ES2638057B1 - Tratamiento de la demencia con agonistas cannabinoides - Google Patents
Tratamiento de la demencia con agonistas cannabinoides Download PDFInfo
- Publication number
- ES2638057B1 ES2638057B1 ES201730284A ES201730284A ES2638057B1 ES 2638057 B1 ES2638057 B1 ES 2638057B1 ES 201730284 A ES201730284 A ES 201730284A ES 201730284 A ES201730284 A ES 201730284A ES 2638057 B1 ES2638057 B1 ES 2638057B1
- Authority
- ES
- Spain
- Prior art keywords
- jwh
- pentyl
- methyl
- methanone
- indole
- 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.)
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- 229930003827 cannabinoid Natural products 0.000 title abstract description 24
- 239000003557 cannabinoid Substances 0.000 title abstract description 24
- 239000000556 agonist Substances 0.000 title abstract description 23
- 206010012289 Dementia Diseases 0.000 title abstract description 10
- 230000002427 irreversible effect Effects 0.000 abstract description 3
- 230000003930 cognitive ability Effects 0.000 abstract 1
- -1 4-methyl-1-naphthyl Chemical group 0.000 description 36
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 14
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 238000007912 intraperitoneal administration Methods 0.000 description 8
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000969 carrier Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 4
- LACIUQLUNACUKC-UHFFFAOYSA-N JWH182 Chemical compound C12=CC=CC=C2N(CCCCC)C=C1C(=O)C1=CC=C(CC)C2=CC=CC=C12 LACIUQLUNACUKC-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
- 238000000185 intracerebroventricular administration Methods 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- CSXKNESDVLECTJ-VAMGGRTRSA-N (6ar,9r,10ar)-3-(1-hexylcyclobutyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromene-1,9-diol Chemical compound CC([C@@H]1CC[C@@H](O)C[C@H]1C1=C(O)C=2)(C)OC1=CC=2C1(CCCCCC)CCC1 CSXKNESDVLECTJ-VAMGGRTRSA-N 0.000 description 3
- FFRHKSZKZQWCOY-UOTIDGTBSA-N (6r,6ar,9r,10ar)-9-(hydroxymethyl)-6-(3-hydroxyprop-1-ynyl)-6-methyl-3-(2-methyloctan-2-yl)-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol Chemical compound C1[C@H](CO)CC[C@H]2[C@](C)(C#CCO)OC3=CC(C(C)(C)CCCCCC)=CC(O)=C3[C@@H]21 FFRHKSZKZQWCOY-UOTIDGTBSA-N 0.000 description 3
- SYKOWCSKDYZBIL-BKTWVJDESA-N (6s,6ar,9r,10ar)-9-(hydroxymethyl)-6-[(e)-3-hydroxyprop-1-enyl]-6-methyl-3-(2-methyloctan-2-yl)-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol Chemical compound C1[C@H](CO)CC[C@H]2[C@](C)(\C=C\CO)OC3=CC(C(C)(C)CCCCCC)=CC(O)=C3[C@@H]21 SYKOWCSKDYZBIL-BKTWVJDESA-N 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- ALQFAGFPQCBPED-UHFFFAOYSA-N AM2201 Chemical compound C12=CC=CC=C2N(CCCCCF)C=C1C(=O)C1=CC=CC2=CC=CC=C12 ALQFAGFPQCBPED-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OTGQIQQTPXJQRG-UHFFFAOYSA-N N-(octadecanoyl)ethanolamine Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCO OTGQIQQTPXJQRG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- LGEQQWMQCRIYKG-DOFZRALJSA-N anandamide Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO LGEQQWMQCRIYKG-DOFZRALJSA-N 0.000 description 3
