WO2022173812A1 - Compositions et procédés associés à des anions cannabinoïdes - Google Patents
Compositions et procédés associés à des anions cannabinoïdes Download PDFInfo
- Publication number
- WO2022173812A1 WO2022173812A1 PCT/US2022/015795 US2022015795W WO2022173812A1 WO 2022173812 A1 WO2022173812 A1 WO 2022173812A1 US 2022015795 W US2022015795 W US 2022015795W WO 2022173812 A1 WO2022173812 A1 WO 2022173812A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- health condition
- composition
- cannabinoid
- cancer
- anion
- Prior art date
Links
- 229930003827 cannabinoid Natural products 0.000 title claims abstract description 160
- 239000003557 cannabinoid Substances 0.000 title claims abstract description 160
- 239000000203 mixture Substances 0.000 title claims abstract description 124
- 150000001450 anions Chemical class 0.000 title claims abstract description 87
- 238000000034 method Methods 0.000 title claims description 78
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims abstract description 24
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims abstract description 24
- 230000001404 mediated effect Effects 0.000 claims abstract description 24
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims abstract description 18
- 230000019491 signal transduction Effects 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000010494 dissociation reaction Methods 0.000 claims abstract description 7
- 230000005593 dissociations Effects 0.000 claims abstract description 7
- 230000036541 health Effects 0.000 claims description 193
- -1 hydroxy, cyano, phenyl Chemical group 0.000 claims description 177
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 63
- 239000007791 liquid phase Substances 0.000 claims description 32
- 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 description 27
- YJYIDZLGVYOPGU-XNTDXEJSSA-N 2-[(2e)-3,7-dimethylocta-2,6-dienyl]-5-propylbenzene-1,3-diol Chemical compound CCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1 YJYIDZLGVYOPGU-XNTDXEJSSA-N 0.000 claims description 26
- 208000002193 Pain Diseases 0.000 claims description 25
- 206010010904 Convulsion Diseases 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 230000000306 recurrent effect Effects 0.000 claims description 22
- 201000004681 Psoriasis Diseases 0.000 claims description 20
- 206010003246 arthritis Diseases 0.000 claims description 19
- QHMBSVQNZZTUGM-UHFFFAOYSA-N 2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-5-pentylbenzene-1,3-diol Chemical compound OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 229940098465 tincture Drugs 0.000 claims description 18
- 150000001720 carbohydrates Chemical class 0.000 claims description 17
- 235000014633 carbohydrates Nutrition 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 208000001132 Osteoporosis Diseases 0.000 claims description 14
- 208000028017 Psychotic disease Diseases 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 208000011231 Crohn disease Diseases 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 210000002784 stomach Anatomy 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 239000007790 solid phase Substances 0.000 claims description 11
- 208000008035 Back Pain Diseases 0.000 claims description 10
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 10
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims description 10
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 10
- 206010046851 Uveitis Diseases 0.000 claims description 10
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 10
- 201000000306 sarcoidosis Diseases 0.000 claims description 10
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 9
- 208000019901 Anxiety disease Diseases 0.000 claims description 9
- 206010015037 epilepsy Diseases 0.000 claims description 9
- 230000002757 inflammatory effect Effects 0.000 claims description 9
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims description 8
- 206010044565 Tremor Diseases 0.000 claims description 8
- 230000001594 aberrant effect Effects 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 8
- 230000001684 chronic effect Effects 0.000 claims description 8
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 8
- 239000002674 ointment Substances 0.000 claims description 8
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 7
- 208000001708 Dupuytren contracture Diseases 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 208000015181 infectious disease Diseases 0.000 claims description 7
- 206010025135 lupus erythematosus Diseases 0.000 claims description 7
- 230000011664 signaling Effects 0.000 claims description 7
- 208000020925 Bipolar disease Diseases 0.000 claims description 6
- 206010065687 Bone loss Diseases 0.000 claims description 6
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 6
- 206010006895 Cachexia Diseases 0.000 claims description 6
- 206010058019 Cancer Pain Diseases 0.000 claims description 6
- 208000008238 Muscle Spasticity Diseases 0.000 claims description 6
- 206010028813 Nausea Diseases 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 6
- 208000028311 absence seizure Diseases 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 208000029560 autism spectrum disease Diseases 0.000 claims description 6
- 230000001363 autoimmune Effects 0.000 claims description 6
- 230000008693 nausea Effects 0.000 claims description 6
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 6
- 208000018198 spasticity Diseases 0.000 claims description 6
- 230000000699 topical effect Effects 0.000 claims description 6
- 208000025705 Axial Spondyloarthritis Diseases 0.000 claims description 5
- 208000000094 Chronic Pain Diseases 0.000 claims description 5
- 208000003456 Juvenile Arthritis Diseases 0.000 claims description 5
- 206010034464 Periarthritis Diseases 0.000 claims description 5
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 5
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 5
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 5
- 201000002661 Spondylitis Diseases 0.000 claims description 5
- 210000000988 bone and bone Anatomy 0.000 claims description 5
- 208000002557 hidradenitis Diseases 0.000 claims description 5
- 201000007162 hidradenitis suppurativa Diseases 0.000 claims description 5
- 230000002458 infectious effect Effects 0.000 claims description 5
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims description 5
- 201000008482 osteoarthritis Diseases 0.000 claims description 5
- 208000019764 polyarticular juvenile idiopathic arthritis Diseases 0.000 claims description 5
- 201000003651 pulmonary sarcoidosis Diseases 0.000 claims description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- GOZMBJCYMQQACI-UHFFFAOYSA-N 6,7-dimethyl-3-[[methyl-[2-[methyl-[[1-[3-(trifluoromethyl)phenyl]indol-3-yl]methyl]amino]ethyl]amino]methyl]chromen-4-one;dihydrochloride Chemical compound Cl.Cl.C=1OC2=CC(C)=C(C)C=C2C(=O)C=1CN(C)CCN(C)CC(C1=CC=CC=C11)=CN1C1=CC=CC(C(F)(F)F)=C1 GOZMBJCYMQQACI-UHFFFAOYSA-N 0.000 claims description 4
- 208000030507 AIDS Diseases 0.000 claims description 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 4
- 241000218236 Cannabis Species 0.000 claims description 4
- 208000001387 Causalgia Diseases 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 206010012335 Dependence Diseases 0.000 claims description 4
- 208000001654 Drug Resistant Epilepsy Diseases 0.000 claims description 4
- 208000011893 Febrile infection-related epilepsy syndrome Diseases 0.000 claims description 4
- 208000008930 Low Back Pain Diseases 0.000 claims description 4
- 244000062730 Melissa officinalis Species 0.000 claims description 4
- 235000010654 Melissa officinalis Nutrition 0.000 claims description 4
- 208000019695 Migraine disease Diseases 0.000 claims description 4
- 208000007101 Muscle Cramp Diseases 0.000 claims description 4
- 208000036572 Myoclonic epilepsy Diseases 0.000 claims description 4
- 208000037004 Myoclonic-astatic epilepsy Diseases 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 206010033864 Paranoia Diseases 0.000 claims description 4
- 208000027099 Paranoid disease Diseases 0.000 claims description 4
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 4
- 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 claims description 4
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 4
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 4
- 208000005392 Spasm Diseases 0.000 claims description 4
- 206010048010 Withdrawal syndrome Diseases 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 208000022531 anorexia Diseases 0.000 claims description 4
- 235000013361 beverage Nutrition 0.000 claims description 4
- 208000028683 bipolar I disease Diseases 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
- 239000006071 cream Substances 0.000 claims description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 4
- HEBKCHPVOIAQTA-UHFFFAOYSA-N d-arabitol Chemical compound OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 4
- 206010061428 decreased appetite Diseases 0.000 claims description 4
- 239000007933 dermal patch Substances 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 210000003238 esophagus Anatomy 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 4
- 208000005017 glioblastoma Diseases 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- CDAISMWEOUEBRE-UHFFFAOYSA-N inositol Chemical compound OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 4
- 206010022437 insomnia Diseases 0.000 claims description 4
- 239000000865 liniment Substances 0.000 claims description 4
- 239000006210 lotion Substances 0.000 claims description 4
- 208000024714 major depressive disease Diseases 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- 208000004296 neuralgia Diseases 0.000 claims description 4
- 201000001119 neuropathy Diseases 0.000 claims description 4
- 230000007823 neuropathy Effects 0.000 claims description 4
- 229960002715 nicotine Drugs 0.000 claims description 4
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 4
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 208000020016 psychiatric disease Diseases 0.000 claims description 4
- 208000023504 respiratory system disease Diseases 0.000 claims description 4
