JP2016509842A5 - - Google Patents
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- JP2016509842A5 JP2016509842A5 JP2015560302A JP2015560302A JP2016509842A5 JP 2016509842 A5 JP2016509842 A5 JP 2016509842A5 JP 2015560302 A JP2015560302 A JP 2015560302A JP 2015560302 A JP2015560302 A JP 2015560302A JP 2016509842 A5 JP2016509842 A5 JP 2016509842A5
- Authority
- JP
- Japan
- Prior art keywords
- synthase
- acid
- thca
- cbda
- cbca
- 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.)
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- 238000000034 method Methods 0.000 claims 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 18
- 101000712615 Cannabis sativa Tetrahydrocannabinolic acid synthase Proteins 0.000 claims 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 12
- 239000011541 reaction mixture Substances 0.000 claims 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 9
- WVOLTBSCXRRQFR-DLBZAZTESA-N cannabidiolic acid Chemical compound OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-DLBZAZTESA-N 0.000 claims 9
- 229930003827 cannabinoid Natural products 0.000 claims 9
- 239000003557 cannabinoid Substances 0.000 claims 9
- 108010075293 Cannabidiolic acid synthase Proteins 0.000 claims 8
- UCONUSSAWGCZMV-HZPDHXFCSA-N Delta(9)-tetrahydrocannabinolic acid Chemical compound C([C@H]1C(C)(C)O2)CC(C)=C[C@H]1C1=C2C=C(CCCCC)C(C(O)=O)=C1O UCONUSSAWGCZMV-HZPDHXFCSA-N 0.000 claims 7
- HRHJHXJQMNWQTF-UHFFFAOYSA-N cannabichromenic acid Chemical compound O1C(C)(CCC=C(C)C)C=CC2=C1C=C(CCCCC)C(C(O)=O)=C2O HRHJHXJQMNWQTF-UHFFFAOYSA-N 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- WVOLTBSCXRRQFR-SJORKVTESA-N Cannabidiolic acid Natural products OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@@H]1[C@@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-SJORKVTESA-N 0.000 claims 3
- 229920000858 Cyclodextrin Polymers 0.000 claims 3
- 241000588724 Escherichia coli Species 0.000 claims 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims 3
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- 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 2
- 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 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- KTPDAZGMXXWSMU-UHFFFAOYSA-N Cannabichromen Natural products CCCCc1cc(O)c2C=CC(C)(CCC=C(C)C)Oc2c1 KTPDAZGMXXWSMU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 claims 1
- 108030003705 Tetrahydrocannabinolic acid synthases Proteins 0.000 claims 1
- 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 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
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 claims 1
- WVOLTBSCXRRQFR-DLBZAZTESA-M cannabidiolate Chemical compound OC1=C(C([O-])=O)C(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-DLBZAZTESA-M 0.000 claims 1
- SEEZIOZEUUMJME-FOWTUZBSSA-N cannabigerolic acid Chemical compound CCCCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1C(O)=O SEEZIOZEUUMJME-FOWTUZBSSA-N 0.000 claims 1
- 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 1
- 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 claims 1
- 229960004242 dronabinol Drugs 0.000 claims 1
- 230000003100 immobilizing effect Effects 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361770766P | 2013-02-28 | 2013-02-28 | |
| US61/770,766 | 2013-02-28 | ||
| PCT/US2014/018944 WO2014134281A1 (en) | 2013-02-28 | 2014-02-27 | Biosynthesis of cannabinoids |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018025851A Division JP6724052B2 (ja) | 2013-02-28 | 2018-02-16 | カンナビノイドの生合成 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016509842A JP2016509842A (ja) | 2016-04-04 |
