JP2020529450A5 - - Google Patents
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- Publication number
- JP2020529450A5 JP2020529450A5 JP2020506341A JP2020506341A JP2020529450A5 JP 2020529450 A5 JP2020529450 A5 JP 2020529450A5 JP 2020506341 A JP2020506341 A JP 2020506341A JP 2020506341 A JP2020506341 A JP 2020506341A JP 2020529450 A5 JP2020529450 A5 JP 2020529450A5
- Authority
- JP
- Japan
- Prior art keywords
- crystal
- pentylbenzene
- isopropenyl
- diol
- ene
- 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.)
- Granted
Links
- 239000013078 crystal Substances 0.000 claims 25
- 229910017488 Cu K Inorganic materials 0.000 claims 12
- 229910017541 Cu-K Inorganic materials 0.000 claims 12
- 230000005855 radiation Effects 0.000 claims 12
- 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 11
- 238000000034 method Methods 0.000 claims 6
- 239000000843 powder Substances 0.000 claims 6
- 229960002429 proline Drugs 0.000 claims 5
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 4
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims 3
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims 3
- 229930182821 L-proline Natural products 0.000 claims 3
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims 3
- 229960003237 betaine Drugs 0.000 claims 3
- ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 claims 2
- 229930182820 D-proline Natural products 0.000 claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- CQYBNXGHMBNGCG-FXQIFTODSA-N (2s,3as,7as)-2,3,3a,4,5,6,7,7a-octahydro-1h-indol-1-ium-2-carboxylate Chemical compound C1CCC[C@@H]2[NH2+][C@H](C(=O)[O-])C[C@@H]21 CQYBNXGHMBNGCG-FXQIFTODSA-N 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17382555.5 | 2017-08-07 | ||
| EP17382555 | 2017-08-07 | ||
| PCT/EP2018/071238 WO2019030158A1 (en) | 2017-08-07 | 2018-08-06 | CO-CRYSTAL OF 2 - [(1R, 6R) -6-ISOPROPENYL-3-METHYLCYCLOHEX-2-EN-1-YL] -5-PENTYLBENZENE-1,3-DIOL |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020529450A JP2020529450A (ja) | 2020-10-08 |
| JP2020529450A5 true JP2020529450A5 (https=) | 2021-08-19 |
| JP7186460B2 JP7186460B2 (ja) | 2022-12-09 |
Family
ID=59677166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020506341A Active JP7186460B2 (ja) | 2017-08-07 | 2018-08-06 | ２－［（１ｒ，６ｒ）－６－イソプロペニル－３－メチルシクロヘキサ－２－エン－１－イル］－５－ペンチルベンゼン－１，３－ジオールの共結晶 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US11168047B2 (https=) |
| EP (1) | EP3665145A1 (https=) |
| JP (1) | JP7186460B2 (https=) |
| CN (1) | CN111183127B (https=) |
| CA (1) | CA3107566A1 (https=) |
| WO (1) | WO2019030158A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3085331A1 (en) | 2017-12-11 | 2019-06-20 | Artelo Biosciences, Inc. | New solid forms of cannabidiol and uses thereof |
| US20230381134A1 (en) * | 2020-01-03 | 2023-11-30 | Purisys, Llc | Cocrystals of cannabinoids |
| WO2021234449A1 (en) * | 2020-05-19 | 2021-11-25 | Ebers Tech Inc. | Tetrahydrococannabinolic acid cocrystals |
| CN111792982B (zh) * | 2020-07-10 | 2024-05-14 | 云南农业大学 | 一种易于溶解的块状cbd晶型i及其制备方法 |
| CN113004126B (zh) * | 2021-03-05 | 2022-03-22 | 中国科学院上海药物研究所 | 羟基酪醇甜菜碱共晶，其制备方法及组合物 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2393182B (en) | 2002-09-23 | 2007-03-14 | Gw Pharma Ltd | Method of preparing cannabidiol from plant material |
| CA2548281C (en) | 2003-12-09 | 2013-11-12 | Medcrystalforms, Llc | Method of preparation of mixed phase co-crystals with active agents |
| TWI366460B (en) | 2005-06-16 | 2012-06-21 | Euro Celtique Sa | Cannabinoid active pharmaceutical ingredient for improved dosage forms |
| CN102766128A (zh) | 2005-09-29 | 2012-11-07 | 阿尔巴尼分子研究公司 | δ-9-四氢大麻酚的生成方法 |
| DK2176208T3 (en) | 2007-07-30 | 2015-04-27 | Zynerba Pharmaceuticals Inc | Prodrugs of cannabidiol, compositions containing prodrugs of cannabidiol and methods of use thereof |
| EP2123626A1 (en) | 2008-05-21 | 2009-11-25 | Laboratorios del Dr. Esteve S.A. | Co-crystals of duloxetine and co-crystal formers for the treatment of pain |
| MX2011011445A (es) | 2009-04-29 | 2011-11-18 | Univ Kentucky Res Found | Composiciones que contienen cannabinoides y metodos para su uso. |
| BR112012007364A2 (pt) | 2009-10-23 | 2017-06-06 | Astellas Pharma Inc | composição farmacêutica para administração oral |
| WO2012116349A2 (en) | 2011-02-26 | 2012-08-30 | Amplio Pharma, Llc | Novel cocrystals of ezetimibe |
| EP2842933B1 (de) | 2013-09-03 | 2015-07-29 | Symrise AG | Mischungen cannabinoider Verbindungen, deren Herstellung und Verwendung |
| US10226442B2 (en) * | 2017-07-10 | 2019-03-12 | Syneurx International (Taiwan) Corp. | Lithium salts of N-substituted glycine compounds and uses thereof |
| CA3085331A1 (en) | 2017-12-11 | 2019-06-20 | Artelo Biosciences, Inc. | New solid forms of cannabidiol and uses thereof |
-
2018
- 2018-08-06 EP EP18749373.9A patent/EP3665145A1/en not_active Withdrawn
- 2018-08-06 CN CN201880053149.2A patent/CN111183127B/zh active Active
- 2018-08-06 JP JP2020506341A patent/JP7186460B2/ja active Active
- 2018-08-06 US US16/636,888 patent/US11168047B2/en active Active
- 2018-08-06 WO PCT/EP2018/071238 patent/WO2019030158A1/en not_active Ceased
- 2018-08-06 CA CA3107566A patent/CA3107566A1/en active Pending
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