RU2019131436A - Стабилизированные композиции связанных с белком каннабиоидов - Google Patents
Стабилизированные композиции связанных с белком каннабиоидов Download PDFInfo
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- RU2019131436A RU2019131436A RU2019131436A RU2019131436A RU2019131436A RU 2019131436 A RU2019131436 A RU 2019131436A RU 2019131436 A RU2019131436 A RU 2019131436A RU 2019131436 A RU2019131436 A RU 2019131436A RU 2019131436 A RU2019131436 A RU 2019131436A
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- plasma protein
- composition
- cannabinoid
- fatty acid
- aqueous
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- 239000000203 mixture Substances 0.000 title claims 22
- 229930003827 cannabinoid Natural products 0.000 title claims 14
- 239000003557 cannabinoid Substances 0.000 title claims 14
- 229940065144 cannabinoids Drugs 0.000 title claims 4
- 102000004169 proteins and genes Human genes 0.000 title claims 2
- 108090000623 proteins and genes Proteins 0.000 title claims 2
- 238000009472 formulation Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 26
- 108010017384 Blood Proteins Proteins 0.000 claims 17
- 102000004506 Blood Proteins Human genes 0.000 claims 17
- 235000014113 dietary fatty acids Nutrition 0.000 claims 12
- 229930195729 fatty acid Natural products 0.000 claims 12
- 239000000194 fatty acid Substances 0.000 claims 12
- 150000004665 fatty acids Chemical class 0.000 claims 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- 239000002609 medium Substances 0.000 claims 6
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 claims 4
- 238000011534 incubation Methods 0.000 claims 4
- ZROLHBHDLIHEMS-HUUCEWRRSA-N (6ar,10ar)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCC)=CC(O)=C3[C@@H]21 ZROLHBHDLIHEMS-HUUCEWRRSA-N 0.000 claims 2
- KTPDAZGMXXWSMU-UHFFFAOYSA-N Cannabichromen Natural products CCCCc1cc(O)c2C=CC(C)(CCC=C(C)C)Oc2c1 KTPDAZGMXXWSMU-UHFFFAOYSA-N 0.000 claims 2
- UVOLYTDXHDXWJU-NRFANRHFSA-N Cannabichromene Natural products C1=C[C@](C)(CCC=C(C)C)OC2=CC(CCCCC)=CC(O)=C21 UVOLYTDXHDXWJU-NRFANRHFSA-N 0.000 claims 2
- WVOLTBSCXRRQFR-SJORKVTESA-N Cannabidiolic acid Natural products OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@@H]1[C@@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-SJORKVTESA-N 0.000 claims 2
- VBGLYOIFKLUMQG-UHFFFAOYSA-N Cannabinol Chemical compound C1=C(C)C=C2C3=C(O)C=C(CCCCC)C=C3OC(C)(C)C2=C1 VBGLYOIFKLUMQG-UHFFFAOYSA-N 0.000 claims 2
- ZROLHBHDLIHEMS-UHFFFAOYSA-N Delta9 tetrahydrocannabivarin Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCC)=CC(O)=C3C21 ZROLHBHDLIHEMS-UHFFFAOYSA-N 0.000 claims 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims 2
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 claims 2
- QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 2
- 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 2
- 229950011318 cannabidiol Drugs 0.000 claims 2
- WVOLTBSCXRRQFR-DLBZAZTESA-N cannabidiolic acid Chemical compound OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-DLBZAZTESA-N 0.000 claims 2
- QXACEHWTBCFNSA-SFQUDFHCSA-N cannabigerol Chemical compound CCCCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1 QXACEHWTBCFNSA-SFQUDFHCSA-N 0.000 claims 2
- QXACEHWTBCFNSA-UHFFFAOYSA-N cannabigerol Natural products CCCCCC1=CC(O)=C(CC=C(C)CCC=C(C)C)C(O)=C1 QXACEHWTBCFNSA-UHFFFAOYSA-N 0.000 claims 2
- SEEZIOZEUUMJME-FOWTUZBSSA-N cannabigerolic acid Chemical compound CCCCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1C(O)=O SEEZIOZEUUMJME-FOWTUZBSSA-N 0.000 claims 2
- SEEZIOZEUUMJME-UHFFFAOYSA-N cannabinerolic acid Natural products CCCCCC1=CC(O)=C(CC=C(C)CCC=C(C)C)C(O)=C1C(O)=O SEEZIOZEUUMJME-UHFFFAOYSA-N 0.000 claims 2
