CA2435409A1 - Novel cannabimimetic ligands - Google Patents
Novel cannabimimetic ligands Download PDFInfo
- Publication number
- CA2435409A1 CA2435409A1 CA002435409A CA2435409A CA2435409A1 CA 2435409 A1 CA2435409 A1 CA 2435409A1 CA 002435409 A CA002435409 A CA 002435409A CA 2435409 A CA2435409 A CA 2435409A CA 2435409 A1 CA2435409 A1 CA 2435409A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- reversed
- enantiomer
- lower alkyl
- amino
- 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.)
- Abandoned
Links
- 230000003375 cannabimimetic effect Effects 0.000 title claims description 25
- 239000003446 ligand Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 124
- 238000000034 method Methods 0.000 claims abstract description 31
- 241001465754 Metazoa Species 0.000 claims abstract description 18
- 229930003827 cannabinoid Natural products 0.000 claims abstract description 16
- 239000003557 cannabinoid Substances 0.000 claims abstract description 16
- 102000018208 Cannabinoid Receptor Human genes 0.000 claims abstract description 9
- 108050007331 Cannabinoid receptor Proteins 0.000 claims abstract description 9
- 230000001766 physiological effect Effects 0.000 claims abstract description 3
- -1 diasteromers Chemical class 0.000 claims description 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 150000007970 thio esters Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 24
- 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 claims description 19
- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 150000001408 amides Chemical class 0.000 claims description 14
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 150000003505 terpenes Chemical class 0.000 claims description 9
- 235000007586 terpenes Nutrition 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 230000002093 peripheral effect Effects 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 208000002193 Pain Diseases 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 208000010412 Glaucoma Diseases 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 206010028813 Nausea Diseases 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 238000002512 chemotherapy Methods 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 230000035558 fertility Effects 0.000 claims description 2
- 210000000987 immune system Anatomy 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 230000007659 motor function Effects 0.000 claims description 2
- 230000008693 nausea Effects 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 230000004112 neuroprotection Effects 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 18
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 6
- 229910006069 SO3H Inorganic materials 0.000 claims 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 6
- 150000004905 tetrazines Chemical class 0.000 claims 3
- 230000004936 stimulating effect Effects 0.000 claims 2
- 229940065144 cannabinoids Drugs 0.000 abstract description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 101150041968 CDC13 gene Proteins 0.000 description 50
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000007787 solid Substances 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 229910052799 carbon Inorganic materials 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 14
- 230000027455 binding Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 238000007792 addition Methods 0.000 description 8
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 8
- 239000003480 eluent Substances 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 102000005962 receptors Human genes 0.000 description 7
- 108020003175 receptors Proteins 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 description 6
