cannabidiol and cucurbit[7] urea (n=1, R 1 =-(CH 2 ) 4 Cl,R2 =-H) preparation of clathrate

[0027] The [7] urea gourd [7] urea (n=1, R 1 =-(CH 2 ) 4 Cl,R 2 =-H) The chemical structural formula is as follows:

[0028]

[0029] Add 1mmol / mL cucurbit[7]urea (n=1, R 1 =-(CH 2 ) 4 Cl,R 2 =-H) Methanol-water solution 10mL (solvent is a mixed solvent of methanol and water, methanol and water v:v=1:9), then add 10mmol / mL cannabidiol dimethyl sulfoxide-water suspension 5mL (solvent is dimethyl sulfoxide-water mixed solvent, v:v=1:9 of dimethyl sulfoxide and water), cucurbit [7] urea (n=1, R 1 =-(CH 2 ) 4 Cl,R 2 =-H): The molar ratio of cannabidiol is 1:5, stirred at 200rpm in the dark for 6h at 30°C, filtered through a 0.1μm microporous membrane to remove undissolved solids, and the filtrate was vacuum-dried (100Pa, 12h ) to obtain a white powder, the NMR test results show that it is cannabidiol and cucurbit [7] urea (n = 1, R 1 =-(CH 2 ) 4 Cl...

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Abstract

The invention discloses an inclusion compound of cannabidiol with cucurbituril and derivatives of the cucurbituril, and a preparation method for the inclusion compound. The cucurbituril and the derivatives thereof are cucurbituril [7] and derivatives thereof. The inclusion compound is prepared by adopting a solvent method. The inclusion compound prepared from the cannabidiol with the cucurbituriland the derivatives of the cucurbituril has good water solubility, stability and bioavailability. The preparation method comprises the following steps: adding cannabidiol crystals or a cannabidiol suspension into a solution of the cucurbituril and derivatives of the cucurbituril, carrying out a reaction under proper conditions, carrying out filtering, and carrying out freeze drying or vacuum drying so as to obtain the inclusion compound. The preparation method provided by the invention has the advantages of simple equipment, mild reaction conditions and easiness in industrial production, and can solve the problem that application of the cannabidiol in the fields of medicines, foods, cosmetics and the like is limited due to extremely low solubility of the cannabidiol in water.

Description

technical field [0001] The invention belongs to the technical field of preparation preparation, and in particular relates to an inclusion compound of cannabidiol, cucurbituril and derivatives thereof and a preparation method thereof. Background technique [0002] Marijuana (Cannabis sativa L.) is an annual herbaceous plant belonging to the family Cannabis genus, often dioecious. It is an important traditional economic crop in my country and is widely distributed all over the world. As one of the five grains, hemp has played an important role in textiles, food and medicine since ancient times. The development and utilization of hemp in modern times is not limited to primary processing products such as hemp fiber, hemp seeds and oil. Through the industrial hemp More than 25,000 products have been produced through deep processing and utilization, involving textiles, papermaking, building materials, food, medicine and many other fields. One of the most notable is the research o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/69A61K31/05A61P25/08A61P25/00
CPCA61K31/05A61K47/6949A61P25/00A61P25/08
Inventor 吕品郭鸿彦杨明郭蓉许艳萍陈璇张庆滢郭孟璧
Owner 云南省农业科学院经济作物研究所
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