| JP2016509842A5 true JP2016509842A5 (https=) | 2017-02-16 |
| JP6581509B2 JP6581509B2 (ja) | 2019-09-25 |
Family
ID=51428796
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015560302A Expired - Fee Related JP6581509B2 (ja) | 2013-02-28 | 2014-02-27 | 化合物を合成する化学工学プロセス及び装置 |
| JP2018025851A Expired - Fee Related JP6724052B2 (ja) | 2013-02-28 | 2018-02-16 | カンナビノイドの生合成 |
| JP2019205366A Pending JP2020022507A (ja) | 2013-02-28 | 2019-11-13 | カンナビノイドの生合成 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018025851A Expired - Fee Related JP6724052B2 (ja) | 2013-02-28 | 2018-02-16 | カンナビノイドの生合成 |
| JP2019205366A Pending JP2020022507A (ja) | 2013-02-28 | 2019-11-13 | カンナビノイドの生合成 |
Country Status (9)
| Country | Link |
|---|---|
| US (8) | US9359625B2 (https=) |
| EP (1) | EP2961402B1 (https=) |
| JP (3) | JP6581509B2 (https=) |
| CN (1) | CN105555265A (https=) |
| AU (2) | AU2014223458A1 (https=) |
| BR (1) | BR112015020332A2 (https=) |
| CA (2) | CA3012383C (https=) |
| IL (1) | IL240830B (https=) |
| WO (1) | WO2014134281A1 (https=) |
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| US9326967B2 (en) | 2013-08-22 | 2016-05-03 | Stephen C. Perry | Vaporizable cannabinoid compositions |
| US9655910B2 (en) | 2014-03-21 | 2017-05-23 | Bodybio Inc. | Compositions and methods for treating addiction |
| EP3171872B1 (en) * | 2014-07-21 | 2020-11-11 | Glia, LLC | Method for treating radiotherapy-and-chemotherapy associated cognitive or emotional impairment with cannabinoids |
| US9394510B2 (en) | 2014-08-25 | 2016-07-19 | Full Spectrum Laboratories Limited | Apparatus and methods for the simultaneous production of compounds |
| AU2018260710B2 (en) * | 2017-04-26 | 2022-07-21 | Teewinot Technologies Limited | Apparatus, methods and composition for synthesis of cannabinoid compounds |
-
2014
- 2014-02-27 WO PCT/US2014/018944 patent/WO2014134281A1/en not_active Ceased
- 2014-02-27 CA CA3012383A patent/CA3012383C/en active Active
- 2014-02-27 CA CA2902452A patent/CA2902452C/en active Active
- 2014-02-27 BR BR112015020332A patent/BR112015020332A2/pt not_active IP Right Cessation
- 2014-02-27 JP JP2015560302A patent/JP6581509B2/ja not_active Expired - Fee Related
- 2014-02-27 AU AU2014223458A patent/AU2014223458A1/en not_active Abandoned
- 2014-02-27 EP EP14757297.8A patent/EP2961402B1/en active Active
- 2014-02-27 IL IL240830A patent/IL240830B/en unknown
- 2014-02-27 CN CN201480023902.5A patent/CN105555265A/zh active Pending
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2015
- 2015-08-26 US US14/836,339 patent/US9359625B2/en active Active
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2016
- 2016-06-02 US US15/171,517 patent/US9526715B1/en not_active Expired - Fee Related
- 2016-08-19 US US15/242,189 patent/US9861609B2/en not_active Expired - Fee Related
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2017
- 2017-02-10 US US15/430,122 patent/US10081818B2/en active Active
- 2017-02-23 US US15/441,109 patent/US20170159080A1/en not_active Abandoned
- 2017-05-12 US US15/594,348 patent/US10214753B2/en active Active
- 2017-09-22 US US15/713,304 patent/US10472652B2/en active Active
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2018
- 2018-02-16 JP JP2018025851A patent/JP6724052B2/ja not_active Expired - Fee Related
- 2018-09-10 AU AU2018228329A patent/AU2018228329A1/en not_active Abandoned
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2019
- 2019-10-15 US US16/601,984 patent/US20200048664A1/en not_active Abandoned
- 2019-11-13 JP JP2019205366A patent/JP2020022507A/ja active Pending
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