CA2472561A1 - Process for the production of dronabinol - Google Patents
Process for the production of dronabinol Download PDFInfo
- Publication number
- CA2472561A1 CA2472561A1 CA002472561A CA2472561A CA2472561A1 CA 2472561 A1 CA2472561 A1 CA 2472561A1 CA 002472561 A CA002472561 A CA 002472561A CA 2472561 A CA2472561 A CA 2472561A CA 2472561 A1 CA2472561 A1 CA 2472561A1
- Authority
- CA
- Canada
- Prior art keywords
- dronabinol
- cannabidiol
- solvent
- syringe
- active ingredients
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0078—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a nebulizer such as a jet nebulizer, ultrasonic nebulizer, e.g. in the form of aqueous drug solutions or dispersions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
A method for the production of dronabinol is disclosed, whereby: a) cannabidiol is isolated from fibrous hemp as cannabidiol acid, b) the cannabidiol, optionally obtained by decarboxylation, is cyclised in the presence of Lewis acids in a non-polar solvent to give dronabinol, c) the above is isolated by a chromatographic method and d) the residue obtained from the eluant after distilling off the solvent is purified by vacuum distillation. The dronabinol can be used for dispensing purposes in a syringe filled therewith and as inhalation solution for thermal nebulisation with hot air.
Claims (17)
1 A process for the production of dronabinol, characterised in that a) cannabidiol or cannabidiol acid is isolated from fibrous hemp, b) cannabidiol optionally obtained by decarboxylation is cyclised in the presence of Lewis acids in a non-polar solvent to give dronabinol, c) this is isolated by a chromatographic process and d) the residue obtained from the eluant after distilling off the solvent is purified by vacuum distillation.
2 The process as claimed in Claim 1, characterised in that the portions containing active ingredients are extracted from the blossoms or leaves of fibrous hemp.
3 The process as claimed in Claims 1 and 2, characterised in that the active ingredients are isolated by extraction with a non-polar solvent from the constituents obtained by sifting.
4 The process as claimed in Claims 1 to 3, characterised in that the active ingredients in the solvent are concentrated by extraction of fresh plant material with a solvent containing already active ingredients without distillation of the solvent.
5. The process as claimed in Claims 1 to 4, characterised in that in order to purify the active ingredients a) the extract is treated with aqueous lye, from which the free carbonic acids are precipitated following acidification and/or b) the solvent is distilled off and the residue is dissolved in a polar, organic solvent, whereby unwanted lipophilic constituents precipitate and are filtered out, and then the active ingredient contained in the filtrate is obtained by evaporation, the residue obtained by a) and/or b) is decarboxylated by heating, then distilled off in a vacuum and the resulting cannabidiol is crystallised.
6 The process as claimed in Claims 1 to 5, characterised in that cannabidiol is cyclised by addition of BF3 etherate, optionally in the presence of an alkaline drying agent, in an organic solvent to give dronabinol.
7 The process as claimed in Claims 1 to 6, characterised in that the cannabidiol is cyclised by addition of weak Lewis acids in an organic solvent to give dronabinol.
8 The process as claimed in Claims 6 and 7, characterised in that the solution containing dronabinol is chromatographed on a silica gel column.
9 The process as claimed in Claims 6 to 8, characterised in that the residue of dronabinol obtained from the eluant is cleaned by high-vacuum distillation.
9 A process for the production of a pharmaceutical preparation containing dronabinol, characterised in that, in a first step, a syringe is filled with dronabinol and, in a second step, an amount of the liquefied contents that is preferably measured is delivered.
11 The process as claimed in claim 10, characterised in that the contents are delivered without the remaining dronabinol in the syringe coming into contact with air.
12 The process as claimed in claim 10 or 11, characterised in that a precisely measured amount of dronabinol is added to sesame oil or other food oils, with dronabinol filed gelatin capsules, in which the dronabinol from Oleum Cacao is absorbed and set in the capsules or in an inhalation solution in which the dronabinol is dissolved in alcohol.
13. A process for transporting and/or storing dronabinol, characterised in that, in a first step, a syringe serving as a transportation and/or storage container is filled with dronabinol and, in a second step, the dronabinol is transported and/or stored.
The liquefied dronabinol can be delivered in a third step.
The liquefied dronabinol can be delivered in a third step.
14. The process as claimed in one of claims 10 to 13, characterised in that the syringe, primarily made of glass, is calibrated and/or gas-tight.
15. A device for transporting and/or storing dronabinol with a filling receptacle, characterised in that the filling receptacle has a syringe.
16. An inhalation solution for non-combustible thermal vaporising, characterised in that the inhalation solution contains dronabinol.
