NZ523029A - (3R, 4R)-delta8-tetrahydrocannabinol-11-oic acids useful for decreasing cell proliferation - Google Patents
(3R, 4R)-delta8-tetrahydrocannabinol-11-oic acids useful for decreasing cell proliferationInfo
- Publication number
- NZ523029A NZ523029A NZ523029A NZ52302901A NZ523029A NZ 523029 A NZ523029 A NZ 523029A NZ 523029 A NZ523029 A NZ 523029A NZ 52302901 A NZ52302901 A NZ 52302901A NZ 523029 A NZ523029 A NZ 523029A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- medicament
- branched
- cell proliferation
- cells
- Prior art date
Links
- 230000004663 cell proliferation Effects 0.000 title claims abstract description 30
- 230000003247 decreasing effect Effects 0.000 title claims abstract description 12
- 239000002253 acid Substances 0.000 title description 4
- 150000007513 acids Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- -1 alkyl compound Chemical class 0.000 claims abstract description 19
- 239000003814 drug Substances 0.000 claims abstract description 19
- 241000124008 Mammalia Species 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical group 0.000 claims abstract 3
- 206010028980 Neoplasm Diseases 0.000 claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 230000037396 body weight Effects 0.000 claims description 5
- 239000007943 implant Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims 1
- 238000007910 systemic administration Methods 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 59
- YCHYFHOSGQABSW-RTBURBONSA-N (6ar,10ar)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid Chemical compound C1C(C(O)=O)=CC[C@H]2C(C)(C)OC3=CC(C(C)(C)CCCCCC)=CC(O)=C3[C@@H]21 YCHYFHOSGQABSW-RTBURBONSA-N 0.000 description 42
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 25
- 229960004242 dronabinol Drugs 0.000 description 21
- 230000000694 effects Effects 0.000 description 19
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 description 16
- 150000002632 lipids Chemical class 0.000 description 10
- 208000032612 Glial tumor Diseases 0.000 description 9
- 206010018338 Glioma Diseases 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000003557 cannabinoid Substances 0.000 description 8
- 229930003827 cannabinoid Natural products 0.000 description 8
- 102000003923 Protein Kinase C Human genes 0.000 description 7
- 108090000315 Protein Kinase C Proteins 0.000 description 7
- YOVRGSHRZRJTLZ-HZPDHXFCSA-N 11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol Chemical compound C1=C(C(O)=O)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 YOVRGSHRZRJTLZ-HZPDHXFCSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000000692 Student's t-test Methods 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 238000011534 incubation Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000001404 mediated effect Effects 0.000 description 6
- 238000012353 t test Methods 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 description 4
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 230000022131 cell cycle Effects 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000000134 MTT assay Methods 0.000 description 3
- 231100000002 MTT assay Toxicity 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 230000006907 apoptotic process Effects 0.000 description 3
