CA2504743C - Cannabinoid crystalline derivatives and process of cannabinoid purification - Google Patents
Cannabinoid crystalline derivatives and process of cannabinoid purification Download PDFInfo
- Publication number
- CA2504743C CA2504743C CA2504743A CA2504743A CA2504743C CA 2504743 C CA2504743 C CA 2504743C CA 2504743 A CA2504743 A CA 2504743A CA 2504743 A CA2504743 A CA 2504743A CA 2504743 C CA2504743 C CA 2504743C
- Authority
- CA
- Canada
- Prior art keywords
- cannabinoid
- aryl
- process according
- sulfonyl halide
- aryl sulfonate
- 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.)
- Expired - Fee Related
Links
- 238000000746 purification Methods 0.000 title claims abstract description 14
- 229930003827 cannabinoid Natural products 0.000 title claims description 80
- 239000003557 cannabinoid Substances 0.000 title claims description 80
- 238000000034 method Methods 0.000 title claims description 30
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 239000013078 crystal Substances 0.000 claims description 32
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000001555 benzenes Chemical group 0.000 claims description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 8
- -1 naphthyl compound Chemical class 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000004996 alkyl benzenes Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 241000218236 Cannabis Species 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 229960004242 dronabinol Drugs 0.000 abstract description 16
- 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 abstract description 10
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 abstract description 6
- 238000003860 storage Methods 0.000 abstract description 4
- 150000003512 tertiary amines Chemical class 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 24
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229940065144 cannabinoids Drugs 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003461 sulfonyl halides Chemical class 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 1
- MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 1
- KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 1
- DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 1
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
- VBGLYOIFKLUMQG-UHFFFAOYSA-N Cannabinol Chemical compound C1=C(C)C=C2C3=C(O)C=C(CCCCC)C=C3OC(C)(C)C2=C1 VBGLYOIFKLUMQG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 description 1
- 229960003453 cannabinol Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 240000004308 marijuana Species 0.000 description 1
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- DLRDEMODNIPHMU-UHFFFAOYSA-N tert-butyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OC(C)(C)C)C=C1 DLRDEMODNIPHMU-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2770448A CA2770448C (en) | 2002-11-12 | 2003-11-06 | Cannabinoid esters |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42554302P | 2002-11-12 | 2002-11-12 | |
| US60/425,543 | 2002-11-12 | ||
| US43502702P | 2002-12-20 | 2002-12-20 | |
| US60/435,027 | 2002-12-20 | ||
| PCT/US2003/035599 WO2004043946A1 (en) | 2002-11-12 | 2003-11-06 | Cannabinoid crystalline derivatives and process of cannabinoid purification |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2770448A Division CA2770448C (en) | 2002-11-12 | 2003-11-06 | Cannabinoid esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2504743A1 CA2504743A1 (en) | 2004-05-27 |
| CA2504743C true CA2504743C (en) | 2012-04-24 |
