CN105997985A - Application of marihuana extract in preparation of gout treating medicine - Google Patents
Application of marihuana extract in preparation of gout treating medicine Download PDFInfo
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- CN105997985A CN105997985A CN201610415332.5A CN201610415332A CN105997985A CN 105997985 A CN105997985 A CN 105997985A CN 201610415332 A CN201610415332 A CN 201610415332A CN 105997985 A CN105997985 A CN 105997985A
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- fructus cannabis
- extract
- gout
- preparation
- cannabis extract
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- 201000005569 Gout Diseases 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 235000005607 chanvre indien Nutrition 0.000 title abstract 4
- 244000261228 chanvre indien Species 0.000 title abstract 4
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims abstract description 31
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229940116269 uric acid Drugs 0.000 claims abstract description 28
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 claims abstract description 21
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 claims abstract description 21
- 229960004242 dronabinol Drugs 0.000 claims abstract description 21
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 claims abstract description 19
- QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 claims abstract description 18
- 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 claims abstract description 18
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses application of a marihuana extract in preparation of gout treating medicine. Inventors find that tetrahydrocannabinol and cannabidiol have the quite strong gout resisting effect after being mixed according to the specific ratio for the first time, the hyperuricemia mouse serum uric acid level can be remarkably lowered, no obvious influence is produced to the normal mouse serum uric acid level, toe swelling induced by sodium urate can be remarkably restrained, activity is similar to that of allopurinol, and the toxic and side effect is small. The marihuana extract has the obvious gout treating and preventing effect. The invention further provides a gout treating medicinal preparation of the marihuana extract and a corresponding dosage form thereof. Various kinds of medicine with different dosage forms can be used clinically through a conventional preparation method, and use is convenient.
Description
Technical field
The present invention relates to Fructus Cannabis new application in medical science, concretely relate to a kind of Fructus Cannabis extract and exist
Application in preparation treatment gout medicine.
Background technology
Goat is the class disease that internal purine metabolic disturbance causes, and purine becomes through a series of metabolism
Changing, the product ultimately formed is uric acid.Uric acid does not has any physiological function in human body, in normal condition
Under, the uric acid 2/3 of internal generation is discharged by kidney, and 1/3 is discharged by large intestine.Internal uric acid be
Constantly generating and drain, therefore it maintains certain concentration in blood.Synthesis and decomposition at purine
During, there is the participation of multiple enzyme, owing to the birth defect metabolism of enzyme gets muddled, make the conjunction of uric acid
Become to increase or discharge and reduce, all can cause hyperuricemia.When serum Uric Acid Concentration is too high, uric acid i.e. with
The form of sodium salt is deposited in joint, soft tissue, cartilage and kidney, causes the foreign body inflammatory reaction of tissue
Become to cause the seed of trouble of gout.As treatment the most thoroughly can cause arthroncus, deformity, stiff, periarticular
Ecchymosis, tuberosity, concurrent gouty renal calculus, gouty renal failure, gouty coronary heart disease, high blood
The internal organs diseases such as fat, hypertension, urinary system calculus threaten the life of patient directly to cause the termination of life.
Along with our people's growth in the living standard, life-time dilatation, dietary structure change (rich in core
The food of albumen increases), the increase of overweight people, and the attention degree reinforcement etc. to primary disease, gout is
Being no longer the rare disease of compatriots, its prevalence relatively increased about 15～30 times before 15 years.During gout is apt to occur in
In elderly men, but the sickness rate of middle and aged women and young man has risen at present.Morbidity year
Age is many more than 50 years old (63%)；In gerontal patient, women sickness rate is higher than male, and sickness rate
29% after 60 years old is improved by 60 years old front 7%.The up-to-date report of CDC shows
Showing, the sickness rate of China's gout surpasses the world average level, and whole nation patient with gout is more than seven million people, entirely
Ball goat patient is up to 1.3 hundred million.
The current kind of antigout drug is few, clinical treatment mainly with colchicine, nonsteroidal antiinflammatory drug,
Hormone, promotion urate excretion medicine (such as probenecid, sulfinpyrazone and benzbromarone) and suppression uric acid synthetic drug
(such as allopurinol) is main.Acute period of disease is mainly applied drink tazettine, nonsteroidal antiinflammatory drug, is swashed
Element, the catabasis mainly apply promotion urate excretion medicine, suppression uric acid synthetic drug.These medicines are in treatment
The most defective.Weak curative effect, side effect become greatly the bottleneck of its clinical practice, and can not life-time service.