- 208000007056 sickle cell anemia Diseases 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 3
- 206010057239 Post laminectomy syndrome Diseases 0.000 claims description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 238000001356 surgical procedure Methods 0.000 claims description 3
- 238000011200 topical administration Methods 0.000 claims description 3
- 239000000811 xylitol Substances 0.000 claims description 3
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 3
- 229960002675 xylitol Drugs 0.000 claims description 3
- 235000010447 xylitol Nutrition 0.000 claims description 3
- 125000006433 1-ethyl cyclopropyl group Chemical group [H]C([H])([H])C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 2
- REOZWEGFPHTFEI-UHFFFAOYSA-N 2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-5-propylbenzene-1,3-diol Chemical compound OC1=CC(CCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 REOZWEGFPHTFEI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 206010000087 Abdominal pain upper Diseases 0.000 claims description 2
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- 208000008811 Agoraphobia Diseases 0.000 claims description 2
- 206010053164 Alcohol withdrawal syndrome Diseases 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 206010061424 Anal cancer Diseases 0.000 claims description 2
- 208000009575 Angelman syndrome Diseases 0.000 claims description 2
- 208000007860 Anus Neoplasms Diseases 0.000 claims description 2
- 206010003101 Arnold-Chiari Malformation Diseases 0.000 claims description 2
- 208000036640 Asperger disease Diseases 0.000 claims description 2
- 201000006062 Asperger syndrome Diseases 0.000 claims description 2
- 206010003571 Astrocytoma Diseases 0.000 claims description 2
- 206010003591 Ataxia Diseases 0.000 claims description 2
- 102000014461 Ataxins Human genes 0.000 claims description 2
- 108010078286 Ataxins Proteins 0.000 claims description 2
- 206010003628 Atonic seizures Diseases 0.000 claims description 2
- 206010003805 Autism Diseases 0.000 claims description 2
- 208000020706 Autistic disease Diseases 0.000 claims description 2
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 2
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 208000010392 Bone Fractures Diseases 0.000 claims description 2
- 208000020084 Bone disease Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 208000021465 Brief psychotic disease Diseases 0.000 claims description 2
- 208000032841 Bulimia Diseases 0.000 claims description 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 2
- 201000009030 Carcinoma Diseases 0.000 claims description 2
- 206010008025 Cerebellar ataxia Diseases 0.000 claims description 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
- 208000015321 Chiari malformation Diseases 0.000 claims description 2
- 208000004051 Chronic Traumatic Encephalopathy Diseases 0.000 claims description 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 claims description 2
- 206010010774 Constipation Diseases 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
- 208000024254 Delusional disease Diseases 0.000 claims description 2
- 201000010374 Down Syndrome Diseases 0.000 claims description 2
- 201000007547 Dravet syndrome Diseases 0.000 claims description 2
- 206010013801 Duchenne Muscular Dystrophy Diseases 0.000 claims description 2
- 208000014094 Dystonic disease Diseases 0.000 claims description 2
- 206010073210 Dystonic tremor Diseases 0.000 claims description 2
- 208000002197 Ehlers-Danlos syndrome Diseases 0.000 claims description 2
- 206010014733 Endometrial cancer Diseases 0.000 claims description 2
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 2
- 206010014989 Epidermolysis bullosa Diseases 0.000 claims description 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 2
- 208000001640 Fibromyalgia Diseases 0.000 claims description 2
- 206010016654 Fibrosis Diseases 0.000 claims description 2
- 208000001914 Fragile X syndrome Diseases 0.000 claims description 2
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims description 2
- 208000001613 Gambling Diseases 0.000 claims description 2
- 208000011688 Generalised anxiety disease Diseases 0.000 claims description 2
- 208000021309 Germ cell tumor Diseases 0.000 claims description 2
- 208000010412 Glaucoma Diseases 0.000 claims description 2
- 201000010915 Glioblastoma multiforme Diseases 0.000 claims description 2
- 201000005569 Gout Diseases 0.000 claims description 2
- 208000034308 Grand mal convulsion Diseases 0.000 claims description 2
- 206010019233 Headaches Diseases 0.000 claims description 2
- 208000016988 Hemorrhagic Stroke Diseases 0.000 claims description 2
- 208000005176 Hepatitis C Diseases 0.000 claims description 2
- 208000017604 Hodgkin disease Diseases 0.000 claims description 2
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims description 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 206010020523 Hydromyelia Diseases 0.000 claims description 2
- 208000004454 Hyperalgesia Diseases 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 206010058359 Hypogonadism Diseases 0.000 claims description 2
- 206010021042 Hypopharyngeal cancer Diseases 0.000 claims description 2
- 206010056305 Hypopharyngeal neoplasm Diseases 0.000 claims description 2
- 206010070511 Hypoxic-ischaemic encephalopathy Diseases 0.000 claims description 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 2
- 208000005615 Interstitial Cystitis Diseases 0.000 claims description 2
- 208000004404 Intractable Pain Diseases 0.000 claims description 2
- 208000032382 Ischaemic stroke Diseases 0.000 claims description 2
- 206010071082 Juvenile myoclonic epilepsy Diseases 0.000 claims description 2
- 208000007766 Kaposi sarcoma Diseases 0.000 claims description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
- 206010023825 Laryngeal cancer Diseases 0.000 claims description 2
- 201000006792 Lennox-Gastaut syndrome Diseases 0.000 claims description 2
- 206010061523 Lip and/or oral cavity cancer Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 208000032271 Malignant tumor of penis Diseases 0.000 claims description 2
- 206010026749 Mania Diseases 0.000 claims description 2
- 206010027406 Mesothelioma Diseases 0.000 claims description 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 2
- 208000029725 Metabolic bone disease Diseases 0.000 claims description 2
- 208000003445 Mouth Neoplasms Diseases 0.000 claims description 2
- 208000016285 Movement disease Diseases 0.000 claims description 2
- 208000034578 Multiple myelomas Diseases 0.000 claims description 2
- 206010028403 Mutism Diseases 0.000 claims description 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 208000002033 Myoclonus Diseases 0.000 claims description 2
- 208000000175 Nail-Patella Syndrome Diseases 0.000 claims description 2
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims description 2
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims description 2
- 208000037212 Neonatal hypoxic and ischemic brain injury Diseases 0.000 claims description 2
- 208000034176 Neoplasms, Germ Cell and Embryonal Diseases 0.000 claims description 2
- 208000009905 Neurofibromatoses Diseases 0.000 claims description 2
- 244000061176 Nicotiana tabacum Species 0.000 claims description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 2
- 208000001294 Nociceptive Pain Diseases 0.000 claims description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 2
- 206010031096 Oropharyngeal cancer Diseases 0.000 claims description 2
- 206010057444 Oropharyngeal neoplasm Diseases 0.000 claims description 2
- 206010069917 Orthostatic tremor Diseases 0.000 claims description 2
- 206010031243 Osteogenesis imperfecta Diseases 0.000 claims description 2
- 206010049088 Osteopenia Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 206010061334 Partial seizures Diseases 0.000 claims description 2
- 208000002471 Penile Neoplasms Diseases 0.000 claims description 2
- 206010034299 Penile cancer Diseases 0.000 claims description 2
- 206010034912 Phobia Diseases 0.000 claims description 2
- 208000008348 Post-Concussion Syndrome Diseases 0.000 claims description 2
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 2
- 206010065918 Prehypertension Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 206010072377 Psychogenic tremor Diseases 0.000 claims description 2
- 206010037779 Radiculopathy Diseases 0.000 claims description 2
- 206010053632 Reactive psychosis Diseases 0.000 claims description 2
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 2
- 206010038389 Renal cancer Diseases 0.000 claims description 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 2
- 208000006289 Rett Syndrome Diseases 0.000 claims description 2
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 claims description 2
- 206010061934 Salivary gland cancer Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 208000030988 Schizoid Personality disease Diseases 0.000 claims description 2
- 208000020186 Schizophreniform disease Diseases 0.000 claims description 2
- 208000024791 Schizotypal Personality disease Diseases 0.000 claims description 2
- 208000008765 Sciatica Diseases 0.000 claims description 2
- 206010039917 Selective mutism Diseases 0.000 claims description 2
- 208000000810 Separation Anxiety Diseases 0.000 claims description 2
- 206010073677 Severe myoclonic epilepsy of infancy Diseases 0.000 claims description 2
- 208000019568 Shared Paranoid disease Diseases 0.000 claims description 2
- 208000028810 Shared psychotic disease Diseases 0.000 claims description 2
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 2
- 206010041250 Social phobia Diseases 0.000 claims description 2
- 208000032383 Soft tissue cancer Diseases 0.000 claims description 2
- 208000029033 Spinal Cord disease Diseases 0.000 claims description 2
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 206010042928 Syringomyelia Diseases 0.000 claims description 2
- 208000003664 Tarlov Cysts Diseases 0.000 claims description 2
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 2
- 206010057644 Testis cancer Diseases 0.000 claims description 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
- 206010062129 Tongue neoplasm Diseases 0.000 claims description 2