- SCJNCDSAIRBRIA-DOFZRALJSA-N arachidonyl-2'-chloroethylamide Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCCl SCJNCDSAIRBRIA-DOFZRALJSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 229940079593 drug Drugs 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- CNTCHEBQQFICNR-UHFFFAOYSA-N jwh-098 Chemical compound C12=CC=CC=C2N(CCCCC)C(C)=C1C(=O)C1=CC=C(OC)C2=CC=CC=C12 CNTCHEBQQFICNR-UHFFFAOYSA-N 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- HXYVTAGFYLMHSO-UHFFFAOYSA-N palmitoyl ethanolamide Chemical compound CCCCCCCCCCCCCCCC(=O)NCCO HXYVTAGFYLMHSO-UHFFFAOYSA-N 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000008389 polyethoxylated castor oil Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RQWLYQGWFKBOIY-UHFFFAOYSA-N (1-butyl-2-methylindol-3-yl)-(7-methylnaphthalen-1-yl)methanone Chemical compound C12=CC=CC=C2N(CCCC)C(C)=C1C(=O)C1=CC=CC2=CC=C(C)C=C12 RQWLYQGWFKBOIY-UHFFFAOYSA-N 0.000 description 2
- QKXRHYJSCZFHEK-UHFFFAOYSA-N (1-butyl-2-methylindol-3-yl)-naphthalen-1-ylmethanone Chemical compound C12=CC=CC=C2N(CCCC)C(C)=C1C(=O)C1=CC=CC2=CC=CC=C12 QKXRHYJSCZFHEK-UHFFFAOYSA-N 0.000 description 2
- VIGWEDJLUIAROG-NSISKUIASA-N (1r,3r,4r)-4-(3-hydroxypropyl)-3-[4-(2-methylpentan-2-yl)phenyl]cyclohexan-1-ol Chemical compound C1=CC(C(C)(C)CCC)=CC=C1[C@H]1[C@H](CCCO)CC[C@@H](O)C1 VIGWEDJLUIAROG-NSISKUIASA-N 0.000 description 2
- RTGIZGGGWCYGAL-UHFFFAOYSA-N (2-methoxynaphthalen-1-yl)-(1-propylindol-3-yl)methanone Chemical compound C12=CC=CC=C2N(CCC)C=C1C(=O)C1=C(OC)C=CC2=CC=CC=C12 RTGIZGGGWCYGAL-UHFFFAOYSA-N 0.000 description 2
- POCUOUJJUBHVTI-UHFFFAOYSA-N (2-methoxynaphthalen-1-yl)-(2-methyl-1-pentylindol-3-yl)methanone Chemical compound C12=CC=CC=C2N(CCCCC)C(C)=C1C(=O)C1=C(OC)C=CC2=CC=CC=C12 POCUOUJJUBHVTI-UHFFFAOYSA-N 0.000 description 2
- MRZUOBIFOHQHRD-UHFFFAOYSA-N (2-methyl-1-pentylindol-3-yl)-(4-propylnaphthalen-1-yl)methanone Chemical compound C12=CC=CC=C2N(CCCCC)C(C)=C1C(=O)C1=CC=C(CCC)C2=CC=CC=C12 MRZUOBIFOHQHRD-UHFFFAOYSA-N 0.000 description 2
- XHIXPRIGTFMZHJ-UHFFFAOYSA-N (4-butylnaphthalen-1-yl)-(1-propylindol-3-yl)methanone Chemical compound C12=CC=CC=C2C(CCCC)=CC=C1C(=O)C1=CN(CCC)C2=CC=CC=C12 XHIXPRIGTFMZHJ-UHFFFAOYSA-N 0.000 description 2
- MZJYEWXYEBBSAL-UHFFFAOYSA-N (4-butylnaphthalen-1-yl)-(2-methyl-1-pentylindol-3-yl)methanone Chemical compound C12=CC=CC=C2N(CCCCC)C(C)=C1C(=O)C1=CC=C(CCCC)C2=CC=CC=C12 MZJYEWXYEBBSAL-UHFFFAOYSA-N 0.000 description 2
- NKIYNRUHLLPQDP-UHFFFAOYSA-N (4-butylnaphthalen-1-yl)-(2-methyl-1-propylindol-3-yl)methanone Chemical compound C12=CC=CC=C2C(CCCC)=CC=C1C(=O)C1=C(C)N(CCC)C2=CC=CC=C12 NKIYNRUHLLPQDP-UHFFFAOYSA-N 0.000 description 2
