CA3137559A1 - Compositions comprenant des formes non cristallines de cannabidiol - Google Patents
Compositions comprenant des formes non cristallines de cannabidiol Download PDFInfo
- Publication number
- CA3137559A1 CA3137559A1 CA3137559A CA3137559A CA3137559A1 CA 3137559 A1 CA3137559 A1 CA 3137559A1 CA 3137559 A CA3137559 A CA 3137559A CA 3137559 A CA3137559 A CA 3137559A CA 3137559 A1 CA3137559 A1 CA 3137559A1
- Authority
- CA
- Canada
- Prior art keywords
- composition
- cannabidiol
- mass
- percent
- terpene
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 172
- 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 title claims abstract description 103
- QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 title claims abstract description 102
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 title claims abstract description 102
- 229950011318 cannabidiol Drugs 0.000 title claims abstract description 102
- PCXRACLQFPRCBB-ZWKOTPCHSA-N dihydrocannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)C)CCC(C)=C1 PCXRACLQFPRCBB-ZWKOTPCHSA-N 0.000 title claims abstract description 102
- 239000007788 liquid Substances 0.000 claims abstract description 64
- 238000007710 freezing Methods 0.000 claims abstract description 34
- 230000008014 freezing Effects 0.000 claims abstract description 34
- 230000007704 transition Effects 0.000 claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 150000003505 terpenes Chemical class 0.000 claims description 79
- 235000007586 terpenes Nutrition 0.000 claims description 78
- 230000003647 oxidation Effects 0.000 claims description 34
- 238000007254 oxidation reaction Methods 0.000 claims description 34
- NPNUFJAVOOONJE-ZIAGYGMSSA-N β-(E)-Caryophyllene Chemical group C1CC(C)=CCCC(=C)[C@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-ZIAGYGMSSA-N 0.000 claims description 32
- FAMPSKZZVDUYOS-UHFFFAOYSA-N alpha-Caryophyllene Natural products CC1=CCC(C)(C)C=CCC(C)=CCC1 FAMPSKZZVDUYOS-UHFFFAOYSA-N 0.000 claims description 30
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 24
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 claims description 22
- NVEQFIOZRFFVFW-RGCMKSIDSA-N caryophyllene oxide Chemical group C=C1CC[C@H]2O[C@]2(C)CC[C@H]2C(C)(C)C[C@@H]21 NVEQFIOZRFFVFW-RGCMKSIDSA-N 0.000 claims description 22
- 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 description 22
- 229960004242 dronabinol Drugs 0.000 claims description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 18
- RGZSQWQPBWRIAQ-CABCVRRESA-N (-)-alpha-Bisabolol Chemical group CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-CABCVRRESA-N 0.000 claims description 16
- 239000001500 (2R)-6-methyl-2-[(1R)-4-methyl-1-cyclohex-3-enyl]hept-5-en-2-ol Substances 0.000 claims description 16
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 claims description 16
- RGZSQWQPBWRIAQ-LSDHHAIUSA-N alpha-Bisabolol Natural products CC(C)=CCC[C@@](C)(O)[C@@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-LSDHHAIUSA-N 0.000 claims description 16
- NPNUFJAVOOONJE-UHFFFAOYSA-N beta-cariophyllene Natural products C1CC(C)=CCCC(=C)C2CC(C)(C)C21 NPNUFJAVOOONJE-UHFFFAOYSA-N 0.000 claims description 16
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 claims description 16
- NPNUFJAVOOONJE-UONOGXRCSA-N caryophyllene Natural products C1CC(C)=CCCC(=C)[C@@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-UONOGXRCSA-N 0.000 claims description 16
- BXWQUXUDAGDUOS-UHFFFAOYSA-N gamma-humulene Natural products CC1=CCCC(C)(C)C=CC(=C)CCC1 BXWQUXUDAGDUOS-UHFFFAOYSA-N 0.000 claims description 16
