HRP20151301T1 - Postupci za proäśišä†avanje trans-(-)-delta9-tetrahidrokanabinola i trans-(+)-delta9-tetrahidrokanabinola - Google Patents
Postupci za proäśišä†avanje trans-(-)-delta9-tetrahidrokanabinola i trans-(+)-delta9-tetrahidrokanabinola Download PDFInfo
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- HRP20151301T1 HRP20151301T1 HRP20151301TT HRP20151301T HRP20151301T1 HR P20151301 T1 HRP20151301 T1 HR P20151301T1 HR P20151301T T HRP20151301T T HR P20151301TT HR P20151301 T HRP20151301 T HR P20151301T HR P20151301 T1 HRP20151301 T1 HR P20151301T1
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- 238000000034 method Methods 0.000 title claims 19
- 239000000203 mixture Substances 0.000 claims 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 33
- 238000002360 preparation method Methods 0.000 claims 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 12
- IRMPFYJSHJGOPE-UHFFFAOYSA-N olivetol Chemical compound CCCCCC1=CC(O)=CC(O)=C1 IRMPFYJSHJGOPE-UHFFFAOYSA-N 0.000 claims 12
- 239000012074 organic phase Substances 0.000 claims 9
- 239000012071 phase Substances 0.000 claims 9
- 238000002156 mixing Methods 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 7
- 239000003495 polar organic solvent Substances 0.000 claims 7
- 238000003756 stirring Methods 0.000 claims 7
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 4
- 230000002051 biphasic effect Effects 0.000 claims 4
- 238000001816 cooling Methods 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- 239000002841 Lewis acid Substances 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000003518 caustics Substances 0.000 claims 3
- 238000002425 crystallisation Methods 0.000 claims 3
- 230000008025 crystallization Effects 0.000 claims 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 3
- 238000002955 isolation Methods 0.000 claims 3
- 150000007517 lewis acids Chemical class 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 238000000926 separation method Methods 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 235000005074 zinc chloride Nutrition 0.000 claims 3
- 239000011592 zinc chloride Substances 0.000 claims 3
- 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
- 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 2
- 239000003377 acid catalyst Substances 0.000 claims 2
- 238000007033 dehydrochlorination reaction Methods 0.000 claims 2
- 239000012156 elution solvent Substances 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 2
- QHMBSVQNZZTUGM-MSOLQXFVSA-N 2-[(1s,6s)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@@H]1[C@@H](C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-MSOLQXFVSA-N 0.000 claims 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 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
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 230000005587 bubbling Effects 0.000 claims 1
- 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 1
- 229950011318 cannabidiol Drugs 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
- 229940043350 citral Drugs 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims 1
- 239000005457 ice water Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
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- 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
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Claims (18)
1. Postupak za dobivanje kristalnog (±)-Δ9-tertahidrokanabinola koji sadrži:
omogućavanje kristalizacije trans-(-)-Δ9-tertahidrokanabinola i trans-(+)-Δ9-tertahidrokanabinola iz prvog pripravka koji sadrži trans-(-)-Δ9-tertahidrokanabinol, trans-(+)-Δ9-tertahidrokanabinol, te nepolarno organsko otapalo da se dobije kristalizirani (±)-Δ9-tertahidrokanabinol,
naznačen time da je prvi pripravak dobiven pomoću:
(1) konverzije (-)-p-ment-2,8-dien-1-ola u trans-(+)-Δ9-tertahidrokanabinol uz
(i) miješanje smjese olivetola, cinkovog klorida i bezvodnog diklorometana na 40°C tijekom jednog sata, dodavanje otopine (-)-p-ment-2,8-dien-1-ola i bezvodnog diklorometana kap po kap tijekom 1 sata na 40°C u miješanu smjesu koja sadrži olivetol, te miješanje nastale smjese tijekom dodatnih 40 minuta na 40°C,
(ii) hlađenje smjese na -10°C, dodavanje otopine BF3·Et2O u bezvodnom diklorometanu kap po kap tijekom 1 sata na -10°C, te miješanje smjese tokom 30 minuta na -10°C, te
(iii) dodavanje hladne vode, miješanje nastale dvofazne smjese tokom 20 minuta na 0°C, te izoliranje sirovog trans-(+)-Δ9-tertahidrokanabinola iz organske faze;
(2) stvaranje dvofaznog pripravka koji sadrži (i) prvu organsku fazu, i (ii) alkoholno-kaustičnu fazu koja sadrži sirovi trans-(+)-Δ9-tertahidrokanabinol koji proizlazi iz koraka (1) i trans-(-)-Δ9-tertahidrokanabinol;
(4) separaciju Δ9-tertahidrokanabinola iz nastale faze koja sadrži Δ9-tertahidrokanabinol; i
(5) spajanje Δ9-tertahidrokanabinola iz koraka (4) s nepolarnim organskim otapalom da se dobije prvi pripravak.