Family
ID=32314593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2504743A Expired - Fee Related CA2504743C (en) | 2002-11-12 | 2003-11-06 | Cannabinoid crystalline derivatives and process of cannabinoid purification |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7402686B2 (enExample) |
| EP (1) | EP1560819B1 (enExample) |
| JP (1) | JP2006508132A (enExample) |
| AT (1) | ATE410419T1 (enExample) |
| AU (1) | AU2003287585B2 (enExample) |
| CA (1) | CA2504743C (enExample) |
| DE (1) | DE60324011D1 (enExample) |
| DK (1) | DK1560819T3 (enExample) |
| ES (1) | ES2315548T3 (enExample) |
| MX (1) | MXPA05004966A (enExample) |
| PT (1) | PT1560819E (enExample) |
| SI (1) | SI1560819T1 (enExample) |
| WO (1) | WO2004043946A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1428526A1 (en) * | 2002-12-13 | 2004-06-16 | Rijksuniversiteit Groningen | Formulation for fast dissolution of lipophilic compounds |
| WO2006007734A1 (de) * | 2004-07-19 | 2006-01-26 | Cilag Ltd. | Verfahren zur gewinnung von reinem tetrahydrocannabinol |
| EA200701246A1 (ru) * | 2004-12-09 | 2008-06-30 | Инсис Терапьютикс, Инк. | Стабильные при комнатной температуре составы дронабинола |
| AU2012201041B2 (en) * | 2005-09-29 | 2012-12-06 | Albany Molecular Research, Inc. | Process for production of delta-9-tetrahydrocannabinol |
| EP2578577A1 (en) * | 2005-09-29 | 2013-04-10 | Albany Molecular Research, Inc. | Sulfonyl esters of tetrahydrocannabinol and derivatives thereof |
| CA2659775A1 (en) * | 2006-08-04 | 2008-02-14 | Insys Therapeutics Inc. | Aqueous dronabinol formulations |
| 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 |
| CA2698752A1 (en) * | 2007-08-06 | 2009-02-12 | Insys Therapeutics Inc. | Oral cannabinoid liquid formulations and methods of treatment |
| WO2009099868A1 (en) * | 2008-02-06 | 2009-08-13 | Mallinckrodt Inc. | Process for the preparation of (-) -delta 9-tetrahydrocannabinol |
| US9220294B2 (en) | 2014-02-11 | 2015-12-29 | Timothy McCullough | Methods and devices using cannabis vapors |
| US10821240B2 (en) | 2014-02-11 | 2020-11-03 | Vapor Cartridge Technology Llc | Methods and drug delivery devices using cannabis |
| US9380813B2 (en) | 2014-02-11 | 2016-07-05 | Timothy McCullough | Drug delivery system and method |
| US9539295B2 (en) | 2014-12-05 | 2017-01-10 | Bradley Michael Bohus | Cannabidiol (CBD) enriched alcohol |
| US9585867B2 (en) | 2015-08-06 | 2017-03-07 | Charles Everett Ankner | Cannabinod formulation for the sedation of a human or animal |
| US10239808B1 (en) | 2016-12-07 | 2019-03-26 | Canopy Holdings, LLC | Cannabis extracts |
| US10272360B2 (en) | 2017-08-05 | 2019-04-30 | Priya Naturals, Inc. | Phytochemical extraction system and methods to extract phytochemicals from plants including plants of the family Cannabaceae sensu stricto |
| EP3745884A1 (en) | 2018-01-31 | 2020-12-09 | Canopy Holdings, Llc | Hemp powder |
| US10897925B2 (en) | 2018-07-27 | 2021-01-26 | Joseph Pandolfino | Articles and formulations for smoking products and vaporizers |
| US20200035118A1 (en) | 2018-07-27 | 2020-01-30 | Joseph Pandolfino | Methods and products to facilitate smokers switching to a tobacco heating product or e-cigarettes |
| US11040932B2 (en) | 2018-10-10 | 2021-06-22 | Treehouse Biotech, Inc. | Synthesis of cannabigerol |
| GB201910389D0 (en) * | 2019-07-19 | 2019-09-04 | Gw Pharma Ltd | Novel compounds, methods for their manufacture, and uses thereof |
| US11925907B2 (en) | 2019-07-22 | 2024-03-12 | Canopy Growth Corporation | Continuous crystallization of cannabinoids in a stirred-tank reactor |