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 102100036214 Cannabinoid receptor 2 Human genes 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 102100033868 Cannabinoid receptor 1 Human genes 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 230000006461 physiological response Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000159 protein binding assay Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 3
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-Chlorosuccinimide Substances ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 229940098773 bovine serum albumin Drugs 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229940095074 cyclic amp Drugs 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000007918 intramuscular administration Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- BSXWVZKFHYNKAC-UHFFFAOYSA-N 2-(phenylhydrazinylidene)butanoic acid Chemical compound CCC(C(O)=O)=NNC1=CC=CC=C1 BSXWVZKFHYNKAC-UHFFFAOYSA-N 0.000 description 2
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical class C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 2
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- BKMMTJMQCTUHRP-GSVOUGTGSA-N (2r)-2-aminopropan-1-ol Chemical compound C[C@@H](N)CO BKMMTJMQCTUHRP-GSVOUGTGSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- LCTNHLOBILHMQJ-VURMDHGXSA-N (Z)-3-anilino-2-chloroprop-2-enoic acid Chemical compound OC(=O)C(\Cl)=C\NC1=CC=CC=C1 LCTNHLOBILHMQJ-VURMDHGXSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QENIALCDPFDFHX-UHFFFAOYSA-N 1,4-dibromo-2,5-dimethylbenzene Chemical group CC1=CC(Br)=C(C)C=C1Br QENIALCDPFDFHX-UHFFFAOYSA-N 0.000 description 1
- TUSIRMATSRRTEJ-UHFFFAOYSA-N 1,4-dimethyl-2,5-diphenylbenzene Chemical compound CC1=CC(C=2C=CC=CC=2)=C(C)C=C1C1=CC=CC=C1 TUSIRMATSRRTEJ-UHFFFAOYSA-N 0.000 description 1
- BGCICGVSAJPIFP-UHFFFAOYSA-N 1-[6-acetyl-1,4-bis(4-chlorophenyl)-1,2,4,5-tetrazin-3-yl]ethanone Chemical compound CC(=O)C1=NN(C=2C=CC(Cl)=CC=2)C(C(C)=O)=NN1C1=CC=C(Cl)C=C1 BGCICGVSAJPIFP-UHFFFAOYSA-N 0.000 description 1
- QSRJJVRCMOCMSO-UHFFFAOYSA-N 1-bromo-2,5-dimethyl-4-phenylbenzene Chemical compound C1=C(Br)C(C)=CC(C=2C=CC=CC=2)=C1C QSRJJVRCMOCMSO-UHFFFAOYSA-N 0.000 description 1
- ASAQRGCLIPUSEK-UHFFFAOYSA-N 2-[4-amino-n-(2-hydroxyethyl)-3-nitroanilino]ethanol;hydrochloride Chemical compound Cl.NC1=CC=C(N(CCO)CCO)C=C1[N+]([O-])=O ASAQRGCLIPUSEK-UHFFFAOYSA-N 0.000 description 1
- BPVPAMLOUGSZLY-UHFFFAOYSA-N 2-chloro-2-ethoxyacetic acid Chemical compound CCOC(Cl)C(O)=O BPVPAMLOUGSZLY-UHFFFAOYSA-N 0.000 description 1
- MVIVDSWUOGNODP-UHFFFAOYSA-N 2-iodobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1I MVIVDSWUOGNODP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- YPUJSWNMRARBKX-UHFFFAOYSA-N 3-n,3-n-dibutyl-1,4-diphenyl-1,2,4,5-tetrazine-3,6-dicarboxamide Chemical compound CCCCN(CCCC)C(=O)C1=NN(C=2C=CC=CC=2)C(C(N)=O)=NN1C1=CC=CC=C1 YPUJSWNMRARBKX-UHFFFAOYSA-N 0.000 description 1
- FSXMDCNFQJOCHM-UHFFFAOYSA-N 3-n,3-n-diethyl-1,4-diphenyl-1,2,4,5-tetrazine-3,6-dicarboxamide Chemical compound CCN(CC)C(=O)C1=NN(C=2C=CC=CC=2)C(C(N)=O)=NN1C1=CC=CC=C1 FSXMDCNFQJOCHM-UHFFFAOYSA-N 0.000 description 1
- MSPRIOYHVIICHU-UHFFFAOYSA-N 3-n,3-n-dimethyl-1,4-diphenyl-1,2,4,5-tetrazine-3,6-dicarboxamide Chemical compound CN(C)C(=O)C1=NN(C=2C=CC=CC=2)C(C(N)=O)=NN1C1=CC=CC=C1 MSPRIOYHVIICHU-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- ICVMUXNBUWOYOO-UHFFFAOYSA-N C(C)NC(=O)C1=NN(C(=NN1C1=CC=CC=C1)C(=O)N)C1=CC=CC=C1 Chemical compound C(C)NC(=O)C1=NN(C(=NN1C1=CC=CC=C1)C(=O)N)C1=CC=CC=C1 ICVMUXNBUWOYOO-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 108091006027 G proteins Proteins 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- 208000032612 Glial tumor Diseases 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 102000016979 Other receptors Human genes 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 208000000323 Tourette Syndrome Diseases 0.000 description 1