- KGXJBLWHKBDEOZ-UHFFFAOYSA-N (4-chloronaphthalen-1-yl)-(1-propylindol-3-yl)methanone Chemical compound C12=CC=CC=C2N(CCC)C=C1C(=O)C1=CC=C(Cl)C2=CC=CC=C12 KGXJBLWHKBDEOZ-UHFFFAOYSA-N 0.000 description 2
- UOKFJJUVHMPGSE-UHFFFAOYSA-N (4-chloronaphthalen-1-yl)-(2-methyl-1-pentylindol-3-yl)methanone Chemical compound C12=CC=CC=C2N(CCCCC)C(C)=C1C(=O)C1=CC=C(Cl)C2=CC=CC=C12 UOKFJJUVHMPGSE-UHFFFAOYSA-N 0.000 description 2
- NCEVWPRTUYLBGV-UHFFFAOYSA-N (4-ethoxynaphthalen-1-yl)-(1-propylindol-3-yl)methanone Chemical compound C12=CC=CC=C2N(CCC)C=C1C(=O)C1=CC=C(OCC)C2=CC=CC=C12 NCEVWPRTUYLBGV-UHFFFAOYSA-N 0.000 description 2
- SNCKIADQCHVLDK-UHFFFAOYSA-N (4-ethoxynaphthalen-1-yl)-(2-methyl-1-pentylindol-3-yl)methanone Chemical compound C12=CC=CC=C2N(CCCCC)C(C)=C1C(=O)C1=CC=C(OCC)C2=CC=CC=C12 SNCKIADQCHVLDK-UHFFFAOYSA-N 0.000 description 2
- UOQYTDWXUDZRMX-UHFFFAOYSA-N (4-ethoxynaphthalen-1-yl)-(2-methyl-1-propylindol-3-yl)methanone Chemical compound C12=CC=CC=C2N(CCC)C(C)=C1C(=O)C1=CC=C(OCC)C2=CC=CC=C12 UOQYTDWXUDZRMX-UHFFFAOYSA-N 0.000 description 2
- NDMJIRUJOQIHLL-UHFFFAOYSA-N (4-ethylnaphthalen-1-yl)-(1-propylindol-3-yl)methanone Chemical compound C12=CC=CC=C2N(CCC)C=C1C(=O)C1=CC=C(CC)C2=CC=CC=C12 NDMJIRUJOQIHLL-UHFFFAOYSA-N 0.000 description 2
- JAVDQKMSPNBPCK-UHFFFAOYSA-N (4-ethylnaphthalen-1-yl)-(2-methyl-1-pentylindol-3-yl)methanone Chemical compound C12=CC=CC=C2N(CCCCC)C(C)=C1C(=O)C1=CC=C(CC)C2=CC=CC=C12 JAVDQKMSPNBPCK-UHFFFAOYSA-N 0.000 description 2
- DGMWDWZKLFRCMQ-UHFFFAOYSA-N (4-ethylnaphthalen-1-yl)-(2-methyl-1-propylindol-3-yl)methanone Chemical compound C12=CC=CC=C2N(CCC)C(C)=C1C(=O)C1=CC=C(CC)C2=CC=CC=C12 DGMWDWZKLFRCMQ-UHFFFAOYSA-N 0.000 description 2
- IBCGCPIEVOHYAS-UHFFFAOYSA-N (4-fluoronaphthalen-1-yl)-(2-methyl-1-pentylindol-3-yl)methanone Chemical compound C12=CC=CC=C2N(CCCCC)C(C)=C1C(=O)C1=CC=C(F)C2=CC=CC=C12 IBCGCPIEVOHYAS-UHFFFAOYSA-N 0.000 description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
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- NHQVWPJMCINXPI-UHFFFAOYSA-N 1-(2-methyl-1-pentylindol-3-yl)-2-(2-methylphenyl)ethanone Chemical compound C12=CC=CC=C2N(CCCCC)C(C)=C1C(=O)CC1=CC=CC=C1C NHQVWPJMCINXPI-UHFFFAOYSA-N 0.000 description 2
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- LFFIIZFINPPEMC-UHFFFAOYSA-N 1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole Chemical compound C12=CC=CC=C2N(CCCCCF)C=C1C(=O)C1=CC=CC=C1I LFFIIZFINPPEMC-UHFFFAOYSA-N 0.000 description 2
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 2
- RNQWQIZOTKYEKJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1-(2-methyl-1-pentylindol-3-yl)ethanone Chemical compound C12=CC=CC=C2N(CCCCC)C(C)=C1C(=O)CC1=CC=C(OC)C=C1 RNQWQIZOTKYEKJ-UHFFFAOYSA-N 0.000 description 2
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- 239000002202 Polyethylene glycol Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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Classifications
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
