CA3067512A1 - Cannabidiolic acid esters compositions and uses thereof - Google Patents
Cannabidiolic acid esters compositions and uses thereof Download PDFInfo
- Publication number
- CA3067512A1 CA3067512A1 CA3067512A CA3067512A CA3067512A1 CA 3067512 A1 CA3067512 A1 CA 3067512A1 CA 3067512 A CA3067512 A CA 3067512A CA 3067512 A CA3067512 A CA 3067512A CA 3067512 A1 CA3067512 A1 CA 3067512A1
- Authority
- CA
- Canada
- Prior art keywords
- branched
- straight
- compound according
- disease
- cbda
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 19
- WVOLTBSCXRRQFR-DLBZAZTESA-N cannabidiolic acid Chemical class OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-DLBZAZTESA-N 0.000 title abstract description 95
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 40
- 201000010099 disease Diseases 0.000 claims abstract description 32
- 208000024891 symptom Diseases 0.000 claims abstract description 26
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims description 50
- 230000000694 effects Effects 0.000 claims description 46
- 206010028813 Nausea Diseases 0.000 claims description 43
- 230000008693 nausea Effects 0.000 claims description 42
- 208000019901 Anxiety disease Diseases 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 150000001408 amides Chemical class 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 14
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 claims description 14
- 230000036506 anxiety Effects 0.000 claims description 13
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 claims description 12
- 230000006399 behavior Effects 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 206010062237 Renal impairment Diseases 0.000 claims description 10
- 206010047700 Vomiting Diseases 0.000 claims description 10
- 230000005977 kidney dysfunction Effects 0.000 claims description 10
- 230000008673 vomiting Effects 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 230000001629 suppression Effects 0.000 claims description 9
- 206010010904 Convulsion Diseases 0.000 claims description 8
- 206010008118 cerebral infarction Diseases 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 230000036461 convulsion Effects 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 7
- 206010012335 Dependence Diseases 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- 208000028698 Cognitive impairment Diseases 0.000 claims description 5
- 208000010877 cognitive disease Diseases 0.000 claims description 5
- 230000006870 function Effects 0.000 claims description 5
- 230000001771 impaired effect Effects 0.000 claims description 5
- 230000000241 respiratory effect Effects 0.000 claims description 5
- 230000001568 sexual effect Effects 0.000 claims description 5
- 208000019116 sleep disease Diseases 0.000 claims description 5
- 208000022925 sleep disturbance Diseases 0.000 claims description 5
- 208000000884 Airway Obstruction Diseases 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- 206010061216 Infarction Diseases 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 4
- 206010063837 Reperfusion injury Diseases 0.000 claims description 4
- 208000017442 Retinal disease Diseases 0.000 claims description 4
- 206010038923 Retinopathy Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 4
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 4
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 4
- 230000033115 angiogenesis Effects 0.000 claims description 4
- 230000017531 blood circulation Effects 0.000 claims description 4
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 208000007386 hepatic encephalopathy Diseases 0.000 claims description 4
- 230000007574 infarction Effects 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 208000037906 ischaemic injury Diseases 0.000 claims description 4
- 230000000302 ischemic effect Effects 0.000 claims description 4
- 210000004185 liver Anatomy 0.000 claims description 4
- 208000004296 neuralgia Diseases 0.000 claims description 4
- 230000003961 neuronal insult Effects 0.000 claims description 4
- 208000021722 neuropathic pain Diseases 0.000 claims description 4
- 208000020431 spinal cord injury Diseases 0.000 claims description 4
- 230000009529 traumatic brain injury Effects 0.000 claims description 4
- 206010048010 Withdrawal syndrome Diseases 0.000 claims description 3
- 210000004165 myocardium Anatomy 0.000 claims description 3