- 208000016620 Tourette disease Diseases 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical group N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 1
- AQZZSWZMWUUVCI-UHFFFAOYSA-M benzenediazonium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.N#[N+]C1=CC=CC=C1 AQZZSWZMWUUVCI-UHFFFAOYSA-M 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000012502 diagnostic product Substances 0.000 description 1
- FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 1
- SDRDGLVIKISGHS-UHFFFAOYSA-N diethyl 1,2,4,5-tetrazine-3,6-dicarboxylate Chemical compound CCOC(=O)C1=NN=C(C(=O)OCC)N=N1 SDRDGLVIKISGHS-UHFFFAOYSA-N 0.000 description 1
- XBSIFSHIAODQKJ-UHFFFAOYSA-N diethyl 1,4-bis(2-iodobenzoyl)-1,2,4,5-tetrazine-3,6-dicarboxylate Chemical compound CCOC(=O)C1=NN(C(=O)C=2C(=CC=CC=2)I)C(C(=O)OCC)=NN1C(=O)C1=CC=CC=C1I XBSIFSHIAODQKJ-UHFFFAOYSA-N 0.000 description 1
- VYDKNBHPRJIBBI-UHFFFAOYSA-N diethyl 1,4-bis(4-chlorophenyl)-1,2,4,5-tetrazine-3,6-dicarboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC(Cl)=CC=2)C(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1 VYDKNBHPRJIBBI-UHFFFAOYSA-N 0.000 description 1
- ICEMIGGWJGDPLJ-UHFFFAOYSA-N diethyl 1,4-dibenzoyl-1,2,4,5-tetrazine-3,6-dicarboxylate Chemical compound CCOC(=O)C1=NN(C(=O)C=2C=CC=CC=2)C(C(=O)OCC)=NN1C(=O)C1=CC=CC=C1 ICEMIGGWJGDPLJ-UHFFFAOYSA-N 0.000 description 1
- VIILKELRUOLCFW-UHFFFAOYSA-N diethyl 1-(4-chlorophenyl)-4-phenyl-1,2,4,5-tetrazine-3,6-dicarboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC(Cl)=CC=2)C(C(=O)OCC)=NN1C1=CC=CC=C1 VIILKELRUOLCFW-UHFFFAOYSA-N 0.000 description 1
- RDLVNTIPWHWPDA-UHFFFAOYSA-N diethyl 2,5-diphenylbenzene-1,4-dicarboxylate Chemical compound CCOC(=O)C=1C=C(C=2C=CC=CC=2)C(C(=O)OCC)=CC=1C1=CC=CC=C1 RDLVNTIPWHWPDA-UHFFFAOYSA-N 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- PWOKQLDDJBLSTB-UHFFFAOYSA-N diethyl 2-benzoyl-1h-1,2,4,5-tetrazine-3,6-dicarboxylate Chemical compound CCOC(=O)C1=NNC(C(=O)OCC)=NN1C(=O)C1=CC=CC=C1 PWOKQLDDJBLSTB-UHFFFAOYSA-N 0.000 description 1
- VJUDCVXATVJENN-UHFFFAOYSA-N diethyl 5h-pyridazino[4,5-b]indole-1,4-dicarboxylate Chemical compound C12=CC=CC=C2NC2=C1C(C(=O)OCC)=NN=C2C(=O)OCC VJUDCVXATVJENN-UHFFFAOYSA-N 0.000 description 1
- SKMKNDXGPMOFKH-UHFFFAOYSA-N dimethyl 1,4-diphenyl-1,2,4,5-tetrazine-3,6-dicarboxylate Chemical compound COC(=O)C1=NN(C=2C=CC=CC=2)C(C(=O)OC)=NN1C1=CC=CC=C1 SKMKNDXGPMOFKH-UHFFFAOYSA-N 0.000 description 1
- UFXOGAQWYLAYJF-UHFFFAOYSA-N dipropyl 1,4-diphenyl-1,2,4,5-tetrazine-3,6-dicarboxylate Chemical compound CCCOC(=O)C1=NN(C=2C=CC=CC=2)C(C(=O)OCCC)=NN1C1=CC=CC=C1 UFXOGAQWYLAYJF-UHFFFAOYSA-N 0.000 description 1
- 229960004242 dronabinol Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- XCLBIKIQSCTANZ-UHFFFAOYSA-N ethyl 2,2-diethoxyacetate Chemical compound CCOC(OCC)C(=O)OCC XCLBIKIQSCTANZ-UHFFFAOYSA-N 0.000 description 1
- HBFODCHBGMCCCF-UHFFFAOYSA-N ethyl 5-oxo-2-phenyl-1,2-oxazole-4-carboxylate Chemical compound O1C(=O)C(C(=O)OCC)=CN1C1=CC=CC=C1 HBFODCHBGMCCCF-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 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 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 210000005171 mammalian brain Anatomy 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- PRKBLPLUZTXQLN-UHFFFAOYSA-L naphthalene-1-diazonium;sulfate Chemical compound [O-]S([O-])(=O)=O.C1=CC=C2C([N+]#N)=CC=CC2=C1.C1=CC=C2C([N+]#N)=CC=CC2=C1 PRKBLPLUZTXQLN-UHFFFAOYSA-L 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 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 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 1