- 206010043994 Tonic convulsion Diseases 0.000 claims description 2
- 206010044074 Torticollis Diseases 0.000 claims description 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 2
- 208000016620 Tourette disease Diseases 0.000 claims description 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 2
- 208000026911 Tuberous sclerosis complex Diseases 0.000 claims description 2
- 206010046431 Urethral cancer Diseases 0.000 claims description 2
- 206010046458 Urethral neoplasms Diseases 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 2
- 208000002495 Uterine Neoplasms Diseases 0.000 claims description 2
- 241000700605 Viruses Species 0.000 claims description 2
- 206010047700 Vomiting Diseases 0.000 claims description 2
- 206010047741 Vulval cancer Diseases 0.000 claims description 2
- 208000004354 Vulvar Neoplasms Diseases 0.000 claims description 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 2
- 208000029650 alcohol withdrawal Diseases 0.000 claims description 2
- 206010053552 allodynia Diseases 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 230000001430 anti-depressive effect Effects 0.000 claims description 2
- 230000000561 anti-psychotic effect Effects 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- 229940005513 antidepressants Drugs 0.000 claims description 2
- 201000011165 anus cancer Diseases 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 2
- 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 claims description 2
- 230000006399 behavior Effects 0.000 claims description 2
- 229940049706 benzodiazepine Drugs 0.000 claims description 2
- 208000022257 bipolar II disease Diseases 0.000 claims description 2
- 201000000053 blastoma Diseases 0.000 claims description 2
- 208000009973 brain hypoxia - ischemia Diseases 0.000 claims description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N butane-1,2,3,4-tetrol Chemical compound OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 230000002490 cerebral effect Effects 0.000 claims description 2
- 206010008129 cerebral palsy Diseases 0.000 claims description 2
- 201000010881 cervical cancer Diseases 0.000 claims description 2
- 238000002512 chemotherapy Methods 0.000 claims description 2
- 208000024825 childhood disintegrative disease Diseases 0.000 claims description 2
- 208000006990 cholangiocarcinoma Diseases 0.000 claims description 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 2
- 230000007882 cirrhosis Effects 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 206010009887 colitis Diseases 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 claims description 2
- 208000018631 connective tissue disease Diseases 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000007547 defect Effects 0.000 claims description 2
- 230000007812 deficiency Effects 0.000 claims description 2
- 208000017004 dementia pugilistica Diseases 0.000 claims description 2
- 206010061811 demyelinating polyneuropathy Diseases 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 150000002016 disaccharides Chemical class 0.000 claims description 2
- 230000000142 dyskinetic effect Effects 0.000 claims description 2
- 208000010118 dystonia Diseases 0.000 claims description 2
- 230000004406 elevated intraocular pressure Effects 0.000 claims description 2
- 201000008184 embryoma Diseases 0.000 claims description 2
- 230000001037 epileptic effect Effects 0.000 claims description 2
- 230000001667 episodic effect Effects 0.000 claims description 2
- 201000004101 esophageal cancer Diseases 0.000 claims description 2
- 201000006517 essential tremor Diseases 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 210000003414 extremity Anatomy 0.000 claims description 2
- 201000010103 fibrous dysplasia Diseases 0.000 claims description 2
- 201000010175 gallbladder cancer Diseases 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- 239000007897 gelcap Substances 0.000 claims description 2
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 2
- 239000003862 glucocorticoid Substances 0.000 claims description 2
- 201000010536 head and neck cancer Diseases 0.000 claims description 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
- 231100000869 headache Toxicity 0.000 claims description 2
- 208000014617 hemorrhoid Diseases 0.000 claims description 2
- 208000007386 hepatic encephalopathy Diseases 0.000 claims description 2
- 208000006454 hepatitis Diseases 0.000 claims description 2
- 231100000283 hepatitis Toxicity 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- 208000003906 hydrocephalus Diseases 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 201000006866 hypopharynx cancer Diseases 0.000 claims description 2
- 208000034287 idiopathic generalized susceptibility to 7 epilepsy Diseases 0.000 claims description 2
- 230000028993 immune response Effects 0.000 claims description 2
- 201000008319 inclusion body myositis Diseases 0.000 claims description 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 2
- 208000020658 intracerebral hemorrhage Diseases 0.000 claims description 2
- 208000014899 intrahepatic bile duct cancer Diseases 0.000 claims description 2
- 238000007918 intramuscular administration Methods 0.000 claims description 2
- 238000007913 intrathecal administration Methods 0.000 claims description 2
- 230000002601 intratumoral effect Effects 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 201000010982 kidney cancer Diseases 0.000 claims description 2
- 206010023841 laryngeal neoplasm Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000019423 liver disease Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 208000020984 malignant renal pelvis neoplasm Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 2
- 150000002772 monosaccharides Chemical class 0.000 claims description 2
- 201000003152 motion sickness Diseases 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 230000003387 muscular Effects 0.000 claims description 2
- 201000006938 muscular dystrophy Diseases 0.000 claims description 2
- 206010028417 myasthenia gravis Diseases 0.000 claims description 2
- 201000000050 myeloid neoplasm Diseases 0.000 claims description 2
- 230000002151 myoclonic effect Effects 0.000 claims description 2
- 201000010193 neural tube defect Diseases 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 201000004931 neurofibromatosis Diseases 0.000 claims description 2
- 230000000926 neurological effect Effects 0.000 claims description 2
- 208000021722 neuropathic pain Diseases 0.000 claims description 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 206010029864 nystagmus Diseases 0.000 claims description 2
- 208000001797 obstructive sleep apnea Diseases 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229940127240 opiate Drugs 0.000 claims description 2
- 201000005443 oral cavity cancer Diseases 0.000 claims description 2
- 201000006958 oropharynx cancer Diseases 0.000 claims description 2
- 230000000010 osteolytic effect Effects 0.000 claims description 2
- 201000008968 osteosarcoma Diseases 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 208000019906 panic disease Diseases 0.000 claims description 2
- 208000024817 paranoid personality disease Diseases 0.000 claims description 2
- 208000002851 paranoid schizophrenia Diseases 0.000 claims description 2
- 208000033300 perinatal asphyxia Diseases 0.000 claims description 2
- 208000028169 periodontal disease Diseases 0.000 claims description 2
- 230000003239 periodontal effect Effects 0.000 claims description 2
- 230000002093 peripheral effect Effects 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000955 prescription drug Substances 0.000 claims description 2
- 230000001107 psychogenic effect Effects 0.000 claims description 2
- 206010038038 rectal cancer Diseases 0.000 claims description 2
- 201000001275 rectum cancer Diseases 0.000 claims description 2
- 208000015347 renal cell adenocarcinoma Diseases 0.000 claims description 2
- 201000007444 renal pelvis carcinoma Diseases 0.000 claims description 2
- 208000022610 schizoaffective disease Diseases 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 208000025874 separation anxiety disease Diseases 0.000 claims description 2
- 201000008261 skin carcinoma Diseases 0.000 claims description 2
- 201000002859 sleep apnea Diseases 0.000 claims description 2
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 2
- 201000001716 specific phobia Diseases 0.000 claims description 2
- 208000020431 spinal cord injury Diseases 0.000 claims description 2
- 208000005198 spinal stenosis Diseases 0.000 claims description 2
- 201000011549 stomach cancer Diseases 0.000 claims description 2
- 238000007920 subcutaneous administration Methods 0.000 claims description 2
- 150000005846 sugar alcohols Chemical class 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 239000006188 syrup Substances 0.000 claims description 2
- 235000020357 syrup Nutrition 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 201000003120 testicular cancer Diseases 0.000 claims description 2
- 201000002510 thyroid cancer Diseases 0.000 claims description 2
- 201000006134 tongue cancer Diseases 0.000 claims description 2
- 230000009529 traumatic brain injury Effects 0.000 claims description 2
- 208000009999 tuberous sclerosis Diseases 0.000 claims description 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- 206010046766 uterine cancer Diseases 0.000 claims description 2
- 206010046885 vaginal cancer Diseases 0.000 claims description 2
- 208000013139 vaginal neoplasm Diseases 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 208000009935 visceral pain Diseases 0.000 claims description 2
- 230000008673 vomiting Effects 0.000 claims description 2
- 201000005102 vulva cancer Diseases 0.000 claims description 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 description 35
- 150000002430 hydrocarbons Chemical group 0.000 description 27
- 208000024891 symptom Diseases 0.000 description 20
- YJYIDZLGVYOPGU-UHFFFAOYSA-N cannabigeroldivarin Natural products CCCC1=CC(O)=C(CC=C(C)CCC=C(C)C)C(O)=C1 YJYIDZLGVYOPGU-UHFFFAOYSA-N 0.000 description 17
- 229950011318 cannabidiol Drugs 0.000 description 15
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 description 15
