JP2012507568A5 - - Google Patents
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- Publication number
- JP2012507568A5 JP2012507568A5 JP2011534860A JP2011534860A JP2012507568A5 JP 2012507568 A5 JP2012507568 A5 JP 2012507568A5 JP 2011534860 A JP2011534860 A JP 2011534860A JP 2011534860 A JP2011534860 A JP 2011534860A JP 2012507568 A5 JP2012507568 A5 JP 2012507568A5
- Authority
- JP
- Japan
- Prior art keywords
- amino acid
- thc
- derivative
- composition
- administration
- 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
- 239000000203 mixture Substances 0.000 claims 30
- 238000000034 method Methods 0.000 claims 18
- 235000001014 amino acid Nutrition 0.000 claims 17
- 150000001413 amino acids Chemical class 0.000 claims 13
- ZMFWTUBNIJBJDB-UHFFFAOYSA-N 6-hydroxy-2-methylquinoline-4-carboxylic acid Chemical class C1=C(O)C=CC2=NC(C)=CC(C(O)=O)=C21 ZMFWTUBNIJBJDB-UHFFFAOYSA-N 0.000 claims 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 9
- -1 THC allyl formate derivative Chemical class 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 238000009472 formulation Methods 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims 6
- 150000002148 esters Chemical class 0.000 claims 5
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims 3
- RBHLFWNKEWLHBP-UHFFFAOYSA-N 4-(4-aminophenyl)butanoic acid Chemical compound NC1=CC=C(CCCC(O)=O)C=C1 RBHLFWNKEWLHBP-UHFFFAOYSA-N 0.000 claims 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 3
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 3
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 3
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 3
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 3
- 108010077895 Sarcosine Proteins 0.000 claims 3
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 3
- 235000004279 alanine Nutrition 0.000 claims 3
- 125000000539 amino acid group Chemical group 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 3
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 229940043230 sarcosine Drugs 0.000 claims 3
- 229940014800 succinic anhydride Drugs 0.000 claims 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 3
- 239000004474 valine Substances 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- GOLXRNDWAUTYKT-UHFFFAOYSA-N 3-(1H-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)=CNC2=C1 GOLXRNDWAUTYKT-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11016508P | 2008-10-31 | 2008-10-31 | |
| US61/110,165 | 2008-10-31 | ||
| PCT/US2009/062998 WO2010051541A2 (en) | 2008-10-31 | 2009-11-02 | Compositions containing delta-9-thc-amino acid esters and process of preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012507568A JP2012507568A (ja) | 2012-03-29 |
| JP2012507568A5 true JP2012507568A5 (enExample) | 2012-12-20 |
| JP5739344B2 JP5739344B2 (ja) | 2015-06-24 |
Family
ID=42129588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011534860A Active JP5739344B2 (ja) | 2008-10-31 | 2009-11-02 | Δ−９−ｔｈｃ−アミノ酸エステルを含む組成物及び調製方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8809261B2 (enExample) |
| EP (1) | EP2352497B1 (enExample) |
| JP (1) | JP5739344B2 (enExample) |
| AU (1) | AU2009308665B2 (enExample) |
| CA (1) | CA2741862C (enExample) |
| DK (1) | DK2352497T3 (enExample) |
| ES (1) | ES2622582T3 (enExample) |
| HU (1) | HUE032158T2 (enExample) |
| PL (1) | PL2352497T3 (enExample) |
| WO (1) | WO2010051541A2 (enExample) |
Families Citing this family (72)
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| US20160345631A1 (en) | 2005-07-19 | 2016-12-01 | James Monsees | Portable devices for generating an inhalable vapor |
| US8991402B2 (en) | 2007-12-18 | 2015-03-31 | Pax Labs, Inc. | Aerosol devices and methods for inhaling a substance and uses thereof |
| WO2010051541A2 (en) * | 2008-10-31 | 2010-05-06 | The University Of Mississippi | Compositions containing delta-9-thc-amino acid esters and process of preparation |
| BR112012023421B1 (pt) | 2010-03-17 | 2021-09-14 | Novaliq Gmbh | Composição farmacêutica para tratamento de aumento de pressão intraocular |
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| WO2014041071A1 (en) | 2012-09-12 | 2014-03-20 | Novaliq Gmbh | Semifluorinated alkane compositions |
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| WO2014182736A1 (en) | 2013-05-06 | 2014-11-13 | Ploom, Inc. | Nicotine salt formulations for aerosol devices and methods thereof |
| IL295735B2 (en) | 2013-12-05 | 2024-04-01 | Juul Labs Inc | Nicotine liquid formulations for aerosol devices and methods thereof |
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| USD842536S1 (en) | 2016-07-28 | 2019-03-05 | Juul Labs, Inc. | Vaporizer cartridge |
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| GB2531282A (en) | 2014-10-14 | 2016-04-20 | Gw Pharma Ltd | Use of cannabinoids in the treatment of epilepsy |
| KR102682702B1 (ko) | 2014-12-05 | 2024-07-09 | 쥴 랩스, 인크. | 교정된 투여량 제어 |
| AU2016231788A1 (en) * | 2015-03-19 | 2017-10-12 | One World Cannabis Ltd | Preparations of cannabis emulsions and methods thereof |
| CN105037180B (zh) * | 2015-04-19 | 2017-10-10 | 安徽省逸欣铭医药科技有限公司 | 一种双重作用的中枢性镇痛新化合物、制备方法及用途 |
| EP3297617A4 (en) * | 2015-05-18 | 2019-02-20 | 5071, Inc. | HOMOGENEOUS CANNABIC COMPOSITION AND METHOD FOR THE MANUFACTURE THEREOF |
| WO2016186735A1 (en) | 2015-05-18 | 2016-11-24 | 5071, Inc. | Homogenous cannabis compositions and methods of making the same |
| GB2539472A (en) | 2015-06-17 | 2016-12-21 | Gw Res Ltd | Use of cannabinoids in the treatment of epilepsy |
| DK3495023T3 (da) | 2015-09-30 | 2020-07-20 | Novaliq Gmbh | Semifluorerede forbindelser og sammensætninger deraf |
| EP4234523A1 (en) | 2015-09-30 | 2023-08-30 | Novaliq GmbH | Semifluorinated compounds for ophthalmic administration |
| NZ745595A (en) | 2016-01-29 | 2019-12-20 | Univ Mississippi | Biologically active cannabidiol analogs |
| EP3413960B1 (en) | 2016-02-11 | 2021-03-31 | Juul Labs, Inc. | Fillable vaporizer cartridge and method of filling |
| BR112018016402B1 (pt) | 2016-02-11 | 2023-12-19 | Juul Labs, Inc | Cartuchos de fixação segura para dispositivos vaporizadores |
| US10405582B2 (en) | 2016-03-10 | 2019-09-10 | Pax Labs, Inc. | Vaporization device with lip sensing |
| JP2019511580A (ja) * | 2016-04-15 | 2019-04-25 | エスアールイー ウェルネス インク．Ｓｒｅ Ｗｅｌｌｎｅｓｓ Ｉｎｃ． | 乳化剤を使用して大麻油を親水性にする方法及び関連するカンナビノイド組成物 |
| US20220087972A9 (en) | 2016-04-15 | 2022-03-24 | Sre Wellness, Inc. | Cannabinoid Compositions |
| WO2017180948A1 (en) | 2016-04-15 | 2017-10-19 | Ronald Silver | Cannabinoid and caffeine emulsifications |
| USD849996S1 (en) | 2016-06-16 | 2019-05-28 | Pax Labs, Inc. | Vaporizer cartridge |
| JP2019523228A (ja) * | 2016-06-16 | 2019-08-22 | ティーウィノット テクノロジーズ リミテッド | カンナビノイドプロドラッグの製造のための方法、薬学的製剤、およびその使用 |
| USD851830S1 (en) | 2016-06-23 | 2019-06-18 | Pax Labs, Inc. | Combined vaporizer tamp and pick tool |
| USD836541S1 (en) | 2016-06-23 | 2018-12-25 | Pax Labs, Inc. | Charging device |
| USD848057S1 (en) | 2016-06-23 | 2019-05-07 | Pax Labs, Inc. | Lid for a vaporizer |
| US11660403B2 (en) | 2016-09-22 | 2023-05-30 | Juul Labs, Inc. | Leak-resistant vaporizer device |
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| MX2019011980A (es) * | 2017-04-05 | 2020-07-29 | Univ Mississippi | Aislamiento de cannabinoides puros a partir de cannabis. |
| ES2957559T3 (es) | 2017-04-21 | 2024-01-22 | Dermaliq Therapeutics Inc | Composiciones de yodo |
| US11278503B2 (en) | 2017-05-12 | 2022-03-22 | Novaliq Gmbh | Pharmaceutical compositions comprising semifluorinated alkanes for the treatment of contact lense-related conditions |
| GB2564383B (en) | 2017-06-23 | 2021-04-21 | Gw Res Ltd | Use of cannabidiol in the treatment of tumours assoicated with Tuberous Sclerosis Complex |
| EP3424494A1 (en) * | 2017-07-07 | 2019-01-09 | SolMic Research GmbH | Stable cannabinoid compositions |
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| EP4356965A3 (en) * | 2017-07-14 | 2024-07-17 | 5071, Inc. | Cannabinoid compositions and methods of preparation thereof |
| CA3072768C (en) * | 2017-08-27 | 2024-06-11 | Rhodes Technologies | Pharmaceutical compositions for the treatment of ophthalmic conditions |
| USD887632S1 (en) | 2017-09-14 | 2020-06-16 | Pax Labs, Inc. | Vaporizer cartridge |
| CN111372566A (zh) | 2017-09-27 | 2020-07-03 | 诺瓦利克有限责任公司 | 用于治疗眼部疾病的包含拉坦前列素的眼科用组合物 |
| CN119909046A (zh) | 2017-10-04 | 2025-05-02 | 诺瓦利克有限责任公司 | 包含f6h8的眼用组合物 |
| CA3083622A1 (en) * | 2017-11-27 | 2019-05-31 | Beleave Inc. | Extraction and purification of cannabinoid compounds |
| GB2568929A (en) | 2017-12-01 | 2019-06-05 | Gw Res Ltd | Use of cannabinoids in the treatment of epilepsy |
| GB201806953D0 (en) | 2018-04-27 | 2018-06-13 | Gw Res Ltd | Cannabidiol Preparations |
| WO2019206956A1 (en) | 2018-04-27 | 2019-10-31 | Novaliq Gmbh | Ophthalmic compositions comprising tafluprost for the treatment of glaucoma |
| WO2020074697A1 (en) | 2018-10-12 | 2020-04-16 | Novaliq Gmbh | Ophthalmic composition for treatment of dry eye disease |
| EP3876907A4 (en) * | 2018-11-07 | 2022-08-10 | Columbia Care LLC | CANNABINOID SUPPOSITORY FORMULATIONS |
| US20200254104A1 (en) * | 2019-02-11 | 2020-08-13 | John CHANCEY | Methods of making and using phytocannabinoids complexed with a protein, peptide, amino acid, polysaccharide, disacchride, or monosaccharide |
| EP3923907B1 (en) | 2019-02-13 | 2024-09-25 | Novaliq GmbH | Compositions and methods for the treatment of ocular neovascularization |
| CA3132861A1 (en) * | 2019-03-12 | 2020-09-17 | 6th Wave Innovations Corp. | Molecularly imprinted polymers for extraction of cannabinoids and uses thereof |
| WO2020209902A1 (en) * | 2019-04-09 | 2020-10-15 | Village Flora, Inc. | Methods and compositions for use in treatment of cancer without psychoactive effects |
| GB202002754D0 (en) | 2020-02-27 | 2020-04-15 | Gw Res Ltd | Methods of treating tuberous sclerosis complex with cannabidiol and everolimus |
| CN115867533B (zh) | 2020-06-30 | 2024-07-23 | 加拿大瑞安神经科学公司 | 色胺前药 |
| CA3204196A1 (en) * | 2020-11-06 | 2022-05-12 | Zelira Therapeutics Operations Pty Ltd | Cannabinoid encapsulation technology |
| 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 |
