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 (OSRAM) | 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 (OSRAM) |
| EP (1) | EP2352497B1 (OSRAM) |
| JP (1) | JP5739344B2 (OSRAM) |
| AU (1) | AU2009308665B2 (OSRAM) |
| CA (1) | CA2741862C (OSRAM) |
| DK (1) | DK2352497T3 (OSRAM) |
| ES (1) | ES2622582T3 (OSRAM) |
| HU (1) | HUE032158T2 (OSRAM) |
| PL (1) | PL2352497T3 (OSRAM) |
| WO (1) | WO2010051541A2 (OSRAM) |
Families Citing this family (72)
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| ES2622582T3 (es) * | 2008-10-31 | 2017-07-06 | University Of Mississippi | Proceso para la preparación de ésteres de delta-9-THC-aminoácido |
| MX2012010684A (es) | 2010-03-17 | 2012-11-06 | Novaliq Gmbh | Composicion farmaceutica para el tratamiento de la presion intraocular incrementada. |
| US10517530B2 (en) | 2012-08-28 | 2019-12-31 | Juul Labs, Inc. | Methods and devices for delivering and monitoring of tobacco, nicotine, or other substances |
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| BR112015004997B1 (pt) | 2012-09-12 | 2022-09-13 | Novaliq Gmbh | Composições oftálmicas contendo misturas de alcanos semifluorados |
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| IL305842B2 (en) | 2013-05-06 | 2024-12-01 | Juul Labs Inc | Nicotine salt formulations for aerosol devices and methods thereof |
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| EP3160445B1 (en) | 2014-06-26 | 2021-10-20 | Island Breeze Systems Ca, LLC | Mdi related products and methods of use |
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| KR102755161B1 (ko) | 2014-12-05 | 2025-01-15 | 쥴 랩스, 인크. | 교정된 투여량 제어 |
| CA2982250A1 (en) * | 2015-03-19 | 2016-09-22 | 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 |
| WO2017055453A1 (en) | 2015-09-30 | 2017-04-06 | Novaliq Gmbh | Semifluorinated compounds for ophthalmic administration |
| CN110403923B (zh) | 2015-09-30 | 2021-09-21 | 诺瓦利克有限责任公司 | 半氟化化合物和其组合物 |
| JP6676176B2 (ja) * | 2016-01-29 | 2020-04-08 | ユニヴァーシティー オブ ミシシッピ | 生物学的に活性なカンナビジオール類似体 |
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| CA3021095A1 (en) | 2016-04-15 | 2017-10-19 | Sre Wellness Inc. | Method of making cannabis oil hydrophiilic using emulsifiers and related cannabinoid compositions |
| US20220087972A9 (en) | 2016-04-15 | 2022-03-24 | Sre Wellness, Inc. | Cannabinoid Compositions |
| CA3021093A1 (en) * | 2016-04-15 | 2017-10-19 | Sre Wellness, Inc. | Cannabis infused sweeteners and other compositions |
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| EP3472142A1 (en) * | 2016-06-16 | 2019-04-24 | Teewinot Technologies Limited | Methods for the manufacture of cannabinoid prodrugs, pharmaceutical formulations and their use |
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| USD848057S1 (en) | 2016-06-23 | 2019-05-07 | Pax Labs, Inc. | Lid for a vaporizer |
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| CN110678207B (zh) | 2017-04-21 | 2024-08-02 | 德马利克治疗公司 | 碘组合物 |
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| GB2564383B (en) | 2017-06-23 | 2021-04-21 | Gw Res Ltd | Use of cannabidiol in the treatment of tumours assoicated with Tuberous Sclerosis Complex |
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| ES2981120T3 (es) * | 2017-07-14 | 2024-10-07 | 5071 Inc | Composiciones de cannabinoides y métodos de preparación de las mismas |
| AU2018323861B2 (en) * | 2017-08-27 | 2023-08-17 | Rhodes Technologies | Pharmaceutical compositions for the treatment of ophthalmic conditions |
| USD887632S1 (en) | 2017-09-14 | 2020-06-16 | Pax Labs, Inc. | Vaporizer cartridge |
| EP3687496A1 (en) | 2017-09-27 | 2020-08-05 | Novaliq GmbH | Ophthalmic compositions comprising latanoprost for use in the treatment of ocular diseases |