- QBNFBHXQESNSNP-UHFFFAOYSA-N humulene Natural products CC1=CC=CC(C)(C)CC=C(/C)CCC1 QBNFBHXQESNSNP-UHFFFAOYSA-N 0.000 claims description 16
- -1 terpene alcohols Chemical class 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 14
- NVEQFIOZRFFVFW-UHFFFAOYSA-N 9-epi-beta-caryophyllene oxide Natural products C=C1CCC2OC2(C)CCC2C(C)(C)CC21 NVEQFIOZRFFVFW-UHFFFAOYSA-N 0.000 claims description 11
- RSYBQKUNBFFNDO-UHFFFAOYSA-N caryophyllene oxide Natural products CC1(C)CC2C(=C)CCC3OC3(C)CCC12C RSYBQKUNBFFNDO-UHFFFAOYSA-N 0.000 claims description 11
- 239000013078 crystal Substances 0.000 claims description 10
- USFOCJBPTUMHRF-DNNYSMPMSA-N tricyclohumuladiol Chemical compound C[C@]1([C@@H](CC[C@](C)(O)[C@@H]2[C@@H]3C(C2)(C)C)O)[C@@H]3C1 USFOCJBPTUMHRF-DNNYSMPMSA-N 0.000 claims description 10
- XLQPEBGTWDBJAW-DHUIQQBUSA-N tricyclohumuladiol Natural products CC1(C)C[C@@]2(C)[C@H]1[C@H]3C[C@@]3(C)[C@H](O)CC[C@]2(C)O XLQPEBGTWDBJAW-DHUIQQBUSA-N 0.000 claims description 10
- 235000001510 limonene Nutrition 0.000 claims description 9
- 229940087305 limonene Drugs 0.000 claims description 9
- UVOLYTDXHDXWJU-NRFANRHFSA-N Cannabichromene Natural products C1=C[C@](C)(CCC=C(C)C)OC2=CC(CCCCC)=CC(O)=C21 UVOLYTDXHDXWJU-NRFANRHFSA-N 0.000 claims description 8
- UVOLYTDXHDXWJU-UHFFFAOYSA-N Cannabichromene Chemical compound C1=CC(C)(CCC=C(C)C)OC2=CC(CCCCC)=CC(O)=C21 UVOLYTDXHDXWJU-UHFFFAOYSA-N 0.000 claims description 8
- ORKZJYDOERTGKY-UHFFFAOYSA-N Dihydrocannabichromen Natural products C1CC(C)(CCC=C(C)C)OC2=CC(CCCCC)=CC(O)=C21 ORKZJYDOERTGKY-UHFFFAOYSA-N 0.000 claims description 8
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 8
- TWVJWDMOZJXUID-SDDRHHMPSA-N Guaiol Chemical compound C1([C@H](CC[C@H](C2)C(C)(C)O)C)=C2[C@@H](C)CC1 TWVJWDMOZJXUID-SDDRHHMPSA-N 0.000 claims description 8
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 claims description 8
- TWVJWDMOZJXUID-QJPTWQEYSA-N guaiol Natural products OC(C)(C)[C@H]1CC=2[C@H](C)CCC=2[C@@H](C)CC1 TWVJWDMOZJXUID-QJPTWQEYSA-N 0.000 claims description 8
- 150000003904 phospholipids Chemical class 0.000 claims description 8
- 150000003626 triacylglycerols Chemical class 0.000 claims description 8
- 239000001993 wax Substances 0.000 claims description 8
- JXRRJAPYKWLLHV-KFRFFZJSSA-N (-)-Humulene epoxide II Natural products C[C@]12O[C@@H]1CC/C=C(/C)\CC(C)(C)/C=C/C2 JXRRJAPYKWLLHV-KFRFFZJSSA-N 0.000 claims description 7
- QTGAEXCCAPTGLB-UOAUIWSESA-N (1r,4e,8e,11r)-4,7,7,11-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,8-diene Chemical compound C1CC(/C)=C/CC(C)(C)\C=C\C[C@@]2(C)O[C@@H]21 QTGAEXCCAPTGLB-UOAUIWSESA-N 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 150000004665 fatty acids Chemical class 0.000 claims description 7
- QTGAEXCCAPTGLB-UHFFFAOYSA-N humulene epoxide II Natural products C1CC(C)=CCC(C)(C)C=CCC2(C)OC21 QTGAEXCCAPTGLB-UHFFFAOYSA-N 0.000 claims description 7
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 6
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 6
- RKQDKXOBRXTSFS-FTFIOASISA-N Humulene epoxide Natural products C[C@]12O[C@@H]1CC(C)(C)/C=C/C/C(/C)=C\CC2 RKQDKXOBRXTSFS-FTFIOASISA-N 0.000 claims description 5
- ZHCPVYWHSOILQL-LWRPEEJLSA-N Humulenol II Chemical compound C\C1=C\CC(C)(C)\C=C/CC(=C)[C@H](O)CC1 ZHCPVYWHSOILQL-LWRPEEJLSA-N 0.000 claims description 5
- ZHCPVYWHSOILQL-UHFFFAOYSA-N Humulenol-II Natural products CC1=CCC(C)(C)C=CCC(=C)C(O)CC1 ZHCPVYWHSOILQL-UHFFFAOYSA-N 0.000 claims description 5
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 claims description 5
- WSIKWSKUPSHZMF-ODEKHORNSA-N humulene epoxide III Natural products CC1(C)[C@@H]2O[C@H]2C/C(/C)=C/CC/C(/C)=C/C1 WSIKWSKUPSHZMF-ODEKHORNSA-N 0.000 claims description 5