- 239000007856 photoaffinity label Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 229940124606 potential therapeutic agent Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000004129 prosencephalon Anatomy 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 210000003568 synaptosome Anatomy 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/08—Six-membered 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Reproductive Health (AREA)
- Immunology (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Hospice & Palliative Care (AREA)
- Ophthalmology & Optometry (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Pregnancy & Childbirth (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26438501P | 2001-01-26 | 2001-01-26 | |
| US60/264,385 | 2001-01-26 | ||
| PCT/US2002/002157 WO2002058636A2 (en) | 2001-01-26 | 2002-01-25 | Novel cannabimimetic ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2435409A1 true CA2435409A1 (en) | 2002-08-01 |
Family
ID=23005829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002435409A Abandoned CA2435409A1 (en) | 2001-01-26 | 2002-01-25 | Novel cannabimimetic ligands |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7329651B2 (enExample) |
| EP (1) | EP1361876A4 (enExample) |
| JP (1) | JP2004532185A (enExample) |
| CA (1) | CA2435409A1 (enExample) |
| WO (1) | WO2002058636A2 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2340445A1 (en) | 1998-05-04 | 1999-11-11 | The University Of Connecticut | Novel analgesic and immunomodulatory cannabinoids |
| US7589220B2 (en) * | 1998-06-09 | 2009-09-15 | University Of Connecticut | Inhibitors of the anandamide transporter |
| US7161016B1 (en) | 1998-11-24 | 2007-01-09 | University Of Connecticut | Cannabimimetic lipid amides as useful medications |
| US7276613B1 (en) | 1998-11-24 | 2007-10-02 | University Of Connecticut | Retro-anandamides, high affinity and stability cannabinoid receptor ligands |
| US6900236B1 (en) | 1999-10-18 | 2005-05-31 | University Of Connecticut | Cannabimimetic indole derivatives |
| US7119108B1 (en) | 1999-10-18 | 2006-10-10 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US8084467B2 (en) * | 1999-10-18 | 2011-12-27 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US7393842B2 (en) * | 2001-08-31 | 2008-07-01 | University Of Connecticut | Pyrazole analogs acting on cannabinoid receptors |
| US7741365B2 (en) * | 1999-10-18 | 2010-06-22 | University Of Connecticut | Peripheral cannabinoid receptor (CB2) selective ligands |
| US6943266B1 (en) | 1999-10-18 | 2005-09-13 | University Of Connecticut | Bicyclic cannabinoid agonists for the cannabinoid receptor |
| WO2001028329A1 (en) | 1999-10-18 | 2001-04-26 | University Of Connecticut | Peripheral cannabinoid receptor (cb2) selective ligands |
| WO2002060447A1 (en) | 2001-01-29 | 2002-08-08 | University Of Connecticut | Receptor selective cannabimimetic aminoalkylindoles |
| WO2003005960A2 (en) * | 2001-07-13 | 2003-01-23 | University Of Connecticut | Novel bicyclic and tricyclic cannabinoids |
| WO2003035005A2 (en) * | 2001-10-26 | 2003-05-01 | University Of Connecticut | Heteroindanes: a new class of potent cannabimimetic ligands |
| 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 |
| EP1542657B8 (en) * | 2002-08-14 | 2012-03-14 | GW Pharma Limited | Cannabinoid liquid formulations for mucosal amdinistration |
| AU2003265663A1 (en) | 2002-08-23 | 2004-03-11 | University Of Connecticut | Keto cannabinoids with therapeutic indications |
| WO2005123053A2 (en) * | 2004-06-22 | 2005-12-29 | Pharmos Limited | Use of cb2 receptors agonists for the treatment of huntington’s disease |
| EP2131655B1 (en) * | 2007-03-02 | 2014-05-07 | The University of Tennessee Research Foundation | Tri-aryl/heteroaromatic cannabinoids and use thereof |
| CN104098524B (zh) * | 2014-05-12 | 2016-01-20 | 浙江工业大学 | 1-间甲氧基苯甲酰基-3-苯基-1,4-二氢-1,2,4,5-四嗪及制备和应用 |