- 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 description 15
- 206010061218 Inflammation Diseases 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 230000004054 inflammatory process Effects 0.000 description 13
- 241000699666 Mus <mouse, genus> Species 0.000 description 11
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 10
- 230000006872 improvement Effects 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- 231100000673 dose–response relationship Toxicity 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 239000013626 chemical specie Substances 0.000 description 6
- 230000037406 food intake Effects 0.000 description 6
- 210000000548 hind-foot Anatomy 0.000 description 6
- 125000004043 oxo group Chemical group O=* 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 230000037396 body weight Effects 0.000 description 5
- 229940065144 cannabinoids Drugs 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 208000012285 hip pain Diseases 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 108010028275 Leukocyte Elastase Proteins 0.000 description 4
- 102000016799 Leukocyte elastase Human genes 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- 210000000440 neutrophil Anatomy 0.000 description 4
- 230000007958 sleep Effects 0.000 description 4
- 230000005586 smoking cessation Effects 0.000 description 4
- 208000006820 Arthralgia Diseases 0.000 description 3
- 208000004930 Fatty Liver Diseases 0.000 description 3
- 208000008589 Obesity Diseases 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229920000392 Zymosan Polymers 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 210000003127 knee Anatomy 0.000 description 3
- 208000024765 knee pain Diseases 0.000 description 3
- 235000020824 obesity Nutrition 0.000 description 3
- 238000003305 oral gavage Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 2
- 102000003896 Myeloperoxidases Human genes 0.000 description 2
- 108090000235 Myeloperoxidases Proteins 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 230000009429 distress Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 description 2
- 229960004171 hydroxychloroquine Drugs 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 102100036475 Alanine aminotransferase 1 Human genes 0.000 description 1
- 108010082126 Alanine transaminase Proteins 0.000 description 1
- 206010002869 Anxiety symptoms Diseases 0.000 description 1
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 1
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 1
- 208000025721 COVID-19 Diseases 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 108010008165 Etanercept Proteins 0.000 description 1
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010068319 Oropharyngeal pain Diseases 0.000 description 1
- 241000452413 Sabra Species 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 206010043515 Throat cancer Diseases 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- OXQKEKGBFMQTML-UHFFFAOYSA-N alpha-Glucoheptitol Chemical compound OCC(O)C(O)C(O)C(O)C(O)CO OXQKEKGBFMQTML-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 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 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940073621 enbrel Drugs 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 231100000753 hepatic injury Toxicity 0.000 description 1
- 235000009200 high fat diet Nutrition 0.000 description 1
- 229940048921 humira Drugs 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000011503 in vivo imaging Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229960002725 isoflurane Drugs 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000013227 male C57BL/6J mice Methods 0.000 description 1
- 238000003753 real-time PCR Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229940116176 remicade Drugs 0.000 description 1
- 238000010839 reverse transcription Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000003860 sleep quality Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000023409 throat pain Diseases 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
Definitions
- Cannabinoids are generally insoluble in water and glycerol. Some aspects of the disclosure relate to the discovery that the conversion of cannabinoid molecules into anions under alkaline conditions improves their solubility, bioavailability, and pharmacokinetics. Some aspects of the disclosure relate to the discovery that cannabigerol and related cannabinoids can inhibit tumor necrosis factor alpha (“TNF-alpha”) signaling pathways in animal models and that the cannabigerol anion can treat health conditions in humans that are sensitive to TNF-alpha signaling pathway inhibitors including Crohn’s disease and plaque psoriasis. Some aspects of the disclosure relate to the discovery that cannabinoids can reduce pain and inflammation in both animal models and humans.
- TNF-alpha tumor necrosis factor alpha
- Some aspects of the disclosure relate to the discovery that the topical administration of the cannabigerol anion can treat health conditions including peripheral neuropathy and plaque psoriasis in humans. Some aspects of the disclosure relate to the discovery that the oral administration of the cannabidiol anion can arrest active seizures in animals.
- compositions comprising one or both of a cannabinoid molecule and a cannabinoid anion, wherein the cannabinoid molecule has an acid dissociation constant in water of at least 50 femtomolar and no greater than 50 nanomolar for conversion of the cannabinoid molecule into the cannabinoid anion; the cannabinoid anion has the general structure I
- R1 is a straight or branched C1-C12 alkyl that is optionally substituted with phenyl or a cycloalkyl; R2 is methyl; and R3 is methyl; the composition is effective to treat or prophylactically prevent a health condition; aberrant tumor necrosis factor alpha TNF-alpha signaling either causes or exacerbates the health condition; and the composition is effective to inhibit TNF-alpha-mediated signaling pathways.
- composition comprising one or both of a cannabinoid molecule and a cannabinoid anion can also comprise, for example a cation.
- Cannabinoid molecule refers to a cannabinoid chemical species that lacks a net charge
- cannabinoid anion refers to a cannabinoid chemical species that comprises a net negative charge.
- Various cannabinoid molecules and anions are described in PCT Patent Application Publication No. W02020123809, PCT Patent Application Publication No. WO2020123976, PCT Patent Application Publication No. WO2020264199, U.S. Patent No. 10,555,914, and U.S. Patent No. 10,609,944, which are incorporated by reference for the chemical species that they disclose.
- “Straight or branched Cl -Cl 2 alkyl” refers to a straight or branched hydrocarbon chain having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms, wherein all carbon-carbon bonds in the hydrocarbon chain are single bonds.
- Substituted with phenyl or a cycloalkyl refers to the substitution of at least one hydrogen atom of a hydrocarbon chain with either phenyl or a cycloalkyl.
- Cycloalkyl refers to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and adamantyl.
- a hydrocarbon chain is substituted by a cycloalkyl, then either (i) a single hydrogen atom of the hydrocarbon chain is substituted with the cycloalkyl such that the cycloalkyl does not include any carbon atom of the hydrocarbon chain, or (ii) two hydrogen atoms of the hydrocarbon chain are substituted with the cycloalkyl such that the cycloalkyl comprises one or more carbon atoms of the hydrocarbon chain.
- the carbon atoms of a cycloalkyl are included in the carbon atoms of a hydrocarbon chain that is substituted by the cycloalkyl when counting the number of atoms in the hydrocarbon chain.
- Treat refers to at least one of: to cure a health condition; to increase the probability that a health condition will be cured; to shorten the time over which a health condition is cured; to increase the probability that the time necessary to cure a health condition will be shortened; to decrease the severity of a health condition; to increase the probability that the severity of a health condition will decrease; to shorten the time over which the severity of a health condition is decreased; to increase the probability that the time necessary to decrease the severity of a health condition will be shortened; to inhibit a health condition from worsening; to increase the probability that a health condition will not worsen; to delay the worsening of a health condition; to increase the probability that the worsening of a health condition will be delayed; to inhibit the occurrence or recurrence of a health condition; to decrease the probability that a health condition will occur or reoccur; to delay the onset of a health condition; to increase the probability that the onset of a health condition will be delayed; to alleviate at least one
- the health condition is Crohn’s Disease.
- the health condition is inflammatory bowel disease. In some embodiments, the health condition is colitis.
- the health condition is psoriasis.
- the health condition is plaque psoriasis.
- the health condition is arthritis.
- the health condition is Dupuytren’s disease.
- the health condition is lupus.
- the composition is formulated for topical administration.
- compositions comprising a liquid phase that comprises one or both of a cannabinoid molecule and a cannabinoid anion, wherein the cannabinoid molecule has an acid dissociation constant in water of at least 50 femtomolar and no greater than 50 nanomolar for conversion of the cannabinoid molecule into the cannabinoid anion; the liquid phase has a combined molar concentration of the cannabinoid molecule and the cannabinoid anion in the liquid phase that is greater than the solubility of the cannabinoid molecule in the liquid phase; and the liquid phase comprises glycerol at a concentration of at least 50 percent by mass.
- Molar concentration refers to concentrations in both liquid phases and solid phases, and when the molar concentration refers to a liquid phase, then the molar concentration is limited to the concentration of either a solvent or a solute that is dissolved in a solvent.
