HRP20110385T1 - Postupci za pročišćavanje trans-(-)-delta9-tetrahidrokanabinola i trans-(+)-delta9-tetrahidrokanabinola - Google Patents
Postupci za pročišćavanje trans-(-)-delta9-tetrahidrokanabinola i trans-(+)-delta9-tetrahidrokanabinola Download PDFInfo
- Publication number
- HRP20110385T1 HRP20110385T1 HR20110385T HRP20110385T HRP20110385T1 HR P20110385 T1 HRP20110385 T1 HR P20110385T1 HR 20110385 T HR20110385 T HR 20110385T HR P20110385 T HRP20110385 T HR P20110385T HR P20110385 T1 HRP20110385 T1 HR P20110385T1
- Authority
- HR
- Croatia
- Prior art keywords
- tetrahydrocannabinol
- trans
- composition
- phase
- organic solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 18
- 239000000203 mixture Substances 0.000 claims abstract 60
- 239000003518 caustics Substances 0.000 claims abstract 20
- 239000012071 phase Substances 0.000 claims abstract 20
- 239000003495 polar organic solvent Substances 0.000 claims abstract 17
- 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 14
- 238000000926 separation method Methods 0.000 claims abstract 13
- 230000002051 biphasic effect Effects 0.000 claims abstract 10
- 239000012074 organic phase Substances 0.000 claims abstract 10
- 239000012156 elution solvent Substances 0.000 claims abstract 6
- 230000005526 G1 to G0 transition Effects 0.000 claims abstract 5
- 229960004242 dronabinol Drugs 0.000 claims abstract 2
- 238000010828 elution Methods 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims abstract 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 4
- 229910052809 inorganic oxide Inorganic materials 0.000 claims 4
- 239000004215 Carbon black (E152) Substances 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 229930195733 hydrocarbon Natural products 0.000 claims 3
- 150000002430 hydrocarbons Chemical class 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 2
- 229930003827 cannabinoid Natural products 0.000 claims 2
- 239000003557 cannabinoid Substances 0.000 claims 2
- 229940065144 cannabinoids Drugs 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 239000000377 silicon dioxide Substances 0.000 claims 2
- SBTVLCPCSXMWIQ-UHFFFAOYSA-N (3,5-dimethylphenyl) carbamate Chemical compound CC1=CC(C)=CC(OC(N)=O)=C1 SBTVLCPCSXMWIQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006565 (C4-C7) cyclic group Chemical group 0.000 claims 1
- 229920000856 Amylose Polymers 0.000 claims 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 125000006371 dihalo methyl group Chemical group 0.000 claims 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 125000006372 monohalo methyl group Chemical group 0.000 claims 1
- 125000006370 trihalo methyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
Classifications
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- 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
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4875—Compounds of unknown constitution, e.g. material from plants or animals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Botany (AREA)
- Zoology (AREA)
- Neurology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Nutrition Science (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63055604P | 2004-11-22 | 2004-11-22 | |
| PCT/EP2005/012378 WO2006053766A1 (en) | 2004-11-22 | 2005-11-18 | Methods for purifying trans-(-)-δ9-tetrahydrocannabinol and trans-(+)-δ9-tetrahydrocannabinol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110385T1 true HRP20110385T1 (hr) | 2011-06-30 |
Family
ID=35789123
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110385T HRP20110385T1 (hr) | 2004-11-22 | 2011-05-24 | Postupci za pročišćavanje trans-(-)-delta9-tetrahidrokanabinola i trans-(+)-delta9-tetrahidrokanabinola |
| HRP20151301TT HRP20151301T1 (hr) | 2004-11-22 | 2015-11-30 | Postupci za proäśišä†avanje trans-(-)-delta9-tetrahidrokanabinola i trans-(+)-delta9-tetrahidrokanabinola |
| HRP20160300TT HRP20160300T1 (hr) | 2004-11-22 | 2016-03-23 | Postupci za pročišćavanje trans-(-)-delta9-tetrahidrokanabinola i trans-(+)-delta9-tetrahidrokanabinola |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20151301TT HRP20151301T1 (hr) | 2004-11-22 | 2015-11-30 | Postupci za proäśišä†avanje trans-(-)-delta9-tetrahidrokanabinola i trans-(+)-delta9-tetrahidrokanabinola |
| HRP20160300TT HRP20160300T1 (hr) | 2004-11-22 | 2016-03-23 | Postupci za pročišćavanje trans-(-)-delta9-tetrahidrokanabinola i trans-(+)-delta9-tetrahidrokanabinola |
Country Status (31)
| Country | Link |
|---|---|
| US (6) | US8383842B2 (ja) |
| EP (3) | EP2356987B1 (ja) |
| JP (3) | JP4995728B2 (ja) |
| KR (1) | KR100919719B1 (ja) |
| CN (2) | CN102151259A (ja) |
| AR (1) | AR054989A1 (ja) |
| AT (1) | ATE500824T1 (ja) |
| AU (2) | AU2005305944B2 (ja) |
| BR (1) | BRPI0519803A2 (ja) |
| CA (2) | CA2921590C (ja) |
| CY (1) | CY1111471T1 (ja) |
| DE (1) | DE602005026852D1 (ja) |
| DK (3) | DK2289509T3 (ja) |
| EA (1) | EA012299B1 (ja) |
| ES (3) | ES2556802T3 (ja) |
| HK (3) | HK1109058A1 (ja) |
| HR (3) | HRP20110385T1 (ja) |
| HU (2) | HUE027197T2 (ja) |
| IL (1) | IL183306A (ja) |
| ME (2) | ME02306B (ja) |
| MX (1) | MX2007006104A (ja) |
| NO (1) | NO331831B1 (ja) |
| NZ (1) | NZ556038A (ja) |
| PL (3) | PL2289509T3 (ja) |
| PT (2) | PT2289509E (ja) |
| RS (3) | RS54338B1 (ja) |
| SI (3) | SI2356987T1 (ja) |
| TW (2) | TWI436991B (ja) |
| UA (1) | UA88491C2 (ja) |
| WO (1) | WO2006053766A1 (ja) |
| ZA (1) | ZA200706837B (ja) |
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| TWI436991B (zh) | 2004-11-22 | 2014-05-11 | Euro Celtique Sa | 用於純化反-（-）-△９-四氫大麻酚與反-（＋）-△９-四氫大麻酚之方法 |
| TWI366460B (en) * | 2005-06-16 | 2012-06-21 | Euro Celtique Sa | Cannabinoid active pharmaceutical ingredient for improved dosage forms |
| WO2007041167A2 (en) | 2005-09-29 | 2007-04-12 | Amr Technology, Inc. | Process for production of delta-9-tetrahydrocannabinol |
| US8980940B2 (en) | 2006-11-10 | 2015-03-17 | Johnson Matthey Public Limited Company | Stable cannabinoid compositions and methods for making and storing them |
| US8039509B2 (en) | 2006-11-10 | 2011-10-18 | Johnson Matthey Public Limited Company | Composition comprising (−)-Δ9-trans-tetrahydrocannabinol |
| GB0702895D0 (en) * | 2007-02-14 | 2007-03-28 | Resolution Chemicals Ltd | Delta 9 tetrahydrocannabinol derivatives |
| GB0703284D0 (en) * | 2007-02-20 | 2007-03-28 | Resolution Chemicals Ltd | Delta 9 - tetrahydrocannabinol processing |
| WO2009099868A1 (en) * | 2008-02-06 | 2009-08-13 | Mallinckrodt Inc. | Process for the preparation of (-) -delta 9-tetrahydrocannabinol |
| US10624859B2 (en) | 2012-08-20 | 2020-04-21 | Rhodes Technologies | Systems and methods for increasing stability of dronabinol compositions |
| CA3111682A1 (en) | 2014-06-26 | 2015-12-30 | Island Breeze Systems Ca, Llc | Mdi related products and methods of use |
| US10155708B2 (en) * | 2015-01-22 | 2018-12-18 | Phytoplant Research S.L. | Methods of purifying cannabinoids, compositions and kits thereof |
| US11034639B2 (en) | 2015-01-22 | 2021-06-15 | Phytoplant Research S.L. | Methods of purifying cannabinoids using liquid:liquid chromatography |
| US10207198B2 (en) | 2015-01-22 | 2019-02-19 | Phytoplant Research S.L. | Methods of purifying cannabinoids using liquid:liquid chromatography |
| CN106268657A (zh) * | 2015-05-14 | 2017-01-04 | 株式会社大赛璐 | 光学异构体用分离剂 |
| US10059683B2 (en) | 2015-07-10 | 2018-08-28 | Noramco, Inc. | Process for the production of cannabidiol and delta-9-tetrahydrocannabinol |
| PL3455213T3 (pl) * | 2016-05-13 | 2022-04-04 | Symrise Ag | Sposób oczyszczania związków kannabinoidowych przez symulowaną chromatografię z ruchomym złożem |
| US10499584B2 (en) | 2016-05-27 | 2019-12-10 | New West Genetics | Industrial hemp Cannabis cultivars and seeds with stable cannabinoid profiles |
| US10399920B2 (en) | 2016-06-01 | 2019-09-03 | S&B Pharma, Inc. | Crystalline form of cannabidiol |
| US10239808B1 (en) | 2016-12-07 | 2019-03-26 | Canopy Holdings, LLC | Cannabis extracts |
| CN106810426B (zh) * | 2016-12-29 | 2020-05-08 | 暨明医药科技（苏州）有限公司 | 一种大麻二酚的合成方法 |
| US11213558B2 (en) | 2017-05-17 | 2022-01-04 | Orochem Technologies, Inc. | CBX extraction-isolation process |
| US10189762B1 (en) * | 2017-07-07 | 2019-01-29 | Orochem Technologies, Inc. | Process for purification and separation of cannabinoids, from dried hemp and cannabis leaves |
| SG11202001725SA (en) * | 2017-09-01 | 2020-03-30 | Pureform Global Inc | Synthetic cannabidiol compositions and methods of making the same |
| US11202771B2 (en) | 2018-01-31 | 2021-12-21 | Treehouse Biotech, Inc. | Hemp powder |
| US11192870B2 (en) | 2018-03-07 | 2021-12-07 | Socati Technologies—Oregon, Llc | Continuous isolation of cannabidiol and conversion of cannabidiol to delta 8-tetrahydrocannabinol and delta 9-tetrahydrocannabinol |
| US11851415B2 (en) | 2018-03-07 | 2023-12-26 | Cleen Technology Inc. | Continuous isolation of cannabidiol and cannabinoids and conversion of cannabidiol to delta 8-tetrahydrocannabinol and delta 9-tetrahydrocannabinol |
| CN112105606A (zh) * | 2018-03-07 | 2020-12-18 | 索卡蒂科技俄勒冈有限公司 | 大麻素的连续分离以及大麻素向δ8-四氢大麻酚和δ9-四氢大麻酚的转化 |
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| CN111943813B (zh) * | 2019-05-17 | 2023-04-14 | 上海特化医药科技有限公司 | 大麻二酚类化合物的制备方法 |
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