| CN104098523B (zh) * | 2014-05-12 | 2016-05-18 | 浙江工业大学 | 1-异丁酰基-3-苯基-1,4-二氢-1,2,4,5-四嗪及制备和应用 |
| CN105949139B (zh) * | 2016-05-06 | 2018-01-16 | 浙江工业大学 | 一种仲丁基二苯基四嗪甲酰胺化合物及制备和应用 |
Family Cites Families (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3041343A (en) | 1959-10-14 | 1962-06-26 | Sandoz Ltd | 4-(thienyl-2'')-and 4-(pyridyl-3'')-5-aminopyrazoles |
| US3465024A (en) | 1966-11-14 | 1969-09-02 | Allied Chem | Process for the preparation of isocyanates |
| US3577458A (en) | 1966-11-14 | 1971-05-04 | Allied Chem | Process for the preparation of isocyanates |
| US3573327A (en) | 1970-03-23 | 1971-03-30 | Searle & Co | 3-(lower alkoxy)-7,8,9,10-tetrahydro-6h-dibenzo-(b,d) pyran-6,9-diones and derivatives thereof |
| US3656906A (en) | 1970-04-13 | 1972-04-18 | Little Inc A | Method for detecting and quantitating the presence of cannabinoids and analogs thereof in biological materials and resulting products |
| US3838131A (en) | 1972-04-03 | 1974-09-24 | Pfizer | Di(dialkylamino alkoxy)phenanthridines as antiviral agents |
| US3915996A (en) | 1972-10-16 | 1975-10-28 | Abbott Lab | Process for making benzopyrans |
| GB1436771A (en) | 1973-02-16 | 1976-05-26 | Labaz | Indole derivatives and process for preparing the same |
| DE2335136A1 (de) | 1973-07-06 | 1975-01-16 | Schering Ag | 7-hydroxy-delta hoch 8-tetrahydrocannabinole |
| US3886184A (en) | 1973-08-03 | 1975-05-27 | Lilly Co Eli | Aminodibenzo(b,d)pyrans |
| US4278603A (en) | 1973-11-05 | 1981-07-14 | Eli Lilly And Company | Novel polymorphic crystalline form of dibenzopyranone |
| US3928598A (en) | 1973-11-05 | 1975-12-23 | Lilly Co Eli | Hexahydro-dibenzo{8 b,d{9 pyran-9-ones as an anti-anxiety drug |
| US3953603A (en) | 1973-11-05 | 1976-04-27 | Eli Lilly And Company | Hexahydro-dibenzo[b,d,]pyran-9-ones as psychotropic, particularly anti-depressant drugs |
| US3944673A (en) | 1973-11-05 | 1976-03-16 | Eli Lilly And Company | Hexahydro-dibenzo[b,d]pyran-9-ones as analgesic drugs |
| IL48824A (en) | 1976-01-12 | 1980-05-30 | Yissum Res Dev Co | Pharmaceutical compositions containing (3s,js) tetrahydrocanabinol derivatives and some novel compounds of this type |
| US4036857A (en) | 1976-02-02 | 1977-07-19 | Sharps Associates | Benzopyrans having an unsaturated side chain |
| US4088777A (en) | 1976-02-17 | 1978-05-09 | Eli Lilly And Company | Hexahydro-dibenzo[b,d]pyran-9-ones as anticonvulsant drugs |
| US4087547A (en) | 1976-02-17 | 1978-05-02 | Eli Lilly And Company | Hexahydro-dibenzo[b,d]pyran-9-ones in treatment of glaucoma |
| US4087545A (en) | 1976-02-17 | 1978-05-02 | Eli Lilly And Company | Hexahydro-dibenzo[b,d]pyran-9-ones as antiemetic drugs |
| US4087546A (en) | 1976-02-17 | 1978-05-02 | Eli Lilly And Company | Hexahydro-dibenzo[b,d]pyran-9-ones as antiasthmatic drugs |
| US4054582A (en) | 1976-07-06 | 1977-10-18 | Eli Lilly And Company | Process for converting cis-hexahydrodibenzo[b,d]pyran-9-ones to trans-hexahydrodibenzo[b,d]-pyran-9-ones |
| US4176233A (en) | 1976-11-10 | 1979-11-27 | Eli Lilly And Company | Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor |
| US4208351A (en) | 1976-11-10 | 1980-06-17 | Eli Lilly And Company | Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor |
| US4102902A (en) | 1976-11-10 | 1978-07-25 | Eli Lilly And Company | Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor |
| US4188495A (en) | 1977-11-14 | 1980-02-12 | Pfizer Inc. | 1,9-Dihydroxyoctahydrophenanthrenes and intermediates therefor |
| US4152450A (en) | 1978-02-17 | 1979-05-01 | Eli Lilly And Company | 9-Amino-dibenzopyrans |
| US4171315A (en) | 1978-03-31 | 1979-10-16 | Eli Lilly And Company | Preparation of cis-hexahydrodibenzopyranones |
| IL55274A (en) | 1978-08-02 | 1982-08-31 | Yissum Res Dev Co | 4-(2,6-dihydroxy-4-(dimethylheptyl)phenyl)substituted 2-pinen-10-ol and pinane derivatives,their preparation and pharmaceutical compositions comprising them |
