EP3356007A1 - Distillation sous vide pour l'enrichissement de cannabidiol - Google Patents

Distillation sous vide pour l'enrichissement de cannabidiol

Info

Publication number
EP3356007A1
EP3356007A1 EP16788443.6A EP16788443A EP3356007A1 EP 3356007 A1 EP3356007 A1 EP 3356007A1 EP 16788443 A EP16788443 A EP 16788443A EP 3356007 A1 EP3356007 A1 EP 3356007A1
Authority
EP
European Patent Office
Prior art keywords
cannabidiol
cbd
vacuum distillation
plant material
cannabis plant
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP16788443.6A
Other languages
German (de)
English (en)
Inventor
Andreas Rutz
Michael Englert
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SPECTRUM THERAPEUTICS GMBH
Original Assignee
Bionorica Ethics GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bionorica Ethics GmbH filed Critical Bionorica Ethics GmbH
Publication of EP3356007A1 publication Critical patent/EP3356007A1/fr
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D1/00—Evaporating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D1/00—Evaporating
    • B01D1/22—Evaporating by bringing a thin layer of the liquid into contact with a heated surface
    • B01D1/222—In rotating vessels; vessels with movable parts
    • B01D1/223—In rotating vessels; vessels with movable parts containing a rotor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/12—Molecular distillation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings

Definitions

  • the present invention relates to a method for
  • the invention further relates to a
  • Cannabidiol extract and the use of a preserved
  • Cannabidiol extract in pharmacy and cosmetics are examples of Cannabidiol extract in pharmacy and cosmetics.
  • Cannabis (hemp) belongs together with the genus Humulus
  • Humulus does not contain cannabinoids. Within the genus Cannabis is a botanical and chemotaxonomic
  • cannabis is divided into a drug and fiber hemp, the distinction due to the
  • CBD cannabidiol
  • a 9 -tetrahydrocannabinol A 9 -THC
  • Fiber hemp also: hemp, industrial hemp
  • a 9 -THC content 0.2% (eg Germany, etc.)
  • type of drug A 9 -THC content of about 5-15% (marijuana, hashish).
  • Cannabis sativa L. contains over 400 different ingredients, of which more than 60 belong to the class of cannabinoids. The most important cannabinoids are below
  • Cannabigerol-like (CBG) cannabigerol ((E) -CBG-Cs),
  • Cannabigerol monomethyl ether (E) -CBGM-Cs A), cannabinerolic acid A ((Z) -CBGA-Cs A), cannabigerovarin ((E) -CBGV-C 3 ),
  • Cannabigerolic Acid A ((E) -CBGA-Cs A), Cannabigerolic Acid A
  • CBD-C5 cannabidiol (CBD-C5), cannabidiol monomethyl ether (CBDM-C5), cannabidiol C4 (CBD-C 4 ),
  • Cannabidivarin CBDV-C3
  • CBD-Ci cannabidiorcol
  • Cannabidiolic acid CBDA-C5
  • CBDVA-C3 cannabidivaric acid
  • Cannabinodiol-like (CBND) Cannabinodiol (CBND-C5),
  • Cannabinodivarin (CBND-C3)
  • Tetrahydrocannabinol-like (THC) A9-tetrahydrocannabinol (A9-THC-C 5), A9-tetrahydrocannabinol-C4 (A9-THC-C 4), ⁇ 9- tetrahydrocannabivarin (THCV A9-C3), A9-Tetrahydrocannabiorcol (A9 THCO-Ci), A9-tetrahydrocannabinoleic acid (A9-THCA-C 5 A), ⁇ 9-tetrahydrocannabinolic acid B (A9-THCA-C 5 B), ⁇ 9-tetrahydrocannabinol-C4 (A9-THCA-C 4 A and / or B) , ⁇ 9- Tetrahydrocannabivarinklare A (A9-THCVA-C 3 A), ⁇ 9- Tetrahydrocannabiorcolklad
  • Cannabinol-type (CBN): Cannabinol CBN-C5, C4-cannabinol (CBN C 4), Cannabivarin (CBN-C3), cannabinol C2 (CBN-C2),
  • Cannabiorcol (CBN-Ci), cannabinoic acid A (CBNA-C5 A),
  • Cannabinol methyl ether (CBNM-C5)
  • Cannabitriol-like (CBT) (-) - (9R, 10R) -trans-cannabitriol ((-) -trans-CBT-Cs), (+) - (9S, 10S) -canabitriol ((+) - trans- CBT
  • Cannabidiolic acid A (CBDA-C5 9-OH-CBT-C5 ester), (-) - (6aR, 9S, 10S, 10Ar) -9, 1-O-dihydroxy-hexahydrocannabinol, Cannabiripsol cannabiripsol C5, (-) -6a, 7, 1 Oa-trihydroxy-A9-tetrahydrocannabinol ((-) -canabitetrol), 10-oxo-A6a (1 Oa) tetrahydrocannabinol (OTHC);
  • Cannabiglendol C3 (OH-iso-HHCV-C3), dehydrocannabifuran (DCBF)
  • Isocannabinoids (-) -A7 trans- (1R, 3R, 6R) -
  • Cannabicite-like (CEE) cannabicite (CBT-C5);
  • Cannabichromanone-like (CBCN) cannabichromanone (CBCN-C5), cannabichromanone-C3 (CBCN-C3), cannabicoumaronone (CBCON-C5).
  • cannabinoids can be found their associated carboxylic acids in the crude drug. These carboxylic acids are biosynthetic precursors.
  • Cannabis preparations have a variety of therapeutic effects, including anti-spastic, analgesic,
  • MS multiple sclerosis
  • Stativex sublingual spray
  • CBD Cannabidiol
  • Cannabinoid receptor agonist Cannabinoid receptor agonist
  • Fig. 1 CBD (structural formula)
  • CBD can be prepared synthetically (Michoulam R, Shvo Y., Hashish I. The structure of cannabidiol, Tetrahedron 1963, 19 (12), 2073).
  • the invention relates to a method for extracting cannabidiol from cannabis plant material, wherein a
  • vacuum distillation means that the distillation takes place in vacuo at 0.001 to 50 mbar, preferably 0.001 to 10 mbar, more preferably 0.001 to 1 mbar, in the so-called fine vacuum range, Furthermore, it is preferred that the temperature is 120 to 240 degrees Celsius is, in particular 150 to 230 degrees
  • Short path distillation in the sense of this invention means that the gas phase has to cover only a very short path between the original and the condenser in the fine vacuum applied, for example, a short path evaporator can be used, which is structurally a conventional one
  • Thin-film evaporator corresponds, but the capacitor is integrated into the interior of the evaporator cylinder, so that the way the vapors must travel to the condenser is very short and pressures of 0.001 mbar can be achieved. Also included according to the invention is a method according to the invention by means of a thin-film evaporator or
  • evaporator in the sense of this invention comprises an im
  • a common structural feature of thin film evaporator and falling film evaporator is at least one heated, planar evaporation element, on which a thin layer of the liquid primary extract is applied and partially evaporated (ULLMANN: Billet, Reinhard: Evaporation,
  • a short path evaporator or a thin film evaporator is preferred.
  • Separation columns are e.g. available from VTA Maschinenstechnische Anlagen GmbH & Co. KG, Niederwinkling (DE).
  • the length of the column is
  • the vacuum distillation can be coupled with a column distillation.
  • Invention is also a column distillation
  • the rectification allows the safe separation of THC and enrichment of CBD to more than 80%.
  • the temperature is 120 to 240 degrees Celsius, in particular 150 to 230 degrees Celsius.
  • the pressure is up to 5 - 10 mbar and the temperature 200 to 230 degrees Celsius. This allows safe CBD accumulation to yield a THC-free extract, completely depleting THC. It is further preferred that the vacuum distillation takes place on a first primary extract with at least 15% by weight of CBD.
  • the cannabis plant material is cut, crushed and subjected to a first extraction, for example a CO2 extraction, as described in DE 100 51 427 C1.
  • a first extraction for example a CO2 extraction, as described in DE 100 51 427 C1.
  • an extraction with hexane or a column chromatography can also be carried out, and in this way a primary extract, preferably containing at least 15% by weight of CBD, which is used for further vacuum distillation (supra).
  • CO2 extraction is preferred.
  • Preferred cannabis plant material is fiber, hemp, in particular of the varieties Fedora 17, Feiina 34, Ferimon 12, Futura 75 and others with a relatively high content of CBD in% by weight.
  • the subject of the invention is likewise a cannabidiol-containing extract obtainable according to an inventive
  • the extract is honey-colored, spreadable and of a pleasant odor and has a CBD content of more than 35% by weight, more than 50% by weight, in particular more than 70% by weight in dry weight and is almost THC-free or even absolute THC-free.
  • CBD Cannabidiol
  • the inventive method allows an enrichment of cannabidiol of more than 73%, in particular 75% and 80% or more with advantageous depletion of other cannabinoids, in particular THC.
  • the method according to the invention therefore makes it possible to adjust at least the CBD to THC ratio to 125: 1 and greater in the extract obtained.
  • the method according to the invention therefore makes it possible to adjust at least the CBD to CBN ratio to 384: 1 and greater in the extract obtained.
  • the invention also relates to a cannabidiol-containing extract obtainable according to an inventive
  • a method comprising a CBD: THC ratio of at least 125: 1 and / or a CBD: CBN ratio of at least 384: 1.