- Dissolved refers to a solute that is solvated in a liquid phase; a chemical species that is present within a phase that is dispersed within a liquid phase, such as the dispersed phase of an emulsion, is not dissolved in the liquid phase; a chemical species that is non-covalently bound to any chemical species that is a solid in the absence of a solvent, such as a cyclodextrin, is not dissolved in a liquid phase.
- the composition comprises the cannabinoid anion.
- the composition comprises the cannabinoid molecule.
- the liquid phase is supersaturated with the cannabinoid molecule.
- the composition is prepared by contacting a composition that comprises a cannabinoid anion with an acid.
- the liquid phase comprises ethanol at a concentration of at least 10 percent by mass.
- compositions comprising a solid phase and a liquid phase, wherein the solid phase comprises one or more carbohydrates; the liquid phase comprises one or both of a cannabinoid molecule and a cannabinoid anion; and the cannabinoid molecule has an acid dissociation constant in water of at least 50 femtomolar and no greater than 50 nanomolar for conversion of the cannabinoid molecule into the cannabinoid anion.
- the composition comprises the solid phase and the liquid phase at a mass ratio of at least 4: 1 and no greater than 249: 1.
- the one or more carbohydrates are selected from monosaccharides, disaccharides, and sugar alcohols.
- the one or more carbohydrates are selected from butane-1, 2, 3, 4-tetrol; pentane-l,2,3,4,5-pentol; cyclohexane- 1, 2, 3, 4, 5, 6-hexol; hexane-l,2,3,4,5,6-hexol; and heptane- 1, 2, 3, 4,5,6, 7-heptol.
- the one or more carbohydrates consist of xylitol.
- Consist of refers to a closed set such that one or more carbohydrates that consist of xylitol cannot also comprise, for example, sucrose.
- a composition may nevertheless comprise a carbohydrate that is not included in the one or more carbohydrates, but any such additional carbohydrate is not included, for example, when calculating a concentration of the one or more carbohydrates.
- At least 50 percent by mass of the one or more carbohydrates are crystalline.
- the solid phase comprises the one or more carbohydrates at a concentration of at least 50 percent by mass.
- the liquid phase comprises one or both of ethanol and propylene glycol.
- the liquid phase comprises the cannabinoid molecule.
- the liquid phase comprises the cannabinoid anion.
- compositions comprising a solid phase that comprises a cannabinoid anion and a cation, wherein the composition comprises the cannabinoid anion and the cation at a combined concentration of no greater than 50 percent by mass.
- the composition comprises the cannabinoid anion and the cation at a combined concentration of at least 0.1 percent and no greater than 10 percent by mass.
- the cannabinoid anion has the general structure I, II, or III I
- R1 is selected from hydro; a straight or branched C1-C12 alkyl or alkoxy that is optionally substituted with hydroxy, cyano, phenyl, a cycloalkyl, or 1, 2, or 3 halogens; and a straight or branched C2-C12 ether, alkenyl, or alkynyl that is optionally substituted with hydroxy, cyano, phenyl, a cycloalkyl, or 1, 2, or 3 halogens; R2 is selected from hydro; hydroxy; oxo; a straight or branched Cl -CIO alkyl, alkoxy, or alkenyl that is optionally substituted with hydroxy, oxo, or 1, 2, or 3 halogens; and a straight or branched C2-C10 ether or alkynyl that is optionally substituted with 1, 2, or 3 halogens; R3 is selected from hydro; a straight or branched Cl -CIO alkyl or alken
- “Straight or branched Cl -Cl 2 . . . alkoxy” refers to an alkoxy comprising a straight or branched hydrocarbon chain having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms.
- “Substituted with hydroxy, cyano, phenyl, a cycloalkyl, or 1, 2, or 3 halogens” refers to the substitution of a hydrogen atom of a hydrocarbon chain with either hydroxy, cyano, phenyl, a cycloalkyl, or 1, 2, or 3 halogens.
- Halogen refers to F, Cl, Br, and I.
- “Straight or branched C2-C12 ether” refers to a straight or branched ether having 1 oxygen atom and 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms.
- “Straight or branched C2-C12 . . . alkenyl” refers to a straight or branched hydrocarbon chain having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms, wherein at least one carbon-carbon bond in the hydrocarbon chain is a double bond and/or the hydrocarbon chain is an ylidene, and wherein no carbon-carbon bond in the hydrocarbon chain is a triple bond.
- Ylidene refers to an alkenyl or alkynyl that includes a carbon-carbon double bond that connects the alkenyl or alkynyl to general structure II or III or an R3 that includes a carbon-carbon double bond that connects the R3 to general structure II.
- An example of an ylidene is methylidene.
- “Straight or branched C2-C12 . . . alkynyl” refers to a straight or branched hydrocarbon chain having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms, wherein at least one carbon-carbon bond in the hydrocarbon chain is a triple bond.
- “Straight or branched Cl -CIO alkyl” refers to a straight or branched hydrocarbon chain having 1,
- “Straight or branched Cl -CIO . . . alkoxy” refers to a straight or branched alkoxy chain having 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms.
- “Straight or branched Cl -CIO . . . alkenyl” refers to a straight or branched hydrocarbon chain having 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms, wherein at least one carbon-carbon bond in the hydrocarbon chain is a double bond and/or the hydrocarbon chain is an ylidene, and wherein no carbon-carbon bond in the hydrocarbon chain is a triple bond.
- Substituted with . . . oxo refers to the substitution of two hydrogen atoms that are bound to the same carbon atom of a hydrocarbon chain with an oxo group.
- “Straight or branched C2-C10 ether” refers to a straight or branched ether having 1 oxygen atom and 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms.
- “Straight or branched C2-C10 alkynyl” refers to a straight or branched hydrocarbon chain having 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms, wherein at least one carbon-carbon bond in the hydrocarbon chain is a triple bond.
- the cannabinoid anion has the general structure I; R1 is a straight or branched C1-C12 alkyl that is optionally substituted with phenyl; R2 is methyl; and R3 is methyl.
- the cannabinoid anion has the general structure II;
- R1 is a straight or branched C1-C12 alkyl that is optionally substituted with phenyl or cycloalkyl;
- R2 is a straight or branched C1-C4 alkyl or ether that is optionally substituted with hydroxy, oxo, or a halogen;
- R3 is methyl, methylidene, hydroxymethyl, fluoromethyl, or a straight or branched C2-C4 alkyl, alkenyl, or alkynyl that is optionally substituted with hydroxy or a halogen.
- the cannabinoid anion has the general structure III;
- R1 is a straight or branched C1-C12 alkyl that is optionally substituted with phenyl or cycloalkyl;
- R2 is a straight or branched C1-C4 alkyl or ether that is optionally substituted with hydroxy, oxo, or a halogen;
- R3 is methyl, hydroxymethyl, fluoromethyl, or a straight or branched C2-C4 alkyl, alkenyl, or alkynyl that is optionally substituted with hydroxy or a halogen.
- R1 is hydro; methyl; ethyl; propyl; butyl; pentyl; hexyl; heptyl; octyl; nonyl; decyl; prop-2 -yl; but-2-yl; pent-2-yl; hex-2-yl; hept-2-yl; octan-2-yl; nonan-2-yl; decan-2 -yl; 2-methylpropyl; 2-methylbutyl; 2-methylpentyl; 2-methylhexyl; 2-methylheptyl; 2-methyloctyl; 2- methylnonyl; 2-methyldecyl; 2-methylprop-2-yl; 2-methylbut-2-yl; 2-methylpent-2-yl; 2- methylhex-2-yl; 2-methylhept-2-yl; 2-methyloctan-2-yl; 2-methylnonan-2-yl; 2-methyldecan-2-yl;
- R2 is methyl
- the cannabinoid anion has the general structure I or III, and R3 is methyl.
- the cannabinoid anion has the general structure II, and R3 is methylidene.
- the cannabinoid anion is 2-geranyl-3-hydroxy-5-pentylphenolate.
- the cannabinoid anion is 2-geranyl-3-hydroxy-5-propylphenolate.
- the cannabinoid anion is 3-hydroxy-2-(6-isopropenyl-3-methylcyclohex-2- enyl)-5-pentylphenolate.
- the cannabinoid anion is 3-hydroxy-2-(6-isopropenyl-3-methylcyclohex-2- enyl)-5-propylphenolate.
- the cannabinoid anion is 6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro- 6H-benzo[c]chromene-l -oxide.
- the cannabinoid anion is 6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro- 6H-benzo[c]chromene-l -oxide.
- the cannabinoid anion is 6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene- 1 -oxide.
- the cannabinoid anion is 6,6,9-trimethyl-3-propyl-6H-benzo[c]chromene- 1 -oxide.
- the composition is for use as a medicament.