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- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES201730284A ES2638057B1 (es) | 2017-03-02 | 2017-03-02 | Tratamiento de la demencia con agonistas cannabinoides |
| JP2019547448A JP2020509043A (ja) | 2017-03-02 | 2018-02-23 | カンナビノイドアゴニストによる認知症の治療 |
| PCT/EP2018/054525 WO2018158150A1 (en) | 2017-03-02 | 2018-02-23 | Treatment of dementia with cannabinoid agonists |
| EP18707035.4A EP3589322A1 (en) | 2017-03-02 | 2018-02-23 | Treatment of dementia with cannabinoid agonists |
| US16/489,110 US20200016163A1 (en) | 2017-03-02 | 2018-02-23 | Treatment of dementia with cannabinoid agonists |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES201730284A ES2638057B1 (es) | 2017-03-02 | 2017-03-02 | Tratamiento de la demencia con agonistas cannabinoides |
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|---|---|
| ES2638057A1 ES2638057A1 (es) | 2017-10-18 |
| ES2638057B1 true ES2638057B1 (es) | 2018-10-01 |
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| ES201730284A Active ES2638057B1 (es) | 2017-03-02 | 2017-03-02 | Tratamiento de la demencia con agonistas cannabinoides |
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| EP (1) | EP3589322A1 (enExample) |
| JP (1) | JP2020509043A (enExample) |
| ES (1) | ES2638057B1 (enExample) |
| WO (1) | WO2018158150A1 (enExample) |
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| EP3893673A4 (en) | 2018-12-14 | 2023-05-03 | Natural Extraction Systems, LLC | COMPOSITIONS AND METHODS RELATED TO ANIONIC CANNABINOID MOLECULES |
| WO2021084523A2 (en) * | 2019-10-31 | 2021-05-06 | Radient Technologies Innovations Inc. | Enhancing lifestyle of memory impaired patients using cbd |
| WO2021097163A1 (en) * | 2019-11-14 | 2021-05-20 | Natural Extraction Systems, LLC | Pharmaceutical compositions comprising cannabinoid anions |
| US12349706B2 (en) | 2020-07-31 | 2025-07-08 | Natural Extraction Systems, LLC | Compositions and methods related to excipients and cannabinoid formulations |
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| WO2009059277A1 (en) * | 2007-11-02 | 2009-05-07 | University Of South Florida | Synergistic modulation of microglial activation by nicotine and thc |
| PL2606032T3 (pl) * | 2010-08-20 | 2015-07-31 | Univ Washington Through Its Center For Commercialization | Kompozycja i sposoby terapii glejakaep |
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- 2018-02-23 US US16/489,110 patent/US20200016163A1/en not_active Abandoned
- 2018-02-23 EP EP18707035.4A patent/EP3589322A1/en not_active Ceased
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Also Published As
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| JP2020509043A (ja) | 2020-03-26 |
| EP3589322A1 (en) | 2020-01-08 |
| US20200016163A1 (en) | 2020-01-16 |
| WO2018158150A1 (en) | 2018-09-07 |
| ES2638057A1 (es) | 2017-10-18 |
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