CO2018001290A2 - Proceso para la producción de cannabidiol y delta-9-tetrahidrocannabinol - Google Patents
Proceso para la producción de cannabidiol y delta-9-tetrahidrocannabinolInfo
- Publication number
- CO2018001290A2 CO2018001290A2 CONC2018/0001290A CO2018001290A CO2018001290A2 CO 2018001290 A2 CO2018001290 A2 CO 2018001290A2 CO 2018001290 A CO2018001290 A CO 2018001290A CO 2018001290 A2 CO2018001290 A2 CO 2018001290A2
- Authority
- CO
- Colombia
- Prior art keywords
- cannabidiol
- compound
- derivative
- tetrahydrocannabinol
- delta
- Prior art date
Links
- 229950011318 cannabidiol Drugs 0.000 title abstract 6
- 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 abstract 5
- 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 abstract 5
- 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 abstract 5
- 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 abstract 4
- XXGMIHXASFDFSM-UHFFFAOYSA-N Delta9-tetrahydrocannabinol Natural products CCCCCc1cc2OC(C)(C)C3CCC(=CC3c2c(O)c1O)C XXGMIHXASFDFSM-UHFFFAOYSA-N 0.000 title 1
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 title 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 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 cannabidiol compound Chemical class 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- 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
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
RESUMEN La presente descripción se refiere a la preparación de un compuesto de cannabidiol o un derivado del mismo. El compuesto de cannabidiol o un derivado del mismo se puede preparar por medio de una reacción catalizada con ácido de un di-halo-olivetol seleccionado y sustituido adecuadamente o derivado del mismo con un alqueno cíclico seleccionado y sustituido adecuadamente para producir un compuesto de dihalo-cannabidiol o derivado del mismo. El compuesto de dihalo-cannabidiol o derivado del mismo se puede producir con alto rendimiento, alta estereoespecificidad o ambos. Luego se puede convertir en condiciones reductoras a un compuesto de cannabidiol o derivados del mismo.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562191097P | 2015-07-10 | 2015-07-10 | |
| US15/199,528 US10059683B2 (en) | 2015-07-10 | 2016-06-30 | Process for the production of cannabidiol and delta-9-tetrahydrocannabinol |
| PCT/US2016/040635 WO2017011210A1 (en) | 2015-07-10 | 2016-07-01 | Process for the production of cannabidiol and delta-9-tetrahydrocannabinol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CO2018001290A2 true CO2018001290A2 (es) | 2018-04-19 |
Family
ID=57730761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CONC2018/0001290A CO2018001290A2 (es) | 2015-07-10 | 2018-02-08 | Proceso para la producción de cannabidiol y delta-9-tetrahidrocannabinol |
Country Status (21)
| Country | Link |
|---|---|
| US (4) | US10059683B2 (es) |
| EP (2) | EP3319952B8 (es) |
| JP (2) | JP6810842B2 (es) |
| CN (1) | CN108137526A (es) |
| AU (2) | AU2016294264B2 (es) |
| BR (1) | BR112018000497A2 (es) |
| CA (1) | CA2992043C (es) |
| CL (2) | CL2018000079A1 (es) |
| CO (1) | CO2018001290A2 (es) |
| CR (1) | CR20180094A (es) |
| DK (1) | DK3319952T3 (es) |
| EC (1) | ECSP18010065A (es) |
| ES (2) | ES3010714T3 (es) |
| HK (1) | HK1255390A1 (es) |
| IL (1) | IL256750A (es) |
| MX (1) | MX2018000354A (es) |
| MY (1) | MY182971A (es) |
| NZ (1) | NZ738925A (es) |
| PH (1) | PH12018500093A1 (es) |
| PT (1) | PT3319952T (es) |
| WO (1) | WO2017011210A1 (es) |
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| GB2530001B (en) | 2014-06-17 | 2019-01-16 | Gw Pharma Ltd | Use of cannabidiol in the reduction of convulsive seizure frequency in treatment-resistant epilepsy |