- RKQDKXOBRXTSFS-QZFXXANLSA-N humulene epoxide i Chemical compound C1C(C)(C)\C=C/CC(/C)=C\CCC2(C)OC21 RKQDKXOBRXTSFS-QZFXXANLSA-N 0.000 claims description 5
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 claims description 4
- QXACEHWTBCFNSA-SFQUDFHCSA-N cannabigerol Chemical compound CCCCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1 QXACEHWTBCFNSA-SFQUDFHCSA-N 0.000 claims description 4
- QXACEHWTBCFNSA-UHFFFAOYSA-N cannabigerol Natural products CCCCCC1=CC(O)=C(CC=C(C)CCC=C(C)C)C(O)=C1 QXACEHWTBCFNSA-UHFFFAOYSA-N 0.000 claims description 4
- BQOFWKZOCNGFEC-UHFFFAOYSA-N carene Chemical compound C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 claims description 4
- 238000004891 communication Methods 0.000 claims description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 4
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 claims description 4
- OGLDWXZKYODSOB-UHFFFAOYSA-N α-phellandrene Chemical compound CC(C)C1CC=C(C)C=C1 OGLDWXZKYODSOB-UHFFFAOYSA-N 0.000 claims description 4
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 claims description 4
- YHQGMYUVUMAZJR-UHFFFAOYSA-N α-terpinene Chemical compound CC(C)C1=CC=C(C)CC1 YHQGMYUVUMAZJR-UHFFFAOYSA-N 0.000 claims description 4
- YKFLAYDHMOASIY-UHFFFAOYSA-N γ-terpinene Chemical compound CC(C)C1=CCC(C)=CC1 YKFLAYDHMOASIY-UHFFFAOYSA-N 0.000 claims description 4
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 claims description 3
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 claims description 3
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 claims description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 3
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 3
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 claims description 3
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 claims description 3
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 claims description 3
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 3
- 229930006722 beta-pinene Natural products 0.000 claims description 3
- 235000000484 citronellol Nutrition 0.000 claims description 3
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 claims description 3
- 229930007744 linalool Natural products 0.000 claims description 3
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 claims description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 2
- NZGWDASTMWDZIW-MRVPVSSYSA-N (+)-pulegone Chemical compound C[C@@H]1CCC(=C(C)C)C(=O)C1 NZGWDASTMWDZIW-MRVPVSSYSA-N 0.000 claims description 2
- QEBNYNLSCGVZOH-NFAWXSAZSA-N (+)-valencene Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CCC=C21 QEBNYNLSCGVZOH-NFAWXSAZSA-N 0.000 claims description 2
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 claims description 2
- 239000001871 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol Substances 0.000 claims description 2
- 239000001890 (2R)-8,8,8a-trimethyl-2-prop-1-en-2-yl-1,2,3,4,6,7-hexahydronaphthalene Substances 0.000 claims description 2
- 239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 claims description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 2
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 claims description 2
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 claims description 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims description 2
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 2
- 241000723346 Cinnamomum camphora Species 0.000 claims description 2
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims description 2