- 229940065144 cannabinoids Drugs 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001982 diacylglycerols Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 229940067606 lecithin Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000035407 negative regulation of cell proliferation Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 210000002307 prostate Anatomy 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 229940114079 arachidonic acid Drugs 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 235000015872 dietary supplement Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000000684 flow cytometry Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 238000011580 nude mouse model Methods 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 229940068965 polysorbates Drugs 0.000 description 2
- 238000012809 post-inoculation Methods 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 229940124802 CB1 antagonist Drugs 0.000 description 1
- 102100033868 Cannabinoid receptor 1 Human genes 0.000 description 1
- 241000218236 Cannabis Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 238000001061 Dunnett's test Methods 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 102100028701 General vesicular transport factor p115 Human genes 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000767151 Homo sapiens General vesicular transport factor p115 Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 108010044467 Isoenzymes Proteins 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 208000023146 Pre-existing disease Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000003639 Student–Newman–Keuls (SNK) method Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 1
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000001640 apoptogenic effect Effects 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 238000001516 cell proliferation assay Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000000546 chi-square test Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000005917 in vivo anti-tumor Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- WVJKHCGMRZGIJH-UHFFFAOYSA-N methanetriamine Chemical compound NC(N)N WVJKHCGMRZGIJH-UHFFFAOYSA-N 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 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 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- IHUHXSNGMLUYES-UHFFFAOYSA-J osmium(iv) chloride Chemical compound Cl[Os](Cl)(Cl)Cl IHUHXSNGMLUYES-UHFFFAOYSA-J 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 206010040882 skin lesion Diseases 0.000 description 1
- 231100000444 skin lesion Toxicity 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 229940117972 triolein Drugs 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- 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
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20493500P | 2000-05-17 | 2000-05-17 | |
| PCT/US2001/015916 WO2001087295A1 (en) | 2000-05-17 | 2001-05-17 | Methods for decreasing cell proliferation based on (3r, 4r)-δ8-tetrahydrocannabinol-11-oic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ523029A true NZ523029A (en) | 2004-11-26 |
Family
ID=22760084
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ523029A NZ523029A (en) | 2000-05-17 | 2001-05-17 | (3R, 4R)-delta8-tetrahydrocannabinol-11-oic acids useful for decreasing cell proliferation |
| NZ523028A NZ523028A (en) | 2000-05-17 | 2001-05-17 | Cannabinoid drugs for use in decreasing cell proliferation |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ523028A NZ523028A (en) | 2000-05-17 | 2001-05-17 | Cannabinoid drugs for use in decreasing cell proliferation |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6448288B1 (enExample) |
| EP (2) | EP1307186A4 (enExample) |
| JP (2) | JP2003533479A (enExample) |
| CN (2) | CN1273123C (enExample) |
| AT (1) | ATE406156T1 (enExample) |
| AU (5) | AU6468001A (enExample) |
| CA (2) | CA2409005A1 (enExample) |
| DE (1) | DE60135557D1 (enExample) |
| HU (2) | HUP0700038A2 (enExample) |