| US11352337B1 (en) * | 2021-06-02 | 2022-06-07 | Acid Neutral Alkaline Laboratory | Zeolite catalyst and method for preparation of aromatic tricyclic pyrans |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB313977A (en) * | 1927-12-21 | 1929-06-21 | British United Shoe Machinery | Improvements in or relating to boot or shoe sewing machines or methods of making boots or shoes by the use thereof |
| JPS5518709B2 (enExample) | 1970-02-13 | 1980-05-21 | ||
| US4933363A (en) * | 1988-08-16 | 1990-06-12 | Elsohly Mahmoud A | Method for effecting systemic delivery of delta-9-tetrahydrocannabinol |
| US6040298A (en) * | 1992-12-23 | 2000-03-21 | Oclassen Pharmaceuticals, Inc. | Methods for treatment with compositions effective against acyclovir-resistant strains of herpes viruses |
| US5389375A (en) * | 1993-05-21 | 1995-02-14 | University Of Mississippi | Stable suppository formulations effecting bioavailability of Δ9 -thc |
| US5631297A (en) * | 1994-07-11 | 1997-05-20 | Pate; David W. | Anandamides useful for the treatment of intraocular hypertension, ophthalmic compositions containing the same and methods of use of the same |
| US6008383A (en) * | 1998-10-26 | 1999-12-28 | University Of Mississippi | Method of preparing delta-9-tetrahydrocannabinol esters |
| US20060078955A1 (en) * | 2004-10-13 | 2006-04-13 | Lin-Zhi International | Method for retrieving delta9-THC from oral fluid |
| CA2586064A1 (en) * | 2004-11-02 | 2006-05-11 | New River Pharmaceuticals Inc. | Prodrugs of ribavirin with improved hepatic delivery |
| CN101516333A (zh) * | 2006-08-04 | 2009-08-26 | 英西斯治疗学股份有限公司 | 水性屈大麻酚制剂 |
| US20080306285A1 (en) | 2007-04-27 | 2008-12-11 | Alexza Pharmaceuticals, Inc. | Heat-Labile Prodrugs |
| CA2990445C (en) * | 2007-08-21 | 2020-05-05 | Board Of Regents, The University Of Texas System | Thermo-kinetic mixing for pharmaceutical applications |
| EP2211760A4 (en) * | 2007-10-17 | 2013-09-18 | Axxia Pharmaceuticals Llc | POLYMER DRUG DELIVERY SYSTEMS AND METHODS OF EXTRUSION OF THERMOPLASTIC COMPOUNDS TO PRODUCE THESE SYSTEMS |
| CA2977722C (en) * | 2007-11-30 | 2020-12-29 | Zynerba Pharmaceuticals, Inc. | Prodrugs of tetrahydrocannabinol, compositions comprising prodrugs of tetrahydrocannabinol and methods of using the same |
| US20090169629A1 (en) * | 2008-01-02 | 2009-07-02 | Novagali Pharma Sa | Micellar compositions with ophthalmic applications |
| EP2151234A1 (en) * | 2008-07-28 | 2010-02-10 | Laboratorios Del. Dr. Esteve, S.A. | Pharmaceutical formulation comprising a CB1-receptor compound in a solid solution and/or solid dispersion |
| WO2010051541A2 (en) * | 2008-10-31 | 2010-05-06 | The University Of Mississippi | Compositions containing delta-9-thc-amino acid esters and process of preparation |
-
2009
- 2009-11-02 WO PCT/US2009/062998 patent/WO2010051541A2/en not_active Ceased
- 2009-11-02 US US13/126,606 patent/US8809261B2/en active Active
- 2009-11-02 JP JP2011534860A patent/JP5739344B2/ja active Active
- 2009-11-02 AU AU2009308665A patent/AU2009308665B2/en active Active
- 2009-11-02 PL PL09824226T patent/PL2352497T3/pl unknown
- 2009-11-02 CA CA2741862A patent/CA2741862C/en active Active
- 2009-11-02 EP EP09824226.6A patent/EP2352497B1/en active Active
- 2009-11-02 HU HUE09824226A patent/HUE032158T2/en unknown
- 2009-11-02 DK DK09824226.6T patent/DK2352497T3/en active
- 2009-11-02 ES ES09824226.6T patent/ES2622582T3/es active Active
-
2014
- 2014-08-18 US US14/462,482 patent/US9630941B2/en active Active
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