2. Postupak za dobivanje kristalnog (±)-Δ9-tertahidrokanabinola koji sadrži:
omogućavanje kristalizacije trans-(-)-Δ9-tertahidrokanabinola i trans-(+)-Δ9-tertahidrokanabinola iz prvog pripravka koji sadrži trans-(-)-Δ9-tertahidrokanabinol, trans-(+)-Δ9-tertahidrokanabinol, te nepolarno organsko otapalo da se dobije provide kristalizirani (±)-Δ9-tertahidrokanabinol,
naznačen time da je prvi pripravak dobiven pomoću:
(1) konverzije cis/trans smjese (+)-p-ment-2,8-dien-1-ola u trans-(-)-Δ9-tertahidrokanabinol pomoću reakcije cis/trans smjese (+)-p-ment-2,8-dien-1-ola s olivetolom u prisutnosti kiselog katalizatora i sredstva za dehidraciju;
(2) stvaranje dvofaznog pripravka koji sadrži (i) prvu organsku fazu, i (ii) alkoholno-kaustičnu fazu koja sadrži sirovi trans-(-)-Δ9-tertahidrokanabinol koji proizlazi iz koraka (1) i trans-(+)-Δ9-tertahidrokanabinol;
(4) separaciju Δ9-tertahidrokanabinola iz nastale faze koja sadrži Δ9-tertahidrokanabinol; i
(5) spajanje Δ9-tertahidrokanabinola iz koraka (4) s nepolarnim organskim otapalom da se dobije prvi pripravak.
3. Postupak prema zahtjevu 2, naznačen time da kiseli katalizator je para-toluensulfonska kiselina ili BF3·Et2O.
4. Postupak za dobivanje kristalnog (±)-Δ9-tertahidrokanabinola koji sadrži:
omogućavanje kristalizacije trans-(-)-Δ9-tertahidrokanabinola i trans-(+)-Δ9-tetra-hidrokanabinola iz prvog pripravka koji sadrži trans-(-)-Δ9-tertahidrokanabinol, trans-(+)-Δ9-tertahidrokanabinol, te nepolarno organsko otapalo da se dobije kristalizirani (±)-Δ9-tertahidrokanabinol,
naznačen time da je prvi pripravak dobiven pomoću:
(1) konverzije (±)-p-ment-2,8-dien-1-ola u trans-(±)-Δ9-tertahidrokanabinol pomoću
(i) miješanja smjese olivetola, cinkovog klorida i bezvodnog diklorometana na 40°C tijekom jednog sata, dodavanje otopine (±)-p-ment-2,8-dien-1-ola i bezvodnog diklorometana kap po kap tijekom 1 sata na 40°C u miješanu smjesu koja sadrži olivetol, i miješanje dobivene smjese tijekom dodatnih 40 minuta na 40°C,
(ii) hlađenja smjese na -10°C, dodavanje otopine BF3·Et2O u bezvodnom diklorometanu kap po kap tijekom 1 sata na -10°C, i miješanje smjese tijekom 30 minuta na -10°C, i
(iii) dodavanja hladne vode, miješanja dobivene dvofazne smjese tijekom 20 minuta na 0°C, te izoliranja sirovog trans-(±)-Δ9-tertahidrokanabinola iz organske faze;
(2) stvaranje dvofaznog pripravka koji sadrži (i) prvu organsku fazu, i (ii) alkoholno-kaustičnu fazu koja sadrži sirovi trans-(±)-Δ9-tertahidrokanabinol koji proizlazi iz koraka (1);
(4) razdvajanje Δ9-tertahidrokanabinola iz nastale faze koja sadrži Δ9-tertahidrokanabinol; i
(5) spajanje Δ9-tertahidrokanabinola iz koraka (4) s nepolarnim organskim otapalom da se dobije prvi pripravak.