- WVOLTBSCXRRQFR-SJORKVTESA-N Cannabidiolic acid Natural products OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@@H]1[C@@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-SJORKVTESA-N 0.000 description 87
- 241000700159 Rattus Species 0.000 description 57
- 238000000034 method Methods 0.000 description 31
- 238000012360 testing method Methods 0.000 description 27
- 230000001154 acute effect Effects 0.000 description 22
- 230000000454 anti-cipatory effect Effects 0.000 description 22
- 238000002474 experimental method Methods 0.000 description 20
- 238000001727 in vivo Methods 0.000 description 20
- 102000005962 receptors Human genes 0.000 description 19
- 108020003175 receptors Proteins 0.000 description 19
- XIGAHNVCEFUYOV-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n-pyridin-2-ylcyclohexanecarboxamide Chemical compound OC(=O)\C=C/C(O)=O.COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCCCC2)C=2N=CC=CC=2)CC1 XIGAHNVCEFUYOV-BTJKTKAUSA-N 0.000 description 13
- 230000027455 binding Effects 0.000 description 13
- 230000001143 conditioned effect Effects 0.000 description 13
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 12
- 230000003750 conditioning effect Effects 0.000 description 11
- 102000017911 HTR1A Human genes 0.000 description 10
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 10
- 101000822895 Homo sapiens 5-hydroxytryptamine receptor 1A Proteins 0.000 description 9
- 230000004913 activation Effects 0.000 description 9
- 210000002683 foot Anatomy 0.000 description 9
- 238000000338 in vitro Methods 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- 230000035939 shock Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 238000000540 analysis of variance Methods 0.000 description 8
- 239000012528 membrane Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 230000000638 stimulation Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 229950011318 cannabidiol Drugs 0.000 description 6
- 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 6
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 230000001404 mediated effect Effects 0.000 description 6
- 230000036515 potency Effects 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000000556 agonist Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000001684 chronic effect Effects 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- -1 ester derivatives of CBDA Chemical class 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 230000003389 potentiating effect Effects 0.000 description 5
- 208000020925 Bipolar disease Diseases 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 208000019022 Mood disease Diseases 0.000 description 4
- 229920005372 Plexiglas® Polymers 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000003281 allosteric effect Effects 0.000 description 4
- 230000000949 anxiolytic effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 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 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 208000024714 major depressive disease Diseases 0.000 description 4
- 230000010534 mechanism of action Effects 0.000 description 4
- 210000000214 mouth Anatomy 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 229940044601 receptor agonist Drugs 0.000 description 4
- 239000000018 receptor agonist Substances 0.000 description 4
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 4
- 229940081974 saccharin Drugs 0.000 description 4
- 235000019204 saccharin Nutrition 0.000 description 4
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 208000017194 Affective disease Diseases 0.000 description 3
- 101150015707 HTR1A gene Proteins 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 3
- 208000018737 Parkinson disease Diseases 0.000 description 3
- 230000006978 adaptation Effects 0.000 description 3
- 230000001062 anti-nausea Effects 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 235000012631 food intake Nutrition 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000036407 pain Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 238000000159 protein binding assay Methods 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000001356 surgical procedure Methods 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical compound II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 102000010907 Cyclooxygenase 2 Human genes 0.000 description 2
- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 2
- 229910013470 LiC1 Inorganic materials 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 238000000692 Student's t-test Methods 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 230000003474 anti-emetic effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000002111 antiemetic agent Substances 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 229940064804 betadine Drugs 0.000 description 2
- 239000012148 binding buffer Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 210000000133 brain stem Anatomy 0.000 description 2
- PUXBGTOOZJQSKH-UHFFFAOYSA-N carprofen Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C(O)=O)C)C=C3NC2=C1 PUXBGTOOZJQSKH-UHFFFAOYSA-N 0.000 description 2
- 230000012292 cell migration Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 238000007405 data analysis Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 210000004283 incisor Anatomy 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000006742 locomotor activity Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 208000030761 polycystic kidney disease Diseases 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 238000010149 post-hoc-test Methods 0.000 description 2
- 229940099315 rimadyl Drugs 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 238000012353 t test Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
- 208000009304 Acute Kidney Injury Diseases 0.000 description 1
- 208000010392 Bone Fractures Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000008697 Cannabis sativa Nutrition 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- 102000003951 Erythropoietin Human genes 0.000 description 1
- 108090000394 Erythropoietin Proteins 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 208000032759 Hemolytic-Uremic Syndrome Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 238000012404 In vitro experiment Methods 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
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 208000006670 Multiple fractures Diseases 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000288722 Suncus murinus Species 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 210000003423 ankle Anatomy 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 230000004596 appetite loss Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000010170 biological method Methods 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003557 cannabinoid Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- IVUMCTKHWDRRMH-UHFFFAOYSA-N carprofen Chemical compound C1=CC(Cl)=C[C]2C3=CC=C(C(C(O)=O)C)C=C3N=C21 IVUMCTKHWDRRMH-UHFFFAOYSA-N 0.000 description 1
- 229960003184 carprofen Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 208000020832 chronic kidney disease Diseases 0.000 description 1
- 208000022831 chronic renal failure syndrome Diseases 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 208000033679 diabetic kidney disease Diseases 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical class OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940095399 enema Drugs 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 229940105423 erythropoietin Drugs 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000004247 hand Anatomy 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229940125425 inverse agonist Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229960002725 isoflurane Drugs 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 210000002414 leg Anatomy 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 208000012866 low blood pressure Diseases 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- CHKVEDLTACTUAS-UHFFFAOYSA-L magnesium;methyl carbonate Chemical compound [Mg+2].COC([O-])=O.COC([O-])=O CHKVEDLTACTUAS-UHFFFAOYSA-L 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 240000004308 marijuana Species 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000422 nocturnal effect Effects 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 239000002469 receptor inverse agonist Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000003362 replicative effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 210000001991 scapula Anatomy 0.000 description 1
- 239000003727 serotonin 1A antagonist Substances 0.000 description 1
- 208000013220 shortness of breath Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 230000036318 urination frequency Effects 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
-
- 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