| DE3025385A1 (de) | 1980-07-04 | 1982-01-28 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue tricyclische arylether, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
| JPS5798228U (enExample) | 1980-12-10 | 1982-06-16 | ||
| US4550214A (en) | 1981-01-05 | 1985-10-29 | Polaroid Corporation | Blocked vinyl biphenyl compounds |
| US4395560A (en) | 1982-05-24 | 1983-07-26 | Eli Lilly And Company | Preparation of 6a,10a-trans-hexahydrodibenzopyranones |
| US4497827A (en) | 1982-08-30 | 1985-02-05 | Syntex (U.S.A.) Inc. | Arachidonic acid analogues as anti-inflammatory and anti-allergic agents |
| US4885295A (en) | 1984-08-06 | 1989-12-05 | Sterling Drug Inc. | Method of use of 3-arylcarbonyl- and 3-cycloalkyl-carbonyl-1-aminoalkyl-1H-indoles |
| JPS61126069A (ja) | 1984-11-21 | 1986-06-13 | Res Dev Corp Of Japan | プロスタグランジン誘導体 |
| IL80411A (en) | 1986-10-24 | 1991-08-16 | Raphael Mechoulam | Preparation of dibenzopyranol derivatives and pharmaceutical compositions containing them |
| US4833073A (en) | 1987-01-27 | 1989-05-23 | Hoffmann-La Roche Inc. | Immunoassay for tetrahydrocannabinol metabolites |
| US4758597A (en) | 1987-05-15 | 1988-07-19 | University Patents, Inc. | Carenadiol and derivatives |
| HU206337B (en) * | 1988-12-29 | 1992-10-28 | Mitsui Petrochemical Ind | Process for producing pyrimidine derivatives and pharmaceutical compositions |
| CN1029227C (zh) | 1989-02-08 | 1995-07-05 | 大制药株式会社 | 苯衍生物的制备方法 |
| US5284867A (en) | 1989-11-07 | 1994-02-08 | Yissum Research Development Company Of The Hebrew University In Jerusalem | NMDA-blocking pharmaceutical compositions |
| US5521215A (en) | 1989-11-07 | 1996-05-28 | Ramot University Authority For Applied Research And Industrial Development Ltd. | NMDA-blocking pharmaceuticals |
| US5068234A (en) | 1990-02-26 | 1991-11-26 | Sterling Drug Inc. | 3-arylcarbonyl-1-(c-attached-n-heteryl)-1h-indoles |
| FR2665444B1 (fr) | 1990-08-06 | 1992-11-27 | Sanofi Sa | Derives d'amino-benzofuranne, benzothiophene ou indole, leur procede de preparation ainsi que les compositions les contenant. |
| US6096740A (en) | 1990-11-06 | 2000-08-01 | Ramot University Authority For Applied Research And Industrial Development Ltd. | Dexanabinol derivatives and their use as neuroprotective pharmaceutical compositions |
| US5576436A (en) | 1991-08-01 | 1996-11-19 | Pharmaceutical Discovery Corporation | Fluorescent ligands |
| 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 |
| US5538993A (en) | 1991-09-12 | 1996-07-23 | Yissum Research Development Company | Certain tetrahydrocannabinol-7-oic acid derivatives |
| FR2692575B1 (fr) | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| US5489580A (en) | 1992-11-05 | 1996-02-06 | University Of Connecticut | Phospholipid compounds and use therefor |
| IL103932A (en) | 1992-11-30 | 1997-02-18 | Yissum Res & Dev | Fatty acid and pharmaceutical compositions containing them |
| US5618955A (en) | 1992-11-30 | 1997-04-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Fatty acid derivatives and pharmaceutical compositions containing same |
| US5440052A (en) | 1993-08-06 | 1995-08-08 | University Of Connecticut | Compositions useful as a cannabinoid receptor probe |
| FR2714057B1 (fr) | 1993-12-17 | 1996-03-08 | Sanofi Elf | Nouveaux dérivés du 3-pyrazolecarboxamide, procédé pour leur préparation et compositions pharmaceutiques les contenant. |
| US5434295A (en) | 1994-02-07 | 1995-07-18 | Yissum Research Development Company | Neuroprotective pharmaceutical compositions of 4-phenylpinene derivatives and certain novel 4-phenylpinene compounds |
| US5631297A (en) | 1994-07-11 | 1997-05-20 | Pate; David W. | Anandamides useful for the treatment of intraocular hypertension, ophthalmic compositions containing the same and methods of use of the same |