17. The inhalation solution as claimed in claim 15, characterised in that the solution also contains cannabidiol, a local anesthetic or etherial oils.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10106024.6 | 2001-02-05 | ||
| DE10106024A DE10106024B4 (en) | 2001-02-09 | 2001-02-09 | Process for the preparation of dronabinol |
| PCT/EP2002/001172 WO2002062782A1 (en) | 2001-02-09 | 2002-02-05 | Method for the production of dronabinol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2472561A1 true CA2472561A1 (en) | 2002-08-15 |
| CA2472561C CA2472561C (en) | 2010-11-02 |
Family
ID=7673475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2472561A Expired - Lifetime CA2472561C (en) | 2001-02-09 | 2002-02-05 | Process for the production of dronabinol |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1409474B1 (en) |
| AT (1) | ATE388144T1 (en) |
| CA (1) | CA2472561C (en) |
| DE (2) | DE10106024B4 (en) |
| ES (1) | ES2303547T3 (en) |
| WO (1) | WO2002062782A1 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7674922B2 (en) | 2005-09-29 | 2010-03-09 | Albany Molecular Research, Inc. | Process for production of delta-9-tetrahydrocannabinol |
| US10669248B2 (en) * | 2018-08-10 | 2020-06-02 | Natural Extraction Systems, LLC | Methods to chemically modify cannabinoids |
| US10822320B2 (en) | 2018-08-10 | 2020-11-03 | Natural Extraction Systems, LLC | Methods to purify cannabinoids |
| 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 |
| US11406913B2 (en) | 2013-10-04 | 2022-08-09 | Natural Extraction Systems, LLC | Method and apparatus for extracting botanical oils |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH697767B1 (en) * | 2002-01-16 | 2009-02-13 | Giuliano Silvestri | Method and apparatus for the separation of toxic levels of plant parts and for the extraction of THC. |
| GB2393182B (en) * | 2002-09-23 | 2007-03-14 | Gw Pharma Ltd | Method of preparing cannabidiol from plant material |
| DE102005028937B4 (en) * | 2005-06-22 | 2009-07-23 | Bionorica Ag | Process for the preparation of dronabinol |
| CA2866787C (en) | 2011-09-29 | 2021-05-18 | Thc Pharm Gmbh The Health Concept | Cannabinoid carboxylic acids, salts of cannabinoid carboxylic acids, and the production and uses of same |
| AU2014346466A1 (en) * | 2013-11-11 | 2016-05-19 | The Werc Shop, LLC | Solvent-free processing, system and methods |
| ES2907623T3 (en) | 2016-05-13 | 2022-04-25 | Symrise Ag | Method to purify cannabinoid compounds by simulated moving bed chromatography |
| CN107669744A (en) * | 2017-11-30 | 2018-02-09 | 云南汉木森生物科技有限责任公司 | Pack containing industrial hemp |
| US11767306B2 (en) * | 2020-01-17 | 2023-09-26 | Cannacraft, Inc | Methods for converting CBD to tetrahydrocannabinols |
| US11786838B2 (en) | 2020-03-23 | 2023-10-17 | Cannacraft, Inc. | Methods for removing pesticides from Cannabis products |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4100441A1 (en) * | 1991-01-09 | 1992-07-16 | Mack Chem Pharm | PROCESS FOR PREPARING 6,12-DIHYDRO-6-HYDROXY-CANNABIDIOL AND USE THEREOF FOR THE PREPARATION OF TRANS-DELTA-9-TETRAHYDROCANNABINOL |
| US5342971A (en) * | 1992-12-29 | 1994-08-30 | The Australian National University | Process for the preparation of dibenzo[b,d]pyrans |
-
2001
- 2001-02-09 DE DE10106024A patent/DE10106024B4/en not_active Expired - Fee Related
-
2002
- 2002-02-05 AT AT02719764T patent/ATE388144T1/en not_active IP Right Cessation
- 2002-02-05 ES ES02719764T patent/ES2303547T3/en not_active Expired - Lifetime
- 2002-02-05 DE DE50211842T patent/DE50211842D1/en not_active Expired - Lifetime
- 2002-02-05 EP EP02719764A patent/EP1409474B1/en not_active Expired - Lifetime
- 2002-02-05 WO PCT/EP2002/001172 patent/WO2002062782A1/en active IP Right Grant
- 2002-02-05 CA CA2472561A patent/CA2472561C/en not_active Expired - Lifetime
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7674922B2 (en) | 2005-09-29 | 2010-03-09 | Albany Molecular Research, Inc. | Process for production of delta-9-tetrahydrocannabinol |
| US8106244B2 (en) | 2005-09-29 | 2012-01-31 | Albany Molecular Research, Inc. | Process for production of delta-9-tetrahydrocannabinol |
| US11406913B2 (en) | 2013-10-04 | 2022-08-09 | Natural Extraction Systems, LLC | Method and apparatus for extracting botanical oils |
| 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 |
| US10669248B2 (en) * | 2018-08-10 | 2020-06-02 | Natural Extraction Systems, LLC | Methods to chemically modify cannabinoids |
| US10822320B2 (en) | 2018-08-10 | 2020-11-03 | Natural Extraction Systems, LLC | Methods to purify cannabinoids |
| US11643402B2 (en) | 2018-08-10 | 2023-05-09 | Natural Extraction Systems, LLC | Gas phase methods to decarboxylate cannabinoids |
| US11702397B2 (en) | 2018-08-10 | 2023-07-18 | Natural Extraction Systems, LLC | Methods to purify cannabinoids |
| US11040932B2 (en) | 2018-10-10 | 2021-06-22 | Treehouse Biotech, Inc. | Synthesis of cannabigerol |
Also Published As
| Publication number | Publication date |
|---|---|
| DE10106024B4 (en) | 2004-10-14 |
| ATE388144T1 (en) | 2008-03-15 |
| DE10106024A1 (en) | 2002-08-22 |
| EP1409474B1 (en) | 2008-03-05 |
| ES2303547T3 (en) | 2008-08-16 |
| EP1409474A1 (en) | 2004-04-21 |
| WO2002062782A1 (en) | 2002-08-15 |
| CA2472561C (en) | 2010-11-02 |
| DE50211842D1 (en) | 2008-04-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20220207 |