5. Postupak za dobivanje kristalnog (±)-Δ9-tertahidrokanabinola prema zahtjevu 2, naznačen time da je korak (1) zamijenjen sa slijedećim korakom (1):
1. reakcijom (-)-kanabidiola s Lewisovom kiselinom u inertnom otapalu pod bezvodnim uvjetima u sirovi trans-(-)-Δ9-tertahidrokanabinol koji je korišten u koraku (2).
6. Postupak prema zahtjevu 5, naznačen time da Lewisova kiselina je BF3·Et2O.
7. Postupak za dobivanje kristalnog (±)-Δ9-tertahidrokanabinola prema zahtjevu 1, naznačen time da je korak (1) zamijenjen sa slijedećim korakom (1):
(1) dodavanje otopine BF3·Et2O u bezvodnom diklorometanu kap po kap uz miješanje tijekom 1 sata u otopinu (+)-kanabidiola u bezvodnom diklorometanu na -5°C, miješanje nastale smjese tijekom 1.5 sata na -5°C, dodavanje smjese u smjesu leda i 7% NaHCO3, te izoliranje iz organske faze sirovog trans-(+)-Δ9-tertahidrokanabinola koji je korišten u koraku (2).
8. Postupak za dobivanje kristalnog (±)-Δ9-tertahidrokanabinola prema zahtjevu 4, naznačen time da je korak (1) zamijenjen sa slijedećim korakom (1):
1. dodavanje otopine BF3·Et2O u bezvodnom diklorometanu kap po kap uz miješanje tijekom 1 sata u otopinu (±)-kanabidiola u bezvodnom diklorometanu na -5°C, miješanje nastale smjese tijekom 1.5 sata na -5°C, dodavanje smjese u 7% NaHCO3, te izoliranje iz organske faze sirovog trans-(±)-Δ9-tertahidrokanabinola koji je korišten u koraku (2).
9. Postupak za dobivanje kristalnog (±)-Δ9-tertahidrokanabinola prema zahtjevu 1, naznačen time da je korak (1) zamijenjen sa slijedećim korakom (1):
1. reakcija (+)-Δ8-tertahidrokanabinola s HCl nakon čega slijedi dehidrokloriranje u sirovi trans-(+)-Δ9-tertahidrokanabinol koji je korišten u koraku (2).
10. Postupak za dobivanje kristalnog (±)-Δ9-tertahidrokanabinola prema zahtjevu 2, naznačen time da je korak (1) zamijenjen sa slijedećim korakom (1):
(1) reakcija (-)-Δ8-tertahidrokanabinola s HCl nakon čega slijedi dehidrokloriranje u sirovi trans-(-)-Δ9-tertahidrokanabinol koji je korišten u koraku (2).
11. Postupak za dobivanje kristalnog (±)-Δ9-tertahidrokanabinola prema zahtjevu 4, naznačen time da je korak (1) zamijenjen sa slijedećim korakom (1):
(1)
(i) miješanje smjese (±)-A8-tertahidrokanabinola, cinkovog klorida, i bezvodnog diklorometana tijekom 0.5 sata na 25°C pod Ar atmosferom, hlađenje smjese na 0°C, brabotiranje plinovitog vodikovog klorida kroz smjesu tokom 1.5 sata, ulijevanje smjese u ledenu kupelj i miješanje nastale dvofazne smjese tijekom 1 sata na 0 do 5°C, izoliranje dobivenog (±)-9-kloro-trans-heksahidrokanabinola iz organske faze,
(ii) miješanje smjese izoliranog (±)-9-kloro-trans-heksahidrokanabinola s kalijevim-tert-amilatom i bezvodnim toluenom tijekom 75 minuta na 65°C, hlađenje smjese i njegovo ulijevanje u ledenu vodu, te izolaciju iz organske faze nastalog sirovog trans-(±)-Δ9-tertahidrokanabinola koji je korišten u koraku (2).