| GB2531281A (en) | 2014-10-14 | 2016-04-20 | Gw Pharma Ltd | Use of cannabidiol in the treatment of intractable epilepsy |
| GB2531282A (en) | 2014-10-14 | 2016-04-20 | Gw Pharma Ltd | Use of cannabinoids in the treatment of epilepsy |
| GB2539472A (en) | 2015-06-17 | 2016-12-21 | Gw Res Ltd | Use of cannabinoids in the treatment of epilepsy |
| US10059683B2 (en) * | 2015-07-10 | 2018-08-28 | Noramco, Inc. | Process for the production of cannabidiol and delta-9-tetrahydrocannabinol |
| US10239808B1 (en) | 2016-12-07 | 2019-03-26 | Canopy Holdings, LLC | Cannabis extracts |
| GB2564383B (en) | 2017-06-23 | 2021-04-21 | Gw Res Ltd | Use of cannabidiol in the treatment of tumours assoicated with Tuberous Sclerosis Complex |
| US10640482B2 (en) | 2017-07-21 | 2020-05-05 | University Of South Florida | Synthesis of cannabinoids |
| GB2568929A (en) | 2017-12-01 | 2019-06-05 | Gw Res Ltd | Use of cannabinoids in the treatment of epilepsy |
| EP3745884A1 (en) | 2018-01-31 | 2020-12-09 | Canopy Holdings, Llc | Hemp powder |
| JP2021513553A (ja) * | 2018-02-13 | 2021-05-27 | ビートルバング ファーマ リミテッド | カンナビノイド誘導体並びにそのコンジュゲート及びその使用 |
| CN113264914A (zh) | 2018-02-20 | 2021-08-17 | 麦姆德制药(佛罗里达)公司 | 用于治疗物质成瘾和其它障碍的遗传修饰的大麻植物和修饰的大麻素化合物 |
| CN112292368B (zh) | 2018-06-28 | 2024-02-02 | 西姆莱斯有限公司 | （+）-大麻素类的合成及其治疗作用 |
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| JP2021535202A (ja) * | 2018-08-20 | 2021-12-16 | ベッソール ファルマ、エルエルシー | 新規カンナビノイドおよびカンナビノイド酸ならびにそれらの誘導体 |
| AU2019335372B2 (en) * | 2018-09-05 | 2024-12-12 | Purisys Llc | Cannabidiol compositions having modified cannabinoid profiles |
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| CN109970516A (zh) * | 2019-03-20 | 2019-07-05 | 栾云鹏 | 一种工业化制备高纯度高收率的大麻酚类物质的合成方法 |
| WO2020214574A1 (en) | 2019-04-15 | 2020-10-22 | Trustees Of Boston University | One-step flow-mediated synthesis of cannabidiol (cbd) and derivatives |
| 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 |
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| US20230183157A1 (en) * | 2019-05-31 | 2023-06-15 | Purisys Llc | Processes for the preparation of halogenated dihydroxybenzene compounds |
| CA3142957A1 (en) | 2019-06-11 | 2020-12-17 | Canopy Growth Corporation | Improved methods for converting cannabidiol into delta8-tetrahydrocannabinol |
| EP4067330B1 (en) | 2019-06-11 | 2024-03-20 | Symrise AG | Cosmetic use of cannabigerol |
| WO2020252277A1 (en) * | 2019-06-13 | 2020-12-17 | Isomerz, Inc. | Making delta 8 thc, delta 10 thc and/or cannabinol from cbd |
| WO2020252369A1 (en) * | 2019-06-14 | 2020-12-17 | Purisys Llc | Crystalline cannabigerol |
| GB201910389D0 (en) | 2019-07-19 | 2019-09-04 | Gw Pharma Ltd | Novel compounds, methods for their manufacture, and uses thereof |
| 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 |
| CA3163788A1 (en) | 2019-12-06 | 2021-06-10 | JLABS Beauty LLC | Topical compositions containing rose oil and cannabidiol and methods of making and using the same |
| CN115066238A (zh) * | 2019-12-27 | 2022-09-16 | 海湾医学公司 | 大麻色原烯和相关大麻素的制备 |
| EP4088723B1 (en) * | 2020-01-08 | 2025-08-06 | Chengdu Baiyu Pharmaceutical Co., Ltd. | Cannabidiol derivative, and preparation method therefor and medical use thereof |
| CN113087743B (zh) * | 2020-01-08 | 2023-04-28 | 成都百裕制药股份有限公司 | 四氢大麻酚衍生物及其制备方法和在医药上的应用 |
| CN113087599A (zh) * | 2020-01-08 | 2021-07-09 | 成都百裕制药股份有限公司 | 大麻二酚衍生物及其制备方法和在医药上的应用 |
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| US10981849B1 (en) * | 2020-02-20 | 2021-04-20 | Sci Pharmtech Inc. | Method for preparing cannabinoids |
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| CN112811980B (zh) * | 2020-12-01 | 2022-03-25 | 山东金城金奥医药科技有限公司 | 一种绿色光氧化连续制备大麻二酚中间体的方法 |
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| US11242330B1 (en) * | 2021-02-25 | 2022-02-08 | Acid Neutral Alkaline Laboratory | Organic catalyst and method for preparation of aromatic tricyclic pyrans |
| US11242328B1 (en) * | 2021-02-25 | 2022-02-08 | Acid Neutral Alkaline Laboratory | Heterogeneous catalyst and method for preparation of aromatic tricyclic pyrans |
| US20220306598A1 (en) * | 2021-03-25 | 2022-09-29 | Precision Extraction Corporation | Method for highly selective conversion of cbd to delta-8 thc |
| GB2628746A (en) * | 2021-03-31 | 2024-10-02 | Phytotherapeutix Ltd | Terpenophenolic compounds and their use |
| US11352337B1 (en) * | 2021-06-02 | 2022-06-07 | Acid Neutral Alkaline Laboratory | Zeolite catalyst and method for preparation of aromatic tricyclic pyrans |
| CN113603568A (zh) * | 2021-07-19 | 2021-11-05 | 厦门朝阳生物工程有限公司 | 一种大麻二酚的制备方法 |
| WO2023086447A2 (en) * | 2021-11-12 | 2023-05-19 | Pureform Global, Inc. | A method for the synthesis of cannabinol |
| 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 |
| AU2023322302A1 (en) | 2022-08-11 | 2025-05-22 | Cardiol Therapeutics Inc. | Stable injectable cannabidiol formulations |
| CN117700304A (zh) * | 2022-09-01 | 2024-03-15 | 卡那比生物科学有限公司 | 一种大麻二酚的制备方法及其应用 |
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| 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 |
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| US10059683B2 (en) * | 2015-07-10 | 2018-08-28 | Noramco, Inc. | Process for the production of cannabidiol and delta-9-tetrahydrocannabinol |
-
2016
- 2016-06-30 US US15/199,528 patent/US10059683B2/en active Active
- 2016-06-30 US US15/197,929 patent/US20170008869A1/en not_active Abandoned
- 2016-07-01 DK DK16741447.3T patent/DK3319952T3/da active
- 2016-07-01 ES ES20155338T patent/ES3010714T3/es active Active
- 2016-07-01 ES ES16741447T patent/ES2784881T3/es active Active
- 2016-07-01 BR BR112018000497A patent/BR112018000497A2/pt not_active Application Discontinuation
- 2016-07-01 MY MYPI2018700102A patent/MY182971A/en unknown
- 2016-07-01 JP JP2018520383A patent/JP6810842B2/ja active Active
- 2016-07-01 WO PCT/US2016/040635 patent/WO2017011210A1/en not_active Ceased
- 2016-07-01 CR CR20180094A patent/CR20180094A/es unknown
- 2016-07-01 EP EP16741447.3A patent/EP3319952B8/en active Active
- 2016-07-01 CA CA2992043A patent/CA2992043C/en active Active
- 2016-07-01 AU AU2016294264A patent/AU2016294264B2/en active Active
- 2016-07-01 PT PT167414473T patent/PT3319952T/pt unknown
- 2016-07-01 MX MX2018000354A patent/MX2018000354A/es unknown
- 2016-07-01 NZ NZ738925A patent/NZ738925A/en unknown
- 2016-07-01 HK HK18114529.1A patent/HK1255390A1/zh unknown
- 2016-07-01 CN CN201680045030.1A patent/CN108137526A/zh active Pending
- 2016-07-01 EP EP20155338.5A patent/EP3722276B1/en active Active
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2018
- 2018-01-07 IL IL256750A patent/IL256750A/en unknown
- 2018-01-10 CL CL2018000079A patent/CL2018000079A1/es unknown
- 2018-01-10 PH PH12018500093A patent/PH12018500093A1/en unknown
- 2018-02-08 CO CONC2018/0001290A patent/CO2018001290A2/es unknown
- 2018-02-09 EC ECIEPI201810065A patent/ECSP18010065A/es unknown
- 2018-07-13 US US16/034,876 patent/US10844035B2/en active Active
-
2019
- 2019-09-13 AU AU2019229416A patent/AU2019229416A1/en not_active Abandoned
- 2019-11-04 CL CL2019003154A patent/CL2019003154A1/es unknown
- 2019-12-11 JP JP2019223998A patent/JP2020037596A/ja not_active Withdrawn
-
2020
- 2020-11-17 US US16/950,357 patent/US20210061781A1/en active Pending
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