More common Chinese patent medicine preparations treat pain phoenix, but drug effect is relatively low.So being badly in need of at present
Develop and exploitation selectivity is strong, have no side effect, efficiently and gout will not be made to produce after drug withdrawal rebound
Anti-gout novel medical.
Tetrahydrocannabinol (THC) is the major psychoactive material in Fructus Cannabis.2013, American science
Family's research finds, tetrahydrocannabinol maybe can infect anti-AIDS.Tetrahydrocannabinol also has alleviating pain, thorn
Swash appetite, reduce the effect of sense of feeling sick.
Cannabidiol (CBD) is that a kind of nontoxic of extraction from Fructus Cannabis floral leaf can be used for medicine, cosmetic
Product, the aldehydes matter of high added value of health food.At present, the flourishing state such as Israel, the U.S., Britain
Family has done raw material with it and has developed multiple special effect medicine and cosmetics.CBD is non-additive in Fructus Cannabis
Composition, can hinder THC on nerve system of human body affect, and have spasmolytic, resisting rheumatoid arthritis,
The pharmacologically actives such as anxiety, it is known that can serve as treating epilepsy, diabetes, neonatal hypoxic-ischemic brain
The active component of the medicine of the diseases such as disease.
Summary of the invention
It is an object of the invention to provide the new application of Fructus Cannabis, i.e. new opplication in pharmacy.
It practice, the present invention relates to a kind of Fructus Cannabis extract in the medicine of preparation treatment or prevention gout
Application；Described Fructus Cannabis extract is that tetrahydrocannabinol and cannabidiol are according to weight ratio 4 1～1 4
Mixture.
The invention still further relates to the application in preparation fall blood uric acid medicine of the described Fructus Cannabis extract.
The invention still further relates to described Fructus Cannabis extract in preparation treatment or prevention antihyperuricemic disease drug
Application.
In order to be more fully understood that the essence of the present invention, below with pharmacological evaluation and the knot of described Fructus Cannabis extract
Fruit illustrates its new application in pharmaceutical field.
1, prepare Fructus Cannabis extract, but tetrahydrocannabinol used and cannabidiol are not limited to following
Preparation method obtains.
Taking cannabis, leaf, fiber crops bran or three's mixture, after remove impurity, drying, pulverize, CO2 is super to be faced
Extraction, methanol re-dissolved after remove impurity, lysate is Hex after chromatographic column separates, and collects eluent,
Concentrating under reduced pressure, vacuum drying, pulverize, obtain tetrahydrocannabinol.Take cannabis, leaf, fiber crops bran or three to mix
Compound, after remove impurity, drying, pulverize, CO2 is super faces extraction, ethanol re-dissolved after remove impurity, lysate
Pentane eluting after chromatography, collects eluent, concentrating under reduced pressure, vacuum drying, pulverizes, obtain Fructus Cannabis
Diphenol.
Taking tetrahydrocannabinol and cannabidiol mixing, (tetrahydrocannabinol is with big to obtain A Fructus Cannabis extract
The weight ratio of fiber crops diphenol is 4 1), B Fructus Cannabis extract (tetrahydrocannabinol and the weight of cannabidiol
Ratio is 1 1), C Fructus Cannabis extract (weight ratio of tetrahydrocannabinol and cannabidiol is 1 4).
2, Fructus Cannabis extract is taken, standby after diluting with sodium chloride.
3, the Fructus Cannabis extract impact on hyperuricemia mice uric acid is observed with conventional pharmacological testing.
(1) choose body weight 18～22g Kunming mouse 60, male and female half and half, be randomly divided into 6 groups,
Often group 10, i.e. Normal group, model group, positive drug allopurinol tablet (40mg/kg) group, Fructus Cannabis carries
Take thing A, B, C group (20mg/kg).Gastric infusion, 1 time/d, Normal group and model group gavage
Give to wait capacity distilled water, continuous 12d.Last is administered 1h pneumoretroperitoneum injection hypoxanthine 10mg/kg,
After 1h, eyeball takes blood, and 3000r/min is centrifuged 10min, takes supernatant and surveys serum uric acid.
