CN111574333A - Preparation process of water-soluble cannabidiol - Google Patents
Preparation process of water-soluble cannabidiol Download PDFInfo
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- CN111574333A CN111574333A CN202010291798.5A CN202010291798A CN111574333A CN 111574333 A CN111574333 A CN 111574333A CN 202010291798 A CN202010291798 A CN 202010291798A CN 111574333 A CN111574333 A CN 111574333A
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- cannabidiol
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- water
- arginine
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- QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 title claims abstract description 84
- 229950011318 cannabidiol Drugs 0.000 title claims abstract description 84
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 title claims abstract description 84
- PCXRACLQFPRCBB-ZWKOTPCHSA-N dihydrocannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)C)CCC(C)=C1 PCXRACLQFPRCBB-ZWKOTPCHSA-N 0.000 title claims abstract description 83
- QHMBSVQNZZTUGM-ZWKOTPCHSA-N cannabidiol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-ZWKOTPCHSA-N 0.000 title claims abstract description 74
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000002994 raw material Substances 0.000 claims abstract description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 20
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000003756 stirring Methods 0.000 claims abstract description 16
- 239000004475 Arginine Substances 0.000 claims abstract description 14
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 235000009697 arginine Nutrition 0.000 claims abstract description 14
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims abstract description 12
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 cannabidiol arginine ester Chemical class 0.000 claims abstract description 10
- 239000012141 concentrate Substances 0.000 claims abstract description 10
- 239000000706 filtrate Substances 0.000 claims abstract description 10
- 239000005457 ice water Substances 0.000 claims abstract description 10
- 229930064664 L-arginine Natural products 0.000 claims abstract description 9
- 235000014852 L-arginine Nutrition 0.000 claims abstract description 9
- 239000012043 crude product Substances 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 238000012544 monitoring process Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 238000005303 weighing Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 240000004308 marijuana Species 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention relates to a preparation process of water-soluble cannabidiol, belonging to the technical field of chemistry. Placing cannabidiol raw materials into a first ethanol solution to mix to form a first mixture, adding L-arginine into the first mixture, stirring for 5min to form a second mixture, adding 4-dimethylaminopyridine and dicyclohexylcarbodiimide into the second mixture, then adding 5% of hydrochloric acid ice water solution into a first filtrate to form a third mixture, dissolving the cannabidiol arginine ester crude product into the second ethanol solution, stirring to form a fourth mixture, placing the concentrate into a-20 ℃ environment, standing and crystallizing to obtain the water-soluble cannabidiol. The invention has the advantages that: the water-soluble cannabidiol is prepared by mixing, reacting and concentrating cannabidiol raw materials with the cannabidiol content of more than or equal to 98% for multiple times by using related reagents, so that the traditional method for producing by adopting an inclusion technology is replaced, the production efficiency is improved, and the complexity of the preparation process is reduced.
Description
The technical field is as follows:
the invention relates to a preparation process of water-soluble cannabidiol, belonging to the technical field of chemistry.
Background art:
cannabidiol, CBD, english: cannabidial is a pure natural ingredient extracted from the cannabis plant. The molecular formula of cannabidiol is C21H30O 2. The cannabidiol has the characteristics of white to faint yellow resin or crystal, has the melting point of 66-67 ℃, is almost insoluble in water, is dissolved in organic solvents such as ethanol, methanol, ether, benzene, chloroform and the like, has the functions of blocking adverse effects of certain polyphenols on human nervous systems, blocking breast cancer metastasis, treating epilepsy, resisting rheumatoid arthritis, resisting insomnia, diminishing inflammation, relieving pain, resisting bacteria and a series of physiological activities, and has a good effect on treating multiple sclerosis.
In order to fully utilize the characteristics of the cannabidiol, a plurality of products are developed aiming at the cannabidiol in the industry, but the cannabidiol is difficult to dissolve in water and is difficult to be absorbed by human bodies, so that the cannabidiol is limited in use. In order to be absorbed by human bodies, water-soluble cannabidiol needs to be developed, most of the existing water-soluble cannabidiol is produced by adopting an inclusion technology, the technology has the defects of low solubility in water, low inclusion rate and yield of the inclusion compound, complex inclusion process and the like, and aiming at the problems, a novel preparation process of the water-soluble cannabidiol is needed in the industry so as to solve the problems in the industry.