| US5596106A (en) | 1994-07-15 | 1997-01-21 | Eli Lilly And Company | Cannabinoid receptor antagonists |
| US5532237A (en) | 1995-02-15 | 1996-07-02 | Merck Frosst Canada, Inc. | Indole derivatives with affinity for the cannabinoid receptor |
| US5605906A (en) | 1995-03-24 | 1997-02-25 | Merck Frosst Canada, Inc. | Cannabinoid receptor agonists |
| IL113228A (en) | 1995-04-03 | 1999-09-22 | Yissum Res Dev Co | Derivatives of anandamide |
| US5804601A (en) | 1995-04-10 | 1998-09-08 | Takeda Chemical Industries, Ltd. | Aromatic hydroxamic acid compounds, their production and use |
| FR2735774B1 (fr) | 1995-06-21 | 1997-09-12 | Sanofi Sa | Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant |
| IL115245A (en) | 1995-09-11 | 2002-12-01 | Yissum Res Dev Co | Tumor necrosis factor inhibiting pharmaceuticals |
| FR2741621B1 (fr) | 1995-11-23 | 1998-02-13 | Sanofi Sa | Nouveaux derives de pyrazole, procede pour leur preparation et compositions pharmaceutiques en contenant |
| FR2742148B1 (fr) | 1995-12-08 | 1999-10-22 | Sanofi Sa | Nouveaux derives du pyrazole-3-carboxamide, procede pour leur preparation et compositions pharmaceutiques les contenant |
| US5688825A (en) | 1996-05-31 | 1997-11-18 | University Of Connecticut | Anandamide amidase inhibitors as analgesic agents |
| US5760225A (en) | 1996-11-15 | 1998-06-02 | Neurogen Corporation | Certain pyrazole derivatives as corticotropin-releasing factor receptor CRF1 specific ligands |
| DE19706903A1 (de) | 1997-02-21 | 1998-08-27 | Bayer Ag | Verwendung von bekannten Agonisten des zentralen Cannabinoid-Rezeptors CB 1 |
| EP0979228A4 (en) | 1997-03-18 | 2000-05-03 | Smithkline Beecham Corp | CANNABINOID RECEPTOR AGONISTS |
| US5925628A (en) | 1997-03-31 | 1999-07-20 | Genzyme Corporation | Cationic amphiphiles for intracellular delivery of therapeutic molecules |
| US5939429A (en) | 1997-09-30 | 1999-08-17 | Virginia Commonwealth University | Cardiovascular uses of cannabinoid compounds |
| CA2340445A1 (en) | 1998-05-04 | 1999-11-11 | The University Of Connecticut | Novel analgesic and immunomodulatory cannabinoids |
| CA2340444A1 (en) | 1998-05-04 | 1999-11-11 | The University Of Connecticut | Cannabinoids selective for the cb2 receptor |
| US7589220B2 (en) | 1998-06-09 | 2009-09-15 | University Of Connecticut | Inhibitors of the anandamide transporter |
| WO1999064389A1 (en) | 1998-06-09 | 1999-12-16 | Alexandros Makriyannis | Inhibitors of the anandamide transporter as analgesic agents |
| US7897598B2 (en) | 1998-06-09 | 2011-03-01 | Alexandros Makriyannis | Inhibitors of the anandamide transporter |
| EP1049474A4 (en) | 1998-11-24 | 2004-12-29 | Univ Connecticut | CANNABIMIMETIC LIPID AMIDES FOR USE AS MEDICINES |
| MXPA02005104A (es) | 1999-10-18 | 2003-09-25 | Alexipharma Inc | Agonistas novedosos de canabinoide biciclico para el receptor canabinoide. |
| US7393842B2 (en) | 2001-08-31 | 2008-07-01 | University Of Connecticut | Pyrazole analogs acting on cannabinoid receptors |
| WO2001028329A1 (en) | 1999-10-18 | 2001-04-26 | University Of Connecticut | Peripheral cannabinoid receptor (cb2) selective ligands |
| CA2387892A1 (en) | 1999-10-18 | 2001-04-26 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| CA2387846A1 (en) | 1999-10-18 | 2001-04-26 | University Of Connecticut | Retro-anandamides, high affinity and stability cannabinoid receptor ligands |
| CA2387138A1 (en) | 1999-10-18 | 2001-04-26 | University Of Connecticut | Cannabimimetic indole derivatives |
| IL132661A (en) | 1999-10-31 | 2008-11-26 | Raphael Mechoulam | Agonists specific for peripheral cannabinoid receptors |
| JP2004502642A (ja) | 2000-02-11 | 2004-01-29 | ブリストル−マイヤーズ スクイブ カンパニー | カンナビノイドレセプターモジュレーター、それらの製造方法、および呼吸系および非呼吸系疾患の処置のためのカンナビノイドレセプターモジュレーターの使用 |