12. Postupak za dobivanje kristalnog (±)-Δ9-tertahidrokanabinola prema zahtjevu 4, naznačen time da je korak (1) zamijenjen sa slijedećim korakom (1):
(1) reakcija citrala s olivetolom u prisutnosti Lewisove kiseline do sirovog trans-(±)-Δ9-tertahidrokanabinola koji je korišten u koraku (2).
13. Postupak za pripravu pripravka trans-(-)-Δ9-tertahidrokanabinola, koji se sastoji od:
omogućavanja da se pripravak koji sadrži (±)-Δ9-tertahidrokanabinol i otapalo za eluiranje razdvoje na kiralnoj stacionarnoj fazi da se dobije pripravak trans-(-)-Δ9-tertahidrokanabinola, ili
pripravka trans-(+)-Δ9-tertahidrokanabinola, koji se sastoji od:
omogućavanja da se pripravak koji sadrži (±)-Δ9-tertahidrokanabinol i otapalo za eluiranje razdvoje na kiralnoj stacionarnoj fazi da se dobije pripravak trans-(+)-Δ9-tertahidrokanabinola,
naznačen time da je (±)-Δ9-tertahidrokanabinol dobiven iz kristaliziranog (±)-Δ9-tertahidrokanabinola, te pri čemu je kristalizirani (±)-Δ9-tertahidrokanabinol dobiven postupkom prema bilo kojem od zahtjeva 1 do 12.
14. Postupak prema bilo kojem od zahtjeva 1 do 13, naznačen time da je trans-(-)-Δ9-tertahidrokanabinol 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-tertahidrokanabinola.
15. Postupak prema bilo kojem od zahtjeva 1 do 14, naznačen time da (±)-Δ9-tertahidrokanabinol sadrži barem 95%, poželjno barem 98%, poželjnije barem 99% težinski trans-(-)-Δ9-tertahidrokanabinola i trans-(+)-Δ9-tertahidrokanabinola u odnosu na ukupnu količinu kanabinoida.
16. Postupak prema bilo kojem od zahtjeva 1 do 15, naznačen time da je nepolarno organsko otapalo (C4-C10)alifatski ugljikovodik s ravnim-lancem ili razgranatim-lancem, (C4-C10)cikloalifatski ugljikovodik, ili bilo koja njihova mješavina, pri čemu je ugljikovodik s ravnim-lancem ili razgranatim-lancem poželjno pentan, heksan, heptan, izooktan, ili bilo koja njihova mješavina, te je poželjnije n-heptan.
17. Dvofazni pripravak dobiven iz koraka (2) postupkom prema bilo kojem od zahtjeva 1 do 12.
18. Pripravak koji sadrži trans-(-)-Δ9-tertahidrokanabinol, trans-(+)-Δ9-tertahidrokanabinol, organsko otapalo koje se ne miješa s vodom, alkohol koji se miješa s vodom, vodu, te hidroksid alkalijskog metala, naznačen time da je trans-(-)-Δ9-tertahidrokanabinol prisutan u količini od 0.75 do 1.25 molarnih ekvivalenata po molarnom ekvivalentu trans-(+)-Δ9-tertahidrokanabinola.