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/16—Acetic acid esters of dihydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762522243P | 2017-06-20 | 2017-06-20 | |
| US62/522,243 | 2017-06-20 | ||
| PCT/IL2018/050678 WO2018235079A1 (en) | 2017-06-20 | 2018-06-20 | Cannabidiolic acid esters compositions and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3067512A1 true CA3067512A1 (en) | 2018-12-27 |
Family
ID=62875079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3067512A Pending CA3067512A1 (en) | 2017-06-20 | 2018-06-20 | Cannabidiolic acid esters compositions and uses thereof |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US11440870B2 (enExample) |
| EP (1) | EP3509638B1 (enExample) |
| JP (1) | JP2020524679A (enExample) |
| CN (1) | CN111032088A (enExample) |
| AU (1) | AU2018287018B2 (enExample) |
| BR (1) | BR112019026916A2 (enExample) |
| CA (1) | CA3067512A1 (enExample) |
| DK (1) | DK3509638T3 (enExample) |
| ES (1) | ES2909350T3 (enExample) |
| MX (1) | MX389847B (enExample) |
| PT (1) | PT3509638T (enExample) |
| WO (1) | WO2018235079A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10239808B1 (en) | 2016-12-07 | 2019-03-26 | Canopy Holdings, LLC | Cannabis extracts |
| CA3067512A1 (en) | 2017-06-20 | 2018-12-27 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Cannabidiolic acid esters compositions and uses thereof |
| EP3745884A1 (en) | 2018-01-31 | 2020-12-09 | Canopy Holdings, Llc | Hemp powder |
| CA3119729A1 (en) | 2018-10-10 | 2020-04-16 | Treehouse Biotech, Inc. | Synthesis of cannabigerol |
| AU2019412836A1 (en) * | 2018-12-25 | 2021-07-01 | Epm (Ip), Inc. | Cannabidiolic acid esters for cosmetic or edible compositions |
| US12403114B2 (en) * | 2019-03-12 | 2025-09-02 | Epm (Ip), Inc. | Cannabinoid acid ester compositions and uses thereof |
| EP4017485A1 (en) | 2019-08-22 | 2022-06-29 | EPM Group, Inc. | Cannabinoid acid ester compositions and uses thereof |
| WO2021137224A1 (en) * | 2020-01-01 | 2021-07-08 | Epm Group, Inc. | Cannabidiolic acid esters for treating muscular dystrophy |
| IL275108A (en) * | 2020-06-03 | 2022-01-01 | Epm Ip Inc | Abnormal acid cannabidiol (abn-cbd) derivatives and their uses |
| US20240000808A1 (en) * | 2020-11-16 | 2024-01-04 | Orcosa Inc. | Improved use of cannabinoids in the treatment of alzheimer's disease |
| US11672761B2 (en) | 2020-11-16 | 2023-06-13 | Orcosa Inc. | Rapidly infusing platform and compositions for therapeutic treatment in humans |
| WO2022137144A1 (en) * | 2020-12-24 | 2022-06-30 | Buzzelet Development And Technologies Ltd. | Compositions comprising cannabinoid acid esters |
| US20230066947A1 (en) * | 2021-08-04 | 2023-03-02 | Max Hammond | Method for the augmentation of substance abuse therapies using cannabinoid formulations |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2318468A1 (fr) * | 1975-07-17 | 1977-02-11 | Jaeger | Dispositif electronique d'enregistrement et de lecture de donnees concernant differents parametres au cours d'un cycle predetermine, fonction de l'un desdits parametres |
| US5342971A (en) | 1992-12-29 | 1994-08-30 | The Australian National University | Process for the preparation of dibenzo[b,d]pyrans |
| ES2224658T3 (es) | 1998-05-04 | 2005-03-01 | The University Of Connecticut | Nuevos canabinoides selectivos hacia el receptor cb2. |
| IL136839A (en) | 2000-06-16 | 2006-12-10 | Yissum Res Dev Co | Pharmaceutical compositions comprising cannabidiol derivatives, and processes for the preparation of same |
| JP2008502690A (ja) | 2004-06-15 | 2008-01-31 | アンドリュー シァン チェン， | リン脂質組成物ならびにその調製方法および使用方法 |
| AU2006297300B2 (en) * | 2005-09-29 | 2012-05-10 | Albany Molecular Research, Inc. | Process for production of delta-9-tetrahydrocannabinol |
| CN101384012B (zh) * | 2008-10-22 | 2012-05-23 | 华为终端有限公司 | 系统端和终端的交互媒体文档更新方法及装置 |
| DE102009019322A1 (de) | 2009-04-30 | 2010-11-11 | The Health Concept Gmbh | Verfahren zur Herstellung von Synthetischen Cannabinoiden |
| GB2478595B (en) | 2010-03-12 | 2018-04-04 | Gw Pharma Ltd | Phytocannabinoids in the treatment of glioma |
| GB2494461A (en) | 2011-09-12 | 2013-03-13 | Gw Pharma Ltd | Phytocannabinoids for use in the treatment of invasive cancers or metastases |
| GB2515312A (en) | 2013-06-19 | 2014-12-24 | Gw Pharma Ltd | The use of phytocannabinoids in the treatment of ovarian carcinoma |
| EP2842933B1 (de) | 2013-09-03 | 2015-07-29 | Symrise AG | Mischungen cannabinoider Verbindungen, deren Herstellung und Verwendung |