| CA2411585A1 (en) | 2000-06-22 | 2001-12-27 | Pharmos Corporation | Novel non-psychotropic cannabinoids |
| WO2002060447A1 (en) | 2001-01-29 | 2002-08-08 | University Of Connecticut | Receptor selective cannabimimetic aminoalkylindoles |
| WO2003005960A2 (en) | 2001-07-13 | 2003-01-23 | University Of Connecticut | Novel bicyclic and tricyclic cannabinoids |
| JP2005507875A (ja) | 2001-08-31 | 2005-03-24 | ユニバーシティ オブ コネチカット | カンナビノイド受容体に作用する新規なピラゾール類似体 |
| WO2003035005A2 (en) | 2001-10-26 | 2003-05-01 | University Of Connecticut | Heteroindanes: a new class of potent cannabimimetic ligands |
| IL147941A0 (en) | 2002-01-31 | 2002-08-14 | Pharmos Corp | Bicyclic cb2 cannabinoid receptor ligands |
| JP2005523259A (ja) | 2002-01-31 | 2005-08-04 | ファーモス コーポレイション | 二環式ｃｂ２カンナビノイド受容体リガンド |
| WO2004017920A2 (en) | 2002-08-23 | 2004-03-04 | University Of Connecticut | Novel biphenyl and biphenyl-like cannabinoids |
| AU2003265663A1 (en) | 2002-08-23 | 2004-03-11 | University Of Connecticut | Keto cannabinoids with therapeutic indications |
-
2002
- 2002-01-25 US US10/466,403 patent/US7329651B2/en not_active Expired - Fee Related
- 2002-01-25 JP JP2002558971A patent/JP2004532185A/ja active Pending
- 2002-01-25 WO PCT/US2002/002157 patent/WO2002058636A2/en not_active Ceased
- 2002-01-25 EP EP02707564A patent/EP1361876A4/en not_active Withdrawn
- 2002-01-25 CA CA002435409A patent/CA2435409A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002058636A3 (en) | 2002-10-10 |
| WO2002058636A2 (en) | 2002-08-01 |
| JP2004532185A (ja) | 2004-10-21 |
| US20040077649A1 (en) | 2004-04-22 |
| EP1361876A2 (en) | 2003-11-19 |
| US7329651B2 (en) | 2008-02-12 |
| EP1361876A4 (en) | 2004-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7329651B2 (en) | Cannabimimetic ligands | |
| EP1820504A1 (en) | Imine compound | |
| Cunha et al. | Structural studies of 4-aminoantipyrine derivatives | |
| KR100217167B1 (ko) | 신규 벤조피란 유도체 | |
| KR102305710B1 (ko) | Gpr84 수용체 길항제 및 이의 용도 | |
| EP1363632B1 (en) | Receptor selective cannabimimetic aminoalkylindoles | |
| Habibi et al. | Efficient synthesis of arylaminotetrazoles in water | |
| JP2008546731A5 (enExample) | ||
| WO1997001551A1 (en) | Pyrazole compounds and pharmaceutical compositions | |
| US5412117A (en) | Benzopyran derivatives | |
| CA2088431C (en) | Process for producing 4-bromomethylbiphenyl compounds | |
| KR920006419B1 (ko) | 옥소프탈라지닐 초산 및 그의 유사체의 제조방법과 그의 제조를 위한 중간체 | |
| Hashem et al. | Synthesis and reactions of some 2 (3h) and 2 (5h) furanone derivatives: a comparative study | |
| CN107501328B (zh) | 一种β-硫氰基烯基膦酰类衍生物及其制备方法 | |
| Mosti et al. | Reaction of 2‐dimethylaminomethylene‐1, 3‐diones with dinucleophiles. V. Synthesis of 5‐acyl‐1, 2‐dihydro‐2‐oxo‐3‐pyridinecarbonitriles and 1, 2, 5, 6, 7, 8‐hexahydro‐2, 5‐dioxo‐3‐quinolinecarboxamides | |
| NO173061B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive 2-benzotiazoliner | |
| US20050245750A1 (en) | Process for preparing 1,3-benzodioxole-2-spirocycloalkane derivative | |
| JP4408578B2 (ja) | ３−（１−ヒドロキシ−ペンチリデン）−５−ニトロ−３ｈ−ベンゾフラン−２−オン、その製造方法及びその用途 | |
| US4478996A (en) | Process for the preparation of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxides | |
| CA2176124A1 (en) | 4-(1h-2-methylimidazo 4,5-c pyridinylmethyl)phenyl sulphonamide carboxylic acid derivatives as antagonists | |
| AU2002241964A1 (en) | Novel cannabimimetic ligands | |
| TWI628181B (zh) | 一種ｄｐｐ－ｉｖ抑制劑的中間體、其製備方法和藉由其製備ｄｐｐ－ｉｖ抑制劑的方法 | |
| IL93393A (en) | Process for the preparation of omicron-carboxypyridyl and omicron-carboxyquinolyl- imidazolinones | |
| CN106008506A (zh) | 取代嘌呤类衍生物及其制备方法与应用 | |
| AU609929B2 (en) | Process for the preparation of 3-(3-pyridyl)-1h,3h-pyrrolo {1,2-c}thiazole-7-carbonitrile |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |