HRP20160300T1 - Postupci za pročišćavanje trans-(-)-delta9-tetrahidrokanabinola i trans-(+)-delta9-tetrahidrokanabinola - Google Patents
Postupci za pročišćavanje trans-(-)-delta9-tetrahidrokanabinola i trans-(+)-delta9-tetrahidrokanabinola Download PDFInfo
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- HRP20160300T1 HRP20160300T1 HRP20160300TT HRP20160300T HRP20160300T1 HR P20160300 T1 HRP20160300 T1 HR P20160300T1 HR P20160300T T HRP20160300T T HR P20160300TT HR P20160300 T HRP20160300 T HR P20160300T HR P20160300 T1 HRP20160300 T1 HR P20160300T1
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- Prior art keywords
- tetrahydrocannabinol
- trans
- phase
- acid
- preparation
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- 238000000034 method Methods 0.000 title claims 15
- 239000012071 phase Substances 0.000 claims 14
- 239000002253 acid Substances 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 8
- 238000002360 preparation method Methods 0.000 claims 8
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 claims 6
- 239000003518 caustics Substances 0.000 claims 6
- 239000012074 organic phase Substances 0.000 claims 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 5
- 230000001476 alcoholic effect Effects 0.000 claims 5
- XXGMIHXASFDFSM-UHFFFAOYSA-N Delta9-tetrahydrocannabinol Natural products CCCCCc1cc2OC(C)(C)C3CCC(=CC3c2c(O)c1O)C XXGMIHXASFDFSM-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 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
- 239000003495 polar organic solvent Substances 0.000 claims 3
- CYQFCXCEBYINGO-IRXDYDNUSA-N (6as,10as)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol Chemical compound C1=C(C)CC[C@@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@H]21 CYQFCXCEBYINGO-IRXDYDNUSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 230000005526 G1 to G0 transition Effects 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 239000012535 impurity Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 229930003827 cannabinoid Natural products 0.000 claims 1
- 239000003557 cannabinoid Substances 0.000 claims 1
- 229940065144 cannabinoids Drugs 0.000 claims 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 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
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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
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Botany (AREA)
- Zoology (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Nutrition Science (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Medicinal Preparation (AREA)
Claims (11)
1. Postupak za uklanjanje nečistoća iz pripravka koji sadrži trans-(-)-Δ9-tetrahidrokanabinol i trans-(+)-Δ9-tetrahidrokanabinol prije kristalizacije (±)-Δ9-tetrahidrokanabinola, naznačen time da postupak sadrži:
(a) dovođenje u kontakt trans-(-)-Δ9-tetrahidrokanabinola i trans-(+)-Δ9-tetrahidrokanabinola s prvim organskim otapalom netopljivim u vodi, alkoholom koji se miješa s vodom, vodom, i hidroksidom alkalnog metala, čime se dobije dvofazni pripravak koji sadrži (i) prvu organsku fazu, te (ii) alkoholno-kaustičnu fazu koja sadrži trans-(-)-Δ9-tetrahidrokanabinol i trans-(+)-Δ9-tetrahidrokanabinol;
(b) razdvajanje alkoholno-kaustične faze koja sadrži trans-(-)-Δ9-tetrahidrokanabinol i trans-(+)-Δ9-tetrahidrokanabinol od prve organske faze;
(c) dovođenje u kontakt alkoholno-kaustične faze s kiselinom da se dobije kiselinom obrađena alkoholna faza.
2. Postupak za uklanjanje nečistoća iz pripravka koji sadrži trans-(-)-Δ9-tetrahidrokanabinol ili trans-(+)-Δ9-tetrahidrokanabinol prije kristalizacije (±)-Δ9-tetrahidrokanabinola, naznačen time da postupak sadrži:
(a) dovođenje u kontakt trans-(-)-Δ9-tetrahidrokanabinola ili trans-(+)-Δ9-tetrahidrokanabinola s prvim organskim otapalom netopljivim u vodi, alkoholom koji se miješa s vodom, vodom, i hidroksidom alkalnog metala, čime se dobije dvofazni pripravak koji sadrži (i) prvu organsku fazu, te (ii) alkoholno-kaustičnu fazu koja sadrži trans-(-)-Δ9-tetrahidrokanabinol ili trans-(+)-Δ9-tetrahidrokanabinol;
(b) razdvajanje alkoholno-kaustične faze koja sadrži trans-(-)-Δ9-tetrahidrokanabinol ili trans-(+)-Δ9-tetrahidrokanabinol od prve organske faze;
(c) dovođenje u kontakt alkoholno-kaustične faze s kiselinom da se dobije kiselinom obrađena alkoholna faza.
3. Postupak prema zahtjevu 1 ili 2, naznačen time da kiselina je limunska kiselina ili octena kiselina.
4. Postupak prema bilo kojem od zahtjeva 1 do 3, naznačen time da se kiselina dodaje u količini dovoljnoj za postizanje pH od 5 do 9.
5. Postupak prema bilo kojem od zahtjeva 1 do 4, naznačen time da sadrži dodatni korak:
(d) dovođenje u kontakt kiselinom obrađene alkoholne faze s drugim organskim otapalom netopljivim u vodi da se dobije (i) druga organska faza koja sadrži Δ9-tetrahidrokanabinol i (ii) alkoholnu fazu obrađenu kiselinom.
6. Postupak prema zahtjevu 5, naznačen time da sadrži dodatni korak:
(e) razdvajanja druge organske faze od alkoholne faze obrađene kiselinom.
7. Postupak za dobivanje kristalnog (+)-Δ9-tetrahidrokanabinola koji sadrži:
omogućavanje da trans-(-)-Δ9-tetrahidrokanabinol i trans-(+)-Δ9-tetrahidrokanabinol kristaliziraju iz prvog pripravka koji sadrži trans-(-)-Δ9-tetrahidrokanabinol, trans-(+)-Δ9-tetrahidrokanabinol, te ne-polarno organsko otapalo da se dobije kristalni (±)-Δ9-tetrahidrokanabinol, naznačen time da je prvi pripravak dobiven
(a) provođenjem postupka prema bilo kojem od zahtjeva 1 do 6,
(b) razdvajanjem Δ9-tetrahidrokanabinola iz dobivene faze koja sadrži Δ9-tetrahidrokanabinol; i
(c) dovođenjem u kontakt Δ9-tetrahidrokanabinola iz koraka (b) s ne-polarnim organskim otapalom i proizvoljno njegovim enantiomerom da se dobije prvi pripravak.
8. Postupak prema zahtjevu 7, naznačen time da ne-polarno organsko otapalo je ravnolančani ili razgranati (C4-C10)alifatski ugljikovodik, (C4-C10)cikloalifatski ugljikovodik, ili bilo koja njihova smjesa, pri čemu je ravnolančani ili razgranati ugljikovodik poželjno pentan, heksan, heptan, izooktan, ili bilo koja njihova smjesa i poželjnije je n-heptan.
9. Postupak za pripremanje pripravka trans-(-)-Δ9-tetrahidrokanabinola, koji sadrži:
omogućavanje da se pripravak koji sadrži (±)-Δ9-tetrahidrokanabinol i eluirajuće otapalo razdvajaju na kiralnoj stacionarnoj fazi radi dobivanja pripravka trans-(-)-Δ9-tetrahidrokanabinola, ili
pripravka trans-(+)- Δ9-tetrahidrokanabinola, koji sadrži:
omogućavanje da se pripravak koji sadrži (±)-Δ9-tetrahidrokanabinol i eluirajuće otapalo razdvajaju na kiralnoj stacionarnoj fazi radi dobivanja pripravka trans-(+)-Δ9-tetrahidrokanabinola,
naznačen time da se (±)-Δ9-tetrahidrokanabinol dobiva od kristalnog (±)-Δ9-tetrahidrokanabinola, te pri čemu se kristalni (+)-Δ9-tetrahidrokanabinol dobiva postupkom prema patentnom zahtjevu 7 ili 8.
10. Postupak prema bilo kojem od zahtjeva 7 do 9, naznačen time da je trans-(-)-Δ9-tetrahidrokanabinol prisutan u prvom pripravku u količini od 0.75 do 1.25 molarnih ekvivalenata, poželjno od 0.9 do 1.1 molarnih ekvivalenata, poželjnije od 0.95 do 1.05 molarnih ekvivalenata i čak još poželjnije 1 molarni ekvivalent po molarnom ekvivalentu trans-(+)-Δ9-tetrahidrokanabinola.
11. Postupak prema bilo kojem od zahtjeva 7 do 10, naznačen time da (±)-Δ9-tetrahidrokanabinol sadrži barem 95% težinski, poželjno barem 98% težinski i poželjnije barem 99% težinski trans-(-)-Δ9-tetrahidrokanabinola i trans-(+)-Δ9-tetrahidrokanabinola u odnosu na ukupnu količinu kanabinoida.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63055604P | 2004-11-22 | 2004-11-22 | |
| EP10179374.3A EP2356987B1 (en) | 2004-11-22 | 2005-11-18 | Methods for purifying trans-(-)-delta9-tetrahydrocannabinol and trans-(+)-delta9-tetrahydrocannabinol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20160300T1 true HRP20160300T1 (hr) | 2016-04-22 |
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 Before (2)
| 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 |
Country Status (31)
| Country | Link |
|---|---|
| US (6) | US8383842B2 (hr) |
| EP (3) | EP2356987B1 (hr) |
| JP (3) | JP4995728B2 (hr) |
| KR (1) | KR100919719B1 (hr) |
| CN (2) | CN101076329B (hr) |
| AR (1) | AR054989A1 (hr) |
| AT (1) | ATE500824T1 (hr) |
| AU (2) | AU2005305944B2 (hr) |
| BR (1) | BRPI0519803A2 (hr) |
| CA (2) | CA2587957C (hr) |
| CY (1) | CY1111471T1 (hr) |
| DE (1) | DE602005026852D1 (hr) |
| DK (3) | DK2289509T3 (hr) |
| EA (1) | EA012299B1 (hr) |
| ES (3) | ES2556802T3 (hr) |
| HK (3) | HK1109058A1 (hr) |
| HR (3) | HRP20110385T1 (hr) |
| HU (2) | HUE027197T2 (hr) |
| IL (1) | IL183306A (hr) |
| ME (2) | ME02306B (hr) |
| MX (1) | MX2007006104A (hr) |
| NO (1) | NO331831B1 (hr) |
| NZ (1) | NZ556038A (hr) |
| PL (3) | PL2356987T3 (hr) |
| PT (2) | PT1824475E (hr) |
| RS (3) | RS54537B1 (hr) |
| SI (3) | SI2289509T1 (hr) |
| TW (2) | TWI436991B (hr) |
| UA (1) | UA88491C2 (hr) |
| WO (1) | WO2006053766A1 (hr) |
| ZA (1) | ZA200706837B (hr) |
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| US8980940B2 (en) | 2006-11-10 | 2015-03-17 | Johnson Matthey Public Limited Company | Stable cannabinoid compositions and methods for making and storing them |
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| US10189762B1 (en) | 2017-07-07 | 2019-01-29 | Orochem Technologies, Inc. | Process for purification and separation of cannabinoids, from dried hemp and cannabis leaves |
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