- 229960003453 cannabinol Drugs 0.000 claims 2
- 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 claims 2
- 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 claims 2
- 229960004242 dronabinol Drugs 0.000 claims 2
- 125000005313 fatty acid group Chemical group 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 235000020778 linoleic acid Nutrition 0.000 claims 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims 2
- 102000009027 Albumins Human genes 0.000 claims 1
- 108010088751 Albumins Proteins 0.000 claims 1
- 108010068307 Alpha-Globulins Proteins 0.000 claims 1
- 108010087504 Beta-Globulins Proteins 0.000 claims 1
- SEEZIOZEUUMJME-VBKFSLOCSA-N Cannabigerolic acid Natural products CCCCCC1=CC(O)=C(C\C=C(\C)CCC=C(C)C)C(O)=C1C(O)=O SEEZIOZEUUMJME-VBKFSLOCSA-N 0.000 claims 1
- UCONUSSAWGCZMV-HZPDHXFCSA-N Delta(9)-tetrahydrocannabinolic acid Chemical compound C([C@H]1C(C)(C)O2)CC(C)=C[C@H]1C1=C2C=C(CCCCC)C(C(O)=O)=C1O UCONUSSAWGCZMV-HZPDHXFCSA-N 0.000 claims 1
- 102000003886 Glycoproteins Human genes 0.000 claims 1
- 108090000288 Glycoproteins Proteins 0.000 claims 1
- YSBFLLZNALVODA-RBUKOAKNSA-N JWH-133 Chemical compound C1C(C)=CC[C@H]2C(C)(C)OC3=CC(C(C)(C)CCC)=CC=C3[C@@H]21 YSBFLLZNALVODA-RBUKOAKNSA-N 0.000 claims 1
- 102000004895 Lipoproteins Human genes 0.000 claims 1
- 108090001030 Lipoproteins Proteins 0.000 claims 1
- 101100268917 Oryctolagus cuniculus ACOX2 gene Proteins 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
- UCONUSSAWGCZMV-UHFFFAOYSA-N Tetrahydro-cannabinol-carbonsaeure Natural products O1C(C)(C)C2CCC(C)=CC2C2=C1C=C(CCCCC)C(C(O)=O)=C2O UCONUSSAWGCZMV-UHFFFAOYSA-N 0.000 claims 1
- HQVHOQAKMCMIIM-HXUWFJFHSA-N WIN 55212-2 Chemical compound C([C@@H]1COC=2C=CC=C3C(C(=O)C=4C5=CC=CC=C5C=CC=4)=C(N1C3=2)C)N1CCOCC1 HQVHOQAKMCMIIM-HXUWFJFHSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- SSQJFGMEZBFMNV-PMACEKPBSA-N dexanabinol Chemical compound C1C(CO)=CC[C@@H]2C(C)(C)OC3=CC(C(C)(C)CCCCCC)=CC(O)=C3[C@H]21 SSQJFGMEZBFMNV-PMACEKPBSA-N 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 108010074605 gamma-Globulins Proteins 0.000 claims 1
- 230000002209 hydrophobic effect Effects 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/201—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having one or two double bonds, e.g. oleic, linoleic acids
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- A61K36/185—Magnoliopsida (dicotyledons)
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein
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- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
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- A61K47/542—Carboxylic acids, e.g. a fatty acid or an amino acid
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- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
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Claims (30)
1. Способ получения композиции жирной кислоты, каннабиоида и белка плазмы (FCP), включающий:
приведение белка плазмы или его пептидной части в контакт с дополнительной композицией жирной кислоты, содержащей по меньшей мере одну жирную кислоту; и
приведение белка плазмы или его части в контакт с композицией каннабиоида, содержащей по меньшей мере один каннабиоид,
таким образом, что получают комбинированную композицию, которая содержит комплекс FCP, в котором по меньшей мере одна жирная кислота и по меньшей мере один каннабиоид связаны с белком плазмы или его частью.
2. Способ по п. 1, где по меньшей мере одна жирная кислота включает линолевую кислоту.
3. Способ по п. 1, где по меньшей мере одна жирная кислота состоит из линолевой кислоты.