| CN106232570B (zh) * | 2014-04-16 | 2018-08-07 | 维瓦赛尔生物技术西班牙有限公司 | 新的大麻二酚醌衍生物 |
| GB2527590A (en) | 2014-06-27 | 2015-12-30 | Otsuka Pharma Co Ltd | Active pharmaceutical ingredient (API) comprising cannabinoids for use in the treatment of cancer |
| GB2531283A (en) | 2014-10-14 | 2016-04-20 | Gw Pharma Ltd | Use of cannabidiols in the treatment of degenerative skeletal muscle diseases |
| EP3061450A1 (de) | 2015-02-26 | 2016-08-31 | Symrise AG | Mischungen cannabinoider Verbindungen, deren Herstellung und Verwendung |
| GB2551987A (en) | 2016-07-01 | 2018-01-10 | Gw Res Ltd | Oral cannabinoid formulations |
| CN106810426B (zh) * | 2016-12-29 | 2020-05-08 | 暨明医药科技（苏州）有限公司 | 一种大麻二酚的合成方法 |
| CA3067512A1 (en) | 2017-06-20 | 2018-12-27 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Cannabidiolic acid esters compositions and uses thereof |
| WO2019234728A1 (en) | 2018-06-04 | 2019-12-12 | Al&Am Pharmachem Ltd. | Cannabinolic acid derivatives and uses thereof |
-
2018
- 2018-06-20 CA CA3067512A patent/CA3067512A1/en active Pending
- 2018-06-20 ES ES18739958T patent/ES2909350T3/es active Active
- 2018-06-20 JP JP2019570108A patent/JP2020524679A/ja active Pending
- 2018-06-20 CN CN201880041597.0A patent/CN111032088A/zh active Pending
- 2018-06-20 PT PT187399589T patent/PT3509638T/pt unknown
- 2018-06-20 MX MX2019015311A patent/MX389847B/es unknown
- 2018-06-20 WO PCT/IL2018/050678 patent/WO2018235079A1/en not_active Ceased
- 2018-06-20 AU AU2018287018A patent/AU2018287018B2/en active Active
- 2018-06-20 DK DK18739958.9T patent/DK3509638T3/da active
- 2018-06-20 EP EP18739958.9A patent/EP3509638B1/en active Active
- 2018-06-20 BR BR112019026916-9A patent/BR112019026916A2/pt not_active Application Discontinuation
- 2018-06-20 US US16/343,050 patent/US11440870B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ES2909350T3 (es) | 2022-05-06 |
| MX389847B (es) | 2025-03-20 |
| BR112019026916A2 (pt) | 2020-06-30 |
| EP3509638B1 (en) | 2022-01-12 |
| JP2020524679A (ja) | 2020-08-20 |
| EP3509638A1 (en) | 2019-07-17 |
| PT3509638T (pt) | 2022-03-02 |
| CN111032088A (zh) | 2020-04-17 |
| DK3509638T3 (da) | 2022-04-11 |
| MX2019015311A (es) | 2022-02-02 |
| US11440870B2 (en) | 2022-09-13 |
| AU2018287018B2 (en) | 2022-04-28 |
| WO2018235079A1 (en) | 2018-12-27 |
| US20200115317A1 (en) | 2020-04-16 |
| AU2018287018A1 (en) | 2020-01-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2018287018B2 (en) | Cannabidiolic acid esters compositions and uses thereof | |
| Pertwee et al. | Cannabidiolic acid methyl ester, a stable synthetic analogue of cannabidiolic acid, can produce 5‐HT1A receptor‐mediated suppression of nausea and anxiety in rats | |
| CN105517989B (zh) | 大麻素类化合物的混合物及其制备和用途 | |
| US9675579B2 (en) | Tetrahydrocannabivarin for use in the treatment of nausea and vomiting | |
| TW201026676A (en) | A method of inhibiting hepatitis C virus by combination of a 5,6-dihydro-1H-pyridin-2-one and one or more additional antiviral compounds | |
| ES2972711T3 (es) | Tratamiento de enfermedades del CNS con estimuladores de la GCs | |
| CN102274227B (zh) | 粉防己碱在制备预防和/或治疗抑郁症药物中的应用 | |
| TW201805283A (zh) | sGC刺激劑之固體形式 | |
| US20230218567A1 (en) | Compound and method for treating diseases and disorders | |
| US8492431B2 (en) | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of obesity | |
| MXPA06012564A (es) | Derivados de acido fenoxialquilcarboxilico en el tratamiento de enfermedades inflamatorias. | |
| Class et al. | Patent application title: CANNABIDIOLIC ACID ESTERS COMPOSITIONS AND USES THEREOF Inventors: Raphael Mechoulam (Jerusalem, IL) Linda Parker (Campbell River, British Columbia, CA) Roger Pertwee (Aberdeen, Scotland, GB) Aron Weller (Shoham, IL) Joseph Tam (Jerusalem, IL) Christeen Haj (Nazareth Hit, IL) Reem Smoum (Jerusalem, IL) | |
| HK40028173A (en) | Cannabidiolic acid esters compositions and uses thereof | |
| CN101016329A (zh) | 以介芬胺为原料制备环杷明的方法 | |
| CN108218814A (zh) | 靶向sirt3激动剂及其在aml治疗药物中的应用 | |
| KR20120081120A (ko) | 뉴로키닌 2 수용체 활성과 관련된 장애 또는 질환을 치료하기 위한 화합물 | |
| JP2024527932A (ja) | カンナビノイドのホスフェートプロドラッグ | |
| CN107446010A (zh) | 一种红霉素衍生物及其制备方法和应用 | |
| CN102228696B (zh) | 聚乙二醇-聚乙烯醇共聚物-美他沙酮前药及其合成方法 | |
| CN110003157A (zh) | 一种具有抗焦虑作用的新型黄酮类化合物及其应用 | |
| CN1318414C (zh) | 含邻萘醌结构的化合物及其应用 | |
| EP1940831A1 (en) | Salicylate and gentisate salts of a piperazine compound | |
| CN1690073A (zh) | 甾体类衍生物 | |
| CN102408433B (zh) | 含嘧啶的肟类化合物、其制备方法和用途 | |
| CN1736381B (zh) | 吗啉甲基萘满酮用于制备平滑肌解痉剂的用途 |