  • the low-boiler fraction based on CBD [%] is 6.16 and the high-boiler fraction based on CBD [%] is 4.87. That By means of the method according to the invention, it was advantageously possible to selectively separate off almost all substances which boil before and after the cannabidiol.
  • the invention also relates to a cannabidiol-containing extract obtainable according to an inventive
  • a method comprising a heavy-boiling fraction of less than 5% based on CBD and a low-boiling fraction of less than 7% based on CBD.
  • FIG. 1 shows an HPLC chromatogram of such
  • an exemplary starting composition was used for the process according to the invention as follows, with an initial ratio of about 45: 1:
  • the low-boiler fraction based on CBD [%] is 19.8 and the high-boiler fraction based on CBD [%] is 26.0.
  • the inventive method allows particularly advantageous the significant reduction of the low and high boiler components compared to a starting material used. This leads to an extract with specific properties like one
  • this enriched cannabidiol-containing extract can particularly advantageously be used immediately in formulations such as ointment, cream, gel, lotion (skin milk), paste or, preferably, emulsion.
  • the invention also relates to a pharmaceutical, nutritional supplement or cosmetic containing a cannabidiol-containing extract obtainable after one
  • the drug is indicated for antispasmodic, analgesic, antiemetic, neuroprotective, anti-inflammatory and psychiatric
  • composition or agent in particular a drug (drug)
  • a drug drug
  • Suitable solid or liquid galenic Forms of preparation are, for example, granules, powders, dragees, tablets, (micro) capsules, hard capsules,
  • Solubilizer find use.
  • excipients are magnesium stearate, sodium chloride, magnesium carbonate,
  • Detergents and surfactants may be provided, for example, as described below for a cosmetic composition.
  • Composition is generally understood to be heterogeneous
  • Phases are called.
  • one of the two liquids is dispersed in the form of very fine droplets in the other liquid. If the two liquids are water and oil and oil droplets are finely distributed in water, then it is an oil-in-water emulsion (O / W emulsion).
  • O / W emulsion oil-in-water emulsion
  • the basic character of an O / W emulsion is characterized by the water.
  • W / O emulsion Water-in-oil emulsion
  • W / O emulsion water-in-oil emulsion
  • Basic character here is determined by the oil.
  • mixing systems such as water-in-oil-in-water emulsions (W / O / W emulsion) and oil-in-water-in-oil emulsions (O / W / O emulsions) are known. All mentioned emulsions are suitable according to the invention.
  • the anhydrous systems suitable according to the invention include pure oil preparations such as, for example, skin oils. Also usable pastes containing the preparation of the invention and are characterized in that they consist of the same or similar components as an emulsion, but are substantially free of water. In the context of the present
  • oil phase and lipid phase are used interchangeably.
  • the preparation according to the invention may contain an emulsifier as further constituent.
  • an emulsifier as further constituent.
  • this emulsifier may be an O / W emulsifier.
  • Emulsifiers can be advantageously selected from the group of nonionic, anionic, cationic or amphoteric emulsifiers.
  • nonionic emulsifier various emulsifiers from the groups of partial fatty acid esters, fatty alcohols, sterols, polyethylene glycols, e.g. ethoxylated fatty acids, ethoxylated fatty alcohols and ethoxylated sorbitan esters, sugar emulsifiers, polyglycerol emulsifiers or
  • Silicone emulsifiers find use.
  • anionic emulsifiers various emulsifiers from the groups of soaps z.
  • soaps z For example sodium stearate,
  • Fatty alcohol sulfates, mono-, di- and Trialkylphosphokladreester and their ethoxylates, fatty acid lactate esters, fatty acid citrate esters or fatty acid Citroglycerinester find use.
  • cationic emulsifiers for example, quaternary ammonium compounds with a long-chain aliphatic radical z.
  • B. distearyldimonium chlorides are used as cationic emulsifiers.
  • Emulsifiers from the groups Alkylamininoalkancarbonklaren, betaines, sulfobetaines or imidazoline derivatives find use.
  • Naturally occurring emulsifiers according to the invention are preferred, which include, for example, beeswax, wool wax, lecithin and sterols, among others, which also belong to the
  • Plant protein hydrolysates and their derivatives.
  • substances as additives selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids and / or alkenecarboxylic acids having a chain length of 3 to 30
  • esterols can then be advantageously selected from the group
  • the oil phase can advantageously be selected from the group of branched and unbranched hydrocarbons and waxes, dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and fatty acid triglycerides, namely the triglycerol esters of saturated and / or unsaturated, branched and / or or unbranched alkanecarboxylic acids of a chain length of 8-24 C atoms, in particular 12-18 C atoms.
  • the oil phase can advantageously be selected from the group of branched and unbranched hydrocarbons and waxes, dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and fatty acid triglycerides, namely the triglycerol esters of saturated and / or unsaturated, branched and / or or unbranched alkanecarboxylic acids of a chain length of 8-24 C atoms, in particular 12-18 C atoms.
  • fatty acid triglycerides may be advantageously selected from the group of synthetic,
  • antioxidants and / or free-radical scavengers may additionally be added as auxiliary or additive in the preparations according to the invention.
  • antioxidants are selected from the group of lipophilic systems, for example: natural and synthetic tocopherols,
  • antioxidant plant extracts are hydrophilic and hydrophilic
  • Sulfur compounds sodium hydrogen sulfite, cysteine or ascorbic acid.
  • the cosmetic preparations according to the invention may furthermore contain cosmetic adjuvants, such as
  • Preservatives e.g. Preservatives, bactericides, perfumes, foaming inhibitors, colorants, pigments having a coloring effect, thickeners, surfactants, softening, wetting and / or
  • moisturizing substances or other common ingredients of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers,
  • Electrolytes organic solvents or silicone derivatives.
  • composition according to the invention composed essentially of naturally occurring ingredients, as mentioned above.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé de production, d'extraction et d'enrichissement de cannabidiol, et son utilisation. L'invention concerne également un extrait de cannabidiol et l'utilisation d'un extrait de cannabidiol obtenu dans des applications pharmaceutiques et cosmétiques.
EP16788443.6A 2015-09-30 2016-09-30 Distillation sous vide pour l'enrichissement de cannabidiol Pending EP3356007A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP15187795.8A EP3150264A1 (fr) 2015-09-30 2015-09-30 Distillation sous vide destinee a enrichir le cbd
PCT/EP2016/073527 WO2017055619A1 (fr) 2015-09-30 2016-09-30 Distillation sous vide pour l'enrichissement de cannabidiol