4. Способ по любому из пп. 1-3, где композиция каннабиоида по существу не содержит жирных кислот.
5. Способ по п. 1, дополнительно включающий: очистку комбинированной композиции с удерживанием белка плазмы или его части и с удалением жирной кислоты или каннабиоидов, не связанных с белком плазмы или его частью, таким образом, что по меньшей мере 80% жирных кислот и по меньшей мере 80% каннабиоидов в комбинированной композиции связаны с белком плазмы или его частью.
6. Способ по п. 5, где по существу все жирные кислоты и по существу все каннабиоиды в комбинированной композиции связаны с белком плазмы или его частью.
7. Способ по п. 5, где связывание жирной кислоты и/или каннабиоида с белком плазмы или его частью представляет собой нековалентное связывание.
8. Способ по п. 7, где нековалентное связывание представляет собой взаимодействие белок-лиганд.
9. Способ по п. 7, где нековалентное связывание характеризуется неспецифичными липофильными и полярными взаимодействиями с гидрофобными белковыми карманами в белке плазмы или его части.
10. Способ по п. 1, где приведение белка плазмы или его части в контакт с дополнительной композицией жирной кислоты включает смешивание композиции, содержащей белок плазмы или его часть, с дополнительной композицией кислоты и инкубирование данной смеси.
11. Способ по п. 10, где инкубация происходит при температуре от 25 до 40 градусов Цельсия (°C).
12. Способ по п. 10, где инкубация происходит в водно-спиртовой среде.
13. Способ по п. 12, где спирт, содержащийся в водно-спиртовой среде, представляет собой этанол.
14. Способ по п. 12, где исходная концентрация спирта водно-спиртовой среды составляет от 2 до 10%.
15. Способ по п. 1, где приведение белка плазмы или его части в контакт с композицией каннабиоида включает смешивание композиции, содержащей белок плазмы или его часть, с композицией каннабиоида и инкубирование смеси.
16. Способ по п. 15, где инкубация происходит при температуре от 25 до 40°C.
17. Способ по п. 15, где инкубация происходит в водно-спиртовой среде.
18. Способ по п. 17, где спирт, содержащийся в водно-спиртовой среде, представляет собой этанол.
19. Способ по п. 17, где исходная концентрация спирта водно-спиртовой среды составляет от 16 до 30%.
20. Способ по п. 1, где комбинированная композиция получена в водной среде.
21. Способ по п. 20, где водная среда состоит из воды или физиологического раствора.
22. Способ по п. 20, дополнительно включающий сушку или лиофилизацию комбинированной композиции.
23. Способ по п. 1, где по меньшей мере один каннабиоид представляет собой один или комбинацию двух или более из группы, состоящей из: THCA (тетрагидроканнабиноловая кислота), THC (тетрагидроканнабинол), CBDA (каннабидиоловая кислота), CBD (каннабидиол), CBN (каннабинол), CBG (каннабигерол), THCV (тетрагидроканнабиварин), CBGA (каннабигероловая кислота), CBC (каннабихромен), HU-210, WIN 55,212-2 и JWH-133.
24. Способ по п. 1, где белок плазмы или его часть выбраны из группы, состоящей из альбумина, липопротеина, гликопротеина и α, β и γ глобулинов и смесей одного или более чем одного из них.
25. Способ по п. 1, где белок плазмы или его часть являются рекомбинантными.
26. Композиция FCP, полученная по п. 1.
27. Способ улучшения стабильности для каннабиоида, связанного с белком плазмы, включающий получение композиции FCP по п. 1.
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CA3119729A1 (en) | 2018-10-10 | 2020-04-16 | Treehouse Biotech, Inc. | Synthesis of cannabigerol |
WO2020214220A2 (en) * | 2019-01-15 | 2020-10-22 | Gustin John C | Cannabinoid systems and methods: water-solubility, targeting, and augmentation |
EP3923915A4 (en) * | 2019-02-11 | 2023-03-22 | John Robert Chancey | METHODS OF MAKING AND USING PHYTOCANNABINOIDS COMPLEXED WITH A PROTEIN, PEPTIDE, AMINO ACCHARIDE, POLYSACCHARIDE, DISACCHARIDE, ORMONOSACCHARIDE |
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US11666544B1 (en) | 2022-07-05 | 2023-06-06 | Poviva Corp. | Compositions and methods for treating hypertension |
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