| WO2021055079A1 (en) | 2019-09-16 | 2021-03-25 | Vapor Cartridge Technology Llc | Drug delivery system with stackable substrates |
| JP2023512578A (ja) * | 2020-02-06 | 2023-03-27 | ロンドン ファーマシューティカルズ アンド リサーチ コーポレーション | Ｃアナビンオイド硫酸エステル、その塩及び用途 |
| AU2022362107A1 (en) * | 2021-10-11 | 2024-05-02 | Anebulo Pharmaceuticals, Inc. | Crystalline forms of a cannabinoid receptor type 1 (cb1) modulator and methods of use and preparation thereof |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636058A (en) | 1966-03-25 | 1972-01-18 | Hoffmann La Roche | 7 10 - dihydro - 3 - alkyl - 6h - dibenzo(b d) pyran-6 9(8h)-diones and 5-hydroxy-7-alkyl-4-chromanones |
| US3507888A (en) | 1966-08-30 | 1970-04-21 | Searle & Co | Process and intermediates for manufacture of 17-oxygenated estr-4-en-3-ones |
| US3728360A (en) | 1971-08-31 | 1973-04-17 | Little Inc A | Ester derivatives of tetrahydrocannabinol |
| US4188495A (en) | 1977-11-14 | 1980-02-12 | Pfizer Inc. | 1,9-Dihydroxyoctahydrophenanthrenes and intermediates therefor |
| US4206225A (en) | 1978-09-22 | 1980-06-03 | Pfizer Inc. | 2,10-Disubstituted dibenzo[b,d]pyrans and benzo[c]quinolines |
| US4341906A (en) | 1979-09-24 | 1982-07-27 | Pfizer Inc. | 1,9-Dihydroxyoctahydrophenanthrenes |
| US4381399A (en) | 1981-12-21 | 1983-04-26 | Aerojet-General Corporation | Purification of tetrahydrodibenzo[b,d]pyrans from crude synthetic mixtures |
| GB9303911D0 (en) | 1993-02-26 | 1993-04-14 | Zeneca Ltd | Chemical process |
| JP3384163B2 (ja) * | 1994-11-09 | 2003-03-10 | 株式会社ニコン | 顕微鏡対物レンズ |
| US6008383A (en) | 1998-10-26 | 1999-12-28 | University Of Mississippi | Method of preparing delta-9-tetrahydrocannabinol esters |
| WO2006000734A1 (en) | 2004-06-23 | 2006-01-05 | Bp P.L.C. | The synthesis of the micro-porous silica gel and its application to the preparation of catalysts for c2 oxygenates synthesis from syngas |
-
2003
- 2003-11-06 DK DK03781830T patent/DK1560819T3/da active
- 2003-11-06 JP JP2004551898A patent/JP2006508132A/ja not_active Withdrawn
- 2003-11-06 SI SI200331388T patent/SI1560819T1/sl unknown
- 2003-11-06 US US10/533,576 patent/US7402686B2/en not_active Expired - Lifetime
- 2003-11-06 PT PT03781830T patent/PT1560819E/pt unknown
- 2003-11-06 MX MXPA05004966A patent/MXPA05004966A/es active IP Right Grant
- 2003-11-06 AU AU2003287585A patent/AU2003287585B2/en not_active Expired - Fee Related
- 2003-11-06 CA CA2504743A patent/CA2504743C/en not_active Expired - Fee Related
- 2003-11-06 ES ES03781830T patent/ES2315548T3/es not_active Expired - Lifetime
- 2003-11-06 DE DE60324011T patent/DE60324011D1/de not_active Expired - Lifetime
- 2003-11-06 EP EP03781830A patent/EP1560819B1/en not_active Expired - Lifetime
- 2003-11-06 AT AT03781830T patent/ATE410419T1/de not_active IP Right Cessation
- 2003-11-06 WO PCT/US2003/035599 patent/WO2004043946A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003287585A1 (en) | 2004-06-03 |
| EP1560819B1 (en) | 2008-10-08 |
| EP1560819A1 (en) | 2005-08-10 |
| PT1560819E (pt) | 2008-11-03 |
| WO2004043946A1 (en) | 2004-05-27 |
| ES2315548T3 (es) | 2009-04-01 |
| SI1560819T1 (sl) | 2009-06-30 |
| JP2006508132A (ja) | 2006-03-09 |
| US7402686B2 (en) | 2008-07-22 |
| DK1560819T3 (da) | 2009-02-09 |
| ATE410419T1 (de) | 2008-10-15 |
| AU2003287585B2 (en) | 2009-05-07 |
| US20060094774A1 (en) | 2006-05-04 |
| CA2504743A1 (en) | 2004-05-27 |
| DE60324011D1 (de) | 2008-11-20 |
| MXPA05004966A (es) | 2005-08-02 |
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