| IL (3) | IL152892A0 (enExample) |
| NZ (2) | NZ523029A (enExample) |
| RU (2) | RU2272620C2 (enExample) |
| WO (3) | WO2001087297A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ535349A (en) | 2002-03-08 | 2007-01-26 | Signal Pharm Inc | JNK inhibitors with chemotherapeutic agents in a combination therapy for treating or preventing cancer and other proliferative disorders in refractory patients in particular |
| EP1509250B1 (en) * | 2002-06-06 | 2008-05-07 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Methods compositions and articles of manufacture for modulating bone growth |
| WO2004058251A1 (en) * | 2002-12-19 | 2004-07-15 | University Of Massachusetts | Cannabinoid analogs as peroxisome proliferator activated nuclear receptor gamma activators |
| US7169942B2 (en) * | 2003-05-20 | 2007-01-30 | University Of Tennessee Research Foundation | Cannabinoid derivatives, methods of making, and use thereof |
| US8580842B2 (en) | 2003-09-30 | 2013-11-12 | Abbott Gmbh & Co. Kg | Heteroaryl-substituted 1,3-dihydroindol-2-one derivatives and medicaments containing them |
| US20050070718A1 (en) | 2003-09-30 | 2005-03-31 | Abbott Gmbh & Co. Kg | Heteroaryl-substituted 1,3-dihydroindol-2-one derivatives and medicaments containing them |
| GB2418612A (en) * | 2004-10-01 | 2006-04-05 | Gw Pharma Ltd | Inhibition of tumour cell migration with cannabinoids |
| WO2006065793A2 (en) * | 2004-12-13 | 2006-06-22 | Indevus Pharmaceuticals, Inc. | TREATMENT OF INTERSTITIAL CYSTITIS USING (6aR,10aR)-Δ8-TETRAHYDROCANNABINOL-11-OIC ACIDS |
| WO2006065792A2 (en) * | 2004-12-13 | 2006-06-22 | Indevus Pharmaceuticals, Inc. | Treatment of interstitial cystitis using cannabinoid analogs |
| US20070037873A1 (en) * | 2005-08-08 | 2007-02-15 | Zurier Robert B | Airway remodeling treatments |
| US7597910B2 (en) * | 2005-08-20 | 2009-10-06 | Slgm Medical Research Institute | Compositions and methods for treating prostate disorders |
| EP2578561A1 (en) * | 2005-09-29 | 2013-04-10 | Albany Molecular Research, Inc. | Processes for the production of cannabidiol derivatives and intermediates thereof |
| US20070093519A1 (en) * | 2005-10-20 | 2007-04-26 | Indevus Pharmaceuticals, Inc. | Anti-emetic uses of cannabinoid analogs |
| US20070099988A1 (en) * | 2005-10-31 | 2007-05-03 | Indevus Pharmaceuticals, Inc. | Anti-emetic uses of (3r, 4r)-delta8-tetrahydrocannabinol-11-oic acids |
| US20080167286A1 (en) | 2006-12-12 | 2008-07-10 | Abbott Laboratories | Pharmaceutical compositions and their methods of use |
| US8486979B2 (en) | 2006-12-12 | 2013-07-16 | Abbvie Inc. | 1,2,4 oxadiazole compounds and methods of use thereof |
| UY30846A1 (es) | 2006-12-30 | 2008-07-31 | Abbott Gmbh & Amp | Derivados de oxindol sustituidos, medicamentos que los comprenden y uso de los mismos |
| US7781650B2 (en) * | 2007-04-30 | 2010-08-24 | Monsanto Technology Llc | Plants and seeds of corn variety CV202909 |
| WO2008144475A1 (en) | 2007-05-17 | 2008-11-27 | California Pacific Medical Center | Methods and compositions for treating cancer |
| US8703774B2 (en) | 2007-12-07 | 2014-04-22 | AbbVie Deutschland GmbH & Co. KG | Carbamate-substituted oxindole derivatives and use thereof for the treatment of vasopressin-dependent diseases |
| ES2398676T3 (es) | 2007-12-07 | 2013-03-20 | Abbott Gmbh & Co. Kg | Derivados de oxindol sustituidos con amidometilo y su uso para la producción de un medicamento para el tratamiento de enfermedades dependientes de la vasopresina |
| EP2231644B1 (de) | 2007-12-07 | 2014-01-15 | AbbVie Deutschland GmbH & Co KG | 5,6-Disubstitutierte Oxindol-Derivate und ihre Verwendung zur Herstellung eines Medikaments zur Behandlung von Vasopressin-abhängigen Erkrankungen |