| CN120022260A (zh) | 2017-10-04 | 2025-05-23 | 诺瓦利克有限责任公司 | 包含f6h8的眼用组合物 |
| US11498018B2 (en) * | 2017-11-27 | 2022-11-15 | Vasilios (Bill) Panagiotakopoulos | Extraction and purification of cannabinoid compounds |
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| GB201806953D0 (en) | 2018-04-27 | 2018-06-13 | Gw Res Ltd | Cannabidiol Preparations |
| CN112153970A (zh) | 2018-04-27 | 2020-12-29 | 诺瓦利克有限责任公司 | 用于治疗青光眼的包含他氟前列素的眼用组合物 |
| WO2020074697A1 (en) | 2018-10-12 | 2020-04-16 | Novaliq Gmbh | Ophthalmic composition for treatment of dry eye disease |
| CA3118895A1 (en) * | 2018-11-07 | 2020-05-14 | Columbia Care Llc | Suppository formulations having cannabinoid |
| 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 |
| WO2020186077A1 (en) * | 2019-03-12 | 2020-09-17 | 6th Wave Innovations Corp. | Molecularly imprinted polymers for extraction of cannabinoids and uses thereof |
| BR112021020302A2 (pt) * | 2019-04-09 | 2021-12-28 | Powderpost Llc | Composição, e método de tratamento de um sujeito com câncer |
| GB202002754D0 (en) | 2020-02-27 | 2020-04-15 | Gw Res Ltd | Methods of treating tuberous sclerosis complex with cannabidiol and everolimus |
| EP4172145A4 (en) | 2020-06-30 | 2024-08-21 | Reunion Neuroscience Canada Inc. | TRYPTAMIN PRODRUGS |
| CA3204196A1 (en) * | 2020-11-06 | 2022-05-12 | Zelira Therapeutics Operations Pty Ltd | Cannabinoid encapsulation technology |
| US11242328B1 (en) | 2021-02-25 | 2022-02-08 | Acid Neutral Alkaline Laboratory | Heterogeneous catalyst and method for preparation of aromatic tricyclic pyrans |
| US11242330B1 (en) | 2021-02-25 | 2022-02-08 | Acid Neutral Alkaline Laboratory | Organic 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 |
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| 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 (OSRAM) * | 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 |
| AU2005302162A1 (en) * | 2004-11-02 | 2006-05-11 | Shire Llc | Prodrugs of ribavirin with improved hepatic delivery |
| CA2659775A1 (en) * | 2006-08-04 | 2008-02-14 | Insys Therapeutics Inc. | Aqueous dronabinol formulations |
| WO2008134668A2 (en) * | 2007-04-27 | 2008-11-06 | Alexza Pharmaceuticals, Inc. | Heat-labile prodrugs |
| CN101835492B (zh) * | 2007-08-21 | 2012-11-21 | 德克萨斯州立大学董事会 | 用于制药应用的热动力学混合 |
| US20100303883A1 (en) * | 2007-10-17 | 2010-12-02 | Axxia Pharmaceuticals, Llc | Polymeric drug delivery systems and thermoplastic extrusion processes for producing such systems |
| SI2963031T1 (sl) * | 2007-11-30 | 2019-04-30 | Zynerba Pharmaceuticals, Inc. | Predzdravila tetrahidrokanabinola, sestavki, ki obsegajo predzdravila tetrahidrokanabinola in postopki njihove uporabe |
| 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 |
| ES2622582T3 (es) * | 2008-10-31 | 2017-07-06 | University Of Mississippi | Proceso para la preparación de ésteres de delta-9-THC-aminoácido |
-
2009
- 2009-11-02 ES ES09824226.6T patent/ES2622582T3/es active Active
- 2009-11-02 US US13/126,606 patent/US8809261B2/en active Active
- 2009-11-02 DK DK09824226.6T patent/DK2352497T3/en active
- 2009-11-02 CA CA2741862A patent/CA2741862C/en active Active
- 2009-11-02 HU HUE09824226A patent/HUE032158T2/en unknown
- 2009-11-02 WO PCT/US2009/062998 patent/WO2010051541A2/en not_active Ceased
- 2009-11-02 JP JP2011534860A patent/JP5739344B2/ja active Active
- 2009-11-02 PL PL09824226T patent/PL2352497T3/pl unknown
- 2009-11-02 EP EP09824226.6A patent/EP2352497B1/en active Active
- 2009-11-02 AU AU2009308665A patent/AU2009308665B2/en active Active
-
2014
- 2014-08-18 US US14/462,482 patent/US9630941B2/en active Active
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