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 claims description 2
- 239000005770 Eugenol Substances 0.000 claims description 2
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- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 2
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- 229940088601 alpha-terpineol Drugs 0.000 claims description 2
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- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 claims description 2
- 229940116229 borneol Drugs 0.000 claims description 2
- 229930006739 camphene Natural products 0.000 claims description 2
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 claims description 2
- 229930008380 camphor Natural products 0.000 claims description 2
- 229960000846 camphor Drugs 0.000 claims description 2
- 229960005233 cineole Drugs 0.000 claims description 2
- 229940043350 citral Drugs 0.000 claims description 2
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 claims description 2
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 claims description 2
- 229960002217 eugenol Drugs 0.000 claims description 2
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims description 2
- 229940113087 geraniol Drugs 0.000 claims description 2
- 125000002149 humulene group Chemical group 0.000 claims description 2
- 229940095045 isopulegol Drugs 0.000 claims description 2
- ZYTMANIQRDEHIO-UHFFFAOYSA-N neo-Isopulegol Natural products CC1CCC(C(C)=C)C(O)C1 ZYTMANIQRDEHIO-UHFFFAOYSA-N 0.000 claims description 2
- 150000007823 ocimene derivatives Chemical class 0.000 claims description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims description 2
- 229930007459 p-menth-8-en-3-one Natural products 0.000 claims description 2
- BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 claims description 2
- USDOQCCMRDNVAH-UHFFFAOYSA-N sigma-cadinene Natural products C1C=C(C)CC2C(C(C)C)CC=C(C)C21 USDOQCCMRDNVAH-UHFFFAOYSA-N 0.000 claims description 2
- 229940116411 terpineol Drugs 0.000 claims description 2
- XJPBRODHZKDRCB-UHFFFAOYSA-N trans-alpha-ocimene Natural products CC(=C)CCC=C(C)C=C XJPBRODHZKDRCB-UHFFFAOYSA-N 0.000 claims description 2
- WCTNXGFHEZQHDR-UHFFFAOYSA-N valencene Natural products C1CC(C)(C)C2(C)CC(C(=C)C)CCC2=C1 WCTNXGFHEZQHDR-UHFFFAOYSA-N 0.000 claims description 2
- USDOQCCMRDNVAH-KKUMJFAQSA-N β-cadinene Chemical compound C1C=C(C)C[C@H]2[C@H](C(C)C)CC=C(C)[C@@H]21 USDOQCCMRDNVAH-KKUMJFAQSA-N 0.000 claims description 2
- 230000008018 melting Effects 0.000 abstract description 6
- 238000002844 melting Methods 0.000 abstract description 6
- 229930003827 cannabinoid Natural products 0.000 description 5
- 239000003557 cannabinoid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 4
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 4
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 4
- 235000009120 camo Nutrition 0.000 description 4
- 235000005607 chanvre indien Nutrition 0.000 description 4
- 239000011487 hemp Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- IAIHUHQCLTYTSF-UHFFFAOYSA-N 2,2,4-trimethylbicyclo[2.2.1]heptan-3-ol Chemical compound C1CC2(C)C(O)C(C)(C)C1C2 IAIHUHQCLTYTSF-UHFFFAOYSA-N 0.000 description 2
- IKYYCHCPHQHUGT-UHFFFAOYSA-N 2,3,4,6-tetrahydro-1h-benzo[c]chromen-1-ol Chemical compound C12=CC=CC=C2COC2=C1C(O)CCC2 IKYYCHCPHQHUGT-UHFFFAOYSA-N 0.000 description 2
- WGCVHDPMCONZFM-UHFFFAOYSA-N 2-oxabicyclo[9.1.0]dodeca-3,7-diene Chemical compound C12OC=CCCC=CCCC2C1 WGCVHDPMCONZFM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940065144 cannabinoids Drugs 0.000 description 2