The invention content is as follows:
the technical problem to be solved by the invention is as follows: provides a preparation process of water-soluble cannabidiol to solve the problems in the industry.
In order to solve the technical problems, the invention is realized by the following technical scheme: a preparation process of water-soluble cannabidiol comprises the following steps:
(1) placing the cannabidiol raw material into a first ethanol solution to be mixed to form a first mixture, and placing the first mixture in an environment with the temperature of 15-30 ℃ to be stirred for 10 min;
(2) after the cannabidiol raw material in the first mixture is completely dissolved, adding L-arginine into the first mixture and stirring for 5min to form a second mixture;
(3) adding 4-dimethylaminopyridine and dicyclohexylcarbodiimide into the second mixture to carry out chemical reaction for 1-2 h;
(4) monitoring the reaction condition by a TLC point plate, after the cannabidiol raw material disappears and the raw material point is not formed, quickly filtering the second mixture to form a first filtrate, and filtering and removing dicyclohexylurea generated in the reaction process by quick filtration;
(5) then adding a 5% hydrochloric acid ice water solution into the first filtrate and stirring for 10min to form a third mixture;
(6) then vacuum concentrating the third mixture to obtain cannabidiol arginine ester crude product;
(7) dissolving the crude cannabidiol arginine ester in a second ethanol solution, stirring to form a fourth mixture, concentrating the fourth mixture until granular substances are separated out, and stopping concentrating to form a concentrate;
(8) and placing the concentrate in an environment of-20 ℃ for standing and crystallization to obtain the water-soluble cannabidiol.
Preferably, the cannabidiol feedstock is mixed with the first ethanol solution in a ratio of 1 g: mixing at a ratio of 15 ml-20 ml.
Preferably, the cannabidiol raw material and the L-arginine are mixed in a molar ratio of 1: 2-2.2.
Preferably, the cannabidiol starting material is mixed with the 4-dimethylaminopyridine in an amount of 1 g: 10-30mg, wherein the cannabidiol raw material and the dicyclohexylcarbodiimide are mixed according to the proportion of 1 g: 0.3-0.7g of raw materials.
Preferably, the temperature of the hydrochloric acid ice water solution is 0-5 ℃.
Preferably, the cannabidiol arginine esterified ester crude product and the second ethanol solution are mixed according to the proportion of 1 g: 20-40 ml.
Preferably, the content of cannabidiol in the cannabidiol raw material is greater than or equal to 98%.
Compared with the prior art, the invention has the advantages that: the water-soluble cannabidiol is prepared by mixing, reacting and concentrating cannabidiol raw materials with the cannabidiol content of more than or equal to 98% for multiple times by using related reagents, so that the traditional method for producing by adopting an inclusion technology is replaced, the production efficiency is improved, and the complexity of the preparation process is reduced.
Description of the drawings:
the invention is further described below with reference to the accompanying drawings.
FIG. 1 is a process flow diagram of the present invention.
In the figure: cannabidiol raw material 1; a first ethanol solution 2; a first mixture 3; l-arginine 4; a second mixture 5; 4-dimethylaminopyridine 6; dicyclohexylcarbodiimide 7; a first filtrate 8; hydrochloric acid ice water solution 9; a third mixture 10; cannabidiol arginine ester crude 11; a second ethanol solution 12; a fourth mixture 13; a concentrate 14; water soluble cannabidiol 15.