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| EP10179360.2A EP2289509B1 (en) | 2004-11-22 | 2005-11-18 | Methods for purifying trans-(-)-delta9-tetrahydrocannabinol and trans-(+)-delta9-tetrahydrocannabinol |
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Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US11485700B2 (en) * | 2018-06-28 | 2022-11-01 | Symrise Ag | Synthesis of (+)-cannabinoids and their therapeutic effects |
| CA3073093A1 (en) | 2018-08-03 | 2020-02-06 | Biomass Oil Separation Solutions, Llc | Processes and apparatus for extraction of substances and enriched extracts from plant material |
| EP3864000A4 (en) | 2018-10-10 | 2022-08-10 | Treehouse Biosciences, Inc. | CANNABIGEROL SYNTHESIS |
| JP2022512777A (ja) | 2018-10-31 | 2022-02-07 | エナンティア，エセ．エレ． | カンナビノイドの共結晶の固体組成物 |
| EP3653596A1 (en) | 2018-11-14 | 2020-05-20 | Indena S.p.A. | Continuous flow synthesis of cannabidiol |
| CN109734554B (zh) * | 2019-02-25 | 2021-11-23 | 江苏暨明医药科技有限公司 | 一种反式-薄荷基-2,8-二烯-1-醇的合成工艺 |
| 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 |
| WO2020248062A1 (en) * | 2019-06-11 | 2020-12-17 | Canopy Growth Corporation | Improved methods for cannabinoid isomerization |
| US10799546B1 (en) | 2019-07-26 | 2020-10-13 | Biomass Oil Separation Solutions, Llc | Modular, integrated process and apparatus for extracting, refining and remediating active substances from plant material |
| US11542243B1 (en) | 2019-09-26 | 2023-01-03 | FusionFarms, LLC | Method of converting delta9-THC to delta10-THC and the purification of the delta10-THC by crystallization |
| CA3158415A1 (en) * | 2019-10-21 | 2021-04-29 | Esolate Ltd | Compositions comprising superfine compounds and production thereof |
| GB2588455B (en) * | 2019-10-25 | 2022-12-21 | Gw Res Ltd | Cannabinoid compound |
| GB2588457B (en) * | 2019-10-25 | 2022-12-21 | Gw Res Ltd | Cannabinoid compound |
| US20220340507A1 (en) | 2020-03-12 | 2022-10-27 | Council Of Scientific And Industrial Research An Indian Registered Body Incorporated Under The Regn. | Process for the synthesis of cannabidiol and intermediates thereof |
| CN113336705B (zh) * | 2021-08-09 | 2021-12-10 | 中国农业科学院农产品加工研究所 | 一种大麻二酚-2-咪唑-1-甲酸酯及其应用 |
| WO2024028516A1 (en) | 2022-08-05 | 2024-02-08 | Salud & Semillas, S.L. | CANNABINOID SYNTHESIS STARTING OUT FROM OLIVETOL AND TERPENE IN DICHLOROMETHANE WITH FeCl3 * 6H2O AS CATALYST |
| CN115583933B (zh) * | 2022-10-31 | 2024-02-06 | 暨明医药科技（苏州）有限公司 | 一种高纯度四氢大麻素同系物的制备方法 |
| CN115784836A (zh) * | 2022-12-08 | 2023-03-14 | 南京康立瑞生物科技有限公司 | 一种高选择性的制备反式-薄荷基-2,8-二烯-1-醇的方法 |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3507885A (en) | 1966-03-25 | 1970-04-21 | Hoffmann La Roche | 3-alkyl-6h-dibenzo(b,d)pyrans |
| CH481911A (de) | 1967-05-19 | 1969-11-30 | Theodor Dr Petrzilka | Verfahren zur Herstellung von tricyclischen Verbindungen |
| US3854480A (en) | 1969-04-01 | 1974-12-17 | Alza Corp | Drug-delivery system |
| US3668224A (en) | 1970-07-02 | 1972-06-06 | Theodor Petrzilka | PROCESS OF PRODUCING 6a, 10a-TRANS-6a,7,8,10a-TETRAHYDRODIBENZO (b,d)-PYRANS |
| US4025516A (en) | 1975-06-23 | 1977-05-24 | The John C. Sheehan Institute For Research, Inc. | Process for the preparation of (-)-6a,10a-trans-6a,7,8,10a-tetrahydrodibenzo[b,d]-pyrans |