- the composition is formulated to convert the cannabinoid anion into the cannabinoid molecule ex vivo prior to administering the composition to a subject.
- the composition is formulated to convert the cannabinoid anion into the cannabinoid molecule in situ subsequent to administering the composition to a subject.
- the composition is formulated for enteral; oral; rectal; sublingual; sublabial; buccal; intranasal; inhalational; transmucosal; topical; transdermal; intravenous; intramuscular; subcutaneous; intradermal; intraocular; parenteral; intrathecal; intralesional; or intratumoral administration.
- the composition is formulated for topical or transdermal administration.
- the composition is a liquid; beverage; elixir; tincture; syrup; pill; tablet; capsule; gel cap; soft gel; gummy; gel; cream; lotion; balm; salve; ointment; dermal patch; transdermal patch; powder; or suppository.
- the composition is a gel; cream; lotion; balm; salve; ointment; dermal patch; or transdermal patch.
- the composition is formulated for oral administration to a subject; the composition is formulated to allow the conversion of the cannabinoid anion into the cannabinoid molecule before the cannabinoid anion reaches the stomach of the subject; and the composition is formulated to allow absorption of the cannabinoid molecule by the epithelial lining of the gastrointestinal tract between the lips and the stomach, excluding the stomach and the outer surfaces of the lips, and including the esophagus and the inner surfaces of the lips.
- Various aspects of this disclosure relate to a method to administer a cannabinoid, comprising providing a composition described anywhere in this disclosure, and administering the composition to a subject.
- the method comprises converting the cannabinoid anion into the cannabinoid molecule ex vivo prior to the administering.
- the method comprises converting the cannabinoid anion into the cannabinoid molecule in situ subsequent to the administering.
- the administering is oral administering; the composition is formulated to allow the conversion of the cannabinoid anion into the cannabinoid molecule before the cannabinoid anion reaches the stomach of the subject; and the composition is formulated to allow absorption of the cannabinoid molecule by the epithelial lining of the gastrointestinal tract between the lips and the stomach, excluding the stomach and the outer surfaces of the lips, and including the esophagus and the inner surfaces of the lips.
- the administering is topical administering.
- the subject presents with a health condition or a risk of developing a health condition.
- the composition is administered in an amount that is effective to treat or prophylactically prevent the health condition.
- the cannabinoid molecule is effective to treat or prophylactically prevent the health condition; the amount lacks the cannabinoid molecule at a concentration that is effective to treat or prophylactically prevent the health condition; and the amount comprises the cannabinoid anion at a concentration that is effective to treat or prophylactically prevent the health condition.
- the amount comprises at least 10 micrograms and no greater than 100 milligrams of the cannabinoid anion.
- the amount comprises at least 10 micrograms and no greater than 200 milligrams of the cannabinoid anion per day.
- the health condition is type 2 diabetes mellitus.
- the health condition is metabolic syndrome.
- the health condition is hypertension.
- the health condition is pre-hypertension.
- the health condition is a neurodegenerative disease or neuropathy.
- the health condition is mild cognitive impairment, Alzheimer’s Disease, Parkinson’s Disease, amyotrophic lateral sclerosis (“ALS”), or Huntington’s disease.
- ALS amyotrophic lateral sclerosis
- the health condition is an autoimmune disorder.
- the health condition is arthritis.
- the health condition is an inflammatory autoimmune-mediated arthritis.
- the health condition is ankylosing spondylitis.
- the health condition is an inflammatory autoimmune-mediated arthritis.
- the health condition is rheumatoid arthritis.
- the health condition is juvenile idiopathic arthritis.
- the health condition is polyarticular juvenile idiopathic arthritis. In some embodiments, the health condition is osteoarthritis.
- the health condition is enthesitis-related arthritis.
- the health condition is psoriatic arthritis.
- the health condition is psoriasis.
- the health condition is plaque psoriasis.
- the health condition is hidradenitis suppurativa.
- the health condition is sarcoidosis.
- the health condition is pulmonary sarcoidosis.
- the health condition is bone sarcoidosis.
- the health condition is lupus.
- the health condition is axial spondyloarthritis.
- the health condition is ankylosing spondylitis.
- the health condition is Dupuytren’s disease.
- the health condition is uveitis.
- the health condition is non-infectious uveitis.
- the health condition is adhesive capsulitis.
- the health condition is Sjogren’s syndrome.
- the health condition is inflammatory bowel disease.
- the health condition is Crohn’s disease.
- the health condition is ulcerative colitis.
- the health condition is smoking-cessation-induced ulcerative colitis.
- the health condition is a headache, a migraine headache, or an episodic migraine.
- the health condition is pain.
- the health condition is nociceptive pain; allodynia; chronic pain; intractable pain; back pain; lower back pain; chronic back pain; sciatica; spinal stenosis; chronic radiculopathy; post laminectomy syndrome; stomach pain; visceral pain; interstitial cystitis; postherpetic neuralgia; sickle cell anemia; sickle cell disease; cancer pain; intractable cancer pain; fibromyalgia; neurogenic pain; neuropathic pain; peripheral neuropathy; inflammatory demyelinating polyneuropathy; peripheral pain; reflex sympathetic dystrophy; residual limb pain; idiopathic pain; psychogenic pain; causalgia; complex regional pain syndrome; complex regional pain syndrome type I; complex regional pain syndrome type II; gout; epidermolysis bullosa; hemorrhoids; or constipation.
- the health condition is elevated intraocular pressure or glaucoma.
- the health condition is liver disease; non-alcoholic fatty liver disease (“NAFLD”); non-alcoholic steatohepatitis (“NASH”); liver cirrhosis; decompensated cirrhosis; hepatic encephalopathy; hepatitis; or hepatitis C.
- the health condition is nausea; cachexia; anorexia; bulimia; vomiting; motion sickness; cancer chemotherapy-induced anorexia; human deficiency virus (“HIV”) infection related nausea or cachexia; or acquired immune deficiency syndrome (“AIDS”) related nausea or cachexia.
- HIV human deficiency virus
- AIDS acquired immune deficiency syndrome
- the health condition is anxiety; generalized anxiety disorder; a specific phobia; agoraphobia; social anxiety disorder; separation anxiety disorder; panic disorder; selective mutism; obsessive-compulsive disorder; depression; a major depressive disorder with psychotic feature(s); psychotic depression; paranoia; psychosis; early psychosis; an unspecified psychosis; an unspecified reactive psychosis; a psychotic disorder; a brief psychotic disorder; a debilitating psychiatric disorder; schizophrenia; schizophreniform disorder; schizoaffective disorder; paranoid personality disorder; schizoid personality disorder; schizotypal personality disorder; a shared psychotic disorder; a shared paranoia disorder; a delusional disorder; bipolar disorder; bipolar I disorder; bipolar II disorder; mania; manic disorder; or manic-depressive psychosis.
- the health condition is an addiction.
- the health condition is an addiction to alcohol, tobacco, nicotine, an opiate, a stimulant, a prescription drug, gambling, food, shopping, the internet, or sex.
- the health condition is drug withdrawal; alcohol withdrawal syndrome; nicotine withdrawal; opioid withdrawal; cannabis withdrawal; benzodiazepine withdrawal syndrome; antidepressant discontinuation syndrome; antipsychotic withdrawal syndrome; addictive behavior; or cannabis use disorder.
- the health condition is attention deficit hyperactivity disorder (“ADHD”); autism or an autism spectrum disorder; Asperger syndrome; fragile X syndrome; a pervasive developmental disorder not otherwise specified (“PDD-NOS”); a childhood disintegrative disorder; or Tourette’s syndrome.
- ADHD attention deficit hyperactivity disorder
- autism or an autism spectrum disorder Asperger syndrome
- fragile X syndrome a pervasive developmental disorder not otherwise specified
- PPD-NOS pervasive developmental disorder not otherwise specified
- a childhood disintegrative disorder or Tourette’s syndrome.
- the health condition is Down syndrome.
- the health condition is post-traumatic stress disorder (“PTSD”).
- PTSD post-traumatic stress disorder
- the health condition is asthma; respiratory disease; chronic lower respiratory disease; or chronic obstructive pulmonary disease (“COPD”).
- COPD chronic obstructive pulmonary disease
- the health condition is insomnia; sleep apnea; obstructive sleep apnea; or restless legs syndrome.
- the health condition is cramping; muscle spasms; spasticity; spasmodic torticollis; a dyskinetic movement disorder; dystonia; intractable spasticity; intractable skeletal muscular spasticity; inclusion body myositis; myasthenia gravis; muscular dystrophy; Duchenne muscular dystrophy; muscle tremor; cerebellar tremor; dystonic tremor; essential tremor; orthostatic tremor; Parkinsonian tremor; physiological tremor; psychogenic tremor; rubral tremor; or nystagmus.