Test result indicate that, compare with Normal group, model group mice serum uric acid content is significantly raised,
There are significant difference (P ＜ 0.05), prompting modeling success.After giving Fructus Cannabis extract, with model group ratio
Relatively, Fructus Cannabis extract A, B, C group all can significantly reduce mice serum uric acid content, and difference has significantly
Property (P ＜ 0.05～0.01)；Compare with other purine sheet group, Fructus Cannabis extract A, B, C group fall Mouse Blood
Clear uric acid content effect is all better than other purine sheet group, and difference has significance (P ＜ 0.05).Prompting, greatly
Nettle extract significantly reduces effect to the Mouse Blood uric acid caused by hypoxanthine, and effect is better than other purine
Sheet.The results are shown in Table 1.
The impact of the hyperuricemia mice uric acid that hypoxanthine is induced by table 1 Fructus Cannabis extract
| Group | Dosage (mg/Kg) | Serum uric acid concentration (mg/L) |
| Normal control sample | Equal-volume distilled water | 132.12±46.36 |
| Model comparison sample | Equal-volume distilled water | 200.04±46.62△ |
| Allopurinol tablet group | 40 | 157.48±36.07* |
| Fructus Cannabis extract A group | 20 | 116.45±36.13**# |
| Fructus Cannabis extract B group | 20 | 111.02±40.01**# |
| Fructus Cannabis extract C group | 20 | 126.46±38.19*# |
Note: compare with normal control sample,△P ＜ 0.05, compares with model group, * P ＜ 0.05, * * P ＜ 0.01, and allopurinol tablet group, than
Relatively#P ＜ 0.05.
(2) Fructus Cannabis extract impact on the acid of normal mouse retention
Choose body weight 18～22g Kunming mouse 40, male and female half and half, be randomly divided into 4 groups, often group
10, i.e. Normal group, Fructus Cannabis extract A, B, C group (20mg/kg).Gastric infusion, 1 time
/ d, Normal group and model group gavage such as give at capacity distilled water, the continuous 12d.Last is administered 1h
Eyeball takes blood, and 3000r/min is centrifuged 10min, takes supernatant and surveys serum uric acid.
Test result indicate that, compare with Normal group, after giving Fructus Cannabis extract, each dosage group is to little
The equal zero difference of Mus serum uric acid (P ＞ 0.05).Prompting, Fructus Cannabis extract is to normal Mouse Blood uric acid
Do not make significant difference.The results are shown in Table 2.
The impact on the acid of normal mouse retention of table 2 Fructus Cannabis extract
| Group | Dosage (mg/Kg) | Serum uric acid concentration (mg/L) |
| Normal control sample | Equal-volume distilled water | 132.12±46.36 |
| Fructus Cannabis extract A group | 20 | 145.85±24.20 |
| Fructus Cannabis extract B group | 20 | 138.73±27.19 |
| Fructus Cannabis extract C group | 20 | 127.28±26.55 |
(3) Fructus Cannabis extract causes the impact of rat paw edema to micro-crystal type Monosodium urate crystallization (MSU)
The preparation of MSU: put by 5g uric acid in 1000mL boiling water, adjusts pH to 7.4, heating with NaOH
To 95 DEG C.Put room temperature condition to cool down and be gently mixed, filter and i.e. obtain MSU, MSU is placed in 200 DEG C high
Temperature sterilizing, faces the suspension that the used time is made into 100mg/mL with physiological saline solution standby.
Choose body weight 180～220gWistar male rat 60, be randomly divided into 6 groups, often group 10,
I.e. Normal group, model group, positive drug allopurinol tablet group (40mg/kg), Fructus Cannabis extract A, B, C
Group (20mg/kg).Gastric infusion, 1 time/d, Normal group and model group gavage such as give at the capacity distillation
Water, continuous 15d.After last is administered 1h, in Rat Right metapedes plantar subcutaneous injection 0.15mLMSU (100mg/mL)
Cause inflammation, before and after causing inflammation, measure right metapedes sole of the foot Zhou Jing.Observe and measure injection after 1h, 2h, 3h,
Pedal swelling situation and Zhou Jing thereof after 5h, 7h Rat Right the most in the same time, calculate its swelling.Pedal swelling
Degree=(t time Zhou Jing-t0Time Zhou Jing)/t0Time Zhou Jing × 100%.