| NZ586651A (en) | 2007-12-07 | 2012-06-29 | Abbott Gmbh & Co Kg | 5-halogen-substituted oxindole derivatives and use thereof for treating vasopressine-dependent diseases |
| GB2471987B (en) | 2008-06-04 | 2012-02-22 | Gw Pharma Ltd | Anti-tumoural effects of cannabinoid combinations |
| US9040568B2 (en) | 2009-05-29 | 2015-05-26 | Abbvie Inc. | Pharmaceutical compositions for the treatment of pain |
| GB2478595B (en) | 2010-03-12 | 2018-04-04 | Gw Pharma Ltd | Phytocannabinoids in the treatment of glioma |
| GB2487712B (en) | 2011-01-04 | 2015-10-28 | Otsuka Pharma Co Ltd | Use of the phytocannabinoid cannabidiol (CBD) in combination with a standard anti-epileptic drug (SAED) in the treatment of epilepsy |
| GB2495118B (en) | 2011-09-29 | 2016-05-18 | Otsuka Pharma Co Ltd | A pharmaceutical composition comprising the phytocannabinoids cannabidivarin (CBDV) and cannabidiol (CBD) |
| GB2516814B (en) | 2013-06-19 | 2016-08-31 | Otsuka Pharma Co Ltd | Use of phytocannabinoids for increasing radiosensitivity in the treatment of cancer |
| AU2018311965A1 (en) | 2017-08-04 | 2020-02-13 | Merck Sharp & Dohme Llc | Combinations of PD-1 antagonists and benzo[b]thiophene sting antagonists for cancer treatment |
| MA49772A (fr) | 2017-08-04 | 2021-04-21 | Merck Sharp & Dohme | Agonistes benzo[b]thiophène de sting pour le traitement du cancer |
| CN111233814A (zh) * | 2020-03-02 | 2020-06-05 | 福建省中科生物股份有限公司 | 一种萜酚类化合物zkyy-057及其制备方法和应用 |
| US12029718B2 (en) | 2021-11-09 | 2024-07-09 | Cct Sciences, Llc | Process for production of essentially pure delta-9-tetrahydrocannabinol |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5A (en) * | 1836-08-10 | Thomas Blanchard | Machine for mortising solid wooden shells of ships' tackle-blocks | |
| US4327028A (en) * | 1978-08-17 | 1982-04-27 | Calcol, Inc. | Composition of matter |
| ZA885929B (en) * | 1987-08-25 | 1989-04-26 | Oxi Gene Inc | Agents for use in tumor or cancer cell killing therapy |
| US4973603A (en) * | 1988-06-16 | 1990-11-27 | Sumner Burstein | Platelet activating factor antagonist and methods of use therefor |
| US4880030A (en) * | 1988-07-25 | 1989-11-14 | Terry Paul E | Safety flow control fluid shutoff device |
| US5538993A (en) * | 1991-09-12 | 1996-07-23 | Yissum Research Development Company | Certain tetrahydrocannabinol-7-oic acid derivatives |
| US5635530A (en) * | 1991-09-12 | 1997-06-03 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | (3S,4S)-delta-6-tetrahydrocannabinol-7-oic acids and derivatives thereof, processors for their preparation and pharmaceutical compositions containing them |
| US5338753A (en) | 1992-07-14 | 1994-08-16 | Sumner H. Burstein | (3R,4R)-Δ6 -tetrahydrocannabinol-7-oic acids useful as antiinflammatory agents and analgesics |
| US6162829A (en) * | 1997-10-17 | 2000-12-19 | Atlantic Pharmaceuticals, Inc. | (3R,4R)-Δ8 -tetrahydrocannabinol-11-oic acids useful as antiinflammatory agents and analgesics |
| ES1045342Y (es) * | 2000-02-11 | 2001-02-16 | Alvarez Manuel Couto | Expositor giratorio para postales, fotos y similares. |
-
2001
- 2001-05-08 US US09/851,122 patent/US6448288B1/en not_active Expired - Lifetime
- 2001-05-17 HU HU0700038A patent/HUP0700038A2/hu unknown
- 2001-05-17 DE DE60135557T patent/DE60135557D1/de not_active Expired - Fee Related
- 2001-05-17 CN CNB018130100A patent/CN1273123C/zh not_active Expired - Fee Related
- 2001-05-17 HU HU0700039A patent/HUP0700039A2/hu unknown
- 2001-05-17 CA CA002409005A patent/CA2409005A1/en not_active Abandoned
- 2001-05-17 NZ NZ523029A patent/NZ523029A/en unknown