| US4381399A (en) | 1981-12-21 | 1983-04-26 | Aerojet-General Corporation | Purification of tetrahydrodibenzo[b,d]pyrans from crude synthetic mixtures |
| US4970075A (en) | 1986-07-18 | 1990-11-13 | Euroceltique, S.A. | Controlled release bases for pharmaceuticals |
| US4861598A (en) | 1986-07-18 | 1989-08-29 | Euroceltique, S.A. | Controlled release bases for pharmaceuticals |
| DE4100441A1 (de) | 1991-01-09 | 1992-07-16 | Mack Chem Pharm | Verfahren zur herstellung von 6,12-dihydro-6-hydroxy-cannabidiol und dessen verwendung zur herstellung von trans-delta-9-tetrahydrocannabinol |
| US6703418B2 (en) | 1991-02-26 | 2004-03-09 | Unimed Pharmaceuticals, Inc. | Appetite stimulation and induction of weight gain in patients suffering from symptomatic HIV infection |
| US5389375A (en) | 1993-05-21 | 1995-02-14 | University Of Mississippi | Stable suppository formulations effecting bioavailability of Δ9 -thc |
| US5965161A (en) | 1994-11-04 | 1999-10-12 | Euro-Celtique, S.A. | Extruded multi-particulates |
| EP0833622B8 (en) | 1995-06-12 | 2005-10-12 | G.D. Searle & Co. | Compositions comprising a cyclooxygenase-2 inhibitor and a 5-lipoxygenase inhibitor |
| US6017963A (en) | 1995-11-14 | 2000-01-25 | Euro-Celtique, S.A. | Formulation for intranasal administration |
| US6328992B1 (en) | 1997-03-03 | 2001-12-11 | Lawrence L. Brooke | Cannabinoid patch and method for cannabis transdermal delivery |
| GB9726916D0 (en) | 1997-12-19 | 1998-02-18 | Danbiosyst Uk | Nasal formulation |
| US6730519B2 (en) | 1998-10-26 | 2004-05-04 | The University Of Mississippi | Method of preparing delta-9-tetrahydrocannabinol |
| US6365416B1 (en) | 1998-10-26 | 2002-04-02 | The University Of Mississippi | Method of preparing delta-9-tetrahydrocannabinol |
| US6509005B1 (en) | 1998-10-27 | 2003-01-21 | Virginia Commonwealth University | Δ9 Tetrahydrocannabinol (Δ9 THC) solution metered dose inhaler |
| FI990915A0 (fi) | 1999-04-23 | 1999-04-23 | Orion Yhtymae Oyj | Jauheinhalaattori |
| US6403126B1 (en) | 1999-05-26 | 2002-06-11 | Websar Innovations Inc. | Cannabinoid extraction method |
| US6555139B2 (en) | 1999-06-28 | 2003-04-29 | Wockhardt Europe Limited | Preparation of micron-size pharmaceutical particles by microfluidization |
| US6747058B1 (en) | 1999-08-20 | 2004-06-08 | Unimed Pharmaceuticals, Inc. | Stable composition for inhalation therapy comprising delta-9-tetrahydrocannabinol and semiaqueous solvent therefor |
| US6620351B2 (en) | 2000-05-24 | 2003-09-16 | Auburn University | Method of forming nanoparticles and microparticles of controllable size using supercritical fluids with enhanced mass transfer |
| GB2368061B (en) | 2000-10-20 | 2005-05-11 | Gw Pharmaceuticals Ltd | Dose dispensing apparatus |
| MXPA03003895A (es) | 2000-10-30 | 2003-07-28 | Euro Celtique Sa | Formulaciones de hidrocodona de liberacion controlada. |
| US6730330B2 (en) | 2001-02-14 | 2004-05-04 | Gw Pharma Limited | Pharmaceutical formulations |
| CH695661A5 (de) * | 2001-03-06 | 2006-07-31 | Forsch Hiscia Ver Fuer Krebsfo | Pharmazeutische Zusammensetzung. |
| WO2002070506A2 (en) | 2001-03-07 | 2002-09-12 | Websar Innovations Inc. | Conversion of cbd to δ8-thc and δ9-thc |
