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
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- 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
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 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
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- 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
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- 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
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- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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
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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 |
| US7276613B1 (en) | 1998-11-24 | 2007-10-02 | University Of Connecticut | Retro-anandamides, high affinity and stability cannabinoid receptor ligands |
| US7161016B1 (en) | 1998-11-24 | 2007-01-09 | University Of Connecticut | Cannabimimetic lipid amides as useful medications |
| US8084467B2 (en) * | 1999-10-18 | 2011-12-27 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US7741365B2 (en) * | 1999-10-18 | 2010-06-22 | University Of Connecticut | Peripheral cannabinoid receptor (CB2) selective ligands |
| EP1223808B1 (en) | 1999-10-18 | 2007-03-07 | The University Of Connecticut | Peripheral cannabinoid receptor (cb2) selective ligands |
| US6900236B1 (en) | 1999-10-18 | 2005-05-31 | University Of Connecticut | Cannabimimetic indole derivatives |
| US7393842B2 (en) * | 2001-08-31 | 2008-07-01 | University Of Connecticut | Pyrazole analogs acting on cannabinoid receptors |
| US6943266B1 (en) * | 1999-10-18 | 2005-09-13 | University Of Connecticut | Bicyclic cannabinoid agonists for the cannabinoid receptor |
| US7119108B1 (en) * | 1999-10-18 | 2006-10-10 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| ATE478670T1 (de) | 2001-01-29 | 2010-09-15 | Univ Connecticut | Rezeptor-selektive cannabimimetische aminoalkylindole |
| JP4312594B2 (ja) * | 2001-07-13 | 2009-08-12 | ユニバーシティ オブ コネチカット | 新規な二環式及び三環式カンナビノイド |
| CA2464333C (en) * | 2001-10-26 | 2011-07-26 | University Of Connecticut | Heteroindanes: a new class of potent cannabimimetic ligands |
| US7351729B2 (en) | 2002-03-08 | 2008-04-01 | Signal Pharmaceuticals, Llc | JNK inhibitors for use in combination therapy for treating or managing proliferative disorders and cancers |
| AU2003253005B2 (en) * | 2002-08-14 | 2009-03-19 | Jazz Pharmaceuticals Research Uk Limited | Cannabinoid liquid formulations for mucosal administration |
| JP2006511460A (ja) | 2002-08-23 | 2006-04-06 | ユニバーシティ オブ コネチカット | 治療適応を持つケトカンナビノイド |
| WO2005123053A2 (en) * | 2004-06-22 | 2005-12-29 | Pharmos Limited | Use of cb2 receptors agonists for the treatment of huntington’s disease |
| CA2679373A1 (en) * | 2007-03-02 | 2008-09-12 | 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 |
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| CA2464333C (en) | 2001-10-26 | 2011-07-26 | University Of Connecticut | Heteroindanes: a new class of potent cannabimimetic ligands |
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| WO2004017920A2 (en) | 2002-08-23 | 2004-03-04 | University Of Connecticut | Novel biphenyl and biphenyl-like cannabinoids |
| JP2006511460A (ja) * | 2002-08-23 | 2006-04-06 | ユニバーシティ オブ コネチカット | 治療適応を持つケトカンナビノイド |
-
2002
- 2002-01-25 JP JP2002558971A patent/JP2004532185A/ja active Pending
- 2002-01-25 US US10/466,403 patent/US7329651B2/en not_active Expired - Fee Related
- 2002-01-25 EP EP02707564A patent/EP1361876A4/en not_active Withdrawn
- 2002-01-25 WO PCT/US2002/002157 patent/WO2002058636A2/en not_active Ceased
- 2002-01-25 CA CA002435409A patent/CA2435409A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1361876A2 (en) | 2003-11-19 |
| WO2002058636A2 (en) | 2002-08-01 |
| JP2004532185A (ja) | 2004-10-21 |
| EP1361876A4 (en) | 2004-03-31 |
| WO2002058636A3 (en) | 2002-10-10 |
| US20040077649A1 (en) | 2004-04-22 |
| US7329651B2 (en) | 2008-02-12 |
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