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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| HUE032158T2 (en) * | 2008-10-31 | 2017-09-28 | Univ Mississippi | Process for the preparation of delta9-THC amino acid esters |
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| KR102829078B1 (ko) | 2020-06-30 | 2025-07-04 | 리유니온 뉴로사이언스 인코포레이티드 | 트립타민 전구약물 |
| KR20230128451A (ko) * | 2020-11-06 | 2023-09-05 | 젤리라 테라퓨틱스 오퍼레이션즈 피티와이 엘티디 | 카나비노이드 캡슐화 기술 |
| 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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| 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 |
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| 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 |
| BRPI0516922A (pt) * | 2004-11-02 | 2008-09-23 | New River Pharmaceuticals Inc | composto de ribavirina, método para fazer um composto de ribavirina, método para usar um composto de ribavirina e composição farmacêutica |
| 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 |
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| 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 |
| HUE032158T2 (en) * | 2008-10-31 | 2017-09-28 | Univ Mississippi | Process for the preparation of delta9-THC amino acid esters |
-
2009
- 2009-11-02 HU HUE09824226A patent/HUE032158T2/en unknown
- 2009-11-02 JP JP2011534860A patent/JP5739344B2/ja 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 ES ES09824226.6T patent/ES2622582T3/es 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 CA CA2741862A patent/CA2741862C/en active Active
- 2009-11-02 WO PCT/US2009/062998 patent/WO2010051541A2/en not_active Ceased
- 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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