Publications (1)

Publication Number Publication Date
EP3356007A1 true EP3356007A1 (fr) 2018-08-08

Family

ID=54292577

Family Applications (2)

Application Number Title Priority Date Filing Date
EP15187795.8A Withdrawn EP3150264A1 (fr) 2015-09-30 2015-09-30 Distillation sous vide destinee a enrichir le cbd
EP16788443.6A Pending EP3356007A1 (fr) 2015-09-30 2016-09-30 Distillation sous vide pour l'enrichissement de cannabidiol

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP15187795.8A Withdrawn EP3150264A1 (fr) 2015-09-30 2015-09-30 Distillation sous vide destinee a enrichir le cbd

Country Status (9)

Country Link
US (1) US20180282250A1 (fr)
EP (2) EP3150264A1 (fr)
CN (1) CN108290082A (fr)
AU (1) AU2016329526B2 (fr)
CA (1) CA3000295A1 (fr)
EA (1) EA201890883A1 (fr)
HK (1) HK1251197A1 (fr)
IL (1) IL258398A (fr)
WO (1) WO2017055619A1 (fr)

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AU2016329526B2 (en) 2021-08-05
EP3150264A1 (fr) 2017-04-05
IL258398A (en) 2018-05-31
EA201890883A1 (ru) 2019-02-28
HK1251197A1 (zh) 2019-01-25
US20180282250A1 (en) 2018-10-04
CN108290082A (zh) 2018-07-17
WO2017055619A1 (fr) 2017-04-06
CA3000295A1 (fr) 2017-04-06
AU2016329526A1 (en) 2018-04-19

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