Result shows, compares with Normal group, and model group rats swelling degree of the paw is significantly raised, has aobvious
Write sex differernce (P ＜ 0.01), prompting modeling success.Fructus Cannabis extract compares with model group, the equal energy of each group
Significantly inhibiting rat paw edema, difference has significance (P ＜ 0.05, P ＜ 0.01), with other purine
Sheet group compares, and Fructus Cannabis extract group suppression rat paw edema is better than other purine sheet group, and difference has significantly
Property (P ＜ 0.05).Prompting, the degree of rat paw edema caused by MSU is had significantly by Fructus Cannabis extract
Inhibitory action, effect is better than other purine sheet.The results are shown in Table 3.
The impact on rat paw edema rate of table 3 Fructus Cannabis extract
Note: compare with normal control sample,△△P ＜ 0.05, compares with model group, * P ＜ 0.05, * * P ＜ 0.01, with allopurinol tablet group, compares#P
＜ 0.05.
The invention provides with described Fructus Cannabis extract as active component, for treating the medicine system of gout
Agent.This pharmaceutical preparation is with described Fructus Cannabis extract for effective active composition, and includes and can connect on pharmaceutics
Other adjuvant components being subject to.Described pharmaceutical preparation includes oral agents and injection, and wherein oral agents includes glue
Wafer, oral liquid, tablet, drop pill, granule etc., injection type includes injection dosage form and injection
Freeze-dried powder dosage form etc..When preparing oral formulations, available auxiliary type agent can be starch, dextrin or ring
The conventional filler such as dextrin, sucrose, stearate.Lyophilized injectable powder can pass through aseptic spray drying,
Prepared by the method such as low-temperature vacuum drying, lyophilization.The later stage preparation technology of each preparation and equipment all belong to system
The routine techniques in medicine field, this is not construed as limiting by the present invention, therefore not describes in detail at this.
Could be aware that from result above, it is an advantage of the current invention that:
1, known compound tetrahydrocannabinol and cannabidiol have been excavated new medical application by the present invention,
Open up a new application.
2, prove that tetrahydrocannabinol and cannabidiol have very after mixing in specific proportions by serial experiment
Strong gout effect, can significantly reduce hyperuricemia mice serum uric acid level, to normal Mouse Blood
Clear uric acid level does not makes significant difference, and can significantly inhibit the toes swelling induced by Monosodium urate, active and the most fast
Purine alcohol is suitable, and toxic and side effects is little.The Fructus Cannabis extract of the present invention has obvious treatment and prevention gout
Effect.
3, the Fructus Cannabis extract safety non-toxic of the present invention, pharmacological action is strong, imply that the most medicinal before
Scape.
4, the present invention products material abundance, inexpensive, have no toxic and side effects, preparation technology is simple,
And peroral dosage form, injection type, tablet etc. can be made, easy to use, injection can make intramuscular injection and
Intravenous injection.
Detailed description of the invention
Below by embodiment, the present invention is described in further detail, but embodiment is not to this
The restriction of bright technical scheme.
Embodiment 1
Taking cannabis, leaf, fiber crops bran three's mixture, after remove impurity, drying, pulverize, CO2 is super faces extraction
Taking, methanol re-dissolved after remove impurity, lysate is Hex after chromatographic column separates, and collects eluent, subtracts
Pressure concentrates, vacuum drying, pulverizes, obtains tetrahydrocannabinol.Take cannabis, leaf, through remove impurity, drying,
After pulverizing, CO2 is super faces extraction, ethanol re-dissolved after remove impurity, and lysate is pentane eluting after chromatography,
Collect eluent, concentrating under reduced pressure, vacuum drying, pulverize, obtain cannabidiol.
According to weight ratio 4 1～1 4 mixing, tetrahydrocannabinol and cannabidiol are made required Fructus Cannabis carry
Take thing.
Take Fructus Cannabis extract 100 grams (crossing 80 mesh sieves), add 60 grams of microcrystalline Cellulose, cross 80 mesh sieves
Three times, mix homogeneously, spray into 95% ethanol solution, soft material processed, cross 40 mesh sieves and pelletize, 60 DEG C are dried
Half an hour, it is sub-packed in 3# capsule, aluminium plastic composite packaging, makes capsule.
Embodiment 2
Taking cannabis, leaf, after remove impurity, drying, pulverize, CO2 is super faces extraction, and after remove impurity, methanol is again
Dissolving, lysate is Hex after chromatographic column separates, and collects eluent, concentrating under reduced pressure, is vacuum dried,
Pulverize, obtain tetrahydrocannabinol.Take cannabis, leaf, the mixture of fiber crops bran, through remove impurity, dry, pulverize
After, CO2 is super faces extraction, ethanol re-dissolved after remove impurity, and lysate is pentane eluting after chromatography, receives
Collection eluent, concentrating under reduced pressure, vacuum drying, pulverize, obtain cannabidiol.