- VDIJMZCHRVRDCC-UHFFFAOYSA-N cycloundeca-1,3-dien-1-ol Chemical compound C1(=CC=CCCCCCCC1)O VDIJMZCHRVRDCC-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000003571 electronic cigarette Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- OXSNSEYMDPDYLQ-UHFFFAOYSA-N 2-methylidenebicyclo[7.2.0]undec-4-ene Chemical compound C=C1CC=CCCCC2CCC12 OXSNSEYMDPDYLQ-UHFFFAOYSA-N 0.000 description 1
- BDMCPAYEXLABIH-UHFFFAOYSA-N C1C2OCC=CCC=CCCC12 Chemical compound C1C2OCC=CCC=CCCC12 BDMCPAYEXLABIH-UHFFFAOYSA-N 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- IRMPFYJSHJGOPE-UHFFFAOYSA-N olivetol Chemical compound CCCCCC1=CC(O)=CC(O)=C1 IRMPFYJSHJGOPE-UHFFFAOYSA-N 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
Classifications
-
- 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
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
-
- 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
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Engineering & Computer Science (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Divers aspects de l'invention concernent des compositions (i) qui comprennent du cannabidiol, qui ont soit un point de congélation soit une température de transition vitreuse-liquide inférieure au point de fusion de cannabidiol pur, (ii) des contenants qui contiennent de telles compositions, et (iii) des procédés de fabrication de produits de cannabidiol.
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962839564P | 2019-04-26 | 2019-04-26 | |
| US62/839,564 | 2019-04-26 | ||
| US201962845231P | 2019-05-08 | 2019-05-08 | |
| US62/845,231 | 2019-05-08 | ||
| US16/408,428 | 2019-05-09 | ||
| US16/408,428 US10993928B2 (en) | 2019-04-26 | 2019-05-09 | Compositions comprising non-crystalline forms of cannabidiol |
| US201962860224P | 2019-06-11 | 2019-06-11 | |
| US62/860,224 | 2019-06-11 | ||
| US201962942442P | 2019-12-02 | 2019-12-02 | |
| US62/942,442 | 2019-12-02 | ||
| PCT/US2020/029745 WO2020219829A1 (fr) | 2019-04-26 | 2020-04-24 | Compositions comprenant des formes non cristallines de cannabidiol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3137559A1 true CA3137559A1 (fr) | 2020-10-29 |
Family
ID=72941782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3137559A Pending CA3137559A1 (fr) | 2019-04-26 | 2020-04-24 | Compositions comprenant des formes non cristallines de cannabidiol |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA3137559A1 (fr) |
| WO (1) | WO2020219829A1 (fr) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9085724B2 (en) * | 2010-09-17 | 2015-07-21 | Lubri3ol Oilfield Chemistry LLC | Environmentally friendly base fluids and methods for making and using same |
| WO2016030369A1 (fr) * | 2014-08-25 | 2016-03-03 | Janing Holding Aps | Dispositif avec des compositions pour administration aux poumons, à la muqueuse buccale et au cerveau |
| RU2717782C2 (ru) * | 2015-07-30 | 2020-03-25 | Сумитомо Раббер Индастриз, Лтд. | Резиновая смесь |
| IL301006A (en) * | 2016-03-16 | 2023-04-01 | Buzzelet Development And Technologies Ltd | Cannobinoid compounds are rich in terpenes |
| AU2017242161A1 (en) * | 2016-03-28 | 2018-11-01 | To Pharmaceuticals Llc | Cannabionid and cannabis-based compositions and methods for the treatment of inflammatory conditions of the gastrointestinal tract |
-
2020
- 2020-04-24 WO PCT/US2020/029745 patent/WO2020219829A1/fr active Application Filing
- 2020-04-24 CA CA3137559A patent/CA3137559A1/fr active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2020219829A1 (fr) | 2020-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20240424 |