- the health condition is a seizure disorder.
- the health condition is recurrent focal seizures; recurrent generalized seizures; recurrent absence seizures; recurrent myoclonic-absence seizures; recurrent myoclonus; recurrent myoclonic seizures; recurrent tonic seizures; recurrent tonic-clonic seizures; recurrent atonic seizures; recurrent chronic seizures; epilepsy; recurrent epileptic spasms; refractory epilepsy; intractable epilepsy; treatment-resistant epilepsy; Lennox-Gastaut syndrome; Dravet syndrome; febrile infection related epilepsy syndrome (“FIRES”); juvenile myoclonic epilepsy; myoclonic absence seizures (“MAS”); myoclonic astatic epilepsy (“MAE”); tuberous sclerosis complex (“TSC”); Rett syndrome; or Angelman syndrome.
- the health condition is a neurological condition.
- the health condition is stroke; hemorrhagic stroke; ischemic stroke; neonatal hypoxic-ischemic encephalopathy (“NHIE”); hydrocephalus; hydromyelia; traumatic brain injury (“TBI”); post-concussion syndrome; chronic traumatic encephalopathy; a spinal cord injury; a spinal cord disease; syringomyelia; Tarlov cysts; cystic fibrosis; cerebral palsy; spinocerebellar ataxia; a neural-tube defect; neuropathy; a brain tumor; glioblastoma multiforme; glioblastoma astrocytoma; neurofibromatosis; Arnold-Chiari malformation; or multiple sclerosis.
- the health condition is a connective tissue disorder.
- the health condition is Ehlers-Danlos syndrome; fibrous dysplasia; osteogenesis imperfecta; nail-patella syndrome; idiopathic pulmonary fibrosis; bone loss; bone loss caused by a bone fracture; bone loss caused by a surgical procedure; a periodontal defect; periodontal disease; osteopenia; an osteolytic bone disease; osteoporosis; age-related osteoporosis; hormone-related osteoporosis; hypogonadism-related osteoporosis; diabetes-related osteoporosis; glucocorticoid-related osteoporosis; or disuse osteoporosis.
- the health condition is a carcinoma; sarcoma; lymphoma; leukemia; germ cell tumor; or blastoma.
- the health condition is brain cancer; ovarian cancer; breast cancer; vaginal cancer; vulvar cancer; uterine cancer; cervical cancer; endometrial cancer; prostate cancer; testicular cancer; penile cancer; liver cancer; intrahepatic bile duct cancer; lung cancer; small cell lung cancer; non-small cell lung cancer; bronchial cancer; mesothelioma; pancreatic cancer; gall bladder cancer; non-melanoma skin cancer; melanoma; Kaposi sarcoma; thyroid cancer; head and neck cancer; nasopharyngeal cancer; oropharyngeal cancer; hypopharyngeal cancer; laryngeal cancer; oral cavity cancer; tongue cancer; mouth cancer; salivary gland cancer; esophageal cancer; gastric cancer; colorectal cancer; colon cancer; rectal cancer; anal cancer; kidney cancer; renal cell cancer; renal pelvis cancer; bladder cancer; urethral cancer; Hodgkin lymphoma; non-Hodgkin’
- the health condition is an autoimmune disease
- the composition is administered to inhibit aberrant immune response in the subject.
- aberrant TNF-alpha signaling causes the health condition, and the composition is administered to inhibit TNF-alpha-mediated signaling pathways.
- aberrant TNF-alpha signaling exacerbates the health condition, and the composition is administered to inhibit TNF-alpha-mediated signaling pathways.
- Example 1 Cannabigerol and cannabigerovarin inhibit pain, inflammation, and TNF-alpha- mediated signaling pathways in a mouse arthritis model.
- mice are administered either vehicle or a cannabinoid.
- the cannabinoid is selected from 2-geranyl-5-pentylbenzene-l,3-diol (“cannabigerol”) and 2-geranyl-5-propylbenzene-l,3-diol (“cannabigerovarin”).
- the cannabinoid is administered at an amount of either 1, 2, 4, 8, 16, 32, or 64 milligrams cannabinoid per kilogram mouse body weight per day by oral gavage beginning when they are two months old.
- mice Following one month of administration of either vehicle or a cannabinoid, 30 microliters of a 2 percent weight-by-volume suspension of zymosan A in saline is injected into each right hind paw of the mice. Inflammation is measured with calipers to determine right hind paw swelling at 1, 2, 6, 12, and 24 hours following the zymosan A injection relative to left hind paw. Pain is measured with a Von Frey hair aesthesiometer to determine right hind paw sensitivity to force relative to left hind paw. Serum TNF-alpha concentration is measured at 24 hours by enzyme-linked immunosorbent assay.
- Each of the cannabigerol and cannabigerovarin groups display a dose-dependent reduction in right hind paw inflammation and pain relative to vehicle control groups.
- Each of the cannabigerol and cannabigerovarin groups display a dose-dependent reduction in serum TNF-alpha concentration relative to vehicle control groups.
- Example 2 Cannabigerol and cannabigerovarin inhibit neutrophil-mediated inflammation in a mouse arthritis model.
- mice Male C57BL/6J mice are administered either vehicle or a cannabinoid.
- the cannabinoid is selected from cannabigerol and cannabigerovarin.
- the cannabinoid is administered at an amount of either 1, 2, 4, 8, 16, 32, or 64 milligrams cannabinoid per kilogram mouse body weight per day by oral gavage beginning when they are two months old.
- mice are anesthetized with isoflurane and then 180 micrograms of zymosan A in saline is injected into the right knee of each mouse. Equivalent volumes of saline are injected into the left knee of each mouse. Mice are then injected with Neutrophil Elastase 680 FAST imaging probe (Perkin Elmer, Massachusetts, United States) and imaged 4 hours post-injection using an IVIS Spectrum In Vivo Imaging System (Perkin Elmer) to measure neutrophil -mediated inflammation. Mouse RNA is extracted and purified, and then relative adamts4 transcript, relative neutrophil elastase transcript, and relative myeloperoxidase transcript concentrations are measured following reverse transcription using real-time polymerase chain reaction.
- Each of the cannabigerol and cannabigerovarin groups display a dose-dependent reduction in imaged right knee neutrophil elastase relative to vehicle control group.
- Each of the cannabigerol and cannabigerovarin groups display a dose-dependent reduction in adamts4 transcripts, neutrophil elastase transcripts, and myeloperoxidase transcripts relative to vehicle control groups.
- TNF-alpha is known to increase neutrophil-mediated inflammation, which corroborates the hypothesis that each of cannabigerol and cannabigerovarin inhibit TNF-alpha- mediated signaling pathways, and which therefore also corroborates the hypothesis that each of cannabigerol and cannabigerovarin will be effective in humans at treating each of pain; inflammation; arthritis; inflammatory autoimmune-mediated arthritis; rheumatoid arthritis; juvenile idiopathic arthritis; polyarticular juvenile idiopathic arthritis; osteoarthritis; enthesitis-related arthritis; psoriatic arthritis; psoriasis; plaque psoriasis; hidradenitis suppurativa; sarcoidosis; pulmonary sarcoidosis; bone sarcoidosis; lupus; axial spondyloarthritis; ankylosing spondylitis; Dupuytren’s disease; uveitis; non-infectious
- Example 3 Cannabigerol and cannabigerovarin inhibit obesity and liver injury biomarkers in mouse diet-induced obesity models.
- mice Mouse body weights are measured daily. The mice are sacrificed when they are four months old following two months of the diet, cannabinoid (or vehicle), and weighing. Serum alanine aminotransferase (“ALT”) and serum aspartate aminotransferase (“AST”) are measured using a Reflotran Plus blood chemistry system (Roche, Switzerland). Mouse livers are fixed and then stained with hematoxylin and eosin to visualize liver steatosis.
- ALT serum alanine aminotransferase
- AST serum aspartate aminotransferase
- Example 5 Treatment of acute back pain.
- Example 7 Treatment of chronic hip pain.
- Example 8 Treatment of post laminectomy syndrome.
- Example 11 Treatment of chronic pain.
- An individual was administered a beverage containing the cannabidiol anion prior to driving to an airport to catch a flight that was scheduled to depart within thirty minutes of the arrival at the airport.
- the individual reported that he would ordinarily experience anxiety during such a drive when confronted with a similar timeline, and the individual reported a notable absence of anxiety.
- Example 13 Treatment of social anxiety.
- Example 14 Treatment of cramping and restless legs syndrome.
- Example 15 Treatment of epilepsy.