The specific implementation mode is as follows:
the invention is described in detail below with reference to the following figures and embodiments:
example 1:
(1) weighing 100g of cannabidiol raw material 1 with cannabidiol content of 98%, and mixing the cannabidiol raw material 1 and the first ethanol solution 2 according to the ratio of 1 g: weighing 1500ml of first ethanol solution 2 according to the proportion of 15ml to 20ml, then placing the cannabidiol raw material 1 into the first ethanol solution 2 to mix to form a first mixture 3, and simultaneously placing the first mixture 3 in an environment at 15 ℃ to stir for 10 min;
(2) after the cannabidiol raw material 1 in the first mixture 3 is completely dissolved, adding L-arginine 4 into the first mixture 3 and stirring for 5min to form a second mixture 5; cannabidiol raw material 1 and L-arginine 4 are mixed according to a molar ratio of 1: 2-2.2; simultaneously adding 1000mg of 4-dimethylaminopyridine 6 and 30g of dicyclohexylcarbodiimide 7 into the second mixture 5, and carrying out a chemical reaction for 1.5 h;
(3) monitoring the reaction condition by a TLC point plate, after the cannabidiol raw material 1 disappears and the raw material point is not formed, quickly filtering the second mixture 5 to form a first filtrate 8, and filtering and removing dicyclohexylurea generated in the reaction process by quick filtration;
(4) then adding 5% of hydrochloric acid ice water solution 9 into the first filtrate 8, stirring for 10min to form a third mixture 10, wherein the hydrochloric acid ice water solution 9 is 0 ℃, and then carrying out vacuum concentration on the third mixture 10 to obtain a cannabidiol arginine esterified ester crude product 11;
(5) dissolving the crude cannabidiol arginine ester 11 in a second ethanol solution 12 and stirring to form a fourth mixture 13, wherein the crude cannabidiol arginine ester 11 and the second ethanol solution 12 are mixed according to a ratio of 1 g: proportioning 20ml, concentrating the fourth mixture 13 until granular substances are separated out, and stopping concentrating to form a concentrate 14; and standing the concentrate 14 at-20 ℃ for crystallization to obtain the water-soluble cannabidiol 15.
Example 2:
(1) and weighing 500g of cannabidiol raw material 1 with cannabidiol content of 99%, wherein the weight ratio of the cannabidiol raw material 1 to the first ethanol solution 2 is 1 g: weighing 10000ml of first ethanol solution 2 according to the proportion of 15ml to 20ml, then placing the cannabidiol raw material 1 into the first ethanol solution 2 to mix to form a first mixture 3, and simultaneously placing the first mixture 3 in an environment of 30 ℃ to stir for 10 min;
(2) after the cannabidiol raw material 1 in the first mixture 3 is completely dissolved, adding L-arginine 4 into the first mixture 3 and stirring for 5min to form a second mixture 5; cannabidiol raw material 1 and L-arginine 4 are mixed according to a molar ratio of 1: 2-2.2; simultaneously adding 5000mg of 4-dimethylaminopyridine 6 and 350g of dicyclohexylcarbodiimide 7 into the second mixture 5 to carry out chemical reaction for 2 hours;
(3) monitoring the reaction condition by a TLC point plate, after the cannabidiol raw material 1 disappears and the raw material point is not formed, quickly filtering the second mixture 5 to form a first filtrate 8, and filtering and removing dicyclohexylurea generated in the reaction process by quick filtration;
(4) then adding 5% of hydrochloric acid ice water solution 9 into the first filtrate 8, stirring for 10min to form a third mixture 10, wherein the hydrochloric acid ice water solution 9 is at 3 ℃, and then carrying out vacuum concentration on the third mixture 10 to obtain a cannabidiol arginine esterified ester crude product 11;
(5) dissolving the crude cannabidiol arginine ester 11 in a second ethanol solution 12 and stirring to form a fourth mixture 13, wherein the crude cannabidiol arginine ester 11 and the second ethanol solution 12 are mixed according to a ratio of 1 g: proportioning 20ml, concentrating the fourth mixture 13 until granular substances are separated out, and stopping concentrating to form a concentrate 14; and standing the concentrate 14 at-20 ℃ for crystallization to obtain the water-soluble cannabidiol 15.
It is to be emphasized that: the above embodiments are only preferred embodiments of the present invention, and are not intended to limit the present invention in any way, and all simple modifications, equivalent changes and modifications made to the above embodiments according to the technical spirit of the present invention are within the scope of the technical solution of the present invention.