| US20030050334A1 (en) | 2001-04-30 | 2003-03-13 | Murty Ram B. | Process for extraction of Delta-9-Tetrahydrocannabinol and other related cannabinoids and preparation of specific strength marijuana cigarettes |
| GB0112752D0 (en) | 2001-05-25 | 2001-07-18 | Johnson Matthey Plc | Synthesis of cannabinoids |
| US20030044458A1 (en) | 2001-08-06 | 2003-03-06 | Curtis Wright | Oral dosage form comprising a therapeutic agent and an adverse-effect agent |
| NZ552547A (en) * | 2002-02-01 | 2008-03-28 | Resolution Chemicals Ltd | Production of Delta 9 tetrahydrocannabinol from plant material |
| AU2002242779A1 (en) | 2002-02-21 | 2003-09-09 | Timothee Biel | Device for driving motor vehicles, in particular with hybrid propulsion |
| UA79281C2 (en) | 2002-04-03 | 2007-06-11 | Solvay Pharm Bv | Stabilized composition comprising a natural cannabinoid compound and process for the preparation thereof |
| US6946150B2 (en) | 2002-08-14 | 2005-09-20 | Gw Pharma Limited | Pharmaceutical formulation |
| GB0222077D0 (en) | 2002-09-23 | 2002-10-30 | Gw Pharma Ltd | Methods of preparing cannabinoids from plant material |
| CA2770448C (en) | 2002-11-12 | 2014-03-25 | Prairie Plant Systems Inc. | Cannabinoid esters |
| US20040229939A1 (en) | 2003-02-14 | 2004-11-18 | Chowdhury Dipak K. | Tetrahydrocannabinol compositions and methods of manufacture and use thereof |
| CA2544900A1 (en) | 2003-11-05 | 2005-05-19 | Unimed Pharmaceuticals, Inc. | Delta-9- the treatment of multiple sclerosis |
| GB0329635D0 (en) | 2003-12-23 | 2004-01-28 | Johnson Matthey Plc | Process for purifying trans-tetrahydrocannabinol |
| EP1773801A1 (de) | 2004-07-19 | 2007-04-18 | Cilag Ltd. | Verfahren zur gewinnung von reinem tetrahydrocannabinol |
| GB0425445D0 (en) | 2004-11-18 | 2004-12-22 | Smithkline Beecham Corp | Novel compositions |
| 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 |
| WO2009018389A1 (en) | 2007-07-30 | 2009-02-05 | Alltranz Inc. | Prodrugs of cannabidiol, compositions comprising prodrugs of cannabidiol and methods of using the same |
| US8642645B2 (en) * | 2011-05-20 | 2014-02-04 | Brooks Kelly Research, LLC. | Pharmaceutical composition comprising Cannabinoids |
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- 2011-05-17 CY CY20111100473T patent/CY1111471T1/el unknown
- 2011-05-24 HR HR20110385T patent/HRP20110385T1/hr unknown
- 2011-08-29 HK HK11109114.9A patent/HK1154796A1/xx unknown
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2012
- 2012-01-03 HK HK12100001.3A patent/HK1159500A1/xx unknown
- 2012-03-26 JP JP2012068947A patent/JP2012180350A/ja active Pending
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2013
- 2013-02-22 US US13/774,955 patent/US8937097B2/en active Active
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2015
- 2015-01-13 US US14/596,034 patent/US9278083B2/en active Active
- 2015-11-30 HR HRP20151301TT patent/HRP20151301T1/hr unknown
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2016
- 2016-03-04 US US15/061,891 patent/US20160199344A1/en not_active Abandoned
- 2016-03-04 US US15/061,780 patent/US9744151B2/en active Active
- 2016-03-04 US US15/061,859 patent/US9675581B2/en active Active
- 2016-03-23 HR HRP20160300TT patent/HRP20160300T1/hr unknown
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