- a dog that suffers from chronic seizures was administered a glycerol tincture containing the cannabidiol anion immediately after the onset of a seizure.
- the owners of the dog reported that the glycerol tincture containing the cannabidiol anion both instantaneously and consistently arrested multiple seizures in the dog and significantly improved the dog’s quality of life.
- Example 16 Treatment of insomnia.
- Example 17 Treatment of Crohn’s disease.
- Example 18 Treatment of Inflammatory Bowel Disease.
- Example 19 Treatment of plaque psoriasis.
- Example 20 Treatment of peripheral neuropathy.
- Example 21 Cannabigerol and cannabigerovarin likely inhibit TNF-alpha signaling in humans.
- Examples 1 and 2 each suggest that each of cannabigerol and cannabigerovarin can inhibit TNF- alpha-mediated signaling pathways in mice, which suggests that each of the foregoing cannabinoids can treat health conditions in humans by inhibiting TNF-alpha-mediated signaling pathways.
- Anti- TNF-alpha pharmaceuticals such as HUMIRA®, REMICADE®, and ENBREL® are known to be effective at treating Crohn’s Disease and plaque psoriasis. Examples 17 and 19 therefore corroborate the hypothesis that each of cannabigerol and cannabigerovarin can treat health conditions in humans by inhibiting TNF-alpha-mediated signaling pathways.
- cannabigerol and cannabigerovarin can treat a range of health conditions in humans including pain; inflammation; arthritis; inflammatory autoimmune-mediated arthritis; rheumatoid arthritis; juvenile idiopathic arthritis; polyarticular juvenile idiopathic arthritis; osteoarthritis; enthesitis-related arthritis; psoriatic arthritis; psoriasis; plaque psoriasis; hidradenitis suppurativa; sarcoidosis; pulmonary sarcoidosis; bone sarcoidosis; lupus; axial spondyloarthritis; ankylosing spondylitis; Dupuytren’s disease; uveitis; non-infectious uveitis; adhesive capsulitis; Sjogren’s syndrome; inflammatory bowel disease; Crohn’s disease; ulcerative colitis; and smoking-cessation-induced ulcerative colitis.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biomedical Technology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Divers aspects de l'invention concernent des compositions comprenant un anion cannabinoïde, l'anion cannabinoïde étant la base conjuguée d'une molécule cannabinoïde, et la molécule cannabinoïde a une constante de dissociation acide dans l'eau d'au moins 50 femtomolaire et non supérieure à 50 nanomolaire pour la conversion de la molécule cannabinoïde en anion cannabinoïde. Dans certains modes de réalisation, une composition est efficace pour inhiber les voies de signalisation médiées par TNF-alpha chez un être humain.
Applications Claiming Priority (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202163148050P | 2021-02-10 | 2021-02-10 | |
| US63/148,050 | 2021-02-10 | ||
| US202163154508P | 2021-02-26 | 2021-02-26 | |
| US202163154482P | 2021-02-26 | 2021-02-26 | |
| US202163154541P | 2021-02-26 | 2021-02-26 | |
| US63/154,508 | 2021-02-26 | ||
| US63/154,541 | 2021-02-26 | ||
| US63/154,482 | 2021-02-26 | ||
| US202163191831P | 2021-05-21 | 2021-05-21 | |
| US202163191874P | 2021-05-21 | 2021-05-21 | |
| US202163191846P | 2021-05-21 | 2021-05-21 | |
| US63/191,874 | 2021-05-21 | ||
| US63/191,831 | 2021-05-21 | ||
| US63/191,846 | 2021-05-21 | ||
| US202163194811P | 2021-05-28 | 2021-05-28 | |
| US63/194,811 | 2021-05-28 | ||
| US202163254431P | 2021-10-11 | 2021-10-11 | |
| US63/254,431 | 2021-10-11 | ||
| US202163256454P | 2021-10-15 | 2021-10-15 | |
| US63/256,454 | 2021-10-15 | ||
| US202163282124P | 2021-11-22 | 2021-11-22 | |
| US63/282,124 | 2021-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2022173812A1 true WO2022173812A1 (fr) | 2022-08-18 |
Family
ID=82837248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2022/015795 WO2022173812A1 (fr) | 2021-02-10 | 2022-02-09 | Compositions et procédés associés à des anions cannabinoïdes |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2022173812A1 (fr) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070060639A1 (en) * | 2005-09-09 | 2007-03-15 | University Of Kentucky | Compositions and methods for intranasal delivery of tricyclic cannabinoids |
| EP3459536A1 (fr) * | 2017-09-25 | 2019-03-27 | Krotov, Vadym | Composition comprenant des cannabinoides et procédé de fabrication correspondant |
| WO2020123809A1 (fr) * | 2018-12-14 | 2020-06-18 | Natural Extraction Systems, LLC | Compositions et procédés se rapportant à des molécules cannabinoïdes anioniques |
| WO2020264199A1 (fr) * | 2019-06-26 | 2020-12-30 | Natural Extraction Systems, LLC | Récipients, compositions, et procédés associés à des anions cannabinoïdes |
-
2022
- 2022-02-09 WO PCT/US2022/015795 patent/WO2022173812A1/fr active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070060639A1 (en) * | 2005-09-09 | 2007-03-15 | University Of Kentucky | Compositions and methods for intranasal delivery of tricyclic cannabinoids |
| EP3459536A1 (fr) * | 2017-09-25 | 2019-03-27 | Krotov, Vadym | Composition comprenant des cannabinoides et procédé de fabrication correspondant |
| WO2020123809A1 (fr) * | 2018-12-14 | 2020-06-18 | Natural Extraction Systems, LLC | Compositions et procédés se rapportant à des molécules cannabinoïdes anioniques |
| WO2020264199A1 (fr) * | 2019-06-26 | 2020-12-30 | Natural Extraction Systems, LLC | Récipients, compositions, et procédés associés à des anions cannabinoïdes |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20230293458A1 (en) | Multibiotic agents and methods of using the same | |
| US11339136B2 (en) | Compounds and compositions for treating conditions associated with NLRP activity | |
| US9284283B2 (en) | Macrocyclic compounds for modulating IL-17 | |
| CN103254119B (zh) | 钠-葡萄糖协同转运蛋白2的抑制剂及其用法 | |
| EA034650B1 (ru) | Ациламинопиримидиновые производные для лечения вирусных инфекций и других заболеваний | |
| US20200188418A1 (en) | Acylated active agents and methods of their use for the treatment of autoimmune disorders | |
| TW200815366A (en) | 4,5-diphenyl-pyrimidinyl-amino substituted carboxylic acids, process for their preparation and their use as pharmaceuticals | |
| TW201245219A (en) | Glycoside derivatives and uses thereof | |
| CA2782704A1 (fr) | Derives de diphenyl-pyrazolopyridines, leur preparation et leur application en tant que modulateurs du recepteur nucleaire not | |
| JP2021525787A (ja) | β−ラクタム化合物とプロベネシドの組み合わせとその使用 | |
| MX2010010866A (es) | Composiciones y metodos para inmunoterapia. | |
| US20170247352A1 (en) | Method for preparing alectinib | |
| EP3112362B1 (fr) | Composé présentant une activité sélective d'agoniste ep2 | |
| WO2022173812A1 (fr) | Compositions et procédés associés à des anions cannabinoïdes | |
| CN104507898A (zh) | 苯酚衍生物及其制备方法和在医药上的应用 | |
| US20150105420A1 (en) | [1,2,4]triazolopyridines and their use as phosphodiesterase inhibitors | |
| JP2021516689A (ja) | １，２−ジアシルグリセロール化合物、その製造方法及びこれを有効成分として含有する免疫調節剤 | |
| WO2022173901A1 (fr) | Compositions et procédés associés à des anions cannabinoïdes | |
| JP2015510517A (ja) | 筋萎縮性側索硬化症の治療方法 | |
| WO2021097163A1 (fr) | Compositions pharmaceutiques comprenant des anions cannabinoïdes | |
| WO2021097150A1 (fr) | Méthodes de prévention et de traitement de problèmes de santé à l'aide d'anions cannabinoïdes | |
| US20210360947A1 (en) | Compositions and methods related to excipients and cannabinoid formulations | |
| CN101472580B (zh) | 过敏性皮炎的治疗或预防药 | |
| JP2002212076A (ja) | 縮合複素環化合物またはその塩を含有する糖尿病の予防または治療薬 | |
| WO2010098298A1 (fr) | Composition pharmaceutique contenant une combinaison d'un composé possédant une activité inhibitrice de la digestion/absorption des nutriments et d'un dérivé de cyclohexanecarboxamide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22753253 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 22753253 Country of ref document: EP Kind code of ref document: A1 |