According to weight ratio 4 1～1 4 mixing, tetrahydrocannabinol and cannabidiol are made required Fructus Cannabis carry
Take thing.
Take Fructus Cannabis extract powder, admixture doses 5～the dried starch of 20% and 1～the magnesium stearate of 5%,
Blended, pelletize, be dried, tabletting, prepare tablet.
Embodiment 3
Repeat embodiment 2, have following difference: take Fructus Cannabis extract powder, add sucrose water and routine
The preservative of amount, the adjuvant such as stabilizer.Filtration, sterilizing, be distributed in 10mL bottle, make oral liquid.
Embodiment 4
Repeat embodiment 2, have following difference: take Fructus Cannabis extract powder, add water for injection and dissolve,
Add 2.0 ‰ activated carbons, stirring, filter, continue with 0.45 μm, 0.22 μm microporous filter membrane classification
Filter, supplements water for injection, is sub-packed in cillin bottle, lyophilization, recharges high-purity nitrogen, jump a queue,
Gland, packaging, make injection.
Claims (3)
1. Fructus Cannabis extract application in the medicine of preparation treatment or prevention gout, described Fructus Cannabis carries
Taking thing is tetrahydrocannabinol and the cannabidiol mixture according to weight ratio 4 1～1 4.
2. Fructus Cannabis extract application in preparation fall blood uric acid medicine, described Fructus Cannabis extract is four
Hydrogen cannabinol and cannabidiol are according to the mixture of weight ratio 4 1～1 4.
3. Fructus Cannabis extract application in preparation treatment or prevention antihyperuricemic disease drug, described is big
Nettle extract is tetrahydrocannabinol and the cannabidiol mixture according to weight ratio 4 1～1 4.
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| CN109996551A (en) * | 2016-09-29 | 2019-07-09 | 耶路撒冷希伯来大学伊森姆研究发展有限公司 | The method of selective extraction cannboid from plant source |
| CN110064030A (en) * | 2019-05-30 | 2019-07-30 | 厦门梓素生物科技有限公司 | One kind extract for treating gouty arthritis medicinal application of CBD containing cannabidiol |
| US11040932B2 (en) | 2018-10-10 | 2021-06-22 | Treehouse Biotech, Inc. | Synthesis of cannabigerol |
| US11084770B2 (en) | 2016-12-07 | 2021-08-10 | Treehouse Biotech, Inc. | Cannabis extracts |
| US11202771B2 (en) | 2018-01-31 | 2021-12-21 | Treehouse Biotech, Inc. | Hemp powder |
| US11224628B2 (en) | 2016-09-29 | 2022-01-18 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Method for extraction of an agent from a plant source |
| US11819490B2 (en) | 2016-09-29 | 2023-11-21 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Dilutable formulations of cannabinoids and processes for their preparation |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109996551A (en) * | 2016-09-29 | 2019-07-09 | 耶路撒冷希伯来大学伊森姆研究发展有限公司 | The method of selective extraction cannboid from plant source |
| US11224628B2 (en) | 2016-09-29 | 2022-01-18 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Method for extraction of an agent from a plant source |
| US11666618B2 (en) | 2016-09-29 | 2023-06-06 | Yissun Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Method for selective extraction of cannabinoids from a plant source |
| US11819490B2 (en) | 2016-09-29 | 2023-11-21 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Dilutable formulations of cannabinoids and processes for their preparation |
| US11819491B2 (en) | 2016-09-29 | 2023-11-21 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Dilutable formulations of cannabinoids and processes for their preparation |
| US11084770B2 (en) | 2016-12-07 | 2021-08-10 | Treehouse Biotech, Inc. | Cannabis extracts |
| US11202771B2 (en) | 2018-01-31 | 2021-12-21 | Treehouse Biotech, Inc. | Hemp powder |
| US11040932B2 (en) | 2018-10-10 | 2021-06-22 | Treehouse Biotech, Inc. | Synthesis of cannabigerol |
| CN110064030A (en) * | 2019-05-30 | 2019-07-30 | 厦门梓素生物科技有限公司 | One kind extract for treating gouty arthritis medicinal application of CBD containing cannabidiol |
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