- 2001-05-17 CA CA002408961A patent/CA2408961A1/en not_active Abandoned
- 2001-05-17 RU RU2002133869/14A patent/RU2272620C2/ru not_active IP Right Cessation
- 2001-05-17 AU AU6468001A patent/AU6468001A/xx active Pending
- 2001-05-17 RU RU2002133868/15A patent/RU2273476C2/ru not_active IP Right Cessation
- 2001-05-17 EP EP01935616A patent/EP1307186A4/en not_active Withdrawn
- 2001-05-17 EP EP01939128A patent/EP1307188B1/en not_active Expired - Lifetime
- 2001-05-17 AU AU2001263217A patent/AU2001263217A1/en not_active Abandoned
- 2001-05-17 AT AT01939128T patent/ATE406156T1/de not_active IP Right Cessation
- 2001-05-17 US US10/276,819 patent/US6914072B2/en not_active Expired - Fee Related
- 2001-05-17 WO PCT/US2001/016150 patent/WO2001087297A1/en not_active Ceased
- 2001-05-17 WO PCT/US2001/015927 patent/WO2001087296A1/en not_active Ceased
- 2001-05-17 IL IL15289201A patent/IL152892A0/xx unknown
- 2001-05-17 AU AU6169501A patent/AU6169501A/xx active Pending
- 2001-05-17 AU AU2001261695A patent/AU2001261695B2/en not_active Ceased
- 2001-05-17 NZ NZ523028A patent/NZ523028A/en unknown
- 2001-05-17 JP JP2001583765A patent/JP2003533479A/ja active Pending
- 2001-05-17 JP JP2001583763A patent/JP2003533478A/ja active Pending
- 2001-05-17 CN CNB018129161A patent/CN1227007C/zh not_active Expired - Fee Related
- 2001-05-17 WO PCT/US2001/015916 patent/WO2001087295A1/en not_active Ceased
- 2001-05-17 AU AU2001264680A patent/AU2001264680B2/en not_active Ceased
- 2001-05-17 IL IL15289101A patent/IL152891A0/xx unknown
-
2002
- 2002-11-17 IL IL152892A patent/IL152892A/en not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2001261695B2 (en) | Methods for decreasing cell proliferation based on (3r, 4r)-delta8-tetrahydrocannabinol-11-oic acids | |
| AU2001261695A1 (en) | Methods for decreasing cell proliferation based on (3R, 4R)-delta8-tetrahydrocannabinol-11-oic acids | |
| AU2001264680A1 (en) | Cannabinoid drugs | |
| Wang et al. | Cytotoxic effects of cantharidin on the growth of normal and carcinoma cells | |
| Hsu et al. | Clinical studies with curcumin | |
| JPS6038324A (ja) | 脂肪酸組成物 | |
| US4910224A (en) | Method of modifying the lipid structure and function of cell membranes and pharmaceutical compositions for use therein | |
| MX2007001356A (es) | Portador para administracion enterica. | |
| Guo et al. | BaoShenTongLuo formula protects against podocyte injury by regulating AMPK-mediated mitochondrial biogenesis in diabetic kidney disease | |
| US6562864B1 (en) | Catechin multimers as therapeutic drug delivery agents | |
| US6974835B2 (en) | Methods for decreasing cell proliferation based on (3r,4r)-Δ8-tetrahydrocannabinol-11-oic acids | |
| CA2611860A1 (en) | Compositions and methods of use of derivatized flavanols | |
| NL2022615B1 (en) | Pharmaceutical composition comprising tetrahydrocannabivarin for the prevention and treatment of overweight | |
| KR102836097B1 (ko) | 비알코올성 지방간 질환의 예방 또는 치료용 조성물 | |
| CN101076354B (zh) | 用于肠道给药的载体 | |
| AU2005220236B2 (en) | Carrier for enteral administration | |
| WO1993009773A1 (fr) | Composition servant a prevenir ou a traiter la dysmenorrhee et aliment ayant une fonction de prevention de la dysmenorrhee | |
| JP2013166734A (ja) | アルコール摂取に起因する海馬神経活動の低下の抑制剤 | |
| ITRM20060203A1 (it) | Composizione a base di preparazioni estrattive di piante officinali e edule per il trattamento delle dislipidemie |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ASS | Change of ownership |
Owner name: INDEVUS PHARMACEUTICALS, INC., US Free format text: OLD OWNER(S): MANHATTAN PHARMACEUTICALS, INC. |
|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) |