Claims (7)
1. The preparation process of the water-soluble cannabidiol is characterized by comprising the following steps:
(1) placing the cannabidiol raw material (1) into a first ethanol solution (2) to be mixed to form a first mixture (3), and placing the first mixture (3) in an environment with the temperature of 15-30 ℃ to be stirred for 10 min;
(2) after the cannabidiol raw material (1) in the first mixture (3) is completely dissolved, adding L-arginine (4) into the first mixture (3) and stirring for 5min to form a second mixture (5);
(3) adding 4-dimethylaminopyridine (6) and dicyclohexylcarbodiimide (7) into the second mixture (5) to carry out a chemical reaction for 1-2 h;
(4) monitoring the reaction condition by a TLC point plate, after the cannabidiol raw material (1) disappears and the raw material point is not formed, quickly filtering the second mixture (5) to form a first filtrate (8), and filtering out dicyclohexylurea generated in the reaction process by quick filtration;
(5) then adding 5% hydrochloric acid ice water solution (9) into the first filtrate (8) and stirring for 10min to form a third mixture (10);
(6) then, the third mixture (10) is concentrated in vacuum to obtain a cannabidiol arginine ester crude product (11);
(7) dissolving the cannabidiol arginine ester crude product (11) in a second ethanol solution (12) and stirring to form a fourth mixture (13), then concentrating the fourth mixture (13) until granular substances are precipitated, and stopping concentrating to form a concentrate (14);
(8) and standing the concentrate (14) at-20 ℃ for crystallization to obtain the water-soluble cannabidiol (15).
2. The process of claim 1 for the preparation of water soluble cannabidiol, wherein: the cannabidiol feedstock (1) and the first ethanol solution (2) are mixed in a ratio of 1 g: mixing at a ratio of 15 ml-20 ml.
3. The process of claim 1 for the preparation of water soluble cannabidiol, wherein: the cannabidiol raw material (1) and the L-arginine (4) are mixed according to a molar ratio of 1: 2-2.2.
4. The process of claim 1 for the preparation of water soluble cannabidiol, wherein: the cannabidiol raw material (1) and the 4-dimethylaminopyridine (6) are mixed according to a ratio of 1 g: 10-30mg, wherein the cannabidiol raw material (1) and the dicyclohexylcarbodiimide (7) are mixed according to the proportion of 1 g: 0.3-0.7g of raw materials.
5. The process of claim 1 for the preparation of water soluble cannabidiol, wherein: the temperature of the hydrochloric acid ice water solution (9) is 0-5 ℃.
6. The process of claim 1 for the preparation of water soluble cannabidiol, wherein: the cannabidiol arginine esterified crude product (11) and the second ethanol solution (12) are mixed according to the proportion of 1 g: 20-40 ml.
7. The process of claim 1 for the preparation of water soluble cannabidiol, wherein: the content of the cannabidiol in the cannabidiol raw material (1) is more than or equal to 98%.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880754A (en) * | 2012-12-21 | 2014-06-25 | 西藏海思科药业集团股份有限公司 | Alkaline amino acid ester salt of propofol |
| CN106632726A (en) * | 2015-10-29 | 2017-05-10 | 天津工业大学 | A method of grafting arginine to chitosan |
| CN107951869A (en) * | 2016-10-14 | 2018-04-24 | 汉义生物科技（北京）有限公司 | Pharmaceutical preparation and its application containing cannabidiol |
| US20180271826A1 (en) * | 2017-03-22 | 2018-09-27 | Colorado Can Llc | Dry powders of cannabinoids and methods for preparing dry powders |
| CN110179862A (en) * | 2019-06-26 | 2019-08-30 | 云南绿新生物药业有限公司 | A kind of preparation method of water solubility cannabidiol inclusion compound (Nano capsule) |
-
2020
- 2020-04-14 CN CN202010291798.5A patent/CN111574333A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880754A (en) * | 2012-12-21 | 2014-06-25 | 西藏海思科药业集团股份有限公司 | Alkaline amino acid ester salt of propofol |
| CN106632726A (en) * | 2015-10-29 | 2017-05-10 | 天津工业大学 | A method of grafting arginine to chitosan |
| CN107951869A (en) * | 2016-10-14 | 2018-04-24 | 汉义生物科技（北京）有限公司 | Pharmaceutical preparation and its application containing cannabidiol |
| US20180271826A1 (en) * | 2017-03-22 | 2018-09-27 | Colorado Can Llc | Dry powders of cannabinoids and methods for preparing dry powders |
| CN110179862A (en) * | 2019-06-26 | 2019-08-30 | 云南绿新生物药业有限公司 | A kind of preparation method of water solubility cannabidiol inclusion compound (Nano capsule) |
Non-Patent Citations (2)
| Title |
|---|
| 国家医药管理局医药工业情报中心站，国际医药服务公司编: "《世界药物指南》", 31 January 1990, 上海医科大学出版社 * |
| 黎建宏编著: "《新编药物手册》", 31 October 2005, 江西科学技术出版社 * |
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